In short
Exit Paradox Podcast Episode Notes
Episode Title
Jason Kirby. From Exit to Ease: Letting Go of the Stress
Host
Anastasia Koroleva
Guest
Jason Kirby
Episode Overview In this episode, Jason Kirby shares his journey from a high-stress startup life to finding fulfillment after multiple business exits. Having sold Liquid Sky software to Walmart, Kirby faced disillusionment when Walmart halted ambitious projects. He then joined Generation Esports, where he rapidly scaled operations and exited again, prompting a reassessment of his priorities. This led to the founding of Thunder, a tech-enabled investment bank, and the podcast "Fundraising Demystified." The conversation delves into his experiences, lessons learned, and the importance of balancing work with family and personal fulfillment.
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Key Themes and Discussions
- The Journey of Liquid Sky
- Starting Liquid Sky: Kirby started Liquid Sky after relocating to New York and partnering with co-founder Ian. The mission was to provide cloud gaming access globally.
- Rapid Growth: The company scaled quickly but faced challenges during the acquisition process with Samsung.
- Failed Acquisition: Samsung's internal turmoil led to the abrupt failure of the acquisition, creating significant stress and uncertainty for the team.
- Transition to Walmart
- Acquisition by Walmart: Following the Samsung debacle, Walmart acquired Liquid Sky, with Kirby initially excited about the prospects.
- Disappointment: Walmart's shift in strategy led to the cancellation of significant gaming projects, affecting Kirby's vision for growth.
- Coping with Corporate Culture: Kirby navigated the complexities of corporate life at Walmart, which included unexpected changes and high-pressure situations.
- Shift to Generation Esports
- Joining Generation Esports: After leaving Walmart, Kirby joined Generation Esports, quickly scaling the company and leading it towards a successful exit.
- COVID-19 Challenges: The pandemic presented numerous hurdles, particularly as the business relied on school partnerships during school closures.
- Personal Reflections: Kirby experienced personal and professional stress, prompting introspection about his career trajectory and relationships.
- Founding Thunder
- The Idea for Thunder: The concept for Thunder evolved from Kirby's previous experiences, aiming to support founders in fundraising while leveraging technology.
- Value Proposition: Thunder provides tools and advisory services to help startups navigate the fundraising landscape effectively.
- Balancing Work and Family: Kirby emphasizes the importance of family and personal fulfillment, choosing a lifestyle business model over aggressive growth ambitions.
- Fundraising Demystified Podcast
- Creating the Podcast: Kirby launched the "Fundraising Demystified" podcast to share real, practical insights from founders navigating the fundraising process.
- Focus on Transparency: The podcast aims to demystify fundraising and provide relatable stories from current entrepreneurs, contrasting with glamorous success narratives often seen in media.
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Key Takeaways
- Prioritize Personal Fulfillment: After exiting businesses, it's essential to reassess personal values and goals to avoid burnout and disillusionment.
- Sustainable Growth vs. Scale: Founders should consider their risk tolerance and desired outcomes when deciding whether to self-fund or raise capital.
- The Importance of Relationships: Maintaining strong business relationships and being open to feedback can lead to better outcomes in entrepreneurship.
- Adaptability: Be prepared to pivot and adapt to changing circumstances, whether in business strategy or personal priorities.
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Closing Remarks Jason Kirby's journey highlights the complexities that come with entrepreneurial success and the importance of focusing on what truly matters in life. His insights serve as a valuable reminder for post-exit founders to remain grounded in their personal values and priorities while navigating new ventures.
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For more insights, join the Exit Paradox community or connect with Jason through the "Fundraising Demystified" podcast.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:00My thing is just being curious. I want to know how certain things work. Different business models, different business leaders, how are they approaching different challenges. And I just have a lot of fun with that. Jason Kirby sold Liquid Sky software to Walmart six years ago, but became disillusioned when Walmart abruptly scrapped the company's ambitious plans. Seeking 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, tech-enabled investment bank and launch the fundraising Demystified podcast.
0:46In this interview, Jason shares his journey from high-stress startups to a life centered on fulfillment and purpose.
0:58hi Jason hello hey uh so good to have you here thank you so much for coming no I'm excited it's a beautiful day on the ride over here so I'm a happy guy today fantastic so let's jump right in let's do it um 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 happy to dive in can we start with liquid sky yeah and my first question is um how did you decide to start it and what your motivation was to start it in the first place so the story of liquid sky you know really stems from me selling my businesses in san diego and moving to New York.
1:49And 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 Johnson who introduced me to this guy named Ian, who ended up being co-founder of Liquid Sky. And I was kind of run through quite a process of both me vetting Ian as 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 one of the flexibility to pick up where they left off.
2:55I 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 stake 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, you know, 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 what, where it all came from, you know, getting connected to the right person, you know, having a technology, but not really a business.
3:35and then kind of I always you know hindsight 2020 kind of where I see myself today and kind of I've kind of envisioned how I contribute to the entrepreneur ecosystem is I turn good ideas into great businesses yeah so it's like one I never was like the original idea guy yeah even anything and everything I created was someone kind of providing an idea and then I'm like okay connect that's okay that's how it's a business and then so you were on the business side you were the one who turned ideas into businesses. Exactly. So you wouldn't say you're necessarily a creative person or that's your form of creativity.
4:12That'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?
4:53That'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. Yeah, if you look at my background, I am so scattered across industries, products, sectors, business models. Are you comfortable with that? Because a couple of weeks ago I interviewed somebody who said it was their biggest regret that they didn't just focus on one thing and stuck to it. You know, most business advice I've seen is be the best at one thing.
5:36And I feel that resonates with a lot of people. And I struggle with that a lot because I'm, I also, but I also know a lot of entrepreneurs that are the ones that are like scatterbrained and jump all over the place. And I'll be it. They might have some mental difficulty with something like that. They still find ways to succeed. 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 with 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 10-20 percent of the data that's being shared and be able to comprehend 80 percent of the the narrative the opportunity or the narrative or the business very, very quickly.
6:28And 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, the 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. 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? 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 gonna buy us.
7:18It 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 b2c we're just focused on like get as many customers across as 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 the server infrastructure all it was just like the perfect partner and so we were like i think probably about a year two you know year and a half and 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 you know into your indiligence everything's looking great acquisition offers phenomenal it's just you know me and my partner the board and like two employees that know about this deal and at the time we're about 40 people i think um going from just ian and i to 40 people in about 18 months uh just while everything was just crazy fast and um tons of fun i was learning i was way way over my head in terms of like what I was doing.
8:44But ultimately Samsung comes in 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. Oh, wow. 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.
9:31Ian and I were like, no, no, let's march forward with this acquisition. Everything's great. Like we're, we're very much like two, cause we're just pumping everything into growth to have a strong narrative into the acquisition. Uh, and knowing that if there's any delays, we weren't ready for that. Board still persisted and pushed the, uh, the counter Samsung balked and they're like, what is this? And it delayed us a couple of weeks and nothing came of it except some slightly disgruntled, you know, parties. and but then that whole regime shift happened so ceo gets fired all this big news we're like samsung next is like don't worry the deal's still going through they'd like reassure us they're amazing we love them um we're at samsung next and the team there and so we just like all right let's keep going but uh ultimately the new ceo got signature authority i think it was like on December 8th, the day of closing.
10:27So we have already, you know, told, we work at the time. We had 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 8th or the first week of December 2017. And we get a text at like 2 in the morning from Korea saying the deal is dead. The new CEO has signature authority officially as of 8 a.m. this morning, Korea time.
11:01And 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. Yeah. And, you know, again, Samsung can do whatever they want. Yeah. Wow. Oh, wow. Must have been such a show for you. Oh, my God. We didn't even know what to do. like especially given that you built the business for that for that oh my god for that exact outcome so it was just like you know just so stressful so like we didn't like and the whole team we tell them to be there at 9 a.m our team never showed up at 9 a.m they were always there like 10 11 and then they worked till like 7 or 8 or whatever and we tell them like show up at 9 a.m sharp we have buses showing up at i think 10 30 to pick them over taking a new 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 we 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 like pretty good offers like we saw all the offers were phenomenal and you know i had to basically i had to make something up because like you know we can't tell them about the acquisition can't tell them that that just fell through we can't like it's just all the restraints around would do 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 just you had no idea i was just like i had to like architect this and everyone's so like disappointed and like upset with us because we couldn't tell them what was going on because we didn't know ourselves and we didn't want to mislead them.
12:51It was just so much of that kind of employee psyche that you have to manage. So that was incredibly stressful. But fortunately, Walmart had reached out about three weeks prior. They did themselves. They reached out to us and one of their team members had just inquired, just like, hey, we're thinking about doing something in gaming. We'd love to have the chat and we ignored him because i had a conversation but we delayed the meeting because we knew we're going to get acquired and we didn't want to like ruffle feathers um what's the first thing i do pick up the phone and call so that was december uh 2017 and basically we had to pivot the whole business because one we had to raise like a an atrocious round that just obliterated the the team in terms of stock and everything like that because we were going to run out of money by January.
13:49So 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 as quickly as possible. So 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 things. 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 and at the same time doing it for Verizon.
14:37and 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 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 bank roll to survive. um 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 uh than it would have otherwise and probably is what got a punch over the line always have two parties always have two parties involved um and yeah walmart ended up coming in and buying us and kind of being our our savior yeah um 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 uh so yeah i was how did it feel then being with walmart because you stayed for two years didn't you sort of so so at walmart basically the whole narrative for walmart was they were trying to invest in you know walmart gaming that was what we were supposed to bring to the table and I was in love with the concept.
16:01They 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. 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. Put my name on this and say that we did this. So for six months after the acquisition, and we are just scaling, building, negotiating, flying all over the country. And it was just absolute, it was super exciting, but just, you know, again, like chaos.
16:35And also me navigating a big corporate life, which was unique. I think to 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're trying to make all this happen but they all started dropping like flies because their tenure was up 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 um but it was just very disheartening when we started seeing them drop off and they were our you know leaders in the stuff and when that started happening there was 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 so for us because that was the budget and about six months after the acquisition about five days before about a week before uh our big announcement at the big gaming conference called e3 in la we had spent five million dollars on this launch party that was just the deposit that was just the deposit i wasn't like it was gonna be like 12 million probably all in and that's like more than we raised as a company and we're doing it for a three-day launch 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 would have 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 down they just said like samsung did before exactly um you know the rug pulls in my career have been painful um 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 in the bucket 12 million dollars doesn't even no one cares about 12 million dollars 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 yeah 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 when you're no longer useful uh there was like a co-working space above the walmart office in new jersey and they literally put us in that 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 but 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 you know option to do something else in the organization all management was super nice and trying to like they've all felt back as they all wanted this to happen um but yeah i was just like i was just in shock i was angry i was mad i I was confused.
19:34There was a lot of just intense emotions because, again, just abrupt. No, of course. It was just like. And the second time in a row. Yeah. You know, you're an avalator. Because it's a short period of time. It's just a few years. Yeah. And we were just so excited about the mission. 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. Yeah. And ultimately Walmart Entertainment with video and all those other cool ideas that we were working on. And, yeah, 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 um so that trip we were supposed to do the launch party so this is like literally like a week later after the news um I go to San Diego instead where I'm you know most of my friends are I grew up in San Diego in Southern California.
20:27And just my friends kind of knew the whole story already. And they already had something waiting for me when I showed up. And they were just like, there's this company we invested in. Like, you should check it out. And I was just like, sure, yeah, whatever. Like, just anything to get my mind off Walmart. Little I didn't know I was going to spend the next two years working on that. And that was Generation Esports. That was Generation Esports, yeah. At the time, which was called High School Esports League. Not my company, not my idea. Yeah, 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.
21:06I love that narrative, love that mission. And I was kind of adjacent in that space, a new esports, new the gaming world, new the publishers from my time at Liquid Sky and Walmart. And so it was like a perfect fit. And so, yeah, I just immediately just said, I know how to solve all their problems. I'm going to jump all in and just did it as like consultant but was working way too much working way too hard as if I it was my company from like day one because I just had all that energy yeah you had all this momentum right 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 yeah that's what I'm going to 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 and there's a whole story in terms of that but they're they're doing about 100k 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 um 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 six million dollar annual run rate in 18 months uh two years yeah i was like 18 20 months um so that's where i i didn't even have time to reflect on the acquisition from walmart and 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 just interesting just just you know don't give us a bad name yeah like don't don't give our M &A team a bad name um to which I don't like I think they were phenomenal I think they're a great partner just they made a business decision that affected me negatively yeah um but yeah they they kind of kept me on payroll I got my earn out got all that stuff without putting I think I open 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 like that was my only contribution for Walmart during that entire time and uh so it was awesome and that also allowed you know Generation Esports to afford me you know because I didn't care about the money um and you know worked for you know basically pennies in retrospect to scale their company because it was just I had all that energy you know just like this has to be applied to something that I care about as quickly as possible um so yeah I didn't even really reflect on the acquisition outside of probably one night with Ian uh when the the deal was done done money was transferred I think that was like 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.
24:03But 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. Yeah. So I kind of dabbled for about a week or two before I went off 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, do I try to find something at Walmart? Do I try to start something new? I was like, or do I go do an MBA or something? Everyone slapped me in the face and said, don't, don't do an MBA.
24:40Well, you have, you have, you have an MBA. So glad I listened to them because not my, not my cup of tea. But 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, like, cause also it's middle of COVID. too it's like covet happened shortly after me joining um i was about six months later eight months later so i was like fully vested into generation esports at the time and then covet 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 um 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 under the right it's great um we grew 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 it was great i was i was loving it uh but it was also like the hot market too is 2021 you know going into 2021 so it was all good and we navigated the pandemic perfectly to come out on top but uh ultimately what was interesting was we got the we raised a series a from altos um you know successful vc firm really liked them um they wrote a 11 million dollar check into our series a and the founders just changed overnight our attitudes uh 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 it's their baby and they can do whatever they want with it and that you know it's like kind of the power being the founder yeah um 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 i created a lot of tension and i 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 probably probably do this and I was like no we're like look at the numbers I'm crushing it um 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 no 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.
28:03It 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 going to 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 and 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. I was 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 cause I don't believe in this company anymore with the direction that they're going.
28:44and 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 over. 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? Because I was so angry and mad that this happened.
29:26And it was no longer my baby. And again, I wasn't the founder, but I felt like it was. I felt like I really owned it, that mindset. And I tried to give it everything I had. And it was just kind of taken away. And, um, so ultimately I try to figure out what, what do I do next? Um, so from that point on, this is like May, 2021. Yeah. Um, just started meeting with friends. You know, that was like the number one thing I wanted to do. I just want to rekindle relationship. Cause I, I went off grid. I'd stop hanging out with people as much as I used to stop connecting with people as much as I used to.
30:05Uh, cause it was so immersed in the business and just kind of took a month or two. of nothing like I did some real estate you know I was like okay I can do real estate so you still had some some of the momentum left you feel if you felt you needed to go into real estate but that was driven by something else well I was already buying a property okay the I was closing the week after everything went to shit yeah uh so I was already in that deal so I kind of just distracted myself with that deal and immerse myself in everything real estate. But, um, outside of that, I was, you know, that's not a full-time thing for me.
30:46Um, 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? Uh, do I want to do something again? What do I want to do? Do I want to just invest? Do I want to, what did you find helpful? Talking to people, you know, just having having as many lunch chats, coffee chats as I possibly could. Back then, I wasn't out every day on those things. It was probably one or two a week. Lots of conversations with my wife, trying to figure out just what I do. My wife's obviously doing her own thing at work. She's very supportive, but she was like, get back up on your feet.
31:26Come on, 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 something I could just do. you know I could like oh I could do an MBA and I could figure it out later kind of thing so I started looking at that again and um 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 uh people were uh the partners at Interplay Ventures like a venture fund and so I kind of just hit them up out of the blue I haven't I'm doing this thing now.
32:04Or I had done this thing, you know, looking to do what's next, like, can I have a chat? And that ultimately started sparking a lot of conversation. They kind of gave me, like, oh, you're like a badass. Like, you can get shit done. Like, what are you doing sitting on your hands? Like, let's find something for you to apply your knowledge to. So that was helpful because one is some external validation after going through what was pretty distraught. Of course. Because also, I got connected to Generation Esports from my San Diego friends. And that kind of, that whole relationships kind of got a little, you know, upended a little bit or a little sensitive because of what happened with Generation Esports.
32:43So it was like, I felt like I couldn't truly tap that network as much. Like a lot of people weren't impacted, but you know, 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.
33:17Yeah. So I felt it was like an ingenuine interview process. So I was just, I was very quickly just dabbling into things and just not sitting idle. what was the the most painful thing for you not being busy being bored confused angry angry yeah i was angry um just like i understood it like 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 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 because I move just I make decisions too quickly I'm 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's you know like hey Jason like have you thought of this you know like blow mom you're like 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.
34:51I was not right in every single situation. I'll be at the business numbers were great. Everything was up and to 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 diagram of like what do I like, what do 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 what am I actually I don't know what I'm 36 um you know I still have so much ahead of me and so much opportunity like I'm not going to be sitting idle and that that was something I kind of committed to pretty early 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 um and that's kind of where my head and my time and my thought process went so your decision to start thunder were you still angry at the time or there was a different reasoning i i had a different perspective so this is so i met with the partners at interplay and they're 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 and control, but I don't have to like, you know, cater to their personalities and needs.
36:32Like 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. um 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 my previous businesses when i was younger it 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 did stuff by myself do you mind telling my audience with thunder does yeah yeah sure so basically thunder came about it was you know the idea was planted in my head around um creating like a matching platform for investors and founders um i've seen them you know use those types of platforms that kind of suck and at the end of 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 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 um 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 um 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 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, uh, events and things of that sort.
38:27MNA, 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, that 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? We'll see. But I have a little bit of a track record. But as far as doing this as a service was unique to me. And of course, this is like peak market.
39:04So at the end of the day, we decided that Thunder would be a tech-enabled investment bank. and we say tech enabled in the sense that we provide a bunch of free tools technology we have our kind of 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 yeah 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 um but ultimately our real value what we really do is help companies source you know debt equity or kind of advise for m 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 you know 100 million dollars yeah it's over now like let's get back to reality So I've had a lot of fun doing that.
40:07I've met some amazing founders, and that's what I get to enjoy myself waking up every day and doing. 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 way to do what they need to do. How did that idea come to your mind? so the original idea again peak 2021 my wife's pregnant i wasn't ready to like go all in on like 80 hour weeks or anything like that because i wanted to be there for my wife i want 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 going to collapse underneath us i was like wow i should probably ramped up the business a little bit faster capitalize on those those uh the timing but ultimately the business market went to absolute bottom.
41:02And 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 an incentive alignment. And so I was like, all right, well, how else can I spend my time? So we optimized and really focused on product during that time and kind of creating this free tool for people. Uh, and then ultimately, uh, really focusing on content. So we started with the newsletter, uh, the fundraising demystified newsletter, everything's on thunder, you know, dot VC, but, uh, we started with a fundraising demystified newsletter, you know, thousand subscribers, what we're going to start it with like my networking people and something like that.
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41:43I was like, Oh, okay. Uh, 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, you know, objective I was trying to solve. and that's how we figured that out was newsletter um 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 tech crunch 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 10 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 yeah 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 explain why that's why I call it demystify because it's just so not transparent.
43:22And everyone's trying to boast what makes them look good. That's the name of the game. The truth of all of our Walmart raise and all that kind of stuff, it's all the positive stuff when we put it out to the world. Yeah, we raised$12 million. It's like, yeah, but what are the terms and how 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? like what's the practical ways to look at and all the different personalities different businesses different industries um 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 you know brian chesky who you know like his failed pitched at you know all his failure notes and all that kind of stuff from like 2009 it's just it's cool and inspiring but it's not it's a different market it's a different environment these days so let me Let me ask you something that's relevant to my audience.
44:20As 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't 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? That's a great question. So there's two perspectives. 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?
45:09and like looking at yourself personally and just being like you know 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 like you know interest bearing account you know whatever like they get their five percent they live off that and they're comfortable um where other ones want to just like pile back into another high growth opportunity so it's 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 their all their own money.
45:42They could put all their own money into it, but it's sizable. In this case, it's, you know, it's a very sizable, you know, mid eight figure deal. And, you know, 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, you know, 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 you know 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 a chat happening right now in the pep group of 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 um 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 and if you want a big exit business you want a venture scale business i always push people towards bring on the partners that are have a more diverse experience and exposure to that world as opposed to, you know, like look at, oh, it's a face that we work for at, or like Adam Newman, like bringing in A16Z into his deal.
47:57Like 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, do not bring in investors. Like that's a terrible idea. But if you want to go big, happy to join you on the journey. Yeah, because I've been collecting post-exit stories now for 13 years. And it's my observation that the most exit wealth by 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.
48:45And 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 use lose the whole wealth they got from previous exit through that which is why I was so excited to kind of 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 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 you know equity partners debt partners like 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 i want ipo some people like comfortable life um 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 uh clients customers like if you don't have that mindset already in place and that goal in place uh 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 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 yeah no it's a yeah that's why you know the first part is like what 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 yeah and keep that aside um but yeah i see some people just pile it right back into the next thing all in 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 yeah i definitely need to give myself as much time as i probably should have um but you know i'm i just for me it's like i'm going i'm still i feel like i'm so i have so many years ahead i just like this steamroll ahead but i think for everyone it's kind of like uh having that self-reflection that time to acknowledge that things are going to be different your baby's gone i think for me it was also different that the my time at each business was shorter so if i were at liquid sky for 15 years i'd probably be feeling different um which i feel like that's kind of been the the correlation between some of the founders that i've met with and had these conversations with it was 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 So you said that your advice is to think what your plan is for your business when you started.
52:33So what's your plan for Thunder? 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 or whatnot. I don't feel like I have to work with anyone, which is nice. I get to like pick and choose. I'll be at. 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.
53:14but 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 you know making sure I control how much I put in and who I get to work with yeah is more important than getting as big as possible like I love the idea like maybe I'll steal business from JP Morgan and Morgan Stanley one day in investment banking but uh you know those shower thoughts get into my head in terms of what we could do one day if we just continue to execute but it's less so much that being the goal is more so of like um choosing good people to work with and staying nimble staying educated getting to learn and staying curious so why wouldn't you jump into another big business with a big IPO goal?
54:13I 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. Um, mainly because I know the strain that 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 and 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 knock at an IPO with Generation Eastport. What I put into that, that would not be sustainable with my daughter.
54:59And also I love supporting my wife in her career. um she's you know more of the corporate junkie you know loves that stuff um and she's moved up the ladder you know exceedingly fast um 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 you know 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 yeah the decision 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 yeah and i think you know maybe things change dramatically when my kids get older and you know i yeah they're more independent and i might want to go big again but I think in this moment young family I see 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 it's probably still one of the most transformational meetings of my entire life I was like 21 I think or 22 founder I'm looking up to is you know billionaires old and you know one of my fellow friends asked like what's what's your biggest regret I was like I would throw it all the way to have more time with my family Jason thank you so much this was great no thank you very thought-provoking questions good I'm happy thank you so much awesome thank you for having me
From the publisher
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. _____________________________________________________ TIME STAMPS: 00:00:00: Overview of Jason’s Expertise 00:01:27: Starting Liquid Sky 00:01:56: Formation and Operational Beginnings of Liquid Sky 00:02:24: The Vision and Mission of Liquid Sky 00:03:11: Partnership and Expansion Efforts 00:03:37: Business Philosophy and Personal Contribution 00:05:15: Diverse Industry Experience 00:06:50: Curious Nature and Learning Process 00:06:53: Liquid Sky’s Rapid Growth and Sale to Samsung 00:08:05: The Failed Acquisition by Samsung 00:10:17: Crisis and Pivot Strategy 00:11:01: Final Attempts for Acquisition and Survival 00:13:28: New Strategy with Walmart 00:15:39: Outcome and Life Post-Acquisition by Walmart 00:19:42: Excitement about Walmart Gaming 00:20:25: Transition to San Diego and New Opportunity 00:20:50: Introduction to Generation Esports 00:21:48: Investing Energy into Generation Esports 00:24:05: Initial Reflection and Momentum 00:25:42: Navigating the COVID-19 Challenges 00:26:28: Series A Funding and Rising Tensions 00:29:06: Decision to Leave Generation Esports 00:31:00: Self-discovery and New Relationships 00:35:19: Learning from Relationship Dynamics 00:36:00: Considering the Next Move 00:36:10: The Idea of Starting Thunder 00:36:42: The seed for Thunder 00:37:18: What Thunder does 00:39:02: Thunder as a tech-enabled investment bank 00:40:21: Introduction to the podcast "Fundraising Demystified" 00:42:00: Origin of "Fundraising Demystified" 00:44:04: The value of understanding venture capital 00:45:11: Advice for post-exit founders considering new ventures 00:52:01: Importance of risk tolerance 00:52:58: Determining the endgame for new businesses 00:53:41: Plans for Thunder 00:54:14: Decision against starting another big business 00:55:04: Balancing career and family priorities 00:55:48: Balancing Family and Ambitions 00:56:07: Introduction to Entrepreneurship in College 00:56:11: Influence of Successful Entrepreneurs 00:56:35: Reflections on Success and Family Time 00:56:39: Closing Remarks




