David Willbrand, Smokestacks to Startups

 

102. David Willbrand

SPEAKERS

David Willbrand, Will Bachman

 

Will Bachman  00:02

Hello, and welcome to the 90 T report conversations with members of the Harvard and Radcliffe class of 1992. I’m your host will Bachman. You can find the transcript and show notes for this episode at 92 report.com. That’s nine, two report.com. And you can also sign up for the weekly newsletter for this show. I’m so pleased to welcome today. David Willebrand. David, welcome to the show.

 

David Willbrand  00:29

Thank you. Well, good to be here. Thanks for the invitation.

 

Will Bachman  00:31

David, tell me about your journey since graduating from Harvard.

 

David Willbrand  00:37

Well, appreciate the question. And I think probably is, as most people in our shoes would say, this used to be an easier question to answer than 2025 years ago than it is now. Now the answer just gets longer. The older the older we get, and the more time that amazingly passes. So obviously graduated in 1992. I think probably unique among a lot of people in our class. And even in our generation, I got married right away. So married in September of 1992. And my wife was a couple years older than I was, and she was from my hometown. I’m from Cincinnati, originally. And she was back there working and also had some family reasons to be in Cincinnati. So promptly moved back home, after I graduated quickly got married, and

 

Will Bachman  01:34

dating for a while, or how long have you known each other, it

 

David Willbrand  01:37

was sort of a whirlwind kind of deal. We had been good friends, for several years. And then we started dating my senior year. And then it went very quickly. From there. I would say in retrospect, we ultimately got divorced, which I’ll get to. But you know, we were married 15 years. So it’s, it’s, as I say, people say to people all the time, I mean relationships, and for one of two reasons, you either break up or somebody dies. So, you know, we just, we broke up before one of us died, but you know, 15 year relationship for just a couple kids. You know, we grew up together during a pretty important period of our lives. So, you know, it was it’s been an amicable divorce and, you know, a relationship with with our regret. But I would say that I do think that we rushed into it, for sure. I think it was a sense of, you know, you you find yourself graduating from college, I was not a person that really knew what was going to happen next. I think there was an expectation of I had done everything that the world had told me to do. Right, I had worked hard did my extracurriculars, I was president of Student Council and did all that nonsense, built out my application, got lucky and got accepted, went to Harvard. And then there’s a sense of okay, now I’ve done my part world, you know, now you sort of like, take it from here. And of course, it doesn’t happen. And so I think feeling a little rudderless, and a little bit lacking direction. And, you know, she and I were dating and in love and felt like, well, you know, maybe what I’m supposed to do is get married. And then if I get married, these pieces will fall into fall into place. So of course, you know, that was one piece, it fell into place. But there were lots of other pieces that were still a whole jumble that I had to figure out as we all do over time.

 

Will Bachman  03:24

Okay, so you get married in September, and then what happens next? Yep.

 

David Willbrand  03:27

So then, really was was looking for a job I did have an interest in in politics. I know that shocking. Nobody who goes to Harvard has an interest in politics, but I was in a, I was I was back in Cincinnati, I worked on a campaign for a guy who was was running for city council that Cincinnati one. But you know, that was a short lived sort of experience. It was in that fall. And and then the guy who ran the campaign had a relationship with someone who worked at the Ohio EPA. And so he said, Well, you know, you tried politics, right? Strike government. So I took the job with the Ohio EPA, not because I had a deep passionate interest in governmental regulation, or environmental issues, but I just needed to work. And, and so the job presented itself, and the job will was climbing smokestacks, which was, which was not something that my undergraduate experience or anything in my life had prepared me to do. I mean, I guess I was a modern European history major. So maybe there’s like an industrial revolution thing happened in there. But we, you know, we had we were we had oversight from so called regulated entities, polluters, voters have big smokestacks. The smokestacks have to be tested periodically for particulate emissions. And what they do is they hire a firm to come in and actually do the work, you know, to stick in and basically stick in the magic wand and test what’s being emitted. My job was really just to make sure they put the wind into the smokestack, I mean, because otherwise, you know, who’s there to ensure that this testing will actually take, take place the way that it should. So, you know, the regulated entities hated me, you know, when the government shows up, the guys who actually did the testing hated me. So, you know, I would show up with a hardhat, and steel toed boots, I’d climb the outside of these smokestacks, since then it gets pretty cold in the winter, you’d sit up there all day, because once you climb through your feet, you know, you’re not going down. And so you’d sit and watch and sort of talk to these people who were angry at you. So at best, we give you a cold shoulder at worst, we just kind of review the whole time. And as you might expect, when they found out I went to Harvard, that was, that created a whole new level of conversation and dynamic. And if you’re there for eight hours, I mean, eventually, it’s going to come out. I mean, you know, we’re terrible as, as Harvard grads have, we’re always hesitant to share with anybody. You know, we did that whole, I went to college in Boston thing. But eventually it emerges. And, and so the long story short, was I hated it, it was a terrible job. But it’s one of those I look back on, and I’m really glad that I had it, because it it basically forced my next move. Because I think where I was, will that if I had not, if I’d had like a lukewarm job, like an okay job, I think, given my frame of mind and where I was, and how I was uncertain about where I was supposed to go, or what I should do, or how this should all fit together, I just want to float it right. And then you you wake up, and you’re 50. And you’re like, how did that happen? I was just in this sort of mediocre situation. But the job was so bad. It was so terrible. That, you know, of course, I did. What, again, not terribly original, what a lot of us did, I was thought well, how about law school. So that’s, that’s what I ended up. That’s what I ended up doing. And, and basically talked my way into the University of Cincinnati College of Law. So, you know, we were, as I mentioned, we were in Cincinnati needed to be there for family reasons. And, you know, so at this point, it’s like May, right, maybe early June, I’m working this job that I hate. And the only path forward that I can see is going to law school. But of course, you know, admissions have closed, and I’m sort of doing the math in my head. And I’m realizing if I go through the typical admissions process, it’s like a year and a half right? For me to and I cannot climb smokestacks. And of the year and a half, I just, I cannot do it, you can taste off on your tongue, you’re like, even at 22, you’re like, This is not healthy. This is bad. Like, I’m, this is not the sort of place where I should be. So basically, I walked into the admissions department at you see, and didn’t leave, until they were willing to give me like a provisional spot in the fall class. I hadn’t even taken the LSAT yet. I just I just said, I think it’d be a strong student, I really want to do this, I cannot do this job anymore. You know, please, can you figure out a way? Is there anything that I can do to try to squeeze into the fall class? And of course, they start with no, and then you just keep, you know, there’s something about just being physically in the space and being very earnest. And look, no question. I mean, you see is a different level of law school. You can’t do that at Chicago, or Stanford, or Harvard at Yale. But, but, uh, you see, I did, and they basically gave me a provisional acceptance when they got my transcript. And which, you know, I was able to probably get because highly motivated. And I took the LSAT, and they said, look, so long as you kind of keep your head above water with your scores are fine. And, and I did. So I, I started in the fall of 1993. Like, I’m

 

Will Bachman  08:44

not leaving your office, I’m admitted. I don’t think that would work at Yale or Harvard. No,

 

David Willbrand  08:49

it would not. It would not, but it totally worked there. And in fact, it became like, that became one of my safe places. At last, it was great, cuz I became really good friends with them. And like, the dean of admissions, you know, like, because he, I mean, he liked my energy. I was very, like, just, and that’s not I can be enthusiastic and like, committed. But what that was a unique expression were like enthusiasm, and need meet desperation. And like, this is it and it was sort of this unique cocktail moment. And it worked. But they became, you know, I would hang out in that office. And I would study in that office over the next three years. They, they were my crew that the people in the admissions department. So it was it turned out to be kind of a fun, personal experience. But yeah, it’s kind of a wild anecdote. Okay.

 

Will Bachman  09:40

So so no more smokestack climbing. It does occur to me. I just, I mean, would they EPA send an inspector like you every time that is inspected? Yeah. Okay. So we have the contractor who is doing the work, and we have you climbing up watching the person who is doing work? That’s right. Did it ever occur to them to like, cut out the middleman and just have you stick the wand in the smokestack, and then you could get rid of the contractor since you’re there already?

 

David Willbrand  10:10

It’s a very good question. I don’t know how it emerged and the way that it emerged and why it was why it was structured that way. Maybe there was a sense that this was more cost effective. But yes, it does feel like there’s some level of redundancy there. I’m also going to tell you well, now maybe the the art has advanced in the last 30 years. But it wasn’t like a highly precise sort of testing this taking place. I mean, like, you know, the aperture of these ones is pretty small. The smokestacks are massive. And so Oh, they’re huge. I mean, some are small, like, not all regulated. Energy is massive, but we are regulated entities, but we would like go to a utility, you know, Cincinnati, gas and electric. They were 300 feet in the air and extremely broad that the circle, you know, was massive. And you’re sticking this one little instrument. Oh, I mean, 20 feet across.

 

Will Bachman  11:05

20 feet across. Yeah. Did you guys have like breathing apparatus up? There does not sound good to be right at the exit of a

 

David Willbrand  11:16

stack? Yeah. And that’s exactly you know, why I why I was even at 22 was like this. This does not seem like the place where I should be. No, it was smoking

 

Will Bachman  11:30

a cigarette with a 20 foot diameter. So it’s 100% 100%

 

David Willbrand  11:34

I’d had a smoking habit in college. I kicked it promptly after graduation, because my fiance was like, I don’t want to live with a smoker. I said, Okay, I love you. I’ll quit smoking. And then I guess apparently, I picked it up in a different sort of way. But I was able to extract myself from that unhealthy situation.

 

Will Bachman  11:52

Okay, so moving on to the law school. Alright, so

 

David Willbrand  11:58

yeah, so I actually, I love going to law school, there was a small law school, like 100 students per class. And, you know, very direct interaction with the, with the faculty, and they were great. They were very student oriented. And to kind of flash ahead, because I know you sort of refer back to our experience at Harvard, I mean, I’ll be honest with you will, like my, my reflections on Harvard, are very much focused around like my social experiences, they’re the friends I made, the organizations that I participated in. But from an academic and a coursework perspective, my memories aren’t terribly fine. I was a person just sort of fell through the cracks. And in the machine of Harvard, and some of that taught me, you know, not really sort of putting myself out there and getting myself to office hours, getting myself in front of faculty really engaging. But I would also say, I tried a little bit, and I really wasn’t, it didn’t feel like a warm, inviting situation, you know, it was very much faculty who was about themselves. And they didn’t really have time for this random kid coming in with a baseball cap on, you know, who was a sophomore, elaborate. And so it was very different. To be in a situation at UC where I really did feel like the faculty cared, like, knew who I was, knew my name, they were invested in me and where I was heading. So I had a great law school experience, I loved it, which is not what a lot of people say about law school, and really enjoyed it. And then And then basically, to make a long story short, you know, I went into law school, not really knowing what it meant to be a lawyer, it was really just like any port in a storm. Originally kind of thought, well, I did this environmental thing, maybe I’ll do environmental law promptly found out no, because they like to have law firms like to have engineers, you know, people who have an engineering background, I did not have an engineering background. So that was sort of out. dabbled around with some litigation pieces. But that wasn’t really my jam. And then kind of stumbled into the corporate law department. And primarily, because there were a couple of attorneys there that I liked. And we just hit it off. And then I started to get a couple projects from them, and found that I really liked it, and really liked the deal work, the transactional work. And so I got an offer from a law firm in Cincinnati. And took it. And this was, you know, graduated in 96. Took the bar over the summer, and then was admitted and started practicing September of 1996. Doing transactional work. And the reason why the date is somewhat relevant, is that, you know, 1996 is typically noted as the beginning of the.com era. So, you know, I started this law firm, even in Cincinnati, and by the way, I thought that was like, I was going to be at this law firm for the rest of my life, right. I had gone to the local law school, I was at the big downtown law firm, was a Cincinnati guy. My wife was a Cincinnati person like this was just going to be the groove. But of course, best laid plans. The bottom line was that this.com Bubble starts and everybody else inside the loft just kind of got their thing, like, some of they’re doing real estate or banking or mergers and acquisitions or public securities. And then these like startup company, things start coming in. And then venture capital firms are starting to organize even in Cincinnati, which was one of the interesting things about the.com bubble is it really kind of democratized the startup world, which up to that point had basically been Boston, and Northern California. Now it started to percolate. Because, you know, that’s what the internet does, right? It democratizes access to information and opportunities. So nobody else was interested in this work, because they had their thing. And I was sort of like, I just want to keep working, because I don’t want to be climbing smokestacks again. So you know, if it’s billable time, I’ll do it, you know, and I found that I really liked it. And, and so that’s really when I sort of found my thing well, so it was that I’m just kind of stumbling along, up until this point, just sort of bouncing into corners, you know. And then when I would hit a wall, kind of roll down another alley, hit another wall, roll down another alley. But now this is for the first time I add, this is what I think I should be doing. This is what I liked. And this really sort of resonates with my interests and my skills and where I see the world going. And so started doing that work. Now, what ended up happening is, a year later, I ended up moving to Boulder. So I got an offer from a law firm in Boulder that was like a mini Silicon Valley, I always tell people that boulder is not a suburb of Denver, it’s a suburb of San Francisco. And, and so went to move to Boulder. And we were there for three years. And that was you know, the.com Bubble really inflated. And I was really able to sort of advance my career and my skill set there, there was a lot of work a lot of activity. And I continue to love it older was a great place to live, you know, we really enjoyed living there, our family started there. So you know, have a daughter and a son. And, you know, so they emerged when we were doing the boulder thing. But then, you know, as often happens, you know, life sort of interferes or throws you a curveball in the family stuff kind of popped up again. And so it was like, well, we probably ought to get back to Cincinnati. And so did and came back to Cincinnati in 2000. And moved back. And then I took a job with one of my clients and actually believe it or not worked remotely in the year 2000, which was very different than working from home. Now. We didn’t have the technology, we didn’t have the tools. But this was a.com company. It was based in Ottawa in New York City. And I was in Cincinnati, and would travel periodically. But for the most part, I was doing it all from home, I did that for a year. And the reason I only did it for a year is because there’s a reason things are called bubbles. In retrospect, it’s a pop. And that’s what happened with this company is it sort of Now eventually, kind of limped along and sold itself to the Steve Case, family of businesses and assets. But I had to leave because, you know, we’d reached the point where we couldn’t pay people anymore. And you know, I was 32 with two kids and a wife and I needed to make some money. So I joined another startup in Cincinnati, which now we would call a b2b SaaS company, you know, business to business, SAS cloud software company, but that language was not in use 2000 123. That was a struggle bus experience, because that was a very, very hard time. In business in general, and startup world, in particular. We, you know, I had to lay a lot of people off. And as often happens in those situations, my duties increased, you know, as the size of the company decreased. And so I went just from being like the lawyer who was brought on to help take the company public, which did not happen. But then I became responsible for finances, payroll, I took a, I took like a class at the local, like Cincinnati technical school, just to learn how to do debits and credits, which is probably pretty unique. There probably aren’t a lot of people who have like, went to Cincinnati Technical College and Harvard College, you know, that’s sort of an interesting meeting there. But it was great. I did night school, and so that I could learn how to do this, and, you know, build financial statements, and which was just way outside of my comfort zone. But again, when you don’t want to climb smokestacks, well, there are a lot of things that you’ll do instead, and did HR and, you know, in this capacity had to, like, you know, be involved with all of our reductions in force, which was a lot of responsibility and a painful experience for someone at that age and stage, learned a lot about what it meant to manage people. And then how to end in the complexity that everybody has because that’s the problem when you live People go is you suddenly then find out about what’s happening in their lives, you know, because they’re there, they’re afraid of losing health insurance because they’ve got a sick kid, or there’s this other issue that’s chronic in their life, or they’re at risk of losing housing. And it’s terrifying. You know, and it’s a, it’s a hard way to learn some really deep lessons. But I did. And then to sort of speed things along. Eventually, I reached the point where this, this company was not really growing, and I needed to make a change. And so it’s 2004. And I really felt like, I wanted to get back into a law firm environment. So I joined a law firm called Thompson Hine, kind of an East Coast based firm. And they were interested in me because they wanted to create a startup and venture capital practice in the Midwest, they didn’t have that. And it was a growing tier, and segment of that particular market. And I was very interested in doing that. And being on the kind of front end, front edge of that pioneering activity, and that’s what I did. So I joined that firm in 2004. And was there all the way until 2021. So kind of went sociate, Senior Associate, junior partner, mid level partner, you know, old grumpy guy in the corner office, so I had the whole kind of, you know, law firm experience. And again, you know, just like I loved law school, you know, unlike a lot of lawyers in private practice, I actually really loved it. I mean, there are, there were bad days, of course, and, you know, I did not like billing my time, and tracking my time and sending invoices to clients and fighting over invoices, it’s not fun. But I really loved the sort of the disparate work that I did, and the different personalities and people that I interacted with. So when you’re when you’re working with startup companies, in general, and founders, in particular, you’re dealing with people who are, who have given up everything, to pursue this vision and this dream that they have, and you have, you know, really the privilege of joining them on this journey. And they look to you, you know, as a key advisor, and, and it was fun, to be able to play that role and to be, you know, sort of a member of their kitchen cabinet. I mean, of course, I had a professional job to do in connection with providing them with legal services, but it went beyond that. And in many cases, you know, really deep friendships have emerged as well, which is really rewarding and interesting, but they’re also just fascinating people, and you get you get exposed to b2b SaaS, but then you get exposed to people that are, you know, in biotech, people that are working in hardware and devices, and people that are engaged in building apps and doing different sorts of social media is emerging this, this during this period of time, and you get to see what that looks like and where it’s going directionally, and how people are getting on that train in different ways. They’re thinking about it. So you really feel like, not only are you sort of, at the frothy front edge of innovation, but you’re also working with with people that are really enriching your life, you know, as you’re interacting with them. And then I had the additional layer of doing it in the Midwest, which felt like it was a little bit of a calling for me, because, you know, there were 1000 people that looked like me in Palo Alto. But in the Midwest, there were very, very few people that looked like me, because they’re, you know, there wasn’t the same activity, there wasn’t the same volume. But there were some, and in these regions, you know, really kind of developing, cultivating, facilitating and holding on to the creative class. And, you know, having a piece of the stake in the innovation of economy, innovation economy is really important. And, you know, for the future of these regions, so that they get to participate, and they’re not left behind, as the world advances forward and sort of feel like I had a stake in that game. And a role to play was incredibly just, you know, emotionally rewarding for me. And, and so I really look back fondly on that period of my life, you know, call it roughly 30 to 50 where I was in that zone, in participating in that way.

 

Will Bachman  24:18

What happened after 2021?

 

David Willbrand  24:20

Well, so along the way, I mentioned earlier, I got divorced, so it was divorce 2008 ish, and then remarried, a year or so later, to a woman that I actually practiced with we weren’t in the same office, but we knew each other through the law firm and she was in the Cleveland office at the time. We started dating and then got married. So I mentioned earlier I had two kids. She had two kids. So together we have four if we’re being like super dorky corporate lawyers, we talked about a merger and there’s a merger of equals. So we but we lived up Are which was sort of an interesting dynamic. So I was in Cincinnati, with an ex wife and two kids, and, you know, good chemistry with the way everything was sort of working and unfolding. And she was in Cleveland, that’s husband, two kids, same thing, chemistry is working. And the idea was, or as we discussed it, you know, if one of us changes, it really disrupts the chemistry, and you feel like you kind of have like, all the cups and saucers spinning in the right way, you don’t want to do that. You don’t want to mess that up. So we sort of thought, well, you know, we’re the ones that would be introducing that it might be, I don’t know, even selfish, perhaps, for us to disrupt that for the other people that are in our little universe. So, you know, we dated remotely, let’s just get married and live remotely and just, you know, come together when we can, it’s about a four hour drive. And, you know, I think if you had told me, when we got married in 2009, that, it would, we would actually not be like living at the same address for 11 or 12 years, I would have said, no way. Like, I think we both I was probably about a year, and then it would kind of like work itself out. But it didn’t, and we just ended up in this configuration. And it just worked for our families and work for us. And we just, you know, kind of built our marriage around that. And then, you know, she left the firm not too long after that, and started down the in house route. So you know, she had an in house job in Cleveland for a while. And then in Charlotte, for a while, and then in Denton been in Detroit for a while, and then back in Cleveland. And then now in Palo Alto. And, you know, I was sort of more placed in Cincinnati, and then Chicago, I sort of moved my practice and the and the focus of my work there over time. And then we just sort of, I would do most of the traveling, and we just meet her where she was. And so we were, you know, probably during that stretch of life, we’re probably together 30% of the time. And, you know, a part of the rest and it works. That works. And, but ultimately, what happened was coming out of the pandemic, I was, I was feeling a little restless. You know, I mentioned, I really liked what I did, but I sort of felt like I had learned and experience what I was going to learn and experience from this particular line of work and the way that I was practicing it. So, you know, I needed to do one of two things either needed to go do a different job someplace else, or I was going to just need to change the configuration of my practice. Because you don’t want to get stale. You know, I mean, your your mind needs to be fed. You want to keep growing and learning and staying curious, and innovating and remaking yourself. And so I was either gonna have to do it in place or someplace else. So I wasn’t. I had, I had learned over time, there’s a difference between being restless and being reckless. And I knew enough to say, hey, I don’t want to be reckless. But let me just keep my eyes open for opportunities. And I had a client that I had worked with for some time. I’ve represented him when he had started another company and sold that company to Zillow. He was starting another company called Picasso, which is in the second home business. He was starting out with the former co founder and CEO of Zillow, a guy named Spencer Rascoff that I’ve gotten to meet over time, too. And so often is the CEO of Picasso. And he was a friend, as I mentioned, you know, someone who I’d worked with professionally, but also become, I’ve become friends with. And Picasso was growing very rapidly. I was representing them as outside counsel. And he had expressed that they really felt like it was time for them to have a chief legal officer because of the way they were growing, and the complexity of the business and sort of the legal demands and intensity of it. And I said, Well, what about me? And he said, Well, I thought you seem pretty, you know, wired into your practice, I wouldn’t have thought that that would have been something of interest to you. And I said, Well, you know, it might be let’s talk about it. And it happened very quickly. You know, within a week, I had a, you know, practice that I built very lovingly and with a lot of energy and effort over 1718 years, and promptly walked away from it. So enjoy Picasa when April 2021. So I’ve been there since. Wow.

 

Will Bachman  29:21

I have several follow ups questions. What are your tips for making a long distance marriage work? That’s extraordinary. You know, four hours apart. It could be you know, 14 hours apart. It hardly matters if you’re flying or driving or something. What what are some of your tips reflecting on the 11 years that you live separately?

 

David Willbrand  29:45

Yeah, I so I do think I think it would be challenging to do with a first marriage. I think it’s more workable with a second marriage because the expectations in duties are different, like, the expectation was not that she’d be a mother to my children, you know, her expectations for me were not that I’d be a father to her children, there’s a role an important role. But you know, her kids had a dad, and my kids had a mom. And so there’s not the sense of like being absent from that, right or, or not being a part of it, the bulk of the time. So I think not having that level of pressure around it is, is an important nuance to this. And so, you know, if you, if you take that for what it is, then I would, I would actually offer that I would strongly endorse it as a, during that stage of life, as a as a configuration, because basically, what it allows you to do well is that like, when you’re when you’re in that place, and when you’re not with your spouse, you can be all about work, which in your 30s, and 40s is a big, you know, generally there’s work pressures are intense. So you can be very focused on your work without apology, or without the need to try to figure out like, you know, what’s happening with this other person, and am I going to be going home for dinner, and no, you just, you’re doing your thing, and you’d be very focused on your kids. So, you know, when I was in Cincinnati, I was all about my job and all about my kids. And then and she and I would touch base every night, we would talk for five minutes, or an hour and a half, you know, just we would talk every day, just to connect, and she was doing the same thing in Cleveland, or wherever she was, you know, her job, and her kids. But then when you’re together, you’re really together. And, and you really value that time, you don’t take it for granted. So and it’s not a bad thing to miss your spouse. Right. So in in, it really worked for us in that respect. So when we were together, we actually more often than not, we’re together without our kids, because our kids were with their other parents. So you know, if you’re the parent of a eight year old, nine year old, 1011 1213 year old, and I have like five days, four days, where you don’t have any parental responsibilities, and you can be totally focused on your spouse who also doesn’t have any parental responsibilities, you know, on like a day to day basis during that phase that is pretty unique. And, you know, from a relationship perspective was, you know, really kind of bountiful. I mean, it was, it was nice that because you don’t typically, you know, for most people, with kids, and jobs and spouses at that stage, it’s just 24/7 365 just wish it’s all together all the time happening in all stages, this is much more segmented. And yes, there are definitely some times I mean, you miss your kids hang out with them. And it’s, you know, you want to spend more time with your wife. But there was a lot of it that was really, frankly, pretty great and advantageous in terms of how it worked out and what it allowed you to do. As a person, you know, in various areas of your life.

 

Will Bachman  33:07

I want to ask you a bit about your, your work with startups, you mentioned that you enjoyed that aspect of being a counselor, beyond the purely legal aspects of it. Give us an example or two of, you know, where, you know, sanitize it, but where you played that role as counselor in the kind of value you were able to bring to some growing companies?

 

David Willbrand  33:33

Yeah. So, you know, what, what often happens if, if the relationship really works in its perfect configuration and calibration, and this happened, you know, quite a bit, I mean, I would say over the course of my career 3040 times, I would be in a situation like what I’m about to describe is that you’re sort of occupying this unique neutral space for the founder, like so. It’s incredibly stressful, to, to found and launch a startup company. You know, you are resource poor. There’s no roadmap, there are incredible demands. It’s really stressful. You’re doing lots of things for the first time, and you’re stretched and you have a lot of people coming at you from all directions. And so, you know, they are going to struggle with family stresses, financial stresses, general insecurity and impostor syndrome. They’re going to wrestle with co founders, they’re going to wrestle with their board and their investors, their employees, they have struggles with customers, they have no work life balance. And so they’re really, you know, kind of off kilter a little bit, you know, kind of half a bubble off in terms of just how they’re making their way through the world. So they’re not generally operating at their best as people and they don’t really have anybody they can talk to about that. Some, you know, find their way to therapy, which is a great, you know, approach. And then you know, some didn’t, or even those who do you still, you know, you want more than one, I can be a person that they can talk to, I don’t have like a day to day steak, I’m not their spouse, I’m not their kid. I’m not their co founder, I’m not their investor. Literally, I’m just a vendor. But I’m a person who is connected with all of these things. Because I understand what’s happening. Because directly or indirectly, I have visibility into all this complexity that’s happening in their lives. And I know the players, and I know what the situation is, but I don’t have, I’m not sitting there with a point of view, where I’m going to say, well, you need to do this, or you should do this, because I’ve got an agenda, right? Or a bias, I can just be a year, someone who can listen, and maybe someone who’s got some wisdom, just because I’ve seen this with other founders before. And for them, it’s their first time, for me, I’ve seen it 30 or 40 times. And you can develop a very close relationship and your walk with people during some I’ve, you know, had some people where I was the first call they made with some really awful personal tragedies, frankly, you know, terribly sad situations where they’re overwhelmed, and they don’t know who to reach out to, and they reached out to me, and, you know, that is to be able to operate in a space like that, in people’s lives is really a, you know, an honor and a privilege to be able to do that. And rewarding. So, you know, it, it was something that when I look back on that, you know, 20 year chapter of my life, that’s what I’m, that’s what I pulled the most from. And that’s what I’m, I don’t know if I want to use the word proud of stuff, but it’s, it’s what I value the most, from that experience, and from that professional stage in my life, for sure.

 

Will Bachman  37:00

And so, kind of giving personal advice, being listening here. Did you find yourself while an attorney ends? Do you find yourself perhaps just from pattern recognition? Also, just being a counselor on Oh, you know, here’s how you might think about doing business development or introducing them. Here’s some people you want to talk to you about your go to market strategy or your inventories for that area, you know, specific, you know, talk to this person about some technical aspects, you find yourself being that kind of connector or strategist?

 

David Willbrand  37:38

Yeah, absolutely. And I think that took some time. We, you know, I know this is gonna come as a shock, well, but generally, society looks down on lawyers. And, you know, there’s a sense that you’re in this profession where you’re just, you’re a parasite. And there’s some internalization of that, you know, among many of us, in the profession. And I do think that sometimes you, so it can be a combination of when you’re in those spaces that are kind of outside your particular specialty, to these business issues that you’re talking about, or organizational dynamics, or those sorts of situations, where you feel like number one, like it’s outside your pocket. And then number two, you’re just the lawyer, you know, what, what can you bring to this, these are people who are who are business, people who really understand this who’ve got the chops for it. And then, but just over time, to your point, pattern recognition is exactly the right way to frame it. And think about it, you just see a lot. And you, you know, we are built, we’re wired from an evolutionary perspective to be pattern recognition machines, and it shows up in lots of places. And for me, to your point, it showed up there, and so I could start to offer that advice, and provide that kind of feedback. And I started to slowly discover, like, Oh, I do have a unique perspective, oh, I have seen a lot of things that they haven’t seen that they haven’t had access to. And sometimes, it would be things that would feel obvious to me, that were incredibly value valuable to them. And then what you discover over time as well, they feel obvious to you, because you’ve seen that pattern so many times that it becomes obvious, but somebody else who’s never seen it, it’s not obvious. So you know, they’d ask you a question. And at first, you’d kind of be like, Well, I mean, there’s only one way to do this than that. And then to be like the lights go on that. Oh my god, exactly. That’s exactly what I need to do. Like, oh, that’s kind of neat. And, you know, it’s funny, because there were different times in places where I thought I need to figure out a way to monetize this. Like, I’ve got my legal skills, but they’re these other skills, and maybe I should figure out a way to monetize it. And, and I know some lawyers have tried, and they’ve done you know, some kind of consulting things or hybrid sorts of approaches, but kind of a breakthrough that I had along the way was you know, a lot of start upstart as you know what we call side hustles, right? People have a day job, something that they’re doing. And then they do the startup thing on the side for a while, until it feels like, you know, maybe this is something you want to throw yourself into. And we kind of call it side hustle. And, you know, I thought not everything has to be a side hustle. Sometimes things you can just do as a hobby, or for personal edification, because you like it. And there’s something freeing about that, like, you know, I know we’re in this like, dystopian capitalistic system, where we’re supposed to make money out of everything. But to sort of say, like, well, maybe I don’t have to, maybe I can choose just to do it to do it. And doing it as its own reward,

 

Will Bachman  40:42

you are allowed to do things that are just fun and not charge. They’re just

 

David Willbrand  40:46

fun and not charge for them. So that’s, you know, I did that was as part of my practice, I started teaching along the way. So I’ve been, you know, an adjunct law professor for 20 years. Right now, I’m at Michigan Law School, I’ve been at a couple of different law schools along the way. I’ve taught mergers and acquisitions, courses, businesses, associations, courses, startups and venture capitals, sort of my meat and potatoes. And that’s what I’m teaching at Michigan right now. I do a lot of work with different incubators and accelerators that are programs that are set up to help founders and startups. So the two where I spend most of my time now there’s Harvard innovation labs, that’s on the B School campus. And is there for people with some kind of connection to the Harvard universe. And then I spent a lot of time and energy with TechStars, Silicon Valley, as an entrepreneur in residence and doing work there with the different founders again, I mean, I get a little bit of money for teaching, and I get a little bit of money for being an entrepreneur residents, but it’s, you know, it sort of just covers travel, and you know, you don’t do it for the money, that’s for sure you do it, because it’s a, you got something that you can give back. And, and that’s kind of its own reward to kind of bring this piece of the conversation full circle. And that’s, that’s been really great. And I feel really lucky that I’ve had the chance to do that, and to translate some of my skills, acquired the hard way, and have a different place where you could share it.

 

Will Bachman  42:10

Let’s talk about Harvard for a minute. I’d love to hear about any courses or professors or activities at Harvard, that continue to resonate with you. You mentioned earlier that, you know, the courses and weren’t necessarily the high point for you, but what were some of the things that you’re involved in that, you know, continue to be important to you?

 

David Willbrand  42:31

Yeah, well, I think, you know, I would, I would say that I didn’t have like, that relationship with a professor or that particular interview, you know, interaction around a project or something that was that, you know, kind of lit me up or had some formative experience. But I would say, you know, I was a history major. And, you know, I think with a lot of these, you know, whether you were a gov major, or history major, or an English major social studies, a lot of them are similar in that what they would, what you’re really doing is you’re learning how to think critically. And that’s been invaluable. I mean, obviously, there’s a, there’s a direct relationship between thinking critically, and then you know, what I do in the law. So there’s a reason that a lot of people who have that undergraduate experience, emerge and go on to law school, and have successful legal careers, because they’re sort of hand in glove. But just in terms of, you know, the way you approach the world, I mean, it, we don’t have enough time to dive into it. But, you know, I went to college, holding a certain view of the world, culturally, religiously, socially, socially, spiritually, economically. That changed 180 degrees over the last 20 years, you know, I bet you could almost, it’s almost black and white, you’d say, I believe this when I was 17. And I believe this at 54. And it was a slow process, you know, of sort of unpacking, you know, inherited beliefs, and inherited points of views and inherited biases, and disassembling those, looking at the pieces, you know, and deciding what do I believe in why, and what makes sense and what doesn’t. And, and as I see the world, and as I see different pieces and have more experience and information, how do I feel about these things? And how do I put the blocks back together again, you know, that I wouldn’t have. I mean, that’s a hard journey to go through. Because it doesn’t those things don’t, they’re not extracted easily at surgery every time you do it. But it’s because of the skills that I picked up at Harvard, and in that particular concentration of history that I think, you know, gave me the tools to do it. And I’m really grateful for that because it’s it’s I feel like it’s made me a fuller human, and I’m more dimensional as humans, so that was really valuable. I also was very actively involved at Phillips Brooks House, as many of us We’re, I was connected with the homeless homelessness group, in particular, an initiative called boot salvage. And I would expect, they probably don’t do this anymore, because the school is probably decided there’s too much liability associated with it. But basically, what we did is we would take the trays of food that the houses cooked for dinner, but didn’t serve, they would otherwise be thrown out, we salvaged that food, and we delivered it to homeless shelters around the Cambridge area. And we, you know, fed 100 to 150 people every night with that excess food. And so that was a program that I started in, it’s just like a volunteer, doing it once a week and ultimately co chaired it with a couple of other people in our class, that huge responsibility for someone you know, 20 years old, do like you have people need to, you’re helping people eat. And if you don’t get this, right, because you flake out, or you don’t show up, or you don’t arrange the schedule in the right way, or you don’t fill a hole because someone else flaked out, somebody doesn’t eat. But, you know, to have that experience at that age number one to be exposed to that particular social issue was incredibly valuable, for all kinds of reasons, most of which I think probably don’t need to be said they’re sort of obvious. But just even frankly, from a skill set perspective, to if we were kind of running a form of organization, not really a business, but you know, there were elements, there were people, and there were deliverables, and you had there’s a supply chain, and there was a customer, you know, and you learned a lot from doing that. And, you know, I would say that, that those are, that was an experience to that was really invaluable.

 

Will Bachman  46:47

I don’t think we have time to unpack them all. But I wondered if you could give us maybe one or two examples of something you believed at 17 that you no longer believe today?

 

David Willbrand  46:58

Sure, so, you know, I went to Harvard having grown up in a conservative, evangelical Christian tradition. That, you know, first and foremost, that was our belief system, from a religious and a spiritual perspective. But of course that has, that bleeds into and has an impact on how you act and behave and view the world politically, and socially. And culturally. It’s basically sprinkled throughout my entire Harvard application, not even sprinkled, that was my Harvard application. And I think in that respect, you know, it’s funny, I mean, people, you know, have now use, you know, a DI hire in a in a way that is pejorative, but that was my dei element. For Harvard, they’re like, here’s a good big public high school, Cincinnati, Ohio, very conservative, very Christian, he’s very out loud about this true believer, that it’ll be an interesting dynamic to throw into our class. And, and that was my, that was my piece, right? That was my diversity piece. That’s what I brought to Harvard, and certainly believed it. And, you know, through my experience at Harvard, but through my 20s, and into my 30s, it just it I was I struggled with it at, you know, increasing, you know, level of dissonance. And was, I ultimately reached a point where I felt like, you know, I don’t think I believe this anymore, but that’s a very hard thing to push away from. Because it’s literally kind of baked into your DNA. I didn’t want to discharge it, it was my whole personal experiences, my family, it was my cultural environment, as people I knew relationships, what I did on Sundays, you know, I’d have a bad experience, they caused me to move in a different direction, it was just ultimately, I couldn’t hold the thoughts anymore. Because as I tried to unpack them, and scrutinize them and evaluate them, I just found that I just found them increasingly not believable, and not persuasive. So. And I would say, you know, everything from cosmology, to the theory of evolution, to a lot of existentialism, you know, was sort of the acid, you know, that I poured upon that belief system, and, you know, came out the other side. Having decided, I don’t think I can believe those things anymore. But now you have to decide what you do believe. Right? Because you don’t, you don’t want to just end up in a kind of a nihilist nihilistic culdesac. So, now, where are you going to do? So you go from there, and you, you basically put yourself back together again? What do I believe in? Why? And, you know, it’s been a slow process over time, but, and one that’s been, you know, at times painful and at times created some, you know, struggles inside my family, you know, as my, my parents and my family members have had to wrestle with that. But you know, they’ve been very respectful and I’m grateful. And I’ve been I’ve just come out with a very different perspective, in terms of how I see the world and the universe and our place inside of it.

 

Will Bachman  50:01

Well, what an extraordinary journey you’ve had. It’s a little bit of a shame that you gave up your promising career as a smokestack inspector. It seems so that you did find another route to go achieve impact in the world. Yeah. So much fun hearing about your, your journey for listeners that wanted to kind of see what you’re doing and where can they find you online if you want to share any links? Sure.

 

David Willbrand  50:31

So I am, will an active LinkedIn user, I have LinkedIn is like, I got on it early. And I love LinkedIn. And so I’m not on Facebook, I’m not on Instagram. I don’t participate in social media at all. Except for LinkedIn. And I’m not even sure of LinkedIn to social media, except maybe social media for dorks, which is probably why it suits me. But you can definitely find me on LinkedIn. I’m active on a regular basis, I talk about startup stuff, I talk about philosophy. I try to be funny, I talk about music from time to time, so I try to keep it a little spicy. And, you know, I have a very kind of varied approach to it, but pretty active, you know, in generating content and posting it there. So just find me on LinkedIn.

 

Will Bachman  51:18

All right, so we will include your your LinkedIn URL in the show notes. David, thank you for joining today. This was such a fun conversation. I

 

David Willbrand  51:26

really enjoyed it well, and thank you for the walk down memory lane. And I would expect that the single tag takeaway is you’re not going to talk to anybody else in our class that has that experience as a smoke tester. So that’s me anchored