Ask Andy: Startup due diligence, and candor with coworkers

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As a software developer who would like to work for a startup, what should I look for in a company so that I know it’s legit? If I am putting a lot of work into a product, I want to know that at minimum it’s for a legitimate company and founder—not just another person with an overdone app idea that knows nothing about the tech world. – Sarah C.

If you’re learning the startup game, the best bet here is to go later-stage. Focus on a pre-IPO company that is growing quickly, has raised money from blue-chip investors, and is getting positive buzz in the market that it will go public within the next two years.

Then, don’t believe any of it. 

Network your way into three of the company’s team members on LinkedIn or through your network. Have three virtual or IRL coffees. Have them tell you about the culture: If they’re learning; if the company’s really growing; and most importantly, whether or not they respect and, ideally, admire the leadership. 

Keep looking until you find this vetted opportunity.

That’s a systematic, rational approach. But that’s not the only way to go. You could throw it all out the window.

Find a company where you believe in the mission. One where you fall in love with the product or service. You might already be a high LTV customer or a power user. Check your credit card statement and your app home screen to source ideas. Your passion for the mission will make it work for you for some time, even if the company doesn’t work in the long run.

However you get there, once you’re inside for a year or two, you’ll be learning. 

You may have to switch horses. That’s okay. 

When you do, you’ll know more people, you’ll have more insight, and the path on what to pick next will be clearer. Heck, you might even notice an inflection point and meet a cofounder that leads to you starting a company yourself. 

It’s like dating. 

You probably won’t marry your first love—but you might. If you don’t, your judgment will iteratively improve. And the good news is unlike a marriage, you can change out your partner every few years. (What I’ve found, though, is that the most successful people professionally, and those who generate the most wealth, have more like 5- to 10-year runs.)

Trust your intuition. Follow your heart on the mission or product. Then, don’t trust yourself.  Study the market. Use the product.  And do at least three off-list references outside of who you interview with. Read every single Glassdoor entry. 

And then jump! 

You’ll be fine.

Do you think you could have shared your mental health conditions publicly BEFORE you were professionally successful, and still have been successful? Or was the fact that you had already achieved professional success what allowed you to be open? – Zack

No, I don’t think I could have shared before we succeeded. I wouldn’t have had the courage to, and I feared it might be career-limiting.

Then again, it was almost seven years ago that I had my I-can’t-deny-this-any-longer moment with my Bonobos colleagues and investors. As of today, I think it’s becoming more possible to be candid about mental health. I hope we can move to a world where I could have been more open, sooner, at least selectively with my leadership team and board.

Some entrepreneurs ask me when to tell their VCs about the mental-health challenge or mental-health diagnosis they wrestle with. I always say the same thing: at a breakfast meeting, four months after you’ve closed the round and hit your numbers. Nobody cares about your neurodivergence if you’re performing—and most VCs actually know enough to know that most founders have more going on than meets the eye.

With your team, I think it’s doable, even now. Perhaps especially now. The truth is, they know. They know you deal with stuff because they’re around you. And the vulnerability you share in disclosing will multiply their respect for you. More importantly, it’ll give those team members the space to reciprocally share their stuff with their colleagues, and potentially you as well, and bring their full selves to work.

Wouldn’t that be cool?

Andy Dunn is the founding CEO of Bonobos and Pie and the author of Burn Rate: Launching a Startup and Losing My Mind.