Champion Story 26 | Ben Baldwin
Recorded on January 7, 2019. The story below is transcribed from an audio interview.
Biography: Ben Baldwin is the Founder of Upteaming.com, a coaching platform that gives high-growth companies the peer and team support they need to achieve their big goals, and of The Founder City Project, a peer community of 1,000+ founders and teams.
Ben has been profiled in The Wall Street Journal, Fortune, Inc. Magazine, and in Toronto Life as one of Toronto’s 20 Most Brilliant Tech Innovators.
He holds multiple patents and is a board member of the Drucker Institute and member of the Innovation for Jobs Summit, founded by David Nordfors and Vint Cerf (“father of the Internet”).
Excited to do this interview with you. Love the work you do with founders.
Founder stories have a couple of different layers that are important to note.
I started doing work with employees because they get forgotten and also make gigantic sacrifices. Some employees take big risks and make sacrifices, but the founder gets all the credit. Their mental health isn't necessarily awesome either. They feel this risk of “I don't want to be a founder” or “I can't be a founder,” but they work their asses off.
What I've learned through working with founders is that sometimes the real stories are the sacrifices that employees make. It's really hard to get people to open up because it makes them vulnerable. You find that when people are vulnerable and they're open, people are drawn in and people want to be led by that type of person. If they open up and they lead through being a real person, it changes the dynamics.
Some people need to make that change into being a manager. It's hard because they don't want to admit that they don't know how to do it. You make a ton of mistakes and you always promise the future and it never works out exactly as planned. They don't know how to explain mistakes or talk to people about them.
It’s hard to show weakness to your employees as well. You start to repeat and believe; you become your own mini cult of ‘what happens if I'm wrong?’ If you repeat it enough, you think about it and you overthink it. The more you think about it the less it helps. The more you get confused, the harder you think you need to work which wrecks things instead of taking time off and moving away.
It's hard to get perspective. Your job's changing and you're changing. You start feeling hollow and embarrassed. Then sometimes mental health steps in and I’m like, “What the hell? I live in a constant state of failure.” Nobody is ever satisfied with the growth rate of the company. No matter who you are, no matter how successful you've become. You settle. There’s always something that you could have done better. Then you're sort of disappointed in yourself.
Thank you for sharing that perspective because we don’t talk about it enough.
I come from an entrepreneurial family, generations of entrepreneurs. I thought it was just my family that goes through this stuff and has these doubts. When I started talking to many of the founders in our city, I thought I was going to hear more positive stories or people saying that it was totally worth it. What surprised me was this feeling of unsettledness, this feeling of, “Did I do enough or did I accomplish enough?”
We go a little bit insane too. For instance, a lot of my friends are in more predictable jobs like some are lawyers, doctors or something like that. Your job as a founder in many cases is to be crazy and to think of stupid shit that may not happen.
You have people who are based in reality and people who think you're full of shit. There’s an element where you get some rational understanding of bumps and bruises. People applaud that but it makes you feel pretty alone because there's no other person going through that weirdness and it's all in your head.
There's this weird existential risk that people have because they're making a sacrifice in something that may be completely irrational. You forget what you're all about and what life is meant for. You think about your vision, your idea of being a founder or starting a company and you get lost. That happens a lot. People try to give you advice and you're like, “No, you don't understand.”
Right. When you describe it, I almost think about it as a game. What would be the parameters right? The game that we as founders can choose to play.
It's a form of virtual reality. You're not living in current times. Would you want your child, sister, brother, mom or someone you care about to live your world with this virtual reality visor? You'd be like “Fuck that.” In doing this stuff, you need other people who are wearing a visor to sort of knock on you and say, “Take the visor off.”
This sort of thinking that you have to have, it's really hard to do because living in the future justifies a lot of the sacrifices that you make now. If you think about the example where there's a chasm. Imagine, we're trying to jump over a chasm (because there's a lot you have to leap over). The thing a lot of people do when they jump, is they look down. But even if they were going to make the jump, you can't jump over a chasm when you're looking down.
If you're going to make a leap, you have to depart and focus on where you're going. That's the world that you want to land in. You can't look down while you're making that leap or else you fall into that chasm and go splat. That gets people stuck in this world. They forego a lot of stuff, and they have a lot of regret. A lot of it's related to time and isolation. They don't treat themselves well either.
I feel empathy and this is something that breaks my heart to see. When I talked to many people who work in this industry, a lot of people have sacrificed much to be here. They sacrificed so much to give something a shot because they really believe that they're going to change the world. That they're going to help our community.
The reality is, when you're playing that game, where are the supports? What happens then? I have many friends right now where their lives are destabilized. It's broken families, relationships, or not knowing who they are after they've spent 20 years building a company, because the company has been them all that time.
Yeah. They shut off the other pieces that are important. I'm guilty of that. The problem is it creates habits and then you have to rebuild positive habits. It's really hard to rebuild habits if you're successful. You can imagine how much harder it is if you're just about to make it, you just need to spend a little more time doing something. I see this all the time, including with myself. Just a little more time to fix something. In my case it was to do with my wife and my family.
It all builds up. They remember that hour differently than you. For them, it was that you're an hour late and they never forget that. The math on the time is messed up. If you think about it, it should be obvious that you get rid of that hour because you spent so much time on your business that you should actually have a lot of hours you could probably discard.
It's hard to think that way. One thing someone said to me, “It’s just a job, right?” That's all it is and leave it at that. If I'm fired or whatever, if everything goes to shit, maybe what's reborn is better than what was here. Whatever it may be, putting regret aside, it's hard to have regret in this business. It's just a job, right? If it's not a job, you are insane. Do you know what I mean? Yeah, it's an important job but it's not as important as you. You exist without this. People forget this.
There are three classifications of time. There's the past; there's this thin, ultra-important and bright current time; and the future is forever. The future just goes past death and forever, it's immortal. The past could extend however long you want. The current is the present time and being present is where all the joy comes from. The only thing that makes you happy is this middle zone. But, it's a very difficult place to live if you're in this high pressure job.
You can't get satisfaction for living in the future, you can't get satisfaction for living in the past. You can get it if you are living in the current time. I’m bad at this. But my wife is really good at living in the moment. People can live in the moment.
Looking to the future is tempting too. That's the thing, it looks shiny. Many of the people who fall into this are high performers. They look at the future and think, "Well, I can build this. This can be built five years from now.”
When you were doing the hand gestures, you were describing the present and how small it is. The present reminds me of a thread.
Yeah. It's like a microsecond. It's not even time. Even if you're scared of the future you can get to live in the moment. If you're in the future you're still looking into the future. Everybody's pointing the same way because you're looking progressively toward tomorrow. I see a lot of difficulty with founders or people who have to do that for their jobs because you make a sacrifice.
When I had my first startup, I did a lot of things wrong. I was working 100 hours a week and telling myself, “It's okay. I can do this for the next 10 years and I can enjoy my life later.” When I look back at how I felt even in my body, it's a big difference. I can feel it now because I do a lot of practices to be present and I create a lot of space in my life.
When I look back at those times, I was floating. I was floating around, disconnected and ungrounded from my life, and I didn't even notice it. I remember it ruining my relationships, like, “I can tell that you care for me, you love me, but I don't feel you. I don't feel I've been hanging out with you for three hours. I can't feel your presence here.”
Yeah. If you think about it, your kids know when you're not in the moment. They know if you're living in the past, they know when you're living in the future, and they know when you're thinking about your phone. Even if you don't have your phone, they can tell you're not paying attention.
I have a lot of trouble with being present. I'm always thinking it's difficult for me to enjoy the moment. I love live music. It makes me happy being in the moment. The way I define it is that it doesn't get better when you fast forward. Podcasts as an example, you can fast forward. I can listen to all my podcasts one and a half or two times speed. You can make it faster or you can make it slower. You can stop and restart it again. But if it's something you don't want to change the speed of, like making a live show faster… it would suck.
Right, like a sports game.
Right. You can't fast forward it. With sports, if it happened before and you're watching a rerun, maybe it's okay. But, it’s not the same. It's not the same aura.
If you're at a live show, you don't want to go backward. You're enjoying the crowd and you're hoping for something in the future, but you live in that moment. It's the crowd. It's the band on the stage. You don't want it to go faster, you don't want to go slower. That for me is the clearest example and it's when I'm happy. It’s the razor thin time of the present.
I actually loved that we're going in this direction. I'm in this existential phase right now in my life because I thought that was the solution, building a company. Many things look differently for me now. My family and I just went through the first anniversary for my late brother's death.
One thing that surprised and humbled me was when you talk about being present. I was talking to people who I've known over the years in the tech industry, it looked really different. One thing that I noticed was when I talk to certain people, it was hard to find that spark that they had. The fire that they had is just not there, as if, “I can hear you saying the words to me, but I don't feel it from you.”
I’m like that.
Oh, I didn’t mean you specifically.
That's what my wife says. She's like, “You have said this stuff, but you're robotic.” It sounds like you're saying the right things at the right time when it is not. And, I have no idea that I'm doing that, which is a problem because it's weird. I notice that in other people. You're awkward or not saying this because it's the right thing.
I realize now, a lot of the time I think that it is me and I am trying to be genuine. I think that a lot of the time I don't know whether I'm not being genuine or maybe I tricked myself or maybe it's their fault. That bothers me a lot. I'm not sure where reality is. Do you know what I mean? Does that make any sense?
I say something and sometimes I don't even know if I meant that. I can take the time to handwrite a note, give someone a hug or do something that I really think I mean. Then, every once in a while, it will be an awkward hug and it will make me think. I wonder about that sort of stuff. How much do I actually know about myself? Even when it's those moments where other people are like, “Ben is definitely this…”
I can relate to that. With my first startup, I had a mentor of mine. One day, he pulled me aside and said, “You’re really brilliant operationally. You have a sharp mind. But you can go even much further as a leader if you came from the heart.”
At the time, I was like, “What does that even mean?” I came from a background in neuroscience and I was very logical. He said to me, “When you talk, there's just something missing.”
I didn't get it for five years. After I had my whole experience with burnout where my body broke down, I was willing to work on myself and my leadership. I totally misunderstood something about life. I realized I was in my head a lot and people couldn’t relate to me. Does that happen to you?
Yeah.
I feel we can do better than telling people, “Hey guys, you worked 100 hours a week and look at all these fancy valuations.” Then you don't get to enjoy your personal life. You don't get to feel and you don't get to do this or that. There's so many brilliant people in our industry and we can do better.
It's hard for a founder who's just like a machine and not in any negative way. There was this one person, and I asked, “What would happen to you if you broke both your arms? Could you type? If something happened if you had an accident and you were in bed would you stop working?” They said, “No.” I asked, “Would you find a way?” The guy then said, “Of course.”
It was probably more advice than anything but I don't usually do this. It's like “You know you can probably chill out. You'll be fine.” He is like, “I believe you but it's really hard to change habits.” He always wanted to do more. That's the tragedy.
The story that I always tell, even though it's not mine, because I was actually there for this and it was crazy. Two weeks every summer, I used to volunteer at a camp called Camp Oochigeas, which is for kids who are undergoing treatment for cancer and/or dealing with its aftermath. We spend time with the campers both at the camp and at the hospital. One of my campers was in the hospital for a check up--she was this awesome person, super happy and was in remission. I was around the corner when I walked past the room right after her parents had learned that she was no longer in remission. She had a severe, incurable case of cancer. She was reassuring her parents. She's seven and said, “I got an extra year because my friend from camp died when she was six. My extra year is a gift.” I get more emotional about that story because I have kids. That's a helpful way to think about time.
That is what I think you are hearing a lot from founders stories. Hearing the frameworks that worked for them or “Here's what I did that was successful.” It's a lot of learning and mistakes. Let me say that I learned a lot from that.
Yeah. Thank you for what you shared.