# Brad Feld, Jerry Colonna and Tracy Lawrence on Depression and Mental Health, The Dangers of Tying Happiness To Milestones & Why Fear, Anxiety and Guilt Are Useless Emotions

20VC · Jul 27, 2020 · 47 min · 8,976 words
Speakers: Harry Stebbings, Tracy Lawrence, Jerry Colonna, Brad Feld
Source: https://www.996.fm/episodes/20vc--ep-0de1d224/

## Cold open

**Harry Stebbings** [0:00]:

I'm always very proud of the shows we do here at 20 VC, but I don't think we necessarily always touch on some of the most important and meaningful topics. And I was very pleased to do the episode on alcohol and drinking last month. And today I have an incredible group of people to discuss depression and mental well-being. Such a core part of the founder journey that I don't think maybe gets enough airtime and spotlight. And so I'm thrilled to welcome some incredible people, starting with Brad Feld, co-founder and managing director at Foundry Group, one of the leading venture firms of the last decade with a portfolio including the likes of Zynga, Fitbit, and SendGrid to name a few. Next, we have Tracy Lawrence. Tracy spent the last eight years as founder and CEO at Chewse, the startup that makes it effortless for office managers to order delicious food for their teams. Tracy grew the team to over 300 people across four markets and raised millions of dollars in venture capital before ultimately selling the business to Foodee. And last but by no means least, we have Jerry Colonna, CEO of Reboot.io, where he's now the professional coach to some of the world's leading founders. Before Reboot, Jerry was the co-founder of Flatiron, an early stage venture fund alongside Fred Wilson. But before we move into the show today,

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## Conversation

**Harry Stebbings** [3:16]:

First, I do to thank you all for agreeing to come on the show to discuss mental health and depression. It's obviously something very, very, close to all of our hearts, but I want start say with maybe a bit of context. I think for me and personal story, was it was years of kind of not feeling good enough that manifests itself in a very bad form of bulimia for me. Tracy, if we were to start with you, when did it become front and center for you? And why do you think it was then?

**Tracy Lawrence** [3:39]:

Probably when I was running my second financing and at this point I had a cofounder, but I was single. And this financing took me probably months to do. And it was just one of the most depressing times that I ever went through. And it kind of culminated in me sort of having what I call an emotional spiral in the middle of my apartment and really questioning whether or not I should be in tech, questioning myself and my self worth. And I think that was kind of a light up moment for me of like, if I continue to not address my mental health, I can't continue doing like living out the big vision that I want in the world. That kind of entering, and it wasn't clinical depression, but I mean, was pretty close and I went through many versions of this. I think that was probably my first like wake up call to it.

**Harry Stebbings** [4:27]:

Did you have anyone to talk to in that period? Because it is a very lonely period, especially on that fundraise alone as a solo founder. Did you have anyone to talk to then?

**Tracy Lawrence** [4:34]:

Well, I was single in terms of relationship status, I did have a co founder. So luckily, my co founder, who I kind of call, and and Jerry knows him, he was kind of my spiritual sage. And he as much as we were business partners, we were also good friends. And he was sort of the first person to tell me, oh, you know, it's okay to cry. It's okay to feel sadness. Whereas me growing up with my Chinese Jewish parents, we didn't talk about our feelings. And to be able to express feelings in a healthy way, he completely blew open the doors on that for me. And I was like, oh, you could you could actually talk about these things and they're real. They're not just imagined in my head. They're not just something to kind of suck in and ignore. So he was probably the main and probably only person that I felt I could talk to at that time. I did have some friends that I could speak to, but I sort of felt like I retreated into a shell. and that was a self- created and self declared shell of, oh, other people can't understand me outside of me building a company because this is uniquely difficult or challenging, which also isn't true as I know now. But I think it was just more of a feeling of shame than anything else.

**Harry Stebbings** [5:38]:

Jerry, you're that person that many speak to today in terms of having that extra person outside of their team to speak to When did kind of mental health and wellness become so prominent for you?

**Jerry Colonna** [5:48]:

Well, it's been a challenge for me all of my life. I grew up in a household where my mother was mentally ill and my father was alcoholic. And so it's kind hard to pinpoint a time when it became an important issue of mine. I think it became something that I no longer ran away from. First, after a suicide attempt at I entered therapy and then later again, as I've shared a number of times in my late 30s when the depression came back. And I would argue that it was only at the time when I was in my 30s that I began to get at the roots of what it was that was behind that phenomena for me, behind the depression.

**Harry Stebbings** [6:29]:

Can I ask Jerry? Sorry, this is a little bit off schedule, but in terms of those earlier years, in terms of kind of the psychological challenges and the alcoholism that you mentioned, I think the hardest thing I find for me with my mother's MS is becoming a carer so much earlier than I thought that I would as a child back when I was. How did you deal with adopting that responsibility so much earlier than you thought you would?

**Jerry Colonna** [6:49]:

Well, to answer your question directly, I'll go back to you for a moment and just acknowledge what you just said, because I think that that's incredibly important. At a much earlier age, perhaps than you were prepared for, you were thrust into a position of being a parent, taking care, being a caregiver. And that's an important statement that you just made because while it's not the only root cause of mental illnesses such as depression or anxiety, it can be a contributing factor because you experienced, and Tracy will recognize this because our mutual friend Khalid Halim, my partner likes to call it early promotion. You experience this phenomena being thrust into early onset adulthood when your emotional body may not have been prepared for it. The positive attribute of that is that at a very young age, you experienced grown up success, if you will. For me, the phenomena was very similar in the sense that each of my siblings and I were responsible for each other and for ourselves. The way it expressed itself for me was that I started stepping out of the household at about age 13 and spending a lot more time out in the world at large. And so we each respond to the pressure of growing up early and being responsible for our parents differently. And it can contribute to the loss of a sense of self as a consequence.

**Harry Stebbings** [8:16]:

Brad, I do want touch on your experiences in kind of personal context. How's it become so prominent for you and how did that kind of manifest itself?

**Brad Feld** [8:23]:

I had my first major depressive episode when I was running my first company in my mid- 20s, and it was triggered by three things happening at the same time. The first was I ended up getting divorced from my first wife. Our relationship blew up. The second was I got kicked out of a PhD program. I was good at running my company, but I was a terrible PhD student. And the third was that I was very bored running my company. It was successful, but I was doing the same thing over and over again. I wasn't very stimulated by it. That depressive episode lasted two years. I learned a lot. I had a probably four or five year therapeutic experience that was profound and impactful on how I approach life. And I had several other depressive episodes that were major ones, subsequent, lots of smaller ones on reflection. Things shifted for me when I was 2013. Again, I had a very major depressive episode that lasted six months. and this was triggered by what I would call, among other things, physiological exhaustion that was triggered by a whole year, sort of nine months worth of things that had cumulative effect on how I felt. I started therapy again. Also at this time, several entrepreneurs had relatively recently committed suicide and there was some discussion about it, but not much. I decided to be very open about my struggles as I was depressed and as I was going through this depression, not just the struggles, but also lots of the things I did. I was already blogging about everything that was going on in my world, so why not this? And I came through that also with a lot of help from Jerry in terms of our own conversations and realized that there was an incredible stigma around issues of mental health in our society broadly, but especially in the context of entrepreneurship. And that stigma that existed actually made things much, much, worse for somebody who was depressed. And that one of my goals and desires would be to try to help eliminate the stigma because my view was that mental health and mental wellness is just a part of our character as humans, and not something to be ashamed of, not something to be unduly burdened by in a way where you create this negative reinforcing loop that becomes a personal doom loop when you're in a depressive state and trying to be an entrepreneur or a leader and running a company.

**Harry Stebbings** [10:33]:

I absolutely agree. and I think kind of having these discussions is key to kind of removing that stigma. I do want to start on a statement that we often hear in this ecosystem and industry with regards to kind of company building, and it's that they're crushing it. Jerry, you said before that no one is crushing it. I'd love to start on this crushing it statement. how do you think about this statement, Jerry, and how do you interpret it and advise others to almost ingest it when they hear it?

**Jerry Colonna** [10:56]:

Well, I bring your attention back to something that Tracy was saying when she was sharing her story. Tracy, when you were feeling what you were feeling and before your co-founder said to you it was okay to cry, what was the challenge for you that you felt like it was not okay to cry? And you made reference to growing up with Jewish and Chinese parents, but can you say more? And I'm curious if the impact of the industry that Brad was just noting was having on you.

**Tracy Lawrence** [11:24]:

Yeah. I mean, this was actually the moment that brought me also to meeting you, Jerry. And it was when we were six months away from the end of runway and going out to raise, I think, our series A. And I just I had a complete fear spiral. And I was in the office in San Francisco, and my co founder sort of saw it on my face. We had a team of maybe 12. And he's like, let's go for a walk. And I get up and we go for a walk, and I go two blocks away and I sit on a stoop and I just start sobbing. And I share with him how devastated I would be not to work with this team and just to be a failure, because we had come to this kind of holy land of Silicon Valley to start this company, and we would fail before we even felt like we had a running start. And that's when he gently told me that it was actually a really beautiful sentiment and that I could share it with the team, to which I told him that he was crazy and that the team would leave because they needed strong leadership and you would never want to show that kind of weakness. And I think part of it was certainly there are mental models of leaders out there who they seem literally fearless. They seem literally without fear. And I think what I've learned from you and from other leaders and living it is that the only reason you have courage is actually as a response to fear, because you actually do feel fear, but there's something even more noble in overcoming that and still moving towards a goal, but it is not without fear. And so I think a lot of that contributed to where I was in that moment.

**Jerry Colonna** [12:57]:

Thank you, Tracy. So, Harry, what I note in Tracy's story is a release that comes from her co-founder, allowing her, giving her the space to say, yeah, not only is this normal, but it's actually beautiful and it's connective. and it was a powerful moment. So now if you go back to your question about this notion of everybody's crushing it or the nonsense of that, and what I often say is nobody's crushing it. What's important about that isn't just the sort of deflating of the stultifying and crucifying image that we're all supposed to be crushing it, but it's also the notion that we're not alone. See, Tracy's sitting on that park bench in that moment, terrified that she's to fail and creating a story that goes along with that, which is that she's to somehow fail that team. Well, that fear of failure is almost a universal phenomena. And rather than seeing it as a means of actually empathetically connecting with other people in the industry, we inadvertently, and because of the shame producing phenomena, use it to isolate ourselves even further, making what is the typical normal rollercoaster struggle into a depression.

**Harry Stebbings** [14:08]:

So when we think about kind of the transparency, like Tracy, you said there with the team and being open with them, a lot of what would prevent me talking about depression, bulimia before, honestly, is actually LP reactions, how would LPs feel. And on the founder side, I guess it's how would my VCs feel? How would my board members feel? How do you guys think about that fear of transparency with these stakeholders who fund a lot of what we do in many respects?

**Brad Feld** [14:32]:

Well, let's start from the premise that every single human being on the planet is flawed, and we're all flawed in different ways. We're all imperfect. And this idealized state that our culture has created where you have to carry yourself and present yourself in a certain way is actually a massive inhibitor of people being effective and successful and on top of it. And I think Jerry said it really well. All of those pressures create endless negative feedback loops, which just makes it harder to be successful or effective or whatever adjective you want fill in the blank with as part of it. this notion that you have to present yourself a certain way because everybody else is presenting themselves a certain way, then creates this recurring feedback loop of loneliness, of isolation. It actually goes the other direction where you become more and more disconnected from everybody else because you know your sort of true sense, but you're pretending or you're behaving in a way to try to look like everybody else who are also pretending in a certain way because they're not being their true selves. And on And on it goes. That doesn't mean that there is a way to be. I think that from my frame of reference, everybody should be however they want be. And the challenge is this notion that there is a certain way to be, rather than to allow yourself to blossom and to evolve the way you are. And from my perspective as an investor, I think entrepreneurs who I encounter and work with, who allow that to happen and allow themselves to evolve and grow their own way, regardless of the outcome of the particular business at any point in time, end up being over a long period of time, much more successful at what they do as humans. And for me personally, I sort of reflected back the other direction. I think the ability to process that stuff in a way that is comfortable for me makes me a much more effective investor.

**Harry Stebbings** [16:32]:

I absolutely agree with that. And I guess you said that kind of about the elements of success there and achieving that success. one that I'd love to ask to the group itself is like, I always attribute happiness to milestones. In the past, I have done this. It's led to not being incredibly happy at all, where you say, hey, when I get the funding round, I'll be happy. When I get the fund, I'll be happy. When I get the X, I'll be happy. And I never get to that level of happiness when I reach that milestone. I guess, like, how do you think about the attachment of happiness to milestones? And what would be your advice and perspective given the many different experiences that you've had?

**Brad Feld** [17:05]:

I so want Jerry to answer this because I know his answer and it's awesome.

**Jerry Colonna** [17:10]:

You'll have to repeat the question. I got lost.

**Brad Feld** [17:13]:

He He was taking a nap. I'm happy to answer it too. There is no correlation, zero, between happiness and achieving a milestone. Sometimes you are and sometimes you aren't. And one of the biggest challenges as a human is often after you achieve a milestone, you're exhausted. And as a result, it's not even that you're not happy, it's that you have a massive emotional down cycle because you're exhausted. And in some ways, much of the quote happiness of achieving a milestone is so temporal that you continue to search for more milestones to keep you happy. And at the essence of it, this is why I want Jerry to answer it. It's all Buddhist and it's all about striving, and it's all about meaning. Jerry, that's your setup.

**Jerry Colonna** [18:02]:

Thank you for that. So there's two or three ways to sort of come at this question. So, Harry, you pointed out that the milestone driven phenomena was an important contributor to some of the challenges that you have. I would actually first of all bring your attention to the linkage between outcome, output, milestone driven ways of being and perfectionism. And they're actually kissing cousins. They're very related because we derive our sense of self-worth and self esteem from external forces, from external achievement. And William James, and I'll paraphrase him, William James, the great American psychologist, said that it is not failure that annihilates us, but it's when we attach our sense of self worth and self esteem to accomplishment of a goal and then fail to achieve the goal that we are annihilated. Now, this distinction is really important because we start to see that external sources, getting your company to an IPO status, selling your company, getting funding, raising a new round of investment, we can understand why we believe that that's going to actually make all of our anxiety go away. Because that's the thing that we're worried about. The problem is that we achieve that goal then all of a sudden the anxieties come back larger. There's a phenomena that often occurs in our boot camps where we gather a bunch of entrepreneurs together to mostly to sit around in a circle and cry.

**Tracy Lawrence** [19:30]:

It's the best.

**Jerry Colonna** [19:31]:

It's the best. But one of the phenomena is people will start to explain that they raised $30 million and they feel worse because they don't understand what's going on. It's because what we've done is we've raised the stakes, the emotional stakes. The Buddhist response to this has to do with the notion of attachment. And attachment can be misunderstood. But let's talk about attachment just briefly. When I attach my sense of worthiness to something outside my inherent being, I am subject to the nauseating phenomena of riding an emotional roller coaster of up and down, up and down, up and down. Yay. I achieved accomplishment. I achieved a milestone. Oh, I lost that milestone. Oh, I bought a new car. Oh, it got scratched. Right? Up and down, up and down. And so the Buddhist response is to try to live in this nondual, non-attached state. Now, as soon as I say that, there's at least one person listening to the podcast who says, but I can't live without goals. I can't live without an objective. And let's be clear, we're not saying that you don't live without goals. What we're saying is you want to have those goals because having goals and achieving milestones is a good thing. The problem is not having goals or not having goals. The problem goes back to am I worthy or not? Am I worthy of love? Or as I say in my book, worthy of love, safety and belonging, if I achieve the goals or not? And that's where we start to get into trouble. And to be clear, we are socialized to attach our sense of self worth to external phenomena from our earliest days as children. Because that's one of the ways as a society we make sure that children are compliant. You'll get an A and feel good about yourself as long as you give the correct answer, not the most creative answer.

**Tracy Lawrence** [21:29]:

Can I add to that too? Because when I was building the company, I remember a direct correlation between my happiness and my revenue line. And it was absolutely I mean, and the revenue line of an early stage startup is everywhere. And it would destroy me because my identity was in the revenue line. And to be very real and transparent, I just sold my company earlier this year, and my inner achiever is still searching for the next thing. It's still generating unhappiness and unworthiness. and it's just taken what was the startup and using that as identity and it's moved it to the next thing, which for me, I love surfing and I focused a lot of energy on getting much better and much more athletic. But now if I have a bad day surfing, all of a sudden I am no longer worthy or I'm no longer happy. And if I don't deal with the underlying hyperachiever and the feelings around it, then I'm not actually going to ever solve for this idea of happiness. In fact, I just fuel it when I say, hey, I had a great day surfing, thus I am worthy. And so I actually, I think about this a lot, and I think it's important to recognize it and try to address it while or before you start a company, but probably while you do it. But it's never going be the milestone that solves it. At least I haven't found that in my experience.

**Harry Stebbings** [22:49]:

Tracy, it's so interesting. You said there kind of about your identity being so tied up in the company and the revenue line. And then I'm really interested, know, you mentioned selling the company. And like, I haven't been on holiday for five years because the company is such a part of me. The the idea of going and lying on a beach and not being the company. I don't know who I am without the company, if that makes sense. Like, how do you feel now with the company being sold? And congratulations for that. But with it being such a core part of your identity now no longer part of you.

**Tracy Lawrence** [23:18]:

I mean, I started the company when I was 19 and sold it at So it effectively was my career to date, right? It was my 20s and really even deeper and more insidiously, it was me. So the company was called Chewse and my mom is Chinese and my dad is Jewish, and my friends called me Chewish. And so I called the company Chewse. And it's these like funny little ways of kind of how the company name happened or the mission happened that actually were all part of me. And actually Jerry helped me uncover this at the CEO boot camp where we were talking about being bullied. And I shared my experience when I was young and I had been bullied so badly, I used to eat lunch alone in the bathroom. And he kind of looked at me. And it was that Jerry moment where he looks at me and I was like, what's going to happen? And he says, he's like, what does your company do? And I was like, oh, we make sure that nobody eats alone because my company was dedicated to authentic connection over meals at offices. It was corporate catering. And kind of in that moment, I realized that so much of this company was actually me trying to heal my younger self and anybody that goes through loneliness and bullying. And so the beauty of that and the light of that is that it really fueled sort of a beautiful culture and a beautiful mission. And I think a lot of connection during the time that we served millions of meals. But the other side was that if it failed, then I felt like I had failed. I had failed on the mission in my younger self. And so fast forward to today without the company, I mean, will admit that I was very relieved to sell it, especially as COVID was hitting and nobody wanted anything to do with offices, let alone shared meals. But I am looking for purpose. And I actually am trying to enjoy that feeling of purposelessness right now and try to center in worthiness and center in what does it mean for me to just sit with me and be okay in that state without achieving anything, without externalizing. It's very difficult for me, I'll admit, and I'm in the midst of it right now.

**Brad Feld** [25:26]:

I to add on to this one, Tracy, because I think that's powerful. I'm to link it back, Harry, to your comment about you and your identity and your company and how you can't even imagine taking a week of vacation because the two things are so intertwined. I'll time travel back to when I was your age. I'm to describe you as in your early but moving towards mid-20s. How's that?

**Harry Stebbings** [25:48]:

That's very graceful. Absolutely.

**Brad Feld** [25:52]:

And when I was in my early moving towards my mid-20s, I was running a company, and the words you just said could have come out of my mouth. And back to Tracy's naming, I'll take Tracy one up. My company was named Feld Technologies. How fucked up is that? And I would joke that I named it after my dad, but of course my identity was completely tied up in my company because every single minute of every single day, the name of my company, my name, what I read, what I wrote, and what I overlapped with, and what I thought about was intertangled. When I sold that company when I was 28, it took me a long time to become liberated from that and liberated from my identity being tied up with my company. When I reflect back on it today, I understand the path that I was on, but I also understand how much that inhibited me in that moment from actually really understanding myself because I allowed my entire identity to be linked to my business and to my work. And it wasn't really until my mid mid-30s when I had a moment with my wife, Amy, and it's the moment that I start the book I wrote, Startup Life. Amy and I wrote a book 2014 about surviving and thriving with an entrepreneur. It's, you know, it's memoir ish and a little biographical, autobiographical, but it's a lot of our lessons learned in our stories. And the moment that it came crashing down on me was in the middle of the collapse of the Internet bubble with the person I was put on this planet to be with. She basically asked me for a divorce, and I was stunned. And it wasn't because she didn't love me. It wasn't because she didn't really want to be with me. It was because literally my words, which I would say things like, you're the most important person in the world to me, didn't line up with my actions. Where no matter what I did, no matter what we were doing, no matter where I was, I prioritized the next random phone call or one more email or one more meeting over basically everything we did together. And it was in that moment, the iota of the moment, but that began from that point forward. Now, years later, I think a pretty intense exploration as a couple of what meaning is. And more importantly, when I reflect back on my early 20s, I wish I had not linked my entire identity to my work. Linking some of my identity, my work totally healthy, but my entire identity not healthy for me at all.

**Harry Stebbings** [28:30]:

Can I ask Brad, I'm too interested in terms of kind of linking actions and words there. I find that like my mother had a really bad relapse the other week in terms of her MS and I used her as an excuse to continue working harder, if that makes sense. It's like, I'm doing it for you. I'm doing the work to pay the bills. And it's like, do you know what I mean? You kind of rationale it in your head as a reasonable thing because you're doing it for someone. I love Amy, and so I'm working so hard so we can have this lovely life. Do you know what I mean? How do you escape that kind of excusory framework in your head almost of, oh, I'm doing it for them though?

**Brad Feld** [29:05]:

I'll ask you a couple questions. If you took a day off completely from your work, could you still pay the bills? Yes. If you spent that entire day with your mother doing whatever the two of you love to do together, and you were fully present for her for that day, would that enrich her life more than that extra day's worth of work would have? Yes. At the end of that day, would your life and would you be more enriched than if you had spent the entire day working? I hope so. And so my response is on the third, which is I hope so, try it.

**Jerry Colonna** [29:44]:

Let me jump in here. The challenge with Harry trying it, Brad, is that he would have to go against his programming from childhood. See, Harry gave us the insight earlier with his question about being early promoted into adulthood by being a carer. And so, Harry, your programming says that A, it's your mission to take care of your mother, and B, there's only one way to take care of your mother, and that is to sacrifice yourself.

**Harry Stebbings** [30:12]:

Sure.

**Jerry Colonna** [30:13]:

And the result of that is actually a loss of your center, of you as a person. And so I'm sorry to interrupt like this, Brad, that this is like an inevitable coaching moment for me. So it's like, it's my program.

**Brad Feld** [30:28]:

The best interruptions in the world programming takes over. But I get the last word after your programming takes over.

**Jerry Colonna** [30:36]:

go for it. So Harry, if we look at the programming, the programming, is my job is to take care of mom by any means necessary, including sacrificing. It's been five years since I took a holiday, So I'm going do something really nefarious here. Okay. I want you to step into your mother's body for a moment and look at her son. Are you there?

**Harry Stebbings** [30:57]:

Yeah.

**Jerry Colonna** [30:58]:

Okay. What does mom want her son to do with his life? To what degree does she want her son to live his life solely and only for her care?

**Harry Stebbings** [31:10]:

She would hate that.

**Jerry Colonna** [31:11]:

Right. And so we're to do the reprogramming right now. The more you sacrifice your life, your personal life, and work hard and hard the more you're going against what your mother wants for you. Do you see that?

**Harry Stebbings** [31:26]:

I do. No, I do. totally. And my question to you is like, maybe arrogant and egotistical, but it's like, what if you feel like you know best and that she doesn't and that actually you're doing it for the right reason? Do know what I mean? And that actually you're the one with the full picture. And so that's a fine viewpoint to have, but actually realism has to take place and I actually know what's best.

**Jerry Colonna** [31:47]:

So you've been a parent for a very, very, long time, haven't you?

**Harry Stebbings** [31:51]:

Yeah. 15 years.

**Jerry Colonna** [31:53]:

Yeah. So half your life or more.

**Harry Stebbings** [31:56]:

Yeah. More.

**Jerry Colonna** [31:57]:

And so there's what she knows best and there's what she wants. And one of the things that we want to start doing is to prioritize her happiness and not just her safety. Yeah. Because you were right when you were, call it 10 years old, that you were programmed to keep her safe. But there's more to safety than just physical safety. There's mental well-being. There's happiness.

**Brad Feld** [32:23]:

Yeah. there there is. Last word, Harry. I chose my phrase carefully when I said try it. I didn't say do it. And the reason I said try it was I think, and Jerry, you can tell me if you agree, I think it was reflective of what Jerry just said. One of the things that I've done to break out of my own programming, when I identify that I'm repeating cycles that might or might not be good, they might or might not be, I don't know. And especially in moments where I have historically thought they were good, but they might not be healthy for me. And as I've gotten older, I learn what they trigger or I learn the response from other people. And the response I listen to the most is probably from Amy. but there's a few other people in my life who I listen to their response when I realize I'm playing out patterns that are maybe not good for me is I try different things. and the experiments, many of them fail. I try something, I'm like, nah, I didn't like that. Hey mom, I actually didn't like spending the whole day with you. you. don't have to tell her that. But you can say in your head, you know, don't actually like spending the whole day this way, but I could spend an hour this way. And that hour might really have impact on her happiness, on me, on how I feel. if I was really fully present for an hour and not thinking about, in Jerry's language, taking care of her and, you know, on and on and on right? That try it, that experiment with your own sense of self. I mean, I'll tie it back to what Tracy said, right? The state that you're in now, I have a friend that calls it a liminal state, An in-between state, right? You finished a thing, you haven't started the next thing, you're in between, you're letting yourself sort of exist and explore and try. Jerry and I have a phrase we like to bounce back and forth, is the phrase striving. Stopping striving is pretty enlightening because our programming as people, as entrepreneurs especially, is that you must constantly be striving to achieve the next goal or the next outcome. What a load of bullshit. And the words themselves kind of make me shrivel up like, no, that's not the essence of it. That's the thing we're programmed to do. And if you decide to do that, totally fine. But if you just follow the program, that's what leads to, at least in my case, real, real, struggle.

**Harry Stebbings** [34:32]:

I think one thing that I kind think to immediately there and kind of final thing maybe before the quick fire, it's like I found in the past a really dangerous thing is like forced striving prevention, which is like, how can I completely escape myself from this world, be it the pressures of family, it the pressures of work, whatever that may be. And it's always been like drinking. And I was talking about kind of drinking before, and that escapism from this world to a completely other world where you can kind of be anything and be a normal 23 year old and just act the way you to act and just be very real and new. I guess my thoughts like, how do you think about that forced removal of yourself from striving and maybe the dangers of it and how you think about that?

**Brad Feld** [35:11]:

I'll be super crisp on my last statement. My last statement is not an advocacy to strive or to not strive. It's to disconnect from the programming, to use Jerry's words, and to recognize when you are simply reacting to what other people think you should do or want you to do or what has been sort of ingrained in you and how that's impacting how you feel emotionally at any moment in time. And we have in tech and we've had for a long time in tech, lots of systemic problems and challenges. Some of them in the last four or five years have finally come to the fore around gender equity, racial equity. There has long been a drug and alcohol problem in tech, not just in tech, but in lots of different parts of business and society, acknowledging it and then understanding what's at the root cause of it. And then some set of people deciding to change, change their behavior and change their interaction with it. So it's not that it's good or bad. It's not that there's a specific judgment when you say, you know what, I'm to disconnect from my professional work image now, and I'm to go be a normal 23 year old. I'm not sure what a normal 23 year old means anymore. I'm not sure there's such a thing as a normal 23 year old, but I'm ready to be hairy. Not with my professional armor on and not behaving as a professional. I think that is degrees that if you allow yourself to experiment and explore in those dimensions earlier in your life rather than later in your life or suppress it forever, you'll start to find the configurations of things that bring you fulfillment, joy, happiness, whatever words you want use. And I'll lob it over to Jerry to put a better framing around that last rant, but that's how I to be precise about the last thing I said.

**Jerry Colonna** [36:56]:

Yeah, the only thing I would build upon that is just a quote from Carl Jung that I really adore, which he says, until you make the unconscious conscious, it will direct your life and you will call it fate. The issue behind all of this is, are you conscious of what's actually going on? Are you conscious of the effect of the programming? And once you have consciousness, then you have choice. And if you choose to never take a vacation, Harry, do so consciously. If you choose to derive all of your self worth and meaning from your job, do so consciously and fully conscious of the cost and benefits of doing that for your relationships, for your internal happiness. If you think back to Tracy's journey, so much of what Tracy's been through in the last years has been, this is my projection. Tracy is somewhat your older brother, is just raising your awareness about who you are and what motivates you. And I think that that creates the ability to respond from a mentally healthy place.

**Tracy Lawrence** [38:04]:

And like, this is one of the things that Reboot taught me, which is if there is light and shadow in you, you, have to own the shadow. And I think for me, so much of my shadow has been around guilt. And so, Harry, when I think about if you to take a day, take a week, take a vacation, one thing I found because I I felt guilty when I wanted to take time off because guilt is my operating system. And what I started to do was to, instead of shy away from it and let it fester in a basement, I brought it out to light and I started to tell people and I said, hey, I'm taking a vacation. I just raised a big round. I'm exhausted and I need some rest time. I would even start to own the shadow of the fact that I would go to therapy and coaching. I had a block on my calendar every week. And when people asked, I'd tell them I was going to therapy. And it was something that people actually were very supportive once I owned it. But if I didn't own it, then my mind warped the perception as it was something shameful. So I think owning the shadow, whatever it may be, and talking about it with people, starting at least with the people that we feel the most safe with, and then realizing it's totally okay. In fact, it's wonderful. and it gives other people around you permission to take a vacation or to go to therapy. That was probably one of my biggest lessons.

**Harry Stebbings** [39:23]:

I love that in terms of owning the light and the shadow. And I think I've taken it to a whole new level talking to the people I'm most comfortable with on a live podcast. I think that's going extreme.

**Tracy Lawrence** [39:33]:

Pushing the boundaries, but definitely.

**Harry Stebbings** [39:35]:

absolutely. I I do to move that into a quick quickfire round, is incredibly tough given the topic, but let's go for it anyway. And so I say a short statement and then you give me your immediate thoughts. And so, Brad, if we start with you, contemporary mentors, what does that mean to you?

**Brad Feld** [39:50]:

I have been talking about and advocating and developing and working with mentors for a very long time. And I would say the essence of the foundation of Techstars and how we've evolved it is all around the idea of mentorship. In my experience, the best mentorship relationships are ones that I call peer mentors. So when you have a mentor mentee relationship, but over time you both become mentors to each other. So it's not a mentor mentee, but you're each other's mentors. And in many relationships they evolve that way. And I use Jerry as an example. I think Jerry would say the same. I think we each learn enormous amounts from each other and have over a long period of time now, over 25 years. And so Jerry is a mentor of mine and I'm a mentor of his. And the contemporary mentor relationship is that, especially reinforced when it's of the same generation, although it doesn't have to be. It could be an older person and a younger person, but especially when you have that sort of shared time based experience.

**Harry Stebbings** [40:56]:

Tracy, is hustle really healthy as an approach?

**Tracy Lawrence** [40:59]:

I would say that we should disrupt the hustle. And the way I've been thinking about it now that I'm on contracts and and a little distanced from what I was doing at Chewse is I try to take five minute meditations three times a day and five push ups and five sit ups just to get out of the hustle mode, Work is everything mode. And I almost imagine myself as a barnacle sort of attached to this like rock of work and this whole concept of hustle. So I'd say try to disrupt it, try to create a little bit of space between it throughout the day. I don't think it's healthy on the daily.

**Harry Stebbings** [41:33]:

Jerry, what's the biggest misconception around mental health in tech, do you think?

**Jerry Colonna** [41:37]:

Well, I think it's mental health in general. And I think it's that Brad said it well before. It's that somehow that there's this achievable state where everyone feels great and happy all the time. And that is the biggest myth, and it actually exacerbates our search for mental well-being.

**Harry Stebbings** [41:55]:

Brad, what are you doing to make the second half of 2020 not as bad as the first half of bluntly?

**Brad Feld** [42:01]:

A couple of things. One is I accepted that we're living in the middle of a remarkable moment in time, and rather than try to fight or control things, I'm existing within it. Second, I realized that as much effort as I put into taking care of myself, or think I put into taking care of myself, I wasn't really doing a very good job of taking care of myself the last three months because I felt that there were so many things I had to be involved in to try to help to address various versions of the COVID crisis. And while I'm still engaged in many things, whether it's for portfolio companies or for the state of Colorado or for different groups of people that I'm involved in or different initiatives I'm involved in, I reprioritizing myself in the context of that. And the last is I had a framework that I've been operating under for the last year and a half or so, conceptual framework for how I wanted to organize all the different pieces of my work life. and I realized it was not serving me well. And so I tore it up and threw it away about days ago. and I'm just approaching things differently.

**Harry Stebbings** [43:06]:

Tracy, penultimate one, how could fundraising and VC be made less damaging maybe to mental health founders when raising it?

**Tracy Lawrence** [43:13]:

I think for VCs, they should check on the human behind the pitch and probably start by being very vulnerable. And case in point for me was when I pitched Foundry and we were sitting around a table for lunch in the first fifteen minutes. We talked about a wide range of things, everything from like politics to their relationship as friends to Jason's recent wedding. And I got to see them as friends and as humans. And then when they turned the spotlight to me, I was able to be real. And so I think actually being vulnerable, starting that way and then checking in on the founder on the other side and saying, how are you actually doing? Taking the five to ten minutes to do it means everything.

**Harry Stebbings** [43:57]:

Yeah, I totally agree in terms of showing the human behind the logo, so to speak. Jerry, final one. You helped so many of the world's best founders today. What's the biggest challenge for you in your role coaching these incredible founders?

**Jerry Colonna** [44:08]:

I think the hardest thing for me is staying mindful that I can't fix everything or everyone. That's part of my old programming from childhood, and it's something I work with every day. And so I encounter broken hearts, struggling hearts, especially in these times every day. And I have to remind myself at the end of the day that the most important gift that I can give someone is the full presence of my heart.

**Harry Stebbings** [44:33]:

I absolutely love that. And what a way to finish. I to say again, a huge thank you to everyone because really, this one meant a lot to me. So thank you so much for joining me today. and it's been fantastic to have this conversation.

**Jerry Colonna** [44:43]:

Well, can we say thank you to you Harry, for pulling the three of us together. This was not easy, and these are some of my favorite people in the world. And you're now part of that group.

**Harry Stebbings** [44:52]:

That is very, very, kind. As I said, honored to do it. And so Tracy, Brad, Jerry, like, really means a lot.

**Tracy Lawrence** [44:58]:

Thank you, Harry. Thank you. Thank

**Brad Feld** [45:01]:

you.

**Harry Stebbings** [45:04]:

I have to say I really am thrilled that we got a chance to do that. Such an incredible group of people there and very, very, proud of that episode. If you'd like to see more from us behind the scenes, you can on Instagram at Stebbings @hdebbings1996 with two b's. But before we leave you today,

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