Made It with Connor Tomkies

v2_Ep 2_Aaron White
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The market did not want what we were selling. Did the bigger players push back pretty hard? The bigger players suit us. That was a fun series. A announcement, Hey world, we've got a lot of money to build with. And also we're under, uh, we're under attack.

Hey, co founders welcome to my second million with Connor Tompkins, where we meet with bad ass entrepreneurs who've successfully exited their companies.

Today's guest, Aaron White, a successful entrepreneur who recently sold two companies, ProfitWell and Blissfully. And is now navigating life as a post exit founder. Hey everyone. I'm here with Aaron White. He recently sold two companies. So one is ProfitWell to Paddle and the other one Blissfully, roughly at the same time, and right now he's figuring out what life is as a post exit founder.

And I'm here to explore that with him. So how's it going Aaron? Great. Thanks for having me Conor. Really appreciate a chance to be here today. It's good to have you. I really want to jump into your, your background really quick. Your LinkedIn is a good read. Like, I feel like I could probably start from the bottom and work my way up.

And there's a lot of interesting tidbits throughout the way. Would you care sharing a little bit about your background and how you got to the point where you were selling two companies simultaneously and going through that process? Yeah. Yeah. I would be happy to share all that. And you know, if I could turn LinkedIn to the, the ultimate adventure story, uh, that would be fantastic.

A little more ups and downs are in between those events that I think it indicates. My parents had their own business. So when I was young, the dinner table was a conversation between them about what was going on at work. They were doing interior design, space planning. So I was living in that, you know, you run a business.

That's just what you do mindset from a young age. That said, I got really distracted by computers. They brought a PC home one day and that was the end of me. I just lived in my bedroom, playing PC games, dorking around in MS DOS, things like that. And that continued for a long, long while. So high school, college just got deeper and deeper into tech.

And my first job out of school, even in school was at startups. So I've, I've only really ever been in startups. And I think the. The largest company I've ever worked at, at this point, was one of the companies that I was CTO at, so that would be Fender. Prior to that, it was maybe a venture capital firm of 50 people.

It was the largest organization I had been a part of. So I've lived in this very tight bubble of building things and helping others who build things. And the path to kind of a spectacular 2022 for me was long, because both of those businesses got started in Years prior, we started profit. Well, originally it's price intelligently back in the 2010 timeframe.

And, you know, that's a, a 12 year overnight success story implicitly was started in 2016. So you've got another eight years, six, eight years before that kind of hit, you were talking about how it was a little bit of like a lifestyle. Shift. It was a massive shift. You were going from living with family members and then overnight you have these two exits and your circumstances pretty drastically changed.

And so how has that transition been over the past couple of years? There's survivorship bias. You know, it's not lost. I mean, we're having this conversation because things went well. But there's another universe where I'm the same 42 year old man, but in dead broke and really beating myself up when blissfully was at, uh, a very kind of critical juncture, my wife got very sick.

COVID happened and I just ended up trying to maintain the lifestyle and burnt my finances to the ground to keep the business alive and keep my, my wife as healthy as possible. And that resulted in me living under a conference room, a table on a mattress, mice jumping off me and, you know, showering where I could get it, et cetera, uh, eating a calzone every night to, you know, soothe my soul.

Moving in with her family for about a year. And then these two exits happened. So it could have gone another way entirely. But what I know is that I always gave it my all and really went all in on everything I was doing. And so that's equal parts amazing and enabled some of these outcomes and also can go really hard the other way.

But when the two sales came together, things changed pretty fast going from a house that was letting the cold, the new England cold in, in the winter and working out of a basement on a couch. To moving down to Florida, buying my first home. That's been great. It's, it's hard not to be thankful that so much weight has been lifted off my shoulders.

But in the end, I just kept running a tech startup and building team and building product and that's outside of family stuff That's the most engaging thing I could possibly be doing so that has not changed but a lot of anxiety is washed away And that's awesome. Yeah, no kidding It's going from being responsible probably for two companies and a lot of employees to probably completely different like day to day Oh yeah, I've got the cat.

I have to make sure that the cat is fed and I'm not even good at that. Hey, podcast listeners. We are currently looking for sponsors for this podcast. If you guys are looking to connect with other business owners that are scaling and growing their company, and you guys are interested in a spot on this podcast, uh, we're looking for you.

So reach out to. ConorTomKeys. com or OperatorEquity. com. And we're glad to help set you guys up with a spot on this podcast. All right, cheers. Back to the pod. I want to follow your career a little bit because you've worked in a lot of different places and you said that you were interested in computers at an early age.

So if you were to pull some snippets as to how you got to where you are now, um, would you mind taking us on that path really quick for those that don't know you? In high school, taught myself how to program and, you know, found a programming class. And I built them an entire business, uh, operating system application.

You know, you could record your clients, record your invoices, all these things. Maybe you'd call that an ERP. I tried desperately to get them to use this thing and they never would. So kind of set that aside. I ended up studying physics in college out of deep interest in how the universe works, but I found that all of all the roads that that took me were so much less interesting than making things.

Making something, showing to someone, getting a chance to wow them, just is such a gratifying feedback loop. Uh, and even showing something to someone that they hate it is also a pretty potent and addictive feedback loop. You know, just to jump ahead here a little bit, like if you've got a customer that hates you, that's wonderful.

Or a prospect, because hate is an emotion that says, I get what this could be and you're failing to deliver it. And that means you can close that gap. So. Showing people things and getting strong reactions is just really addictive. And so with, you know, with college, I switched from physics into computer science.

That was at Carnegie Mellon. It wasn't an easy thing to do because my grades were terrible. Transferred in, and that was just the, the, the true beginning of my career as a technologist. Cause I got deep into the theory and married it with my love of building things. And from there, it's been startups and side projects ever since the real transition from building products and tech into building businesses actually happened at the first startup I worked at post college we were making web services, debugging software.

So, you know, ancient internet wisdol that I'm glad are dead because they were terrible. Our first customer happened to later go on to be the CTO of Amazon, uh, Forerunner Vogel. So that was pretty awesome. But he was one of the very few customers we had. And I remember going to the sales side of our office.

It's like a team of 20 people and somehow engineering was in this barn and sales was in this barn in the woods of Hollis, New Hampshire. I went over there and I sat down with the sales guy and I said, are we selling anything? And he said, no. And that was, that was a huge punch in the face and a wake up call for me.

And that was the first time I vowed never to only focus on the tech side. Part of product ever again, because it's clearly not enough. The market didn't value what we were doing, or we weren't getting the message out, or we weren't navigating the sales process correctly. Something was wrong. I didn't know what it was.

I'm a bit of a control freak. And so that was the, you need to be involved in that stuff, Aaron, or you're going to be spinning your wheels, doing things that aren't working that you just can't see. And so the next, you know, everything after that, I was co founder, uh, status from, you know, day one, because I just needed that.

Control and that visibility. Otherwise. Who the hell knows? And I don't want to lead things up to fate. I like doing, and I want to succeed. There's a couple of traps I think companies fall into. And one is writing thousands of lines of code, even if it's the most beautiful code in the world and it not having a market or not having a customer to sell on to, and I think I've, I fell into that one for sure.

The other is. To be pitching like nonstop and the idea that success is, is raising money and going down that route and getting mentions in PR articles. And that wasn't quite it for us either. And so probably now your approach is very different from back then. As far as if you launch anything, it probably already has a market and you probably already have some customers in mind.

I, for sure. There's definitely a middle ground there. I think as a builder, it's easier for me to err on the side of making things than it is to promote what I'm doing. So I, I constantly have to pull myself into promotional mode. That said, when I was experimenting with new startup ideas, we would always just create the landing page first, that whole strategy.

Just see if there's any latent interest out there in what you're doing. Why not? It's so cheap, but you have to get out of your own way because the moment you lock onto an idea and you say, this thing is, is correct because it, it tickles my mind, you've fallen into a trap. You might be end of one, you have no idea, or the dynamics might be wrong, et cetera.

So trying to get interest and some notion of how distribution is going to work upfront is validating probably one of the bigger traps for first time entrepreneurs, which is making something. Glorious under the hood that to your point, no one in the world cares about. And then, you know, it doesn't, it doesn't matter what you've done.

You can make a crystal castle in the sky. And if no one can get there or cares about it, you've wasted time, effort, and a lot of smart people's talents. And that's unfortunate. What were some of the ones that you, you built after this? And, and what were the results? After my experience of finding out we weren't selling anything, I over pivoted.

I went to consumer and we tried to make a site where kids can make drawings and animations online. It was called Doink. Uh, pronounced by many people, unfortunately, is Doink. Not a great name. And that was really, that was still closer to the same problem. We got half a million kids using it, but where we failed was we failed at fundraising.

And I learned a lot, which I applied very successfully to my next venture. And we failed at hiring, um, key talent. And I'd say specifically around, Monetization, uh, just as a business, we just were, we were too shy about charging for what we had done. And that was unfortunate. So learned a lot about other parts of business construction.

Again, most of these lessons are the hard way. Proxlet was a side project with a friend where we got together and said, wouldn't it be great if Twitter could fricking mute things. And so we built this API proxy that you could point your Twitter browser experience through this proxy, and it would do all this munging of things, Ads, remove keywords, do translation.

It was really cool and ultimately it got shut down. I solved a lot of the, are people using it? Am I able to get feedback and iterate it to make them better? But they weren't necessarily. Sound businesses, you know, end to end. And that one taught me platform risk, like no other thing ever had. So very important lesson in there.

Be careful who you build on top of, because if you have that kind of dependency, you can be snuffed out overnight and there's not much you can do about it. So boundless was a really bold venture play. We're going to make textbooks obsolete for college students. You can learn anything online. Don't be buying those textbooks.

The market did not want what we were selling. Did the bigger players like push back pretty hard? Oh, the bigger players suit us. That was a fun series. A announcement, Hey world, we've got a lot of money to build with. And also we're under, uh, we're under attack. Oh, geez. Yeah. You know, the, the, the, you can look at the stats of how people The price of textbooks have outpaced inflation for years and years and years.

It's really gross and embarrassing. Uh, it's hard. I mean, if you're a student and you're just trying to afford going to school and you're just paying for an 11th edition that has like five changes from the 10th edition, it doesn't make sense. The problem was. There are two groups of students, those who take their education so seriously, they will not deviate from the assigned prescription of what they should be doing, in this case buying textbooks.

And those students probably have loans, which actually, weirdly, not weirdly, makes them less price sensitive. And then you got the other end of students, which just don't give a shit. And they would use sites like, you know, these kind of, uh, answer sharing sites and that's all they cared about. And we didn't want to become that.

I felt really queasy with the idea that, Hey, we could attract a large audience. We published answers to textbooks, but that's not a business to me. That didn't go the way we hoped. We did exit it. It was very close to, um, dollars in, and we actually had two suitors, one that had put a million bucks in my pocket, you know, before my, my thirties.

The other one that would return just money to. Our investors. And unfortunately it, it went that way, but it was so close at the time. And that lesson was no deals done until it's done. Like until everything's signed and cash is in the bank, you should be on your vigil because it's just not real. And that lesson was very helpful for the rest of my career.

Um, I've seen so many things go wrong. I feel like that's true for partnership deals, joint ventures, but especially when going to market, it's like no deal is more than 60 percent likely to go through and it's like. Having that mindset that even if this deal doesn't work out, I'm still running a profitable business.

I'm still scaling, whether this happens or not, like I'm not going to put all my eggs in that basket. Your equity always value at zero full stop. I will never play a game where, you know, unrealized private equity. There's no value in it. Don't kid yourself. It could blow up even no matter how successful you are, it could blow up overnight.

Don't count your chickens until they've hatched. Um, and that's, that's been. Grounding in the most real ways ever since then. The idea though, is like, I'm doing this, like, this is my path. If you want to join. Great. If not, that's also fine. I'm good. I'm good. Right. Yeah. And I, I like that approach also with running a company of fundraising too, because it's like, I'm going to be running this company.

It's going to be bootstrapped and profitable. It's going to look. Good. Right. And I could take your money or I, I'm okay, not. And as they can kind of tell, they're like, this guy is okay. And I kind of want to be involved in this. That was how we failed. I think at fundraising for the art company, we just sort of had this, we need your permission vibe to ourselves while fundraising.

And I don't think we believed it deep down, but that's how we presented when we fundraise for the textbook company. And then, you know, every company thereafter was here's the big vision. Here's the traction. You're welcome to get on this bus. You know, but we're not, we don't need your, your superlative permission or deep insight to validate what we're doing.

That's that's it's you've reversed the direction of power unhealthily. If that's your approach to it. Also having that scar tissue built up, you know, you have that deal experience, you're comfortable talking about the different terms, you know, what you want whenever you're going into it helps. The one thing I say to that audience as well is adulthood is an illusion only children can see.

Which is to say that if you think someone else knows more than you do, like, oh, you're going to go meet the guru who's going to drop the, you know, the, the universe truths on your head, that person doesn't exist. Everybody's making it up as they go along. Even the seasoned folks, you'll present, you know, the best entrepreneur in the world, maybe a billionaire, your idea, they'll give you feedback.

There's some chance there's good feedback, but there's a great chance it's really crappy feedback because they just don't understand your market or they don't understand the new tech. So it's just hard. You just got to keep taking shots on goal. Tell me about the two that, that worked out. Tell me about, uh, blissfully and tell me about profit.

Well, because those, those were longer journeys too. They weren't, they didn't happen overnight. What did you say? Or journeys with very meaningful, very meaningful exits. So I'll start with, with, with profit. Well, which was originally called price intelligently. And that was born of a Set of weekends that my high school friend, Christopher O'Donnell, who went on to become the chief product officer at HubSpot, and we would get together on the weekends when his wife was out of town and we would just bang out a product.

It didn't matter what it was, we would just bang something out and then on Monday we'd try to sell it. And we've repeated this a number of times after a few repetitions, we were saying, well, how the hell do you price software? Cost of goods is negligible. Like what, what do you do? Finger to the wind. And we found a couple of these different pricing techniques, Van Westen door price sensitivity analysis, discrete choice modeling, things like that.

And we came up with this survey tool that would help people survey their audience or their intended audience to figure out optimal pricing. We put it together. We sold it on a weekend. What we found was there was a ton of interest. But it was very, very hard for people to run this software on their own.

So it needed to be more like a consultancy, a services business, where we would conduct it on your behest. And we met up with Patrick Campbell, who was then at Gemvara doing pricing. He was at NASA doing a bunch of deep security analysis. He was so brilliant and we're like, dude, this thing is made for you.

This is clearly not something that we would nearly do as well as if you had this. And he took the business and he ran with it. And so Christopher and I became board members, tried to help. Uh, Patrick brought such incredible superpowers to this thing that honestly, I mean, I mean, he was CEO and he is the face of the whole thing and he deserves 99.

999 percent of the credit. Your pricing module is probably the other thing. It's very easy to change. If you price right, it flows straight down to your bottom line. Like that's a no brainer. So how did you take it to market? It's a no brainer in so many different ways because people might churn due to a bad pricing model.

They might fail to sign up during the pricing model. You might not capture success in tandem with them, which is sort of an ongoing misprice. And frankly, most people just underpriced, period, which means you're leaving a lot on the table and actually narrowing your ability to go to market effectively.

There's a lot of different ways pricing is central to success for an organization. And I think a lot of entrepreneurs get funny with the money early on and don't tinker with it and don't try to align it. You know, if you're a first time entrepreneur, it's just, you're sometimes you're just grateful that people are paying you honestly.

I was talking to Andrew Warner in the first podcast episode, and we were talking about permission to receive money. It's like, Hey, can we please like, thank you so much. Like you're, you're almost nervous to accept, um, payment and we normally price too low and there's a value associated with, um, price. So if you price higher, people are going to be more involved and more engaged and it gives you more leeway to provide a better service.

So I'm, I'm on board with that for sure. If you're making a great product, I don't want to say your customers are lucky to be working with you because you do have to cherish them. That's that that's probably over tilting, but it's not, Oh, please give me money. And my God, am I thankful you did like that?

That's people can smell that. And you know, it's not, it's not good for your psychology and it's not good for their perception either. Hey, podcast listeners, I made operator equity as a place for entrepreneurs to invest and buy and other entrepreneur led businesses. If you guys are interested in. Uh, learning more and possibly buying a business.

Or if you're interested in possibly selling your business to other entrepreneurs that have sold their business in the past, please reach out to operator equity. com. I'm really excited about this new project and I think that entrepreneurs should be buying more businesses. So if this resonates with you, check it out.

Bye. There's this trend around community building and like launching. It used to be there's only like EO and YPO and they've been around forever. Now there's communities for subsets of groups and some of them are paid and some of them are not paid. And we're a part of some of them that are free and some of them that are paid.

And I was wondering about what your thoughts were from a pricing perspective about value creation inside a community and how that should, how that's going to change probably in the next I don't know, a couple of years as things get more saturated. Here's my thesis. I think paid communities are great.

And I think they're only going to go up in terms of their value to not just their groups, but society at large. We're entering a phase now where AI can generate plausible human content at scale and dirt cheap. And it's going to saturate every medium, text, email, voice calls, your Reddit forums, somebody's already doing this stuff, you know, X, LinkedIn, you name it, wherever you see humans participate.

If there's not a cost to be in that community, AI is going to flood it and you can kind of smell it as spam now, but I think that's going to go away. Like these models are getting better and better. So I was joking, like, let's say there's that one, the Hamptons, right. Which I think, you know, you also, you know, are aware of.

Maybe, I don't know what that community charges or if it charges anything, but let's assume there's some community out there for well to do folks that charges, you know, 20, 000 a year, kind of like a, you know, a country club. Well, AI might still join that because if it can come in and befriend rich people over three months and say, Hey, I'm just like you and you have meaningful conversations with it.

And then on month three, it says, by the way, I sell private planes. Do you want to buy a jet? If enough people bite at that, it's economically viable to flood all the rich person communities Pay to join communities with AI. So I share all this because I think that paid communities are going to be a necessary gate to keep out the hordes of spam AI.

So whether on the merits or not, they mattered pre AI, I think they're actually fundamentally necessary post AI. And that's just something I think about all the time. I like your apocalyptic. Saying that is a really hard word to say. I think that take is pretty fresh because it's like, it's easier to build a website and the website used to be the marker of credibility.

It's like, do you have a website that's a check? Is it a good website? That's like a double check. Right. And it's easier to make that. It's easier to generate blog content. And so where's the barrier? Like there's no barrier. You know, and this is why people are thinking Google's in trouble because they're, you know, search is being attacked.

SEO is under threat from AI. My advertising model might follow. You know, websites page rank used to be the network of proof that you had value. If enough people linked to your site, that's like saying, Hey, you know, I'm Connor's websites, buddy. I believe in it. Like, okay, well now that thing has cachet. Well, if that goes away, then communities and networks like that are the way to say, Hey, I believe in this person and what they say.

So you're following on X or you're following on LinkedIn or your private community. Those matter so, so much more, and I think it's only going to keep rising. So it's a very smart way to build companies these days. And I know there's a whole movement around community first, product second. There's a lot of, there's a lot of merit to that.

Let's talk a little bit about company culture stuff, because I know that's one of the things that we want to talk about. So you had a lot of remote employees. Um, we also navigate something similar where we had to build like a remote company culture, philanthropy in different cities, like social activities that are happening online.

How did you navigate a remote, uh, company culture? The way in which we created a great culture was almost by accident. I had hired a new engineer and she was very nervous about making sure she was doing her job well. And she wanted to get a lot of feedback, which is awesome. I love it. And so she said, would it be okay if I just started kind of tweeting out my Slack channel?

What the hell I'm up to? And I said, yeah. So she started live blogging her day in Slack and I would give constant feedback around what she was tweeting, tweeting, slacking. And what was amazing was other people in the company started jumping in to help. Right. They would say, Oh, I didn't know I could do that.

Thanks. I just learned from you. Or, Oh, let me save you eight hours of time. Don't go down that path. Do you, you know, try this instead. And it, it just was like this, like my, my, that they just clicked in my head. Immediately. We have active presence for people all day long. You're educating your peers. You are not wasting time between standups.

You're not gonna spend eight hours stuck in something. Someone's gonna jump in and help you. And we scaled that culture up to 150 people in a product design and engineering team. We were all live blogging their days constantly. It's a ton of content. Don't get me wrong. You can get lost in that content, but our cycle time was so, so fast.

No one had to wait to the next day. And it was just remarkable. You know, it scared a lot of people. I would disclose this in the hiring process. We're the kind of company that doesn't want to wait. If you're stuck, we want to know right away. So we hire people who are intellectually vulnerable and will participate in this culture.

If it's not for you, that's okay. We don't need you to solve problems uniquely to be successful here. We need you to help the team, like we need to be globally optimized. So if you're stuck, just talk about it. Half the time when you write something out loud, you solve it yourself. And the other half the time, your team jumps in and solves it with you.

And then you're not wasting another day's cycle on this thing.

Uh, almost like a consistency and like company culture. So by you posting consistently, people feel like they're aligned, that you understand what problems the company is facing, you know, the magic of in person is you feel the energy of other people building. I think this is this, this, you know, I don't want to compare and contrast, but this provided that in the digital space.

It also created that, I know what's going on feeling, you know, it's sort of the ultimate transparency. You don't have to. To think, Oh, I've never talked to this person. So their team, they must be screwing me over deliberately. It's like, go look at their channel. You can see what they're struggling with, what they're thinking about, why they're gummed up.

And that would allow managers to get together and do global optimization on the system. So I, you know, I can't sing enough praises here. I thought it was truly a fantastic culture. I like these things. That's fun organically. Like for us, we had special interest groups where it's like. Employee led employee engagement.

So they're like, I'm passionate about this thing. I'm going to lead this group. And because we had. Thousands of people, we had to have a culture that was from like, everyone was engaged in it, everyone was making it, it had to be decentralized essentially. So like part of their onboarding was like. What do you want to join?

Like, do you want to be involved in philanthropy? Do you want to be involved in, I think one of the biggest ones was anime and manga, and it was just like gifts of like anime episodes and there's thousands of them. Attack on Titan for life. Yeah. Like it was the most active group and I love that stuff. I got a lot of inspiration for this from the indie builders on Twitter.

So I, if someone launches, I told you earlier, if people will launch products, I have like so much love and respect for them. So people launching their first SAS product ever. If I see that on Twitter, you might get a follow for me and you're, you know, in your follower notifications and watching people just build in public like that, I learned stuff, you know, I learned so much stuff and it increases my rate of learning.

And so just porting that into the company culture was pretty awesome. The other thing is even as a leader inside your company, verbalizing what you're struggling with and thinking about can often elicit a ton of interesting insights. You know, obviously there's a sensitive line on certain things you might be thinking about or not, but there's a lot of times you're like, Hey, I just don't know how this feature is going to evolve.

These are my concerns. And you might have people from random corners, the company jumping in with deep insights saying, have you thought about this? And going, no, I'm so glad you're on the team. Thanks for helping out with this. I think that's a pretty powerful thing. If you can be a CEO or be a founder and be vulnerable and, and share what's happening.

And I found as a manager. That vulnerability goes a long way to truly creating the right type of relationship between you and the folks that you work with. It's just, again, adulthood is an illusion. I don't want to seem like I have the answers because that's going to turn you off from raising problems or solutions to me.

And then we all fail together. I'd rather win together because I told you, I didn't know stuff and you helped out or you didn't either. And, you know, we just keep grinding away, but that's, that's, that's. That's sort of the only way to fly in my book. Aaron, I wanted to ask you about the two exits. So how did you run that process?

Where were you at in your life? Working out of a basement. So for Price Intelligently, which was then became ProfitWell, the process, it took a little while to get going. The business was self sustaining and growing. I mean, to be clear, it didn't need necessarily to sell. But as a management, you're sorry, as a, you know, a board, we got together and just had a number of discussions around the way the ecosystem was evolving and that there were probably some one plus one equals three opportunities out there.

And we should go figure out what they are before we commit to new paths. That may or may not succeed, but would fundamentally alter the business forever. Right. There's new projects we could do. Maybe it takes raising money. Maybe it takes jettisoning old things. You know, what's our level of conviction?

What are the opportunities to do greater things with someone else combined? And you know, that, that started as a kind of talk to a few people here and there, and then ultimately became an actual process where 10 to 12 people were engaged simultaneously. Um, for me, I got to advise that one from afar in the sense that I was, you know, uh, a non operating board member, co founder on this, trying to help make this thing work and giving advice and, and trying to keep all the parties, you know, happy and enthused and keep our psychology duct tape together.

Cause it's really taxing, even when you're not in it, you know, you can talk to Patrick and he can tell you, you know, cause he was running it firsthand, how insanely challenging that was emotionally for him. And then the Blissfully acquisition, that one's, you know, I have a lot more thoughts on that because we were growing, but we weren't growing like bonkers.

If you're in a venture backed startup game, you've got a, you've got a clock. Right. And until you hit that, that, you know, escape velocity of enough customers to eclipse your costs, you really have to understand, or you can be able to fundraise more money or not. And we were in a situation where we had built too much customers, valued And so our growth prospects probably required a little bit of a reset on the product.

We needed to narrow the product to expand growth, which is counterintuitive, but it's the right way to do it. And that's a lesson I've learned the hard way several times. So with that acquisition by vendor, they were really looking for a certain type of, you know, technology, technology team, um, SAS catalog and all this stuff.

So that was a real one plus one equals three because they got exactly what they needed in the team that could build and grow that. And we got to jettison parts of the product that were going to hold, hold us back, whether it was on our own opportunity or theirs. And in fact, it was such a great story that it was six months after acquisition, maybe even less.

Uh, I went out to the CEO, the CFO and myself and we fundraised 150 million series B. So, you know, that was a pretty crazy journey, but that, that process of, of exiting was just so complicated because we were trying to. Suss out our own runway, our own ability to raise money. This one plus one equals three equation.

But once you see what could be, it's hard to unsee it. Like that just made so much sense. It was hard not to go through with it. But even when all parties want a deal to happen, it can still fall apart. It's still incredibly painful and nerve wracking. It's like showing up to this party that everybody should be so excited, but you're just so defeated and that it's female feel so surreal also at the same time.

So like when cash floated into my account, it was like hard to, I'm like looking at, I'm like, is that, it's anti climactic, right? Yeah, it's anti climactic. Yeah. So there's like couple moments that I think happen. Like one is like you're on the legal call and everyone says like, yep, yep, yep. And you go around the table and everyone gives a thumbs up.

And then the other is like waiting either in a bank or on your phone for the wire transfer to go through. When's that wire gonna land? . Yeah. And there's no like champagne or like celebration or anything like that, unless you do, unless. And this was during COVID time still. So there was no like, Hey, let's get together and celebrate and all.

We didn't get together. We still haven't, uh, you know, years later. And, uh, it sucks. That's a, that's, that's, that's a little bit of a negative for building in the remote world, whether it was by choice or forced on you. I, I was calling the banker and broker. Probably several times. Oh, they were calling me actually several times a day.

And I was talking to my co founders like nonstop, like navigating the different deal terms and making sure that everything was square. And then once the deal closes, it's like quiet. It's like, but then you have a whole bunch of work you have to do. You have to make sure that the employee experience is good.

The transition plan. Like go smoothly. How did you guys kind of work that as nerve wracking and anticlimactic at the same time that the legal and sale process was integrating team cultures afterwards on the blissfully the vendor side of things was just the most challenging thing to do because And for no one's fault, let me just be clear here.

Like I just, it's just hard to smash cultures up together. They have their own culture. They had their own tech stack. It was different. You know, how do you tell people things are going to change in ways that they probably didn't sign up for? They definitely didn't sign up for it. They may not agree with often.

I felt like Darth Vader, like I was coming in and just killing things that people valued and forcing my will on stuff. And for what it's worth, of course, I think I'm this very empathetic, transparent, vulnerable person. People listening to this at work, they feel free to disagree and shoot me snide comments in the comments.

Yeah, you have to make a lot of hard calls. I mean, I think entrepreneurs know this, but saying no is usually more important than saying yes. Um, and what we said no to really mattered and the speed at which you can say no and move forward matters a ton. In order to make culture work, you have to get up close and personal with folks and you're probably going to get hurt.

Even if you see the blogic in it, you're still going to just bristle and feel uncomfortable. But that's what it takes to make a culture work is sort of being clear about what you're not going to do, uh, being transparent and being swift with it. Because the longer you let things linger in the in between land You've got portions of your company that are kind of separating and you may not realize it.

I think something that you do really well is, is probably communicate or over communicate. So I imagine that's helpful with the exit process because ambiguity hurts. Ambiguity kills. The thing that hurt me early on with that was I wanted to be respectful that our culture was coming into an existing culture.

And so I didn't want to overplay my thoughts. I wanted to make sure that I. Really had absorbed the culture and the vibe of the company. I think I had mixed results with that, frankly, like it's a hard thing to do because I also want to move at warp speed. Like, Hey, we've got this combined opportunity.

Let's go, go, go, go, go. Right. I want to touch on, uh, really quickly, how is life for you now? And what are some things that you're excited about? What's exciting for me right now is that the world is changing so fast and AI is evolving so fast. I don't think much of what we do today is going to look the same in 10 years.

Uh, at least in the software space. I think it's going to be fairly dramatic, and I am very excited to be a part of that because I am a technologist, I'm a product builder, and I love culture and science fiction, and all of that has come together in this kind of new era we're heading into, so I could not be more jazzed.

But setting aside my startup ambitions, because I am not done, like, there's a lot more I want to do, life has been pretty good because I've been focusing on my health, which has taken a huge toll over the last couple of years, and it's no one's fault. It's just Look, if you've got something huge, you're pursuing and you're merging cultures and you're merging products, like I, I'm going to burn the candle at both ends and having the headspace to think deeply about things cannot be.

Uh, overrated. I think if you're a leader at a company and you probably do this, finding time to get away, to think deeply from your business is where some of the most transformative ideas come from. And anybody in the business could provide those, but when you're in the thick of it, operating, operating, operating, it's easy to get lost in.

The drama of the day or the micro opportunity or whatever, you know, think you're trying to solve. I've had now a couple months of just thinking and that's been awesome. I spend too much time with myself recently and I'm trying to spend some more time with other people. That's been great. Like so focusing more on like a relationships and I think I had my head down so much as a poke it out and start talking to other entrepreneurs about what makes them excited and.

And, uh, learn about other things that have you, have you found that helpful for you to clarify what's been stewing around in your own, uh, I wish I didn't wait, like, I know that, like, as a CEO, we're in a company, you have 14, 18 meetings a day, but like, it's so valuable to connect with other folks. I wish I was doing it earlier when my calendar went from fully packed to nothing, any request for meeting that came in, I would just take.

Because I felt uncomfortable. Yeah, I'm like, no, my day can't be empty. I need something on it. Fill the calendar. So actually for the first couple of weeks, I actually did have a pack calendar and then I caught myself going, what the hell are you doing, dude? Like this doesn't, this doesn't make sense. You shouldn't be doing this right now.

It's a little sad that our happiness is dependent on, on digital meetings on zoom and meeting with random people. Um, but I think in a way that like post exit founders is helpful because then you're just meeting with other people, going through some more stuff. It's, it's helpful to kind of reconnect on that.

Right. You go to a networking event or something. Oh, who are you and what do you do? Or what have you done? And then, you know, I know it's like a trope. People might. We hear you and then move on to the next person, but it's not interesting enough. Right. And, and, and I'm not judging that, but, but I think when you spend all your time in that space and you exit it and you go to a dinner party and say, what are you doing?

I'm like, I'm just, I take walk. If you take an hour long walk around an Island with my wife every morning, like honestly, that was the highlight of my day for a long while. It's awesome. Still. It's not a conversation at dinner that people get excited about, but Hey, I feel great. I'm reading this fantasy book.

It's fantastic. Or like, you know, it's just, in a way I'm kind of enjoying that. Like whenever someone asks me what I do, I just change the answer every time because it's a different answer. Like I'm, I'm doing something different, right? Well, I really appreciate the chat. Um, Aaron, do you have a place where you want people to find you if they want to reach out or connect with you?

I'm I'm I'm most active on Twitter. X. com forward slash Aaron White. That's fantastic. Um, Aaron, so good to have you on the pod. I appreciate the chat and uh, we'll be in touch. Connor, thank you so much. This was awesome. Be sure to subscribe to our podcast. Thanks for listening and stay tuned for more episodes on navigating the thrilling path of entrepreneurship.