238: Brian Sierakowski — Leading an Acquired Business

storms, dealing with the tanking economy, there was a lot going on. Today, you'll hear a rare perspective from the other side of indie hacking, how acquired businesses are ran, keep running and what you can do to make that easy and make your own business more sellable in the process, and just how judgmental the founder community can be. A quick thank you to our sponsor here at this point, acquire.com. More on that later. And now here's Brian. Enjoy!

Brian, you took over as the CEO of Baremetrics after Josh Pigford sold the business in 2020, I guess. You ran the business, you made several significant changes. And I guess we'll talk about a couple of those too. And now you've left your position as CEO a few weeks ago and that's quite the journey. Can you give a quick introduction into what Baremetrics is, how you found your way into that company and what you've been doing there until just a few weeks ago?

customers and what they're doing. I came to Baremetrics, by way of actually, I'll have to back up a little bit. So many or a couple of companies prior, I founded a company called TeamPassword, which was a password manager for teams. I'm not exactly a branding genius, but I got the job done. And I ran that nights and weekends for about two years, then I went, they kind of grew to having enough customers that I could go full time on it. I did that for about five years. And I'm

happy to we can kind of reverse and talk about this more. But kind of the short story there is like, I thought that running it part time, it was growing at a certain speed. I assumed that going full time on it was going to grow at that speed times like probably times a million was my, you know, subconscious expectation. But it didn't. That wasn't the case. I think it grew a little bit faster. But really like everything that I tried to do to grow the business didn't really work.

It just kind of slowly grew over time. And if you zoomed out on my chart, my MRR chart, you wouldn't have really been able to tell what I was doing at all. So I made the decision to sell the business. I decided that and I don't remember what year it was. We can go back and add years. But you know, I was like basically like January 1, I was like, alright, I'm going to sell the business. I did that until February 28th. I had sold the business. So I actually went through a lightning fast

sales process, DD, everything finding the buyer, which that was actually crazy. At the time, I didn't think it was because I was inexperienced. And I didn't know how long this stuff takes. And so I'm like, okay, cool, pretty normal stuff. I worked at that acquiring company, the business at the time was called Jungle Disk. They're now called Cyber Fortress. I worked there for two years as their director of products. I went from running just my business to running portfolio of products

and about five different products. They sold my company, TeamPassword to a private equity firm called Xenon, about six to nine months before I joined them. So I kind of got introduced to the team there. And then I was chatting with them and like, hey, we're buying this other business. I didn't actually know what business it was, like we're buying a business, we think you'll be great for it. And a time I was like, sure. Great. I probably should have asked more questions.

But my goal going into that was, you know, I had the experience running my own business, then I had the experience running a portfolio of products. And then it was like, okay, cool. Well, I want to sort of see what it's like with multiple companies growing and that kind of, I'd always kind of heard of the private equity playbook. That was something that was very interesting and mysterious and appealing to me. And I want to just get like a higher velocity experience of like, what

is it like to grow a business that's larger? What is it to? I was at a director position at the other company, what would it be like to be in charge? And that was kind of the thing that was promised to me as I joined the business. They were like, yeah, you're going to learn a lot. And at that point of time what I thought learning a lot was going to look like was like somebody sitting me down and walking me through like here's how you solve this problem, here's how you solve this

problem. And in reality, it was more like, alright, we're gonna put just a huge number of intractable problems in front of you and you're just gonna have to like barrel through them, you know, headfirst and so. So yeah, I learned a lot. So that's kind of the quick arc from founding my own business all the way through to at least joining Baremetrics.

through the portfolio. And then going to the other side, this is something that I think most people who are building software businesses or generally indie businesses, they don't have experience in at all. Like they come mostly from a technical background, not from managerial background. And even if they come from that background, they don't have like the kind of overarching director of product experience. So it's really nice to hear from you here today about all of these

things. And I'm just going to ask you a couple of questions about the journey with Baremetrics, I guess and then you know, where it ended and where it's going to go in the future. But we'll get to that later, you know, historically correct. We're gonna go chronologically here, I guess. I think it's just super exciting to think because I cannot imagine what it is like to come into a company that was just

acquired to replace the original founder. How did that feel? Honestly, this is, I know, this is a wishy washy kind of question, but I wanna know because entrepreneurship, to most of us, is such a dear to our heart kind of thing. How did it feel to come into a business that somebody else has built?

know, there was kind of like, there's always pressure, right? Like, if you start your own business or even just like, if you're, I was gonna say working a regular job and that sounds derogatory. You know, if you're just like working at a tech company or whatever. If you're like a mechanic, there's always some aspect of like, hey, you have to like you gotta fix the cars good. Like, that's the pressure that's on you. So, but it felt like in this case, the pressure was heightened

from multiple different angles. So one, yeah, it's like, you kind of fill in big shoes, you know. And also, the person whose shoes you're filling is an active member of the community. So in some way, it's like, you know, like dating somebody's ex, you know, that's still in your friend group. It's like, okay, like, you know, I have a duty to myself and to the team, to the private equity firm, you

know, kind of to the ownership. But you also have a responsibility to the person who spent their life building this thing, which I kind of maybe had an increased sense of because I built my business and I had sold my business to somebody else and I saw someone else making decisions for my business. And I think I did a pretty good job at that point of, you know, having a sense of separation of like, that's not my business anymore. But I still know what that feels like to be like, it still

happens that I saw some. They changed the feature in TeamPassword. I'm like, oh, I don't know about that on fellas like it was really like, I know that's gonna come back to bite you for this following reason. But that might be wrong. Anyway. So yeah, so I think that that is like, there's certainly a lot of pressure on you from that perspective. And then I think it's also it was also a novel experience for me coming in as the leader of a business that had been in motion for like

nine years previously. And so it's really I found it to be quite challenging, quite difficult to jump in, begin operating the business while at the same time trying to triage and understand where do we need to spend our attention most? And how do we need to kind of prioritize, you know, rebuilding the team, focusing on the product and on support and success and marketing and sales and kind of all these things together. What did our operations look like? And also just, you know, again,

it's a operating business. It's a business that's growing and you want to grow it faster. So you can't, I wasn't like I could just join for a year and kind of sit and observe it and be like, okay, cool. Now I know everything. The reality was, it is like the first like, full time day that I was at Baremetrics, I was on sales calls and I was talking to customers and I was getting out there. And I did not know the

product fantastically well at that point. It was my first day. But I was able to lean back on my experience of like, okay, well, I know what it is to grow a SaaS business and I know what it is to be in the space. And so I guess in retrospect, I feel pretty bad about whoever I took those initial, I should actually probably go and look at my calendar and see like, who did I take those calls with? And like apologize that I probably didn't give them the most accurate information. I probably

gave them a lot of, you know, I'll look into that and follow back up with you. But I did lean on like, okay, well, what's your goal? What are you trying to achieve? And what are you doing today? Kind of the traditional, you know, foundational questions you can ask anybody about what they're doing and how they might be a good fit for your product. So yeah, it was a lot of what's the phrase, you know, kind of like building the plane while it's flying or whatever, some phrase along

those lines. But also, everybody's watching you do it. So yeah. So that's kind of, yeah, I found to be quite challenging. It was a pretty tough situation.

of like, I don't, I was coming there to learn as well. And I was coming to experience that, you know and I was coming to make improvements. And, you know, I'd hope to think that my heart was in the right place. And so joining the business, it wasn't a mechanism of like, hey, I'm this smart guy coming in to like, tell you everything that you're doing wrong. It was like, hey, like, I'm here now to learn and to bring my wealth of experience. But I very much respect everything that you've

done. I have a lot of appreciation for everybody's here. I think that we've done, you know, from my perspective, looking at the outside, we've done like, 95% of things right. So, you know, as I tried to ramp up as quickly as possible, it was important for me to be like, hey, like you, everybody here is awesome. Like every everybody here rules until we prove otherwise. And that was like largely the case. I would say like the vast majority of people were, you know, at the top of

their class or whatever. That's not a great analogy, but so I didn't find that to be very difficult. And I think that again, it'd be very funny for you to like talk to, you know, reference check this and talk to them. Oh, yeah. Brian, when he came in, he was awful. I hated working with him. But I would suspect more often than not, they would probably say something like, yeah, like I really

enjoyed working with Brian. I really appreciate what he had to do. I just didn't agree with you know, we went from being a independently like a private tech company into a private equity owned business. And there's necessarily differences because of the structure of how that works. And so that's what I think that most of them would say. But again, it'd be very funny for you to be like, oh,

yeah, Brian is like totally delusional. Like, he's like, nobody liked him. He was very unpopular in his time there.

for, 300k went to his employees. So he took care and he wanted to take care of people in the business. Of course, there was always the Hacker News backlash of any sale, any activity. There's something happening on Hacker News, but from what I knew he really wanted his employees to be well treated. And I would assume that you treated them all. But the thing that I really want to know because you just mentioned this, right? The alignment between what a privately owned and private

equity owned business that kind of, yes, slight difference in alignment there. What were the things that you immediately wanted to change about the business when you went into it? Like what things that other people hadn't thought about that you immediately go for?

yeah, I just don't want to deal with it. So I'll give a couple of examples. So one and I'm sure we'll talk a lot about pricing and monetization and things like that. But like, one thing is that when Baremetrics operates off of MRR tiers. And so the more money you make, the more money we charge you. And that a lot of people like that and probably more people hate it. But most people hate anything where

they have to pay more money. For the record, I think that's like a really great model for the business because that allows you to charge a very small amount to the smaller businesses and then kind of if you're doing your job at Baremetrics, we should be helping you grow. And, you know, you should feel like we're a part of that journey for you. If you feel like you're growing despite Baremetrics, then it feels

predatory. And I understand that. But one of the things is that when you upgraded from one plant here to the next you had to kind of like go through a process to kind of like, approve that change for it to be like yes, I formally, like agree that I am now in this new plant here, which is like a very nice kind of thing to do. But the fact of the matter is, like 30% of people just never click the button that says like, I accept. And so they just and there was no, like, they just kept using the

product. So there's like a bunch of like little things like that. It's like, well, when we upgrade, we should upgrade. One other thing and I'll kind of just drop this as a quick note. I'm relatively confident we'll circle back to that. But we introduced called a cancel, which was very unpopular. And everybody hated that.

working? How can we do more of what's working? And obviously, do less of what's not working. When we bought the business, there was one person in marketing and they were focused basically exclusively on content. So okay, cool. And Baremetrics has always had great content. So we did a ton of experimentation there from things like what if we did like a ton of content? What if we like generated content, even before the AI world? And then like, what do we look like on social? What do we look

like in paid? What do we look like in all these, so kind of just like, taking that one team and then splitting that out. Like, we were just in content. Let's kind of branch out into everything else. Let's get on Jeetu. Let's get on, you know, it's kind of like, let's start to build out the roadmap of how we can begin doing experimentations to find additional growth channels for the business. Baremetrics never had anybody that was like a dedicated salesperson. So we hired a sales

team. And we kind of went through that process of like, what would it look like if you had somebody who was dedicated to you as you signed up to understand what your goals were? And help you get the most out of the tool? And how would that affect your conversion rate? And how would that improve retention of you know, if you came in and we knew for a fact day one, that your goal was to reduce your churn from 7% to 4%? Well, that's something we can rally around. And we can, you know, we can help

you work on that. And we can, in you know, this team spare time, we can look at your account and figure out ways to help you do that or find insights for you. Then, you know, technically, how are we doing, we went through a couple of things like replace the Stripe API that we were using. We could no longer use for new customers

so we had to replace that. We also migrated our hosting, which was kind of like a much larger pain in the ass and I think anybody anticipated it was going to be in retrospect, we should have anticipated that it was going to be a gigantic pain in the ass. And we should have planned for that accordingly. And then we also just kind of overtime because the team had focused in a lot of different

areas, we just kind of had like a backlog of books that were like, you know. One of the challenges with running a business like Baremetrics is that like when I ran TeamPassword, if you had a bug, the bug would be like, if somebody tries to save a password or a note with like a Unicode character or whatever non Unicode character, it would break. And the reason that it would break is because of the way the encryption works. And that character wouldn't work. So we have to either

whatever. We had to figure out a solution for that. We can write a test. I can write a solution for that and then deploy it and then it's fixed for everybody. Because Baremetrics is so data driven, the problem that you're experiencing, might literally only exists in your account. So it's like, because you are especially working with Stripe, there's so many ways that you can change your data. And you can have discounts at the customer levels. You can have discount at the invoice level at the

invoice item. You can have discounts at the product level. You can have coupons. You can have dollar off percent or whatever. So you just kind of run into this multifactorial situation where we just accumulated this huge backlog of like, issues that were really like only one account specific and that bug backlog was kind of like ever growing. So that was like a huge thing of like, when you sign

up for Baremetrics, you need to trust us for your data. And if the first thing that happens is you see something that's wrong, we have like, effectively, like 45 seconds to fix that before you're like, no, I'm not going to trust this, even if whatever, even if we can explain it away. We need to bring a resolution to that. So that was another thing of like, hey, how do we put ourselves in a spot where I don't think we ever quite got to 45 second resolution time, but how can we get to the point

where we're not in a spot where the bug backlog is ever growing? And kind of all these weird edge cases things are happening? How do we make the big picture improvements so that bugs are less edge casey and when they can be kind of more concentrated? And so we can make changes that will improve a series of issues that

might happen. And then how do we just like have like, we hired two engineers, who for the past two years have just gotten through the bug backlog and just have fixed like everything to the point where right as I was exiting, they're like, yeah, they're like bugs are done. Like what? Like, yeah, bugs are done. We're through with bugs like, awesome. That's really great. So I hope that answers the question. I mean, it's a lot of different things in a lot of different areas. But

it's kind of just, I think a lot of it's just bringing a new set of energy in. And then also, like I mentioned, kind of there is like the kind of playbook approach of like, hey, here are the characteristics of high performing businesses. We are going to deploy those practices here. And then you need to see if they work or they don't work or what changes you have to make in order to have success with that for your business that has your product, that has your customers.

Were there any existing processes or strategic planning systems in the business that were completely incompatible with this new playbook that you brought in? You know, coming from the bootstrapping or you know, mostly bootstrapped perspective into a more, you know, growth oriented world.

of like some, I feel pretty good about that change. But you know, it's like, it'd be like, you know, like Slack doesn't charge you for inactive members and things like that. And that's kind of like a product mentality. I think, certainly, the call to cancel change was like, totally, it's not like that. I guess that's like very antithetical to the mentality of the business previously and they want, you know, signup should be super easy and simple. And then exiting should be exactly

the same way. And in fact, we flipped both of those. We turned signups so now that we do have people that are hired to help you do that and there is, you know, white glove onboarding, if you want to do that and we do have a success team that will check to make sure that we're fulfilling our promises. So we've added stuff to the front end to make it more hands on to go in and then we added things to make it hands on when you left. So yeah, I would say that's pretty not like it doesn't like

run against like a process. But I do think it's like a mentality. Like there were just mentality changes that happened from when the business was run before to when it was my era of the business.

less aggressive about my perspective on this. Because the moment you started actually publicly talking about it, you did a whole lot of, I guess, a couple of videos where you talk both about your price increase. That was a thing, right? And the call to cancel thing and how you tried it out, what data you got from it, why you did it? I found in retrospect, it made some sense, right? It was still maybe

not what I would have liked, particularly as a customer at the time. But you know, it was something that from a business owners perspective, made a lot of sense, which is why I would like you to share your reasoning behind making your customers call to cancel a product that they didn't have to call to sign up for.

don't have to agree with the outcome, but you understood the path to get there. And you kind of you could conceptually understand and appreciate why we were there. And so, you know, I think that there's no way to kind of hear that without being like, well, the deployment of that was totally bungled, like communication on that was like, could not have been handled worse because it's like it once it got down the road, then you're like, okay, I understand it now. That

means that was understandable. And had I handled it better in front, I suspect a lot of the frustrations could have been negated. So yeah, the real purpose for doing call to cancel was there's two things. So one, again, I'm coming in as somebody who's jumping into the plane mid flight. And every customer touchpoint is like critical, especially people are canceling. Like the most important thing for me to know as a leading indicator of like, where we're going. It's like, why

are people leaving? And so we used our own product cancellation insights. And we allowed people to say why they were leaving. But I don't know. Maybe it's also just a function of like, I don't know enough about the business to be like, when somebody says, like, oh, I had that one bug. Like maybe the previous, maybe Josh would have read that and be like, oh, yeah, the one bug, like, I understand why that is. I don't know what the one bug is. So there's a big part of it for me to be

like, how can I learn as quickly as possible? Like, what's going on? How can I have conversations with people? And how can we kind of like, that should be like the biggest input for like, what do we decide to do moving forward? I think there was a perception that, you know, it's like a wind back exercise. And that happened

literally once the whole time I was doing it. I didn't even ask for it. It was somebody was like, I think the person was just so frustrated and so angry that after he kind of like, yelled at me for 30 minutes about like, how much of an idiot I was, he kind of like, he got it all out of his system. And then he was like, okay, well, we can try this again. Like, turn my account back on and we can make it happen. So, you know, that was really the primary reason why we did it. And it was like a

crucial learning point. And we did learn a lot. Surprisingly, most customers were so nobody liked it. Nobody enjoyed having to do it. But the majority of people would have a conversation on the way out. And the vast majority of those conversations were very useful and very thoughtful and very insightful. And again, it's kind of like your mileage may vary depending on the type of business that you're running.

But running a SaaS based analytics platform for SaaS companies like for us to get feedback from other SaaS businesses on, you know, our customers are just very articulate, be like, hey, well, here is what I was expecting. And here's what I saw. And then here is, from my perspective, the delta between those two things and here are three recommendations of ways that I would have solved this and if this was done by this date, I would have stayed. It's like, great, just like

and that's more than anybody's ever gonna type into a text box. But you know, so if you're running a different type of business, you might not get as good of feedback as we got. But that was really the major thing. We also kind of had this minor track of like us detaching from your Stripe account there were kind of like technical things and turn off things and exports and other kind of tactical things that like made a lot of sense. Like we had customers who still had web hooks

connected to us. Like their Stripe web hooks were going through Baremetrics. And then we had some sort of like, DNS issues and then that caused non customers of ours to have their payments fail, which I don't really quite know the mechanism for that. But I don't know why. Like, it's probably a part of a flow anyway. So like, they were like, super pissed at us. I'm like, oh, well, we need to like, you have to go

into your account and click X. And then we also, we have Baremetrics has an API. So there was a period of time where we looked, I think we got like, it's like 1.5 million API requests to all endpoints from non customers, which is kind of a spooky thing of like, oh, well, they're sending us like customer data. We have no contract

with them. We have no business relationship with them. We're paying to like, return 200, okay, because we don't want to return a non 200 status code in case that breaks their software, that this, you know, charge customer returned non 200. So, they're all those kind of like, it's kind of like a cornucopia of

technical issues. And I think at the time, we were more upfront with those technical things because that was more painful for us because we had just gone through having customers be or non customers be furious with us that their payments aren't going through because of us. And that felt very raw. But I really think that the real reason and I think the thing that to your point, the thing that actually resonated better with people, it's like, we have to know, we need to have a conversation. And

we're not trying to save you, we're not trying to keep you as a customer. In fact, like, again, it's only I mean, maybe it's happened more than once. And I think we've had people come back after the fact. But you know, the number of people that you save, like transactionally, in that call is like, one was actually numbers. I was gonna say zero, but I just told you it's one. So I don't think we were all right. I don't think and I know that we were not clear enough in the communication around

that. And I don't think I was honest with myself. And I maybe, almost internally thought like, well, the fact that I need to learn like, is that really someone else's issue? Is that our customers issue that I need to learn and I need to build our roadmap? And like, but I don't know, I guess I'm at peace with it now. It's like, yeah, you know, it's not the case that I'm going to know everything coming in here. I think it's important for everybody to do it, do something like this or I saw on

tech Twitter. Someone was talking about going white glove for their signup, like you can't selfserve signup. You have to talk to somebody. I think doing these things periodically are like, super useful. And so yeah, I don't know, I think that that's kind of the whole situation in a nutshell.

kind of the free alternative version to Baremetrics that everybody used. I remember personally from my own experience building a SaaS, I had Baremetrics. We paid $180 a month or something at some point. And we used Profit Well at the same time. And we used Profit Well for the Profit Well stuff and we used Baremetrics for the really good parametric stuff that Profit Well didn't have and it was kind of almost the same but it wasn't, right? There was a clear distinction between the

two. So I guess what most people that were in the industry and we're doing the exact same thing using the free product, obviously, why wouldn't you? And the product that you pay for for the extra things, they were like they were feeling, oh, wow. They're really trying to keep us paying customers there even though that there is a free alternative.

terrible idea. But I think it'd be very difficult because you can only cover so much and you know, also just being founder friendly, you need to be like at some point, hey, this is our lesson to learn. And I even think if Josh was like, hey,

totally get that. Like, everybody's busy and like having to do this extra thing for this product that I no longer want to use, it's like, hey, like, I'm moving away from this because it doesn't meet my need or it's buggy or because like, I just don't feel like using it. Or it's like, we thought it was going to be a good idea. But we just don't whatever, like your to do list as a founder or somebody that's in

time is huge. There's also the community of people who were not customers and who are just like, conceptually mad like this like, which is harder. customers or people that just felt it was morally incorrect to do. One of the things that I found and this was like, a very, it's not a piece of experience that I expected to get, but being kind of what Josh calls, you know, I was like, the main character of the internet for the day, especially with the consideration that

like our call to cancel thing. Like, we're like, hey, like, I'll put like my picture up there. It's like, you're going to talk to me, this is not like, whatever. And so like, my picture was, like, you know, like 4000 tweets of like, hey, look how dumb this guy's face. But like, one of the observations I had is that and this is, I don't say this to minimize like anything. But I realized that a lot of people were

just having fun. Like, they're just doing the drama thing. They're just like, this is like, whatever unpopular chain when Coinbase is like, hey, like, whatever, no politics here or whatever. Like, they were like, I think that was actually around the same time. I think that actually took the heat off of me was Coinbase was like, hey, no more politics. And people were like, oh, these guys are idiots and I can't

believe it. And you know, whatever. I would go through the replies, which, you know or the messages, which I don't think was actually a healthy thing to do at the time. But then I realized something oh, they're just having fun. Like, this is just like

I'll follow them. And then it's like, you saw just like, I saw it firsthand how quickly they moved on to the next thing. This was not a durable concern for them. You know, for the first audience for our customers like and the people that we should actually care the most about, not that you shouldn't care about other people or whatever. But you know, for the people who are actually legitimately affected by

it, I think that audience was much more understanding. And you know, that was the audience that like, in fact, it's like the only group of people that I could actually do something for. But yeah, we had the secondary, much larger group, much angrier group of people that, you know, it's kind of like, I guess, it's probably something you know a lot more about of kind of more, you know, building with a community and

kind of like, it's not just about what you do. It's kind of like not even necessarily what you say about what you do, but there's like, you kind of have to go to the third level of like, what is the perception of, you know, it's going to go into somebody else's brain and then they're going to process it. And so you kind of almost need to, well, you can choose not to worry about that, which is probably the same thing to do. But you know, that's also kind of another level of

complexity. That kind of goes back to your initial question of like, hey, Josh was so open, so in public that that was kind of ingrained in the DNA of Baremetrics. So to some extent, not a surprise at something like this. It was probably going to happen at some point in time, unfortunately.

a nuisance. Obviously, from a business perspective, it makes perfect sense. And the weird part is that most or if not all, of Baremetrics customers are businesses or at least, you know, like founders or people that are close to the things that matter in business. So there was, I think that made it also so juicy for people because they understood not only okay, this is something that bothers this person for some reason. But this is a behavior that I might also in the future want to

take. And I'm gonna see somebody else experiment with it, right? It's kind of an observation of somebody else's experience. It's kind of like watching people fail at play video games on Twitch.

infinite kind of epi cycles of trying to figure stuff out. In the end, the best way to deal with it is really just to let it pass through and wait for Coinbase or Basecamp to do something

ends of the spectrum. So when I ran my business TeamPassword, we spent, I spent all my time I actually, like, became a developer through building that product. So like, all my time was spent building the product. And I spent no time on sales and marketing. And then I came to Baremetrics. And most of the effort was in sales and marketing. So I kind of got to see like, what is that? What are the opposite ends of the spectrum look like? And then at TeamPassword, my pricing was

too low, like our cheapest plan was like seven bucks a month. That's like, are you going to trust your business's passwords to something that's like less than your Netflix account? And then, you know, over in Baremetrics world, we got were like, we're all the way up into premium pricing territory. So we're like, all the way on the far right hand side of like and, you know, like what you mentioned before about like, hey, it's like, super easy, super transactional, you know, no fuss, that was

kind of the TeamPassword way. And I got to see like, okay, what would the kind of more white glove approach look like at the Baremetrics side? So and you kind of like, you go down the list for basically, what does it look like when just I'm the engineer? What does it look like when we have 10 people writing software for a product? What it looks like, when you have technical leadership? What does it look like when I do everything? What does it look like when I have you know, a team of

directors and those directors have direct reports under them? And like, what does that structure look like? So that's all to say that, you know, I kind of got not that I wasn't like super diligent about this. But and I think it's more luck than anything else. But I got kind of the exact experience that I was looking for. And going over the course of three years, eventually, you get to the point where

it's like, okay, cool. I'm kind of like, doing the same thing over again. I'm doing, you know, kind of not necessarily repeating, but it's kind of like rhyming. And we're kind of like, going through that process. So I mean, that was really the situation of like, I'm like, okay, cool. You know, I've experienced. I've learned, not necessarily all that I'm going to learn, but we kind of just got to an inflection point where it's like, okay, I think it makes sense to move on the

private equity firm agreed, you know. So I think it's like they also going back to what's their structure and they have very specific financial milestones and all the governance and what they're expecting to see. Like, they have very strong opinions about what's going on with the company. I have strong opinions, too. And so I think it just became almost like as a confluence of things. So okay, I think this is just

like the perfect time to be like, okay, cool. I've gotten what I need to get. I can make some room, which is like, I guess, maybe an extremely polite way to put it for saying, like, hey, let's, you know, let me step out of the way. And then let me kind of, for me, selfishly, to figure out, like what's that next level up going to be for me and then, you know, let the company kind of go on to potentially a

new or different trajectory. Like, without me there, the capability to have large changes within the company or even just, even from a culture perspective, like, it's just way easier because I'm always going to anchor Baremetrics to the Brian way of doing Baremetrics. The same way that Josh did, like with Josh, if Josh decided to stay on post acquisition, like that would have been way different because like, the business is always going to be Josh Baremetrics until Josh is no longer

there. So it's kind of not exactly the same thing. Certainly, like my mark on the business is not as nearly as large as Josh's but, you know, that's kind of the general idea of, okay, like, it's kind of like, kind of time, I mean, there's no perfect time to do stuff like this, right? It's not like and this was not like how it was exactly written up. But it felt good enough and everybody was on board. And so

I'm like, okay, cool. Let me kind of step aside and figure out what the next thing is going to be moving forward.

paths forward for me are one, you know, go into PE again. That would be like the another company or a director role. What is gonna be the next thing that you want easiest, most obvious thing of like, joining another firm, being a CEO for one to do? of their businesses, you know, hopefully with kind of material differences. So I can continue to learn and kind of expand my skill set and what I'm even just the

different looks that I'm getting. But you know, the kind of the pro side there is like, yeah, I will be able to step into basically any CEO role at any tech company, owned by PE firm, do a very good job at that. The downside is that I might just put myself back in the same exact spot that I was before. So it's like, hey, like, if I left that, you know, it's easy to get to, probably extremely lucrative, but like, you know, there's a higher than average chance that you just put yourself

back in the same situation. And if you're being honest with yourself and you're kind of, you know, you're being a little bit career add and you want to get new things, you want to kind of move up to the next level, putting yourself back in that same situation may not be the best decision. Or you know, PE is a class or even like, you know, just capital allocators in general is a class. So there are huge differences

between those. So I'm not saying there's not an opportunity out there. Actually, I am saying there's an opportunity out there because I'm putting it on my list of things that I might do. So that's kind of like path one. Path two is like, maybe I join another tech company, maybe I join a big tech company, I thought. You know, I've never worked at a company with more than like, 100 people, 200 people before, like, I could experience what that's like. That would be a very different look. I

think that'd be extremely, extraordinarily different. But, you know, again, that's almost a downside too of like, it's so different than what I've done before. The likelihood that I find myself in the spot where I'm like, oh, like, I don't get to make all the calls here. I don't get to, you know, do what I want to do. That might be a little bit of a frustration, but it's still kind of on my list to look around. Number three, start something new. And I think that is that's the one I think

that's like the biggest fit overall, you know, long term. But I think that would introduce the most stress to my wife where I'm like, alright, we're doing it. We're getting back on the road again. You know, I think that also kind of looking back to my previous experience, I ran you know, TeamPassword on the side for two years and let it kind of build up and kind of de risked the process so, you know, I don't know that I necessarily and I also, selfishly, I kind of want to enjoy the

process. So, like, I don't want to like build something and be like, okay, I have two months to like, prove this out. So I need to get to 10k MRR in two months, go. Like, that seems like that'd be a very stressful and high risk situation.

this. I don't know how I'm going to do my job after we cancel it, but we just have to. And so for me, that was like one of the, you know, that's like the conversation stands out in your mind of like, it's not that we're not delivering value. It's not that, you know, it's just like, people are just very concerned right now and very protective of cash flow. They want to be in a very defensive posture. So yeah, I mean, maybe now's not the right time to build

something that's a real problem that people really have a need for. And you're probably going to go through some number of months of validation and you know, getting initial users and testing, you know, and maybe you're comfortable giving the product away for free until you have something that, you know, people indicate that this is not something that we could live without before you start figuring out

what it's worth. So yeah, you know, kind of, I don't know. Yeah, I think that your turn there is kind of how I feel, too is like, ya know, it's might be a good time. But yeah, I certainly over this period of time, I want to, you know, over the next couple of weeks, I want to build a couple of things and launch a couple of different products just because I didn't do that while I was at Baremetrics. So even just

to kind of knock the rust off, have a little bit of fun. I've got a bunch of, I have a Trello board full of ideas of different things that have frustrated me or things that weren't available. So and I just want to play with, you know, the technology world has changed. I'm a Rails guy. So like Rails is like totally different now than it was before. And I played with a little bit. So yeah, I want to do some of that.

went through all these different angles. And he realized that the thing that he loved was, it wasn't about necessarily about industry or like I don't know, he kind of got to this point where he's like, yeah, the thing I realized that I love is like this whole field of like, sales enablement because it's a real problem. Nobody ever cancels these tools. I was joking with him. It's like the thing of like, oh, yeah, this thing, like, manages the entire infrastructure for our entire

product. It's like $25 a month. This is a sales tool that automatically adds note to our CRM. It's $50 per user per month, paid annually, you know. So I'm giving a pretty poor rendition of what he talked through, but that really got my mind spinning of like, what are those kinds of fields of like, you know, similar to sales enablement. I've always run into problems through just running the business and being like, you know, what is a frustrating thing to run into or that was

why I had TeamPassword. Like I worked at a company where we had a bunch of interns. Those interns would quit all the time. They had access all these passwords. And so basically, like, every third Friday, the whole company was like going down on a spreadsheet of passwords and changing it. I'm like, man, this sucks. So that was like the entry point there. So I mean, that's kind of my general mentality of like, as somebody who's run businesses and is run into problems like what do I wish I

had? I'm a big fan of the product bento and if you're familiar with. So like I just love that mentality of like, well, here's something that's available for a lot of money. And it's like super up market and has a ton of like extra features that kind of makes these more expensive things worth it, but kind of like not really. So like, I'm going to build like the 80% of the features or I'm going to build whatever maybe the 20% of the features that are going to give you

80% of the results. I think he probably has more than 20% feature parity. But you know, kind of like and I'm going to offer that for like a reasonable price. So one area that I've thought about is like, you know, managing like customer success. I think it's something that's especially right now talking about building in this climate, people are very concerned about customers churning, being on top of that, being on top of annual renewals, knowing which customers are going stale, which

customers usage are falling off. And all the tools that exist are either like using like, a spreadsheet, which sucks for all the reasons and it's great for all the reasons that using a spreadsheet is. People are trying to use like sales funnel like pipeline, you know, management. But success, it's not like a straight through

and then you're done. It's just like a circular thing that with lots of you know, inner loops or you have something like a HubSpot or Gainsight, which kind of go into that more premium price that you know, a smaller company will be priced out of. So that to me is something that is like a good shaped problem of like, how do we solve this? How do we, you know, build the supercharger on the smaller teams that

are not going to get to hire anybody anytime soon? And then how do we like defend, like, can this product defend itself from the perspective of like, hey, this is valuable to your company? Here is the turn that you were able to save, here is the you know, here are the very active users that you know or here's the people that reactivated, basically. It's like a pre reactivated of like, hey, don't let them go dormant and try to win them back, like do that while they're still paying

customer. That's kind of a good example of like, something I've thought about a bit and there'll be like a good like, category of like problem to solve that I'm very familiar with it. I wish I had it. And it's kind of like, of the time right now. And I could build that. I think anybody I think, you know, but before this podcast ends, half the people listening will have built it. But you know, but that's kind of like an example of like, the type of it's not really a specific vertical or industry

or anything like that. It's kind of like, I guess that's my thesis of like, what I wish I had when I was doing previous company X.

nice dual perspective, that's an unfair advantage. And I certainly hope that you can use that unfairly even more to your advantage because it sounds like you've given this a lot of thought. And if there's one thing that is palpable in this description is that you want to get going, like it's so noticeable.

to try to do too much at once all the time. So now this is my thing for today. And then after this, you know, whatever I'll do, I watch some TV or whatever I want to get if I want to do a little, you know, study or something like that. And then you know, when somebody reaches out to me, it's like, okay, when's the next day and I've found that it's enough that I don't feel like so I go to the gym every morning as well. I do jujitsu. So I like rolling around on the ground and I try to

choke people and they try to choke me and somehow it's a very fun thing to do. And then you know and then I do one thing and then that doesn't allow my panic to set in of like, hey, you're not moving forward. But I'm also finding that I'm making such quick progress on every it's like actually like I've had, you know, a bunch of different calls with people that have been like, hey, well, let's you know, I'd love

to work together. What do you think about have been open and that was another reason to post publicly about it people like well, have you thought about something like this? I'd love to work with you on X. I'm, you know, work Friday. I started on Monday and I already had a great bunch of great conversations. So I'm kind of like, how do I keep this one thing a day? Yeah, one of my friends from the gym gave me a book, not this book. That's your book

employed right now, you know. So it's like, so I really have to look at that. And that's something that's coming from inside that is, has that tendency to want to fill up and go as fast as possible. But I just told you how nice it feels and how much better and in fact, even reaching out to you, when I got that response to the tweet of like, hey, well, why don't you talk about some of the lessons that you've learned? If I was slammed back to back, I would have probably just answered in a

quick tweet and moved on. But actually, I'm like, oh, let me spend some time to think about it. And as I was thinking about, I was like, oh, this might be a great conversation. And so this conversation is a direct result of not, you know, having being back to back all day.

tweet that you sent. Like people said, oh cool, congrats. That's awesome.

still way too much. So if anybody has any questions, my favorite thing at Baremetrics was being able to chat with customers and like doing like customer development or sales or like really like any functions, support, success was ultimately came down to like helping people improve their businesses, like they wanted to grow more quickly or solve a problem. It's always my favorite thing to do to help people like what you mentioned about, you know, kind of having that

external viewpoint of like trying to help, I love doing that. So if anybody's listening to this and if you'd like to be my one thing for a day, I'd love to help anybody out. It's just my, I always kind of turn it and make it a little bit cheeky. But it's like, it's my favorite thing in the world to like, talk with somebody, hear their problem, give them you know, a solution or two or three

solutions and then send them off and they have to do all the work. They have to do all the effort and I get to feel great that I helped them and then maybe they come back in three weeks and like it worked. And you know, I get to feel great that it worked. And I didn't have to do all of that work. So I'm always happy to you know, even listen or provide a shoulder to cry on and fight if I can

help. I love doing that. That'd be a great use of my greatest of my time right now as I'm in between having a full time gig soaking up most of my time.

attention of an acquirer. The problem is you're not growing for whatever reason, either lack of focus, lack of skill or just plain lack of interest and you feel stuck. Well, what should you do? The story that I would like to hear is that you buckled down and somehow reignited the fire. You got past yourself in the cliches and started working on the business rather than just in the business. You started building this audience and move out of your comfort zone and finding that sales

and marketing the way you're supposed to, right? And six months down the road, you're tripling your revenue and everything is great. Well, reality is not that simple. Situations may be different for every single founder facing this crossroad. But too many times this story ends up being one of inaction and stagnation until the business becomes less valuable or worse, worthless. And if you find yourself here or your story is likely headed down a similar road, I offer you a

third option. Consider selling your business on acquire.com. Capitalizing on the value of your time is a really smart move here. And acquire.com is free to list. They've helped hundreds of founders already. So just check it out. Go to try.acquire.com/arvid and see for yourself if this is the right option for you. Thank you for listening to The Bootstrapped Founder today. You can find me on Twitter @arvidkahl. And you'll find my books and my Twitter course there too.

If you want to support me and this show, please subscribe to my YouTube channel, tell your friends about it, get the podcast in your podcast player of choice and tell your friends about it. Leave a rating and a review by going to (http://ratethispodcast.com/founder). Any of this will really help the show. Thank you so much for listening and have a wonderful day. Bye bye