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I had a conversation with a friend the other day.

We were talking about her situation and what her 5 year goals were.

The response: “to be self-employed with a healthy, cashflowing business.”

“What’s stopping you?” I asked.

“My biggest reservation to becoming an entrepreneur is money. Current funds are limited, and I’m not sure the steps I need to take to make money in the beginning. I mean, I get how it’s done in concept, but I don’t know how to get there, and I’m scared of losing everything. [bolded for emphasis]

This is not an uncommon feeling.

So many people understand – at a conceptual level – how business works: sell something for profit (i.e. for more than you paid for it).

Yet the practical steps to get there are confusing. And the thought of “not making it” or “losing it all” is terrifying.

So what is a driven, motivated person to do?

A Better Way to Start a Business

My friend is not alone.

There are plenty of people I talk to every day about business / entrepreneurship and the things holding them back.

Fear of losing your investment – time, money, energy, etc. – is scary enough to cripple us into inaction.

Instead of starting, we wait, hoping a guaranteed solution will fall in our laps.

A couple thoughts:

#1. The guaranteed solution you hope will fall in your lap? Not going to happen. If there were a guarantee, everyone would be a millionaire business owner.

#2. Just because the solution isn’t a guarantee doesn’t mean there’s not a specific process that, if followed, will guarantee you see a return.  And more importantly – it guarantees you won’t lose it all.

What I’m talking about is The Barbell Strategy.

The Fundamentals of Uncertainty and Return on Investment

antifragileI first heard of the Barbell Strategy from Nassim Taleb in his critically acclaimed book: Antifragile.

The Barbell Strategy refers to how Nassim traded stocks when he was a trader.

Most people (retail investors), when they think of investing in stocks, take the “buy and hold” approach. The idea is – stocks always go up over time, so if you buy and hold, you’ll make money.

This is true…

Until it’s not.

Ask anyone heavily invested in the early 2000’s and more recently in 2007.

Bubbles happen and things break.

There are now hundreds of thousands of people without retirement funds nor credit to take out loans.

Yet Nassim was left unscathed from these events.

Actually, he profited.

So what did Nassim do differently?

In his own words (taken from Antifragile – bolded for emphasis):

“What do we mean by barbell? The barbell (a bar with weights on both ends that weight lifters use) is meant to illustrate the idea of a combination of extremes kept separate, with avoidance of the middle. In our context it is not necessarily symmetric: it is just composed of two extremes, with nothing in the center. One can also call it, more technically, a bimodal strategy, as it has two distinct modes rather than a single, central one…”

He goes on to elaborate:

“I initially used the image of the barbell to describe a dual attitude of playing it safe in some areas (robust to negative Black Swans) and taking a lot of small risks in others (open to positive Black Swans), hence achieving antifragility. That is extreme risk aversion on one side and extreme risk loving on the other, rather than just the “medium” or the beastly “moderate” risk attitude that in fact is a sucker game (because medium risks can be subjected to huge measurement errors). But the barbell also results, because of its construction, in the reduction of downside risk—the elimination of the risk of ruin.”

In other words, Nassim specifically avoided the “sucker game” (“moderate” or “medium” risk investments) and instead positioned himself to take advantage of big movements and big swings in the market.

By doing this – avoiding the seemingly safe bet the majority of people take (which, of course, is not safe) – he reduced his downside risk and maximized his upside profit.

Now while this is a brilliant strategy for trading, it’s also an immediately applicable strategy for entrepreneurs.

Entrepreneurship, after all, is by its nature uncertain and full of extreme events.

Surely there’s a way we can apply this technique to our own businesses (whether just starting out or a 20 year veteran in the field).

In the following sections, I’m going to show you how I’ve used The Barbell Strategy as an entrepreneur and ways you can use the same strategy to limit downside and limitless (and of course, profit when it happens).


The Barbell Strategy for Entrepreneurs (or how to guarantee you don’t lose everything when starting a business)

Here’s some conventional business advice:

  1. Pay money to find a market that is underserved.
  2. Pay money to create a product or service that solves the problem of this underserved market.
  3. Pay money for advertising or pump a lot of funds into marketing to get customers
  4. End result: Make more money than you invested (or at least enough to keep operating)

Like “moderate” risk investments, this is the path the majority of people take when starting a business.

Spend money up front to make a return later on.

On paper, it seems like the safe middle ground.

Of course, nothing could be further from the truth.

By investing so heavily in an idea before it’s been validated, we increase our downside exposure.

With every additional dollar we pump into product development, user testing, advertising, whatever, the greater the need for a large return…

And the greater the need for a large return, the greater the chance of not succeeding (and losing it all).

Is it any wonder 80% of new businesses fail in the first couple years?

How to Apply the Barbell Strategy to Your Business

Luckily, there’s another way, and it’s the Barbell Strategy.

This way isn’t easy, and it comes with its share of struggles, but if you follow this approach you can guarantee your business or startup will never go under.

And survival IS the battle when it comes to entrepreneurship.

So here goes:

Step 1. Invest as Little Money Upfront as Possible

Do you need business cards, an office, virtual assistance from Pakistan, or a Hollywood-style filming studio to do your work?

Of course not.

While it’s easy to get tempted to go this route under the auspice that quality matters, the reality is: “quality” (whatever that means) doesn’t matter – the only thing that matters is what people will pay for.

And in most every case, it has nothing to do with the superficial.

I just finished up recording a new episode of The High Speed Low Drag podcast with my friend and co-founder Antonio Centeno. We were talking about business marketing and how his website and YouTube channel that have brought in millions of views.

I’m looking into doing more video production for my company and asked him if he’d been filming all of these videos in his professional film studio.


antonio centeno realmenrealstyle

He just – as in just this past month – built out a professional studio.

Before this – for the past few years – he recorded everything from his house with a basic setup – no crazy lights, or backdrops, or 4k HD 3D cameras.

Just him and his computer and a decent microphone.

Antonio understands at a fundamental level that it is more important to validate an idea before pumping money into it, rather than pump a lot of money into a project hoping the return will be big enough to justify the upfront costs.

Key Take-Away: If you want to survive as an entrepreneur, you must limit your downside exposure – this means investing as little money upfront into unproven initiatives as possible. Once your idea is validated (people pay for it), then you can put money into the expansion and scaling parts of your business.

* * *

Step 2. Maintain a Consistent Revenue Source

You’ve probably heard stories like this before:

Ambitious entrepreneur quits school or their job, jumps 100% into designing MSDOS or whatever with a friend (in a garage) and then becomes a billionaire.

This romanticized story makes it seem like they had no safety net, that they threw caution to the wind and leapt without care.

Of course, if you know the history of most of these founders, they were anything but net-less.

In almost all cases (I’m sure there’s one exception), these people had savings accounts, funds from family, money coming in through a trust fund or welfare or whatever.

They were never completely sink or swim.

The ones who were you probably never heard of because they sank (and because of survivor bias we never hear these stories).

It’s not smart to jump 100% into something that’s not making enough money to support you.

If you do, you increase your risk and downside exposure.

If you take this approach, when the new software you develop goes nowhere, instead of being able to hold out and keep hustling until you hit your tipping point, you have to throw in the towel and get a job.

So what can you do?

  • Have a part time job or side gig (or passive income stream) that brings in enough cash for you to sustain operations indefinitely.

This is different for different people.

For me, it’s about $3,000 per month.

If I can bring that amount of money in every month, I’ll cover my expenses and can keep working on my business, even if my business has a bad month.

These revenue streams don’t even have to be related to your business (and to limit downside risk, probably shouldn’t be).

I’ve written more about that here.

Key Take-Away: If entrepreneurship is survival (and it is), you need to have a consistent revenue stream that allows you to keep operating even when you go through a dry spell in your business. This could be consulting, freelancing, contract work, investments, or a part time gig – whatever it is, it must be able to support your minimal monthly operating expenses, or your chances of survival and success drop dramatically.

* * *

Step 3. Invest Equally into Multiple Projects with Extreme Potential Payouts (The 1/N Technique)

This is where you make your money.

While the first two steps are about limiting downside, step 3 is all about maximizing the upside potential if something hits its mark.

In a prior post, I wrote about the 1/N Technique:

  1. Instigate and ship a lot of products.
  2. Keep your time, effort, and money investment in each equal (or about equal)

Focus too much time, effort, and money into one project (before product/market fit) over another and you increase downside risk and decrease probability of success.

Taking the 1/N step further, the key is to ONLY start projects that have extreme potential payout.

What is extreme potential payout?

It means something that you can build and walk away from and it still makes you money. Ideally lots of money (to make up for the risk involved).

I’ve mentioned my friend (and also co-founder of High Speed Low Drag) John Dumas before.

Recently John shared his July income report – a completely transparent view of his income and expenses.

In July, he brought in$283,353.16.


john dumas eofire

Yes, that’s the real revenue he generated in July.

Yes, he’s that precise with his bookkeeping.

More importantly: the greatest source of his income comes from products that continue to sell themselves without him being there.

Sure, he needs to feed the funnel to keep sales going, but even if he took a week (or a few months) off, he’d still get new sales every day.

The beauty of this: now he can focus his time and attention on creating new revenue streams.

This is what I mean by investing in projects with extreme potential payout.

Key Take-Away: It’s not enough to limit downside risk. You must also expose yourself to the upside, and the best way to do that is to use the 1/N Technique and only take on projects with extreme potential payout.

What You Should Do Next

Is the Barbell Strategy easy to implement?

Of course not – but nothing worthwhile ever is.

It’s also important to realize that this is not a technique for generating tons of money immediately.

Those things never work (or will land you in prison).

The final thing you should take-away after reading this:

It takes time and effort to make this work.

  • Building a business takes lots of time and energy
  • Writing and selling a book takes lots of time and energy
  • Crafting your ideal lifestyle takes lots of time and energy

But if it didn’t, then it wouldn’t be worth it, would it?

So the question is: when will you start?

I hope the answer is today.


Started, finished, and shipped in Renton, WA.

Total writing time: 2:03 hours

Soundtrack: Bastille (what can I say…I don’t just listen to indie music)




From Passion Project to Business

Antonio Diaz of Life and ThymeThere are two words that define the theme of Life & Thyme: culinary storytelling.

Antonio Diaz is the founder of Life & Thyme, a digital publication and production studio devoted to bringing a community together around food.

Antonio and his team bring culinary fanatics the stories behind the food and restaurants they enjoy.

In the past two years, Life & Thyme has grown – and evolved – rapidly.

What started as a local project, featuring LA restaurants and chefs, eventually turned into a global movement, featuring the artists behind food from all over the world.

In today’s broadcast, I talk with Antonio Diaz about what it’s like starting with a passion-based project, how he was able to launch a magazine out of a collection of Instagram photos, and how it all evolved into a full on film production studio.

What Antonio Diaz and I Talk About:

  • Antonio’s background in digital publishing and the birth of Life and Thyme
  • Why you should start simple and worry about the core idea first (not monetization, which comes later)
  • How a passion project Life of Thyme, ended up starting a profitable video production studio
  • The Power of a community and how to build one yourself
  • Why meeting offline is so important to building a passionate group of supporters
  • How to find people to work with /collaborate with and  why it’s impossible to do everything yourself

Wise Words from Antonio Diaz:

Building a community is what matters, not product, or website. A Strong communitycan move mountains.


If you think too hard, you over think and cause more stress. Live in the moment. Some things work out, others don’t. Lighten up. Have a good time.

Where You Can Find Antonio Diaz Online:



* * *

If you enjoyed today’s podcast, please leave a review on iTunes here. Thanks so much in advance for your support.


This post is all about how I made money while working and traveling around the world.

Because information is useless without application, here’s a free bonus: “Work + Travel Abroad Toolkit” that includes budget trackers, expense trackers, and more (with more resources to be added in the future), to help you become a nomad entrepreneur (or nomadtrepreneur…?). Get the bonus here if you want it.


traveling and working abroadIn the past twelve month, I’ve:

  1. Traveled to 5 continents
  2. Spent time in 12 countries
  3. Literally lived out of a car for two months in New Zealand
  4. Almost got stomped by an elephant in Africa
  5. Snorkeled the Great Barrier Reef
  6. Driven through the deserts of Namibia to find cave man paintings (found them!)
  7. Had way too many doble espresso con crema’s in Argentina
  8. Canoed around the Amazon
  9. And a lot of other crazy stuff (that’s been documented) but for the sake of brevity, let’s move on…

In that time, I’ve also run into a lot of travelers.

Inevitably, after hearing how long my wife and I have been traveling or how long we plan to continue traveling, we get the following question:


People want to know how we do it.

Or rather: they want to know how we pay for it.

What they’re usually after – and I know this from experience – is a simple answer they’ve heard before:

  • “I sold all my stuff and I’m going in debt to finance this…” or…
  • “I was born into a trust fund…” or…
  • “I work on an oil rig for a year at a time and then use my off time to travel around the world…”

An answer like this is easy to understand and allows us to label it and file it neatly away in our brain-boxes.

Which, of course, is a problem for us when it comes to explaining what we do and how we do it…

The majority of people you meet traveling fall into one of two categories:

  1. Vacationer (single, couples or families; 1 – 4 weeks at one or two destinations; often spent at resorts)
  2. Backpacker (mostly European, college level people that are usually broke or at least act like it, and carry a backpack or three from hostel to hostel around the world)

Here’s the problem…

While we technically went abroad after getting married, the fact that we’ve been traveling for about a year means the term honeymoon probably isn’t appropriate (although that won’t stop us from calling it this).

And while we did carry a ridiculous number of backpacks around the world with us, we’re not broke or European, so the classic backpacker designation isn’t quite accurate.

But most importantly:

Neither of these two categories allows room for “working” to be part of the travel equation.

(sure, some backpackers will find work at coop farms when they find themselves broke in a foreign country, but it’s usually work for a few weeks then move on kind of stuff…or start working and never leave…but never working at the same time as you travel)

The idea of working WHILE you travel, completely by choice (as in, not being paid by National Geographic to take pictures of Elephant balls), is a foreign concept to just about everyone in the world.

In fact, on more than one occasion I received really weird comments if people saw me working at my computer daily. This would be AFTER I tried to explain what I do…

Which is why I don’t try to explain what I do at all anymore.

Too complex and most people don’t really care.


Some people who read my blog or books and know I travel while I work HAVE asked the question, legitimately, and want specifics.

So here are answers to questions I’ve been asked at one point or another (with probably more details than you want…deal with it).

Hope you enjoy it.

p.s. I created a “Work + Travel Abroad Toolkit” for weirdos like me who enjoy traveling wherever they want in the world while working simultaneously to pay for said travel. You can grab it here.

How do you afford to travel around the world for a year?

This is a loaded question, but here goes.

The way I’m capable of traveling around the world is through an elaborate three-pronged campaign:

  1. Savings
  2. Passive Income
  3. Create New Revenue Streams

Brilliant, right?

Okay, so let’s get more detailed:

How to Save Money So You Can Travel Around the World

Step 1: get a job

Step 2: don’t blow all your money on cocaine

Step 3: save 10 – 40% of every check you make (as a single officer in the Army, saving 40% wasn’t that hard; but 10%, no matter how crunched, is always possible. Simply look where you can reduce – cellphones, tv, and Starbucks are not essential)

I didn’t really have a dollar amount I wanted to save before I started traveling, but I figured the higher the better.

At a minimum, if you want to come away debt free, try to save $100 per day you intend to spend traveling (100 days = $10,000).

There’s no scientific reason for this, except that we wanted to keep our budget to $100 per day and were actually able to do this (more on this later).

How to Create Passive Income so You Can Travel the World

Passive income doesn’t really exist online, but it does exist offline…in the real world.

What I mean is:

  1. Investments
  2. Real estate

A lot of people get turned off by the seeming complexity of stock investing and real estate investing, and so they do what the plutocratic-industrial complex tells them to do – invest in mutual funds and maybe bonds or CDs if you want to be really safe, and for homes: buy the house you live in because it will go up in value over time.

If you want to follow that advice, go for it.

For me though, I like to do the opposite of what the majority of people do (which is always fragile), so I focused on stock option trading and rental properties (antifragile and robust investments).

Now, every month as I’m traveling, I make extra income from my rental properties, which have full time managers. I spend about 30 minutes a month managing the managers on average.

If you want more info on these kind of investments, I’m not certified in anything except being a badass, so you should still ask a certified professional something or other.

Alternatively, do your own education:

  1. Rich Dad, Poor Dad (basic but good)
  2. The Creature from Jekyll Island (not for the weak-willed)
  3. The Black Swan (the book, not the movie)

How to Create New Revenue Streams While Living and Traveling Abroad

Okay, so this is the meat-n-potatoes of what I do.

The passive income is good and the savings help, but the reality is: I wouldn’t be able to afford what I’m doing if that was all I had.

The key for me has been to create new revenue streams as I travel.

Remember all the braggadocios things I mentioned at the beginning of this article? That’s not all I’ve done the past 12 months. I’ve also:

  1. Started a publishing company (Insurgent Publishing) and launched several books and products
  2. Launched a semi-annual business publication (Bootstrapped)
  3. Wrote and published The Complete Guide to Pay What You Want Pricing (and a dozen other mini-guides)
  4. Colaunched The Flight Formula (online and offline business incubator program)
  5. Colaunched High Speed Low Drag (a veterans mastermind, training platform, and exclusive community)
  6. Consulted
  7. Freelanced
  8. And done a bunch of other experiments to generate cashflow

This list doesn’t include all the failed projects and attempts that never got off the ground.

The point is: creation is a hustle.

To create new revenue streams takes time and effort – but if you enjoy creative work, it’s an absolute blast (I seriously love working as much as I love traveling, which is weird according to a lot of people).

As far as practical ways to get started on this…you’re reading this blog, right?

Alternatively, I’m creating an eCourse to show people how to start, finish, and ship collaborative projects.

Why collaboration? Because most of us don’t have all the skillsets we need to launch something successfully, so the real entrepreneur connects with and leans into talented people to make a project successful.

If you want access to the course, you can sign up here.

Track Everything

What you track you improve.

Whether it’s weight loss, habit change, or business – the things we measure are the things we’re able to change for the better.

When you start your around the world travels, you’re going to want to start tracking your finances.

Here’s what our tracker looked like:


budget recorder

It’s a simple google spreadsheet that we update every time we made a purchase. This gave us insight into how much we were spending so we could stay under our limit (under $100 on average).

If you’d like a copy of the spreadsheet for your own use, grab it here.

Bonus Q and A: Questions and Answers for People who Want to Work + Travel Abroad

The following are a bunch of questions I’ve gotten from people, so figured I’d share my answers with all of you who are interested.

If you have your own questions, leave one in the comments and I’ll answer.


Do you access your American bank accounts online?

Yes. I have multiple bank accounts and I access them all online from anywhere in the world. Just in case, it helps to let them know where you’ll be and when so they don’t lock you out (which has happened to me).

Life Hack: download a program like LastPass to manage all your passwords (I have a few hundred passwords and LastPass saves me a ridiculous amount of time every day logging into things)

Do you need a special debit/credit card when you travel?

No, but it might help. I use USAA and they have very small international fees (about 1% or less versus BoA which is like 3%), so I just stick with that. However, I’ve heard of great international cards that could probably help you rack up miles or points…

I was thinking of getting the top card listed here; would that be wise?

Yes. I’m going to be doing something similar the next time we travel to SE Asia so I can fly international for free (I have over 100,000 miles, but it doesn’t hurt to get more and possibly upgrade).

Do you simply pay whatever bills you have online while abroad?

Yes. This works 99% of the time. Worst case scenario, I ask people at home that I trust to help me out (although I can’t think of a time this has been necessary).

When you make money, is it going into American accounts? If so, does that mean tax season is same as it always is or do you have to make particular changes since you were traveling?

Yes, all American accounts. Since I was only outside the country for less than half the year, all income earned abroad is still taxed by the United States (one of the major bummers of being a US citizen, since few other countries do this). I run my business through an LLC so everything is taxed as individual income, so whatever my bracket would normally be – that’s what I pay (the bonus being I can use income from my business to pay business expenses, which could potentially knock me down a tax bracket…another reason everyone should own a business).

Do you have to have a certain type of visa to travel and work?

Nope. I don’t specifically enter any country to do business, persa (although I do work as I go, and I’ve presented at conferences, seminars, etc.). I suppose this would be something worth checking on if you’re planning to get an actual part time / fulltime job while you visit a country. For example, my wife teaches yoga, and in most countries she needs a work permit to teach (although some countries are much more relaxed than others).

Any good sites for finding the safe areas and hostels to stay at? Or other safe housing?

HostelWorld.com + AirBnB.com are great resources. We also Google the areas to find out if there’s anything crazy going on and if you want to get real detailed, the US govt. has a website that can fill you in on all the potential terrorist threats around the world (if you want to be prepared Liam-Nieson-Taken-style).

Do you carry a weapon when traveling?

Just my fisticuffs. We haven’t had any issues or any close calls. We’ve been to some ‘sketchy’ areas too like Johannesburg, South Africa, as well as all over Indonesia, but we’ve never had a problem. Everyone warned us about S. Africa, so we just made sure we didn’t wander back alleys at night and we ended up okay. I’d say most threats are exaggerated – but we also try to use common sense when traveling (again, don’t travel down back alleys at night, don’t get blackout drunk at new locations, travel in groups if you can, etc.).

Any Questions?

Alright, so that’s all I can think of right now.

If you have any additional questions you’d like answered, leave a comment below.

Oh, and if you’d like a toolkit that includes expense trackers, a google document to budget track, and additional stuff as I fill it, get access to the Work + Travel Abroad Toolkit here:


Optin Bonus Button - Travel and Work Abroad Toolkit