Lessons From A Third Grade Software Entrepreneur Turned CEO
The best way to fail is to fail fast. By getting this out of the way early in your career, you can learn from your mistakes going forward.
I experienced my first entrepreneurial failure in third grade.
When I discovered the early computer programming tool HyperCard, I was thrilled by the possibilities. HyperCard allowed me to create Choose-Your-Own-Adventure stories in elementary school, and — enlisting a ragtag team of fellow 8-year-olds — we set out to conquer the video game industry.
The ability to make something that other people could enjoy, entirely from my own vision, was a fulfilling experience. The third-grade me loved it.
I saw my dad forging his own path as an entrepreneur and I wanted to do it, too.
Unfortunately, many of my promises to myself fell through — the massive earnings, the company retreat — as you’d expect coming from an eight-year-old.
But my grade school software development days taught me key lessons way before I realized I wanted to be an entrepreneur.
For one thing, be honest.
My mom, if she’s reading this, is probably already laughing. She remembers the day my teacher called home asking why I was talking about starting a company and taking kids on a trip.
I was already telling anyone with ears that we were going to be the best video game company ever, after only a few months of making games. And I had already announced triumphantly that I was going to take my few “employees” on the coolest company retreat imaginable.
The only problem was, we couldn’t do any of those things. Because we were eight.
But of course that didn’t register. What did become clear was that I wasn’t going to be able to deliver on the promises of success and adventure that I’d made to my friends. As I’m sure you can imagine, they were pretty upset when they found out I had overestimated our abilities. They felt like I’d lied to them, I’d let them down.
Honesty is the most important part of any professional relationship.
Much later, when I was running a web design firm (as an adult), I’d internalized this lesson from my previous experience. Whenever I worked with a new client, I made sure I was upfront with them about what they could expect. It was important to me to be as honest as possible about what I was actually capable of delivering, because I never wanted to face a row of disappointed faces again.
My insistence on complete honesty translated into transparency in managing output expectations when I later moved into the blockchain industry.
You really can’t over-promise output in the real world.
Now that I work with ShipChain, we have to be especially careful about the promises we make. We’ve made a huge commitment to our community and the people who have contributed to ShipChain, so we have to be sure we’re fulfilling our side of the deal and delivering.
A recent study of ICOs found that a large percentage of companies don’t manage to make it to market after the offerings. We can’t afford to be anything but perfectly transparent.
We also have to make sure we’re only promising deliverables we have complete control over. I couldn’t control sales numbers or arranging a retreat in the third grade — the resources were simply out of my hands.
Now, as an adult, I won’t repeat that mistake.
For example, when I was working at Direct Outbound, even though we mailed a lot of deliverables, I never promised an exact date a product would arrive to the consumer. I couldn’t guarantee the post office would deliver promptly. It’s a recipe for disaster to tell a customer, “Oh yeah, it’ll 100% be there on Tuesday,” when you actually only have an estimate.
Not over promising was a hard lesson to learn at the tender age of eight, but it’s been a crucial element of building my businesses going forward.
Work with people who know how to do something you don’t.
In third grade, I “hired” a handful of my friends to work with me on games, and we all had our separate, ‘specialized’ roles. I was something like the lead developer — although I couldn’t have told you that back then — just because I was the kid who knew how to work the software. I decided to bring on friends to do artwork and write stories, so I would have help with creative development.
Since then, I’ve always hired people with complementary skill sets. If I don’t know how to do something, I want to find someone who does.
But this has not been without its difficulties. Even though I learned the importance of collaboration early on, I still tend to think I can do everything on my own. But if I stuck to that idea, ShipChain wouldn’t be half the company it is today.
If I believed I could do it entirely alone, I wouldn’t have enlisted the support of the entire team that’s been able to grow at this phase in our development. I would be missing out on their expertise and knowledge — and that’s what makes our product the best possible version of itself.
As silly as it sounds, third-grade me really set up the budding-entrepreneur me. By failing hard back in the day, I learned a lot of lessons that have helped me achieve success, and I’ve improved on those lessons with every business since. But, also very importantly, I’ve never lied about a company retreat.
Even though my mom still laughs at me for it.
