My story of becoming an entrepreneur—and how I nearly lost everything on the very first day.
The vehicle shook, and I startled.
“What the hell was that?,” I thought.
And then, as my little car slowed to a crawl, and then to a stop, my excitement turned to a sigh of irritation as I realized what the sound was.
Just a few minutes before, I had shaken hands with the Moke’s former owner.
I had paid him $300. A lot of money for me.
I was nervous, but I was excited about what I had planned for this old, beat-up machine.
You see, Mokes were popular on the island of Barbados, where I was spending a semester “abroad”; officially studying, but mostly indulging my surfing obsession.
They were popular, but renting them—as most tourists did—was expensive.
Living there for a few months, I got to know quite a few of the locals. And I learned that a used Moke could actually be bought for far, far less than the cost of a single rental.
And so that’s what I set out to do: start my very first business.
I asked around for weeks, finally tracking down a dusty, well-loved Moke that the owner was willing to part with for $300.
I withdrew the cash (a good portion of my savings at the time), and took an island bus to the owner’s shop to make the purchase.
As I drove off the lot, I couldn’t wait to get back to my apartment and clean up my new ride, getting it ready for renting.
I was so excited, apparently, that I completely missed the pothole.
And that’s when the sound came.
Four pops, nearly simultaneously. And with the pops, all four tires—every. single. one.—burst and flattened.
Becoming an entrepreneur: My very first business
My new business wasn’t off to a good start.
Already $300 in the hole, I had to spend an additional $200 for four new tires.
Fortunately, my luck turned after that.
I was able to rent the Moke nearly right away to an incoming student: $3,500 for the semester.
And again, and again; I rented it for the following two terms as well, at $3,000 per term before the Moke finally refused to run any longer.
Why am I telling this story?
I was reminded of this story as I was preparing for my Mixergy interview back in 2017.
Friends coached me to focus on stories rather than facts, and while I didn’t get to tell this particular story, I found myself nostalgic as I recalled it.
Most of us remember these key turning points: first jobs, first loves, the first time we discover a problem or cause that we end up dedicating our lives to.
For me, that experience in Barbados was a pivotal moment. It was when I realized that I could, in fact, become an entrepreneur.
All I had was $500. No experience. No sharpened skills to speak of. Just barely enough money to purchase a crappy Moke, and the drive to turn that product into profit.
It’s a lot of fun for me to think about how far I’ve come, and how much I’ve learned, since then. Despite how little I might feel like I’m accomplishing day-to-day, this historical perspective paints a completely different picture… I feel like a completely different person today.
But it’s also valuable, I hope, to share this story with you—to show you how I started, what it taught me, and how you can apply what I learned to your own life or business.
And I hope, too, that this post inspires you to recall your own turning points, so that you can appreciate just how much you’ve accomplished since then.
What I learned building a Moke rental business in Barbados
I was young and inexperienced, and I didn’t know much of anything about business, so the entire process was a lesson.
But here are the lessons that stick out most:
1) Scratch an itch
It’s amazing to me how many businesses are started to scratch an itch that doesn’t exist.
“[Blank] made easier!,” they proudly proclaim, not realizing that most people don’t actually find [Blank] that hard or important.
My business worked because it was a real problem; an itch that people had. They needed transportation for the entire term, and since the market was built for short rentals, it was hard to find rentals of that length for anything resembling a reasonable price.
My business scratched that itch.
Later, I started Groove to scratch another itch: customer support emails are hard to manage, and most of the software out there is clunky and hard to use.
Again, this is a real problem that many people in the market have.
How can you find itches to scratch?
There are two ways:
Start paying attention very deeply.
I actually made a big mistake in our early customer research at Groove.
I’d go into interactions with assumptions about who the person was, what they wanted, what they didn’t want, and what their challenges and goals were. I’d listen to what they said, but I was only really listening for things that would either prove or disprove my assumptions, rather than listening to everything and trying to understand what was truly important.
For example, I’d assume that the customer wanted a certain feature. After the conversation, I could only tell you whether that assumption was correct or incorrect. What I couldn’t tell you—until I started actively listening better—was that some of the offhand comments that the customer made were very clear indicators that perhaps the new feature I was focused on wasn’t even that important to them.
When you begin to listen more actively, you begin to hear the little things that people complain about, often in the form of comments that seem like throwaways at the time, but actually indicate burning pains that need solving. These conversations, whether with prospects, co‑workers, friends or just about anyone else, can become huge sources of business ideas.
Search proactively for people looking for solutions.
Another thing that I’ve seen work for some—it’s a tactic that we sometimes use to source blog post ideas—is searching online communities for problems that people are facing.
Search, in quotes, for words and phrases that indicate that the poster is frustrated by something or looking to solve a problem:
- “How do I”
- “How do you”
- “Can’t seem to”
Here’s an example:
You can get great ideas by running searches like this on Reddit, Twitter, or just about any community where a target market might congregate online.
2) Ask for what you want
The man I bought the Moke from originally wanted $600 for it.
It was more than I could afford to spend, and I told him that.
To my surprise, when I asked him, “could you do $300?” he said yes.
Not only could I afford the Moke, but I could then (barely) afford the repairs it needed when I blew out the tires.
Now, of course, he could have said no.
And often—most of the time, probably—people tell me no when I ask for things.
But people never say yes to things that I don’t ask for. That is, you only get what you ask for, so if you want something, don’t be afraid to ask for it.
I’ve used this approach for many years, and it’s been especially helpful at Groove. We’ve gotten discounts on software, agency fees, guest posting opportunities and lucrative partnerships, simply by asking.
3) There’s nothing wrong with boring
There’s a difference between sexy ideas and profitable businesses.
The overwhelming majority of profitable businesses are boring, and there’s nothing wrong with that.
Renting a single Moke to students is boring. But it was profitable.
Making software for customer support management is boring. But it’s profitable.
If you want to build a successful business, don’t look for disruptive ideas. Look for profitable ones. Even if they’re boring.
4) Start small
My business had no website.
I had no retail space, no articles of incorporation, no business cards.
I made all three of my sales by asking (see #2 above) as many people as I could if they knew anybody that might want to rent a Moke for a semester.
Many great businesses start as small side projects, an approach which can help you validate your business with zero risk.
It started as just a simple email list in November 2013.
I thought, “how can me and my friends find cool products and share them with each other? Why not have a place for us to do that?”
And so the idea was pretty simple, and the easiest way to build something like that was an email list rather than a site. I wasn’t an engineer, so I wasn’t going to invest the time or money in building an entire site from the start, but I could build an email list really easily.o I started one and invited a few dozen investors, founders, and other friends of mine who I thought might like this, and who had an inside track of what kind of tech products were cool.
The way it worked was they could submit new things they found to this email list, which would then get distributed to anyone that subscribed to the list. It would go out each day automatically using a service called LinkyDink.
Once it was up, I shared it on Twitter and Quibb, which is this network of entrepreneurs and startup people sharing and discussing articles.
From those efforts, I got a few hundred subscribers on the email list pretty quickly, which wasn’t mind-blowing but it was enough to say “ok people are going to read this, that’s cool.”
In the next two weeks or so I just kept working, people kept submitting stuff and it started to get some traction.
More and more people were subscribing, and then a few different people emailed me, or I’d see some people in person and they’d tell me, “hey that product hunt email is cool, I look forward to it every day.”
That’s when the spark hit me.
I thought, “hey, I like this thing too, it’s a lot of fun and useful. Maybe it could turn it into something even more meaningful.”
Since it was just an email list, it lacked a lot of functionality.
I had some time since I was only working part-time while looking for other opportunities, and I reached out to a few people.
One of them was my friend Nathan Bashaw, and I told him that my idea was to take this email list and turn it into a community where people could submit on the website and then comment on it, sort of like reddit or Hacker News.
It wasn’t anything new per se, people understood the model, I just wanted to apply it to this new type of community.
I planned on learning to build it myself, so I asked Nathan how he would recommend I go about doing that. And he offered to help, excited to work on it while visiting his parents over Thanksgiving break.
So over a five day period, he and I collaborated over the phone and online, and when we were done we had this really basic version of Product Hunt.
5) But start!
I thought about starting the Moke rental business for months.
I waffled on it.
I wondered if anybody would want to buy from me. I wondered if I would fail and look stupid.
I did nothing.
But finally, I kicked myself in the ass and I started.
I asked a friend if he knew anybody selling used Mokes. And then I asked another. And another.
And finally, a couple of weeks later, I was in business.
The best day to start whatever you want to start is today.
As cliche as it sounds, the hardest part is taking that first step.
Once you do that, you have momentum, and there’s nothing in business that’s as powerful as momentum.
How to apply this to your business
I hope that these takeaways help you get over the barriers that have been holding you back from starting the project that you’ve always wanted to.
And I hope, too, that the post has gotten you thinking about your own “firsts,” no matter what they are.
It’s so easy to forget those early days as we get lost in the day-to-day hustle. But it’s so, so important to realize that no matter how hard or hopeless today seems, you’ve come a lot farther than you think, and you’ll go a lot farther, too.
Note: This article was originally published in February of 2017. I’ve updated it to included new details and insights I’ve had since it was first written.