#30: Rob Kramer of PurposeLab — Building resilience, an unconventional career path, and working w...

Welcome to From Startup to Grownup, the podcast. My name is Alisa Cohn. I'm an executive coach, an angel investor, and the author of From Startup to Grownup. Each week I talk to founders, creators, advisors, investors, and builders of all kinds about their insights and experiences in going from startup to grownup. Welcome to my episode today with Rob Kramer. Rob is currently running PurposeLab, a product development and venture studio that he founded with his partner Andrew Skinner. Rob is incredibly multifaceted and is truly a lifetime entrepreneur, starting when he was in his early 20s and he was a singer-songwriter. You'll hear how a mentor syndicated Rob and raised over a million dollars to help him launch his career. We spend the first part of this conversation talking about Rob's first entrepreneurial experiences, and I think it's a really wonderful illustration about how entrepreneurs think how they see opportunities and seize opportunities, and how they grow, connect ideas, and adapt. We then move to a very candid and raw conversation about some of Rob's failures, including a dramatic betrayal by a trusted business partner, which he calls the seminal event that woke him up. He talks about what it was like to be teetering on the edge, close to bankruptcy, and how he rebounded even stronger. We also discuss him meeting Travis Kalanick of Uber fame and what it's like to work with the Kardashians. This is a very personal and real talk conversation, and I know you're going to get so much out of it. So please enjoy my conversation with Rob Kramer.

Rob, welcome to the show. I'm so excited to have you.

I'm so happy to be here.

I'm so excited about this conversation ever since I met you at our meditation retreat. And, and I want to just say you are such a multifaceted person. You're an entrepreneur, you're an investor, you're a musician, you're a yogi, you're a meditator. So many things. Also, now you run, um, kind of an incubator. So I guess I'd love to start by asking you, like, what was your first entrepreneurial experience that you had?

My first entrepreneurial experience actually combined my, uh, early music career. As a singer-songwriter. I knew nothing about investing. I knew nothing about building companies, although my dad was an entrepreneur. So I always say that if my dad was a doctor, I'd probably be a doctor. And so when I was 22, 23, I was actually a journalist for a very short time, worked at CNBC. And what I really wanted to do is be a singer-songwriter. And I went to my mentor and friend, Tom Carter. We were living in D.C. at the time, and I told him my dream, and he said, well, how are you going to do that? You're going to go play Holiday Inns for the next 6 years? And he said, here's what we're going to do. We're going to get a demo recorded for you. We're going to try to get you a record deal. He started managing me, and we're going to raise some money for your career. We're going to syndicate your career much like they do with golfers and with horses.

Wow.

I said, what? Hold on. Need to go to the Webster's Dictionary. Syndicate. What does that mean? Is that like a, is that like a mafia thing? Is that a syndicate? What, what, pizza parlors here? He says, no, we're going to sell pieces of you. I'm like, which pieces?

Okay.

So he raised, and this is like, you know, I figured out in today's dollars, this was like in the late '80s. In today's dollars, it was like over a million dollars.

Oh my God.

It was like $350,000 or $400,000 in those days.

This is before NFTs, people. This is before fractional ownership was a thing. I know. What happened? How did he do that? Do not skip that story. Well, why did he even think, no offense, but why did he even think that you, a 22-year-old nobody, should deserve to be fractionalized?

Well, funny enough, I asked him. I asked him the same question, actually. The truth is, and we talk about entrepreneurial experience, the career ultimately got a record deal, did the whole thing, moved out to LA. The career ultimately was a failure because the record never went anywhere. And I was really not interested in going to the next one and being a starving artist, et cetera. But through that point, we had successfully raised money for some pretty amazing people. Like the, um, heiress to the Maybelline fortune and a senator from Texas and doctors and lawyers. And it was unbelievably— it was unbelievably incredible because he created this prospectus for the limited partnership and he did this really ingenious thing. He had the, uh, in those days there was no internet to speak of, and he had the prospectus leather-bound with gold embossed letters. I kid you not. And I'm like, your presentation of me is way more impressive than my presentation of my talent. Like, because I'm a 22, 23-year-old, you know, yearling who is just getting out of the gate and I kind of suck still. So what I learned, I actually learned about business and entrepreneurship and what it takes to kind of persevere with a very unique business model. I mean, no one had done this before with a singer. Uh, and in fact, we had articles in Variety and Hollywood Reporter and my hometown newspaper in Pittsburgh and, and Regardez magazine in Washington, DC and all these places. And I used to read them and I was like, yes, the business model is way more successful, at least in terms of raising and getting it syndicated than my career. So you learn from the failures and then you learn what your strengths and what your weaknesses are.

What did you learn about your strengths and weaknesses and how did that then propel you into kind of your next chapter?

Well, I'll tell you, I learned a lot from him because this is a man who literally taught me to never take no for an answer. In fact, it was truly the early days of understanding and learning that one more no is just getting you that much closer to a yes. So I went from there to wondering what I was going to do because I'd never really— I mean, I had jobs, you know, in high school and things like that, but I was like, I don't really think I'm fit to work for anyone. And my dad was an entrepreneur, as I mentioned, and I thought, well, maybe I could figure out how to start a company. I think I had enough sort of self-confidence in that area. And I ended up starting a music video and commercial production company here in LA. And within a month, we got super lucky. Didn't really know much about it. Founded it with a couple of director friends and we were off to the races. And we had our first major label visit video with a band called Fishbone. And it was Columbia CBS Records. And we went from there and did that for like 3, 4 years. And till that whole business sort of fell apart, not our business, but the the music video industry at large. It was sort of the last heyday of music videos, super early.

Now you did mention your dad. Let's just back up a little bit. What, what did your dad do? Like, what was he under? What did he entrepreneur? What did he found?

What did he entrepreneur? He, um, so my dad, before I was born— my much older brother and sister— before he was born, he founded, um, furniture stores in Pittsburgh where we grew up and, um, had those till I was around 11. And this was a very seminal experience. Um, at 11, my dad went bankrupt. And we went from having, you know, a decent amount of money and a couple of family vacations a year to literally pinching pennies on the kitchen table and wondering what dad was going to do next. And he was a very creative entrepreneurial guy who was always a little bit ahead. And he had read about a California company that was silk screening on t-shirts and putting companies' logos on t-shirts. This is like, you know, super early on. And he's like, I'm going to form a company in here in Pittsburgh. And we're going to have the first Pennsylvania silkscreening company. And we're going to go out and we're going to get sports teams and companies to put their— and they're like, you're crazy. We're Jewish. And my dad's American name is Stanley, but no one called him Stanley. They called him by his Jewish name, Zundi. So he's kind of like, everyone knew him as Zundi. And it was like this iconic name. And like, Zundi, you're crazy. What do you mean? You're going to put— who's going to pay you to do this? No one's going to pay you. Meanwhile, every sports sports team, every company. He just built this incredible business and became a family business. I didn't have to think very much about doing it. I didn't know how I was going to do it. I didn't know if I had the chops to do it, but I instinctually knew that I could probably at least try. And if I failed, fine. But it felt really comfortable.

When you say, if you failed, fine, again, that's a very— that may sound normal to you, But actually, a lot of people are nervous about failing.

Yeah, this is why most people don't become entrepreneurs. You know, one of the, one of the ingredients in the recipe to becoming a great entrepreneur is no one loves to fail, right? No one wants to fail. But you might fail. You're starting something that hopefully is forward-thinking, and you're taking a huge chance, and you're trying to convince people to actually believe in you and back you with money, et cetera. And, you know, it's become a trite sort of saying in the days of, you know, we're in the era, great era of entrepreneurship. You know, you learn most from your failures and you just, you can't be afraid to fail because those are going to be your greatest successes.

Totally. So what did you learn from the failure of the, of the music video company?

Well, I don't know that the music video company really didn't fail. The industry failed. The music video company got wound down. So I don't know that that was a— I don't know, it was bona fide, you know, roaring success, but it certainly wasn't a failure. It was just more of like, okay, time to focus on some other entrepreneurial experience. So then kind of regrouped, looked at some options. This was mid-late '90s. There was this thing called CD-ROMs. And so I formed a company called Moving Pixels with a very close friend of mine, and it was a Essentially a 3D animation studio that essentially was an interactive design studio that used 3D animation to create kids' edutainment interactive CD-ROMs. And we used to do this for big movie studios and big publishers from, you know, MGM to Broderbund. It was quite, quite great and did that for 7 years. And that industry changed. It was around the time when the internet was really revving up and we morphed that company to a visual effects studio for commercials and movies and music videos. And that was less interesting to me, was great for my partner. Sold my half of the company and moved on.

And was that a hard decision to make, to sell your half of the company?

It wasn't, uh, and this goes into, uh, sort of the top of the show when you referenced, um, my dizzying sort of, uh, multiple hats that I've worn, uh, professionally throughout my career. I was very much into getting back to music and I was starting to do professionally, uh, not because I wanted, because I fell into doing some voiceover work. And, and it was like, oh, I want to get back to doing that kind of more performative kind of stuff. So I was really ready to move on.

Got it. And so then did you go into more performative kind of stuff?

I did for a little while, and I recorded a new sort of demo— wasn't a record because it didn't have a major label behind it, um, and, uh, did that and then realized oh shoot, we're back to being the guy who's trying to be an artist and trying to make money at it. And this is not a good feeling. I, I'm, I've always been sort of creative and entrepreneurial, but I feel much more grounded when I'm actually making money. But, you know, I don't ever like making money for money's sake. Like, that's the choices that I've never— I'd like to believe I've never made in my life. It's not about that. It's about the experience. It's about the journey. It's being passionate about what you love to do. I've never felt in the last 25 years that I have a job or I work. I just get up and get to be playful and passionate about the things that I love to do.

Mm-hmm. I love it. Sounds like what you said is that you sort of went again to try to be a performer, and then you were like, you know what? I don't want to be a performer. This is not working for me. But you had to then find something else you were going to go do. And so where did you go from there? Yeah.

I spun up an idea to create what ostensibly can be described as GarageBand, Apple's GarageBand before GarageBand. Um, we found this Russian technology called JAVU, which was this incredible codec, and I was going to create GarageBand. And it was the, the, the, the product model was that people would be able to edit video and mix music in real time. With each other collaboratively around the world. The codec and the bandwidth just weren't there, but I had met a guy named Ian Clark who was a young guy out of Edinburgh. He had created an open source platform called Freenet, which was a peer-to-peer distributed computing platform. And he was using it to sort of, as he would say, help dissident Chinese novelists get their novels out of China.. And it was like his thesis project when he was in college. And I was like, oh, I can use that file sharing platform to help people on this. It was called digdag.com, digdag, and to help people file share their audio and video files. And I reached out to him. And then when I met him and I flew to London to meet him, I was like, oh, wait a minute, there's a much bigger opportunity here. And the opportunity is to create what at the time, uh, we thought was going to be another type of Napster. And, um, we spun up a company called Upriser, which was a peer-to-peer distributed computing company. It was initially focused on the entertainment business until we realized that we, unlike Napster, did not want to be finding ourselves in court, um, you know, 5 days a week. And so we created a peer-to-peer software company, essentially Napster for the enterprise. And, and Intel was our first investor investor. They were very interested in this kind of technology, and they invested in two peer-to-peer companies, ours and Travis Kalanick of Uber fame, uh, Red Swoosh. And there was a moment, in fact, uh, when, uh, Travis came to our offices in Venice Beach on Abiquini, and, um, we had talked about a possible merger, um, and, uh, that never happened and probably wasn't the right thing. And Our company sold a few years later, and I think his probably sold for a little bit of money too. And, um, that was it. I handed over the reins, the CEO reins, after a few years. We had done a Series B to a more, you know, professional CEO. Um, and, uh, and then wound down my time there and, um, took a little time off to decide what I was going to do next.

You were— needed some time off, it sounds like. But then how did you then— where did you then go to?

So I had a very, very, um, like many of us now, a very intense addiction, if you will, to politics. I was a, you know, a junkie, um, so to speak. And, um, I decided what the world needed was a, um, social network for taking political and social action. Now, this is like 2008, 2009. Obama's getting elected. Facebook is now a thing in a big way. And with my own money, I designed and built this thing and then looked around and was like, okay, need to raise some money now. Bad timing. This is one of those bad timing situations because Facebook had some traction in that area, big traction. And then Obama and his folks who then later became Blue State Digital, formed an agency and they did that whole thing. So I was like, okay, good idea, sort of right timing, but wrong sort of legs. And, um, we morphed that into a company which was the precursor to my current company. Um, Purpose Lab was just a name change, but it was called Pop Rule. That was the name of the social network. And we basically morphed it into a studio, uh, to ideate, design, and build apps for taking political and social action. So for elected officials and candidates and nonprofit organizations and advocacy groups, et cetera, et cetera. And we did that exclusively for 4, 4, 4 or 5 years until I realized that, boy, politics and technology is super hard. And it's not that— I mean, it's very effective now. Obviously, we, you know, people win races this way. But from a business model revenue perspective, just exceedingly difficult. So we kind of evolved and started doing some more commercial stuff and we boomeranged out and said, we want to do the most commercial thing possible so that perhaps we can then learn from that and then apply that to political and social action, sort of audience building and apps and things like this. And so we did that. And Purpose Lab is 12 and a half years old and We moved into a venture software studio model about 5 years ago, which was an incredible sort of enhancement for us. So that's what we're exclusively focused on now. And we went from doing apps and platforms for political and social action, and the boomerang was we found ourselves designing and building all of the apps for the Kardashians and the Jenners.

I was gonna ask. Yes, I was on your website and I was gonna ask about the Kardashians and the Jenners.

So I am, needless to say, I am incredibly conflicted, um, but honestly so. So I knew people who'd watch that show. My wife watched that show and I was like, why do you watch that show? It's like, it's like wallpaper. It's like, it's like, you know, watching something that you don't have to think about too much and And you know what? They are incredible entrepreneurs. And I'm like, come on, that's ridiculous. So one day I showed up and I said, hey, to my wife, I said, you're not going to believe this, but we've just been asked to build all the Kardashian and Jenner apps. And it's a huge project, as you can possibly imagine. And he said, what are you going to do, Mr. Anti-Kardashian? And I'm like, I don't know, but it's a hard one. And it reminded me of a thought that a friend of mine became a very big a television movie director, said to me once years ago, uh, when he was making movies, he would do a studio movie and he would do an independent. And he'd say, for the studio movie, one for them so I can get one for me. And I thought, okay, yeah, one for us so we can make a bunch of money, but also informing ourselves of what this very crass commercial sort of thing could be. I have to say that they are truly, whether you hate them, have disdain, or you think they're the greatest thing ever, they're incredible entrepreneurs. And, you know, we met all these fans who, when we launched this thing at the Apple Store in SoHo in New York, um, who people came and they, for the, for the app launch, it was a very big deal. And we talked to these people and like, these people are there willingly. They, they love these Kardashian-Jenner sisters, and apparently they were not a Paris Hilton fluke, right? They've been around for a long, long time. It's their entrepreneurship. It's their entrepreneurial spirit. It's their desire to keep in their lane, building and creating, and in Kylie's case, becoming a billionaire through her makeup company.

My goodness. Yes.

So let's, let's take a breath.

The comment that preceded that was, we decided to go as commercial as we could. And that's when it flashed into my head. I wonder if I'm going to ask about the Kardashians. And yet there we go. As commercial as you could. There you go. So I have to really say, first of all, have you met the Kardashians through this experience? Yeah. And what are they like?

I mean, I don't know them well. Um, But they're everything you would possibly imagine them to be. And then incredibly intensely focused and committed to what they do. I mean, you can't argue from an entrepreneurial perspective. You cannot argue with their commitment and their success.

Yes. And when you said, you know, as entrepreneurial as they get, I mean, literally to build something from nothing is kind of the definition of what they've been able to do, which is extraordinary.

Based on nothing.

Based on nothing. Exactly right.

I was really—

I was noticing that all your previous, you know, things, ventures had lasted like a year, 4 years, 3 years, 4 years. It felt like, you know, these sort of chunks of time. And this has lasted 12 years. And I was going to ask you, why do you think this has been more, had more staying power?

Yeah, it's a great question, and there's a couple of answers. First of all, I used to say prior to this and prior to my marriage to my wife, which is also 12 years old, um, that my longest relationship was with yoga. That was my longest one because I've been doing it for like 20-some years. Pretty regularly. And I don't know that that's a very proud thing to be proud of, but there was a moment, and we talked about this briefly offline, about 14 years ago. I'd done pretty well. I'd had some decent amount of money in the bank, but all of my money and all my finance investments were outsourced to one individual who was business manager, accountant. And, um, he, uh, we were investing in something and we thought it was legit and it wasn't, and it was a Ponzi scheme. And he stole $67 million from about 120 of us. And, um, he wiped me out. He put me 7 figures in debt. And on the first birthday after I met my wife, We had a birthday party she threw for me at my house, which I was losing at the time to— it was going to go into foreclosure because, although thankfully I did not lose it ultimately. And I had— I was 7 figures in debt and had $11 in my bank account. That was the seminal event that woke me up.

Yeah.

Now, all of the things that I had practiced along the way through yoga and meditation and entrepreneurial experiences, successes and failures, they sort of culminated in this defining sort of what I might describe as a phoenix rising moment. And truthfully, and I say this to friends and colleagues, if it wasn't for my wife, Standing by me. I don't know that I would have survived it. Um, and, um, it really woke me up to all of the, the Achilles heel part of my personality and of how I approach things. I mean, you're right. It went from 2 years to 7 years previously in my entrepreneurial experiences, but I was like, oh, I'm middle-aged now. And this is not going to look good in 10 years. Like, if you keep doing this, like, it's just going to be— you're going to be, you know, a hamster on a wheel. And what are you going to have to show for it? And you're not going to feel good about that.

Yeah.

Well, I was forced into waking up to a new way of approaching. It wasn't that I was, you know, interested in not doing creative entrepreneurial things. To the contrary. I had to make a very conscious and sometimes painful decision to say no to my instincts towards allowing myself to do other kinds of things surrounding my main entrepreneurial experience, right? So I might be doing building a business, but I might be doing 3 things on the side, right? It seems like I'm doing that now, but it's in a different sort of— there's a different modality that happens. There is an organizational structure even in my mind, which is like, no, that's in third position. That's in fourth position. If first position and second position don't get priority and they're not complete, or you haven't followed through on that, ignore third and fourth position because they're not— they're only going to take away from my focus and priority.

Yeah, it's like You're now more maybe in control of that side. I don't know how to use the word control, but at least you're more in harmony, let's say, with that side.

Yes.

And more clear on it. So there's so much to say about this. Like, what went through your mind when you realized this guy has stolen my money? And also, I'm in— and I'm not sure if the same thought, but I'm in 7 figures of debt. But what went through your mind?

I'm fucked. I honestly And I don't mean to be glib about this. I really thought this was the end. Like, how am I— I was in my 40s and like, how am I going to— how am I going to come back from this? Like, this isn't about like, let's start a new company. And, um, in fact, I was— it was in the beginning of starting Pop Rule Purpose Lab. It wasn't about just like, we are at zero, at par. This was like, I have to do this company thing and I have to manage debt and I have to save my house and I actually can't afford to put food on my and my wife's. And I had a kid who at the time was 8 years old, 9 years old, although shared with his mother. So I wasn't full-time all the time, but I didn't know. How to do it. And I was like, wait a minute, you have apparently all these skills. Like you've been meditating for years. You've gone to these 10-day meditation retreats. You yoga committed, you know, you've, you're committed to many, many things that should be skills that will help you. And when faced with it, one is confused. One is lost. One is depressed. I'm not a depressive person. I'm a super optimistic person, but I got depressed. I was like, I am fucked. And like I said, back to my wife, Tori, it's like, if had I not had her in my life, I honestly, not to be morbid, I just don't know how I would have made it. And she threw books at me to read on money and, you know, the story around money. There was one book by this author T. Harv Eker called Secrets of a Millionaire Mind. And I read the first 10 pages, like, fuck, this is This is an infomercial selling me shit. I don't want to be a part of this cult bull. I don't need this. And she's like, read the fucking book. Read the fucking book. And I read it and I was like, this is painful. Just read the book. And I read it 3 times. And by the 3rd time, I was like, oh shit, that's my story. And it hearkened back to time I was 11. My dad went bankrupt.

Yeah.

And everyone said to me, my friends, my lawyer friends, 3 bankruptcy attorneys who I'd visited, you have no choice but to go bankrupt. You have no choice. And I remember saying to the third attorney, I said, you know what? I think you're probably 100% right. You're the professional. You've seen this before. I don't know how I'm going to do this. I am not going bankrupt. I am going to break that. And my brother went bankrupt too, by the way.

You know, when you said about this and how you lost the money, I thought about your father.

Yeah.

This family history. Yeah. And you were like, I'm going to break that. And that was what the book told you. Is that what you're, what you got from the book?

No, the book didn't tell me that. But instinctually I said, but I loved my father. He was an incredible man. Loved my brother still to this day. We have a great relationship, but I was not going to go bankrupt.

Yeah.

I didn't know how that was going to be possible. I just wasn't going to do it.

Yeah.

And I was going to find another way. And thankfully, through friends and family and my wife and having the spirit of entrepreneurship, truly, because that was the only thing they knew how to do. But for the first 3 years, 4 years, perhaps first 3 to 4 years, I was still playing victim. How can this happen to me? And I can't believe this. And I was angry and upset. And one morning, like an epiphany, I woke up and I said to Tori, there's only one way. Like, I'm managing this debt and I'm negotiating debt away and I'm paying debt down and all this other stuff. And I thankfully restructured the financing of my house and was able to save it. I was like, there's only one way to do this. Make a shit ton of money. Like that's the only way out. You're focused on debt. Focus on abundance. Focus on making more money than you've ever made in your entire life. Of course, I would never give up doing what you love to do, but do it at a higher level. Do it better. Do it faster. Do it stronger. Do it, you know, hey, stamina.

Oh my gosh, I love it. So, so how, well, so many questions, but like how specifically and tactically when you kind of had this realization, it's almost like hitting bottom. I do kind of have a sense of hitting bottom, right? That— do you feel that way?

It was below bottom.

Yeah, yeah, I can imagine. And it was a wake-up call.

It was, it was not only wake-up call, it was a gong being hit over my head and reverberating throughout every cell in my body.

Yeah. So how did you, like, tactically put foot in front of the other to then emerge from that?

So, a number of things. Well, one of the things is I realized I knew how to make money. I didn't know how to manage or invest money. I always outsourced that. My dad was the same way. My dad knew how to make money. He was a horrible money manager and he happened to be one of the most generous human beings on the planet and would walk into a restaurant. He was a very sort of popular guy. He'd walk in and he'd buy everyone dinner. And he was doing this at the time when he was bankrupt. I'm like, where are you getting— like, my mom was like mortified. And I was like, okay, so I needed to become financially literate. So I set out to do just that, to learn about investments, personal investments, to learn about— like, I had a little— I had some retirement money. Money left, and I had to spend all that to survive. And so I knew nothing about this. And I said, I am going to become a mini expert on this for me. I am not going to outsource this to anyone else. I'm going to learn. And the only time I'm maybe going to let some other advisors come in is when I am articulate and knowledgeable about this space. So I started literally creating spreadsheets. And the spreadsheets, unfortunately, in the beginning were managing my debt, right? Because there were like 12 or 14 or 15 accounts that I had to manage. And so, as I like to say, my spreadsheets now have spreadsheets. Like they've given birth. Like I think we're in the third generation of spreadsheets. I have spreadsheet grandchildren now. And I am incredibly, I am proud to say, I'm OCD about this, unbelievably OCD. I look at these spreadsheets every single day and you say, well, what are you looking at? I'm literally managing and updating them. And what I learned is I learned about portfolio diversification and I learned about asset management in terms of like, you know, you should only put 5% here and 20% there and so on and so forth. And I got lucky. In being much more disciplined. I got lucky because, as my favorite definition of luck— luck is the residual of design, right? So you can't just go out and manufacture luck, but luck will happen. It will be the residual of the design, the framework that you put into place. And, um, uh, I was doing extremely well. Um, it just kept getting better and better, and I was able to manage it and Um, I was disciplined about focusing on the one thing. And in this particular case, the one thing was Purpose Lab.

Mm-hmm. Got it. So it sounds like when you're talking about sort of just educating yourself and managing your debt and your spreadsheets, it's like you had different accounts of debt. You somehow had negotiations with the people on the other side of that debt, and somehow one way or the other, they were willing to give you more time, let's say. And then you were able to pay it off over time. Is that kind of just fundamental the way you managed it?

So the first thing I had to do, as I mentioned, was to refinance the house. And this was under the Obama refinance program after the 2008 crash. So this is around 2010-ish, 2011 maybe. And, um, only 3% of the people that actually applied got it. And I was like, by hook or by crook, I'm going to be one of those 3%. Um, and got super lucky and was able to refinance the house and save it. Still have it now. It's a rental property, which has, um, been wonderful thing. And, um, And then, but it was mostly, um, I had a, um, I had an equity line on the house and I had credit card debt and it was mostly that kind. So these are big, huge corporations. These weren't, I didn't have any personal loans to anyone and I didn't borrow any money from anyone either. Um, uh, and so it was like if I had $100,000 in debt to one company, I negotiated down to $35,000 or $70,000 to $20,000, or there were a couple that I had to actually forego. I couldn't handle them all. And I was like, okay, credit, you know, um, um, uh, report's gonna take a hit and it'll be a bunch of years. And, um, and then I started setting— this is something that I never did. I started writing down my goals. And I always just sort of frown upon that and think, oh, that's just made up. Fictitious bullshit. Well, apparently it's not because I've been doing it for like 7, 8, 9 years. And you don't always, I mean, create stretch goals. You don't always hit your goals, but what it does if you keep checking in with them is it creates a framework and a roadmap, something to look towards, something to work towards and get to see, well, how far off am I from that particular goal? What did I do last year? What do I want to do this year now? And so I started doing that and, you know, talk about sort of residual benefits. There are some deep, deep residual benefits of doing that.

What, so what did you, what were your first, when you first started setting your goals, what were some of the things that were on the goals list and what were the residual benefits?

Well, I could tell you the first thing was to get the fuck out of debt.

Totally.

Yeah. I mean, and then that happened and I was like, oh my God, I have no debt.

Right.

I have my house. I have my mortgage still. In fact, the, the debt on the house was more than I bought the house for, but that was fine. It was crazy. I could handle it. Um, and, um, and some of the goals were like, I wanted to own more real estate. Um, uh, we had moved like 7 years ago and started and fixed up and remodeled that house that I was going to lose that we now have as to a rental property. And then we got another rental property and it was like, okay, that's something that I knew nothing about. I wish I'd started that in my 20s. 'cause, you know, that was a dumb thing. But that was just pure ignorance, like not understanding it. And then there were goals around, you know, revenue and PurposeLab and growing and doing more projects sort of more efficiently, perhaps better margins, but fewer projects. Like we were never interested in being like some agency model that had 100 projects and 100 employees. Like that's never been my thing.

Yeah.

So just, you know, building from there. And I— what I really understood for the first time in my life, that you can skip a couple steps, and I was always good at that, but you got to build the foundation brick by brick.

Yeah.

And there's no skipping a brick.

Yeah.

Right. So it was really getting into the mindset of truly reveling in and immersing myself in the step by step by step, that the incremental growth will accrue to real advancements. And then the giant leaps happen.

For purpose, like, what does that mean tactically speaking? When you say brick by brick and the incremental then leads to the exponential, what's an example of that?

Well, I mean, I think that You know, we, one of the things we did is we virtualized the company actually about a year before COVID So sort of a little bit ahead of the COVID curve, which reduced some of our costs certainly. And then we started looking at projects that not only would we say no to a lot of things, but we said yes to things that we knew that even in the most challenging moments of a project, as all, as many do, that we were in it for the long haul. So it was really about actually getting out there from a biz dev sales perspective a little bit harder than I had been because we had, you know, I had a network that, you know, paid dividends, but it paid dividends only up to a certain point. So I had to stretch myself in terms of getting out into the market. And that was one of my roles and responsibilities. And then just managing resources and managing developers, in our case, in a way that just was more efficient, being a little bit more rigorous in our approach to creating frameworks and environments that enabled us to just work more efficiently, truly.

Yeah. And also maybe just with a different kind of standard, or maybe feels like almost like less tolerance for people slacking off or whatever. It felt like— it almost felt like, to me, on this side of the screen, it feels like We just got, like, I just got serious.

Most definitely. I had no choice but to get more serious. This was one of my sort of, I think, um, Achilles heel, I suppose. But is that, um, I knew I was talented at various things and I knew things came relatively easy to me, but I always hit that wall and then it'd be like I'd either quit at that moment, or I push through. And so here I was, there was no choice in the matter. I was either going to die and give up, or I was going to push through the discomfort.

Yeah.

And the discomfort was more than your sort of average discomfort because I was in financial pain. I was in emotional pain. And intellectually, I understood, but I didn't know how to apply the intellect to overcoming these obstacles called financial and emotional pain based on the experience that I had.

Right. Right. I'm wondering how much do you think that your training at that point in minutes, because you maybe describe a little bit more about your meditation training prior to this and how that maybe played in, and maybe yoga if that's appropriate too.

Yeah.

So, look, meditation and yoga are practices over time. If you practice, as I did, certainly yoga every day for 20 years and meditation for many years every day, they are practices that you do not for the purposes of getting the benefit but for the purposes of experiencing things as they are, not as they appear to be, which is, in fact, the definition of the technique called vipassana, which I do. Vipassana is a Pali, old Pali Indian word, which means seeing things as they are, not as they appear to be. So, I would go on these 10-day silent meditation retreats, 11 hours of meditation a day, 110 hours In 10 days, unlike our current forms of pop meditation, and I think Headspace and Calm have done an incredible job of opening people up to this, to do meditation with the goal of getting something, to me, is antithetical to why you do it. Much like I mentioned earlier, growth, exponential growth happens in my experience from incremental, consistent growth, you know, growth over time, small increments. And that is the practice of meditation. And that is the practice of yoga. You don't see exponential growth, you experience incremental growth and wake up one day and go, oh, I can stretch more deeply, or I'm less reactive than I used to be, or I'm less angry, or whatever it might be. And you wake up and you go, oh, I don't do that anymore.

Yeah, I think I've experienced that myself. I've experienced that myself. I mean, like, it is, it's a very interesting thought that you don't notice it and then all of a sudden you do notice it, right? And, and yet It must— you must have— it sounds like you called upon it during this difficult time of the restructuring and whatnot.

Most definitely. And I think that because I've been meditating and doing yoga for most of my adult life, it's always there. It's there when I want to, you know, scream at the guy that just cut me off on the freeway.

Yeah.

And I don't 99% of the time, but because it's there to call upon always, because like every practice that you've been doing for years and years and decades in my case, it is part of your cellular structure. At least that's what you hope. And it's been the case in many instances. It certainly looked like it failed me miserably when I was crashing and burning when I had all my money stolen. But it was there. It was just obfuscated and buried below all of the trauma that I was experiencing.

Yeah, totally. And you said that Tori was obviously was very instrumental. What specifically, besides her throwing a book at you, what was, what was she instrumental at for you and your support?

Well, first of all, she is a very even, level-headed thoughtful, intuitive human who is full of love. And, um, I had said to her about 2 years into our relationship, when I was in the burning throes of this, I said, look, you don't have to do this. And I meant it. You should go find someone else. This is too difficult. Like, you shouldn't have to do it. And the most incredible gift that I think I've ever received in my life is And this woman says, my wife says to me, oh, and we were not married at the time. We were maybe about half a year to a year away from being married. And she said, why would I do that? I am here to be your strength and your rock and to stand beside you because you're going to make it through. You know how to make money. You know how to build companies. And oh, by the way, you're just in a really, really difficult place. And you can't see what I can see. And she believed in me way more than I believed in me, I can tell you that.

Wow, that is quite a gift.

It was quite a gift.

I can imagine. I, I'm so, um, I'm just so in awe always of people who can also give that self-portrait, right? Like, you needed a different self-portrait and she was there to give it to you and to see, to her point, exactly what she said, to see what you could not see.

100%. Yeah, 100%. I, I was— there were so many things I was, you know, not seeing and, and sort of ignorant and blind about throughout my life. And this, as I said, this, this event in my life, uh, shined a floodlight on and exposed all of those things. And then she was there to kind of keep the light focused so that I wouldn't miss it, right?

Wow. And did you— I mean, were there other things that you sought out to help, you know, support you during this? Like, did you seek out therapy? Therapy? Or like, how else did you go about the healing that you needed to?

I did. I was in therapy at the time. I'd done a lot of therapy in my life. Never really, I mean, it helped sort of, I thought, temporarily, but I'd always find a way to talk myself in or out of something. But I had this incredible therapist here in LA, John. And when I was going through this, had gone through this theft loss, I was very paranoid about a lot of things, meaning like, well, what if that happens? And then what if that happens? And what— he's like, hold on, like, you come in here every week and you tell me 1,000 stories that might all come true, and most likely none of them will come true. He said, I guarantee you that whatever happens, bad stuff, good stuff, You are not going to know how you're going to respond and react to it until it's presented to you. So don't waste your time coming up with 1,000 fictitious stories which are meaningless. You will meet it as it arises. And right then in that moment, I was like, holy shit. Like, talk about, you know, being in the now and talk about being present and talk about, you know, just observing things as they are, not as they appear to be. And I created a lot of appearances in my mind. That one statement was worth all the years of therapy. And in fact, it really helped to change one of the many things that helped change my life. And I see, I meet things as they are. And when they come up, that doesn't mean that I don't worry about stuff. I worry a whole lot less. I remember once my mother who was, you know, just, you know, the stereotypical loving Jewish mother, she worried about everything. And I was like, Mom, I said, why do you worry so much? Like, why are you worrying about that? And she's like, because I care. And I said, mom, when did you start equating the definition of caring with worrying? Like, those are two different things. So I stopped worrying and caring about when they would arise and then doing something about it.

I love it. So now you're doing PurposeLab and it sounds like, I mean, you know, This is a very dramatic moment, of course, and it was a wake-up call, like you said, and we hit below bottom. And then you, I mean, there's nothing like pulling yourself out of a hole like that to give you a sense of probably realness. And I guess I would ask you, now you're on the other side of that, what else did that give you, that experience?

Well, you say that there's nothing like that. I wouldn't wish this experience on my worst enemy. It was the best thing that ever happened to me, right? Might not be the best thing for any other people, but it was the best thing to happen to me. It was truly a gift being on the other side of it. I don't take anything that I've created in the last 12 years or so, 14 years, for granted. I don't take for granted that it will get done. I make sure that I'm constantly, consciously, physically showing up intellectually, physically, in as much integrity as I possibly can to ask the question, am I being responsible? Am I in integrity? And am I doing enough to actually follow through on the thing that I said I'm committed to following through on?

Yeah. Totally. And do you have a business partner now?

I do. I have the same business partner and his name is Andrew and he's a spectacular human being. I met him and hired him as a developer when he was 23 years old and a year and a half out of Brown. And then I realized, oh, this guy isn't just a brilliant developer. He's an incredible human being. He is, he will be 36, I think 36 in December, and we have been partners ever since.

Wow.

It's an incredible part. So he and Tori and Purpose Lab are now my longest relationships. So, wow.

Really? It's like so healing. And so I guess I'm curious, like, if I think, how many employees do you manage at Purpose Lab?

So we have a, we have a very distributed model now. We bought into, so we had about 18, 20 people here in LA. And then we were growing, and so we bought into a company in Eastern Europe that was doing some overflow work for us. And so we have about 60 people, um, but it's very, you know, we're in the software business, so everything happens in pixels and code, although the projects happen obviously human to human. But, um, it is— we, we've, we've just built a system that is incredibly efficient after all these years, and it's, um, it's, it's, it's very well managed.

That makes sense. And so it's a well-managed machine and a well-oiled machine. Do you think about sort of culture and, and the culture of the environment around you?

So I used to much more when I had Upriser, the peer-to-peer software company, because we had 30, 40 people in the same location. Um, I will admittedly say, and if people are listening to this who were actually part of those experiences, I I am not, I don't like managing people. I just don't like it. Yeah. I'm, I'm, I don't consider myself very good at it. I want to move too quickly. I want things to happen. I want to think outside the box and that works on a lot of levels, obviously, as an entrepreneur and building a company, but it doesn't always work in terms of managing people who are evolving at their pace based upon their position in the company.

Yeah. So that makes sense. So what I see you, especially in this whole discussion, I mean, I definitely see you as a creative. And as we've already talked about, you're doing multiple different things right now. Purpose Lab being, sounds like thing one and most important thing that's taking your attention and that has to be working. So it sounds like the rhythm is that's working and has to be working, but there are other things that you're working on also that are kind of scratching the itch of creativity and also back to your social conscious. Could you talk about what some of those are?

So, well, the one thing that I'll mention is I have a cousin, second cousin once removed, who is a physicist and a machine learning expert and a biomedical engineer, and talk about, you know, multi-disciplined. Um, uh, he created a breakthrough in an area called forensic genomics, and he created an algorithm which, for, um, sort of easy, uh, definition, has the ability to, uh, when applied, exonerate falsely accused and convicted people through DNA and this algorithm which is called, um, it's called mixed contributor deconvolution. Basically, it's mixture analysis for DNA when there's more than, uh, a single contributor to a particular crime scene. Uh, he called me up and said, hey, look, you know, I apparently did this. He was at Johns Hopkins. University at the time and working at Applied Physics Lab where he created this. And he said, like, I'm either going to write a paper and publish it and be done, move on with my physics career, or maybe you can tell me if there's a company here. And, um, he got me up to speed after a few months, and I said that I would invest in it and be part of it. And what really struck me, certainly in terms of there's a for-profit opportunity there, but is just the human social criminal justice impact piece. Much like I had said a while ago about, you know, thinking that I was an informed, educated, and, you know, well-read person around the global water crisis, I knew nothing really about the broken criminal justice system other than the headlines and the stories I read in various publications. Um, but at the level of how it changes not just the lives, certainly the victim and its family, but the perpetrator, but the people who actually didn't do it, but are on death row or sentenced to life. And, um, uh, this really just hooked into me and grabbed me. And so I've, you know, put some time in advising him and helping him with that. And, uh, it's, it's super interesting and it's opened me up to all kinds of experiences. In terms of what does it mean to kind of contribute to just a little bit sort of creating more positivity and truth in the justice system.

So Rob, given all these experiences, and there's a lot, I mean, actually I'm gonna ask you a question and if you feel you've already answered it, that's really fine. But I'm just going to sort of say, what's a lesson that's been the most painful to learn, but that has taught you the most?

Well, I mean, I just, you know, I have said it, which is the lesson of having all your money stolen. Like for me, it was the most excruciatingly painful lesson and the one I've learned from most. Um, and, and, and the one sort of, sort of, um, Surfing at the top of that is something that, you know, when I've been a Techstars mentor and others in situations where, you know, that young entrepreneur says, like, can you distill the— what's the one thing kind of question? Yeah, there's always a silly question, I find, because it's never one thing. But is, um, from a human perspective, because these are humans building companies, these are not robots, um, get really comfortable with discomfort. Like, get really, really comfortable with discomfort because you are guaranteed more than anything else to go through it. And if you meet that discomfort and back away from it time and time again, being an entrepreneur is not for you because this is built into the DNA, speaking of DNA, of entrepreneurship.

Totally agree. Completely agree. I love that. And last question is, what do you wish you had known earlier on your journey?

Yeah, I think that I wish I had known that saying yes to yourself and going down multiple paths at one time, while exciting and fun and engaging and compelling, not such a good thing. Not such a good thing. I mean, it is sort of predicated on being young and youthful and energetic, but it's not going to necessarily get you to your goal. And I'm not advocating necessarily because I don't necessarily do this, but for just only doing one thing. But if you can, and that's all you care about, just do the one thing. But even the other things that you might do, see if you can't actually have them feed the one thing.

I love it. The one thing. Rob, thank you so much for your wisdom, for your real talk today. It is very valuable to hear this coming from you. And I just want you to know a lot of people will benefit from this discussion. So thank you, Rob, and it was great to talk to you.

Yay. It was so fun talking to you. Thank you, Alisa Cohn. You're amazing.

Thanks for listening to From Startup to Grownup. If you like what you heard, give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alisacohn.com.