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Today we welcome Dimitar Stanimirov, a seasoned SaaS founder, operator and investor.
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He co-founded WePal, which was acquired, and Heresy, and helped scale Stack Overflow, Handshake, and Crossbeam to over 100 million ARR.
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As an angel investor in B2B SAS, he's backed pitch.io, Lightdash, and others from Pre-C to Series A.
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So it feels like founders are really obsessed by Exit.
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It's something that we talk about a lot.
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There's kind of a whole mythology around it.
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You've seen a through, you've been through a few.
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What would be your sort of main takeaway from Exit?
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Okay, so as you probably picked up uh while reading uh my brief bio, I have been, in hindsight, lucky to experience both a positive exit um and what you might call not so positive if that makes sense.
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Um so what I mean by this is you know you can sell your company, um, you can IPO.
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I've not been uh lucky enough to do that yet.
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Um you can um sell um to your existing team or investors, uh, or you can just end up shutting down your business.
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So depending on which one of those options you go through, I think what you take away is going to vary significantly.
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Um, and as you know, I've been in high side, I say, lucky to have experienced a bit of both.
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So like somewhat of successful outcome in a company I co-founded, and another one which we ended up shutting down after three and a half years of running it because we felt like it wasn't growing the way we wanted to, and sometimes that's the harsh reality of uh startup life.
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And I think as we talked about before separately, like so the journey to success sort of isn't necessarily the first company you're in, it can be like sort of successes over a period of time, you could go through many companies.
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Yeah, but if we look today at kind of exit from a positive way in terms of it's giving you some form of financial return, yeah, that kind of involves a few decisions around sort of am I ready to sell?
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Is this a person to sell to?
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What do I do after it?
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I think it'd be quite interesting to explore that.
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Yeah.
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Full disclaimer, my biggest financial outcome, if you will, from from an exit has been uh from a company I have uh worked for rather than co-founding my own.
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But getting into the position to be part of uh the exec team and and and you know, even land that job in the first place came on the back of building a business before that.
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So there's a story there as well if you want to go down that route.
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Um, but again, it wasn't my my company uh that gave me the biggest financial return, if you will.
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Yeah.
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Which which is quite interesting to take away from itself.
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Yeah.
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But if we go so you're the first company then, the one that you sort of exited that you had started.
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Perhaps you give a bit of sort of context around that, and then sort of how how you get to the point where you thought exit might be the right option.
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Yeah.
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Um, well, the short answer is I I I just got very lucky to have a co-founder who um I just did not get on with.
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Um and it's only a matter of time before you you part ways.
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Just for the record, as well, you know, we we did have um a handful of co-founders, it wasn't just the two of us.
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That probably would have been much easier.
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Um, it was a whooping five, uh, which is not something you come across often, and that presents its own challenges.
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But there was one particular co-founder who, dare I say, was somewhat toxic, and and working with that individual was just not fun.
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Uh, and so, and you know how long you tend to to grind when you're building an early stage company, um, so you're spending literally every single day, and you know, sometimes late into the night with that person, and that's just not what you want to be doing.
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So, um, from that standpoint, it was a fairly easy decision on one side, but on the other, because you have invested so much into getting to where you know you got to it's difficult to walk away.
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And we have had this conversation in uh a previous episode.
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Yeah, um, so that was that was challenging.
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Because it feels like there's a there's a big sunk cost there.
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It's kind of like you put a lot of almost the more you've sucked up to make it work, yeah, the more you feel I've sucked up so much.
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Can I not take a bit more?
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And in this particular example, so this is my um um first company.
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Uh it was called Ovia at the time.
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Um it's uh rebranded a bunch of times.
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The last name of the company was called Weep Out.
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We got acquired by Outmuch.
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OVIA was actually um a pivot, if you will, of a
Load full transcript
previous business um that we worked very hard on trying to stand up.
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That didn't work.
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In part of the technology, uh, we ended up repurposing and standing something up that actually did take off.
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And so having had this kind of initial setback, I think, makes even more invested in the success and makes walking away harder.
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Because that for so yeah, so you you do a business, doesn't quite work, you get pieces and you've suddenly got that traction and it's working really well.
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What is going through your mind at that stage where you've kind of got sort of business trajectory of sort of ever increasing and just kind of almost the same time ever increasing personal costs or lack of enjoyment?
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Yeah, yeah.
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I think the the lack of enjoyment, unfortunately, you can endure for longer than you probably should.
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Um there's uh you know a bill that eventually have to pay for for that, but as I said, you do endure it for for longer than than healthy.
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Um I think in my personal case, um we got um again in hindsight very lucky um because we ended up raising money in the US.
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So we did 500 startups and then we raised in the US.
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Um, and this is 2011, so 2010-2011.
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And um, you know, during those days, if you raised in the US, you had to physically be in the US.
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I think this is actually coming back again, but obviously there was a big window where you could raise from um US um venture funds uh and be running your business from from anywhere.
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That was not the case uh when we were building OVIA, and so um we basically had to to relocate.
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And then you have you're confronted with two two kind of difficult decisions.
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One is continuing to endure what is a pretty unpleasant um work environment, if you will, and the other one is doing that you know, miles away from home, leaving behind family, friends, um, and at the time girlfriend who ended up being my fiancee and my wife and mother of my children.
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So um, you know, in hindsight again, I keep on saying hindsight, but hindsight is 2020.
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It it ended up working really well, but purely, I think, um because of luck, I suppose, or the way the way things kind of panned out.
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But it feels like it's such a big commitment that you've made.
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I mean, I can just imagine that moment, like you've taken these huge steps in terms of you've gone again with the same founding team, you've stepped away from your own country, you've stepped away from your part, like you've taken all these steps to really commit to this idea, and at the same time, there's a sense of have I oh, there's this big cost that I'm paying.
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Yeah, um, I mean, the answer is you'd you would never know, right?
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Again, I'm looking back now, you know, what is this like, you know, it's 15 years, um, and I'm thinking, oh my god, this worked really well.
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Who knows?
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I could be, you know, could have been in a different universe, could have been sat here putting my hair out thinking, oh, you know.
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Um again, you know, so I didn't make like, you know, um uh anything meaningful from the transaction.
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So, you know, what ended up happening is myself and one of my other co-founders ended up being bought out um uh after the series A.
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And so at that point, the valuation is you know, it's not high by any means.
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Um, but that was pretty much my first proper job out of university as well.
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So it's you know it's meaningful for you at the time.
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Um, but then the company continued to operate for you know another eight years or so and eventually ended up being acquired.
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And if that you know acquisition was, I don't know, in the multi, you know, millions, billions, it was probably in the multi millions, but not you know, nowhere near billion, then probably I'll be sitting here pulling my hairs out thinking, oh my god, what have I done?
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But I don't think that was the case at all.
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Um and so But it's interesting that because let's say it had been a multi-million pound acquisition.
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I suppose the question is, even could you have sustained another eight years of that?
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And would if you had stayed there, would would that have been its trajectory?
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I don't know.
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The I I don't know.
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Um could I have endured it for you know another eight years?
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Maybe, who knows?
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But again, you know, things are so dynamic, you don't really think about this.
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At the time, I just knew that I was deeply unhappy, I had spent an awful lot of time building this, and I I just could not see myself continuing, especially if I had to relocate.
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Yeah.
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And so for me it was a pretty clear-cut decision.
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Uh, or at least I say that now.
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At the time I do remember kind of, you know, thinking, should I do it, should I not do it, should I do it, should I not do it?
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The one thing I I do know very clearly is that the second I actually said, you know, I'm leaving, I kind of felt like a burden was lifted off my shoulders.
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So it felt good, that's all I know.
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So how so how did you then make this decision?
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So it turns out a decision that lifted the weight.
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What was your process to get the decision?
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Was anyone involved in it?
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Was there anything that particularly gave you clear anything you recommend to other founders to to do in this in this circumstance?
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I got years later, ironically, I got really good advice from um Michael Pry, who is a storied entrepreneur, one of the co-founders of Trello, um, who I don't know, my kill his quote here, but it was something along the lines of making sure that you really enjoy the journey because the destination is never guaranteed, right?
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And so, you know, if there's any advice I could give is basically what Michael told me, make sure that you know the journey itself is is fun and enjoyable because you might never get to that outcome, right?
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And by the way, the journey is going to be brutal anyway, and so kind of fun is it's tricky, but make it as as much fun as possible, right?
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At least surround yourself with people that you like.
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Yeah, I'm I'm just wondering because so we have have another guest guest in the podcast called Freddie, and she her whole theme was like actually it should be fun.
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Yeah.
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And it feels like it's slightly indulgence, counterflux indulgence.
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Actually, fun leads to higher performance, more sustainability, greater creativity.
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Like it should not be a word we're we're scared of as well.
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Yeah, yeah, yeah, yeah.
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Totally.
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And you know, things will be fun, uh, but equally they will be very, very challenging.
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And I I again I would reiterate this: make sure you surround yourself with people that A, you respect and you really enjoy working with, but also you like hanging around with.
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Um But with any business, you're almost like making a series of like all-in decisions.
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It's kind of like you are making bigger and bigger commitment, and and it feels like there's almost a time at each stage to go.
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Actually, is this the right step for me?
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Do I want to go all in again?
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Like, yeah, yeah, yeah.
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Or is now the time to go,
no, I'm gonna take my chips off the table.
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Yeah.
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Even if there are not many chips or no chips, it's like let's go and play with some other people on a different table, because actually it's gonna be more fun and I might get better results from it.
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Yeah.
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Well, this is a good segue, probably, into the the other um company that I co-founded, which again, if you want to use the word exit loosely, I exited, but it was, you know, we we ended up shutting down the business, and that is a much harder decision, I think, um, to make.
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Um because again, as an entrepreneur, you're kind of wired to see the bright side of things in in many instances.
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Um, you have to stay positive, you have to motivate your team, you have to you know motivate yourself when you know the uh when when things are kind of tough and you don't necessarily want to do the things that you have to do.
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Um and it's much more difficult, I would say, to actually pull the plug then and walk away.
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Quitting on time feels like quitting too early.
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Um, and very often, you know, when you're kind of in in that kind of situation, you end up probably sticking around for a lot longer than you should.
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You really do only have a certain amount of time, don't you, as a as a as a founder, and every year spent on one thing is a year and you're not spent on something else.
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Yeah.
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I've written uh about this with a slightly different analogy, um, which is thinking of um you know thinking of your time as uh a stack of chips that you have on a poker table.
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Um and the idea is that if you keep on playing every single hand that you're dealt, no matter how good or bad it is, good is good, but if if it's a bad hand, you should not keep on raising and committing, you should fold and wait for a better hand to be dealt.
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Um this is very much the same example, you know.
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If you're in a situation where you've been bet dealt a bad hand for whatever reason, you know, maybe things look great when you started, but for whatever reason the market turned, it didn't work out, team members left, you know, pick your reason.
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Um the most sensible thing you can do is to essentially quit whatever you do and and start something else.
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You know, it could be in the form of a pivot like we did in the first business.
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Um it could be completely shutting down and pursuing something else, um, but kind of sticking around, I think, is probably the one thing that if I had to do it all over again, I would not do.
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I would be more brutal and honest with myself and probably I say that now, but try to quit earlier.
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Um it's really interesting because things I did a business, I think probably around time we're actually going, going bike.
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And around year three of that, we did it for four years before we shut it.
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Like I think we'd probably in retrospect go, this is not this is not gonna work.
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Like we'd done some like we'd won some rewards and we'd got like some partnerships and looking like superficially looked really good.
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Yeah.
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But commercially it just was not working.
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There were just some market things, and it still wouldn't work today.
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The crazy thing is around that time I did a startup weekend where you kind of launch, sort of do like sort of old school, starting weekend yeah.
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Awesome.
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But like actually met this team of like uh there was we had a front-end developer, a back-end developer, uh, someone was really good at marketing, but like actually as as a as a as a team had all the skills to it.
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And we came up with this concept called Event Lick, uh, which was like pre-test events through pre-validate events.
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Actually, really cool idea.
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Subsequently, model was used elsewhere.
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And so actually on paper, that was a really great business to launch.
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Right.
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And we came up with a really cool concept during the thing, and it got really good feedback from people on it, but because I was committed to my other business, didn't pursue.
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We actually got we got approached about funding to go on a startup accelerator.
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So that was going like all the signals you'd want from scratch to go, this is actually a really good thing, really good team, good idea, funding, etc.
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Didn't pursue it because was was committed to a business that we probably should have stepped away from, which I think is a real I mean good lesson there.
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But yeah, but like there is a cost, isn't there?
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I mean the point is that that is actually it's not even like a theoretical cost, that is actually a very tangible cost.
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Yeah, so I really like the stack thing because my chips are on something else.
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Yeah, they could well have been on something different.
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Yeah.
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Um talking of Stack, I think um, you know, Stack, I think, has had actually a pretty big part in shaping my entrepreneurial journey, the way I think, um, the way I act as an operator.
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And so um this is another quote from um Joel Sparski, who was one of the founders of Stack Overflow, um, who I was very lucky to have um as a personal mentor when we were building Harris in my second company.
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Um, and he was the one person who very early on told me after you know discussing metrics and and how we were progressing that this is probably not worth pursuing.
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And this was probably like, I don't know, a few months after after launching um uh officially.
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And I at the time felt, whoa, this is way too early.
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Um but he was so persistent in saying, no, no, no, this is this is not gonna work, this is not gonna work, and it's not what he wanted to hear when he first launched, but he was right.
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Uh, and and the brilliant thing he kept on telling me is that you know he said, Look, I've been around startups uh a long time, and the biggest mistake, a lot of my friends who are incredibly bright people, you know, who have worked for Google for many years, some of the biggest tech companies, they're all very smart, but the one big mistake that they make is to confuse perseverance and grid uh with just investing in in bad ideas.
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And you know, you would need the perseverance, you would need the grid, but it has to be on the right idea.
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And if you're not on you know one of these kind of upward, up into the right journeys, you should probably walk away.
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So that's that's that's a good one to think about.
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The really triggered for me is a sense often when you work with founders who are new managers, there's a sense of I can make anyone work within their team.
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It's kind of like I can so people persevere with the wrong people in their team as well for too long.
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But actually, and they think it's they're doing it because they're supporting people or they're but often it comes down to ego, it's like not wanting to admit they're not good managers or they can't make anyone work.
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Yeah, and I just feel there's a correlation between this, this idea of like committing committing to the wrong thing for too long, probably because of ego.
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We tell ourselves for good reasons, yeah, perseverance, grit, yeah, yeah, sort of support of people, but ultimately a lot of it comes down to ego and not look thinking we can't do it or we've made a mistake.
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Yeah.
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With with um with startups, I think it's even harder because you know, this being a founder, um, it's a big part of your identity.
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So
shutting down the business, you know, I kind of feel like it's almost like chopping off a limb.
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Um very extreme and graphic, but you know, it's that kind of thing where you know killing the business is kind of foregoing a big part of yourself, which is very, very difficult.
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With the hiring example, I totally agree with you.
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I think it's easier from uh you know just wearing my operator hat.
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If you inherit a big team, I think it's a lot easier to make that call than if you have hired someone.
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Then I think it becomes a little bit trickier, you know, because you do you kind of feel like you owe people who you have um brought on board, you you have the moral duty to make them successful.
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But sometimes, and often look, it could be that you know you made a bad hiring decision, uh, and to your point you should basically come to terms with it and proceed accordingly.
00:18:27.920 --> 00:18:30.640
But I think often it's like, no, I can make it work.
00:18:30.799 --> 00:18:37.200
Um but I think that one is it's easier compared to deciding to walk away from a business.
00:18:37.519 --> 00:18:37.839
100%.
00:18:38.079 --> 00:18:38.720
I think that's right.
00:18:38.880 --> 00:18:41.519
People find that difficult, the sort of the higher bit difficult.
00:18:41.680 --> 00:18:46.079
So like walking away from a business is even even the language of that, cutting off a limb.
00:18:46.160 --> 00:18:50.240
Yeah, people are like, no, but people think, oh, it's like my business is my baby.
00:18:50.400 --> 00:18:50.640
Yeah.
00:18:50.799 --> 00:18:52.000
I mean you're using that language.
00:18:52.079 --> 00:18:53.680
How can you possibly shut a business down?
00:18:53.839 --> 00:18:57.039
Because you are you are cutting away even more graphically than a thing.
00:18:57.119 --> 00:19:03.839
So I think the language people use and the stories they tell really impact their ability to make sure my team is my family.
00:19:04.000 --> 00:19:04.160
Yeah.
00:19:04.319 --> 00:19:07.039
Well, you've got you're not gonna you can't let your sister go.
00:19:07.279 --> 00:19:12.799
I mean, this is you know, talking of which this is probably the hardest um thing, you know.
00:19:13.039 --> 00:19:19.680
When we um decided to um start winding down her that was probably the hardest thing to do.
00:19:19.920 --> 00:19:28.079
Um having to let go people that you convinced to join your team who were happily employed elsewhere, and they kind of gave you the vote of confidence.
00:19:28.400 --> 00:19:33.519
You, the rest of the team, um other co-founders, um, the idea.
00:19:33.599 --> 00:19:35.119
So that is probably the hardest thing.
00:19:35.200 --> 00:19:51.359
That and also letting down customers who are paying and rely on your service, and you say, look, you know, we've decided to start to shut down the business, and you know, you've got three months to find another another provider because um you know we're going to completely pull the plug on this um come April, you know.
00:19:51.519 --> 00:19:55.759
So those are really, really tough decisions and and you know hard conversations.
00:19:56.319 --> 00:20:03.039
But interestingly, if you flip it the other way around, I think these things feel really hard and they are hard, and they do and they are hard.
00:20:03.440 --> 00:20:07.680
But your team will leave if better opportunities come up often.
00:20:08.000 --> 00:20:14.000
Your clients will leave if you're if your service is saying, and they won't give you an extended notice period on on your contract.
00:20:14.160 --> 00:20:20.240
So I sometimes feel we feel this guilt and this obligation, which can be quite one way.
00:20:20.559 --> 00:20:30.640
Firstly, yes, at some point it will happen, but I think when that happens naturally, it shows that this individual has outgrown the team they're in, the company they're in, that there's no more opportunity for them, right?
00:20:30.880 --> 00:20:31.839
And it's not a bad thing.
00:20:31.920 --> 00:20:33.519
I think we should be celebrating this, right?
00:20:34.000 --> 00:20:48.160
Um if they leave prematurely, at least, you know, in your kind of um understanding of what that means, or mine, it will be due to you kind of failing them, I think, one way or another, right?
00:20:48.240 --> 00:20:53.839
You're not providing that way for them to grow further, they're deeply unhappy for whatever reason, and you missed it, right?
00:20:54.079 --> 00:21:04.720
So I kind of feel like, you know, yes, it can happen, but you know, it's on you when it happens, and if it happens when they have outgrown the business, then everyone is, I think, in a in a better place.
00:21:04.880 --> 00:21:07.359
And you shouldn't be forcing people to stay.
00:21:07.519 --> 00:21:15.839
So I left Stack Overflow, you know, after you know, almost five years there, and I left to pursue um, you know, uh another business idea, felt very passionate about.
00:21:15.920 --> 00:21:20.000
I didn't feel any less passionate about what Stack Overflow were doing at the time.
00:21:20.079 --> 00:21:21.440
I deeply believed in it.
00:21:21.599 --> 00:21:27.599
Um, in fact, I was probably the biggest cheerleader for the business um you know from the sidelines.
00:21:28.559 --> 00:21:36.799
But I kind of felt like I had done my piece, I have built a strong enough business would which I felt would endure without me there, which it certainly did.
00:21:36.960 --> 00:21:41.119
Uh and I just wanted to go and explore other things that I felt would make me happier.
00:21:41.279 --> 00:21:44.160
So that's been quite a consistent trend for you, isn't it?
00:21:47.680 --> 00:21:48.079
Yeah.
00:21:48.559 --> 00:21:54.400
Which and it showed also like your success, as you said, like your biggest success financial success was not actually your own, but it's
someone else's.
00:21:54.480 --> 00:21:54.640
Yeah.
00:21:54.799 --> 00:22:04.160
So it shows that that ability to suppose A operate in different environments, but B the That your high quality team members can be super valuable.
00:22:04.319 --> 00:22:04.880
Yeah.
00:22:06.000 --> 00:22:10.559
Now that you've experienced both, what would you what might your next thing be?
00:22:10.640 --> 00:22:15.920
Like if you're talking to other founders, would you recommend them try working for other people?
00:22:16.160 --> 00:22:18.640
Do you feel that's given you something different?
00:22:19.519 --> 00:22:23.279
For me, certainly it has, but one thing I do know is that it's not for everyone, right?
00:22:23.440 --> 00:22:27.359
I think founders are kind of you know strange animals, right?
00:22:27.519 --> 00:22:41.519
You know, you've got you've got people who are absolutely dead set on working for themselves and themselves only, and they uh you know self-aware enough and they say, look, I can just not be managed, I have to be in charge, and this is who who I am.
00:22:41.599 --> 00:22:42.960
There's nothing wrong with that.
00:22:43.119 --> 00:22:49.200
Um, I know a handful of founders who fit that description, um, and I'm great friends with them.
00:22:49.279 --> 00:22:53.839
Wouldn't I like to be on the same team with them if we are peers and working together under someone else?
00:22:54.000 --> 00:22:54.559
Probably not.
00:22:54.720 --> 00:22:58.480
And I don't think, and they were the first one to raise their hand and say that is the case, right?
00:22:58.720 --> 00:23:04.799
So if a you know, if if you're like that, then it's probably not a good idea to go and work for for someone else.
00:23:04.960 --> 00:23:15.519
Um, because I don't think that will make you happy, I don't think it will make you productive, and I don't think it will be um a good rel you know, good relationship with whoever you know whoever company you end up joining.
00:23:15.599 --> 00:23:16.720
Do you see what I mean?
00:23:16.880 --> 00:23:19.599
Yeah, um I approached it differently.
00:23:19.680 --> 00:23:25.599
You know, I never had an issue necessarily with uh authority or you know, being my own boss, that kind of stuff.
00:23:25.680 --> 00:23:30.240
For me, it's always been about um working on something that I believe in, right?
00:23:30.400 --> 00:23:37.680
And often it could be something that you're very passionate about, and for whatever reason it doesn't exist, and you decide that you're going to go and create it.
00:23:37.839 --> 00:23:51.119
Um, but equally the businesses that I have been lucky to work for, I have deeply believed in, I've said, Oh, I you know, I really like this idea, it's not my idea, but I would embrace it very much like my own, and I'll give them my own to make it make it happen.
00:23:51.279 --> 00:23:54.640
And so if you're like that, I think then absolutely go and do that.
00:23:54.799 --> 00:24:13.440
But if you're more in the former camp, which is look, you know, I have to run the ship here, I think you'll be probably way more happy and more productive, and you would have better outcomes if you pursue your own individual path and you know, stay co-founder CEO or just running your own thing.
00:24:13.759 --> 00:24:30.720
Do you feel that you're unusually pragmatic for a founder then in terms of this ability to sort of take a step back and make these kind of sensible decision of vertical commons like time to exit, kind of let's say with your second, but like you had money on the table to like go again with that?
00:24:31.119 --> 00:24:32.960
It wasn't like you didn't have the option to continue.
00:24:34.160 --> 00:24:43.519
How how do you feel you are able to take the step back and make these more emotionless decisions in quite sort of emotionally charged times?
00:24:43.920 --> 00:24:44.799
I don't know.
00:24:45.119 --> 00:24:46.400
I wish I'd I don't know.
00:24:46.480 --> 00:24:48.319
I I wouldn't say I'm like super pragmatic.
00:24:48.400 --> 00:24:57.039
I think you know, I I'm just like everyone else, you know, a lot of these decisions are driven by emotions, and it's even more true when you're in it.
00:24:57.279 --> 00:25:10.000
Again, I can I can talk about it theoretically now, um, now that I'm kind of removed away from the situation and you know the ones have somewhat healed, but it's never an easy decision, right?
00:25:10.240 --> 00:25:22.400
Um, and again, with the the example I gave you with heresy, where we run the company for three and a half years, I think the writing was on the wall, and you can start feeling it probably two years in, right?
00:25:22.559 --> 00:25:24.559
Maybe two and a half years in.
00:25:24.799 --> 00:25:31.119
Um and I think I mentioned um this last time we we spoke.
00:25:31.279 --> 00:25:40.640
Um, what made it somewhat easier, I think, to realise is again, uh I had just come out of of Stack Overflow, which was growing like mad.
00:25:41.200 --> 00:25:47.759
Uh and so I had been very fortunate to see what this sort of proverbial hockey stick growth looks like, right?
00:25:47.920 --> 00:25:49.519
And everyone is chasing that.
00:25:49.759 --> 00:25:55.519
Um and so one year, two years in, you're not seeing it.
00:25:55.759 --> 00:26:02.400
Um you might decide to stick around and look in their companies, like um I can't really think of a good example here.
00:26:02.480 --> 00:26:11.119
But Figma Figma is a great example where it took them actually a long time to um to kind of go up and to the right, and once they did, boy, you know, um watch them grow.
00:26:11.279 --> 00:26:21.119
Um and that could happen, but again, um I kind of felt like we were we were missing the mark there and going back to the um Chips, the chip uh analogy.
00:26:21.680 --> 00:26:24.880
Um kind of you know, that's that's kind of in the back of my head.
00:26:24.960 --> 00:26:33.200
And then I've got Joel, you know, kind of saying, mm-mm, you know, it's been it's been
six months, it's been a year, I'm like, oh shit, you know, it's clock sticking.
00:26:33.359 --> 00:26:38.160
The other thing which I mentioned when we last spoke is that my uh personal life changed a lot.
00:26:38.319 --> 00:26:43.359
So my risk appetite uh you might say decreased significantly.
00:26:43.519 --> 00:26:50.400
Um we started when we started hearing was me and my co-founder, uh, and it was me and my wife uh in my personal life.
00:26:50.480 --> 00:26:53.519
And by the time we shut down the company, I had two kids under two.
00:26:53.599 --> 00:26:57.839
Um, you're a father, yeah, you know, you know what that kind of can do to your life.
00:26:58.000 --> 00:27:10.319
Um, and so when you have that as well on you know, in the balance, it just makes the other piece a lot more easier to kind of hit home and be like, okay, this is just not working, and and and move on.
00:27:11.279 --> 00:27:23.119
So almost if we say there's a finite amount of chips that you've got to play with, it feels like suddenly when you have these other dependents or something, the value of the game suddenly spikes as well.
00:27:23.359 --> 00:27:24.000
Yeah, yeah, yeah.
00:27:24.079 --> 00:27:28.480
Yeah, the the buying is essentially uh you know jump like tenfold.
00:27:28.720 --> 00:27:29.599
Yeah, yeah.
00:27:29.920 --> 00:27:32.960
Well, this made me thinking, A, is that I'm still really bad at poker.
00:27:33.119 --> 00:27:38.079
Like I I really I really can't resist the concept of buying like not playing, yeah.
00:27:38.240 --> 00:27:41.359
Um which why I'm really bad at it.
00:27:41.519 --> 00:27:50.960
But I I do think it's a nice analogy though, because it's kind of like that there's so many elements you can't control, but you do only have a certain amount, you start with a certain amount of chips.
00:27:51.200 --> 00:27:51.680
Yeah.
00:27:51.920 --> 00:27:53.200
You can win more, yeah.
00:27:53.440 --> 00:27:58.000
Not enough time, but I suppose money can buy you more time and more resources and more opportunities.
00:27:58.400 --> 00:28:10.319
I think in in poker, and I'm I'm you know, I'm I'm not a good poker player by any means um decent, I'd like to think, but you know, um I think it's way more about the hands that you choose not to play versus the ones you play, right?
00:28:10.559 --> 00:28:19.839
Um and again, if you're throwing chips at every single hand you're dealt with, that's a a guaranteed way to um to be off the table within a very short period of time.
00:28:20.079 --> 00:28:24.079
But it sounds like also going in with a sense of what does working look like?
00:28:24.240 --> 00:28:24.319
Yeah.
00:28:24.559 --> 00:28:34.400
Because it feels like the Stack Overflow experience in your mentor gave you a very clear sort of paradigm for this is this is a two-king starting point hand, you should play this.
00:28:34.480 --> 00:28:34.960
Yeah.
00:28:35.440 --> 00:28:37.279
If there's another king, this you can continue.
00:28:37.599 --> 00:28:41.839
If you're still sitting on a king of two and a three after three cards, yeah.
00:28:42.640 --> 00:28:43.680
Maybe think about folding.
00:28:43.839 --> 00:28:47.519
We definitely put like a four on the tape at that stage, time time to go.
00:28:47.680 --> 00:28:48.000
Yeah.
00:28:48.400 --> 00:28:51.839
You talked about that that profile of growth.
00:28:52.000 --> 00:29:02.000
Is there anything else that you think after three years, two years, you haven't seen it's time to maybe fold and not not play the hand?
00:29:02.319 --> 00:29:09.039
I mean the the the growth is essentially um uh sort of the tip of the iceberg, if you will.
00:29:09.200 --> 00:29:13.519
There's a lot more things that kind of go underneath to you to produce that that growth, right?
00:29:13.680 --> 00:29:21.519
So um, but if you were to pick the one thing that would be the the telltale sign, I would I would say is that, uh at least at least for me.
00:29:21.680 --> 00:29:34.160
And again, look, um we could raise uh venture funding, so we raised you know a million dollars um for for heresy uh on the back of a deck.
00:29:34.319 --> 00:29:44.079
Um and so there's big expectations riding on you, and you know, with every single um milestone that you hit, um people kind of cheering and celebrating.
00:29:44.240 --> 00:29:48.799
But at some point the milestones, at least for me, felt like they plateaued, right?
00:29:49.119 --> 00:29:51.039
Um and they weren't so meaningful, right?
00:29:51.119 --> 00:30:09.920
So and maybe you can, you know, I'm kind of looking back, maybe we could have raised more money earlier on, maybe we got greedy and we felt like, oh, you know, one million is enough to basically get us uh from deck to idea customers and then to um over you know a certain threshold of uh annual recovering revenue.
00:30:10.160 --> 00:30:10.880
I don't know.
00:30:10.960 --> 00:30:22.240
Um but the one thing I do know is that that you know it felt like everything kind of started plateauing, uh, and the joy of actually building and pursuing that idea just disappeared.
00:30:22.480 --> 00:30:32.720
Um and again, you raise venture money, you're chasing venture returns, both for yourself and for your investors, and you have you know investors, and you have to be you have to be honest with yourself.
00:30:32.880 --> 00:30:46.000
Um, I think, and you know, and this is I think the best thing for investors as well, ironically, but I think sometimes when you're again so committed, you know, you're pushing the startups because it's a sankos, right?
00:30:46.079 --> 00:30:48.160
You're like, oh, you have to keep going, you have to keep going.
00:30:48.319 --> 00:30:56.640
Um, and the truth is, you know, not necessarily, you know, I'd rather preserve uh and I can speak this, you know, I can I can say this as a as an investor as well.
00:30:56.720 --> 00:31:06.079
You know, I've had like a bunch of startups, just one this week, by the way, who emailed and said, look, you know, we've pursued this for um you know three years as well, it's not working.
00:31:06.160 --> 00:31:08.000
We actually tried to raise as well.
00:31:08.160 --> 00:31:13.920
Uh we spoke to you know uh 50, 60 VCs, no one is willing to write us a check.
00:31:14.079 --> 00:31:16.960
We're folding, uh, you know, folding the business.
00:31:17.119 --> 00:31:18.480
That's the right thing to do.
00:31:18.640 --> 00:31:30.880
Um I've had other companies um who could folded way earlier, um, purely because they felt like they were not um hitting the milestones that they they wanted to hit, and they said, look, you know, have the money back.
00:31:31.039 --> 00:31:33.440
We you know, we're gonna go and do something else.
00:31:33.680 --> 00:31:36.319
Um I think that's perfectly normal.
00:31:36.640 --> 00:31:52.319
So I think I'm I mean it's been really good, but I think what I've taken from this is the sense of exit can be positive or negative, but that can also just be of the moment, like a negative exit can also lead to positive stuff, like you've only got so many chips, yeah, don't waste them on the wrong hand.
00:31:52.559 --> 00:32:11.519
And actually, what if the hand's not only bringing you that sort of growth curve, yeah, but there's also like a feeling to it as well, like if it's not bringing you joy, if you're not enjoying the people on the journey with, yeah, maybe this is maybe this is not the hand, this is not the game, and that's and that's okay because there are gonna be lots of other like there will be other opportunities.
00:32:11.680 --> 00:32:26.480
Yeah, if you take this as your guiding principles, if you will, I think it would make it a lot more easier to walk away from you know these proverbial bad hands that kind of clenching on because you expect that there will be a you know financial incentive you know further down the line.
00:32:26.559 --> 00:32:41.440
And I've seen this so many times, and this is you know, both with founders but also with employees and kind of um you know managers in in kind of big tech companies um that are you know private.
00:32:42.559 --> 00:32:56.000
So many people I think kind of have wasted I don't see that I don't say it lightly by the way, but I know personal friends of mine who have wasted, I feel like, so much time kind of holding on, waiting for an IPO when this IPO is never gonna happen, right?
00:32:56.400 --> 00:33:01.599
Um, but you're wearing your rose tinted glasses and you're like, no, it will happen, the market just needs to turn.
00:33:01.680 --> 00:33:09.920
And in the meantime, again, you could have started your own business, you could have joined another company which is actually on on path to IPOing.
00:33:10.079 --> 00:33:21.440
And so, you know, it's if we keep on circling back and coming to the chips, you know, don't waste the chips on bad hands, is you know, the one single thing that you know, if you were to take anything out of this conversation, I would say is that.