Mini-retirements Archives - The Blog of Author Tim Ferriss Tim Ferriss's 4-Hour Workweek and Lifestyle Design Blog. Tim is an author of 5 #1 NYT/WSJ bestsellers, investor (FB, Uber, Twitter, 50+ more), and host of The Tim Ferriss Show podcast (400M+ downloads) Sat, 04 Mar 2023 00:02:24 +0000 en-US hourly 1 https://i0.wp.com/tim.blog/wp-content/uploads/2019/12/cropped-site-icon-tim-ferriss-2.png?fit=32%2C32&ssl=1 Mini-retirements Archives - The Blog of Author Tim Ferriss 32 32 164745976 How to Say No When It Matters Most (or “Why I’m Taking a Long ‘Startup Vacation'”) https://tim.blog/2015/10/29/startup-vacation-2/ https://tim.blog/2015/10/29/startup-vacation-2/#comments Fri, 30 Oct 2015 02:06:27 +0000 http://fourhourworkweek.com/?p=22904 Saying yes to too much “cool” will bury you alive and render you a B-player, even if you have A-player skills. To develop your edge initially, you learn to set priorities; to maintain your edge, you need to defend against the priorities of others.

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Matt_9509255413_99c9a1a118_z (Photo: Michael Matti)

The wisdom of life consists in the elimination of non-essentials.
— Lin Yutang

Discipline equals freedom.
Jocko Willink

This post will attempt to teach you how to say “no” when it matters most.

At the very least, it will share my story of getting there. It’s a doozy.

Here’s the short version:

I’m taking a long break from investing in new startups. No more advising, either. Please don’t send me any pitches or introductions, as I sadly won’t be able to respond. Until further notice, I am done. I might do the same with interviews, conferences, and much more.

Now, the longer version for those interested:

This post will attempt to explain how I think about investing, overcoming “fear of missing out” (FOMO), and otherwise reducing anxiety.

It’s also about how to kill the golden goose, when the goose is no longer serving you.

I’ll dig into one specifically hard decision — to say “no” to startup investing, which is easily the most lucrative activity in my life. Even if you don’t view yourself as an “investor”—which you are, whether you realize it or not—the process I used to get to no should be useful…

[Warning: If you’re bored by investment stuff, skip the next two bulleted lists.]

Caveat for any investing pros reading this:

  • I realize there are exceptions to every “rule” I use. Most of this post is as subjective as the fears I felt.
  • My rules might be simplistic, but they’ve provided a good ROI and the ability to sleep. Every time I’ve tried to get “sophisticated,” the universe has kicked me in the nuts.
  • Many startup investors use diametrically opposed approaches and do very well.
  • There are later-stage investments I’ve made (2-4x return deals) that run counter to some of what’s below (e.g. aiming for 10x+), but those typically involve a discount to book value, due to distressed sellers or some atypical event.
  • Many concepts are simplified to avoid confusing a lay audience.

Related announcements:

  • I will continue working closely with my current portfolio of startups. I love them and believe in them.
  • I will be returning all unallocated capital in my private Stealth Fund on AngelList. If you’re an investor in that fund, you’ll be getting your remaining money back. My public Syndicate will remain in place for later re-entry into the game.

So, why am I tapping out now and shifting gears?

Below are the key questions I asked to arrive at this cord-cutting conclusion.  I revisit these questions often, usually every month.

I hope they help you remove noise and internal conflict from your life.

The Road to No

ARE YOU DOING WHAT YOU’RE UNIQUELY CAPABLE OF, WHAT YOU FEEL PLACED HERE ON EARTH TO DO? CAN YOU BE REPLACED?

I remember a breakfast with Kamal Ravikant roughly one year ago.

Standing in a friend’s kitchen downing eggs, lox, and coffee, we spoke about our dreams, fears, obligations, and lives. Investing had become a big part of my net-worth and my identity. Listing out the options I saw for my next big moves, I asked him if I should raise a fund and become a full-time venture capitalist (VC), as I was already doing the work but trying to balance it with 5-10 other projects. He could sense my anxiety. It wasn’t a dream of mine; I simply felt I’d be stupid not to strike while the iron was hot.

He thought very carefully in silence and then said: “I’ve been at events where people come up to you crying because they’ve lost 100-plus pounds on the Slow-Carb Diet. You will never have that impact as a VC. If you don’t invest in a company, they’ll just find another VC. You’re totally replaceable.”

He paused again and ended with, “Please don’t stop writing.”

I’ve thought about that conversation every day since.

For some people, being a VC is their calling and they are the Michael Jordan-like MVPs of that world. They should cultivate that gift. But if I stop investing, no one will miss it. In 2015, that much is clear. There have never been more startup investors, and–right along with them–founders basing “fit” on highest valuation and previously unheard of terms. There are exceptions, of course, but it’s crowded. If I exit through the side door, the startup party will roll on uninterrupted.

Now, I’m certainly not the best writer in the world. I have no delusions otherwise. People like John McPhee and Michael Lewis make me want to cry into my pillow and brand “Poser” on my forehead.

BUT… if I stop writing, perhaps I’m squandering the biggest opportunity I have—created through much luck—to have a lasting impact on the greatest number of people. This feeling of urgency has been multiplied 100-fold in the last two months, as several close friends have died in accidents no one saw coming. Life is fucking short. Put another way: a long life is far from guaranteed. Nearly everyone dies before they’re ready.

I’m tired of being interchangeable, no matter how lucrative the game. Even if I’m wrong about the writing, I’d curse myself if I didn’t give it a shot.

Are you squandering your unique abilities? Or the chance to find them in the first place?

HOW OFTEN ARE YOU SAYING “HELL, YEAH!”? 

Philosopher-programmer Derek Sivers is one of my favorite people.

His incisive thinking has always impressed me, and his “hell, yeah!” or “no” essay has become one of my favorite rules of thumb. From his blog:

Those of you who often over-commit or feel too scattered may appreciate a new philosophy I’m trying: If I’m not saying “HELL YEAH!” about something, then I say no.

Meaning: When deciding whether to commit to something, if I feel anything less than, “Wow! That would be amazing! Absolutely! Hell yeah!” – then my answer is no. When you say no to most things, you leave room in your life to really throw yourself completely into that rare thing that makes you say “HELL YEAH!”

We’re all busy. We’ve all taken on too much. Saying yes to less is the way out.

To become “successful,” you have to say “yes” to a lot of experiments.  To learn what you’re best at, or what you’re most passionate about, you have to throw a lot against the wall.

Once your life shifts from pitching outbound to defending against inbound, however, you have to ruthlessly say “no” as your default. Instead of throwing spears, you’re holding the shield.

From 2007-2009 and again from 2012-2013, I said yes to way too many “cool” things. Would I like to go to a conference in South America? Write a time-consuming guest article for a well-known magazine? Invest in a start-up that five of my friends were in? “Sure, that sounds kinda cool,” I’d say, dropping it in the calendar. Later, I’d pay the price of massive distraction and overwhelm. My agenda became a list of everyone else’s agendas.

Saying yes to too much “cool” will bury you alive and render you a B-player, even if you have A-player skills. To develop your edge initially, you learn to set priorities; to maintain your edge, you need to defend against the priorities of others.

Once you reach a decent level of professional success, lack of opportunity won’t kill you. It’s drowning in 7-out-of-10 “cool” commitments that will sink the ship.

These days, I find myself saying “Hell, yes!” less and less with new startups. That’s my cue to exit stage left, especially when I can do work I love (e.g. writing) with 1/10th the energy expenditure.

I need to stop sowing the seeds of my own destruction.

HOW MUCH OF YOUR LIFE IS MAKING VERSUS MANAGING? HOW DO YOU FEEL ABOUT THE SPLIT?

One of my favorite time-management essays is “Maker’s Schedule, Manager’s Schedule” by Paul Graham of Y Combinator fame. Give it a read.

As Brad Feld and many others have observed, great creative work isn’t possible if you’re trying to piece together 30 minutes here and 45 minutes there. Large, uninterrupted block of time — 3-5 hours minimum — create the space needed to find and connect the dots. And one block per week isn’t enough.  There has to be enough slack in the system for multi-day CPU-intensive synthesis. For me, this means at least 3-4 mornings per week where I am in “maker” mode until at least 1pm.

If I’m in reactive mode, maker mode is all but impossible. Email and texts of “We’re overcommitted but might be able to squeeze you in for $25K. Closing tomorrow. Interested?” are creative kryptonite.

I miss writing, creating, and working on bigger projects. YES to that means NO to any games of whack-a-mole.

WHAT BLESSINGS IN EXCESS HAVE BECOME A CURSE? WHERE DO YOU HAVE TOO MUCH OF A GOOD THING?

In excess, most things take on the characteristics of their opposite. Thus:

Pacifists become militants.

Freedom fighters become tyrants.

Blessings become curses.

Help becomes hinderance.

More becomes less.

To explore this concept more, read up on Aristotle’s golden mean.

In my first 1-2 years of angel investing, 90%+ of my bets were in a tiny sub-set of startups. The criteria were simple:

  • Consumer-facing products or services
  • Products I could be a dedicated “power user” of, products that scratched a personal itch
  • Initial target demographic of 25-40-year old tech-savvy males in big US cities like SF, NYC, Chicago, LA, etc. (allowed me to accelerate growth/scaling with my audience)
  • <$10M pre-money valuation
  • Demonstrated traction and consistent growth (not doctored with paid acquisition).
  • No “party rounds”—crowded financing rounds with no clear lead investor. Party rounds often lead to poor due diligence and few people with enough skin in the game to really care.

Checking these boxes allowed me to add a lot of value quickly, even as relatively cheap labor (i.e. I took a tiny stake in the company). Shopify is a great example, which you can read about here (scroll down).

My ability to help spread via word of mouth, and I got what I wanted: great “deal flow.” Deals started flowing in en masse from other founders and investors.

Fast forward to 2015, and great deal flow is now paralyzing the rest of my life.  I’m drowning in inbound.

Instead of making great things possible in my life, it’s preventing great things from happening.

I’m excited to go back to basics, and this requires cauterizing blessings that have become burdens.

WHY ARE YOU INVESTING, ANYWAY?

For me, the goal of “investing” has always been simple: to allocate resources (e.g. money, time, energy) to improve quality of life. This is a personal definition, as yours likely will be.

Some words are so overused as to have become meaningless.  If you find yourself using nebulous terms like “success,” “happiness,” or “investing,” it pays to explicitly define them or stop using them. “What would it look like if I had (or won at) ___ ?” helps. Life favors the specific ask and punishes the vague wish.

So, here: to allocate resources (e.g. money, time, energy) to improve quality of life.

This applies to both the future and the present. I am willing to accept a mild and temporary 10% decrease in current quality of life (based on morale in journaling) for a high-probability 10x return, whether the ROI comes in the form of cash, time, energy, or otherwise. That could be a separate blog post, but conversely:

An investment that produces a massive financial ROI but makes me a complete nervous mess, or causes insomnia and temper tantrums for a long period of time, is NOT a good investment.

I don’t typically invest in public stocks for this reason, even when I know I’m leaving cash on the table. My stomach can’t take the ups and downs, but—like drivers rubbernecking to look at a wreck—I seem incapable of not looking. I will compulsively check Google News and Google Finance, despite knowing it’s self-sabotage. I become Benjamin Graham’s Mr. Market. As counter-examples, friends like Kevin Rose and Chris Sacca have different programming and are comfortable playing in that sandbox. They can be rational instead of reactive.

Suffice to say — For me, a large guaranteed decrease in present quality of life doesn’t justify a large speculative return.

One could argue that I should work on my reactivity instead of avoiding stocks. I’d agree on tempering reactivity, but I’d disagree on fixing weaknesses as a primary investment (or life) strategy.

All of my biggest wins have come from leveraging strengths instead of fixing weaknesses. Investing is hard enough without having to change your core behaviors. Don’t push a boulder up a hill just because you can.

Public market sharks will eat me alive in their world, but I’ll beat 99% of them in my little early-stage startup sandbox. I live in the middle of the informational switch box and know the operators.

From 2007 until recently, I paradoxically found start-up investing very low-stress. Ditto with some options trading. Though high-risk, I do well with binary decisions. In other words, I do a ton of homework and commit to an investment that I cannot reverse. That “what’s done is done” aspect allows me to sleep well at night, as there is no buy-sell choice for the foreseeable future. I’m protected from my lesser, flip-flopping self. That has produced more than a few 10-100x investments.

In the last two years, however, my quality of life has suffered.

As fair-weather investors and founders have flooded the “hot” tech scene, it’s become a deluge of noise. Where there were once a handful of micro VCs, for instance, there are now hundreds. Private equity firms and hedge funds are betting earlier and earlier. It’s become a crowded playing field. Here’s what that has meant for me personally:

  • I get 50-100 pitches per week. This creates an inbox problem, but it gets worse, as…
  • Many of these are unsolicited “cold intros,” where other investors will email me and CC 2-4 founders with “I’d love for you to meet A, B, and C” without asking if they can share my e-mail address
  • Those founders then “loop in” other people, and it cascades horribly from there. Before I know it 20-50 people I don’t know are emailing me questions and requests.
  • As a result, I’ve had to declare email bankruptcy twice in the last six months. It’s totally untenable.

Is there a tech bubble? That question is beyond my pay grade, and it’s also beside the point.

Even if I were guaranteed there would be no implosion for 3-5 years, I’d still exit now. Largely due to communication overload, I’ve lost my love for the game.  On top of that, the marginal minute now matters more to me than the marginal dollar.

But why not cut back 50%, or even 90%, and be more selective?  Good question. That’s next…

ARE YOU FOOLING YOURSELF WITH A PLAN FOR MODERATION?

The first principle is that you must not fool yourself and you are the easiest person to fool.

– Richard P. Feynman

Where in your life are you good at moderation? Where are you an all-or-nothing type? Where do you lack a shut-off switch? It pays to know thyself.

The Slow-Carb Diet succeeds where other diets fail for many reasons, but the biggest is this: It accepts default human behaviors versus trying to fix them. Rather than say “don’t cheat” or “you can no longer eat X,” we plan weekly “cheat days” (usually Saturdays) in advance. People on diets will cheat regardless, so we mitigate the damage by pre-scheduling it and limiting it to 24 hours.

Outside of cheat days, slow carbers keep “domino foods” out of their homes. What are domino foods? Foods that could be acceptable if humans had strict portion control, but that are disallowed because practically none of us do. Common domino foods include:

  • Chickpeas
  • Peanut butter
  • Salted cashews
  • Alcohol

Domino triggers aren’t limited to food. For some people, if they play 15 minutes of World of Warcraft, they’ll play 15 hours. It’s zero or 15 hours.

For me, startups are a domino food.

In theory, “I’ll only do one deal a month” or “I’ll only do two deals a quarter” sound great, but I’ve literally NEVER seen it work for myself or any of my VC or angel friends. Sure, there are ways to winnow down the pitches. Yes, you can ask “Is this one of the top 1-2 entrepreneurs you know?” to any VC who intro’s a deal and reject any “no”s. But what if you commit to two deals a quarter and see two great ones the first week? What then? If you invest in those two, will you be able to ignore every incoming pitch for the next 10 weeks?

Not likely.

For me, it’s all or nothing. I can’t be half pregnant with startup investing.  Whether choosing 2 or 20 startups per year, you have to filter them from the total incoming pool.

If I let even one startup through, another 50 seem to magically fill up my time (or at least my inbox). I don’t want to hire staff for vetting, so I’ve concluded I must ignore all new startup pitches and intros.

Know where you can moderate and where you can’t.

YOU SAY “HEALTH IS #1″…BUT IS IT REALLY?

After contracting Lyme disease and operating at ~10% capacity for nine months, I made health #1. Prior to Lyme, I’d worked out and eaten well, but when push came to shove, “health #1” was negotiable. Now, it’s literally #1. What does this mean?

If I sleep poorly and have an early morning meeting, I’ll cancel the meeting last-minute if needed and catch up on sleep. If I’ve missed a workout and have a con-call coming up in 30 minutes? Same. Late-night birthday party with a close friend? Not unless I can sleep in the next morning. In practice, strictly making health #1 has real social and business ramifications. That’s a price I’ve realized I MUST be fine paying, or I could lose weeks or months to sickness or fatigue.

Making health #1 50% of the time doesn’t work. It’s absolute — all or nothing. If it’s #1 50% of the time, you’ll compromise precisely when it’s most important.

The artificial urgency common to startups makes mental and physical health even more challenging. I’m tired of unwarranted last-minute “hurry up and sign” emergencies and related fire drills. It’s a culture of cortisol.

ARE YOU OVER-CORRELATED?

[NOTE: Two investors friends found this bullet slow, as they’re immersed in similar subjects. Feel free to skip if it drags on, but I think there are a few important novice concepts in here.]

“Correlated” means that investments tend to move up or down in value at the same time.

As legendary hedge fund manager Ray Dalio told Tony Robbins: “It’s almost certain that whatever you’re going to put your money in, there will come a day when you will lose 50 percent to 70 percent.” It pays to remember that if you lose 50%, you need a subsequent 100% return to get back to where you started. That math is tough.

So, how to de-risk your portfolio?

Many investors “rebalance” across asset classes to maintain certain ratios (e.g. X% in bonds, Y% in stocks, Z% in commodities, etc.). If one asset class jumps, they liquidate a part of it a buy more of lower performing classes. There are pros and cons to this, but it’s common practice.

From 2007-2009, during the “real-world MBA” that taught me to angel invest, <15% of my liquid assets were in startups. I was taking a barbell approach to investing. But most startups are illiquid. I commonly can’t sell shares until 7-12 years after I invest, at least for my big winners to date. What does that mean? In 2015, startups comprise more than 80% of my assets. Yikes!

Since I can’t sell, the simplest first step for lowering stress is to stop investing in illiquid assets.

I’ve sold large portions of liquid stocks—mostly early start-up investments in China–to help get me to “sleep at night” levels, even if they are lower than historical highs of the last 6-12 months. Beware of anchoring to former high prices (e.g. “I’ll sell when it gets back to X price per share…”). I only have 1-2 stock holdings remaining.

Some of you might suggest hedging with short positions, and I’d love to, but it’s not my forte. If you have ideas for doing so without huge exposure or getting into legal gray areas, please let me know in the comments.

In the meantime, the venture capital model is mostly a bull market business. Not much shorting opportunity. The best approximation I’ve seen is investing in businesses like Uber, which A) have a lot of international exposure (like US blue chips), and B) could be considered macro-economically counter-cyclical. For instance, it’s conceivable a stock market correction or crash could simultaneously lead fewer people to buy cars and/or more people to sign up as Uber drivers to supplement or replace their jobs. Ditto with Airbnb and others that have more variable than fixed costs compared to incumbents (e.g. Hilton).

WHAT’S THE RUSH? CAN YOU “RETIRE” AND COME BACK?

I’m in startups for the long game. In some capacity, I plan to be doing this 20+ years from now.

The reality: If you’re spending your own money, or otherwise not banking on management fees, you can wait for the perfect pitches, even if it takes years. It might not be the “best” approach, but it’s enough. To get rich beyond your wildest dreams in startup investing, it isn’t remotely necessary to bet on a Facebook or Airbnb every year. If you get a decent bet on ONE of those non-illusory, real-business unicorns every 10 years, or if you get 2-3 investments that turn $25K into $2.5M, you can retire and have a wonderful quality of life. Many would argue that you need to invest in 50-100 startups to find that one lottery ticket. Maybe. I think it’s possible to narrow the odds quite a bit more, and a lot of it is predicated on maintaining stringent criteria; ensuring you have an informational, analytical, or behavioral advantage; and TIMING.

Most of my best investments were made during the “Dot-com Depression” of 2008-2009 (e.g. Uber, Shopify, Twitter, etc.), when only the hardcore remained standing on a battlefield littered with startup bodies. In lean times, when startups no longer grace magazine covers, founders are those who cannot help but build a company. LinkedIn in 2002 is another example.

HOWEVER… This doesn’t mean there aren’t great deals out there.  There are. Great companies are still built during every “frothy” period.

The froth just makes my job and detective work 10x harder, and the margin of safety becomes much narrower.

[Tim: Skip this boxed text if the concept of “margin of safety” is old news to you.]

Think of the “margin of safety” as wiggle room.

Warren Buffett is one of the most successful investors of the 20th century and a self-described “value investor.” He aims to buy stocks at a discount (below intrinsic value) so that even with a worst-case scenario, he can do well. This discount is referred to as the “margin of safety,” and it’s the bedrock principle of some of the brightest minds in the investing world (e.g., Seth Klarman). It doesn’t guarantee a good investment, but it allows room for error.  Back in the startup world…

I want each of my investments, if successful, to have the ability to return my “entire fund,” which is how much capital I’ve earmarked for startups over two years, for instance. This usually means potential for a minimum 10X return. That 10X minimum is an important part of my recipe that allows margin for screw ups.

For the fund-justifying ROI to have a snowball’s chance in hell of happening, I must A) know basic algebra to ensure my investment amounts (check sizes) permit it, and B) avoid companies that seem overpriced, where the 10x price is something the world has never seen before (i.e. no even indirect comparables, or tenable extrapolations from even an expanded market size).

If you throw low-due-diligence Hail Mary’s everywhere and justify it with “they could be the next Uber!”, you will almost certainly be killed by 1,000 slow-bleeding $25K paper cuts. Despite current euphoria, applying something like Pascal’s Wager to startups is a great way to go broke.

Good startup investors who suggest being “promiscuous” are still methodical.

It’s popular in startup land to talk about “moonshots”—the impossibly ambitious startups that will either change the world or incinerate themselves into star dust.

I’m a fan of funding ballsy founders (which includes women), and I want many moonshots to be funded, but here’s the reality of my portfolio: as I’ve signed the investment docs for every big success I’ve had, I’ve always thought, “I will never lose money on this deal.”

The “this will be a home run or nothing” deals usually end up at nothing. I’m not saying such deals can’t work, but I try not to specialize in them.

These days, the real unicorns aren’t the media darlings with billion-dollar valuations. Those have become terrifyingly passé. The unicorns are the high-growth startups with a reasonable margin of safety.

Fortunately, I’m not in a rush, and I can wait for the tide to shift.

If you simply wait for blood in the streets, for when true believers are the only ones left, you can ensure come-hell-or-high-water founders are at least half of your meetings.

It might be morbid, but it’s practical.

My Last Deals For A While

It’s still a great time to invest in companies… but only if you’re able to A) filter the signal from the noise, B) say no to a lot of great companies whose investors are accepting insane terms, and C) follow your own rules. Doing all three of these requires a fuck-ton of effort, discipline, and systems. I prefer games with better odds.

There are a few deals you’ll see in the upcoming months, which I committed to long ago. These are not new deals.

They are current companies in which I’m filling my pro-rata, or companies postponing funding announcements until they’re most helpful (e.g. launching publicly). Separately, I work closely with the Expa startup lab and will continue to do so. They are largely able to insulate themselves from madness, while using and refining an excellent playbook.

Are You Having a Breakdown or a Breakthrough? A Short How-To Guide

“Make your peace with the fact that saying ‘no’ often requires trading popularity for respect.”
— Greg McKeown, Essentialism

If you’re suffering from a feeling of overwhelm, it might be useful to ask yourself two questions:

– In the midst of overwhelm, is life not showing me exactly what I should subtract?


– Am I having a breakdown or a breakthrough?

As Marcus Aurelius and Ryan Holiday would say, “The obstacle is the way.” This doesn’t mean seeing problems, accepting them, and leaving them to fester. Nor does it mean rationalizing problems into good things. To me, it means using pain to find clarity. Pain–if examined and not ignored–can show you what to excise from your life.

For me, step one is always the same: write down the 20% of activities and people causing 80% or more of your negative emotions.

My step two is doing a “fear-setting” exercise on paper, in which I ask and answer “What is really the worst that could happen if I did what I’m considering? And so what? How could I undo any damage?”

Below is a real-world example: the journal page that convinced me to write this post and kickstart an extended startup vacation.

The questions were “What is really the worst that could happen if I stopped angel investing for a minimum of 6-12 months? Do those worse-case scenarios really matter? How could I undo any potential damage? Could I do a two-week test?”

As you’ll notice, I made lists of the guaranteed upsides versus speculative downsides. If we define “risk” as I like to—the likelihood of an irreversible negative outcome—we can see how stupid (and unnecessarily painful) all my fretting and procrastination was. All I needed to do was put it on paper.

Below is a scan of the actual page.  Click here for an enlarged version.

Further below is a transcribed version (slightly shorter and edited). For a full explanation of how and why I use journaling, see this post.  In the meantime, this will get the point across:

Journal_Startup_Vacation

Transcription:

“The anxiety is mostly related to email and startups: new pitches, new intros, etc.

Do a 2-week test where “no” to ALL cold intros and pitches?

Why am I hesitant? For saying “no” to all:

PROS:

– 100% guaranteed anxiety reduction

– Feeling of freedom

– Less indecision, less deliberation, so far more bandwidth for CREATING, for READING, for PHYSICAL [TRAINING], for EXPERIMENTS.

CONS (i.e. why not?):

– Might find the next Uber (<10% chance) — Who cares? Wouldn’t materialize for 7-9 years. If Uber pops (IPO), it won’t matter.

– Not get more deals. But who cares?

* Dinner with 5 friends fixes it.

* One blog post fixes it. [Here’s an example from 2013 that helped me find Shyp and co-lead their first round]

* NONE of my best deals (Shyp, Shopify, Uber, Twitter, Facebook, Evernote, Alibaba, etc.) came from cold intros from acquaintances.

If try 2 weeks, how to ensure successful:

– I don’t even see interview or [new] startup emails

– No con-calls. [Cite] “con call vacation” –> push to email or EOD [end-of-day review with assistant]

– Offer [additional] “office hours” on Fridays [for existing portfolio]?

I ultimately realized: If I set up policies to avoid new startups for two weeks, the systems will persist. I might as well make it semi-permanent and take a real “startup vacation.”

What do you need a vacation from?

My Challenge To You: Write Down The “What If”s

“I am an old man and I have known a great many troubles, but most of them never happened.”


– Mark Twain

“He who suffers before it is necessary suffers more than is necessary.”

– Seneca

Tonight or tomorrow morning, take a decision you’ve been putting off, and challenge the fuzzy “what if”s holding you hostage.

If not now, when? If left at the status quo, what will your life and stress look like in six months? In one year? In three years? Who around you will also suffer?

I hope you find the strength to say no when it matters most. I’m striving for the same, and only time will tell if I pull it off.

What will I spend my time on next? More crazy experiments and creative projects, of course.  To hear about them first, sign up for my infrequent newsletter. Things are going to get nuts.

But more important — how could you use a new lease on life?

To surf, like this attorney who quit the rat race? To travel with your family around the world for 1,000+ days, like this?  To learn languages or work remotely in 20+ countries while building a massive business? It’s all possible. The options are limitless…

So start by writing them down. Sometimes, it takes just a piece of paper and a few questions to create a breakthrough.

I look forward to hearing about your adventures.

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How to Become a Model Photographer in Brazil https://tim.blog/2010/11/25/wife-hunting/ https://tim.blog/2010/11/25/wife-hunting/#comments Fri, 26 Nov 2010 02:53:07 +0000 http://www.fourhourworkweek.com/blog/?p=3511 Photo: Jeremiah Thompson Before hiring one of my assistants, Charlie, I asked him where he wanted to be in 6 and 12 months. I made him define what he wanted to have and what he wanted to do in both timeframes. At the top of the list was a mini-retirement to Thailand or South America. …

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Photo: Jeremiah Thompson

Before hiring one of my assistants, Charlie, I asked him where he wanted to be in 6 and 12 months.

I made him define what he wanted to have and what he wanted to do in both timeframes. At the top of the list was a mini-retirement to Thailand or South America.

Done and done.

Charlie just returned three weeks ago from Buenos Aires. It was there he developed a rather keen interest in Brazilian girls, who were visiting Argentina as tourists. Two weeks ago at around 2am, while preparing the new book launch at my house, he somehow accidentally (riiiiight) got stuck in a Flickr slideshow of Brazilian models.

The photos belonged to someone named Jeremiah Thompson.

Digging a little deeper, it turned out that Jeremiah had an incredible story. Two years ago, he decided he wanted to become a professional photographer of Brazilian bikini models. That, and he wanted to get married. Despite the fact that he was from Montana and had no training, he made both happen in record time.

This is his story…

An Interview with Jeremiah Thompson

What’s your background?

I was born in Missoula, Montana, a small college town in the heart of the Rocky Mountains. My Dad was a colonel in the Army so I grew up all over the place, including a couple of stints in Germany. I definitely have a strong entrepreneurial background and have been in business in one form or another all my life, starting at a very young age. The internet has helped me open up a number of businesses.

Did you have much experience as a photographer?

If I thought I could make it rich taking photos, I would have gone into this profession a long time ago. But really, photography has always just been a hobby.

How did you choose Brazil as your destination?

Learning how to surf was, believe it or not, a real stepping stone in my life. About four years ago, I learned how to surf behind an artificial wave put up by a wakeboarding boat. I really got into the sport and wanted to carry my surfing aspirations into the ocean. I narrowed my choices down to Australia and Brazil. A 15-minute phone call to Hans Keeling of Nexus Surf convinced me that Florianopolis, Brazil would be the perfect place for me to go.

[Editor: Some of you might recall that Hans, a recovered ex-lawyer, is a case study in The 4-Hour Workweek]

How did the calendar idea come about?

Arriving in Florianopolis in January of 2008, I was amazed by the sheer quantity of beautiful women — they were everywhere! I’d always had this dream of photographing models, so it was a perfect opportunity to make that dream come true.  I coined the calendar name “Girls of Brazil” and so the adventure began. Then I just needed to find the models.

Photo: Jeremiah Thompson

So, how and where did you find the models?

The first model really set everything into motion.

I was hanging out with Hans Keeling (the owner of Nexus Surf) at Praia Mole Beach, when we passed a super sexy woman working at a fresco paddle rental stand. I had already mentioned my swimsuit calendar idea to Hans, and he happens to speak perfect Portuguese. I asked him if he would help me talk to her and pitch the idea. At this point, I had no product or business cards — just a pair of board shorts, my camera, and some photos of wildlife I had taken in Montana. But that was all I needed. It worked. She agreed to meet me the next day! She was even going to hitchhike to my house at 5:00 AM! I convinced her to let me pick her up, and we shot the next day from 5:30 AM till 8:30 PM. It was a great start to my project.

Photo: Jeremiah Thompson

After that, I found most of the girls on my own, speaking to them in very basic (if not completely broken) Portuguese. I was able to find girls almost everywhere – at the beaches, clubs, supermarkets, walking down the street, and even online. It was too easy. Once I had a few great shots under my belt, I was able to show these same photos to other girls, and most wanted to participate just to get their own pictures taken.

Were they professional models?

The girls were, for the most part, your everyday gals. I did shoot one girl who was actually an international model. I found her while I was driving down the street. I jumped out of my car, chased after her, and asked if she wanted to participate. You would think someone like that would laugh at me, but she ended up making the photos:

Photo: Jeremiah Thompson

Quite a few of the models had experience as event girls. I had the best luck finding those girls online.

But my best photos came from the girls with no professional experience. They always came to the shoots with the most energy. Their openness allowed me more freedom to infuse my own ideas into the photo shoot. This definitely made things more fun, and the results were always great.

Did you pay them for the shoots?

During the first year, I never paid any of the models. By the second year, I started paying a little. I had been dating one of the models and she helped me realize that many of the girls were actually using their own money just to prepare for the photos. They were paying to get their hair done, manicures/pedicures, new bikinis, etc. It was expensive. I started paying them 500 Brazilian reais, which amounted to approximately $250 US dollars. And because I shot many of the girls multiple times, it was a very small price to pay. However, I’m convinced that even if I didn’t pay anything, I would have just as much success or possibly even more. The girls, especially in the first year, really got excited about the opportunity, even though there was no money involved.

Critics might say you were taking advantage of them. What would you say to that?


One of the cool things about this project is the success they’ve had using my photos afterward.

Four of the girls went on to pose for Playboy Brasil. One of the girls got hired on as a dancer for the top television show in Brazil on Sunday afternoons. Many got modeling jobs. And they’ve all appreciated the opportunity, so that’s one of the best things about doing this.

Furthermore, it is not as if I was making money myself. The first few years of this project were big losses. Frankly I couldn’t afford to pay the girls to participate. This was a project I started more out of my desire to be a swimsuit photographer than to make another dollar. The girls loved the project and the photos. Many participated in multiple years. There weren’t any victims here.

Photo: Jeremiah Thompson

For those who’ve dreamed about being a swimsuit photographer but have never had the chance, can you describe the atmosphere of a shoot?

The atmosphere is definitely one of the best things. It starts when the girls come to my house. I need to see them in their bikinis before we head out so I can prepare for the shoot. In the first year, all of the girls used their own bikinis and that worked great 90% of the time. But I started buying bikinis for the girls in year two. So the first step was always to pick out the best bikinis. We would usually find 2-4 bikinis that we would take to the shoot. After that, we either walked to a nearby local beach or took my car to a more private beach.

Usually, we would arrive before sunrise. This meant the girls had been up since 2:30 AM preparing! I typically rolled out of bed around 5:00 AM. Not an easy thing to do, but when the moment comes and those first rays of light hit a beautiful girl in a tiny bikini, it’s worth it.

Posing the girls was always the most difficult part. I wanted to bring out the best in each girl. I would put them through as many poses as possible, mentally noting how they looked best. Then when the best lighting conditions occurred, I would get the girls into what I already knew would be their best pose. This system worked great.

After the shoots, the first question from the girls was always: ”When will the photos be ready?”

They were thrilled to have shots for their portfolio that would otherwise have cost them at least a week’s pay.

Were there any methods you used to produce better results (i.e. humor to loosen up the model, etc.)?

I enjoyed bringing out the genuine smiles of each girl.

Most model photos always have that super serious look, which is supposed to be sexy. I don’t know if I’m different in this regard, but I always enjoy seeing a girl’s smile more. So for half the photos, I would get the girls smiling their biggest smiles possible, and the other half I would let them revert to that serious but “sexy” look you see in all the magazines. Getting the girls to smile was easy: I would just say “mais sexo!” For two years I thought that phrase meant “sexier!” but I guess it really means “more sex!” So it usually made the girls laugh before going into an even sexier pose. That’s how I discovered the girls’ natural smile and how great it looked in the photos.

What have been some of the more memorable moments from your shoots?

I’ve shot something like 30-40 girls now, and there are so many memories with each girl.

Fernanda was my first model and she will always be one of the best memories of this project. Actually, the first photo I took of her is, to this day, one of the best I have ever taken:

Photo: Jeremiah Thompson

Then there was Iris, who showed up an hour and a half late to our shoot. We jumped in my car and she changed into her bikini as I sped off. When we arrived at the beach, I quickly put her into a pose, and we made this photo [below] in about 10 minutes. It was not a minute too soon, as the sun set right after.

Photo: Jeremiah Thompson

When I think about how much preparation goes into a Sports Illustrated shoot and compare it to some of the photos I’ve taken, I’m amazed by the results I’ve had as a one-man operation. It really is a credit to the beauty of these girls and the environment I am working with down in Brazil.

Last but not least, there’s Dayana. 

She and I ended up getting married, so how could I not mention this as one of my best memories?!  We were really connected right from the beginning. It was a goal of mine to find a woman like Dayana to marry, so having this dream come true as a result of this project was incredible, to say the least.

Photo: Jeremiah Thompson

What sales channels have you used for distribution of the calendar?

I’ve never had the opportunity of getting into the main calendar distribution channels, due to my lateness of releasing the calendars.  I learned afterward that most calendars get released almost a year before the calendar year.

That meant the calendar had been shot as early as two years before. Since I was doing this more for fun than to make money, I decided to release the calendars as close to the calendar year as possible. The models were happy with this, as they didn’t have to wait two years to see their photos debut.  It wasn’t smart business on my part, but again, I wasn’t doing the project to make the most money.

Having said that, we’ve enjoyed being one of the top calendars through Amazon for a couple of years now. We’re giving “Sports Illustrated” a run for their money (at least with Amazon) and I feel a great amount of pride seeing that and knowing how small my operation is compared to them.

Have you done any unique promotions to get the word out?

In 2009, we sent 20,000 calendars to troops in Iraq and Afghanistan. In 2010, we sent approximately 3,000 (I was working with a bigger personal budget in 2009 than in 2010). I hope to get these numbers back up in future years if I stay involved in the project. I always get troop requests and have a list of soldiers who have already requested their copies for 2011. It feels great helping these guys out. Hopefully seeing the beautiful girls on their walls keeps them motivated to stay strong and finish out their missions safe.

What’s the “Girls of Brazil” contest you mentioned to me?

The idea behind the contest is to give someone the chance to live the dream of being a swimsuit photographer. There really is no better place than Brazil for this.

I’d help the lucky winner of this contest along with each step. First, we’ll recruit the girls and find the models he’ll be shooting. Then I’ll give him my camera equipment and teach him how to photograph the girls. The winner will be shooting the girls on his own, but I’ll be around if he needs my help. And afterward, we’ll celebrate the results “Brazilian style”!

The contest doesn’t exist yet, but I’m hoping to get sponsored by a magazine who can feature it. It would make a great story and fill several issues of their magazine with content guys will love.

That sounds like a once-in-a-lifetime experience. If a magazine doesn’t pick up the contest, perhaps we can make it happen 🙂

So, how did his calendars turn out? Take a look at Girls of Brazil website or visit Amazon.  If you want a taste of his photos on Facebook, here’s your fix.

Question of the Day (QOD): If you’re happily married, how did you meet your husband or wife, and do you think someone could engineer the same? Share in the comments!

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Odds and Ends: Blogging Lessons and New Stickers


This post produced a lot of strong responses. Please see my comments below in orange, as well as Jeremiah’s. Related to that, here are a few guidelines I follow while blogging:

Blog Lesson 1 – Please Everyone to Interest No One


If this post put your knickers in a twist, before leaving a snarky comment, realize this: when everyone is your customer, no one is your customer. This is true in business and writing. Bloggers often make the mistake of trying to generalize every post to every person. This is slow suicide and results in plain vanilla posts that offend no one and interest roughly the same. Expect that blog to disappear within two years, whether from reader attrition or blogger boredom.

I prefer to write posts that strongly appeal to at least a portion of my readers, and simply rotate to hit different demographics/psychographics with different posts. If I perfectly hit the nail on the head by educating (or entertaining) 20% of my readership, and they share it with their friends, does it matter if I lose 2-5%? Not in my experience. From what I’ve seen, this is precisely how you build an uberstrong community comprised of readers who actually speak their minds and show an unusual degree of tolerance (by Internet standards, at least).

If you’d like to read the female perspective on the mating and marrying game, here’s another post on this very same blog.

Blog Lesson 2- Strategic Redating of Posts

Some of you have asked, where did the last two posts go? The posts on GetGlue stickers and book promotion parties?

Here’s the answer: I redated them in WordPress so they wouldn’t appear on the homepage. Once time-dependent promotional posts have been up for 48-72 hours, and my core audience has seen them, I redate them, as these posts aren’t valuable to new visitors. There’s only one chance to make a first impression, so I always want strong stand-alone content to dominate my blog homepage. I’d used redating in this fashion for more than two years. Some bloggers go so far as to ensure one of their most popular posts is always displayed first on the homepage, followed then by their most recent.

Hope that explains things.

Eat drink and be merry. Happy Thanksgiving!

New Stickers – The 4-Hour Body

The 4-Hour Body is almost exactly three weeks away, which means a new sticker from GetGlue! This one is of reader, Nathan. To learn how to get it (and all the others) for free, read this:

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5 Travel Lessons You Can Use at Home https://tim.blog/2010/02/25/rolf-potts-vagabonding-travel/ https://tim.blog/2010/02/25/rolf-potts-vagabonding-travel/#comments Fri, 26 Feb 2010 05:09:49 +0000 http://www.fourhourworkweek.com/blog/?p=2647 Rolf Potts is one of my favorite writers, and his book Vagabonding was one of only four books I recommended as “fundamental” in The 4-Hour Workweek. It was also one of two books, the other being Walden; Or, Life in the Woods, that I took with me during my 15+-month mini-retirement that began in 2004. …

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Rolf Potts is one of my favorite writers, and his book Vagabonding was one of only four books I recommended as “fundamental” in The 4-Hour Workweek. It was also one of two books, the other being Walden; Or, Life in the Woods, that I took with me during my 15+-month mini-retirement that began in 2004.

The following is a guest post from Rolf on the art and lessons of travel, all of which you can apply at home.

Enter Rolf:

Last fall I spoke at the excellent DO Lectures, which brings innovative thinkers from around the world for a series of talks in rural Wales (Tim was a speaker in 2008). My talk, which is available in full via the video link above encourages people to make themselves rich in time and to become active in making their travel dreams happen.

The talk itself contains essential advice and inspiration regarding travel — but what struck me on re-watching it was an improvised moment at the beginning of the talk, when I pointed out how “these aren’t really travel-specific challenges — these are things that can apply to life in general. Think of travel as a metaphor for how you live your life at home.”

Indeed, travel has a way of slowing you down, of waking you up, of pulling you up out of your daily routines and seeing life in a new way. This new way of looking at the world need not end when you resume your life at home.

Here are 5 key ways in which the lessons you learn on the road can be used to enrich the life you lead when you return home…

1) Time = Wealth

By far the most important lesson travel teaches you is that your time is all you really own in life. And the more you travel, the more you realize that your most extravagant possessions can’t match the satisfaction you get from finding new experiences, meeting new people, and learning new things about yourself. “Value” is a word we often hear in day-to-day life, but travel has a way of teaching us that value is not pegged to a cash amount, that the best experiences in life can be had for the price of showing up (be it to a festival in Rajasthan, a village in the Italian countryside, or a sunrise ten minutes from your home).

Scientific studies have shown that new experiences (and the memories they produce) are more likely to produce long-term happiness than new things. Since new experiences aren’t exclusive to travel, consider ways to become time-rich at home. Spend less time working on things you don’t enjoy and buying things you don’t need; spend more time embracing the kinds of activities (learning new skills, meeting new people, spending time with friends and family) that make you feel alive and part of the world.

2) Be Where You Are

A great thing about travel is that it forces you into the moment. When you’re celebrating carnival in Rio, riding a horse on the Mongolian steppe, or exploring a souk in Damascus, there’s a giddy thrill in being exactly where you are and allowing things to happen. In an age when electronic communications enable us to be permanently connected to (and distracted by) the virtual world, there’s a narcotic thrill in throwing yourself into a single place, a single moment. Would you want to check your bank-account statement while exploring Machu Picchu in Peru? Are you going to interrupt an experience of the Russian White Nights in St. Petersburg to check your Facebook feed? Of course not — when you travel, you get to embrace the privilege of witnessing life as it happens before your eyes. This attitude need not be confined to travel.

At home, how often do you really need to check your email or your Twitter feed? When you get online, are you there for a reason, or are you simply killing time? For all the pleasures and entertainments of the virtual-electronic world, there is no substitute for real-life conversation and connection, for getting ideas and entertainment from the people and places around you. Even at home, there are sublime rewards to be had for unplugging from online distractions and embracing the world before your eyes.

3) Slow Down

One of the advantages of long-term travel (as opposed to a short vacation) is that it allows you to slow down and let things happen. Freed from tight itineraries, you begin to see the kinds of things (and meet the kinds of people) that most tourists overlook in their haste to tick attractions off a list. A host of multi-million-dollar enterprises have been created to cater to our concept of “leisure,” both at home and on the road — but all too often this definition of leisure is as rushed and rigidly confined as our work life. Which is more emblematic of leisure — a three-hour spa session in an Ubud hotel, or the freedom to wander Bali at will for a month?

All too often, life at home is predicated on an irrational compulsion for speed — we rush to work, we rush through meals, we “multi-task” when we’re hanging out with friends. This might make our lives feel more streamlined in a certain abstracted sense, but it doesn’t make our lives happier or more fulfilling. Unless you learn to pace and savor your daily experiences (even your work-commutes and your noontime meals) you’ll cheating your days out of small moments of leisure, discovery and joy.

4) Keep it Simple

Travel naturally lends itself to simplicity, since it forces you to reduce your day-to-day possessions to a few select items that fit in your suitcase or backpack. Moreover, since it’s difficult to accumulate new things as you travel, you to tend to accumulate new experiences and friendships instead — and these affect your life in ways mere “things” cannot.

At home, abiding by the principles of simplicity can help you live in a more deliberate and time-rich way. How much of what you own really improves the quality of your life? Are you buying new things out of necessity or compulsion? Do the things you own enable you to live more vividly, or do they merely clutter up your life? Again, researchers have determined that new experiences satisfy our higher-order needs in a way that new possessions cannot — that taking a friend to dinner, for example, brings more lasting happiness than spending that money on a new shirt. In this way, investing less in new objects and more in new activities can make your home-life happier. This less materialistic state of mind will also help you save money for your next journey.

5) Don’t Set Limits

Travel has a way revealing that much of what you’ve heard about the world is wrong. Your family or friends will tell you that traveling to Colombia or Lebanon is a death-wish — and then you’ll go to those places and have your mind blown by friendliness, beauty and new ways of looking at human interaction. Even on a day-to-day level, travel enables you to avoid setting limits on what you can and can’t do. On the road, you naturally “play games” with your day: watching, waiting, listening; allowing things to happen. There’s no better opportunity to break old habits, face latent fears, and test out repressed facets of your personality.

That said, there’s no reason why you should confine that sort of freedom to life on the road. The same Fear-Industrial Complex that spooks people out of traveling can discourage you from trying new things or meeting new people in own your hometown. Overcoming your fears and escaping your dull routines can deepen your home-life — and the open-to-anything confidence that accompanies travel can be utilized to test new concepts in a business setting, rejuvenate relationships with friends and family, or simply ask that woman with the nice smile if she wants to go out for coffee. In refusing to set limits for what is possible on a given day, you open yourself up to an entire new world of possibility.

Naturally, this list is just a sampling of how travel can transform your non-travel life. What have I missed? What has travel taught you about how to live life at home?

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If you’ve ever fantasized about taking time off to globe-trot, I would highly recommend Rolf Pott’s Vagabonding. It is one of only two books I took with me when I traveled the world for 18 months. Outside Magazine founding editor Tim Cahill calls Vagabonding “the most sensible book of travel related advice ever written.”

I recently partnered with Rolf to release the exclusive audiobook for Vagabonding. For more on this incredible book, click here.

Footnote from Tim: Are you planning, in the middle of, or returning from a long journey? If so — and if you’d like your travel blog or lifestyle-design website to be featured as one of Rolf’s Vagabonding Case Studies — drop him a line at casestudies [at] vagabonding.net and tell him a little about yourself.

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Random Episode 5: The Bloody, Filthy Travel Edition https://tim.blog/2009/08/27/random-episode-5-the-bloody-filthy-travel-edition/ https://tim.blog/2009/08/27/random-episode-5-the-bloody-filthy-travel-edition/#comments Thu, 27 Aug 2009 18:51:21 +0000 http://www.fourhourworkweek.com/blog/?p=2148 This is a short Random episode — 10:30 — and easily the most disgusting to date. I also think it’s the funniest. Imagine Anthony Bourdain’s No Reservations if he didn’t need to edit for cable. This episode has some educational bits, but it’s focus is on enjoying the not-always-so-smooth experience of travel. Not for the …

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This is a short Random episode — 10:30 — and easily the most disgusting to date. I also think it’s the funniest. Imagine Anthony Bourdain’s No Reservations if he didn’t need to edit for cable.

This episode has some educational bits, but it’s focus is on enjoying the not-always-so-smooth experience of travel.

Not for the faint of heart.

From Glenn:

The following video segment is a continuation of the randomly shot randomian-thought random show project with Tim Ferriss and Kevin Rose. This time, we’re not in a library nor are we out on a boat dock fishing for fish – we’re on a street corner in Jinggu. At night. And it’s not really cold outside. It’s slightly humid with a dusty breeze coming out of the southwest.

Audio Note: Most of this was recorded with a Shure-VP88 stereo condenser mic (good with headphones). Apologies for when I don’t have it pointed in correct direction (sounds like they’re behind us).

To borrow from Gary Vee, here is the Question of the Day (QOD): What is the most disgusting or confusing travel experience you’ve ever had?

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Want to get Random episodes delivered to your iPhone or iPad? Now you can! Just subscribe to the podcast in iTunes (or get the audio-only version here).

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How to Be Jason Bourne: Multiple Passports, Swiss Banking, and Crossing Borders https://tim.blog/2009/03/03/how-to-be-jason-bourne-multiple-passports-swiss-banking-and-crossing-borders/ https://tim.blog/2009/03/03/how-to-be-jason-bourne-multiple-passports-swiss-banking-and-crossing-borders/#comments Tue, 03 Mar 2009 12:34:51 +0000 http://www.fourhourworkweek.com/blog/?p=1350 Is it possible to become invisible without breaking the law? (Photo: gravitywave) LOS ANGELES, MID-JUNE 2008 Sitting on a plush couch in the neon-infused nightclub, I asked again: “What’s it about?” Neil Strauss glanced around and looked nervous, which I found strange. After all, we’d known each other for close to two years now. In …

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Is it possible to become invisible without breaking the law? (Photo: gravitywave)

LOS ANGELES, MID-JUNE 2008

Sitting on a plush couch in the neon-infused nightclub, I asked again:

“What’s it about?”

Neil Strauss glanced around and looked nervous, which I found strange. After all, we’d known each other for close to two years now. In fact, he was – as New York Times bestselling author of The Game and others – one of the first people to see the proposal for The 4-Hour Workweek and offer me encouragement.

“C’mon, dude, give me a break. Don’t you trust me?”

“Guilt. That’s good. Use guilt,” Neil said. But the Woody Allen approach wasn’t working.

“I can’t let the meme out early” he said, “I trust you—I’m just paranoid,” he offered to no one in particular as he downed another RedBull. So I fired a shot in the dark.

“What, are you writing about the 5 Flags or something?”

Neil’s heart skipped a beat and he stared at me for several long seconds. He was stunned.

“What do you know about the 5 Flags?”

I was in.

The 5 Flags

Neil’s new book, Emergency, teaches you how to become Jason Bourne.

Multiple passports, moving assets, lock-picking, escape and evasion, foraging, even how to cross borders without detection (one preferred location: McAllen, Texas, page 390)–it’s a veritable encyclopedia of for those who want to disappear or become lawsuit-proof global citizens…

I proofread the book months ago, and it’s been torture to keep some of the content from you, as I find the topics endlessly fascinating. For example, let’s take the concept of “geoarbitrage” to it’s natural but extreme extension: The 5 Flags. I was first introduced to the 5 Flags approach by a deca-millionaire in San Francisco, but here is Neil’s explanation:

“The way to break free of nationality, according to Schultz’s pamphlet, was to follow a three-flag system. The three flags consist of having a second passport, a safe location for your assets in another country, and a legal address in a tax haven. To these, Hill added a fourth and fifth flag: an additional country as a business base and a number of what he called ‘playground countries’ in which to spend leisure time.”

I never implemented the 5 Flags, but I fantasized about getting a second passport and the infinite options it could provide. Neil actually went out and did it.

I’ll get stopped at the airport in a lock-down; Neil won’t. If the FDIC collapses and bank withdrawals are blocked (as happened in Argentina in 2002 when the currency collapsed due to hyperinflation), I’m out of business; Neil has assets elsewhere.

Do I think the US banks are all going to collapse? Not at all. Do I think it’s intelligent to have a lot of options? Indeed. Do I think it’s fun to read about what billionaires and money launderers do, even if I don’t imitate them? Most definitely.

I’m very happy to offer you an exclusive first look at Emergency. Get this book. The following excerpts will set your mind spinning. Ellipses indicate skipped passages.

Lesson 22 – The Gone With the Wind Guide to Asset Protection

If you wanted to withdraw your entire life savings and move it to a bank in Switzerland, what would you do?

Now that I’d decided to hide my assets offshore, the information from the Sovereign Society conference about the government tracking withdrawals and transfers of more than $10,000 applied to me. It seemed impossible to get the money from my American bank to the Swiss bank Spencer recommended without ringing alarm bells. Even if I moved it in small increments, there would still be a paper trail detailing exactly how much money I’d transferred.

So I did what any resourceful American would do: I bought a book on money laundering.

After all, it isn’t a crime to move money secretly as long as the income’s been reported to the IRS and any other necessary reporting requirements are met. And my intention wasn’t to hide my earnings from the government, customs, or creditors, but to protect it from bank collapses, inflation, seizure, and lawsuits, which required leaving few traces of where it went.

Securing money overseas is not a new idea. Even in the novel Gone With the Wind, Rhett butler keeps his earnings in offshore banks, enabling him to buy a house for Scarlett o’Hara after the Civil War—in contrast to his Southern colleagues, who lose their fortunes due to blockades, inflation, and financial collapse.

For more practical, non-fictional inspiration, I bought Jeffrey Robinson’s 1996 book The Laundrymen. I’d always wondered how empty video stores renting movies for $3 a day could stay in business, and why I’d see Russian thugs running clearly unprofitable frozen yogurt stands on deserted side streets. According to Robinson, it’s because, in order to make illegal funds appear legitimate, crooks will slowly feed the money into the cash registers of a normal business.

“It’s almost impossible to spot an extra $500 coming in daily through the tills of a storefront stocked with 15,000 videos,” he writes. “Nor would anyone’s suspicions necessarily be raised if that same owner ran a chain of twenty video rental stores and, backed up with the appropriate audits, awarded himself an annual bonus of $3.96 million.”

Buried elsewhere in Robinson’s book was the answer I was looking for. The best legal way to surreptitiously move money, it seems, is to buy something that doesn’t lose its cash value when purchased. For example, there’s a black market for people who transfer money by buying expensive jewelry, art, watches, and collectibles, then selling them in their destination country for a small loss—usually no greater than the percentage banks charge for exchanging currencies.

So once AIG private bank in Switzerland returned my phone call—assuming that, unlike Spencer’s [a billionaire who appears earlier in the book] lawyer, they were actually willing to work with me—I planned to go shopping for rare coins.

But if it was all so legitimate, why did it feel so wrong?

While I waited to hear from the Swiss bank, I drove to Burbank to meet with the asset protection lawyers Spencer had recommended, Tarasov and Associates. The receptionist led me into a room with black-and-silver wallpaper where Alex Tarasov sat at a large mahogany desk with a yellow legal pad in front of him. With this pad, he would rearrange my business life forever.

“You did a very smart thing by coming here,” Tarasov said. Twenty- five years ago, he had probably been a frat boy. Maybe even played varsity football. But a quarter century spent sitting at desks scrutinizing legal papers had removed all evidence of health from his skin and physique. “By taking everything you own out of your name, we can hide it from lawyers trying to do an asset search on you.”

“So if they sue me and win, they won’t be able to get anything?”

“We can make it very difficult for them to find the things you own and get at them. It’s not impossible, but the deeper we bury your assets, the more money it’s going to cost to find out where they are. And if we can make that time and cost greater than the worth of the assets, then you’re in good shape.”

Like Spencer had said, this was just insurance. The cost of setting this up would be like taking out a policy against lawsuits.

“So what do you own?” he asked.

I laid it all out for him. “I have a house I’m still paying for. I have some stocks and bonds my grandparents gave me when I was a kid. I have a checking and a savings account. And I have the copyrights to my books.” I paused, trying to remember if I owned anything else. I thought there was more. “I guess that’s about it. I have a secondhand Dodge Durango, I guess. And a 1972 corvette that doesn’t work.”

In truth, I didn’t own that much. But ever since my first college job, standing over a greasy grill making omelets and grilled cheese sandwiches, I had started putting money in the bank. Since then, I’d saved enough to live on for a year or two if I ever fell on hard times or just wanted to see the world. I didn’t want to lose the freedom that came from having a financial cushion and not being in debt for anything besides my house.

“Here’s what we can do,” Tarasov said. He then sketched this diagram on his legal pad:

The stick figure was me. as for the boxes, I had no idea what those were. “These are boxes,” Tarasov explained. I was clearly getting the asset-protection-for-dummies lecture. “Each box represents a different LLC”—limited liability company. “If we can wrap everything in an LLC, and then all those LLCs are owned by a holding company, and that holding company is owned by a trust that you don’t even technically own, then you’re safe.”

I liked that last word. But I didn’t understand the rest of it.

“So we’re just basically making everything really complicated?” I asked.

“That’s the idea. We’ll even put your house in a separate LLC, so that if someone trips and falls, they can’t get at anything else you own.”

When Tarasov was through explaining everything, I couldn’t tell whether I was protecting myself from being scammed or actually being scammed myself. But I trusted Spencer, because he seemed too rich, too smart, and too paranoid to get taken in. So I told Tarasov to start wrapping me up in LLCs until my net-worth was whatever spending money I had in my pocket.

“Once we have these entities set up, we can talk about transferring them to offshore corporations,” Tarasov said as I left.

Lesson 54 – Secrets of Escaped Felons

Kelly Alwood didn’t say a word as he handcuffed my hands behind my back, opened the trunk of a rental car, and ordered me to get inside. With his shaven head, which looked like it could break bottles; his glassy green eyes, which revealed no emotion whatsoever; and the .32 caliber pistol hanging from a chain around his neck, he didn’t seem like the kind of person to cross.

As he shut the trunk over my head, the blue sky of Oklahoma City disappeared, replaced by claustrophobic darkness and new-car smell. Instantly, panic set in.

I took a deep breath and tried to remember what I’d learned. I curled my right leg as far up my body as it would go and dipped my cuffed hands down until I could reach my sock. Inside, I’d stashed the straight half of a bobby pin, which I’d modified by making a perpendicular bend a quarter inch from the top. I removed the pin, stuck the bent end into the inner edge of the handcuff keyhole, and twisted the bobby pin down against the lever inside until I felt it give way.

As I twisted my wrist against the metal, I heard a fast series of clicks, the sound of freedom as the two ends of the cuff disengaged. I released my hand, then made a discovery few people who haven’t been stuffed inside a trunk know: most new cars have a release handle on the inside of the boot that, conveniently, glows in the dark. I pulled on the handle and emerged into the light.

“Thirty-nine seconds,” Alwood said as I climbed out of the trunk. “Not bad.”

I couldn’t believe classes like this even existed. In the last forty-eight hours, I’d learned to hotwire a car, pick locks, conceal my identity, and escape from handcuffs, flexi-cuffs, ducttape, rope, and nearly every other type of restraint.

The course was Urban Escape and Evasion, which offered the type of instruction I’d been looking for to balance my wilderness knowledge. The objective of the class was to learn to survive in a city as a fugitive. Most of the students were soldiers and contractors who’d either been in Iraq or were about to go, and wanted to know how to safely get back to the Green Zone if trapped behind enemy lines.

The class was run by a company called onPoint Tactical. Like most survival schools, its roots led straight to Tom Brown. Its founder, Kevin Reeve, had been the director of Tracker School for seven years before setting off on his own to train navy SEALS, Special Forces units, SWAT teams, parajumpers, marines, snipers, and even SERE instructors. As a bounty hunter, his partner, Alwood, had worked with the FBI and Secret Service to help capture criminals on the Most Wanted list.

As the sun set, we drove to an abandoned junkyard, where Reeve let us practice throwing chips of ceramic insulation from spark plugs to shatter car windows, using generic keys known as jigglers to open automobile doors, and starting cars by sticking a screwdriver in the ignition switch and turning it with a wrench.

As I popped open the trunk on a Dodge with my new set of jigglers, I thought, This is the coolest class I’ve ever taken in my life.

Over a barbecue dinner later that night, Reeve asked why I’d signed up for the course. “I think things have changed for my generation,” I told him. “We were born with a silver spoon in our mouths, but now it’s being removed. And most of us never learned how to take care of ourselves. So I’ve spent the last two years trying to get the skills and documents I need to prepare for an uncertain future.”

I’d never actually verbalized it before. I’d just been reacting and scrambling as the pressure ratcheted up around me. Reeve looked at Alwood silently as I spoke. For a moment, I worried that I’d been too candid. Then he smiled broadly. “You’re talking to the right people. That’s what we’ve been thinking. Kelly has caches all over the country—and in Europe.”

Lesson 28 – Calculate the Odds That You’re In Jail Right Now

ST. KITTS, EASTERN CARIBBEAN

In a few days, I’d be committed to an expense of over half a million dollars, which was more money than I had.

And what was it all for? Symbolic paper. A passport, which is just a teeny little booklet that means nothing to the universe. Realistically, the world wasn’t likely to end in my lifetime. And if it did, everyone on St. Kitts would be just as dead as everyone in America.

If there were a smaller-scale world disaster, things would probably be even worse on an island in the Caribbean, where I was more likely to be a victim of food shortages, droughts, hurricanes, blackouts, and tsunamis. There’s nowhere to run and nowhere to hide on an island—especially one in the smallest country in the Americas. I’d become so focused on my search for a passport—so consumed with escaping the blowback of American politics—that I’d forgotten the survivalist lessons I’d learned on Y2K and 9/11.

Soon, the whole endeavor began to seem like the biggest travesty ever. If something horrible happened in America, would a St. Kitts passport even get me out during a state of emergency? What if it was confiscated by customs agents? Or what if Victor, Maxwell, and Wendell were in collusion and just ripping me off? I didn’t have anyone to protect me here.

Once I’d ridden out that wave of anxiety, a new one formed. I began worrying that I’d blabbed my name and occupation to too many people. If they Googled me and saw the filth I’d written, they might not sell me the apartment or give me a citizenship. And then I’d be stuck in America if anything bad happened.

And so it went, all night, one wave of anxiety after another—half of them spent worrying that I wouldn’t get a passport, the other half spent worrying that I would.

I fell asleep around dawn for a few fitful hours, until I was woken by my cell phone. AIG Private Bank was finally returning my call.

Every day, my small savings were dwindling as the dollar dropped relative not just to the euro, but even to the Caribbean currency here. I never thought I’d see the day when Eastern Europeans came to the United States for the cheap shopping.

“I’d like to inquire about opening a private banking account,” I told the woman.

“Great,” she said, with barely a trace of a Swiss accent. “Let me ask you a few questions.”

“Sure.”

“Are you an American citizen?”

“Yes, I am.”

“We don’t deal with American citizens for a few years now.”

“But my friend Spencer Booth is American, and I think he has an account with you.”

“It’s likely an older account. We don’t do business with American citizens anymore. Sorry, good-bye.”

Before I could respond, she had hung up. I felt like an outcast. I couldn’t believe a bank wouldn’t take my money solely because I was American.

I’d noticed that many of the banks I’d researched had special policies for dealing with United States citizens. Even some of the online companies selling vintage travel documents said they no longer shipped to America because U.S. customs agents were opening and confiscating the packages. The government seemed to be sticking its nose everywhere.

In the meantime, I’d discovered a few other interesting facts: according to a report issued by Reporters Without Borders, the United States was ranked as having the fifty-third freest press in the world, tied with Botswana and Croatia. According to the World Health organization, the United States had the fifty-fourth fairest health care system in the world, with lack of medical coverage leading to an estimated 18,000 unnecessary deaths a year. And according to the Justice Department, one in every thirty-two Americans was in jail, on probation, or on parole.

Rather than having actual freedom, it seemed that, like animals in a habitat in the zoo, we had only the illusion of freedom. As long as we didn’t try to leave the cage, we’d never know we weren’t actually free.

That phone call was all it took to let me know I was doing the right thing.

Before going home, I had dinner with Wendell at a restaurant called Fisherman’s Wharf [in St. Kitts, not San Francisco] and thanked him for his help.

After the meal, he patted my shoulder and smiled. “Next time I see you, you’ll be a citizen of St. Kitts and Nevis just like me,” he said. “When you get married, your wife will be a citizen. And when you have kids, so will they.”

He stepped into his SUV, started the engine, then unrolled the window and concluded his thought: “One day,” he said, beaming, “when you come back to America, no one will recognize you. You’ll be a Kittitian.”

At the St. Kitts airport the next morning, I felt like I was returning not to a country but a fortress. “Your country is so tough to get into,” the ticket agent complained as she checked my documents for the flight home. “They make it so hard for us.”

She looked up at me and said it louder, almost with venom, as if it were my fault. “They make it so hard for us.”

She wasn’t alone in her opinion. A survey released the previous month by the Discover America Partnership had found that international travelers considered America the least-friendly country to visit.

“That’s why,” I told her, with the newfound pride that Wendell had instilled in me, “I’m moving here.”

Lesson 59 – Iceland is the New Caribbean

Maybe it was when Bear Stearns became the first brokerage house to be rescued by the government since the Great Depression.

Maybe it was when IndyMac became the fifth American bank to fail in recent months.

Maybe it was when the government gave customs agents authority to confiscate, copy, and analyze any laptop or data storage device brought across the border.

Maybe it was the unshakable sense that the worst was still to come.

But I was no longer alone.

It was a hot summer, and pessimism hung thick in the air. Most people I talked to felt as if they were inching closer to some darkness they couldn’t understand, because they’d never experienced it before and didn’t know what it held.

Even Spencer’s housemate Howard, who had once made fun of us for taking precautionary measures, was now looking into Caribbean islands. As it turned out, he would beat all of us there when his company collapsed and he had to hide from possible indictment.

“I’m so glad we started preparing ahead,” Spencer told me over dinner at the Chateau Marmont, where he was staying in Los Angeles.

Having struck out with the Swiss, I took Spencer’s advice and opened an account with a Canadian bank that had a branch in St. Kitts. Since both Canada and St. Kitts are part of the British Commonwealth, he’d explained, I would have easy access to my money if anything happened in America. Unfortunately, in the process, I discovered that keeping international accounts secret is now illegal: the IRS requires Americans with over $10,000 in foreign accounts to file an annual report disclosing not just the amount of money and the banks it’s kept in, but the account numbers.

Meanwhile, Spencer was moving forward with his ten-year plan. He started an Internet business in Singapore, enabling him to open a private banking account in the country, which he claimed was fast becoming the new Switzerland. Though he hadn’t gotten his St. Kitts passport yet either, Spencer had done more research into buying an island.

“I’m looking at islands in the north, around Iceland, because no one will think of looking for anyone there,” Spencer said, his thick lips spreading into a self-satisfied smile. “If I can get some other B people [billionaires] to go there with me, we can build underground homes and use geothermal energy.”

“What about your submarine?”

“It’s a great way to move between islands undetected, but we’re running out of time. We need to move faster. This is only the beginning.”

“How bad do you think it’s going to get?” Spencer seemed to understand the economy at a higher level than most people did, perhaps because he knew so many of the people who ran it.

“I don’t think the whole country’s going to collapse, but we’re looking at the worst economic disaster in America since the Great Depression. What I’m also concerned about is the increase in violent crime that’s going to accompany this.”

Everywhere I went that summer, the demon of Just in Case seemed to follow me, growling in my ear louder than it ever had, its jaws terrifyingly close to my jugular. I’d learned so much, changed so much, tested myself so much. It now was time to stop preparing, turn around, and face the demon—and my fears—head on.

And a musician would lead me there.

###

Note from Tim:  If you enjoyed this piece, you’ll love my extended interview of author Neil Strauss on The Tim Ferriss Show podcast. Click below to stream or you can find it on iTunes (see #15):

Ep. 15: Neil Strauss - Author of The Game and 7 New York Times Bestsellers

Also — If you’ve ever fantasized about taking time off to globe-trot, I highly recommend Rolf Pott’s Vagabonding. It is one of only two books I took with me when I traveled the world for 18 months. Outside Magazine founding editor Tim Cahill calls Vagabonding “the most sensible book of travel related advice ever written.”

 

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How to Surf Life: Attorney Turned Surf Guru https://tim.blog/2008/11/10/how-to-surf/ https://tim.blog/2008/11/10/how-to-surf/#comments Mon, 10 Nov 2008 11:47:11 +0000 http://www.fourhourworkweek.com/blog/?p=827 (Photo: envisionpublicidad) Many a false step was made by standing still. -Fortune Cookie Named must your fear be before banish it you can. -Yoda, Star Wars: The Empire Strikes Back RIO DE JANEIRO, BRAZIL Twenty feet and closing. “Run! Ruuuuuuuuuun!” Hans didn’t speak Portuguese, but the meaning was clear enough—haul ass. His sneakers gripped firmly …

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(Photo: envisionpublicidad)

Many a false step was made by standing still.

-Fortune Cookie

Named must your fear be before banish it you can.

-Yoda, Star Wars: The Empire Strikes Back

RIO DE JANEIRO, BRAZIL

Twenty feet and closing.

“Run! Ruuuuuuuuuun!” Hans didn’t speak Portuguese, but the meaning was clear enough—haul ass. His sneakers gripped firmly on the jagged rock, and he drove his chest forward towards 3,000 feet of nothing.

He held his breath on the final step, and the panic drove him to near unconsciousness. His vision blurred at the edges, closing to a single pin point of light, and then… he floated. The all-consuming celestial blue of the horizon hit his visual field an instant after he realized that the thermal updraft had caught him and the wings of the paraglider. Fear was behind him on the mountain top, and thousands of feet above the resplendent green rain forest and pristine white beaches of Copacabana, Hans Keeling had seen the light.

That was Sunday.

On Monday, Hans returned to his law office in Century City, Los Angeles’ posh corporate haven, and promptly handed in his three-week notice…

For nearly five years, he had faced his alarm clock with the same dread: I have to do this for another 40-45 years? He had once slept under his desk at the office after a punishing half-done project, only to wake up and continue on it the next morning. That same morning, he had made himself a promise: two more times and I’m out of here. Strike number three came the day before he left for his Brazilian vacation.

We all make these promises to ourselves, and Hans had done it before as well, but things were now somehow different. He was different. He had realized something while arcing in slow circles towards the earth—risks weren’t that scary once you took them. His colleagues told him what he expected to hear: he was throwing it all away. He was an attorney on his way to the top—what the hell did he want?

Hans didn’t know exactly what he wanted, but he had tasted it. On the other hand, he did know what bored him to tears, and he was done with it. No more passing days as the living dead, no more dinners where his colleagues compared cars, riding on the sugar high of a new BMW purchase until someone bought a more expensive Mercedes. It was over.

Immediately, a strange shift began—Hans felt, for the first time in a long time, at peace with himself and what he was doing. He had always been terrified of plane turbulence, as if he might die with the best inside of him, but now he could fly through a violent storm sleeping like a baby. Strange indeed.

More than a year later, he was still getting unsolicited job offers from law firms but by then had started Nexus Surf, a premier surf-adventure company based in the tropical paradise of Florianopolis, Brazil. He had met his dream girl, a Carioca with caramel-colored skin named Tatiana [bottom right here], and spent most of his time relaxing under palm trees or treating clients to the best times of their lives.

Is this what he had been so afraid of?

These days, he often sees his former self in the under-joyed and overworked professionals he takes out on the waves. Waiting for the swell, the true emotions come out: “God, I wish I could do what you do.” His reply is always the same: “You can.”

The setting sun reflects off the surface of the water, providing a zen-like setting for a message he knows is true: it’s not giving up to put your current path on indefinite pause. He could pick up his law career exactly where he left off if he wanted to, but that is the furthest thing from his mind.

As they paddle back to shore after an awesome session, his clients get a hold of themselves and regain their composure. They set foot on shore, and reality sinks its fangs in: “I would, but I can’t really throw it all away.”

He has to laugh.

###

Excerpted from The 4-Hour Workweek, Chapter 3: Dodging Bullets – Fear-setting and Escaping Paralysis

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Rolf Potts Q&A: The Art of Long-term World Travel… and Travel Writing https://tim.blog/2008/09/15/rolf-potts-qa-the-art-of-long-term-world-travel-and-travel-writing/ https://tim.blog/2008/09/15/rolf-potts-qa-the-art-of-long-term-world-travel-and-travel-writing/#comments Tue, 16 Sep 2008 02:10:27 +0000 http://www.fourhourworkweek.com/blog/?p=563 Rolf Potts is one of my favorite writers, and his book — Vagabonding — was one of only four books I recommended as “fundamental” in The 4-Hour Workweek. It was also one of two books, the other being Walden; Or, Life in the Woods, that I took with me during my 15+-month mini-retirement that began …

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rolf potts

Rolf Potts is one of my favorite writers, and his book — Vagabonding — was one of only four books I recommended as “fundamental” in The 4-Hour Workweek. It was also one of two books, the other being Walden; Or, Life in the Woods, that I took with me during my 15+-month mini-retirement that began in 2004.

He interviewed me for Yahoo! Travel almost a year and a half ago, and I’m thrilled to have the chance to interview him about his long-awaited new book and the art of travel writing.

Have you ever wondered what it really takes to pull the trigger and embark on long-term world travel?

Have you ever fantasized about getting paid to do it?

Let Rolf give us a look at both…

Is Marco Polo Didn’t Go There a sequel of sorts to Vagabonding?

It is in a sense a sequel — as well as a prequel, of sorts — but it has a different approach than Vagabonding. Vagabonding is at heart a philosophical book about seeing time as wealth and using travel to actualize that wealth. Marco Polo Didn’t Go There is indirectly philosophical; it’s a collection of stories from the road — a showcase of the type of travel experiences that vagabonding has provided for me over the past decade.

So your new book might be considered “vagabonding in practice”?

In a sense, yes. That said, many of the stories are misadventures by conventional definition. In the pages of the new book, I’m always getting into trouble, or falling in with the wrong people, or getting lost somehow. But that’s how travel stories work. People quickly tire of hearing stories about your perfectly blissful days on the road. They want to hear about the times when things went wrong — when you were challenged in unexpected ways. So the new book is skewed toward my more harrowing and/or wacky adventures.

This book is also an examination of my working life as a travel writer. This is communicated in many ways throughout the book, but perhaps most vividly in the endnotes to each story, which comment on the ragged reality that lurks behind a seemingly self-contained travel tale. I like to think of these endnotes as the DVD-style “commentary track” to the book.

[Note from Tim: this “commentary track” is perhaps my favorite feature of all, as it explains the “making of” a first-class world traveler and all the real logistical and cultural challenges that presents. Highly recommended if you have any travel coming up.]

Misadventures aside, how might readers seek out the kinds of travel experiences you describe in the book? That is, how might your average traveler get out of the tourist-circuit rut and find interesting, life-affecting experiences?

The most important thing in seeking richer travel experiences is learning how to slow down. This can be hard to do, since as Americans we tend to micromanage everything to make things more efficient back home.

Travel isn’t about efficiency. It’s about leaving yourself open to new experiences. You can’t do this when you’re racing around on a strict itinerary. If you examine the truly life-affecting experiences I describe in my new book, you’ll find that they most all happened by accident. If you aren’t open to the unexpected — if you aren’t willing to get lost from time to time — you’ll be selling your travels short.

[Suggestion from Tim: reread the previous paragraph substituting “travel” and “travels” with “life”.]

As for the tourist-circuit, slowing your travels down will automatically lead you off the tourist trail. When you aren’t racing from “attraction” to “attraction,” you’ll quickly discover that the best experiences come from the diversions along the way.

How has technology changed the way people travel? Any advice or warnings about using this technology on the road?

In 1994 I took an 8-month vagabonding journey around North America, and there were times when I was out of touch with friends and family for weeks. Nobody was on email back then, and making a long-distance call required a fist-full of quarters and a pay phone. Now, with high-speed Internet and the ubiquity of cell phones, you can never be out of touch. I never called my sister when I was traveling America in ’94, but just last month I was traveling Africa with an AT&T BlackJack and I needed to ask her a question, so I gave her a holler from Lokichokio, Kenya. Even for Kenyans, Lokichokio is the middle of nowhere, but calling her was not a problem. I just punched in her number and got her on the second ring.

The downside is that this kind of communication can easily become one big umbilical cord that ties you to home when you should be experiencing your travel surroundings. Was calling my sister from Kenya really all that urgent and necessary? Probably not. And in a sense I was probably less “in the moment” in Lokichokio than I should have been.

Ideally, you should only check email just one or two times a week when you travel, and use the cell phone only for emergencies or hooking up with local friends as you go. What’s the pleasure in going to Tahiti or Rio or Geneva if you spend most of your time attached to your phone or laptop, sending messages home?

By definition, being a travel writer means you’ve been working from a mobile office for ten years. What advice might you give to people looking manage their work from remote locations as they travel?

Be a minimalist. Reduce clutter. Obviously travel by its very nature is going to do this, since you can’t pack everything you’d keep in your home office. But this should apply to your travel office as well. For example, get a cheap laptop, and use it only for your work. Save your important information into Google documents (or something similar) in case the laptop gets lost or stolen or your pack falls in a river. Don’t use the laptop to surf news online; go to the local newsstand instead. Don’t use the laptop to watch DVDs or listen to music; go to a local cinema or nightclub instead.

This is not just a matter of travel aesthetics or cultural appreciation — it’s a matter of breaking bad habits. Back home we use our work technology to fart around and pass the day. Nobody should travel around the world just to sit in front of a laptop and fart around.

Travel writing as a profession would seem to be a glamorous undertaking. Is it as cool of a job as it sounds?

Absolutely — but not in the way you might think. There are better ways to travel than wandering around and taking notes and spending long stretches of time in your hotel doing typing prose. There are better ways to make money. There are better ways to get into adventures. Just read the endnotes to my new book and you’ll see the limitations and contradictions involved when you go to a place and try to write about it.

So the best part about my job isn’t that it enables me to travel; it comes in the work itself. It comes when I experience an amazing place or a memorable encounter and I’m later able to write something true about that experience — something that communicates the richness and complexity and possibility of being alive.

How did you start your travel writing career?

My writing aspirations can be traced back to about age 13, when I started writing horror stories in the style of Stephen King. This horror-writing phase didn’t last long, but it helped winnow the creative urge, and familiarize me with the basics of putting a prose narrative together. Later I became involved with my high school newspaper, and I wrote a humor column for my campus newspaper in college. After college, I traveled the United States for eight months, living out of a VW van. Fancying myself a kind of new Jack Kerouac, I tried to write a book about this travel experience, but that ultimately failed when I couldn’t interest any agents or editors. Out of money and not sure what to do next, I went to Korea to teach English for a couple years.

In Korea, I learned how to live within another culture, and I became a more seasoned, instinctive traveler. I also learned from the shortcomings of my failed USA travel book, and sharpened my writing, keeping in mind the narrative needs of my readers. During my second year in Korea, I rewrote one of my USA book chapters (about Las Vegas) and sold it to Salon.com’s travel section. Encouraged by this small success, I strengthened my relationship with my Salon editor by writing some travel stories about Korea. He published about five of them.

At this point, I’d saved a lot of money from teaching, and I’d planned on traveling through Asia and Europe for over a year. Since I had an editorial contact at Salon, I decided to pitch him with a travel column idea. He wasn’t sure about this idea at first, so I hit the road on my trip and continued to write stories. It just so happened that Leonardo DiCaprio was shooting the travel-oriented movie “The Beach” in Thailand, so I decided to try and sneak onto the set of the movie as an experiment about the motivations and idiosyncrasies of travel. My attempt to sneak onto the movie set failed, but the resulting story, “Storming ‘The Beach’”, made the cover of Salon and landed in the 2000 edition of The Best American Travel Writing [From Tim: Read this for a flavor of Rolf. You’ll thank me.].

I got the travel column at Salon, and that turned out to be a big turning point in my career, as it raised my exposure one-hundred-fold. Editors of glossy magazines like Condé Nast Traveler invited me to write for them, and I’ve been freelancing for various travel venues — National Geographic Traveler, Outside, Slate, Islands, the San Francisco Chronicle, etc. — ever since. My book, Vagabonding, came out in 2003. I’ve also maintained an author website since 1998, and a blog since 2002, and both have been good for promoting and showcasing my work.

These days, travel is still the core of my work, though I occasionally write literary criticism, interviews, and other types of writing. I’d say travel writing is 80% of what I do.

Any warnings for aspiring travel writers?

Only get into travel journalism if you really love to travel and write. If you think it’s a good pretext for getting to travel, think again: you can travel just as much by saving up money from another, better-paying job, and just taking off to go vagabonding. So only pursue travel writing because you love to write as well. If that admonition hasn’t scared you off, I’ll advise you to write as much as possible, work on your narrative voice (because a vivid or funny voice can make all the difference), do some publication internships, get out there and work on your travel expertise, and — most of all — have fun!

Even if your travels don’t lead to a full-time career, they are a reward in and of themselves.

—-

You can see Rolf Potts at one of 20 cities nationwide as he celebrates the release of Marco Polo Didn’t Go There through mid-November.

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Odds and Ends:

-Check out Weebly.com for simple website creation. I create the following homepage mock-up in 10 minutes: Timothy Ferriss homepage mock-up.

-Good article on digital connection vs. recluse-like behavior (me):

Timothy Ferriss vs. Gary Vaynerchuck

-Haven’t tried Twitter yet? See how I use it — against being called a heretic — here: Timothy Ferriss on Twitter.

The post Rolf Potts Q&A: The Art of Long-term World Travel… and Travel Writing appeared first on The Blog of Author Tim Ferriss.

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12+ Gems of the Pacific Northwest Coast (Plus: 200 Tweets – My Thoughts on Practical Twitter Use) https://tim.blog/2008/07/30/12-gems-of-the-pacific-northwest-coast-plus-200-tweets-my-thoughts-on-practical-twitter-use/ https://tim.blog/2008/07/30/12-gems-of-the-pacific-northwest-coast-plus-200-tweets-my-thoughts-on-practical-twitter-use/#comments Wed, 30 Jul 2008 11:44:44 +0000 http://www.fourhourworkweek.com/blog/?p=392 The unbelievable Oregon coastline. (Photo: liquidskyarts) Six weeks ago I conducted my first social media travel experiment. I posed a simple question and let your responses to me on Twitter and this blog dictate exactly what I did on a 12-day roadtrip with my brother from San Francisco to Vancouver, Canada. No packing or planning …

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The unbelievable Oregon coastline. (Photo: liquidskyarts)

Six weeks ago I conducted my first social media travel experiment. I posed a simple question and let your responses to me on Twitter and this blog dictate exactly what I did on a 12-day roadtrip with my brother from San Francisco to Vancouver, Canada.

No packing or planning was done before jumping in the car (the best proof of this: I needed a friend to FedEx my passport to Seattle so I could get into Canada).

I’d done the trip from SF to Mexico several times, often meticulously planned, and this trip — my first up through the northwest coast — was both more fun and less stressful. Here is the progression of my “tweets” (Twitter entries), beginning with the first question…

Off Wed. on a road trip with my bro from SF to Portland, Seattle, then Vancouver. What are your top B&B and must-see picks? B&B rec’s pls! 02:26 AM June 17, 2008

Day 1: SF to Eureka. 101N to lunch at Ukiah Brewing Co., then Avenue of Giants, to Eureka, dinner at Lost Coast Brewery, bed @ dalyinn.com 11:25 AM June 19, 2008

Day 2: to Eugene. Samoa Cookhouse snipurl.com/2ltjq , 500 ft dunes that inspired ‘Dune’ snipurl.com/2ltkx, and sleep @ The Campbell House 10:12 AM June 20, 2008

Day 3-Portland: Powell’s Books, btl of Pinot @ Vino Paradiso (1/2 off @ happy hr), dinner @ Jake’s Famous Crawfish (top-10 seafood in US). 12:55 PM June 21, 2008

Day 4-Portland: woke @ 12, Voodoo Doughnut feast, Saturday Market, rose garden @ Forest Park, movie @ Kennedy School, finish w/ Vault Martini. 02:08 AM June 22, 2008

Voodoo Doughnut’s delicious Maple Bacon doughnut and meth-high-inducing Grape Ape doughnut.

Day 5-to/in Seattle: stop @ bridge of glass http://snipurl.com/2o8ub, amazing espresso @ vivace (espressovivace.com), and dinner at Kells. 01:03 PM June 24, 2008

Day 6-Seattle: lunch @ Cutters, ‘Mongol’ @ the Egyptian Theater, KICK-ASS Remedy Tea (200+ teas) for night cap. Get the ginger/matcha shot. 09:08 PM June 24, 2008

Day 7-Seattle: presented to CIA (no joke), Underground Tour (undergroundtour.com), amazing crab cakes at Etta’s, reading Zorba The Greek… 07:44 PM June 25, 2008

Day 8-to Vancouver: Zoka coffee testing, Seattle (zokacoffee.com); drive up I-5/99 to Vancouver; sushi & sashimi at ‘Asahi-ya’ 1230 Robson. 11:00 AM June 26, 2008

Any recs for vancouver meetup spots and sleeping? Must do’s? 04:36 PM June 26, 2008

Day 9-Vancouver: Stanley Park (incl. totems), best comic/anime exhibit ever (http://snipurl.com/2pps8), amazing Malaysian @ The Banana Leaf 11:21 PM June 26, 2008

Day 10-Whistler BC: excellent hiking to Joffrey Lakes, saw black bear on hillside, incredible pizza in Pemberton at http://ponyespresso.ca/ 10:54 AM June 29, 2008

(Photo: ucumari)

Day 11-Vancouver: Lamb popsicles @ Vij’s, Sauv Blanc fr Alsace, hanging w/ Cameron Herold (http://snipurl.com/2r5gd), + Wall-E… AWESOME. 02:16 PM June 29, 2008

Day 12-Fly Seattle to SF for $98 on Alaskan; ship car from Seattle to SF for $640 www.ableautotransport.com = $ than hotels and gas 09:44 PM June 30, 2008

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Links above, when not written out using shorthand from SnipURL, were added for this blog post.

200 Tweets – My Thoughts on Practical (vs. Addictive) Uses of Twitter

I don’t follow anyone on Twitter. To some, this is sacrilege.

Let me explain the main reason of several that I don’t follow people:

Imagine that you send an email to 10 people inviting them to a party, but you BCC 100 more casual friends who are uninvited. How will those 100 feel? Offended and somewhat resentful, just as I would.

Twitter is like this: all followers and followees are transparent. I can’t follow a single person without risking irritating hundreds. This problem is the same for someone who has 40 followers as it is for someone with 40,000. I avoid the drama and politics by following no one. I do this because I don’t care to be a hypocrite (low-information diet, etc.) and do care about my followers, not because I’m uninterested in them. I track some of my followers regularly but don’t “follow” in the formal sense.

I “follow” my close friends via food, wine, texting, and — for old classmates — Facebook.

Here are several quotes about Twitter relevant to my 3 personal rules of Twitter use:

“Twitter is a community. It’s not all about you. Engage your peers by asking them questions”

Micki Krimmel, video blogger and host of Mickipedia

“Don’t try to impress–just be yourself. But go a little beyond your comfort zone; share something you’re hesitant about sharing.”

Evan Williams, co-founder of Obvious, which created Twitter

[my panel interview with Evan here]

Here are my 3 basic “Twittiquette” rules of using Twitter:

1. Add value if you consume attention.

I use Twitter as a “micro-blogging” platform, exactly how it’s most often described. Just as I wouldn’t put up a blog post that reads “just ate a burrito. Mmmm… good,” as it consumes readers valuable attention without adding value, I wouldn’t put up such a post on Twitter. On the other hand, “Just had an incredible mahi-mahi burrito at [best unknown taco stand] in San Diego. Must-eat: www.website.com In NYC, try: www.website2.com” adds value with actionable details. Mundane perhaps, but still a cool “to-do” that ethnic food lovers can tuck in the back of their heads.

Some self-indulgent tweets are fine, but make sure 90%+ help or entertain your readers somehow. Information empty calories are parasitic.

2. Use the tool for its best purposes and ignore the rest.

Use a tool for what its best suited to do. Don’t make a Swiss army knife out of every social media tool or you’ll end up with nothing but overwhelm, passive-aggressive “friends,” and a dozen separate inboxes.

I use the blog for testing ideas/campaigns/memes, catalyzing social change, and introducing more developed concepts so I can watch and track their impact and evolution in the blogosphere.

I use Twitter to broadcast time-sensitive suggestions, questions, events, random facts, and happenings, and other ideas that don’t justify an independent blog post. I don’t want another IM program.

I hate page view-driven sites that force features on users in the quest for more clicks. 500+ unread messages on Facebook? 600+ unread requests on LinkedIn? That’s what e-mail is for.

3. Linking is fundamental to adding value.

Twitter is perfect for honing your word economy and value-to-attention contribution: offer a brief takeaway and quicks links to more resources for those interested. Minimal attention impact for the uninterested with gateways to more goodies. Here are a few recent examples.

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Thanks to all for the killer suggestions for my trip! Much crazier stuff coming if you want to follow me here.

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How to Take a Mini-Retirement: Tips and Tricks https://tim.blog/2008/06/04/how-to-take-a-mini-retirement-tips-and-tricks/ https://tim.blog/2008/06/04/how-to-take-a-mini-retirement-tips-and-tricks/#comments Wed, 04 Jun 2008 08:54:22 +0000 http://www.fourhourworkweek.com/blog/?p=364 I was recently interviewed by J.D. Roth on planning and financing mini-retirements. Here is an excerpt: J.D. It occurs to me that one way to approach the mini-retirements, at least financially, is to save for them, just as I might save for a new car. It’s not necessarily money I’m pulling from retirement then. It’s …

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I was recently interviewed by J.D. Roth on planning and financing mini-retirements. Here is an excerpt:

J.D.

It occurs to me that one way to approach the mini-retirements, at least financially, is to save for them, just as I might save for a new car. It’s not necessarily money I’m pulling from retirement then. It’s money I’m pulling away from a Mini Cooper and setting aside for a mini-retirement. I think the mini-retirement would actually provide more value to me at this point.

Tim

Well, sure. And I think one assumption that [you’re making] is that you spend and not save money on a mini-retirement. Let me offer a personal example. The personal stories in the book are mostly from experiences I had between 2004 and early 2006, traveling around the world for about 18 months. During the first twelve month period of time, I actually saved $32,000 when compared to sitting on my couch watching The Simpsons in my apartment in the Bay Area.

J.D.

That’s amazing.

Tim

When you recognize that the costs of travel are mostly transportation and housing costs, and that you can rent a posh apartment for three to four weeks for the same price as staying in a mediocre hotel for four days, things start to get very, very interesting. You need to amortize the transportation and housing costs over the period of time that you’re in this specific location. So I saved $32,000.

There are some very interesting instances and quite simple approaches for actually making money — and let’s just look at making and saving as essentially the same thing, improving the balance. You can actually improve your financial balance by taking mini-retirements…

Read the whole interview here

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Low-Cost, High-Reward Mini-Retirements: Explore the World with International Volunteering https://tim.blog/2008/04/01/low-cost-high-reward-mini-retirements-explore-the-world-with-international-volunteering/ https://tim.blog/2008/04/01/low-cost-high-reward-mini-retirements-explore-the-world-with-international-volunteering/#comments Tue, 01 Apr 2008 23:42:50 +0000 http://www.fourhourworkweek.com/blog/2008/04/01/low-cost-high-reward-mini-retirements-explore-the-world-with-international-volunteering/ One great method for taking an expenses-paid “mini-retirement”–or adding more time to your travels without adding costs–is to work with an international volunteer organization. Some volunteer groups charge a participation fee, but there are some that will cover your food, housing–and provide you with good meaningful work–at no cost. I would like to share with …

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One great method for taking an expenses-paid “mini-retirement”–or adding more time to your travels without adding costs–is to work with an international volunteer organization.

Some volunteer groups charge a participation fee, but there are some that will cover your food, housing–and provide you with good meaningful work–at no cost. I would like to share with you a few stories from friends who have all taken mini-retirements with Hands On Disaster Response, one such group.

Marc Young, Volunteer

A Little Back Story

Breakdowns of any sort can be great experiences: nervous, communication, etc. They allow us to return to center and to refocus on what it is that truly matters. For Tim, it was a one-way ticket to London in June 2004.

My breakdown came just a few months later and took me to Thailand to find anyone or any place I could help recover from the Tsunami that had just destroyed tens of thousands of homes and lives. I had been living in L.A. working as a freelance designer, treading water and occasionally getting mouthfuls of it, and my adventure to Thailand was a conscious decision to give up treading and to dive down deeper to explore just what was around me…

What was meant to be a one-month trip to volunteer and travel turned into 5 months in Southern Thailand and, ultimately, an international relief organization. It is from this organization that the stories come from below:

Michael Babel – Grad. Student, Licensed Massage Therapist, Life Coach
Michael Babel - Grad. Student, Licensed Massage Therapist, Life Coach
Michael, far right with cast of play he organized in Biloxi, MS.

From Michael:

I first connected with HODR in Biloxi Mississippi after Hurricane Katrina. I was originally volunteering with another group but was looking for something more hands-on, and came upon Hands On a few towns away from where I was working. I arrived at 7:30am and was out cutting trees by 8am; it was love at first sight. I just returned from my 4th project with Hands On and, in spite of the disaster it will imply, I look forward to the next time.

Travel a lot of the time has to do with funds, how much money there is available to sustain one’s traveling habit. HODR helps me travel longer with less funds, allowing me to experience so many amazing moments…

In the Philippines “The realization that if we weren’t there, no one else would be.” In Biloxi “The moment when I realized the streets were clean, things were in piles, our efforts were making some difference.” In Bangladesh “Taking a boat 22 hours down a river, being the only white and English-speaking person on that boat, and being dropped off at a dock at the edge of a jungle.” In Peru “The night we went around the campfire and asked where people were from and there were volunteers from over 30 countries present.” In Bangladesh: “I gave a little boy some colored pencils and he burst into tears and hugged my legs.”

Jeff Johns – Student & Photographer
Jeff Johns - Student & Photographe
Jeff, crouching center with crew of volunteers in St. Domingo, Philippines.

From Jeff:

When I am not chasing HODR around the globe I am a full time Visual Journalism student in Ventura, Calif.

After the Tsunami in 2004, I was looking on the internet for any aid group that was accepting volunteers and that didn’t make it almost impossible to sign up. Hands On was the most impressive and human organization. No applications, no fees, no interviews. Just show up and get to work. It takes a special kind of person to travel to the far ends of the earth to work your butt off with complete strangers, I guess that weeds out the whackjobs. Well, the bad ones… I plan to graduate from Brooks in 2 years and when I do, plan to spend at least the next 5 years disaster hopping with HODR. There is nothing like free life experience!

I arrived in Thailand with a ticket home in 3 weeks. I left 4 months later. I went to Biloxi for just one week. A week after my return home I raised money and roadtripped from L.A. back to Biloxi with my roommate. All other trips I have changed and extended my trips at least by a few hours. With an experience that is human and real, it is almost impossible to tear yourself away, no matter what the living conditions might be or where in the world you are.

The first time, on my first deployment, that I saw a tear on the eye of a woman who just told me we were the answer to her prayers it really hit me. I’m not a religious man, but to realize you might be the answer to someone’s prayers is a powerful thing.

Also, although there is an ever-growing group of volunteers I have worked with before and now consider family, the experience of meeting complete strangers one week and not remembering your life without them a week later is an intense and amazing experience.

While in Bangladesh the bus system shut down for a morning because the driver had been bitten by an unruly passenger. Also, in the Philippines and Bangladesh, taking breaks with sweaty, dirty volunteers to have tea. I mean, there are so many funny and memorable moments with Hands On and there is no way to explain them. They wouldn’t’t seem funny to anyone else. You really have to be there.

Eric Zdenek – World Traveler
Eric Zdenek - World Traveller
Eric, far left with volunteers taking a boat trip on an off day in Thailand.

From Eric:

I make money by helping my bros run a Christmas Light company in LA (Sept thru Jan).

I first got hooked up with HODR when I canceled a 9 month trip to Italy to work with then Hands On Thailand after the Asian Tsunami in 2005.

At the time most of the resources Hands On received went directly to the effort, but for some of the longer term workers, deals were struck for discounted accommodation and meals. In part by being in deserted towns (towns often are after disasters) and by receiving aid from HODR, I was able to comfortably stay in Thailand for just over 4 months.

I have had the opportunity to explore a fair amount of the world considering my slightly unripened age of 25, but nothing I have done or seen even comes close to my experience with the fellow volunteers of HODR. It truly is the most rewarding form of traveling, giving its patrons the opportunity to meet the best of peoples, help others in the worst of times, and leave a village or town better off then when you arrived. I will never forget my time with HODR in Thailand and I look forward to many more opportunities to travel and volunteer with HODR.

Perhaps the single best day of my life occurred while working with HODR on Phi Phi island when a close group of 5 volunteers (Michael, Sunisa, Lizzy) took a day trip to the uninhabited bamboo island for the night. We brought with us some beer, bread, nutella, and a celebration bottle of champagne. Not having enough food for the night, we found dozens of crabs on the beach and chose to grub on them rather than not eat that night. We fell asleep after an amazing sunset and woke up to an even better sunrise. Talk about paradise!

Volunteering Mini-Retirements

If you can afford the travel costs to a HODR project, then all but beer money or personal expenses are covered. We have had hundreds of volunteers extend their travels aboard because they were able to stay with us for another week or month and not increase their costs dramatically. More information can be found on www.HODR.org.

Benefits of International Volunteering:
– Cut Travel Costs
– Be Immersed in a Different Culture
– Meet Fellow World Travelers
– Challenge Your Mind & Body

Here are several other reputable organizations–some may charge participation fees–that offer international volunteering experiences:

Burners Without Borders

Following the 2005 Burning Man event, several participants headed south into the Hurricane Katrina disaster area to help people rebuild their devastated communities. After several months of working along the Gulf Coast, BWB has set up a project in Pisco, Peru to assist with earthquake relief work.

Project HOPE

Nearly 50 years ago, Project HOPE was founded on the willingness of doctors, nurses and other medical volunteers to travel the globe on a floating hospital ship, the SS HOPE, to provide medical care, health education and humanitarian assistance to people in need. While we now operate land-based programs in more than 35 countries, Project HOPE has again returned to sending medical volunteers on board ships around the world to provide medical assistance, long reaching health education programs, vaccinations and humanitarian assistance.

International Relief Teams

International Relief Teams mobilizes volunteers and distributes medical supplies to support the organization’s four missions: 1) domestic and international disaster relief, 2) medical education and training, 3) surgical and clinical outreach, and 4) public health. Since 1988, IRT has provided more than $5.6 million in volunteer services, and more than $112 million in medicines and supplies to families in desperate need in 42 countries worldwide.

Relief International

Relief International is a humanitarian non-profit agency that provides emergency relief, rehabilitation, development assistance, and program services to vulnerable communities worldwide. RI is solely dedicated to reducing human suffering and is non-political and non-sectarian in its mission.

About the Guest Author, Darius A Monsef IV
Darius a ultravagabond in training, creative consultant, entrepreneur (COLOURlovers and others) and co-founder of Hands On Disaster Response.

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