My Story

I left my first and last corporate office job behind in 2007. Since then I’ve lived in and worked from more than 50 countries around the world. Along the way, I’ve taken a few businesses from “idea-on-a-napkin” to the first $1,000,000 and beyond. 

In that time I’ve had my share of adventures too — climbing mountains above Machu Picchu, sleeping under the stars in the Sahara, horsebacking riding and exploring glaciers in Patagonia, and skiing in Slovakia, Japan, Argentina, Canada, India, and a shopping mall in Dubai.

I’ve haggled my way through markets from Hanoi to Marrakech, stayed up all night singing karaoke in Tokyo, surfed my first wave in Bali, swam with wild dolphins in Hawaii, and partied my way from Miami Beach to Moscow, and under the full moon in Thailand.

But it wasn’t always like this… 

Compressing over a decade of life into a two sentence highlight reel makes it all sound very exciting, but that’s hardly the whole story.

I grew up in the suburbs, sucked at all the sports, and spent most of my time sitting on the sofa.

I never went on any crazy adventures as a kid.

I wasn’t a Boy Scout. I didn’t learn how to tie all those knots or start fires from two twigs. The one and only sleep-away summer camp I went to was training to become a school safety patrol officer (nerd alert!).

I wasn’t the most popular kid in school. I didn’t even kiss a girl until my third year of university.

In other words, my childhood was safe, comfortable, and boring. 

So, how did I end up here? 

My parents both immigrated to America, but from two totally different countries on opposite sides of the world. For me, that meant growing up immersed in three different cultures.

There wasn’t always one default way of doing things. Instead, I saw multiple approaches, each with pros and cons to be considered and debated. Dinner at six o’clock or nine o’clock? 

Perhaps that’s what led to me constantly questioning everything. I can’t help it. I’m hardwired to look for alternative options and ways to bend the rules.

Does it have to be that way? What if I did it differently?

One of my earliest memories is from a preschool art class. We were supposed to be learning how to color neatly within the lines.

The teacher said something like, “it will look much nicer if you make all of your strokes in the same direction, rather than scribbling in all different directions.” 

She demonstrated the proper technique, then we were each handed a piece of paper and a crayon to give it a shot. I reasoned that, while I could try what the teacher suggested, I could also try coloring in one direction, then rotating the piece of paper and coloring in a different direction, and it should have the same effect… 

It didn’t work.

My drawing turned out messier than the others and the teacher spotted that I hadn’t followed the instructions. I still thought it was a good idea.

At least it was my idea. 

Hacking School

As much as I love learning, I was always bored at school. Too much sitting. Too slow. I think most of the other kids who felt the same way ended up being diagnosed with ADHD and prescribed Ritalin. My parents took a different approach. 

They tried to convince my conservative, Episcopal, private school to let me skip one grade ahead. 

“No way. It’s against school policy”.

At the end of the term I switched to the local public school. After a few months they let me skip ahead from second to third grade. Suddenly I was the new kid, and one of the youngest. My classes were also much bigger and more diverse. 

I felt like a total outsider. All the other kids seemed to understand something that I didn’t — some unspoken set of social rules. I’m still trying to work them out. 

Social awkwardness aside, I stuck with the public school system through middle and high school. Then, in my junior year, my classmate Adam casually mentioned that he was going to graduate at the end of that term, a full year ahead of schedule. I was incredulous.


Adam discovered that, technically, you didn’t have to go to high school for a set number of years.  Instead, you just needed to earn enough course credits and reach a certain level of math, science, and English in order to graduate.

No one had ever mentioned this before. It was just understood, like some kind of law of the universe, that you had to go to high school for four years to graduate (assuming you didn’t fail any classes). 

Once I got my hands on the official requirements and compared them against my coursework, I discovered that Adam was right. And more importantly, I was on track to meet all the requirements by the end of my third year. Except for one…

We were required to have four years worth of English in order to graduate. But there was no way for me to take an extra English class. The term had already started, and besides there was no room in my schedule — I needed all of the courses I was already taking in order to graduate.

That one class was the only thing standing between me and being done with school forever! I was determined to find a way…

Then I discovered that another local school offered classes at night, typically for students who had failed and needed to repeat a class. But since it was part of the same school system, I could take the one English class I needed to graduate there and it would meet the requirement.

I promptly enrolled (and avoided telling any of the other students why I was really there). A few months later, I graduated at sixteen years old, having skipped the 2nd and 12th grades.

Childhood Dreams

Some kids follow their passion from childhood into adulthood and go off to save the whales, become pro surfers, or chase stardom in Hollywood.

Not me. 

I had all the usual aspirations as a little kid. I wanted to be GI Joe, James Bond, Bo Jackson, and Michael Jackson all at once. And my parents always encouraged me…

Still to this day I could call my mom and tell her, “I’m going to fly to Mars”. She’d probably tell me, “Wear a hat so you don’t catch a cold!” But she would never tell me, “No you can’t. That’s impossible.” or “Mars?! Who do you think you are?”

As an adult, I realize now that having parents who believe in you is the ultimate form of privilege. As a kid, I never knew anything different.

…but even with supportive parents, dreams of becoming a professional athlete or some kind of performer were just dreams. I never saw a path to make them reality.

Instead, I always just sort of assumed that I would go into business.

My dad at one of his restaurants.

My dad owned his own business. His dad too. It’s the Mehra way. My dad owned a lot of businesses actually  — some more successful than others. If one went bust, he simply started another. Going back to work for someone else was never on the table.

Looking back now, I can see that I’ve been following the same pattern since I was a little kid. 

Unlike the kids in the movies, I never delivered newspapers by bicycle. I owned the newspaper (printed each issue in my room and sold subscriptions to my parents). 

One issue of my newspaper included a survey. My sister commented, “Very good paper, but don’t charge for it ’cause you get to make it free. no production cost = no revenue.”

I responded, “no production cost = more profit, we are not a non-profit organization” (the “we” here is a royal we, referring to eight or nine year old me).

My sister and I grew up reading mystery books and comics. She favored Cam Janssen. Tintin was my hero. We both loved Scooby Doo  — so we did the obvious thing. We started a detective agency together.

We recruited one of our neighbors, made ourselves little ID badges, and went around announcing our sleuthing services.

Much to our disappointment, we soon discovered that there was a distinct lack of unsolved mysteries in our quiet, upscale, suburban neighborhood.

Oh well, on to the next idea…

Entrepreneurial kids in the movies usually also have lemonade stands.

“Ice cold Lemonade! Only 25 cents a cup!”

I took a different route. I hawked bottles of water for two bucks a piece, undercutting the official concession stands at the golf tournament in my hometown every summer.

I could make a few hundred dollars in just a couple of days (back when the minimum wage was less than $5 / hour). It was like Christmas in July.

By the time I was a teenager in high school, I joined a few friends to form Sonic Boom Acoustics. We tried to sell subwoofer boxes to our fellow students in the parking lot of the local mall.

Our sales pitch? Speakers so loud that you could set off other cars’ alarms with just your music as you drove by (we were more than happy to demonstrate).

We even entered local “bass competitions” where they would measure just how many decibels you could crank out. I wonder what the prize was… Deafness?

Around the same time, I got my very first PC. I taught myself HTML and started making websites on geocities. Basic, personal homepages where I could share photos of my favorite rappers and gifs of Homer Simpson. 

Geocities, home of my first websites.

Then came the dotcom boom.

Moving the Market

In the late 90’s, the stock market went crazy for tech. I watched in awe as the founders of companies like Amazon, eBay, and Google were catapulted from tinkering in their garages to becoming millionaires and billionaires seemingly overnight.

I was so obsessed with tech and startups that for my sixteenth birthday, my mom took me to the COMDEX conference in Las Vegas.

I was a giddy teenager among a few thousand businessmen and women. Bill Gates gave the opening keynote. Eric Schmidt, then CEO of Novell (later Google), gave another.

But the highlight for me was meeting Linus Torvalds, the original developer of Linux.

Front cover and Yahoo! ad from the COMDEX ’99 program. The ad reads, “With over 3.5 million website, it’s a jungle out there. But for over 4 million surfers, we’re the guide they turn to…”

Not content to sit on the sidelines while “everyone else” was getting rich, my friends and I wanted in on the action too.

Fortunately, unlike becoming a famous football player or a Hollywood star, making websites was something I actually knew how to do.

One of the first websites we built together was StockLizard. The concept, which we copied from some other site, was to “profile” (aka pump up) penny stocks.

We chose the stocks carefully based on price and typical trade volume (both needed to be low enough), but the profiles themselves were just basic information about the company and the industry that we gathered from public sources.

We were always very careful to disclaim that we were “not offering investment advice” and we made sure not to say “you should buy this stock” or anything like that.

Of course, that’s exactly what we hoped people would do.

If enough people did, the stocks would go up. For that to happen, first we had to build a big audience and generate as much hype as possible.

I spent countless hours posting on the Raging Bull message boards, encouraging everyone to subscribe to our email list, so they would be the first to know when we release a new stock profile.

A couple of decades before Wall Street Bets and meme stonks, there was Raging Bull.

I would lock myself in my photography teacher’s office (home to one of the only computers in my high school building with an open internet connection back then), so I could work on StockLizard during school.

Every time we released a new profile, we would get so much traffic that our website would crash. But it didn’t matter. The stocks went up! And each success built more hype for the next profile.

I didn’t have any money to invest, let alone a brokerage account, so I couldn’t buy the stocks myself, but plenty of other people did.

One stock we profiled shot up 733% in a few hours!

Our success at moving the market didn’t go unnoticed. On the day we were scheduled to release our next profile, we got a phone call from the friendly folks at the U.S. Securities and Exchange Commission (SEC). They were “just gathering some information” but we got the message.

A few weeks later the dotcom bubble burst and the era of “irrational exuberance” ended. StockLizard was dead, but my dreams of dotcom riches were anything but.


I graduated high school the following month and headed off to George Mason University.

I had mixed feelings about going. At sixteen years old, moving out of my parents’ house and into a dorm felt like freedom. Signing up for four more years of school did not. 

I enrolled as a Computer Science major. I never even consider any other options. I’d already been studying programming for two years in high school (C++ and Pascal), in addition to the HTML and Perl I learned on my own for building websites.

I even managed to get college credit for my high school computer science coursework. Sadly, that meant that I couldn’t take any computer science classes at GMU for at least a year.

My high school credits covered the intro courses and I wasn’t eligible yet for the more advanced ones. Instead I was stuck taking boring “gen ed” courses. Very demotivating. 

On the plus side, living in a dorm on campus meant that I had a hardwired, high speed internet connection in my room!

I took full advantage.

I hosted servers under my bed, and my desktop was always on. The internet, as it turns out, was a lot more interesting than going to class. 

I ended up failing four out of my five courses the first semester. Whoa. I’d never gotten below a C before that.

It didn’t help that I was still only sixteen years old and living away from home for the first time. Unlike many of my freshman peers, I knew how to do my own laundry. What I lacked was the discipline to wake up on time and get to class without my parents watching over my shoulder.

The other problem was that I had practically zero interest in the actual education. The only reason I was even there was to get a piece of paper that would make my parents and any future employers happy.

I already knew what I wanted to do. And I didn’t need a degree to do it.

My friend Poya (co-founder of SonicBoom Acoustics and StockLizard) and I continued building new websites together, still hoping to strike gold.

In 2001, we launched PicCritic, a competitor to the popular site HotorNot where people could rate each other’s photos based on attractiveness. 

Here’s a screenshot of PicCritic I grabbed from the WayBack Machine archive.

PicCritic was something of a hit, but as traffic grew, so did the costs of maintaining it. In those days, running a website, especially a popular one, wasn’t cheap. And we were broke students with no access to venture capital, angel investors, or any other source of funds beyond our credit cards.

We tried to monetize the site with ads, but at that time (after the bubble burst, but before Google AdSense came along) it was tough.

After a year or so we made the difficult decision to shut down PicCritic, because it wasn’t making any money and we couldn’t afford to keep it running.

My dotcom dreams were taking their time to come true…

0.19 days of vacation

I got my first summer job when I was 13. If LinkedIn existed back then, I probably would’ve called that job “Marketing Associate in the Food Service Industry”.

In reality, I was walking from door to door handing out flyers for Domino’s pizza. I wasn’t even old enough to work legally, so I got paid cash under the table. It helped that my best friend’s brother was the manager. 

I continued working odd jobs every summer break while I was a student. Restaurant host. Marketing intern for a defense contractor. Arcade game technician at Dave and Buster’s. 

Then, at 17 years old, after my first year of university, I landed a summer internship in the I.T. department of Congressional Quarterly, a prestigious publishing company in Washington, DC. I was assigned to my very first cubicle (actually, it wasn’t even my cubicle, I had to share that little cubicle with a couple of other people).

I had planned to finish the internship at the end of the summer and go back to university, but my coworker took me aside one day to tell me that the company was growing and they needed help. He asked me to stay on and keep working there after the internship ended. 

I hesitated. My parents wanted me to focus on school, but at 17 years old, the 17 dollars an hour I was earning felt like big money.  

We compromised. I went back to school in the fall, but continued working part-time. Eventually, my boss persuaded me to take a full-time job with a salary and benefits, even though I was still a student (and still a teenager). 

In my first year as an employee, I got one week of vacation… that’s five days off over an entire year. They didn’t even give me all of the days at once, I had to earn them throughout the year (at a rate of 0.19 vacation days for every biweekly pay period).  

It wasn’t just me. That was the standard policy. Somehow most of my coworkers seemed to be okay with the situation. Many of them didn’t even use all of their allotted vacation days! If they did take time off, they usually just drove to the local beach for a few days.

Not me.

I squeezed every second out of those precious vacation days to fulfill my teenage dream of backpacking around Europe with a rail pass. Of course, five days isn’t nearly enough time for a trip like that.

Fortunately, I had worked so hard, including nights and weekends — I even slept on the floor of that little cubicle — that I’d earned some extra “comp time”. I think I managed to take off about two weeks in total. I went to Belfast, Amsterdam, and Paris by myself, and then met up with my friend Brent for Dusseldorf and Berlin.

Looking back, I probably spent more time on the train going from city to city than I did in any one place! That first trip seems so ridiculous and rushed to me now…

(These days when I travel, I like to spend months at a time methodically exploring a single city or region, so that I can get off the tourist trail and try to feel what it’s like to actually live there.)

…but at the time, that trip was the highlight of my life!

I was 18 years old and traveling abroad for the first time without my parents. As soon as I got back home, I couldn’t wait to travel again!

I spent the next year working (and still going to university) so I could earn money and a few more of those precious vacation days for another trip.

The following summer, I went straight back to Europe and did it all over again. I even visited a bunch of the same cities, only this time, I was flying solo for the whole trip.

Nobody else I knew wanted to travel like I did.

Me trying to look cool on one of those trips to Europe.

My friends were all too busy studying or climbing the corporate ladder.

And the people at work seemed totally fine spending most of their waking hours, during the prime years of their lives, sitting in the office (or stuck in traffic commuting). Even when they weren’t working, they hung out near the office and went to happy hours together.

Not me.

I wanted to explore the world!

But at this pace of working for an entire year, traveling for a week or two, working for another year… it was going to take forever. 

While traveling I’d met some people who managed to save a bit of money and taken a year off from work or school (unheard of in America), so that they could go travel the world. 

One guy in particular stands out in my memory.

Flying Carpet Man 

I was staying at a youth hostel in Liverpool on one of those trips to Europe. I arrived and checked in sometime in the afternoon. When I went to the room and turned on the light, I was startled.

Some guy was already sleeping there. I knew it was a shared room, but I didn’t expect anyone to be there since it was the middle of the day.

He woke up from the light and the noise of me stumbling in and putting my bag down. He looked upset. I was a teenager at the time and he was older. Maybe 40?

I made a feeble attempt at conversation to ease the tension, “So, what brings you to Liverpool…”

He got up.

Walked to the window.

Pointed outside, and said in heavily accented English, “my car.” 

Once we overcame the initial awkwardness and the language barrier, he explained to me that he had sold his carpet business back home and was traveling the world and living on the proceeds.

He had no set itinerary and no return date. He would travel as much of the world as he could for as long as he could afford to. Maybe a year? More?

My mind was blown. What a way to live!

“…but there’s no way I could do that”, I told myself. “I don’t have any savings. I’m in debt.”

That was true, but I hadn’t even bothered calculating what it would actually cost. The thing that was really holding me back wasn’t money.

It was the idea in my mind that before you could go off and enjoy life, first you had to “make it”.

In my early 20’s, looking like I’m about to give you a really bad deal on a used car.

A Wake Up Call

In 2004, one of my friends casually mentioned that, “Nothing wakes me up like a ringing phone”.

A lightbulb went off. 

Poya and I did a little research and discovered that there was one website that let you schedule wake up calls online. It seemed like they were making money, but their web interface was really bad. We knew we could do better.

There was one problem: it was very difficult to do any kind of phone call automation or programming. There was no cloud computing, Amazon AWS, Twilio, or other API’s that you could build on top of back then.

Instead, you needed to buy special IBM modem boards, put them in a server, and then co-locate the server in a telecom company’s data center. It was very cost-prohibitive and not scalable at all.

Just as we were trying to figure all of this out, another friend introduced us to Asterisk. Asterisk is an open-source PBX, a piece of free software that takes the place of thousands of dollars worth of phone system hardware. Exactly what we needed.

The three of us flew to Atlanta to attend the first Astricon conference, where Asterisk 1.0 was officially released.

Snoozester team at Astricon, together with Mark Spencer, the lead developer of Asterisk. September, 2004.

Within a few months we’d built Snoozester, a website where users could enter their phone number and request a scheduled wake up call (this was still a few years before the iPhone, when few people had smartphones and most still used traditional alarm clocks).

At the time, we called Snoozester a free “beta” service (that was the cool thing to do – remember when every Google service was in beta?).

An early version of the Snoozester homepage

By then we had already learned that, unlike the famous quote from Field of Dreams, “if you build it, they will not come”. Not unless you get the word out. So we wrote and shared press releases, posted on message boards, and even printed and handed out little cards to promote Snoozester.

Most of all, we made sure that anytime someone searched Google, Yahoo, or MSN for a keyword related to wake up calls or waking up on time, that they would find us. 

The “beta” period lasted for a year or so. In that time, a few thousand people signed up and we delivered 20,000 wake up calls.

That was enough validation for us to start charging for the service. Plus, having revenue meant that we could cover our costs of running the website and avoid the fate of PicCritic.

We knew wake up calls were probably not going to be “the next big thing”, but we still thought that we’d built something pretty impressive from a technology and user experience perspective. 

And Snoozester was a novel enough idea that we managed to get some media coverage in print and on TV.

A later version of the Snoozester homepage

Besides, wake up calls were just step one. Eventually we hoped to build an entire suite of scheduling and notifications services, including automated appointment reminders, calendar integration, and a comparison scheduling marketplace. 

The marketplace was my “grand vision” — a website where you would be able to say “I want a haircut (or a dentist appointment, an oil change, etc) at 1:00 PM next Tuesday. Who’s available?”

But building all of that was going to take a lot of work and a long time. Especially since we all had full-time jobs, and I was still going to university. Realistically, we each only had a few hours a week to work on Snoozester.

Our solution was to try to raise venture capital. We figured that, with a few million dollars, we’d be able to quit our jobs, hire a few more people, and build all those other features.

Instead of focusing on making the site that we had better, I spent most of my (already limited) Snoozester time on writing cold pitch emails to silicon valley VC firms (from our home office in suburban Maryland). I don’t think any of them ever responded, let alone funded us.

Naughty Nurses

We also started getting inquiries from businesses who wanted to know if they could use our technology. One of the first projects was a marketing campaign for Axe (the body spray made by Unilever).

They were launching a new shower gel, and their marketing agency had this idea for a campaign.

Teams of Axe’s “naughty nurses” would go out to nightclubs in big cities around the United States. They would offer wake up calls to help guys who were out partying and would probably be hung over in the morning.

The concept fit well with the positioning for the shower gel. It was called “Axe Recovery” and claimed it would “wash away your hangover”.

The campaign also fit well with Snoozester, since we were in the business of delivering wake up calls, so we already had the technology to make this happen. The campaign was a hit and it ended up winning a couple of awards.

The same marketing agency started pitching similar campaigns “powered by Snoozester” to their other clients. 

Unlike our consumer-facing wake up call service, where each customer paid us a few dollars per month, our business engagements generated thousands or tens of thousands of dollars each.

Eager to take advantage of the opportunity, we created a separate marketing website to promote Snoozester’s Business Services. Over the next few years, we collaborated on marketing campaigns for Body by Milk, Bustelo Cool coffee, and the Chicago Sun-Times newspaper, among others.

Busy as we were, Snoozester was technically still just a side project. I used to spend lunch breaks from my office job in the hotel across the street, taking calls with Snoozester business clients. 

It was becoming impossible to keep up.

After we launched Snoozester I had already switched from being a full-time student to a part-time student. Then I just stopped registering for classes altogether.

Our revenue was growing, but not very quickly. And our attempts to raise capital were still going nowhere.

We knew that if we wanted to take Snoozester to the next level, that we were going to have to devote even more time to it than we had been.

We made a deal to borrow some money to cover our personal expenses while we worked on growing the business and raising capital. 

In November 2007 we quit our jobs to go all in on Snoozester.

Freedom (Not Really)

Most people associate quitting your job to “be your own boss” with having more freedom.

In my case, it was the opposite.

Instead of a job and a boss, I had a company to run and clients to serve. I was even more tied down than before.

The fact that we were running on borrowed money — money that was going to run out soon, and that we needed to be able to pay back somehow — created a lot of pressure for us to work hard.

And just to make sure, we copied the restrictive vacation and “track every hour” policies from our old jobs. We even programmed our own custom timesheet system. 

Looking back, it seems like we spent our time on everything other than improving the core Snoozester service.

Part of the problem was that neither of us really believed in wake up calls as a serious, long-term business. We had built Snoozester on a whim, to solve a problem that neither of us had.

In spite of the fact that we owned a wake up call service, we used the built-in alarms on our phones to wake up (that was about to become a lot more common).

By the time we’d quit our jobs in 2007, the first iPhone had just been released.

This lack of faith in the business we were in left us vulnerable to every possible distraction.


When we quit our jobs to focus on Snoozester, something unexpected happened. 

We started getting offers for freelance work from our former bosses and colleagues as well as other people in our personal networks who’d heard that we’d started our own company. 

But they weren’t looking for wake up calls or anything else remotely related to Snoozester.

They needed new websites, help with, or setting up an email server. This was all stuff that we knew how to do, but we hadn’t set out to build a consulting company.

We took the work anyway, because it meant that we were able to keep the lights on, pay back the loan ahead of schedule, and start paying ourselves salaries.

When it came time to get paid for our consulting work, we felt pretty silly sending an invoice for I.T. services to a corporate client that said, “Snoozester” across the top. 

So we rearranged the letters in our own names and came up with “Nampora”. We put together a quick logo in Photoshop and registered Nampora as a trade name of Snoozester.

The original Nampora logo

To recap — we’d quit our jobs so we would have more time to focus on Snoozester, but we were now splitting our time between: keeping the original wake up call service going, providing Snoozester services to businesses, trying to raise capital so that we could finally develop our grand vision (the comparison scheduling marketplace), and doing random I.T. consulting projects for our Nampora clients.

Needless to say, we didn’t make major progress in any one area. Instead, we were moving one inch in a dozen different directions at once. And it got worse over time.

Whenever we landed a client in a new industry or did a new type of project, we thought, “what if this is the market we should be focused on?”

After High Point University approached us to provide wake up calls for their students as a fun perk, we launched “Snoozester Edu” in hopes of attracting more university clients.

We made (yet another) website, created marketing materials, hired a sales rep, and started attending and exhibiting at trade shows for student affairs professionals.

The same thing happened when the Chicago Sun-Times newspaper asked us to help them run a phone-call-based sweepstakes to drive single copy sales. The promotion was a big hit, and we did many more of them together over the next few years.

We figured, if this works so well for one newspaper, why not others? We bought lists of leads of newspaper executives and started cold calling.

We landed a few clients like this, but the return on our investment, time, and effort spent was pretty low. It didn’t help that newspapers were a dying industry. Most were looking for ways to cut costs, not take on new vendors and services. 

Universities had money to spend, but the sales cycle took years. Besides, most laughed at the idea of providing wake up calls for their students. I can’t blame them.

These are just two of the markets that we pursued. There were many others.

I’m pretty sure I still have a couple of cases of mugs in storage somewhere that we made for promoting “Nampora Dental”, our marketing service for dentists.

Oh, and then there was Rockville AC, our online lead generation service for local air conditioning repair companies. And before that, Frank Networks, a scheme for selling our excess phone system capacity as an alternative to scammy phone cards for making cheaper international calls.

My typical work day would include responding to inbound sales emails for Snoozester services, meeting with a Nampora client to go over requirements for a new website, fielding a concerned call from a dentist and reassuring him that we were on track to deliver the promised number of new patient inquiries, troubleshooting a SalesForce bug for an academic publisher, checking stats on one of our Google ad campaigns and adjusting bids, filing some nonsense paperwork with the local government, researching available domain names for whatever new idea that we’d just come up with, and then taking a break for lunch…

It’s easy to look back now and say that this wasn’t the right approach, that we were spreading ourselves too thin, but for a long time, it felt like the only option.

No one line of business that we were in was consistently generating enough money to cover our costs. And we lived in fear that demand for wake up calls would dry up any day now. 

So, for five years, we continued doing this combination of running a wake up call service, cranking out client projects, and soul-searching-as-a-business.

Frustration mounted.

In spite of having quit our previous jobs (and given up benefits like employer-provided health insurance, annual raises and bonuses, and retirement fund contributions), we weren’t much closer to “making it”. 

In some ways, it felt like we were getting further away.

We’d stopped trying to raise capital. We weren’t working towards our grand vision for the comparison scheduling marketplace. There was no longer a light at the end of the tunnel.

What if we never “made it”?

A Foregone Conclusion

Ever since those first trips backpacking in Europe as a teenager, I felt like I had an unfinished quest to see the world.

Sure, I’d traveled more since then. I even managed to build up a little travel streak — spending at least some time out of the country every single year since 2000 (still going strong). That’s more than most people.

But it wasn’t enough. 

I was craving the kind of adventure that you can only have with a one-way ticket.

In an attempt to satiate my travel lust, I devoured every book I could get my hands on that involved someone going off on a big adventure.

As much as I enjoyed the books, they were no substitute for the real thing. But reading them changed something in me.

The idea of going off and traveling the world for an extended period of time shifted in my mind from “extreme bordering on impossible” to a foregone conclusion (“everybody else did it, soon it will be your turn”). 

Instead of becoming the average of my five closest friends, I was determined to become the average of my five favorite adventurer-authors.

I was just waiting for the right time.

As if one day my parents, the rest of my family, my friends, my business partner, our clients, and the guy who cuts the grass in front of my house were all going to sit around me in a circle, like some kind of intervention, and say, “It’s time for you to f*** off and go travel the world for a few years. Don’t worry about us.”

Obviously, that never happened. Instead, our biggest client went bankrupt.

The Perfect Time

It happened in an instant. This was a company that we had been working with for years. And they had always paid us for our work, until one day, they didn’t.

They owed us over $100,000 at the time. 

They went bankrupt just before they were supposed to make the final payment to us. We had just about covered our costs for the project with the payments they’d made previously, so the final payment that they owed us was nearly all pure profit. 

Fortunately, we had other clients, and other sources of income. So we didn’t need that money just to survive. We could still pay our bills. I was grateful for that, but it was still a huge hit financially and psychologically.

This was more money than I had ever made in a single year. And it was going to be in addition to my regular salary. Like a bonus.

Bonus money is the kind of money that makes dreams come true. The kind of money you use to buy a really fast car. Or in my case, the kind of money that would make it possible to travel the world for a long, long time.

For years I had been telling myself that, one of these days, I’m finally going to do it.

And in my mind, this money was the money that was going to make it possible. So, when I finally accepted that we weren’t going to get paid (we chased them for a while, angry letters, lawyers, court, etc). I wasn’t just angry, I felt as if my dreams had been crushed.

But going through that experience also made me realize something.

I had been lying to myself.

I didn’t need all that money to travel the world. Sure, more money would have given me some additional security, but it wasn’t strictly necessary. “I need more money” was just an excuse (it usually is). A way of rationalizing to myself why I wasn’t pursuing my dreams already.

Losing this money had hurt, but we survived. And for all our fears about wake up calls becoming obsolete and us going out of business, it still hadn’t happened.

Five years after quitting our corporate jobs to work for ourselves, we weren’t billionaires, but we didn’t have to triage the bills every month anymore either. We may not have been a unicorn startup with a hockey-stick-like growth trajectory, but we were doing alright.

“In fact,” I tried to persuade Poya, “we’re only spending about half of our time on billable work. If we just did the projects that came in the door, and stopped doing all the other stuff (like going to dental industry trade shows and cold calling newspapers), then we could spend the other half of our time with our thumbs up our asses and we would have even more money!”

(after all, going to trade shows and hiring sales reps wasn’t free).

But I wasn’t planning to sit around thumb-assing. I wanted to travel!

By that time, I was already working almost entirely from home. We had a few clients whose offices I would go to from time to time, but that was mostly about keeping up appearances. It was rare that I needed to be on-site to do the actual work.

Plus, although we were based near Washington, DC, we also had clients in New York, Chicago, and Miami. Obviously there was no way I could be in all of those places at one time.

If I could do work for a Chicago-based client from my home office in Maryland, then why not from Bangkok, or Barcelona, or anywhere else in the world with WiFi?

I decided to stop taking any new projects that would require me to be on-site. Sure, that might mean turning down some work, but I was okay with that.

For the first time, I put my dreams ahead of other people’s needs and expectations.

Being able to work from anywhere, even while traveling, solved the money issue. The only other thing left holding me back was fear.

Could I really do this? What would other people say? What if clients found out? What about all my stuff? And my house? I’ve got too much going on! I can’t leave now…

But the more I thought about it, the more I realized that if this wasn’t the perfect time, then there would never be a perfect time.

I was able to work remotely. I didn’t have any kids to worry about. I was young and healthy. My parents were both in good health too. I could get rid of my car and probably rent out my house. And I didn’t need most of my stuff anyway.

There was nothing holding me back.

I decided I was finally going to do it!

On October 15, 2012, I moved out of my house and set off on “a six month journey around the world” (at least, that’s what I told people at the time).

8+ years,
50+ countries, and
300+ stops later…

I’m still going.

To Be Continued…