Matthew Bellows on Mindfulness & Meditation for Entrepreneurs
Can regular meditation improve your leadership, enhance decision-making, and increase your innovation? In an informal conversation with Shikhar Ghosh, serial entrepreneur Matthew Bellows discusses the benefits that mindfulness can have for entrepreneurs at any stage. Bellows has spent decades building and scaling three startups while cultivating a meditation practice. Before co-founding his third and most recent venture, BodesWell—a financial planning company—Bellows co-founded Yesware. Under his guidance as CEO, it became a leading email productivity platform serving over 60,000 salespeople at companies like Box and Salesforce. He navigated a successful exit for his first startup, WRG (Wireless Gaming Review) Media, Inc., which CNET acquired. Regular meditation has become an integral part of Bellows’s business success. Building and scaling a venture can consume your life, he concedes. “So much about the startup experience is pulling you one way or the other. Your mind is going off here, you’re getting worried about this thing.” Meditation provides a stabilizing foundation. Watch the video or read the transcript to learn more about the benefits meditation offers to entrepreneurs. Bellows also provides tips on how to start applying meditative techniques in your daily life.
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Shikhar Ghosh interviewing Matthew Bellows on the benefits of mindfulness and meditation for entrepreneurs. November 14, 2019, Harvard Business School.
Matthew Bellows on Mindfulness & Meditation for Entrepreneurs
Shikhar Ghosh: Today we’re going to be talking to Matthew Bellows. Matthew’s done—he’s on his third company now. He’s been the founder of three companies and the new company is BodesWell. So BodesWell is a financial planning company that aligns your financial resources with the life you want to live.
Shikhar Ghosh: And so he’s got a set of tools that allow you to think about what you want to do over the rest of your life and manage your finances so that you are actually capable of doing those things. Is that about right?
Matthew Bellows: That’s right. Thank you. That’s great.
Shikhar Ghosh: Yeah, so I’ve known Matthew now for, what’s it? Four or five years, where we’ve done a couple of cases with you. And one of the things that struck me was your unusual background for an entrepreneur, that you went to from Brown, you switched over to Naropa University, where you studied Buddhism and then spent a year or so practicing meditation.
Matthew Bellows: Yeah, Brown wasn’t weird enough for me.
Shikhar Ghosh: But, as you think about mindfulness practices and the teachings that you spent so much time on, how does that relate to setting up a company, to running an entrepreneurial company? What have you seen as sort of the challenges that people have and the tools and techniques that can be used to make this process a little bit simpler?
Matthew Bellows: Yeah. Well, I just was counting, I’ve been meditating now for about 30 years, so more than half of my life, and so it’s a big part of who I’ve become from a mid-twenties kind of college student to a CEO. It’s obviously not required to found a company. Most people who found companies don’t meditate formally. But I think most people who are successful at founding companies have an intuitive sense of what mindfulness is, which is just very simply the ability to hold your mind, your attention, on some particular problem or task or opportunity.
Matthew Bellows: So having that ability, that’s a very simple mechanical level is really helpful when talking to customers, when planning a product, when talking to investors and learning what they need, when hiring employees, when working with managers, etc. Basically everything having to do with the company can be informed or improved by being able to be more mindful about it.
Shikhar Ghosh:
And it’s particularly important, I’d imagine, because there are so many other competing factors for your attention. If you’re a stock analyst, you get time to just spend time looking at it. Here, you’ve got all sorts of demands for attention. There’s emails going off, there’s decisions that have to be made, there’s trash that has to be taken out.
Matthew Bellows:
In an environment of extreme uncertainty and very little resource sort between success and failure.
Shikhar Ghosh:
Yeah. So when you set up Yesware, you actually tried to structure it in a way that was different with different principles right from the beginning in a more employee-centric way. What are some of the things that you would want to do there?
Matthew Bellows:
The basic hypothesis with Yesware in terms of how we’ve worked with employees or team members there was that if they were happy, and they were fulfilled and they felt like they were at the best place they’ve ever worked, then they would be able to contribute more and do a better job at their business. It was the sense of like over-indexing, if you will, on employees as a stakeholder in the overall equation.
Shikhar Ghosh:
And the basic theory was that that was the driver.
Matthew Bellows:
Yep.
Shikhar Ghosh:
That if you had focused, completely committed employees who were developing as human beings in that process, that they would then take care of the customers. They would take care of the financial, they take care of the products. That was a means to an end in that process, even though it was an end in itself as well.
Matthew Bellows:
Yes, that’s right, exactly. Our basic idea was that people who could come to work and not put on a face, but instead be themselves could bring 100% of their strengths to the work and situation.
Shikhar Ghosh:
Right. And you’d worked in other companies where this was not true.
Matthew Bellows:
Yeah, I mean almost every other company I worked at, it was not true. Some much better than others, but some quite bad.
Shikhar Ghosh:
Okay. So if we switch back to being a founder of a company, and a founder goes through ups and downs almost on a daily basis. The highs are really high, the lows can be really low. The challenges, the ambiguity, all of that sort of casts you almost every day. What are the practices or approaches that you’ve seen from all your training and practice that help you thrive in that kind of environment?
Matthew Bellows:
Yeah, the biggest thing is just to build or maintain a foundation of, you could call it presence, you could call it awareness, you could call it mindfulness, a sense of like you have a ground to come back to, because so much about the startup experience is pulling you one way or the other. Your mind is going off here, you’re getting worried about this thing. Your co-founder wants to quit. There are all these challenges.
Matthew Bellows:
And so if one can develop a foundation to come back to, either in the midst of the flurry or before and after, I think it tends to give more of a structure on which to build a business.
Shikhar Ghosh:
And how do you, how do you start to develop that?
Matthew Bellows:
So I think lots of people have different ways of doing it and sitting meditation, which is the practice that I do, is one of the many ways. But there’s a sense of at the beginning stages of curiosity and exploration, what could this be? And then there’s a sense of practice, practice, practice, and slowly, incrementally building the skill. And then there’s a sense of, oh, I can actually do this, and that I think is the point at which you start to feel this foundation to come back to.
Matthew Bellows:
So whether that’s a martial art or running or sitting meditation or yoga or whatever, it’s the sense of developing this thing that is uniquely you, that is about you, because so much of the startup is about everything else, that if you build this foundation then you can say, Oh that, that, that is who I am. And that sense of like home is incredibly valuable when everything else is swirling around.
Shikhar Ghosh:
So if we go through the three stages that you talked about, the trying to decide how to approach this and making it a priority, the second being the practice and so on. And then the third being the using it in your daily environment. If we start with the first one, how do you as a founder or an early stage employee actually do that? And let’s focus on your experience. So just, while there are many techniques, what do you use?
Matthew Bellows:
Yeah, so what I do, I do a basic sitting meditation, usually for about a half an hour a day, either in the morning before work or in the evening before I go to sleep. And that’s-
Shikhar Ghosh:
And that’s once a day typically?
Matthew Bellows:
Once a day, generally once a day. And some days it’s longer if I have more time. Some days it’s shorter, some days I don’t do it at all because things are just too crazy. But the common, five, six days a week, it’s about a half an hour a day, and so from there, then I have a sense of at least today I did one thing to help me ground myself and sort of get my basis, get back in touch with my core as it were.
Matthew Bellows:
I feel like I had an advantage in that I got to do these practices before I started a company. I think it would be challenging to both start sitting meditation or any kind of contemplative practice while you’re starting a company. But I would encourage people out there to do that if you can, because starting a business is very difficult, as you know, as you know, and so the ability to take care of yourself is a big success factor actually in making it for the five or 10 or 20 years sometimes you need to build a big company.
Shikhar Ghosh:
And so, when you do this, let’s say for a week, you don’t do it. Do you find that there’s actually a difference in who you are, how you relate to others, how you relate to the problems?
Matthew Bellows:
So not only do I find it, but the people around me find it, and they tell me now more and more, like they’re getting more comfortable in saying, and actually sometimes they notice it before I do. My wife particularly is like really tuned in now to the fact that, I can miss stuff, I can forget things. I could lose my mind. I’m less mindful in my speech. I’m less aware of what I’m saying. I’m more reactive. Somebody’ll say something and I just lash right back.
Matthew Bellows:
Whereas with sitting meditation, when I’m practicing it, I have a little more space between the action and my reaction. And having that space then gives me the option to say, how do I want to respond to this person?
Shikhar Ghosh:
So, if I’m not someone who’s done a lot of practice, but I’m deeply interested in doing this. How would you tell me I should start?
Matthew Bellows:
Well, we live in a world that’s richer than ever with opportunities to try these kinds of practices. There are some incredible apps. There’s one called 10% Happier right here in Boston. There’s one called Headspace, and there’s many others that basically slowly introduce people to different mindfulness practices five to 10 minutes a day.
Matthew Bellows:
There are some wonderful books and incredible teachers, both Asian teachers from Tibet and India and Japan and Korea, and also American teachers who are really quite amazing at teaching meditation. So luckily, we can search out any of these resources and just see what resonates with you.
Shikhar Ghosh:
But would you suggest, for example, going on a… Something to get me started, like take a weekend, go on a retreat, do something like that, just to get that first inertia out of the way and then move into.
Matthew Bellows:
If you find a weekend retreat that seems good to you, then I would think that would be great. But it’s much like anything else. It’s much like exercise, you wouldn’t want to go and run a marathon and your first day of jogging. So instead, it’s just better to slowly build up piece by piece by piece.
Matthew Bellows:
Sitting meditation’s the same way. So, if a great friend says, “Let’s go on this retreat together.” You don’t have much to lose, it’s not going to be terrible. But on the other hand, it’s probably, it’s not the first thing I would recommend for someone off the street.
Shikhar Ghosh:
So what’s the first thing you’d recommend?
Matthew Bellows:
I think the first thing I would recommend is to your friends who know something about sitting meditation and get a book to read about this. And if that doesn’t work, then look on the internet for YouTube videos about meditation or on your phone for apps.
Shikhar Ghosh:
Okay, and then the second phase you said was just practice, practice, practice, right?
Matthew Bellows:
There’s a kind of familiarizing yourself with the practice in the sense of… I get to running. You get the shoes, you go for a run, you come back, you feel exhausted, you feel great. The next day, you got to do it again. And that’s often, for me anyway, that’s the hardest part. The first day is easy, the second day is harder. Then the third day it gets easier and easier, and then you build that little habit.
Matthew Bellows:
So the familiarization process is a part of the experience, and it’s sort of getting the practice into your body, and that’s, I mean, that’s the path that I think that every meditator’s actually on. I don’t think you ever actually finished that.
Shikhar Ghosh:
So if we move from, you have this practice, do you have other practices where that make you not so reactive? So, you’re constantly facing stressful situations. You’re facing no from investors, difficult board members, customers who won’t say yes, or things you expected that didn’t happen. Or an employee who didn’t quite do what you wanted to do and it was critical. And in those times, because the stakes seem so high, it’s easy to lose perspective, to become reactive, or even the businesses failing and you take that on as your failure. Those kinds of things, are there particular approaches that you would suggest to people whether they’re meditating or not?
Matthew Bellows:
One exercise that my friend Jerry Colonna walked me through any number of times during the Yesware years was he… I would sort of be going off about how this whole thing’s broken and it’s never going to work. And he would say, “Stop for a minute. Just tell me what would be the worst thing that would happen. Describe to me the worst possible results of these things?”
Matthew Bellows:
And in a sense, just talking that out puts it all in perspective, because people complain about being CEO and say starting a company is really hard and it is, but it’s nowhere near the hardest job that people do in this society. So we are in a very privileged position and just somehow realizing that even if the whole thing blows up, we still have an amazing opportunity, and we’ve been given all this great chance to build this thing. So, I think that that has helped me in the past put things in perspective.
Shikhar Ghosh:
When you have to do something really hard, like fire somebody who you’ve known for a long time, how do you mentally prepare for that?
Matthew Bellows:
So, I do a minute or two of sitting meditation in the office before the difficult meeting. So I’ll try to come to the room early, even five minutes early, I’ll try to set up the room and make sure it’s clean and make sure I feel comfortable there.
Matthew Bellows:
Then I’ll sit there for just one or two minutes, and what I’m trying to do is connect to my body to feel my heart, feel my stomach, feel my seat on the chair, and kind of ground my awareness, my mind, my chatter, my worry, my thinking process, dialogue, with my physical body. And what that does for me is basically help me, when the person comes in to see them for who they are, see them where they are, because I’ve sort of grounded myself in a way.
Shikhar Ghosh:
So could you walk us through just the steps of your process there? Because I sort of get to the abstract level what you’re doing. I’m not clear I could do it. So if you were cooking-
Matthew Bellows:
I’m sure you could do it.
Shikhar Ghosh:
But if you would just coaching me, right, and you said, “Okay, you’re going into this really difficult meeting. Why don’t you try this? Step one, do this. Step two, do that.”
Matthew Bellows:
Okay, let’s do it. Let’s do it. Ready? So imagine in five minutes your co-founder is coming into the room and you have to tell them that they’re fired. One of, if not the most difficult conversation you’ll have in this startup. So we’ve gotten in the room early, we’ve set it up in a way that we feel like it’s clean, the whiteboards are clean and sort of settled.
Matthew Bellows:
So then I just want you to sit in your chair and if you’d like, you can sit upright, you could sit, relax. It doesn’t really matter. But the most important thing is just to bring your awareness from your brain, your skull, where most of our… We’re so visual, you could close your eyes if you like, but if it helps you bring your awareness from your head down into your body, into your heart, like literally, it’s very simply operationally, mechanically speaking. What does your chest feel like right now?
Shikhar Ghosh:
Is it tight?
Matthew Bellows:
Is it tight? Is it loose? Is it… What does it feel like? Just whatever that is.
Matthew Bellows:
And then bring your awareness down to your belly. What does that feel like?
Matthew Bellows:
Can you actually feel your body breathing? Can you feel that feeling of your belly and your chest expanding and contracting?
Matthew Bellows:
And then your seat, which is lik, your foundation. Can you feel your seat? Can you feel your hips? Can you feel your buttocks?
Matthew Bellows:
(silence)
Matthew Bellows:
Now when we look up, the perspective has changed. Right? Our mind is no longer the full, 100% of your awareness. Your awareness is your whole body. And now when the person comes in, you know it’s going to be hard. Even just imagining it, I feel my heart tightening up. I feel my stomach tightening up. But at least now you’re ready. You’ve prepared a little bit. So you’re not just like [blahhhrr] all over the person.
Shikhar Ghosh:
But what you’re not doing, which is really interesting to me, is you’re not going through in your head, okay first I’m going to say this and if he or she says that, then I’m going to do that. And you’re not sort of strategizing, you’re not…
Matthew Bellows:
I think at this point, I mean maybe you’ve done that beforehand, coming into the meeting, you’ve certainly prepared for what you can say and what you can’t say. And you’ve done the compensation package discussion and you know what forms they need to sign. And you’ve talked with the board a number of times about, like there’s no surprises. You’ve done all that normal homework.
Matthew Bellows:
And that will get you far. But I think what I’m really going for is like having a genuine human interaction with this person, as much of a sign of respect for them and for our relationship as, I’m just going to try to cross this off my list as fast as possible.
Shikhar Ghosh:
Because otherwise the charge that builds up in your buddy just says, I really want to get this done.
Matthew Bellows:
I just want to get through it, and then that’s a normal thing, but that then cascades. So then suddenly everything is just, I want to get through this. I want to get through this, I want to get through this, I want to get through this, and you’re just crossing things off your list until you realize, oh, I’m going to die. I’ve done all the things, I’ve crossed everything off my list. I’ve been so efficient. I’ve gotten it all done.
Matthew Bellows:
What a sad way to live. You’ve missed your whole life because you’ve been so busy crossing things off your list, but here you are. This person, you’ve built this company, is coming in to have this interaction with you. Unless you could sit up and be there with them and feel what’s going on with you, then I don’t think you really-
Shikhar Ghosh:
Have experienced it.
Matthew Bellows:
I don’t think you’ve experienced it. And I think you’re doing them a disservice, and I think you’re doing yourself a disservice. Life, by the way, as you know, is not about building businesses. It’s really about being alive and experiencing what we do.
Shikhar Ghosh:
The good and the bad.
Matthew Bellows:
How we affect each other, how we hurt each other, how we are hurting ourselves, how we’re strong, how we can heal, all these things. That’s the stuff of life. So, I’m a big fan of being efficient, but I think it’s over played in our society, and I think in at least if we’re being efficient, at least let’s be aware of ourselves doing it. Let’s be mindful of the time.
Shikhar Ghosh:
So, a last sort of area here is some of the being present is learning how to listen to the other person. So it’s not always, you’re thinking about what do you say next and how do you rebut that thing that they’re saying? What in all your practice have you learned about how do you listen to somebody, even when they’re saying things that trigger emotion in you, that trigger resistance in you, that trigger difficulty?
Matthew Bellows:
The first habit that I try to remember to do, although I don’t always remember to do it, is just after the person speaks, give a little moment. So let them finish speaking, and then reply. During the course of someone else speaking, whether it’s on the phone or in person, it helps to look at them and to sort of admire them in a way, in the sense of like, you’re sort of appreciating them.
Matthew Bellows:
I was just doing it to you as you were speaking, just appreciating just who you are, and the fact that we can have this conversation. That helps me get out of my head about my reactions and my responses. I also find that I-
Shikhar Ghosh:
So literally, when you’re-
Matthew Bellows:
Literally.
Shikhar Ghosh:
When you’re, say in this conversation, is it that you’re just looking and feeling or is it that you’re going through and saying, “Oh, I’m looking at his, the way he looks or the way he’s…” When you say appreciate them, I’m just trying to figure out what exactly is happening.
Matthew Bellows:
I just mean in the same way-
Shikhar Ghosh:
It’s an attitude.
Matthew Bellows:
… That you’re watching a movie. You appreciate the film. You see the scene, you see the lighting, you feel the sound, you feel… You’re being there basically. I don’t have a checklist. But I mean, it might not be a bad idea if you say, I’m going to check out their shirt. I’m going to check out their zipper. I’m going to check out their… Do they have a wedding ring or not, things like that.
Matthew Bellows:
But the real, for the literal capitalists in the audience, I have found through experience that I give better answers if I let the person finish speaking than if I try to jump ahead with what I think they’re saying. Because as often or not, my guesses about what you mean are worse than giving you the chance to finish your sentence and for me to pause for a second or two and consider what you actually meant.
Matthew Bellows:
My first reactions out of sort of habitual response are less effective and less accurate and therefore less good than if I just let you finish. And then respond.
Shikhar Ghosh:
Do you often repeat what I’ve said just to make sure you got it or?
Matthew Bellows:
So, I don’t often do that, but sometimes I do that. And I’ll say something like, “Can I just say back what I heard you… Can I mirror back what I heard you say and tell me if I got this right?” And people love that, they love it, because-
Shikhar Ghosh:
But it also creates the break.
Matthew Bellows:
We’re sinking up, and yeah, it creates the gap that we’re… And it’s testing my understanding, especially when I’m talking to engineers because they’re way smarter than I am. Let me just… “Did I really understand that what you meant is that this is going to ship in two weeks and not three? Are you sure?” So, that’s a very easy technique. If you find yourself jumping ahead to answer the question that you think someone’s going to ask, I think that’s a very good signal for you to question that, doubt that, because we don’t know what’s going to happen in the future, and are jumping ahead is sort of like missing the moment when the person is sharing with us.
Matthew Bellows:
And we’re trying to get ahead to it. It’s like we’re trying to skip ahead in the movie to the time when the light camera goes on. And that’s okay, it’s usually inaccurate. It’s usually wrong.
Shikhar Ghosh:
It’s also, the person sees that, right? That you’re not really listening to what they’re saying that, and very often you fill in the blank of the thing that wasn’t said with your own sort of perception of what they should have said or where they’re going or who they are or any of those things.
Matthew Bellows:
If you’re in sales, or any kind of customer facing role from the CEO down to the business development representative, the best thing you can do is listen, because it gives people the chance to share themselves. And that chance is rare in our society, and it’s a differentiator to just listen to what they’re saying. It’s amazing how powerful that is. So it’s a lifelong practice, but I think that’s the essence of it. Just let them finish and don’t preplan anything, because you’ve gotten to this point. You don’t need to presuppose anything. Just be yourself.
Shikhar Ghosh:
Even if you’re trying to get them to a place, you’re selling them, you want them to buy the whatever it is you’re selling. You want to, at the end of the meeting, set up the next meeting. You’ve got a set of things you won’t actually get to
Matthew Bellows:
This is where I’m maybe less conventional than some salespeople out there, or some CEOs, but I actually don’t believe that it’s either… It’s possible, but it’s not very effective to try to convince somebody to do something that they don’t want to do. My approach to sales is to talk with enough people who have the problem that I can solve and build a relationship such that we can collaboratively solve it together.
Matthew Bellows:
So at the end of our meeting, I don’t want to set up the next meeting unless you say, “This is really interesting. Let’s set up another meeting.” I would much rather have that come from you then have that come from me, and if I walk out of the meeting and it doesn’t feel like you want to have another meeting, great.
Shikhar Ghosh:
You’ve just saved yourself some time.
Matthew Bellows:
I just saved myself a ton of time and you a ton of time, and now I can spend that time finding someone who does want to have another meeting with me. So I’m not concerned with convincing other people to do something that’s not in their best interest. I’m much more concerned with finding those people that I can work with.
Shikhar Ghosh:
So, when you go through any of these enterprises, you’ve created something, there are going to be the inevitable disappointments. So you go in, it just, it didn’t work out the way you wanted it to, a particular customer situation, employee situation, the whole company, whatever it is, right? How do you deal with that? So it’s not sort of in the moment, it’s just that this happened and it really sucked.
Matthew Bellows:
Yeah. So I think the most important thing is just to acknowledge that and be honest with yourself that this is disappointing. This didn’t work out or this is not working out or this is really hard. I personally have a hard time doing that. I personally, my default is to sort of keep charging ahead despite the fact that it’s going off the rails. And that’s not that effective actually, but acknowledging the problem exists, and then taking some time.
Matthew Bellows:
I find at least as a CEO, on my own, to think about what are different options here, options for myself, for the team, for the customer, for the person, and then bringing some of those options to a trusted group of people to bounce the ideas around. Here’s the situation that we’re in. Here’s some things I see that we could do, but what am I missing? What do you see? What concerns you? Is this a problem? Maybe you don’t think it’s a problem. So, that’s the basic approach I take. But if you don’t stop and acknowledge that it’s a problem, you can’t actually, you don’t actually address it.
Matthew Bellows:
I just read this amazing research, which is just published by the University of Michigan about the effects of meditation on error detection. And apparently 20 minutes of meditation for non-meditators increases a brain frequency that signals to the body that you’ve made a mistake. So there’s a little, apparently if you look at the EEG is there’s a little spike in electricity after you make a mistake. That’s like the sort of mind saying, I think you made a mistake. And if you can acknowledge that, then you can go back and correct it.
Matthew Bellows:
But if you just blow through it, you just keep going on, you’ve made the mistake, and it’s 10 columns back in your spreadsheet and you’ll never see it. Apparently meditation is very effective for highlighting that and people.
Shikhar Ghosh:
One of the things that causes a lot of pain for entrepreneurs is when they conflate themselves with the company.
Matthew Bellows:
Yes.
Shikhar Ghosh:
So it’s either on the upside or on the downside, but often more on the downside that the company failed, therefore I’m a failure. And then you sort of live with that and it changes your identity, changes your sense of what you can accomplish, who you are, all those questions. How do you avoid that? Because in the one hand, you’re giving everything to this company for many years, and it doesn’t work out. And you think, I actually controlled that, I did this, I caused all this damage to people’s lives, to investor’s money, to whatever.
Matthew Bellows:
Yeah. I definitely know that tendency and I have actively worked to try to untie the knot between myself and my identity and my self worth as a human being and the outcome of my work. Which is not to say that I don’t find myself conflating those two, but I-
Shikhar Ghosh:
Don’t you need to conflate those two in order to get the energy to keep sort of pushing at 110%?
Matthew Bellows:
I think you need to care deeply about your work and care deeply about the people that you’re working with and the customers that you’re serving and the problem that you’re addressing. You need to care. I don’t think you need to bind your self worth to the outcome of this thing that is a big longterm complicated project, and I feel like the tendency to or the desire to do that or the circumstances in which that’s done is a little bit of an ego aggrandizement as well.
Matthew Bellows:
On the upside, you think, I created this thing, the people that say, “I built this,” I have to talk to those people because no one builds anything on their own. The whole reason to have a company is because you bring together a group of people to do something you couldn’t do yourself. On the downside, you can’t take a 100% responsibility for a 10 year project that created all this value and had all these investors and had all these people. You can’t, it’s not… Life is more complicated than that.
Matthew Bellows:
So, I think you could have both those things, care deeply about the project, pour yourself into it, nights and weekends, and just really want it to succeed and will it to succeed at some level without actually associating 100% of your self worth to the outcome of that project. In fact, when an artist does a painting, like a real genuine artist, they’re doing the painting, right? They’re not thinking about how much it’s going to sell at Christie’s for. They’re expressing themselves in this project.
Matthew Bellows:
And if it turns out that he ended the day, they put it up on the wall and they hate it, they’ll tear it down or they’ll paint over it. There’s this sense of continual re-exploration of a creative process. And I actually think companies are a lot like that too. They’re this moving, flowing, dynamic, random, in a sense, project that you really can’t control.
Shikhar Ghosh:
And have you developed any particular approaches to dissociate your self worth from what’s happening in the company?
Matthew Bellows:
Well, we started with one example, which was Jerry Colonna saying, “What’s the worst thing that could happen?” And just sort of sitting back and pondering that. And then the other is the appreciation of other people and how much they’re giving to the project. It’s one thing to start a company. It does feel good to start a company and to feel that other smart people are joining is an incredibly wonderful accomplishment.
Matthew Bellows:
But when you actually look at the effort and the intelligence and the opportunity costs that those other people are contributing to this thing that you started, it very quickly becomes not your thing anymore. Or at least not only your thing. And same with customers. Some customer at a big company is betting their career on your thing actually working in their world. That’s a big risk. So it becomes partly their thing too. Now we’re sharing more people and suddenly my impact is still important, but it’s not 100% of it.
Matthew Bellows:
So appreciating the other things that people are bringing to the project I think really helps expand the view from, “This is only my thing and I must control it or else it will fail,” to, “We have a big group project here and we want to make it bigger.”
Shikhar Ghosh:
So given the ups and downs of entrepreneurship and given the fact that a majority of entrepreneur ventures will not accomplish what they want to do, at least financially, why do you… You’ve basically been doing this now for for awhile and you’ve chosen to continue to do it with your new venture.
Matthew Bellows:
What are you doing?
Shikhar Ghosh:
Yeah. It’s a completely irrational decision. It is totally irrational. So, why are you doing it?
Matthew Bellows:
Well, a lot of the measure of the irrational thing is because people measure average outcomes by income. How much money will you have at the end of your career, this path versus this path versus this path? And I think that’s an incredibly reductive way to think about your life above a certain income level. Some income levels you need to optimize for cash in the door, but above a certain income level, which the studies have shown is around $75,000 a year, the marginal value of a dollar starts to decrease at about $75,000 US there are other factors that you take into consideration when you think about your next choices.
Matthew Bellows:
Largely, what do I want to learn? Where do I want to live? Where do I see this taking me in the future? How does this work with my other life plan? The rest of my family or my spouse or my exercise routine or my whatever, and so I’m doing it again, because I’m not optimizing solely for financial outcome at this point. And because I finally figured out what I’m good at.
Matthew Bellows:
I spent the first 30 years of my life not really knowing what I was good at. And now three companies in, I feel like I’m actually not a bad software CEO, and so I want to do it again as long as I can and get better and better at it until I can’t do it anymore.
Shikhar Ghosh:
Yeah. And it’s every day you come in and you feel like you’ve grown a little bit, you’ve been challenged, you’ve been bushed, as opposed to being a cog in some big machines.
Matthew Bellows:
Yeah. Yeah. It’s a challenge and it’s a learning opportunity, and I feel like I grow every day and people push me to get better. The environment is pushing me to get better.
Shikhar Ghosh:
Yeah. I often tell my students, it’s a lot like mountain climbing. It’s uncomfortable. It’s hard. It’s stresses you out. And then people climb mountains and when they come down, they don’t want to go to the Holiday Inn and sit in the pool. They want to climb another mountain.
Matthew Bellows:
Well, a little Holiday Inn is probably good, but you get the views too, right? The clouds part, and you’re like, wow, I’ve come a long way.
Shikhar Ghosh: But you could do that watching TV and get a better view sometimes. It’s just different. You haven’t created it. You haven’t gone to that place. You don’t fully experience it.
Matthew Bellows: That’s right.
Shikhar Ghosh: Right. Yeah.
Matthew Bellows: TV is a cheap substitute for actually climbing the mountain.
Shikhar Ghosh: Right. Right. Great. Yeah.
