From time to time, as I go through my life as entrepreneur, I’ll reach a crossover moment where I’ll realize that I’m thinking about my life, for challenges, in a particular way. I had an opportunity to talk recently with Allen Gannett, our next guest, who’s founder of TrackMaven.

I’m sure you’ve heard of Allen, his startup’s growing like crazy, but Allen and I have known each other a while. Today, we’re going to have a conversation: do entrepreneurs really deal with crises in our lives and change differently from non-entrepreneurs? Allen, it’s going to be a really interesting conversation. Thanks for taking the time to do it.

GANNETT: Thanks for having me.

ABERMAN: You know, I’ve been through a divorce, I know you’re in the process, right now, dealing with that, and and I’ve had other things happen in my life along the way, and it struck me that when you face personal crisis, and you have a brain that’s wired up to be entrepreneurial and sort of fail into success, at least I find I dealt with crisis differently from other people, and I just wonder, am I the only one, or is this something that you’ve seen in your own life, or you’ve seen in other entrepreneurs?

GANNETT: Yeah, I think you see it over and over again, I mean the big thing that you see is that as entrepreneurs, we try and rationalize and put everything within some sort of system that we can control, and in our work lives, this is very effective. It makes us very good operators, makes us good managers, makes us good salespeople, because we think about everything as a system. The issue is that, when we try to approach our emotional lives, all of a sudden what happens is there’s a sort of weird disconnect, because you can’t fully control your emotions. You can’t fully control other people. You can’t actually do these things. And so I think, for a lot of entrepreneurs, it’s very confusing. It’s very weird. You hear these stories about Elon Musk and his multiple marriages, and how he would deal with his wives and ex-wives, and you could sense that there’s a sense of like, trying to rationalize or systemize something that isn’t necessarily rational, or isn’t necessarily systematic. It’s very human.

ABERMAN: I don’t think I’ve ever met somebody entrepreneurial who doesn’t believe at his or her core that they can manipulate the universe at their bidding.

GANNETT: Yeah.

ABERMAN: But yet, the journey of life is full of random things that just happen, that you have to deal with. So, it seems to me there are two types of entrepreneurs. There’s one that literally is so rigid they deny the possibility of change, and when change occurs, or emotion occurs, they just jam it down and ignore it. And then the other half, that I think sort of, find ways to take these strategies and fail upward.

GANNETT: I definitely have gone through– so, the company is about five and half years old. I definitely look at, early on in my personal life, and also work life, when things are really bad or stressful, I definitely was a compartmentalizer. I definitely push things down, and just not deal with them. I think the issue is, what you learn over time is that that doesn’t go away. It’s still there, it’s still percolating, it’s still, you know, the soda bottle shaking up and getting fizzy. At some point, it’s going to catch up with you. And so, you have the last sort of year and a half, you had a bunch of experiences, whether it’s getting divorced, whether it’s my biggest investor, Harry Weller from NEA, died suddenly, and I’ve been really conscious about trying to just experience it, and trying just to think and feel out loud, both to myself, both with friends. And that’s been an incredibly nerve-wracking experience at times, but also very rewarding, and enriching, because what you find is that, when you sit on these emotions, and you let them ride, you learn a lot about yourself.

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You learn a lot about what you can handle, what you can’t handle, and also it makes it all lot less scary. That doesn’t happen when you push it away, when you push it down, when you don’t think about it. It just sort of sits there, you know, waiting for you to get tripped up, waiting for you to have another stressful moment.

ABERMAN: You know I think is very funny about what you just described, is that I’ve never met an entrepreneur who wasn’t really empathetic when it came to to their own customers, because you have to understand your customers to succeed. But it almost sounds like a lot of entrepreneurs aren’t empathetic about themselves.

GANNETT: One hundred percent. I think as entrepreneurs, we have, I think it was Walter Isaacson wrote about how Steve Jobs had that reality distortion field, the sort of perpetual optimism, sort of, you know, we are destined to figure this out, destined to be successful, and as a result, when you experience failure, or hardship, or any of these things, I think you’re incredibly rough on yourself, because the reason why a lot of entrepreneurs are entrepreneurs, is they feel some desire, oftentimes I think, unhealthy, this sum desire to push themselves to an extreme level of excellence or success, and they are very, very, very on rough themselves when they don’t achieve that. And I think that’s the problem you see a lot of entrepreneurs face as they necessarily become successful, they’re never satisfied. And in our culture, we look up to this in some ways, we say like, wow, that person keeps pushing, and they want to get better and better and better. But there’s also in an inherent sadness in that. They’re never able to just sit still, they’re never able to just say, ‘I’m enough.’

ABERMAN: That’s interesting to me, because when I think about my own journey, it wasn’t until I went through a couple of experiences, death of a parent and divorce, and the aftermath, but I realized that, if you weren’t taking care of your knitting, if you didn’t have strong relationships with people around you, the rest of it was just nonsensical, it didn’t mean anything.

GANNETT: Totally. It was amazing to see, I think, after Harry died, it was amazing to see, at his service, or any of these sort of moments of reflection, how many people he had a positive impact on. And it was a very shocking experience, actually, to see that. I have this sort of visual in my head–it was the memorial services, and there were hundreds of people packed in this gymnasium. And this was a guy who had an immense impact on humanity, right? He supported entrepreneurs, he mentored people, he gave them resources, he was always helping people. And I think, on one level, you can view that all as highly transactional, but what that really reinforced to me, was that this is actually a very human thing, this is actually a very relationship-driven thing, and it made much more appreciative, because it made me realize that this was someone who really cared about me, and I hadn’t done a great job, I think, while he was alive, of appreciating him, and being vocal about that. And so, going through that experience has since made me, I think, a much more appreciative friend, a much more appreciative CEO, a much more appreciative investee, because I understand that people are putting a little bit of themselves into me and my company.

ABERMAN: I think that people don’t spend enough time really focusing on this, and asking themselves the question: why am I getting up every day? Why am I doing this for, or, more to the point, what’s my legacy going to be?

GANNETT: Totally.

ABERMAN: So ultimately, is our lesson for the entrepreneurs and business people listening, what do you think the big life lesson is for them?

GANNETT: I think the big life lesson is to remember your own humanity, and to be gentle to yourself, to realize that you are going to go through hard times, and to experience those. Because I don’t just think that that makes you a better person, a better friend, a better father, any of those things. I think it actually also makes you a better leader, because all the people you work with, they all experience those things too, and I have definitely found, over the last year and a half, my empathy levels have gone way up, and when people go through struggles, I know what those feelings feel like. I know what those emotions feel like. I think experience hardships or failure make you understand what that feels like for that other person. And you can’t just be a fair weather coach, if you’re a leader, right? You have to coach people through the hard times.

ABERMAN: I’m sure that, over the coming months, we’re going to have you back to talk about TrackMaven, it’s a great startup, it’s grown really well. You’ve got a book coming out in the spring as well. But I really think it’s wonderful that you took the time today to share with folks out in the trenches how to be better, and touch themselves, and how to be more successful in a real way, and thanks for doing that.

GANNETT: Thanks, Jonathan.

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