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5 Career Lessons From A Startup CTO

Do less research, write to Peter Gabriel, and other unorthodox advice for tech entrepreneurs.

5 Career Lessons From A Startup CTO
[Photo: Flickr user Piano Piano!]

There’s a lot of career advice out there, and a lot of it is good. But over the last 15 years I’ve worked at startups (including my own) and big companies alike, and I’ve found that navigating a technology career takes an approach that doesn’t quite fly in other fields. Here are a few, somewhat counterintuitive ways to go about it.

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1. Don’t Be Too Realistic

“Know thyself,” many people will tell you. But while it’s important to be realistic about your strengths and weaknesses, don’t be too realistic about them. You might wind up talking yourself out of something great.

In high school and college I was really into music, especially where it intersected with technology, and I was obsessed with Peter Gabriel because he stood at the center of it. I was studying multimedia databases, and I knew that what I was working on could solve a problem he had—how to categorize and store sounds in a way that would make them easy to retrieve.

So I wrote him a letter. It sounds crazy—a nerdy kid from Michigan penning a missive to one of the most famous musicians in the world. But as it happens, I heard back! I ended up going to England and collaborating with Peter and his crew to build a multimedia database and front-end tool allowing musicians to retrieve sounds based on things like color, temperature, texture, and so on.

Had I been too “realistic” about what was possible and what wasn’t, I never would’ve taken this shot. In the worst-case scenario, I simply wouldn’t have got a response; instead, the best possible outcome happened. So don’t count yourself out. Write that letter; make that phone call; take that risk.

2. Don’t Worry If You Don’t Know Everything

Career counselors wisely suggest doing plenty of research about the market you’re looking to enter, but sometimes not knowing everything helps you take an opportunity you otherwise wouldn’t. My first startup was an online brokerage called Lombard, which was ultimately sold to Dean Witter and Morgan Stanley. When my team and I conceived of the idea to build it, we had no idea of some of the challenges we’d run into. If we had, I doubt we would’ve dared to tackle it.

I’m not telling you to bury your head in the sand, but just because you can’t see every step on the path from A to B from where you stand now doesn’t mean you can’t get there.

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3. Failing Doesn’t Mean You’re A Failure

Success comes from a confluence of factors, and one of them is timing. You’ve probably heard of Angie’s List, the platform that connects consumers to tradespeople and service providers. They’ve been pretty successful—reached a million members in 2009, went public in 2011, and recently hit 3 million users. You probably haven’t heard of a similar business called myHomeKey. Why? It launched 15 years earlier and was a lot less successful.

I was an original member and the company’s CTO. We thought it was an awesome idea—and it was—but we misjudged the timing. High-speed Internet adoption wasn’t widespread enough to support the idea, and people just weren’t ready to rely on a network of advice and recommendations from people they didn’t know.

So it failed—not because it wasn’t a good idea, or because we didn’t execute it well, but because the timing was off. Being able to distinguish a good idea from a good idea at the right time takes experiences like that. Let yourself miss the mark sometimes. It will help you hit it later.

4. If There’s An Abyss, Jump In Feet First

As a technologist, you can sometimes see things others can’t. This happened soon after I started at Lending Club. I realized there was a critical technology problem that could eventually be pretty detrimental for the company if it weren’t solved. I also realized that without a technologist’s background, many people at the company wouldn’t even know a problem existed, let alone how fundamental it was.

Whatever you call it—a fatal flaw, a liability, a cliff—if you encounter one, face it head-on. I gathered the smartest minds on my tech team together and laid out the situation. We agreed that none of us would work on anything else until we’d solved this issue, using whatever resources it might take. Sometimes necessity compels action, not a directive from the C-suite.

5. Don’t Forget Your Roots

Visa is the biggest company I’ve ever worked for, during a period when it was on its way up, and I was moving up with it. I had the opportunity to build up non-technical skills like strategy, fundraising, and management. That was great, but it took me further away from technology—my roots—and from what I loved doing.

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The thing is, I didn’t even realize how much I missed my main passion until I joined a scrappy startup and got right back down in the weeds of solving complex problems. I’m not telling you not to go after that promotion, but do it with your eyes wide open. Think consciously about the balance between hands-on work and being a strategist, between staying immersed in the technical details while being a leader.

There’s no recipe that works every time for everyone, but it’s important to stay self-aware, otherwise you risk finding yourself at the upper echelons but no longer doing what you love—which got you there in the first place.

But don’t take it from me, take it from Peter Gabriel:

Be brave; don’t be afraid to take risks or make mistakes and stay sensitive to other people. If you can build strength inside you then the outside world will respond.

John MacIlwaine is chief technology officer for the peer-to-peer lending company Lending Club. He has 20 years of experience in executive-level technology roles in the financial services industry.

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