Ask Andy: Can generative AI solve a startup’s problems?

In this biweekly column, Andy Dunn—the founding CEO of Bonobos and Pie—offers advice on leading teams, building things, and surviving the startup life. Got a question for Andy? Ask it here.

What is the biggest challenge founders (new, old, wannabe) are facing today that can’t be solved with or by technology?Sunny

My first gut reaction was to say “fundraising.” The magnetic, mission-driven zeal that is bedrock to raising venture capital seems to be a hard thing to imagine even generative AI (whatever that is) being able to replicate. 

Then I thought about your question some more. 

If you could upload thousands of pitch decks, analyze founder videos, and then look at the evidence of what kinds of companies and founders delivered asymmetric returns, maybe some supernatural intelligence could be developed that hears a pitch, looks at early metrics, digests the pitch deck, analyzes founder video, and becomes a venture fund. And maybe takes off. 

But you know what would be cooler? If helped founders raise money more easily; if the process was more just; and if biases could be removed from the process so female and POC founders could raise the capital they deserve. 

So you’ve made me think deeper—and here’s where I come out: 

The ability to build a great culture, in its best incarnation, comes from a founder’s love for what they are doing—and by extension their love for the team. Individuals come and go, but most great founders I know love the people they work with, and the culture they’re building matters to the outcome. 

The most elegant challenge in business isn’t building a company that delights customers, or one that shareholders profit from. Those are both critical. But the hardest one to get right is a company where the team loves what they do.

Can generative AI love you back? And express it in a human way? Can it host a team dinner, crack jokes, and check in on a teammate whose loved one is sick to see how they’re doing? Can it grow a person?

Methinks maybe not. 

Your memoir Burn Rate came out at a time when I really needed it. I also have bipolar 1 w/ psychosis and work in a high-functioning job in apparel retail. I’d love to know how you know when to push forward, and when to back off as you pursue your life ambitions? And do you feel you have less confidence since your diagnosis? – Preston Zorner

My instinct is always to push forward. Of course, balance is bedrock. Medication, sleep, therapy are all required to be able to push forward. 

But back off? Only when in crisis. 

At that point the focus can turn 100% to managing one’s mental health and getting back on one’s feet. After a manic episode, or in a catatonic depression—yes, that’s time to slow down and get well. 

And the goal then is to get enduringly stable. I think that’s possible. Once in that state of ever-vigilant mood equilibrium, it’s safe to be unapologetically driven and ambitious. 

As for question two, I have so much more confidence. 

I feel embraced, supported, and more fully known. I wish this for everyone. There is an ocean of acceptance on the other side of disclosure, but only if we’re holding ourselves accountable to staying healthy. If we focus relentlessly on getting and staying mentally healthy, we won’t darken the days of others. 

Let’s shine on instead. 

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