Jason Kirby. From High-Stress Startups to Fulfillment and Purpose
Episode - 38
Jason Kirby. From High-Stress Startups to Fulfillment and Purpose
Jason Kirby. He Sold Liquid Sky software to Walmart six years ago, but became disillusioned when Walmart abruptly scrapped the company's ambitious plans.
Seeking a new direction, Jason joined Generation Esports, rapidly scaled it and exited three years ago. This last exit prompted Jason to reassess his priorities, leading him to focus on family, health and meaningful work.
This shift inspired him to found Thunder, a tech enabled investment bank and launch the fundraising demystified podcast. In this interview, Jason shares his journey from high stress startups to a life centered on fulfillment and purpose.
What We Discussed:
00:00:14: Overview of Jason’s Expertise
00:00:27: Starting Liquid Sky
00:00:56: Formation and Operational Beginnings of Liquid Sky
00:01:24: The Vision and Mission of Liquid Sky
00:02:11: Partnership and Expansion Efforts
00:02:37: Business Philosophy and Personal Contribution
00:04:15: Diverse Industry Experience
00:05:50: Curious Nature and Learning Process
00:05:53: Liquid Sky’s Rapid Growth and Sale to Samsung
00:07:05: The Failed Acquisition by Samsung
00:09:17: Crisis and Pivot Strategy
00:10:01: Final Attempts for Acquisition and Survival
00:12:28: New Strategy with Walmart
00:14:39: Outcome and Life Post-Acquisition by Walmart
00:18:42: Excitement about Walmart Gaming
00:19:25: Transition to San Diego and New Opportunity
00:19:50: Introduction to Generation Esports
00:20:48: Investing Energy into Generation Esports
00:23:05: Initial Reflection and Momentum
00:24:42: Navigating the COVID-19 Challenges
00:25:28: Series A Funding and Rising Tensions
00:28:06: Decision to Leave Generation Esports
00:30:00: Self-discovery and New Relationships
00:34:19: Learning from Relationship Dynamics
00:35:00: Considering the Next Move
00:35:10: The Idea of Starting Thunder
00:35:42: The seed for Thunder
00:36:18: What Thunder does
00:38:02: Thunder as a tech-enabled investment bank
00:39:21: Introduction to the podcast "Fundraising Demystified"
00:41:00: Origin of "Fundraising Demystified"
00:43:04: The value of understanding venture capital
00:44:11: Advice for post-exit founders considering new ventures
00:51:01: Importance of risk tolerance
00:51:58: Determining the endgame for new businesses
00:52:41: Plans for Thunder
00:53:14: Decision against starting another big business
00:54:04: Balancing career and family priorities
00:54:48: Balancing Family and Ambitions
00:55:07: Introduction to Entrepreneurship in College
00:55:11: Influence of Successful Entrepreneurs
00:55:35: Reflections on Success and Family Time
00:55:39: Closing Remarks
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Anastasia Koroleva: [00:00:00 - 00:00:01]
Hi, Jason.
Jason Kirby: [00:00:01 - 00:00:02]
Hello.
Anastasia Koroleva: [00:00:02 - 00:00:06]
Hi. So good to have you here. Thank you so much for coming.
Jason Kirby: [00:00:06 - 00:00:10]
No, I'm excited. It's a beautiful day on the ride over here, so I'm a happy guy today.
Anastasia Koroleva: [00:00:10 - 00:00:25]
Fantastic. So let's jump right in. Let's do it. You are very experienced with exits your own, but also helping others. So I have lots of questions for you that I'm sure will be very interesting for my audience.
Jason Kirby: [00:00:25 - 00:00:27]
Happy to dive in.
Anastasia Koroleva: [00:00:27 - 00:00:29]
Can we start with liquid sky?
Jason Kirby: [00:00:29 - 00:00:30]
Yeah.
Anastasia Koroleva: [00:00:30 - 00:00:40]
And my first question is, how did you decide to start it and what your motivation was to start it in the first place?
Jason Kirby: [00:00:40 - 00:02:48]
So the story of Liquid sky really stems from me selling my businesses in San Diego and moving to New York and knowing that I had a vision in mind, but nothing really, like, set in stone. And upon arriving in New York, I was connected to an individual named Scott Johnston, who introduced me to this guy named Ian, who ended up being co founder and Liquid sky. And I was kind of run through quite a process of both me vetting. Ian is a partner, and the concept and the idea of what liquid sky could be. At the time, Ian was tinkering with this technology to enable what we call now cloud gaming, what we ultimately coined as interactive content delivery network. And I was just super passionate about what we could turn this into in terms of global access for people across the world that wanted access to a high compute performance machine that didn't have the means to shell out thousands of dollars or people that could forward that money but wanted the flexibility to pick up where they left off. I thought that was a noble mission and something that I was really excited about and kind of got to craft that narrative. And so that's what kind of got me to be like, this is where I want to plant my steak and dive all in. And ultimately, it was Ian and I working out of his parents house in Tarrytown for quite some time, kind of tinkering, getting this up and running, really working out what's going to attract a global audience for this product and deploying data centers all over the world with our partners at IBM. And, yeah, it was. That's kind of where it all came from. Getting connected to the right person, you know, having a technology, but not really a business. And then kind of, I always, you know, hindsight 2020, kind of where I see myself today and kind of how I've kind of envisioned how I contribute to the entrepreneur ecosystem is I turn good ideas into great businesses.
Anastasia Koroleva: [00:02:49 - 00:02:49]
Yeah.
Jason Kirby: [00:02:49 - 00:03:02]
So it's like, one. I never was, like, the original idea guy, even anything and everything I created was someone kind of providing an idea. And then I'm like, okay, connect. That's how it's a business. And then building the business.
Anastasia Koroleva: [00:03:03 - 00:03:07]
You were on the business side. You were the one who, who turned ideas into businesses.
Jason Kirby: [00:03:07 - 00:03:08]
Exactly.
Anastasia Koroleva: [00:03:08 - 00:03:13]
So you wouldn't say you're necessarily creative person or that's your form of creativity.
Jason Kirby: [00:03:13 - 00:03:54]
That's my form of creativity, yeah. I get joy out of coming up with, okay, there's something here. And this is what I do with my current day to day is like, okay, people are saying this like, how do we make this into a product that is, or a company or a business model that can really achieve what we think it could achieve? And figuring out that equation is what kind of gets me excited. And that involves, like, deciding how much capital is needed to kind of get it to wherever it's going and so on. So that's where I kind of found my superpower, is like, okay, an idea is an idea. Anyone has those. But what's the spark of that idea that can turn it into a real business?
Anastasia Koroleva: [00:03:54 - 00:04:15]
That's a very versatile skill. I see people like that moving from different industries into different industries all the time and changing their focus very successfully, while people who are more of experts in a particular industry may have much harder time after exit going into something completely different.
Jason Kirby: [00:04:15 - 00:04:21]
Yeah. If you look at my background, I am so scattered across industries, products, sectors, business models.
Anastasia Koroleva: [00:04:21 - 00:04:30]
Are you comfortable with that? Because a couple of weeks ago, I interviewed somebody who said it was their biggest regret. They didn't just focus on one thing and stuck to it.
Jason Kirby: [00:04:31 - 00:05:50]
You know, I would. Most business advice I've seen is be the best at one thing. And I feel that resonates with a lot of people. And I struggle with that a lot because I am. I also. But I also know a lot of entrepreneurs that are the ones that are like, scatterbrain and jump all over the place. And albeit they might have some mental difficulty with something like that, they still find ways to succeed. Yeah. My thing is just being curious. I want to know how certain things work. Like, my wife makes fun of me for all the YouTube videos I watch of just like, how random things work from, like, DIY projects at my house during COVID to like, you know, different business models, different business leaders, how are they approaching different challenges? And I just have a very unique ability to kind of take like, 1020 percent of the data that's being shared and be able to comprehend 80% of the opportunity or the narrative or the business very, very quickly. And I just have a lot of fun with that. It's just, like, a fun thing for me to kind of experiment with and dive into different projects with that kind of sense of curiosity, that desire to want to learn and understand from an expert, someone that has chosen one path, one thing, and being able to extract those types of stories and information from them, that's brilliant.
Anastasia Koroleva: [00:05:50 - 00:06:00]
So if we go back to liquid sky. So I find it super impressive that you guys sold the company three years after you started it. How did that happen?
Jason Kirby: [00:06:01 - 00:08:15]
So we were basically managing a house of cards. At the end of the day. We were burning way too much money way too fast. We were go big or go home. And our largest investor at the time was Samsung next. And so Samsung's, like, us venture arm, and we just knew that they were going to buy us. It was just such perfect alignment. All our demos, everything we did with Samsung devices, and we were just so dead set on driving all the numbers, all the narrative, everything towards that outcome, all b, two, c. We were just focused on, like, get as many customers across the globe as possible, because Samsung's global presence, their devices are ubiquitous, you know, everywhere, and if we could just have them acquire us and be an app, like a default app on every, and they have their server infrastructure all. It was just, like, the perfect partner. And so we were like, I think probably about a year and a half in, Samsung had invested, and they were also kind of, like, starting the conversation about acquisition. So we were just like, let's just keep this narrative going. They'll acquire us by the end of the year. This is 2017, and let's just go as fast as possible. Unfortunately, we got that acquisition offer. We're in diligence. Everything's looking great. Acquisition offer is phenomenal. It's just me, my partner, the board, and two employees that know about this deal. And at the time, we're about 40 people, I think going from just Ian and I to 40 people in about 18 months, just, wow. Everything was just crazy fast and tons of fun. I was learning. I was way over my head in terms of what I was doing. But ultimately, Samsung comes into the offer. Everything looks great, everything on paper is phenomenal, investors are happy except one, and we ultimately start pursuing that relationship. So come November 2017, for those that might remember, Samsung had a bit of a regime change, and the CEO went to prison for corruption. And that was in the midst of us closing. We were projected to close before thanksgiving.
Anastasia Koroleva: [00:08:15 - 00:08:16]
Oh, wow.
Jason Kirby: [00:08:16 - 00:10:17]
And we were, like, all marching towards that. Well, shortly before the whole hiccup with the CEO, our board decided that we weren't getting enough from Samsung. They wanted to go back to the well. Ian and I were like, no, no, let's march forward with this acquisition. Everything's great. We're very much like, because we're just pumping everything into growth to have a strong narrative into the acquisition, and knowing that if there's any delays we weren't ready for that board still persisted and pushed the counter. Samsung balked, and they're like, what is this? And it delayed us a couple weeks, and nothing came of it except some slightly disgruntled parties. But then that whole regime shift happened. So CEO gets fired. All this big news were like, Samsung next is like, don't worry, the deal is still going through. They, like, reassure us. They were amazing. We love them over at Samsung next and the team there. And so we just like, all right, let's keep going. But ultimately, the new CEO got signature authority. I think it was, like, on December 8, the day of closing. So we. We have already, you know, told we were at. We work at the time. We'd already said, we're like, we're canceling our lease. We're moving into the Samsung office. They already set up the office for us. We had bottles of champagne ordered. We have everything on ice over at the new office. We have all this, like, food catering, you know, scheduled for the next morning. And it was, like, the morning of December 8 or first week of December of 2017. And we get a text at, like, two in the morning from Korea saying the deal is dead. The new CEO has signature authority officially as of 08:00 a.m. this morning, Korea time, and he has decided to kill every deal. Every deal over a million dollars within the entire global organization is now killed or on pause for them to do an investigation again. Samsung do whatever they want.
Anastasia Koroleva: [00:10:17 - 00:10:18]
Yeah.
Jason Kirby: [00:10:18 - 00:10:24]
Wow. We didn't even know what to do.
Anastasia Koroleva: [00:10:24 - 00:10:29]
Especially given that you built the business for that. For that. Oh, my God.
Jason Kirby: [00:10:29 - 00:12:04]
For that exact outcome. So it's just like, you know, just so stressful. So, like, we need, like, and the whole team, we tell them to be there at 09:00 a.m. our team never showed up at 09:00 a.m. they were always there, like, 1011, and then they worked till, like, seven or eight or whatever, and we tell them, like, show up at 09:00 a.m. sure. We have buses showing up at, I think, 1030 to pick them over, take them to office. We had to give out all the offers within that hour and a half. We had to announce it. So we had this whole, like, agenda through the day. And then, you know, Ian that morning, you know, we just kind of. We were like, what do we. What do we do? Like, we. Like, he just sat in his office, and he just couldn't talk. And keep in mind, only two other employees know what's actually going on, and they didn't know. They were, like, so excited to sell the news because everyone's getting these pretty good offers. Like, we saw all the offers were phenomenal, and I had to make something up. Cause, like, we can't tell them about the acquisition. Can't tell them that that just fell through. We can't, like, just all the restraints around what news? So I was just like, all right, everyone, I hope you're really excited for our Christmas party in three weeks. Whatever employees was like, can we have it in three weeks? She had no idea. I was just, like, had to, like, architect this, and everyone's so, like, disappointed and, like, upset with us because we can't. We couldn't tell them what was going on because we didn't know ourselves and we didn't want to mislead them or, you know, there's just so much of that kind of employee psyche that you have to manage. So that was incredibly stressful, and. But fortunately, Walmart had reached out about three weeks prior.
Anastasia Koroleva: [00:12:05 - 00:12:06]
They did themselves.
Jason Kirby: [00:12:06 - 00:14:43]
They reached out to us, and, you know, one of their team members had just inquired, just like, hey, we're thinking about doing something in gaming. We'd love to have a chat. And we ignored them because I had a conversation, but we delayed the meeting because we knew we were gonna get acquired and we didn't want to ruffle feathers. What's the first thing I do? Pick up the phone and call. So that was December 2017, and basically, we had to pivot the whole business. Cause, one, we had to raise, like, an atrocious round that just obliterated the team in terms of stock and everything like that because we were gonna run out of money by January. So it just eradicated a lot of what would have been an awesome outcome with Samsung. To survival. And we have to drive this to a very quick exit quickly as possible. So I turned on. I turned off my marketing hat to my sales hat and started selling enterprise customers and new technology that we kind of just repurposed our marketing to be more for enterprise and started selling, like, six figure, seven figure contracts to, like, Walmart, LG, KT, telecom, all these different things. And it was just one whole new skill. Never sold enterprise technology before and having to, like, learn that and figure that out and then eventually just maintaining that relationship with Walmart, eventually rolling out some, like, concepts for Walmart gaming at the same time doing it for Verizon. And ultimately, Walmart was like, all right, this is something we want to make a bet on. They came in with what I felt was a fair offer, but a very disappointing offer compared to what Samsung was putting into the table. And at the end of the day, we were just like, this is an exit of, and we are not sustainable. Especially because, like, Amazon was. Rumors were going on that they were working on something, Google is working on something, Microsoft's working on something. And we needed a big bankroll to survive. So we decided to push the narrative towards Walmart. Kind of tease this narrative that Verizon was at the table because we were publicly working on something with them. And that ultimately drove the acquisition a lot faster than it would have otherwise and probably is what got it punched over the line. Always have two parties. Always have two parties involved. And, yeah, Walmart ended up coming in and buying us and kind of being our savior. But, yeah, I was insanely stressful trying to figure all that out and cut our burn, lay off people, and, like, reprioritize the business and still keep everything afloat. Like, everything's okay, but everything's on fire. So, yeah, it was.
Anastasia Koroleva: [00:14:43 - 00:14:47]
How did it feel then being with Walmart? Because you stayed for two years, didn't you?
Jason Kirby: [00:14:48 - 00:17:21]
Sort of. So at Walmart, basically, the whole narrative for Walmart was they were trying to invest in, you know, Walmart gaming that was we were supposed to bring to the table. And I was in love with the concept. They gave us a monster budget to go do it. I was leading all these amazing conversations, learning all these new skills. It was fun. And also, there's no break because also, I didn't get all the proceeds right up front. You know, it kind of came out over the two years with them. And so I was just so hungry after the acquisition to make this as successful as possible, like, put my name on this and, like, say that we did this. So for six months after the acquisition, we are just scaling, building, negotiating, flying all over the country. And it was just absolute. It was super exciting, but just, again, like, chaos. And also me navigating a big corporate life, which was unique, I think Walmart's credit at the time, they matched our pace and they gave us resources. They were really trying to pull back restraints and not add more, which I respect the team a lot there. What we didn't realize was a lot of that talent that was involved in that was a part of the jet acquisition. And their tenure, like, their earnouts were up in a couple months. And so they were trying to push all this forward. They were trying to make all this happen, but they all started dropping like flies because they're ten years old. And so we're now dealing more with Bentonville than we are kind of east Coast, West coast people, and there's just different culture. Everyone I met were amazing people. I have nothing bad to say about Walmart, but it was just very disheartening when we started seeing them drop off, and they were our leaders in this stuff. And when that started happening, there's a big decision from Walmart to basically stop all this future cool stuff that we're doing, divest from all that, and reinvest in the next day delivery and same day delivery to compete with Amazon, which, smart decision for them sucked for us because that was our budget. And about six months after the acquisition, about five days before, about a week before our big announcement at the big gaming conference called e three in LA, we had spent $5 million on this launch party. That was just the deposit. That was just the deposit. It was gonna be like 12 million probably all in. And that's, like, more than we raise as a company. And we're doing it for a three day lunch party. It was gonna be cool. It was actually pretty cool. I was. I was. I wish we could have brought that to life. That been really awesome. But right before we went live and told the whole world about Walmart gaming and releasing it to, you know, hundreds of thousands of customers, right off the get go, they just pulled the plug, shut it down.
Anastasia Koroleva: [00:17:21 - 00:17:24]
They just said, like Samsung did before.
Jason Kirby: [00:17:24 - 00:18:39]
Exactly. You know, the rug pulls in my career have been painful. So, yeah, they basically just decided that this budget has been removed and that it's just stopped. And again, like, to them, it's a drop of the bucket. $12 million isn't even. No one cares about $12 million at Walmart when they're managing 500 billion in revenue or whatever it was. So to them, it doesn't matter, but to us, it was everything. And so that was really disheartening. And they physically, actually put us on what I consider the roof. If anyone's familiar, the tv show Silicon Valley, where you go to the big company that you put on the roof and you're no longer useful. There was, like, a co working space above the Walmart office in New Jersey, and they literally put us in that office, and they're like, all right, well, you're no longer, like, the cool, sexy thing that we were trying to keep top secret in the company, and we need the space that you guys are in, so we're just gonna. We're just gonna move you up there. And they kept me on payroll and gave me option to do something else in the organization. All management was super nice and trying to, like, they all felt bad. Cause they all wanted us to happen. But, yeah, I was just, like. I was just in shock. I was angry. I was mad. I was confused. There was a lot of just intense emotions. Cause again, just abrupt.
Anastasia Koroleva: [00:18:39 - 00:18:40]
No, of course.
Jason Kirby: [00:18:40 - 00:18:40]
It was just like.
Anastasia Koroleva: [00:18:40 - 00:18:42]
And the second time in a row.
Jason Kirby: [00:18:42 - 00:18:43]
Yeah. You know, a year and a half later.
Anastasia Koroleva: [00:18:43 - 00:18:46]
It was a short period of time. It's just a few years.
Jason Kirby: [00:18:46 - 00:18:53]
And we were just so excited about the. I got so bought into the mission, and I drove the whole team around. This mission, got everyone super excited that we will be Walmart gaming.
Anastasia Koroleva: [00:18:53 - 00:18:54]
Yeah.
Jason Kirby: [00:18:54 - 00:19:47]
And ultimately Walmart entertainment with video and all those other cool ideas that we were working on. And, yeah, that. That was, like, a huge, crushing blow. And I didn't know what I was, like, not vindictive in any way, but I was just, like. I was angry. I wanted, like, just to do something else right away and distract myself. So that trip we were supposed to do, the launch party, this is, like, literally, like, a week later after the news, I go to San Diego instead, where most of my friends are. I grew up in San Diego, southern California, and just my friends kind of knew the whole story already, and they already had something waiting for me when I showed up. And they're just like, there's this company we invested in. Like, you should check it out. I was like, sure, yeah, whatever. Anything to get my mind off Walmart. Literally, I didn't know I was gonna spend the next two years working on that.
Anastasia Koroleva: [00:19:48 - 00:19:50]
And that was generation esports.
Jason Kirby: [00:19:50 - 00:20:36]
That was generation esports. Yeah. At the time, which was called high school esports league. Not my company, not my idea. The company existed for years before I got there, but as a small business being led by, you know, very passionate founders, three of them that really cared about bringing esports into the schools across America. I love that narrative, love that mission. And I was kind of adjacent in that space. I knew esports, knew the gaming world, knew the publishers from my time at Liquid sky and Walmart. And so I was like, a Yde perfect fit. And so, yeah, I just immediately just said, I know how to solve all their problems. I'm gonna jump all in and just did it as, like, consultant, but was working way too much, working way too hard, as if I was my company from, like, day one. Cause I just had all that energy.
Anastasia Koroleva: [00:20:36 - 00:20:38]
Yeah, you had all this momentum, right?
Jason Kirby: [00:20:39 - 00:21:51]
And I just needed to put that to something as quickly as possible. So they were put in front of me, like, moment of all that going on, and I was like, that's where I'm driving all my energy. That's what I'm gonna make, what I wanted to make at Walmart. And the founders were just like, cool. I don't think they knew what hit them when I. When I came on. There's a whole story in terms of that, but they were. They were doing about one hundred k a year when I showed up. And I was just like, this. This is way bigger. Every kid in America needs to have this as an option as opposed to traditional sports or to complement traditional sports, having esports as an outlet. So I just. I kind of took, again, like, the idea that they had that was like, a passion project and turned it into what eventually, by the time I left, was a $6 million annual run rate in 18 months or two years. Yeah, it was like 1820 months. So that's where I didn't even have time to reflect on the acquisition from Walmart and I. But the fun fact is and why I say Walmart had me for two years. I was still on payroll, and they didn't care that I was doing anything else. They just wanted me not to say, disparage them or say anything bad about them. And they're just like, you do whatever you want.
Anastasia Koroleva: [00:21:52 - 00:21:53]
Just interesting.
Jason Kirby: [00:21:53 - 00:23:04]
Just. Just, you know, don't give us. Yeah, like, don't. Don't give our m and a team a bad name. To which I don't like, I think they were phenomenal. I think they were a great partner. Just, they made a business decision that affected me negatively. Yeah. But, yeah, they kind of kept me on payroll. I got my earn out, got all that stuff without putting, I think I opened my Walmart laptop, like, once a month to check in something, just to make sure that I had, like, something I had to physically, like reports or something I had to submit for my team. And that was it. And that was my only contribution from Walmart during that entire time. And so that was awesome. And that also allowed generation esports to afford me. Cause I didn't care about the money and worked for basically pennies, in retrospect, to scale their company. Cause I had all that energy just like, this has to be applied to something that I care about as quickly as possible. So, yeah. Didn't even really reflect on the acquisition outside of probably one night with Ian when the deal was done, done, money was transferred. I think that was probably the most important moment. But, yeah, other than that, it was just full steam ahead on the next project once they pulled the plug for me.
Anastasia Koroleva: [00:23:05 - 00:23:18]
But you mentioned to me before in a separate conversation that your existential crisis only happened after generation esports because it got delayed by this momentum when you wanted to continue being busy.
Jason Kirby: [00:23:18 - 00:23:43]
Yeah. So I kind of dabbled for about a week or two before I went, all because generation esports was brought to me as a concept. I didn't meet with the team for probably a couple weeks, so I was thinking, like, do I do consulting? Do I. Do I try to find something Walmart? Do I try to start something new? I was like, or do I go do an NBA or something? Everyone slapped me in the face and said, don't do an NBA. You have an NBA.
Anastasia Koroleva: [00:23:44 - 00:23:45]
You have an NBA.
Jason Kirby: [00:23:46 - 00:29:16]
So glad I listened to them. Cause not my cup of tea. Yeah. So I jumped straight into generation esports, and I just. I was blinders on. Nothing else mattered. My wife was like, where'd you go? You know? Cause also, it was middle of COVID too. It's like Covid happened shortly after me joining. Well, it was about six months later, eight months later. So I was, like, fully vested into generation esports at the time. And then Covid happened, and we sell to schools, and, like, schools were shut down, and we had. It was just all the challenges we dealt with in that moment were so intense. I was losing my hair like crazy, you know, just like, the stress was like nothing else. But I just. I had to drive this to, like, a successful outcome. That's, like, all that was on my mind. And, you know, the founders and I would butt heads often because I was driving so fast, and they weren't used to it, and I had to keep, you know, try to keep catching them up. So there's definitely. That was building in the early days, but ultimately, you know, the market's hot. We're growing like crazy. We're signing massive deals with sponsors and partners and signing schools. Like, everything's up into the right. It's great. We screw the team from, like, eight people living on ramen to, like, a 65 person team with market salaries with a nice, you know, big office and everything, and impressive. Yeah, it was great. I was. I was loving it. But it was also, like, the hot market, too. It was 2021 going into 2021. So it was all good. And we navigated the pandemic perfectly to come out on top. But ultimately, what was interesting was we raised a series a from altos, successful VC firm. Really liked them. They wrote $11 million check into our Series A, and the founders just changed overnight. Our attitudes, like, just our relationship just started to shift dramatically. And I, like, I didn't probably attend to them as much as I should have. That was one of my regrets. I should have been more conscious of the relationship I had with them, but I was just so dead set on this mission of driving absolute success that I kind of forgot that at the end of the day, it's their baby and they can do whatever they want with it. And that, you know, it's like, kind of the power of being the founder. Yeah. And albeit I was driving all the success, I was kind of taking away all their decision making and just doing it myself and more or less running by the decisions by them and created a lot of tension and also wasn't there. I was in New York, I was flying back and forth and just created a lot of tension in the relationship and that I wasn't prioritizing. People were giving me signs like, hey, you should. She'd probably do this. And I was like, no. We're like, look at the numbers. Crushing it, and I don't need to slow down. That was kind of my attitude. And ultimately, a decision came about to do a deal with a partner that I wholeheartedly just hard know. Like, this is a horrible deal. This could cripple the company. And it's, in my opinion, was very dishonest from the partner because they were saying yes to the CEO on what the CEO wanted, the founder. But what was actually in writing was very different. Like, it was very much a bait and switch. And I try to warn them and educate them, but they were so passionate about this partner and working with this partner that they basically said, we're gonna do it. And I just exploded. And that's when it ended. I was just like, I can't. I can't do this. Like, my stress levels was just so high. My wife and I went on vacation. My wife's pregnant, and she's just like, I was on my phone the whole time we're in Mexico City, like, trying to have fun, and, like, I did not have any fun. Just so stressed about this. And ultimately came back and, you know, the relationship, we ended the relationship, and I decided that I want to sell my stock because I don't believe in this company anymore with the direction that they're going. And it was very, very tenuous and stressful, and it was very unfortunate because the business had so much potential. So, you know, long story short, business still exists. They went on to raise some additional capital, albeit I see it as a very different outcome than what would have been had I been there. But I think that doesn't matter. But it was at that moment where I'm like, it was just an abrupt stop. Like, this is overdose. I'm no longer doing this thing. I don't have anything else in the hopper to work on next. And I'm just like, what do I do now? Cause I was so angry and mad that this happened, and it was no longer my baby. And, like, again, like, I wasn't the founder, but I felt like it was like. I felt I really owned it. Like that mindset, and I tried to give it everything I had. It was just kind of taken away. So ultimately, I tried to figure out, what do I do next? So from that point on, this is, I think, May 2021. Just started meeting with friends. That was the number one thing I wanted to do. I just want to rekindle relationship because I went off grid. I stopped hanging out with people as much as I used to, stop connecting with people as much as I used to, because it was so immersed in the business and just kind of took a month or two of nothing. I did some real estate. You know, I was like, okay, I can do real estate.
Anastasia Koroleva: [00:29:16 - 00:29:25]
So you still had some of that momentum left. You feel if you felt you needed to go into real estate or that was driven by something else?
Jason Kirby: [00:29:25 - 00:30:00]
Well, I was already buying a property. Okay. I was closing the week after everything went to Chin. Yeah. So I was already in that deal. So I kind of just distracted myself with that deal and immersed myself and everything in real estate. But outside of that, I was, you know, that's not a full time thing for me. And so I was just meeting with as many people as I could to kind of have a self discovery. Like, what do I. Who am I? What do I do? What am I good at? Do I want to do something again? What do I want to do? Do I want to just invest? Do I want to.
Anastasia Koroleva: [00:30:00 - 00:30:02]
What did you find helpful?
Jason Kirby: [00:30:02 - 00:32:28]
Talking to people, you know, just having as many lunch chats, coffee chats as I possibly could back then. They were not. I wasn't, like, out every day on those things. It was, like, probably one or two a week. Lots of conversations with my wife, trying to figure out just what I do. And my wife's, like, obviously doing her own thing at work, and just kind of, like, she's very supportive, and she was like, you know, get back up on your feet. Come on. Let's go. Let's go. She didn't let me stay down for too long. I went back to the idea of doing an MBA because it was, like, something I could just do. You know, I could, like, I do an MBA and I can figure it out later kind of thing. So I started looking at that again, and. But someone kind of challenged me to, like, you know, look back at your old contacts, people you thought were interesting that you maybe never developed a relationship with deeper. And one of those people were the partners at Interplay ventures, like adventure fund. And so I kind of just hit them up out of the. I haven't talked them in years. I just, like, hit them up out of the blue and say, hey, I'm doing this thing now, or I had done this thing, you know, looking to do what's next, like, have a chat. And that ultimately started sparking a lot of conversation. They kind of gave me, like, a, like, oh, you're. You're like, a badass. Like, you can. You can get shit done. Like, what are you doing sitting on your hands? Like, let's. Let's find something for you to. To apply your knowledge to. So that was helpful because one is some valid external validation after going through what was pretty distraught, of course. Cause also I got connected to generation esports from my San Diego friends, and that kind of. That whole relationships kind of got a little upended a little bit or a little sensitive because of what happened with generation esports. So I felt like I couldn't truly tap that network as much. A lot of people weren't impacted, but some of the key people were. So that was, like, a stressful thing. So I was like, all right, let me focus on building new relationships and exploring new conversations of things that are outside my comfort zone and kind of seeing what comes of it. Did a lot of interviews, interviewed for various different jobs. Nothing that really, like, screamed out. Like, this is what I have to do. And I still didn't know what I wanted, so I wasn't even, like, crushing those interviews anyways because I was just like, yeah, I don't know. Yeah. So I felt it was like an ingenuine interview process. I was just. I was very quickly just dabbling into things and just not sitting idle.
Anastasia Koroleva: [00:32:31 - 00:32:38]
What was the most painful thing for you? Not being busy, being bored, confused.
Jason Kirby: [00:32:38 - 00:32:39]
Angry.
Anastasia Koroleva: [00:32:39 - 00:32:40]
Angry.
Jason Kirby: [00:32:40 - 00:33:15]
Yeah, I was angry. I understood it. I know why, but I didn't like the reason why. And I. It took me a while to accept what was my fault in that arrangement, and just also the, like, kind of looking back at my past relationships of your co founders and partners and stuff like that, what worked, what didn't work. I realized that, like, sometimes I beat to my own drum, and I don't always allow for my partners to get on the same rhythm.
Anastasia Koroleva: [00:33:15 - 00:33:16]
Mm hmm.
Jason Kirby: [00:33:16 - 00:34:46]
Because I move just. I make decisions too quickly and just going, going, going. And they might be going fast, as well, but they're going on a different rhythm. And so that was something I had to, like, reflect on and take some time, because a lot of friends were kind of telling me that, you know, like, hey, Jason, like, have you thought of this, like, blow mom? No. Like, I was right. But, you know, again, like, with time and a couple months of just kind of, like, analyzing, reflecting, and kind of having an emotional experience, you know, kind of reflecting, like, okay, I wasn't perfect. I was not right in every single situation, albeit the business numbers were great. Everything was up into the right. I could have managed those relationships better and still got the same, if not a better, outcome. And I think that's where a lot of my head and time and space went of just figuring out that those relationship dynamics and why. I was, like. It wasn't just naturally that I was, like, trying to figure out, like, what do I do next? And kind of having that. That diagram of, like, what do I like, what I not like, and what am I good at, you know, kind of thing, and just going back through that process, because it's still like, I'm, you know, I'm young. Um, what am I actually? I don't know what I am. 36. Um, you know, I still have so much ahead of me and so much opportunity. Like, I'm not gonna be sitting idle. And that. That was something I kind of committed to pretty early.
Anastasia Koroleva: [00:34:46 - 00:34:46]
Yeah.
Jason Kirby: [00:34:46 - 00:35:00]
So it was really about figuring out, like, okay, whatever I do next, I want to be able to do for a very, very long time and enjoy. And that's kind of where my head and my time and my thought process went.
Anastasia Koroleva: [00:35:00 - 00:35:08]
So your decision to start thunder, were you still angry at the time, or. There was a different reasoning.
Jason Kirby: [00:35:08 - 00:36:18]
I I had a different perspective. So this is. So I met with the partners at Interplay, and they were the ones that ultimately planted the seed that got me, like, okay, maybe I do my own thing. And, you know, I like the idea of working with them because they were partners or co founders, but they're, they're not in with me every day. So I have, like, autonomy control, but I don't have to, like, you know, cater to their personalities and needs. Like, it's a business relationship. But we're good friends. We have a lot of mutual respect, but I don't have to be worried about their execution abilities or any of that kind of stuff. So when they kind of planted that seed in my head, it was still pretty early, and I was not ready for it. And also the original seed for thunder was, like, not that enticing and, but I like the idea of having, like, investors and partners and, like, accountability buddies effectively because I felt like I didn't want to do something 100% alone again because I did that in my previous businesses. When I was younger, I was all alone on everything, and it just wasn't fulfilling as much. It was good lifestyle. I could do whatever I want, but I felt I had a much lower ceiling when I do stuff by myself.
Anastasia Koroleva: [00:36:18 - 00:36:21]
Do you mind telling my audience what thunder does?
Jason Kirby: [00:36:21 - 00:39:13]
Yeah. Yeah, sure. So basically, Thunder came about. It was, you know, the idea was planted in my head around creating, like, a matching platform for investors and founders. I seen them, you know, use those types of platforms that kind of suck. And at the end of the day, investors are invest based on relationships. You know, you can give all the AI and all the data you want, but at the end of the day, especially venture, it's a yemenite finger in the wind. How do I feel? Do I, you know, I want to bet on this person. I want to bet on this person, especially, like, early stage stuff. But that was the original concept. But I started, you know, it took me about two to three months to kind of, like, sit on the idea. And all this other things I told you about was going through my head and all this kind of, like, existential crisis stuff that I was going through. That seed was, like, kind of getting nurtured a little bit in terms of, like, what ultimately turned into is, like, wait, I can have a business where I get to work with incredible, incredibly smart, passionate, driven people and be a support person to them, help them take off one of their most important and more difficult things to do, raise capital, access capital, you know, plan for capital events and things of that sort. M and a I get to leverage something that I have experience in that, you know, I felt I was really good at in the previous businesses, and I could technically do this forever. And I get a fresh batch of, you know, businesses and clients and things of that sort that, you know, keep me on my toes, force me to learn new industries. And I was like, all right, that sounds fun. I was like, I think I could do that. How do I get there? How do I prove myself? How do I validate this? You know, we'll see. But I have a little bit of a track record. But, you know, as far as doing this as a service was unique to me. And of course, this is, like, peak market. So at the end of the day, we decided that thunder would be a tech enabled investment bank. And we say tech enabled in a sense that we provide a bunch of free tools. Technology. We have our own AI. It's basically an algorithm that identifies probabilities of interest from investors to help founders kind of navigate who they should prioritize building relationships with. It's not a, oh, we scored high. They're going to invest. It's like, no, there's so many other variables that you can't take into consideration with data that need to be factored in. And so that's where the service comes in mind. So we use our own products to kind of help service our clients, and we give it away for free to anyone else to kind of help navigate how they should pursue relationships. But ultimately, our real value, what we really do, is help companies source, you know, debt equity or kind of advise for m and A and help them figure out what their real options really are, help them reset expectations, especially all the ones drunk on 2021. I'm like, oh, these guys raised $100 million. Yeah, it's over now. Let's get back to reality. So I've had a lot of fun doing that. I met some amazing founders, and that's what I really get to enjoy myself waking up every day and doing.
Anastasia Koroleva: [00:39:13 - 00:39:31]
You also have a fantastic podcast, fundraising demystified, which I highly recommend for everyone to listen to. I think it's very practical. It solves specific problems, and it trains people in a very practical to do what they need to do. How did that idea come to your mind?
Jason Kirby: [00:39:32 - 00:42:00]
So the original idea, again, peak 2021. My wife's pregnant. I wasn't ready to, like, go all in on, like, 80 hours, weeks or anything like that. Cause I wanted to be there for my wife, wanted to be there for my kid. So I was just, like, working on, like, a little bit of the product and kind of chipping away at things. Little did I know the market was gonna collapse underneath us. I was like, wow, I should probably ramped up the business a little bit faster, capitalize on those, those, that timing. But ultimately, business market went to absolute bottom. And so I started figuring out, like, okay, how do I maximize this time? Because doing deals right now are just not going to happen. And that was like the premise of the business. Like, we want to close deals and that's how we're going to be compensated to create a incentive alignment. And so I was like, all right, well, how else can I spend my time? So we optimize and really focus on product during that time and kind of creating this free tool for people and then ultimately really focusing on content. So we started with the newsletter, the fundraising demystified newsletter, everything's on Thunder VC, but we started with fundraising demystified newsletter, thousand subscribers. What? We kind of started with, like, my network and people and something that was like, okay, but really with the premise of, like, how do we stay in touch? How do we stay relevant? How do we stay top of mind? That was really the objective I was trying to solve, and that's how we figured that out was newsletter. But then I was like, okay, newsletter is one thing, but I need, like, you know, I want to have conversations with people like this kind of stuff. Like, there's just so much value in being able to sit down with amazing people and extract, you know, their very specific things. And as I was dealing with founders, it's like, there's so much misconception around what's in the, you know, TechCrunch and, you know, strictly vc. Like, these company raised this much money, this company raised this much money. And all these founders that are adjacent to that, they sit there and just paint an invisible, you know, this, like, unrealistic expectation of what's actually, what's happening. Like, reality is venture capital is not nearly as glamorous as people think it is. And so I decided, like, you know what? There's a ton of podcasts out there that interview the, the person that became a billionaire, the person that became, you know, like that, you know, ten years ago, they bust, you know, they were in the position of these founders that are listening to the podcast. And I was like, what would it be like to have a podcast where people are actually in the thick of it right now, closing rounds right now?
Anastasia Koroleva: [00:42:00 - 00:42:01]
Yeah.
Jason Kirby: [00:42:01 - 00:43:17]
Then what are those, you know, what's happening to them? Like, what's different? And I've had such a diverse group of founders from, like, it took us two years to raise a million dollars to then finally get to, like, raise a proper round. And then, you know, people are like, yeah, I just called a couple buddies and raised like, 20 million. It's just like the whole gamut, just to kind of really why? That's why I call it demystify, because it's just so not transparent and everyone's trying to boast what makes them look good. That's the name of the game. Like, you know, the truth. Like all of our Walmart raise and all kinds of stuff, it's all like, all the positive stuff. You know, when we put out to the world, yeah, we raised $12 million. It's like, what are the terms? And how did that actually impact the founder? And stuff like that. But being that the founders are still in the business and they're still operating, it's like, how did you run the business and a fundraising process at the same time? What are some practical ways to look at it? And all these different personalities, different businesses, different industries. So that's kind of, I was just very curious of, like, solving that narrative and like, providing that narrative to founders that are in the thick of it right now, trying to figure out what's practical advice. Not Brian Chesky, who, his failed pitch deck, all his failure notes and all that kind of stuff from 2009. It's cool and inspiring, but it's a different market, it's a different environment these days.
Anastasia Koroleva: [00:43:17 - 00:43:54]
So let me ask you something that's relevant to my audience. As you know, in our post exit founder community, lots of people are considering starting a new business. And then of course, the next question is, should I use my money or should I raise money? Because we feel, and I was there as well, we feel, okay, now we can actually afford not having to spend time raising money. We also can keep all the control. So there are so many reasons not to raise money. If you have your own after an exit, what would your advice be to a person like that?
Jason Kirby: [00:43:54 - 00:47:21]
It's a great question. So there's two perspectives. You know, one personal investment thesis, or your family office thesis, whatever it is, does it account for a high threshold of risk in terms of capital allocation? And looking at yourself personally and just being like, are you over allocated into one asset? And are you comfortable with that? I think that's something that some founders I meet, they accumulate tons of wealth and they park it in interest bearing account whatever. They get their 5%, they live off that and they're comfortable. We're other ones when I just pile it back into another high growth opportunity. So it's really. I think the first question is risk tolerance. Like, I'm working with a client right now that has that same problem. They have all their own money. They could put all their own money into it, but it's sizable. In this case, it's a very sizable mid eight figure deal, but they want to de risk it. So bringing in outside capital partners, I think, adds accountability and adds resources and attention and a different element to things that ultimately create enterprise value. Also make it more accessible for acquiring talent. When you get to say, these other people are involved, there's a whole talent acquisition strategy around fundraising or working with fundraising partners. But, you know, from a founder's perspective of, I can afford this, I'm comfortable with this, and I can do it all, versus, you know, do I go and bring other people along with me? It just depends on the personality. Like, do you want full control and are you comfortable with what comes with that? Versus do I want accountability buddies, do I want people to come with me? Do I want people to grow with me? It's actually chat happening right now in the pep group. Just like, do they do it all on their own? Do they bring co founders in? And I was kind of in the in between camp. I wanted investors, I wanted to be accountable to a board, but I didn't want someone sitting next to me that could disagree and, like, you know, go a different path and be split on something. So that was how I decided to do thunder. But with, you know, other founders I've seen ultimately comes down to risk tolerance, of putting their primary capital up at risk for the new business and how comfortable they are doing it. And in what structure do they do it in? That's the other thing of just, like, do you just keep loaning your company money? You know, and also, I guess, actually asking yourself, really, like, what do you want the outcome to be? Do you want a cash flowing business? Do you want a big exit business? If you want a big exit business, you want a venture scale business. I always push people towards bring on the partners that have a more diverse experience and exposure to that world as opposed to, you know, like, look at what's his face, the Wework founder, like Adam Newman. Like, bringing in a 16, a 16 z into his deal. Like, he had plenty of money, but he brings in the big names to give him the big splash. So it's just like everyone has kind of their own reasons. But I think asking yourself, really what you want the outcome to be. If you want a cash flowing business that creates a wonderful lifestyle for you, then do not bring in investors. That's a terrible idea. But if you want to go big, happy will join you on the journey.
Anastasia Koroleva: [00:47:21 - 00:48:35]
Yeah, because, you know, I've been collecting post exit stories now for 13 years. And it's my observation that the most exit wealth bye far is lost in situations when people are trying to build much bigger businesses, putting just their own money in and being overconfident, and then completely underestimating how their own motivations will change over time. And then you meet people, they don't like talking about it, but in a private conversation, they will admit that they're five, six years into this new business. They couldn't care less about it. They lost excitement about it. They keep putting money into it. They can't raise money for it because their heart isn't in it and the business is not doing well. And then they keep doing it because also, it's very hard to close a business like this for years. And then you see the biggest losses. Sometimes people lose the whole wealth they got from previous exit through that, which is why I was so excited to hear your perspective on that. Should people stop and think, maybe even though I have money and even though I want control, I should be a little bit more careful?
Jason Kirby: [00:48:36 - 00:49:41]
Yeah. I think it's something that people really have to sit down and ask themselves, like, even founders that either have money or don't have money, I always start with that question, like, what's the end game? Because what partners you bring on with you, whether they're co founders, equity partners, debt partners, everyone, you kind of want to be aligned on where this ship is going and kind of have your North Star. And for some people, it's, you know, I want a huge exit. Some people want to ipo. Some people like comfortable life, lifestyle, business, cash flow. And if you can't answer that question confidently towards your business, like, I think you should probably slow down on whatever you're doing and answer that question first, because that changes who you can attract, whether it's talent, investors, partners, clients, customers. Like, if you don't have that mindset already in place and that goal in place, it can end up like those situations where you just kind of keep funneling money into things because you don't really know where it's going or what the outcome is going to be and you don't know what life is like without it, and you just kind of keep doing it.
Anastasia Koroleva: [00:49:41 - 00:49:56]
Yeah, and it often happens. Exactly, because people don't stop and think for a while what it is they want, and then years later they're like, oh, I should have started a cash flow business, or I should have just traveled the world and ignored my money or turned into passive investing.
Jason Kirby: [00:49:57 - 00:50:16]
Yeah, it happens a lot. Yeah, that's why the first part is like, what do you need to survive? If you have the means, what do you need to be comfortable and making sure you don't touch that and keep that aside. But, yeah, I see some people just pile it right back into the next thing. All in.
Anastasia Koroleva: [00:50:16 - 00:50:40]
Yeah. And they're very excited for a while, and then they keep telling everyone everything's fine. And then in private conversations, they're like, I shouldn't have done it. The phrase I underestimated the psychological effects of an exit is the most common one I hear in these situations, because sometimes you just need to address yourself a bit before moving on.
Jason Kirby: [00:50:41 - 00:51:27]
Yeah, I definitely give myself as much time as I probably should have, but, you know, I'm. I just, for me, it's like I'm going. I'm still. I feel like I'm so. Yeah, I have so many years ahead. I just steamroll ahead. But I think for everyone, it's kind of like a. Having that self reflection, that time to acknowledge that things are gonna be different. Your baby's gone. I think for me, it was also different that my time at each business was shorter. So if I were at liquid sky for 15 years, I'd probably be feeling different, which I feel like that's kind of been the correlation between some of the founders that I've met with and had these conversations with. If it was their life's work for at least, I would say, like, eight to ten years, the existential crisis is much, much bigger than for those over a shorter period of time.
Anastasia Koroleva: [00:51:27 - 00:51:36]
So you said that your advice is to think what your plan is for your business when you started. So what's your plan for thunder?
Jason Kirby: [00:51:37 - 00:53:04]
So it's basically a lifestyle business. I love the idea that I get to work with founders and build something of value and help them solve these problems. I get to choose who I work with. I constantly turn down people, just like, either from the idea they're working on or the business or the opportunity, whatnot. I don't feel like I have to work with anyone, which is nice. I get to, like, pick and choose, albeit I probably could be signing a lot more business and, you know, growing the business to have more staff a lot faster. And I. Part of me wants that because I do thrive better and, like, a slightly bigger organization. But I also want to be selective with who I work with and have that choice. So for me, it's like, I think this could be a very comfortable and sizable business, especially as we kind of scale up our clientele with the capital raises that we're doing. But it really comes down to making sure I control how much I put in and who I get to work with is more important than getting as big as possible. Like, I love the idea of, like, maybe I'll steal business from JPMorgan and Morgan Stanley one day at investment banking, but those shower thoughts get into my head in terms of what we could do one day if we just continue to execute you. But it's less so much that being the goal is more so of, like, choosing good people to work with and staying nimble, staying educated, getting to learn, and staying curious.
Anastasia Koroleva: [00:53:04 - 00:53:10]
So why wouldn't you jump into another big business with a big IPo goal?
Jason Kirby: [00:53:14 - 00:54:28]
I see what it, I know what it takes, and I rather help the people that want to do that and be, like, a support role than be the person in those shoes again, mainly because I know the strain it puts on a relationship and family. I love my wife and my daughter very much and hope to have another daughter or another child at some point. And I've kind of rooted my priorities in family, part of the reason why I moved here. And that's kind of the underlying decision across the board. And I know what I went through to not get an ipo with generation Eastbourne, like, the stress, you know, what I put into that. It's like, that would not be sustainable with my daughter. And also, I love supporting my wife in her career. She's more the corporate junkie loves that stuff, and she's moved up the ladder exceedingly fast at her company. And I love, that's her passion, that's what she wants to do. So I want to make sure that it's not all about my career all the time, which it was in the first several years of our relationship. So it's kind of like her opportunity to kind of have her outlet. So I think that's also part of the decision.
Anastasia Koroleva: [00:54:29 - 00:54:47]
So it basically sounds like there are two factors. One is that you were kind of traumatized by the last six years of your life. Building this business is at enormous speed. Right. And the second one is just the moment in your life when you're having a young family and you want to focus on it and give your wife more attention and support.
Jason Kirby: [00:54:48 - 00:55:39]
Yeah. And I think, you know, maybe things change dramatically when my kids get older and, you know, I, they're more independent and I might want to go big again. But I think in this moment, young family, I see, like, again, immersing yourself with other founders and other people in the ecosystem is so important for me. I got an amazing introduction to entrepreneurship in college. Being immersed with all these very successful entrepreneurs, like billionaires, 100 millionaires, and they come and talk to us and they talk about all their success. This is probably still one of the most transformational meetings in my entire life. I was like 21, I think, or 22. Founder I'm looking up to. He's billionaires old. And, you know, one of my fellow friends asked, what's your biggest like? I would throw it all away to have more time with my family.
Anastasia Koroleva: [00:55:39 - 00:55:42]
Jason, thank you so much. This was great.
Jason Kirby: [00:55:42 - 00:55:45]
No, thank you. Very thought provoking questions.
Anastasia Koroleva: [00:55:45 - 00:55:47]
Good. I'm happy. Thank you so much.
Jason Kirby: [00:55:47 - 00:55:48]
Awesome. Thank you for having me.
