Ask Andy: Startup due diligence, and candor with coworkers


Welcome to the first edition of Ask Andy. In this two-week episode, Andy Dunn – CEO of Bonobos and Pie – offers advice on leading teams, creating content, and surviving startup life.. Have a question for Andy? Ask for this Here.


As a developer who would like to work on a startup, what should I look for in a company to determine if it is legitimate? If I’m doing a lot of commercial work, I want to know that it’s probably a legitimate company and start-up – not some guy with an overblown software idea who doesn’t know anything about technology. Sarah C.

If you are learning the basics of the game, the best bet here is to move on. Look at a pre-IPO company that is growing fast, has received funding from blue-chip investors, and is getting the best of the market that will go public in the next two years.

So, don’t believe any of it.

Connect your channel to three of the company’s team members LinkedIn or through your network. Have three coffees or IRL. Tell them about culture: If they are studying; if the company is really growing; and most importantly, whether or not they respect and, of course, admire leadership.

Keep looking until you find this opportunity.

That is a systematic, well-thought-out approach. But it’s not the only way to go. You can throw it all out the window.

Find a company whose mission you believe in. One of your favorite areas is sales or service. You may already be a high LTV customer or power user. Check your credit card statement and your credit card application for ideas. Your passion for the job will keep you working for a while, even if the company doesn’t work in the long run.

But when you get there, when you’re in for a year or two, you’ll be learning.

You can also change horses. That’s good.

If you do, you’ll know more people, you’ll have more insight, and your options will be clearer. Heck, you might even discover an innovation center and meet a cofounder who makes you want to start a company on your own.

It’s like dating.

You probably won’t marry your first love – but you can. If you don’t, your judgment will increase over and over again. And the good news is that unlike marriage, you can change your partner after a few years. (What I have found, however, is that the most successful people in technology, and the ones who make the most wealth, live 5 to 10 years.)

Believe wisely. Follow your heart for work or medicine. So, don’t rely on yourself. Study the market. Use medicine. And do at least three things you haven’t mentioned other than your social partners. Read all Glassdoor entries.

And then jump!

You will be fine.

Do you think you should have shared about your mental health before you became successful in your career, and became successful? Or was it the fact that you were already successful that made you feel comfortable? Zack

No, I don’t think I would have shared it before we won. I wouldn’t have the courage to do that, and I was afraid it might stop me from working.

Again, it was about seven years ago when I had my I-can’t-deny-this-long time with my fellow Bonobos and investors. As of today, I think it is possible to speak frankly about good health. I hope that we can move to a country where I can be comfortable, soon, with my leadership team and team.

Some entrepreneurs ask me when to tell their VC about a mental illness or mental health issue they’re dealing with. I always say the same thing: in the morning meeting, four months after closing the circle and hitting your numbers. No one cares about your neurodivergence if you do—and most VCs know enough to know that most startups have more going on than meets the eye.

With your group, I think it is possible, even now. Maybe especially now. The truth is that they know. They know that you are going through things because they are close to you. And the risk you share in disclosure will increase their respect for you. Most importantly, it will give the members a chance to share their products with their friends, and maybe you too, and volunteer to work.

Wouldn’t that be great?

Andy Dunn is the founding CEO of Bonobos and Pie and an author The Heat: Getting Started and Losing My Mind.

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