Running a startup requires confidence, but also humility

Dave Balter recently released his book, The Humility Imperative.
Dave Balter recently released his book, The Humility Imperative.Erin Clark/Globe Staff

Founding a startup takes a lot of confidence. Convincing investors to back you, prying talented employees away from other firms, and pushing the button to launch an untried product all require a strong belief in your own capability.

But for some business leaders, that confidence can obscure another key trait: the humility to listen to the people around you, adapt to new and changing circumstances, and admit you don’t have all the answers.

Dave Balter, a serial entrepreneur in the Boston tech scene, believes humility is in much shorter supply than confidence in his industry. This week, he released “The Humility Imperative,” a book of his collected writing that describes how he learned to swallow his pride, what he’s still working to improve, and how he is applying those lessons at his latest company, the blockchain analytics firm Flipside Crypto, where he is chief executive.


Balter sat down (via video conference) with the Globe this week for an interview about leadership, diversity, and workplace culture during the pandemic. His comments have been edited for length and clarity.

On what humility means in business: Balter says he has learned to rely on his employees to level with him and help him make decisions that reflect the depth of expertise that exists on his staff. They’re not working to placate him, but for their own self-satisfaction.

In order to motivate a team to become highly effective and drive outcomes, you have to lead with humility. That means sitting back and being open and failing and doing all of the things that it takes to learn through the process.

You look in the moment, you can see 1,000 points of failure. If I looked at our company today, I look at, “God, that’s not working, and this product is messed up.” What I used to do is go in and attack: “You’re not doing this right. Go do this. Let’s do better. Come on, you guys, let’s perform.” It was more like a demand for outcomes, and people driven out of the fear of not delivering to the CEO’s want.


Instead, what happens now is I look at the failures as mini-achievements, and moments where people can take those items and say, I want to do better personally, not for the CEO, but for me, and this company, and let that flow a little bit more.

On diversity initiatives at his company: Flipside and Balter are facing a problem that is endemic in the overwhelmingly white, male technology industry. He said 6 of his last 10 hires have been women, but people of color remain underrepresented on his staff.

We looked around the room, and we said, we are a very white company, and that feels horrible in this day and age. The first thing we did was communicate as much as possible that we’re going to be authentic with our peers about the truth: Whether it’s subconscious or conscious bias, we have to be open that this is what the company looks like.

We talked about, how do we change our hiring process? How do we change ourselves and educate ourselves in order to transform how we bring other cultures into our business?

I feel horrible about the insularity of tech and the insularity of how a company sometimes subconsciously creates an environment that doesn’t sustain all colors and all kinds. And the first step is to admit where you’re missing, and the second step is to make changes to address it. I think we’re making progress. We’ve got a long way to go.


On running a workplace during a crisis: Balter said he has been trying to adapt his team to remote work during the coronavirus pandemic. Doing so has meant continually reassessing the needs of the people who work at Flipside and finding an effective way to collaborate.

We’ve had to adapt what it means to build a company, and to build interpersonal relationships, to the times we were in. I think great businesses are built when you see challenges and you identify opportunity. I feel like in some ways this situation is going to build a different, kind of enabling, culture than we’ve ever had before.

The first few weeks were — we all went through it. Young kids at home. Some employees have babies. My wife works. I work. I’m trying to balance. Kids are coming in here yelling in the background. Everybody’s freaking out.

One thing we tried to do is let people book the office, alone, for the day. Get some respite from home life. That failed, actually. To a T, nobody wanted to take advantage of it: I really do have to take care of the kids. My spouse will get upset. I’m a little bit afraid of COVID. We felt the tension early, but we did not come up with great solutions. As a team, we had to evolve into new patterns together. That was hard to do. I still don’t think we’ve got it all figured out. There are people who are really challenged, and we just don’t have all the answers to solving them.


“The Humility Imperative” was released on June 30 and is available on Kindle, in paperback, and in hardcover.

Andy Rosen can be reached at andrew.rosen@globe.com. Follow him on Twitter @andyrosen.