Taylor Crane - Founder of Fractional Jobs: Pros and Cons of Taking Venture Capital, Bootstrapping vs. Taking Investment, and Cost-Effective Acquisition

Taylor Crane  00:00

We go from doing four games a day to doing forty games a day, literally overnight, which was like, you know that the meme when you're in the roller coaster and you're just going at warp speed, that's what it felt like. It was one of the greatest feelings, professionally, I've ever had. Also terrifying at the same time.

Callan Harrington  00:16

You're listening to That Worked, a show that breaks down the careers of top founders and executives and pulls out those key items that led to their success. I'm your host, Callan Harrington, founder of Flashgrowth, and I couldn't be more excited that you're here. Welcome back, everyone, to another episode of That Worked. This week, I'm joined by Taylor Crane. Taylor is the founder of Fractional Jobs. Fractional Jobs is a job board for startups to reach and recruit fractional talent. These are part time leaders embedded into startups to help them scale. Before Fractional Jobs, Taylor founded Clubs Poker, which he started in 2020 and sold in 2023. This episode is unlike any that I've done before. Typically, I'll have founders on here who have seen a ton of success and are actively growing their startups. This episode is largely based on Taylor's experience founding and ultimately winding down Clubs Poker. And it was a fascinating conversation. Taylor didn't hold back on a single thing. We talked about how he turned a problem he was experiencing into a business, how they very cheaply acquired a competitor, and how rapidly they grew as a result of that, which I thought was a really interesting tactic. And a good portion of the conversation centered around the pros and cons of taking venture capital, how it impacts your business, when it makes sense to take venture capital, and when it doesn't make sense to take on venture capital. And I've said it multiple times on the show before, but I think it is so important to understand the different ways that you can capitalize your business, whether that's operating from personal savings, taking venture capital, taking bank capital, or any other type of funding means that you can think of. And the reality is, there is no single way to do it. And it all comes down to understanding what your goals are and really understanding the type of business that you want to create. Taylor walked us through his personal experience. And what's super interesting is that since recording this episode, Taylor's new company, Fractional Jobs has gotten off to a great start. Knowing that makes his conversation that much more interesting, as he talks about all those things he learned by going through Clubs Poker, and specifically what he would do differently based on those mistakes that he shares with us, when founding his next company. So it was so interesting to me. And with that, let's get to the show. Taylor, welcome to the show.

Taylor Crane  03:16

Thanks, Callan. Thanks for having me.

Callan Harrington  03:17

Yeah, I am very interested in this one, and mostly because I think this is gonna be a different angle than a lot of the ones that we've taken. And we'll get into that a little bit. But before we do, tell me about what ended your up-and-coming poker career? Because, as I understand it, you're doing poker professionally, correct?

Taylor Crane  03:38

I would call it semi-professionally. So the context is, I was a poker player for four years throughout college. So I was still a student, at college, but I was playing poker in all of my free time, if you will. Poker was really my passion in life at the time. Yeah, so I played every day, I studied poker, I had a poker coach, and I was making money playing poker too. When I was playing online poker, I was making about twenty-five to fifty dollars an hour. And then when I was playing Live Poker, I was making about sixty dollars an hour. And that was over a sample of about, you know, several hundred thousand hands played. And so, by no means was I building wealth here, right? But it was still pretty good money, especially for a college student, it was pretty good money, and I was quite happy with it and, you know, impressed with the ability to play a game and make money doing it. And, you know, it carried me throughout all four years of college, and it got to the point were in senior year of college, you know, all my friends were looking to get, you know, jobs. They were interviewing, they were landing jobs, you know, even months before graduating, and I was kind of of two minds on what I wanted to do post-college. There was definitely a path for me to become a professional poker player, graduate college, and like, continue on the trajectory that I was going down, and continue to put in work and get to that level. But it was also, you know, maybe I wanted to get a big boy job. I was also super interested in tech and startups. This was circa 2010 or so. And so like TechCrunch Disrupt was like a hot new thing, like that's kind of like the era of startups that I'm talking about here. And I was passionate about that as well, and thought, like, you know, maybe I can get into the startup scene and like, build a career that way. And so delay the decision for a while. So the way the story goes is, it's now April of my senior year, I had no plans after graduation. And I'm still playing poker in all of my free time. And one Friday morning rolls around. Fridays, I had no classes, and so my day was always I would play poker from 11am till about 3pm online, and then I would take a break. And then I would go to the casino, and I would play on Friday night, from 7pm until I couldn't keep my eyes open anymore. But instead, on this day, I woke up, I sat down for my 11am session, I loaded up the poker app, and the servers wouldn't load, it wouldn't connect to the servers. It's like, ah, that's weird, okay. I'm gonna go to FullTiltPoker.com, check the website, see what- if there's like a status message, like maybe they're down for maintenance or something? When are they gonna get back up? I was very annoyed that it was disrupting my perfectly planned schedule. And the website loads, and I'll never forget this, because the website itself did not load. What loaded instead was a blank page, and a massive Department of Justice and FBI logos in the center of the page. And I saw these logos, and immediately, I'm just like, oh, shit, like, just not- this does not look good. Mind you, by the way, I had many thousands of dollars on this- locked up on this site at the time, that are now suddenly in limbo, as well as like my whole, frankly, my life, my identity, was also suddenly in limbo. It was a very weird time, actually. And so, you know, long story short, what happened was online poker was very suddenly shut down in the US by the federal government, and I now, you know, thinking about my post-college, what's my career gonna look like? The decision was basically made for me. I had friends, poker friends specifically, that were already doing this professionally. And so they were scrambling in a very different way. And they were moving, they moved to Canada and Mexico and Australia, top three destinations. And for me, I kind of took it as a sign and said, you know what, this may be a blessing, maybe it's time to close the poker chapter of my life, and move on, and break into the startup scene in New York. And so that's what I ended up doing. So yeah, that's how a burgeoning poker career ended before it kind of really even started.

Callan Harrington  07:29

Here's a question. I think that's super interesting. Could you have moved to Vegas and done this full time there?

Taylor Crane  07:38

So I could have played live poker in Vegas, but not online poker. At the time, at least. Online Poker is now legal in Vegas, but it was years of gap in between. And live poker also, like living in Vegas, didn't really appeal to me. And I was way more interested in online poker. There was more money to be made in online poker, way more fun. Live poker is boring. Anyway. So no, not really appealing to me, but I did know people did that too.

Callan Harrington  08:02

Okay, so for you, it was, you really enjoyed playing online poker; live poker just wasn't appealing. So as a career, online poker is like, okay, I could do this. But if I've got to do this in person, that's just not- you're not as interested in moving into the destinations where you can do that, and just the actual function of it wasn't as fun for you.

Taylor Crane  08:22

If I was dead set on making poker my career, it would have been a no brainer to move to somewhere like Vegas. But because I was of two minds on it, and frankly, like, you know, I was frankly thinking, do I really want to build my career in poker? Honestly, I'm so glad that I didn't, because it's not as nearly as glamorous as it looks. And so because I was of two minds on it, it kind of just, it felt like a sign where it felt natural that like, you know what, you know, this is my time. Yeah.

Callan Harrington  08:48

Yeah, yeah, absolutely. And I know, of course, we're going to talk about how you got back into this. But before you got into this, where did you end up spending your time prior to getting back into poker?

Taylor Crane  08:57

So I spent ten years in the startup scene in New York. I was a PM by trade, so which is a product manager. So working with engineers and designers on authoring software across different industries, nothing to do with poker and gaming, ad tech and insurance tech, and real estate tech, et cetera. So yeah, I mean, I literally, poker was not part of my life anymore, and my life was now consumed by technology, and software, and startups, and building and scaling, you know, early stage businesses.

Callan Harrington  09:27

What was kind of the factor that brought it back?

Taylor Crane  09:30

Yeah. So it was quite unexpected. What ended up happening was, you know, and let's fast forward now, basically, ten years, so it's now March of 2020, and COVID had just hit. I find myself on a Zoom call with a bunch of my high school friends. And on this call, we're like, bored to tears, right? We're just like- I'm sure you remember those days. We're just talking, catching up, and you know, had no idea what to do with ourselves because we were all in lockdown. And one of us had the idea to try playing poker, like we used to back in high school. These are like the original kids that I started playing poker with in the first place. So they all looked at me to set up this poker game with our- amongst our friends on Zoom, you know, for obvious reasons. And so I do my Googling, and I'm like, okay, like, where do you play poker online today, I don't even know anymore. And what I learned was that it was the same as what it was in 2010. So it was PokerStars was like still the software that everyone used. And so we had to download desktop apps. And I'm trying to set this game up, it took thirty minutes, just to get us a game of friends playing a play money version of PokerStars. And I was so blown away, because I had worked in software now for ten years, I know how quickly software moves and how companies are intended- are supposed to like scale and improve the world through software. And it was the same software that I was playing on ten years ago, and I couldn't believe it. And so that was maybe epiphany moment number one. And then epiphany moment number two is, after we finally got the game up and running with my high school friends on the Zoom call, we played for four hours, and we had so much fun. It was so much fun. And so then that was really lead into the idea which became ClubsPoker, the realization that it was both so much fun to be doing this with our friends- we hadn't done this in, you know, ten, fifteen years, really- and that the software up today was so ill equipped to serve this purpose. And so what Clubs Poker became was a destination for groups of friends and online communities to come together to play poker amongst themselves for fun, you know, socially, for play money only. And that's what we built. And so that's how I found myself back in the poker world again, after so many years and not expecting it at all, of course, from a very different vantage point, though now from the business side versus the player side.

Callan Harrington  11:50

Yeah, you know, one of the things I'm curious about is, was this- you got back into this, you're playing with friends. My assumption is, is that it probably hit you pretty quick, like, man, I really do love doing this. Was it something like that, where it was just, I have to do this? Or was it, this is potentially a good opportunity, I've got to follow this?

Taylor Crane  12:10

It was moreso the latter. I don't remember having the point of view that, oh my God, I've missed playing so much, and I have to be playing again. Especially because, like, when I'm playing with my high school friends, I wasn't trying to really win their money, to be perfectly honest. Like, it was a very different mindset. And frankly, even after I started the company, I was trying to get myself back into a player's mindset. And I was playing again, I was playing online again, I was playing live again. And aside from the fact that my skills had atrophied so miserably, it was embarrassing to watch myself play, I had way less fun doing it. And I derived enjoyment from,and therefore, inspiration for the vision of the company from, the social elements of playing poker with friends and with groups of people for networking purposes, et cetera, not as a mechanism for profit, which is how I used to play the game. And so it was a very different mindset that I was in. And I was also, I guess, directly to your question, for me, it was more about the opportunity, It was like, can I marry my business acumen with my passion for poker in a way that, you know, builds an awesome company and carry the values forward that I believe in, without me needing to be a player? Because I think those days were done for me for several reasons.

Callan Harrington  13:22

Yeah. So you had this deeper spark of I want to bring people together. And this is a great medium to bring people together. And it sounds like you wouldn't have even thought about it like that. If you were to continue playing poker, like how you were, you would have never looked at it probably from that angle of, this is just bringing everybody together. Is that fair to say?

Taylor Crane  13:42

Definitely fair to say. And it's also fair to say that, therefore also would not have had startup and tech and software experience. And so, if I wanted to build a company, I don't even know- I don't even know what that would have looked like.

Callan Harrington  13:56

Yeah, what was kind of the spark that said, alright, I'm going to do this full time?

Taylor Crane  14:00

You know, it was a very weird time, COVID. And I had a full time job as lead PM at a startup in New York, and I had been there for like three years. I was so sick of it, to be honest, I was so ready to leave anyway, and then I'm working on this new idea. My dad's an entrepreneur as well, by the way, so I've always had this thought in my mind, I'm going to eventually be starting companies. And so this opportunity presents itself with myself and my co founder. And it was so obvious to me that this was the move. I was going to quit my job, and I was gonna give this thing a shot full time. What we decided to do was actually move to Denver during- get like a hacker house, Airbnb hacker house in Denver, and build the MVP, and then see where it goes at the end of the summer. And by the end of the summer, we were thinking about COVID will be over anyway, and we'll get a lot more clarity on what the world's gonna look like. Of course that wasn't true. So yeah, it was a super no brainer decision, honestly. It felt very natural, and it was- to be a founder and working on something that you have a very deep experience in, domain for, I just felt so well equipped to give it a shot. Basically, it was like there's nothing better gonna come around that's gonna make it even more obvious for me to take this leap. So this is what I'm gonna take that leap on. It just felt so obvious. Was the plan to raise venture capital from the start? Or when did that come about? No, definitely not. The plan was to start by bootstrapping it. The plan was to spend the summer building the MVP, launch the MVP, and start making revenue from it. And then just seeing where it was, and seeing if we could build the business, bootstrapping it. The venture capital route came in, when we launched the MVP. We got it done in the summer, which was insane. Launched the MVP, and honestly, by MVP, it's like not even an MVP. The thing barely worked, to be perfectly honest.

Callan Harrington  15:43

Just for our listeners real quick, so an MVP is a minimum viable product. And this is essentially the- you build the absolute minimum, that still will have some value to it, so that you get the feedback, and build and iterate on it. So, didn't mean to cut you off, just want to make sure everyone had that context on what MVP means.

Taylor Crane  15:59

Thank you for that. And so now, this was- take MVP, and then have it like break every twenty minutes, and that's what we were dealing with here. But we saw that people were still trying to use it, and still excited about the idea of it, even if it like totally didn't work when they tried to play. And so we were in this place where we were clearly on to something, we realized that we had way more to go before we could have a product that was even workable, and then even further to go to actually generate revenue from that. And so it kind of became like, okay, we can either bootstrap this, maybe not several years, but at least another year, before seeing a dollar come in. Or we can go out and raise venture capital. And so we decided to go out and raise venture capital. And so I raised a pre-seed from some pretty notable professional poker players, as well as a big VC firm out in Silicon Valley. And this was in, around, closed in around December 2020.

Callan Harrington  17:00

Gotcha. So you guys were in a situation, you're going to bootstrap it. And for our listeners, bootstrapping is essentially you're just growing from your own revenue and your own capital sources, whether it's your savings, or whatever else that might be. And then in order to speed that up, and to kind of get through- You had something. People still wanted to play this, despite the fact that there were bugs and issues coming up pretty quickly. And you raised venture capital. So what did that unlock for you guys? What were you able to start to do as a result of that, from like a growth perspective a development perspective, what did that look like?

Taylor Crane  17:32

So most importantly, it just took the pressure off of feeling, we're burning through our savings, right? So now we can pay ourselves a salary. And that was the biggest unlock, and then it basically bought us about eighteen months of runway that we could then look- you know, we can sort of be forward thinking for eighteen months. And we just, as opposed to again, just kind of thinking, you know, every day is: when are we going to start making money? And so there was definitely a pressure release in some ways. But it's funny I say that, because in other ways, I'm almost laughing at myself for saying that, because it's like a pressure release in some ways, but in so many other ways, it was a pressure intensifier. So I recand my original statement.

Callan Harrington  18:11

Well, let's talk about that. Where did it add pressure?

Taylor Crane  18:14

So, when you fundraise, you are pitching to investors that you don't know, or sometimes you do know, and what you're pitching them on, is that you're going to build a billion dollar company, and that you're going to change the world through this. And also, you're going to like, of course, return many multiples to them. And you're going to do all these amazing things, like this grand vision that you're selling them on, and then they believe you, and then they give you money for it. They give you their own money for it. And so I felt this, like immense combination of gratitude, frankly, and weight,to deliver on what I've just sold. And yeah, just feeling like, like, holy cow, this is like, I've got to do this. Even though I knew that, like, intuitively, we know that like nine out of ten startups fail, especially venture backed startups, numbers are even, you know, less, more like ninety-nine out of a hundred end up failing, but you still feel like no, you have to be the one. Otherwise you're toast in life. So, number one was the weight of the investors that are now on your cap table that you feel responsible for, but then number two is, you now have to basically change- not change necessarily, but like you have to think about building your business in a very, very specific way, because you are now swinging for the fences. And that requires certain decisions and calculus on like, how you build and grow the business. Very different from my natural instincts in a lot of ways on like how to build a business, and so, I had to re-architect in my mind and in the strategy how to satisfy the requirements of raising venture. And also you're now like, your next milestone is you need to raise venture again, because you take capital, your job is to spend the capital in a value maximizing way, I suppose, and then you go out and raise more capital again, do the same thing again. And so like, your goal now is how do I optimize the business to get to the seed round of funding, which is very different from optimizing the business for, let's say, cash flow, or making money, or like whatever other goals you might have. You have to grow at a certain rate, you have to achieve, you have to look impressive to investors, basically. And it's honestly orthogonal to building, in my opinion. People will disagree. I think it's orthogonal, just building a business.

Callan Harrington  20:25

Yeah, I think that's great insight from, kind of what you had just in general, and you talked about a couple things, you talked about, you know, when you raise venture capital, you're going for a billion dollar exit, and that is more of a, we're going to change the world type of product. And I think if you go into raising venture capital, and you're thinking anything less than that, or the idea doesn't need to have that in order to be a success, then you know, think about, do you need to go the venture capital route? Certain ideas, like if you're building an insurance carrier, you need to go venture capital. You're not going to bootstrap that to be that kind of business. If you're going to try to do an Uber and change everything, and you have to totally sweep out entire market overnight, you're gonna have to raise venture capital, just because that's where the most likely source of capital is going to come from. But a lot of businesses don't have to do it. There's other ways in which you can either capitalize the business, or you can build it on the side until you get to that point, as you mentioned, to get to cashflow positive, and continue to- you're going to grow slower, and that's okay for a lot of businesses. That's a lot of what I'm hearing. And that's a lot of what I think, kind of just in general, is, there's no one route. That is you have to do it this way, whether that's VC, whether that's bootstrapping, whether that's just you know, getting it funded by friends, family, or angel investors. So I think that's really interesting. I'm curious, as you guys started to grow this, what were some of those levers that like really led to some of the exponential growth? Because as I understand it, you guys grew pretty quickly, once you really started to get this under, like, once you started to build that momentum, this grew pretty quickly. Is that right?

Taylor Crane  22:13

In some ways, yes. I'm laughing, because I'm thinking of one specific thing that went to basically all of our growth, and despite all the other things that I tried, and so I want to tell that story. I also want to circle back to one thing you just said earlier about the different flavors of, like, building business, and raising venture capital, and going bootstrapped. And I would even take it a step further, and say perhaps it- an even controversial statement, that I think that raising venture capital is a bad deal for founders, for most founders, most of the time. And I don't even think of it anymore as different flavors, you can build a business by raising venture or you can build a business by bootstrapping, I think if it as, you should not build a business with venture capital unless you absolutely have to. There are like several criteria where it doesn't make sense to, but most of the time, I think it's a bad deal for founders. So I know a bit controversial, and I'm sure many people will disagree with me, but I had to like get that in there, because I feel like it's worth sort of like describing and also maybe even shedding light on. I think a whole generation of founders, like myself, have been sold on the idea that when you think about building a startup, you have to go venture. It's just like what we're told. Everything you read in the news about venture capitalists giving investing money, and you raise a C round, and this company's raising A round. And that's all we talk about, and I want people to feel, and know, that you can build very successful businesses without doing it. And you probably should, actually. So yeah, I know that's a bit of a tangent, but I felt compelled, Callen, to double-click on that. And now we can go back to the growth question, if you want to.

Callan Harrington  23:42

No, what I hear you saying is you should try to go without venture capital first. And if you fall into these specific scenarios, or you're in a situation where you absolutely have to, that's when you go venture capital. That's essentially what I heard. Is that correct?

Taylor Crane  24:03

Yeah, and I'll even expand on that a bit. Maybe the way to think about this is, at least in my mind, there are basically three reasons that you should raise venture capital. The first reason is the most obvious. And, Callan, you mentioned earlier, if you're building a business that simply just requires the capital, right, so you're building an Uber, or you're building SpaceX, would be a perfect example of requiring massive capital. So that's the reason number one, is the business you're building just simply just needs a large amount of capital. Reason number two that you would go venture capital, is if, I think if you're a founder that's already financially set, basically, if you already kind of made it financially, you're able to take care of yourself and your family. And you're now, you're not thinking so much about how do I achieve financial security, and instead you're thinking about like, how do I perhaps weave a legacy, or how do I build, if you want to build generational or multi-generational wealth, it's kind of the next level for you. That would be a reason to go venture as well, because you get to take a much bigger swing to get to a potentially bigger outcome, and if you don't hit the outcome, it's not going to impact you or your family's life in a meaningful way. That's number two. And then number three is, if you're a founder that simply, your life's mission or work is to build this company, and you don't- your goal is to change the world, right? Period. If you make money doing it, if you make a billion dollars doing it, that's awesome. If you also made one dollar doing it, that's fine, too. And that's awesome. And I know founders personally that are like that. One of my clients, actually, she's brilliant, and her mission in life is to build this company that she's building. And so she's raising venture. That's what you should do. If you don't fit that criteria, I don't think you should go venture. I did not fit that criteria, and in hindsight, well, it's complicated to look in hindsight, because I've kind of I felt like I had to go venture, but for other reasons. Only put it this way, my next company is not going to be a venture backed company no matter what. So yeah, that's my perspective. Yeah, end of one, but that's how I feel.

Callan Harrington  25:57

Well, a couple of things. One, I think the scenarios that you described, I agree with all three of those scenarios. And I'm not saying that those are the only scenarios or not. I totally get that's what you're saying. I totally respect that.

Taylor Crane  26:09

Yeah, perhaps a bit hyperbolic.

Callan Harrington  26:11

Well, regardless, I think, to me, the moral of the story is this. When you're starting out a business, I think it is so important, and I've done both. I've done, not necessarily as a founder, but I've been in many venture capital backed companies, and in bootstrapped companies as well. And I think one of the things that I learned was, when you're at the very start, be very intentional, be very clear on what your goals are. And you hit one in particular, I thought that was super interesting was, I'm a person that has to change the world. And there's absolutely nothing wrong with that, in that world, you're gonna have to go venture. If you're somebody that says, I want to build a- one of the coolest concepts is, small giants. Small giants are, the concept is, I'm gonna build a company, all I care about is that the company is great. And they don't want to raise capital from, whether it's venture, or P, or whatever it might be, because they don't want to give up any control whatsoever on the vision and the direction of the company, which is kind of tying that back to something that you said in the beginning, where once you took venture, and that's very true, when you do take venture, you are tied to the, I have to create a massive, massive exit, because that is the game. And the more clearer you are up front on what you want to get out of this business, the more flexibility that you have, and more- You could always go venture later. There's tons of companies that, you know, didn't raise their Series A until they were already like, it was a hundred million dolla Series A.

Taylor Crane  27:40

Yeah.

Callan Harrington  27:41

So, you don't have to do it right out of the gate. Certain things, no question, if you're going to try it. Open AI, like, you're going to have to raise venture capital right out of the gate, because you need a lot of engineers, a lot of research, and that may never happen. So I think you brought up really, really, really interesting points. I hear what you're saying in that, like, you know, I gave up, I was very descriptive and like this, is it, but the reality is, I think those three are all absolute use cases. But figure out what you want to do right from the gate.

Taylor Crane  28:08

Yeah.

Callan Harrington  28:09

That's so important to what it is, because you'll give yourself more options later. But if you know right from the gate, that you're trying to change the world, you're gonna probably have to go venture capital, you don't really have a choice on that.

Taylor Crane  28:20

Exactly correct.

Callan Harrington  28:21

All right. Cool. Great conversation. I loved it. So tell us about the growth. You mentioned that there's this one event that had a massive impact. Let's talk about that. I'd love to hear that story.

Taylor Crane  28:30

Yeah, so, I have so many thoughts on this. Growth and marketing was probably, in general, my weakest area on all the whole Clubs Poker journey. For the most part, couldn't get any momentum going and couldn't get any, just figure out or unlock, any growth mechanism, with one exception, or really, I guess, actually two exceptions. There were two things that we did that I think led to our growth. And before I get into them, I want to just describe the growth trajectory that we had. So on average, through the life of the company, we've been growing at a rate of about 20% month over month, which is really solid. And at our peak, we were doing about 7000 monthly active users that were playing poker games with their friends and with online communities on Clubs Poker. Most of the things that I did had absolutely no impact on that growth. I think there were two exceptions. The first is the more of the product itself, and like our product- what's called the product-led growth play. The way the product works is, if you're a game host and you want to invite your friends for a poker night, you come to ClubsPoker.com, you create an account, and then you invite your friends by sending them a link. And your friends just join the table, and sit down, and start playing, and there's no signup process for them. So it made it super simple to onboard your friends and start playing, and your friends didn't have to go through any cumbersome signup. And here's the interesting part, or the idea I'm patting myself on the back a bit, but while you're playing, we ask you to sign up if you want to. Optional. Here are the benefits of doing so: you get to save your game history, et cetera, all other features, et cetera. And so when you're playing poker, eight times out of ten, you're folding your hand, right. So you're not even playing the actual hand that's happening at the moment. So you have downtime. And so we saw so many signups that way, people that were, frankly, just bored, and just like, oh, you know, let me sign up, I might as well, I'm already here. And so what we saw was a game host, on average, would recruit about five new players into Clubs Poker, to grow, to play a poker night. And then we would then convert 15% of those new players into their own game hosts for new games to host with new groups of friends. And so you see a pretty obvious viral loop there, that we inherently built into the product, that certainly contributed to quite a bit of our growth. However, the more interesting story, and the more growth hacky type thing that I did, was the very first thing I did after we launched. So we launched, we're doing about, I think, it was like four, on average, four poker games per day, were happening on the platform. And that was just through word of mouth and through, like, I posted in a few forums and stuff. And like, we got some, like, initial users that way, doing four games a day, which by the way, was awesome on its own. We're like, oh my God, people are actually using the product. So cool. And then I emailed every single game host that played on Clubs, and I- with a personalized email, that was five questions. One of the questions was, how did you hear about us? And someone responded, and was like, oh, well, you know, me and my friends have been playing on this competitor for like ten years now, and unfortunately, they're shutting down. And so we had to, like find a new platform to play on, and we're so thankful that we found you. And, because your, the product, is even better, and like we had so much fun, and we're gonna keep playing with you guys now. And I was like, whoa, woah, hold on. What did you say? Our competitor that's been around for ten years is shutting down? Okay, that's interesting. So I go to their website, and check out the blog post, the latest blog post, and it was a farewell post from the founder, that was, hey, guys, we had a good run. And, you know, server costs this, whatever, and we're going to wind down. And so I messaged the founder on LinkedIn, and I said, hey, would you be open to a quick chat, like over Zoom? We got on a Zoom call, and basically, I was like, hey, you know, I'm building a poker app for friends too, and great minds think alike, it's such a bummer to hear that you're winding down. Would you be open to passing the baton to us? Let us carry this vision forward. I'll buy your company, and his eyes lit up, and he was like, yeah, please, please take this from me. And so he sent me a bunch of numbers on database and user numbers and traffic and stuff. And I did some, like back-of-the-envelope math really quickly on like, what this might be worth to us. And I made him an offer for five thousand dollars to buy the company. And he was immediately, yes, please take it off my hands. Because in his mind, he was about to get zero, and now he gets five thousand dollars. And he had a job elsewhere. It wasn't a full time thing anymore, anyway. I think it might have been for a while. And so we acquired a basically a user database of 165,000 poker players that were playing with friends over the last ten years. And then like the domain name as well. So like, you know, whatever traffic the domain was getting, we would redirect. In my mind, I'm thinking, holy cow, we now have 165,000 users that I'm going to remarket with emails to, and we're going to convert all these users into Clubs users, this is amazing. Zero out of ten. I don't know if it was my email marketing skills, or lack of actually, what I really think is email marketing, especially to email that signed up like seven years ago on the site is like super stale is not a thing. And it was an absolute waste of time. I tried so hard. I went down, so deep down, these rabbit holes of email, and deliverability metrics, your SPF and DKIM certificates and stuff. Total waste of time. But the domain name was interesting, because like now, the domain name, we redirected. And what I was thinking in my head was, cool, we will get their traffic. So if you're typing in the competitors, bluffapp is the name. So if you type in bluffapp.com, you would redirect to Clubs Poker, so we would capture you, and like, we would hopefully convert you there. And that'd be awesome. That'd be nice. We would get some users that way. And we did. But what I didn't realize, was that this company, this product, has ten years of backlinks on Google. And so, on Reddit, and tons of different sources, Reddit and other blogs and forums, that were talking about this site for ten years now. And so immediately, we bumped the top of the front page of Google, across a number of different search terms. And so if you search "play poker with friends," we're now at number two on the Google. But at the start, we were maybe number ten or so, which is still amazing for us. And so what ended up happening was we redirect the domain name, and we go from doing four games a day to doing forty games a day, literally overnight, which was like, you know that the meme with you're in the roller coaster, and you're just going at warp speed. That's what it felt like. It was one of the greatest feelings, professionally, I've ever had. Also terrifying at the same time. So then that's what kicks off the growth engine. And so now, you know, Google recognizes us out of nowhere, we're on the front page of Google, and then we have a good product that people want to use, and so it just continuously ranks higher and higher and higher, and it gets to the number two slot across a number of different search terms. And that is what led to our 20% month over month growth on average. Everything else I did after that did absolutely nothing. Influencer marketing, nothing. Writing my own SEO content, nothing. I hired a marketing agency, nothing. Social media, nothing. I don't even know, you know, I probably did other things too. I basically tried to teach myself marketing. I took a course, and I paid a lot of money for a course. And I was like learning marketing at night and trying to implement it during the day at my quote unquote day job at, you know, CEO of Clubs Poker, and not a good strategy. And, you know, got nowhere. And so, what was so funny to me about our growth is, throughout the whole journey, like two and a half, three years of Clubs Poker, honestly, I felt emotionally like I was eating shit every single day. And I was just failing, left and right, constantly. In a lot of ways I was. There were some really dark moments throughout the journey, moments where even I was hours away from shutting down the company, and just throwing in the towel. And throughout all of that, the backdrop was we just were putting up impressive numbers over and over and over again. So literally facing depression, because I felt this company was doomed to failure any day now. And I was looking at our Mixpanel, and we grew 50% over the previous month. And it was really funny. I'm laughing at it now. I was not laughing at the time, it felt really anxiety producing at the time, but it is a funny backdrop to the whole thing. So that's been our growth. I guess one of my takeaways is this idea of finding a competitor in your industry, or competitors, that like, maybe have been around for a while, aren't doing particularly well, but have some domain- what's called domain reputation. What's the technical term? I think it's domain reputation.

Callan Harrington  36:35

Domain authority.

Taylor Crane  36:36

Thank you. Authority. Thank you. That's the word I was looking for. And have backlinks, et cetera, if you're able to scoop them up for cheap, it's, yeah, could be a really, really interesting idea. And now when I think about new ideas, and I'm working on- I'm potentially thinking of one right now- one of the first things I'm doing is Googling and like finding competitors, that I feel like fit that Goldilocks, have history, but aren't doing well, and like the founder's probably willing to, you know, get it off their plate pretty quickly kind of thing. Because I think it's kind of cool, and it worked phenomenally well for Clubs.

Callan Harrington  37:05

So what I find to be the most fascinating about that is you had all these users, you couldn't convert them, like it was very, very, very, very difficult to convert these users in a deep platform from there to your platform. But it was this thing that you didn't even think of, they had just a great domain, massive domain authority, great SEO out of it, and that's what bolstered all of it. I think is such a cool story. So you were hitting these big growth numbers, what ended up happening?

Taylor Crane  37:36

Yeah, so growth is happening all throughout 2021. And then 2022 rolls around, and this is when I need to go out and raise more capital, right, because we're running out of money. This is the name of the game, right? We spent too much money, not making any revenue, we're prioritizing growth, and now I need to go out and raise my seed round. And so I was targeting a three million dollar raise. I go out to raise capital in, you know, I really started the process in like March of 2022, and it starts picking up speed or steam in April 2022 or so. And as it's picking up steam, by picking up steam, I mean, like I'm finally getting the intros that I want, I'm getting in front of like some of the top firms in the country, and as this is happening, the financial markets are tanking. And I had a very Web3 focused pitch also, and the crypto markets are literally going to the floor, the weeks that I'm meeting some of the top crypto firms in the country. And so the timing just could not have been worse. I don't want to say, you know, if it was different timing, I would have been successful. I don't really know. And nor do I think it's productive to think that way. But there's no doubt that the time he was playing against me pretty significantly. And so I spent six months trying to fundraise and just getting punched in the face all day long. It was miserable. And then, you know, eventually it became clear that it wasn't going to happen. I looked at the bank account, and it wasn't the first time I looked at the bank account, you know, I metaphorically looked at the bank account, and you know, the writing was on the wall. And so we decided to wind down operations and lay off the team, but just save enough money in the bank to like keep the site up and running, because I could not shut it down. Because we had 7000 monthly actives, and I just couldn't do that. So kept the money in the bank. And then what ended up happening was we got acquired kind of out of nowhere. I got approached by a firm, I can't share too much, but it's a nice cherry on top or end of the story, we ended up getting acquired. And so very thankful that I did keep the site up and running even though we wound down operations. And that closed the chapter, but at the same time now like the company is owned by another company, and I'm excited to see what they do. And yeah, I can't say more, but that's- yeah, so I'm excited for whatever the next chapter ends up being for Clubs.

Callan Harrington  39:48

Yeah, you're excited to see it live on what I'm hearing you say is.

Taylor Crane  39:52

Yeah, exactly.

Callan Harrington  39:53

It was something that put a positive ending on what could have been a negative ending, and you got to see it continue to live on. You know, one of the things that just to circle back here that I think is something that people should definitely be cognizant about is, you talked about the crypto markets and the Web3. And that's another thing that, you know, depending- now granted in this world at that timing, yeah, you were running into a brick wall. Just within a couple of months after that, most of the capital markets pretty much dried up altogether, like it was almost- I don't want to say a freeze, but unless you were getting cash from your current investors to kind of hold you through this, that Q4 2022 is really when things slowed down dramatically. But I've been in a similar scenario before, and we were also in the, at that time, it would have been more of the crypto blockchain. They go on highs, and they go on lows. And with AI, we're seeing it at a really big high right now. That could stay high for a while because it is such a monumental change in technology, but the crypto ones probably had the biggest wave of ups and downs of any of them that I've seen. But it happens in fintech, it happens in insurtech, it happens in healthcare, it happens in all sorts of different ones, but some are more drastic than others. And it's just something also to think about when you're going into this, there's no way to predict it. I think we all know that we can't predict the markets. We've tried over for hundreds and hundreds of years, and you can't predict that. So just something to think about. I think that was a really good point. So Taylor, let me ask you this, what comes next now? You mentioned you're thinking about an idea. Is this, I have to do this? Again, not necessarily poker, but just like in general, is it this itch where like, I have to do this?

Taylor Crane  41:42

Well, it sort of is. And it's kind of funny, because I think I've alluded to, at least a little bit, you know, in our chat that the Clubs Poker journey, although I'm describing a lot of highs and fun moments, you know, it was, it was a really tough few years, extraordinarily tough, and I did not frankly, enjoy the day to day experience at all. However, at no point in the entire journey did I think that maybe starting companies was not for me. It was always like, okay, this is a hell of a lot tougher than I expected. And like, this really sucks, but hey, at least I'm better equipped now for the second one. And so my ambition is very much to keep starting companies, and this one will be a bootstrapped one, or the next one will be a bootstrapped one. I'm not actively working on any specific idea yet, but I'm kind of beginning to play around with it. Because I am bootstrapping what I am doing is I am now a what's called a fractional head of product. And so I'm working with three startups at a time, early stage startups, handling all their product strategy work, and doing it for about ten hours a week for each client. It's so much fun, I so enjoy it. Product is my bread and butter, right? It's what I did for ten years before Clubs Poker, and I get to spend time in several early stage startups at once. I'm honestly having- it's one of the best times in my career genuinely like day to day work that I can honestly remember. But the ambition here is I'm going to be generating income again, frankly, for the first time in a while, and then save some hours a week to be working on new ideas and investing, you know, my income into these ideas basically in a bootstrapped manner. And so that is the ambition, that is the mechanism, or the practice that I'm in the process of building right now. Yeah, and I'm really excited about it.

Callan Harrington  43:27

I got a couple questions. One, if you're having that much fun, why stop doing it?

Taylor Crane  43:34

Why stop and go into a new company full time?  I'm a masochist, I guess. I don't know. I think- I don't actually have- that's a great question. I'm gonna have to think about that one later. But I still, at the same time, my thing, the thing I want to be doing is building companies. It's just there's no other way around it. I think that like the consulting work is probably a bit of a honeymoon period, if I'm being perfectly honest. Maybe not actually, it would be awesome if it wasn't, but this all has a higher purpose here. And like, so I will. It's really funny, because I think so positively about this next company I start, this bootstrap company, this is going to be the one that I enjoy the ride, and I'm going to love building every moment of it, which is what I thought before I started Clubs Poker. And that turned out not to be true. So I could be totally delusional. I don't know. We can talk in a few years, and I'll let you know, but my hope is that with a lot more scar tissue, and a lot more learnings, and a lot more knowledge, wisdom, if you will, I'll be able to approach the next company with a more like, Namaste mindset, and enjoy the experience better and hopefully, also, you know, have an even bigger outcome, like Clubs.

Callan Harrington  43:37

Yeah.  Correct me if I'm wrong, but what I'm hearing is that you're having fun, but the Club's chapter is closed, but the entrepreneurship chapter is not closed yet.

Taylor Crane  44:50

 Correct. Exactly correct, yeah.

Callan Harrington  44:52

Yeah. You still have an itch to scratch, which, and if you don't, you don't want to live with this what if or I've gotta at least try it and get some closure out of it.

Taylor Crane  45:01

Yeah.

Callan Harrington  45:02

What are the top things that you would do different, are you planning to do different, in this startup than you did in your past?

Taylor Crane  45:08

Well, the one obvious one would be bootstrapping over raising venture. Right? We talked about that. I think, and I hope, that I'm better prepared emotionally to handle the highs and lows. And there are certain tactics and sort of behaviors that I think that I practice now that I think will lend itself to having a more grounded experience in in building this company, you know, wherever the next company is. And so that's probably the number one thing that comes to mind. I mean, there are other things too, like, I do hope to be more like public in sharing the journey. Frankly, for Clubs, I was so wound up, anxiety wise, and frankly, I don't want to say embarrassed but afraid, and what I'm getting at is, I didn't post much, I didn't share much, I didn't talk much about the journey while it was happening. Because I felt a failure while, you know, going through the whole thing. And so it really prevented me from like, for example, what there was a growth tactic that could have existed where I was quite public building and public and doing a better job sharing the journey for several different reasons. And I didn't do any of that. I think there's probably a way that I can and should be doing that going forward. I think I could be good at it. So yeah, I guess it's another thing that comes to mind. But yeah, a lot of it is. I mean, I guess one other thing, but it's a flavor of bootstrapping, is I'm going to build a product that like generates revenue from day one. I'm not going to build something that I can't see a business model for, for several years. Yeah, I guess that's what comes to mind.

Callan Harrington  46:31

Can I ask what are you doing from like an emotional perspective to go into this other one, those daily habits, whatever that may be? What are some of those things that have had the biggest impact?

Taylor Crane  46:39

I definitely don't want to make it seem like I figured it all out yet. It's definitely a journey. But, so I started therapy, for example, during the Club's journey. I think that's been super helpful. I also had an executive coach at the time, as well. And so I'm really heavily prioritizing my physical fitness, which I think lends itself quite well to mental fitness as well. And so I'm working out every day, I'm doing yoga several times a week, I'm using an app, it's a mental fitness app as well, that it's called Mindy. And it's like daily exercise, mental fitness exercises that you sort of like wake up in the morning, and each day it kind of prepares you for the day and like, sets you off on the right tone. I think that's been quite helpful as well. Honestly, though, like, I think a lot of it is just lived experience. And just now I've seen the highs and lows of Clubs, I saw where it ended. It turns out, the world isn't over, now that the Club's journey is done. You know, I'm still here. I'm, frankly, I think I'm doing better than ever. I think that alone is like a really good lesson to internalize and remind myself of from my own experience now, that this isn't life or death at the end of the day. And a first-time founder, I think sometimes you can feel it is, because you don't know what it's like for it to- like you don't know what failure is like at that scale. And now you do.

Callan Harrington  47:54

Such good advice. I think all of it is excellent advice. Last question I have for you is, if you could have a conversation with your younger self, what would that conversation be? What advice would you give them? Age totally up to you. This could be two months ago younger self.

Taylor Crane  48:09

I think, well, one thing that comes to mind is like, if I told my poker player self that I was the CEO of Clubs Poker, building the next great, you know, online poker app, it would have been the coolest thing in the world. It would have made me so happy. And I don't even know what the lesson of that is or where I was going with that. But that's something I would have wished I could just- that I wish I could say. I think a theme throughout my career has been feeling a deep sense of anxiety that I'm not as far along as I want to be, or that I'm not at the point that I want to be. I always think I should be further ahead, and trying to articulate like the feeling like you're never gonna get there. There was a time where I wanted to be a PM, I wasn't a PM at the time, and I was like, how do I- I am never going to get here. Like, I wanted to be a founder. I was like, there were years where I was like, hey, I don't know how to start a company. I don't know how it's going to happen. And that produced like a lot of anxiety for me. It still does to an extent, honestly. But the thing that I've learned this whole time is like, if you just keep taking the baby steps, and putting in the work, and not losing focus, and really it is about these like baby steps and you're constantly just like, incrementally building on top of what was yesterday. You know, I've done the things I've wanted to get to. They aren't always, you know, in the exact timing that I've you know, would want or hope for. But I'm really proud of how I've stuck with my ambitions over the last number of years and gotten to where I am today. And so I guess to round it out, and to bring it back to your initial question, I would tell my my earlier self to like, practice more patience. It's going to come, you know, relax, it's going to come, just keep putting in the work, keep putting your head down. And although I did that, I've done that over the last number of years with a lot of like deep anxiety. And so hopefully, it might help like reduce the anxiety a bit. It's a tough question, though.

Callan Harrington  49:56

I mean, what I'm hearing you say is, it's almost kind of like, and I I certainly had this, I had a timeline on where I was supposed to be largely driven out of comparing myself to others, and where they are, and feeling like it's just so out of reach. Like, I just don't have the skill set to get there. And then in the next year or two, you're right where you are hoping that you were going to be is, but leading up to that had a ton of pressure, put a ton of pressure on myself to get there. And I don't think that that was necessary. I don't think dialing up that much on myself was necessary, and I would have got there regardless, as long as I was continuing to learn, grow, develop.

Taylor Crane  50:33

Exactly correct.

Callan Harrington  50:34

Yeah. I think that's excellent advice, and it's definitely something that I'm personally still actively working on. Really, I think the thing that you said is like, how can you just be better than where you were yesterday. And eventually, you're gonna get to where you want to go, as long as you're continuing to do that. So, Taylor, this is great. I really, really enjoyed this conversation. Obviously, looking at the clock, we went way over time, which I was totally cool with, because the conversation was so good. Thanks for coming on today.

Taylor Crane  51:01

Thank you so much. Yeah, this was enjoyable. And it's been fun to reflect on the last few years from like, now that it's all over. So this was enjoyable for me too.

Callan Harrington  51:09

I love it. This is excellent.  I hope you enjoyed Taylor and I's conversation. I loved how honest Taylor was throughout the entire episode. If you want to learn more about Taylor, you could find him on LinkedIn in the show notes. Also, if you liked this episode, you can find me on LinkedIn to let me know. Thanks for listening, everybody, and I'll see you next week.