The Exchanges

Every argument clarity score on this site is built from rows on this page. Each question and answer was assessed with names hidden, the host's own answers included, on four things from 1 to 5: directness (does it answer the question asked), coherence (do the ideas follow), precision (concrete details and clear references), compression (says a lot per word). The weighted mix (30/30/25/15) is the exchange score. A person's published score averages their exchange scores on raw tape only, at least 8 of them, shrunk toward the cohort mean. Full method →

532exchanges match
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Answered produced feed D 5 · C 5 · P 4 · Cm 4 4.60

Q Nice. What were some common questions that buyers had? Were they interested in the product most or the revenue or both? Um, how did those initial initial calls go?

A Well, a lot of people, uh, I mean, obviously a lot of people were very interested in revenue numbers, uh, especially like what it's going to look like in the future. Um, For any potential dips, they obviously asked about why did it dip here or why was it high here? Uh, so those were kind of the questions that were asked, but also they asked about the customer base. So who's your target audience and kind of like, um, who are you making the most money with? So I, I guess the two main categories were, is this a sustainable business? And the other question is more about like, uh, is there a potential to increase revenue in here?

AI assessment note: “a lot of people were very interested in revenue numbers”

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Q you know, potentially millions in taxes. So looking that up, Uh, in advance is also, you know, really great advice. And then acquire as well. I'm a little biased there though. Um, what did you do to celebrate the acquisition? Did you do anything fun when you closed? Did you buy anything? Did you, you don't have to go into too much detail here, but did you do anything fun?

A Well, I haven't tweeted about this yet, but I think I'm going to say this on the podcast. So the very first thing, and I already announced this, the very first thing I did was I called up my bank. And I told them, Hey, I want to buy a bunch of gold. Uh, this was more of just like an investment for me. Uh, but honestly, to me, it's still kind of a fun thing being able to buy this amount of gold and just like going in there because I didn't like, I did call them, but after that I went into the shop and I told them, Hey, I want to buy this amount of gold. And they just looked at me in shock. And the lady there was like, do you work in it or something? And I was like, yeah, kind of, um, So, yeah, that, that was super fun, and the people that are, like, seeing their reaction to it, uh, was also, like, super funny to see, uh, because most of them did not know where the money came from, so they thought I was laundering money or something like that.

AI assessment note: “the very first thing I did was I called up my bank. And I told them, Hey, I want to buy a bunch of gold”

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Q What an amazing business. I love this, Chris. This is great. Um, tell me this. So, you know, you're, you're running the business, um, is profitable. What made you decide to potentially sell the business?

A Sure. Um, I think it was a natural progression in what I want out of life rather than any compelling reason. So we're a profitable and growing business. It doesn't take me a long time to run it. I typically spend four to eight hours a week running the business. Um, but last year I'd made the decision to simplify my life a lot. Because me and my wife are planning a family over the next year and I want to maximize that time. So the way that I've always been as a business owner, Andrew is very time freedom focused. I've, I've happened to have built some bigger businesses, but it was never an intention. It just happened to be something that I'm grateful to have done, but I've always focused on maximizing my personal time and freedom for my hobbies and my family and my dog and whatever. Right. So, so the way that I built businesses from day one is to be very efficiency focused. So that they can manage themselves to a large degree. So last year, um, I was running, uh, several different businesses, uh, three cleaning companies and, uh, a VA agency and a consulting agency. And I just, early on the idea of being a serial entrepreneur is fun and it's invigorating, but after a few years, your focus is so split on different projects that at least for me, it kind of lost its magic. And I found myself being pulled in too many different directions. And so I decided to simplify and sell my cle…

AI assessment note: “I'd made the decision to simplify my life a lot. Because me and my wife”

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Q name or anything like that, but I assume they had these qualities that you're describing. Um, was there anything else that really stood out about them? Was their offer the highest? Did they have great terms? Did you guys just get along really well on the first call? Did you kind of just, you know, like this buyer just kind of gets it? Like what made this buyer stand out?

A I'll add more detail, but actually the answer to everything is yes. So I had done several acquisitions myself, but also sales, um, again, in the cleaning industry. But they were always to people who I'd already had a pre-existing relationship with. Maybe they were another cleaning coach in the industry, or they were a student of mine. There were, there were people that I already knew and could to a degree vouchsafe for that they would be responsible owners. So this was my first time selling a company I built to a total stranger. Um, and I was very nervous about that. So Kai will tell you, if you ask him, I peppered him with questions about that man. Um, but to, to answer your question about him specifically, the buyer, we jumped on a call. And I was, I was, you know, a little interested in him, moderately interested perhaps because of his background. So his background I'd noticed was in the staffing industry and virtual assistants really are temporary or permanent staffing agency, um, just for the virtual world. And so he'd scaled, um, staffing agency very successfully up as well as several other companies in the past. So he'd had the experience of taking a company from my current size. To 20, 30, forty million a year. So he'd actually had very specific industry experience of doing this just in the IT industry instead of in the virtual assistant agency world. So there was so mu…

AI assessment note: “actually the answer to everything is yes. ... his background I'd noticed was in the staffing industry”

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Q Nice. So let's fast forward a little bit. So things are going really well. You have partnerships with QuickBooks. You're in the Microsoft App Store. Uh, you know, things are growing fast. What made you want to sell the business?

A I think we started to come to the realization that it wasn't necessarily going to be a venture-scale growth opportunity in the way that we originally thought it was, and so we started working on another product really focused on AI, and it became pretty obvious to us pretty quickly that AI for, you know, early-stage CFOs, the market wasn't there. They weren't going to be the right demographic, the right buyer for what we wanted to build, and so we had this product Genius sheets. And then we started working on a new product, which is ultimately my code that we're working on now. Uh, and so as we started building more of these AI features, we realized we still had this like valuable business that we were operating on the side, uh, and started to think through ways to monetize it really through ultimately selling it.

AI assessment note: “realization that it wasn't necessarily going to be a venture-scale growth opportunity”

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Q Nice. I love that. Tell me about the calls with the buyers. Um, how did they go? Anything surprising? Um, were they all kind of the same, high level? Just like someone's listening, probably thinking, you know, when I get on the phone with a buyer, what do I say? What do I do? What can I expect? Um, any thoughts there?

A I think it varied depending on the type of buyer. So the buyers we talked to that had a really deep finance or accounting background really understood the product and who it was serving and who we were selling to. So there was much less questions around that and much more around like, what does usage look like? Like, what's your retention numbers? Like, going into all the nitty gritty of basically trying to find where There's hair on the deal or not, like trying to uncover those secrets for the people that really didn't have the subject matter expertise and were more just SAS buyers potentially interested. I think there was a lot more education upfront in like what this tool is, who it's for, how they would go about marketing it. And so pretty quickly we realized that there was a large enough concentrations finance buyers as people with a real subject matter expertise that that was probably gonna be a much better fit. To both take over the business and not have the hassle of us wondering, A, is it going to continue operating? But B, during that transition, they know exactly what they're getting and that we can be, like, feel good that we're giving it to somebody who gets it.

AI assessment note: “I think it varied depending on the type of buyer.”

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Q Nice. Okay. So you find a buyer, everything was good in terms of the offer and the valuation and the terms you sign that you move into due diligence. How did that process go? How long did it take? Um, any hiccups, any surprises, any advice for people about to enter due diligence?

A I think just try and be as upfront as possible around everything that You're selling to the people when you're getting the offers, especially if you have multiple offers, it's better to be upfront and be like, hey, this is the deal, like not trying to hide anything due diligence. We were fortunate that we didn't run into that issue. What we ran into actually is because we're listed on the Microsoft app exchange. Microsoft makes it really, really, really hard to transfer that to another entity. Um, and so we wound up having a bit of a prolonged process because of Microsoft support and going back and forth Microsoft for almost two months. The rest of the diligence for us was very straightforward. I think we we had provided all the underlying documentation originally when we were going through the initial process and then we provide some access to our systems and other places once we had everything signed just to make sure that, you know, all the T's were crossed and I's were dotted. And so overall, I think the more information you put up front, it really helped on the back end of the diligence. There wasn't that much. It was a lot of like, let's transfer accounts and make sure like, When you tell us there are a hundred users here and for the segment that there are a hundred users.

AI assessment note: “prolonged process because of Microsoft support and going back and forth Microsoft for almost two months.”

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Q That's so true. That's a great tip. I love that. Thanks for sharing that. Um, okay. You got customers, you got product market fit, things are going really well with lead gen app. What made you want to ultimately sell the business?

A I think a number of reasons. One is that we had too many things going on as in too many different business models. So my co-founder had a web design agency. I had with him an SEO agency, and then we had the SAS as well. And then on occasion, I also had done Uh, SEO consulting, but packaging it together, maybe three, three big thing. And the SAS needed a lot more attention to really see it succeed to a big level. And we couldn't really do that. So we couldn't give it what it needed. We felt the other second reason was it was also a bit stuck. Like we had decent growth in the first years, and then it hit some sort of a plateau and it's not a good feeling to be stuck for too long. Then you need to think, oh, what do we do now? Do we really go all the way in? Pivot, do something slightly different or move on. I have, I should, I should add to that the business itself, the numbers always grew very nicely, even in the last years, but through other revenue streams. So we monetize the company by adding new revenue streams. We got a little bit creative through our SEO and we're selling other related services. The SaaS was a little stuck and, and I think it was healthy to take some action and combining that also with the fact that there's other things going on, I think was definitely right. Thing to do to, to sell it.

AI assessment note: “One is that we had too many things going on as in too many different business models.”

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Q lots like big deal numbers, right? So it makes sense that there's always going to be the hesitation, but, um, I haven't quite, like, figured that out yet. Let's say in the future of a cell, cell business again, how to differentiate someone who's really interested versus someone who's just, um, medium interested. Maybe have you got, like, a thought on that? Like, how to, how to filter that out?

A Yeah, I know exactly what you're talking about, because a lot of buyers are trying to keep the cards close to their chest, where you don't want to come out and say, hey, like, I gotta have this business, this is a perfect fit, because then you know that's the buyer that is going to make an offer on the business, um, is likely You know, willing to pay more than typical asking price, but what they do is just ask like, Hey, based on everything you've seen, uh, what else you need to see to spend a letter of intent? Um, or based on, you know, this initial call, um, what are your thoughts on the business? Can you see yourself acquiring something like this? And if not, do you have any hesitations? Um, and that way you're just getting feedback and some responses there might be, oh, I need to see the product a bit more, or I'd love to see this documentation, or I need to see a cleaner version of your P and L or. Whatever it is, like, you get that information, and then you just keep the ball moving forward, just like in sales. There's an acronym I love using called BAMBAM, which is after every call that goes really well. See if you can book a meeting from a meeting. So the call goes really well. You can say, hey, I enjoyed our conversation. You know, based on what you've seen, um, what else do you need to see to potentially make an offer? Like, what are you, where are you on that? They'r…

AI assessment note: “what else you need to see to spend a letter of intent?”

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Q Right on. All right. In terms of the due diligence process, how did that go? Uh, any hiccups, anything that surprised you?

A No, no, no, no hiccups, nothing. Um, nothing surprisingly, um, yeah, nothing really surprised me. Um, I mean, I'll be honest here. Our setup was, was very, very simple in a way, you know, we, we generated all the revenue directly from, from Wix, not a lot of different, you know, uh, payments providers. Uh, so they were in a way our own only client because, uh, they collected the payments for clients and then, uh, and also we didn't have a lot of, uh, um, uh, like, uh, Costs for, for running everything. So it was, you know, on our end, it was very simple, simple business. And I think because of that, it was also a simple transaction.

AI assessment note: “No, no, no, no hiccups, nothing... nothing really surprised me.”

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Q Yeah, I mean, AI is just changing everything. Being able to create, you know, small MVPs or prototypes in literally days instead of hiring people is pretty crazy. Tell me, how did you get your first customers? You build the product. What happens next?

A Um, How did it get to first customers? So, I mean, the, the niche that I was in, the, the actual music software industry is probably not that big of an industry as a whole. There's, there's about 10,000 companies in the entire industry at, at most, and I would say if the top 50% in sales is probably attributed to maybe like a hundred companies. So it was relatively simple to reach out to all the companies because I already had a lot of their contact details from my previous e-commerce company that were Out with music software sales. So I literally reached out to them and said, here's what I'm building. Here's how it can solve your problem of, um, like difficult customer support, customers having to download products through their browser, having to email support their support teams a lot. And, um, I basically said, here's your problem. Here's the solution I'm building. And here's how much it's going to cost. It took a very long time and to actually grow it because like to get companies on board, because what I actually found was It wasn't a case of the solution was bad. It was a case of it required a change in culture. I think within the industry, like people had always used download links through their browsers. So, or like buying DVDs and get them shipped in the post. So it required a real shift in, um, this culture and how people, people's expectations of how they receive so…

AI assessment note: “I literally reached out to them and said, here's what I'm building.”

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Q What was the business model on the B to B side and the B to C side too?

A Uh, yeah. So on the B to B side, it was a revenue share. So we would take a percentage of each company's revenue. Um, so for a small company starting off, obviously it was a great deal for them for larger companies as they grew. And as we added extra features that they wanted, we would grow with them too. So on the B to B side, it was a revenue share for every products that we delivered. And then on the B to C side, it was a e-commerce store within the app. Um, so as customers use the app to download products, they could also use the app to purchase products, which is where we would, um, sell the products to them through the store. And we would receive a Like a higher split on the sale of a product through the e-commerce side.

AI assessment note: “on the B to B side, it was a revenue share... on the B to C side”

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Q That's incredible. Tell me, what made you, um, make the decision to sell the business?

A It was a couple of things. So, um, I kind of feel like everything comes in cycles just as a, as an entrepreneur. It's like the fun part is building and then the less fun part maybe is scaling. And I kind of found like my energy had started to die out a little bit where I had got through the fun part and I couldn't see much, um, I couldn't see much more fun in what I was doing really. It was becoming a bit monotonous and I wanted to move on to other things cause I had lots of other side projects in the go. So that also came at the time where there's a tax break in Ireland and it just made sense to take advantage of it. So when I sold the company, I was able to take advantage of a far lower tax, um, tax break compared to just paying myself through the company. So that was also beneficial as well. And then on top of that as well, we had a second child and it was just becoming quite, uh, difficult to balance my time with at all. So all of that, the other side of it was as well, I guess, like, There was a growing anxiety, I would say, from, um, just managing it, which I never really hear people talking about, but it was this kind of, sometimes I have this sense of dread where I was providing a service that was, um, important to companies, and if it went down, obviously, I'd kind of get really upset, and I'd have to work through the night to fix it, and I had a couple of those nights…

AI assessment note: “It was a couple of things. So, um, I kind of feel like everything comes in cycles”

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Q Nice. I like that. Uh, where'd you get the idea for this? Did you work at a large company before and you saw it was really unorganized or have used like another LMS? Like, I don't think this is a product a lot of entrepreneurs go like, I'm super excited to build a corporate SOP LMS.

A I, uh, the journey started with a friend, um, Heaton Saunders. He actually asked me to go fifty-fifty into a small tutoring business. Uh, we weren't the tutors, but we both, uh, studied engineering. So I studied civil engineering. Um, and at the time, um, we thought, hey, you know, it's a little bit of extra pocket money. We basically took a commission from, uh, distributing tutors and finding clients for them. Um, it was, uh, quite a lot of manual work, a lot of phone calls, and things like that, and I just realized it wasn't really that scalable, but I really was passionate about education in particular, and, you know, helping people grow their knowledge, and the idea came about, um, where I kind of realized that the university tuition was, was quite expensive, and a lot of that went to things like maintenance of the buildings, you know, paying for water, electricity, Fields, rental, et cetera. But, you know, a smaller portion towards the actual material. So I thought, well, if, if the material's online, um, I felt like we were inevitably going to go online. And this was back in about 2017 or so the idea came about. Um, so from there, just looked at, you know, looking at building a learning management system and trying to make it as smooth as possible for, for training to be done online, essentially.

AI assessment note: “the journey started with a friend, um, Heaton Saunders.”

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Q Nice. And then with your first customers, was it, like, a completed product? Was it an MVP that they were signing up for? Were they thrilled with it? Was there a lot of buzz?

A At the time, it was whatever they needed, whatever they needed to be, you know, built. It was very custom, almost hacked together to, to build a custom product for them to make sure that they were satisfied with it. I was still working At the time as a, as a full-time engineer, and I didn't really have much capacity to, to build, but this was evenings and weekends. I was doing this on a part-time basis, really. So managing two customers, I had no employees. It was just me completely bootstrapped. So really just tried to build, uh, when, when they sent through a support ticket, it was basically, yes, we've got that, build, and then respond, which was nice. Very, very, very fast.

AI assessment note: “It was very custom, almost hacked together to, to build a custom product”

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Q That makes a ton of sense. Um, what was your, uh, knowledge around acquisitions? Did you have any expectations going in? Um, like, how did you think you would sell the business versus, like, did you go and Um, reach out to acquire and you thought it would be a really long process, really short process. Um, then what were your, what was it really like?

A Uh, before listening, I used to listen to your podcast. That's why it's such a privilege to, to now be on one. And I try to learn as much as I could from, you know, the talks that you gave the founders, you know, tips and things like that. So it was just a preparation process and from around, The, the beginning of, you know, I would say mid, mid last year, uh, so mid-twenty-twenty-four, there was some prep work that went into it, and then to list on acquire, I mean, expectations were, I didn't really have expectations, because it was my first time, but I had a lot more excitement around the fact that there was a marketplace. I had Kai, which is amazing, by the way, and he helped me through this entire process, and basically hand-holding, so things that I just didn't even think of, it was very proactive, and I found a client being really, really proactive with sharing resources, you know, sharing presentations, slides of a roadmap of the journey, which removed a lot of uncertainty in the process. You know, by week three, you should expect this, et cetera, et cetera. You should start contacting buyers. These, these are the type of things you should expect. So it alleviated a lot of the, um, uncertainty.

AI assessment note: “expectations were, I didn't really have expectations, because it was my first time”

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Q Gotcha. Um, tell me this, if you could go back in time and give yourself or maybe another founder asked you, you know, your top three tips for, you know, getting acquired, what do you think those would be?

A I'm also speaking to myself now, should I do it again? Now that I'm thinking about it, um, I would say start with the end in mind. So I think when I started the business, I didn't really have this end goal. It was just to kind of earn an income Get out of my full-time job. There wasn't an end goal. So if, if you're going to start a business, I would definitely say reverse engineer the process. Um, I've, I'm fortunate enough to have been acquired now and I've gone through the process. Now I know what to plan for, you know, which documents should be paid, prepared, what in advance, what to keep tidy, keep the books tidy, keep everything neat, um, so that you can be more attractive to a buyer. I think when you have a complicated business, um, from a, from a legal standpoint or from just, you know, not well documented, it can take, it's, it's a little bit less attractive from that perspective. So starting with the end in mind and preparing for it early, even if in my opinion, you're not intending to sell anytime soon, but just when I've started preparing to sell, I found that I started putting in more systems into the business to start to Remove myself from the business, which is always a healthy thing, um, for scale, so I would definitely say that, um, and then in terms of other tips for, for being acquired, I, I would definitely say, think of the, um, buyer as well in the process…

AI assessment note: “I would say start with the end in mind. So if, if you're going to start a business”

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Q Nice. How did you find your first customer retail?

A Yeah. So that's a, that's a very easy question. And that was the, the question I was, uh, I had built a bunch of startups and did, you know, didn't really get customers. So I was like, I need to find some way of like automatically getting customers. So what I did was, uh, so Stripe actually came out with a Stripe, App Marketplace. So it's similar to, like, Apple App Marketplace. You can have, there's a bunch of apps, apps, uh, and Stripe users can click, um, and, like, search for the apps they want to do, and then I click install. Um, so that's how I got the first customers. I actually didn't even go out and find them. Um, I just listed in the App Marketplace, and a few people, uh, downloaded from there, and I kept getting about five to 10 people a week just organically searching up for the, for that kind of e-commerce App and we would show up and then they will install and start getting used.

AI assessment note: “I just listed in the App Marketplace, and a few people, uh, downloaded from there”

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Q A hundred percent. Do you have a story of a client that maybe is fun to share? They're really hard to close or convinced that digital marketing would be helpful at all. Then you blew it out of the water with them, uh, or just you like working with it. What's like your favorite customer story?

A Um, I mean, I could give you the, I, I do like one story and it kind of Tells the story of the start to finish of my business, like from inception all the way to getting ready to sell the business, um, because it was such a long journey. So, um, there was one medical group that I was chasing. It was my, my white whale for years. And so, um, just trying to get in the door, it took me about two years to get in front of the right people. So it was a lot of reaching out to my contacts, Cold calling. Heading into their offices. Trying to work with office managers. You know, I was really, um, I honestly don't know what came over me, but I was so deadlocked on this particular group. I wanted to, to do business with them. And so I just, I went nuts trying to get in. So it took me about two years to get the first meeting set. And that was just with one of the doctors. Then the doctor kind of recommended me up to, um, to some of the executive level team. And then a third meeting with the CEO. So all of that in itself took probably another year. Um, we went back and forth, and even after those initial meetings, probably another year of negotiation, discussion, really going through the ringer, figuring out what makes sense for them, building relationships. Everything you would do with a client, I was doing without them being an actual client, just because I wanted to bring them on board. U…

AI assessment note: “there was one medical group that I was chasing. It was my, my white whale”

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Q What was the reason that, Made you want to sell the business?

A So there's a few factors. Um, I'll start with the big one. Um, the biggest factor, which again, another conversation for another, um, podcast, I'm sure, but, uh, had some family health issues going on, and so my focus wasn't quite there, um, as it had been previously. So I had other responsibilities, um, to take care of, but, um, part of that was I could not Continue to grow the business myself. And so I really had two options. One was bring on more help, more staff, team. Um, you know, I had a very lean operation going and I liked that because it allowed me to be involved. It allowed, um, you know, customer stickiness to be high. Um, but once I was pulled away a little bit, it caused a bit of a bottleneck with what we were doing. So it was either bring on more team. Or, um, or so, and those are the two options, and I had to take the emotion out of all of it, and I looked at the numbers, and the reality was, if I brought on more team, more staff, then I was either going to just obviously lose money myself out of my paycheck, because it'd be going towards other people, and to make up for that lost dollar amount, I would have to grow pretty significantly, um, Because of the way that I had things structured, and it just wasn't worth the, um, the time, the energy, and I didn't have the capacity to be able to do that at that point in time. So, like I said, taking the emotion out of …

AI assessment note: “had some family health issues going on, and so my focus wasn't quite there”

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Q Makes a lot of sense. You know, I work with a ton of people that sell businesses for, for different reasons. I think You know, the more you can be honest with yourself, typically the, the better outcome you're going to have. Um, tell me, how did the process go with Acquire.com? How did that, um, help you maximize your exit?

A So, the best thing about Acquire, uh, and the way that you guys structure things, because I was pleasantly surprised by this, I wasn't expecting it, um, and I needed it, quite frankly, was, for lack of better terms, uh, the handholding. You know, the support that I got from, uh, Kai is who I worked with the most, and he was fantastic through the entire process. Um, helping me work directly with, uh, prospective buyers. Helping me through the, um, the diligence, the paperwork, um, just listening to some of my ups and downs and being, um, you know, lending his ear to A lot of the struggle, because this was, um, it was a lot more difficult to process than I thought that it would be, quite frankly. You know, I ended up getting a couple of offers. They were good offers. They're, you know, what I expected. So it wasn't like I was being lowballed, or like I was, you know, going through something I didn't want to. It was all kind of right in the wheelhouse of what I was looking for, and, um, I still was beating myself up over right decision, wrong decision, you know, how I was going to do all this, and he was super helpful, and just not telling me what to do, not guiding me, but just being a resource, and giving me what I needed, and that made the process so much simpler, because I could focus on what was important for me, and I knew that Kai and the rest of the team would take care of…

AI assessment note: “the support that I got from, uh, Kai is who I worked with”

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Q That is awesome to hear. Yeah. Kai is great. And I remember your, your acquisition specifically, you had a few bumps in the road that were unexpected. What would you say the most stressful part of the acquisition journey was for you?

A Uh, so twofold. Um, and it really comes down to one, one big thing, but you know, Back and forth trying to figure out, um, what I wanted financially at the end of the day. Uh, obviously you're selling a business. Finances are huge with that. And so figuring out exactly how I wanted it structured, what was important to me, um, you know, that took some time to really iron that out. And Kai helped me out and we figured it out. And, um, when I got the LOI, um, for the, from the buyers that ended up purchasing the business, uh, Checked every box, right? We got the upfront that I was looking for. Terms were great. Like we, everybody was happy. Um, and as you know, and you were alluding to before, the biggest issue that popped up was in the 23rd hour, um, the financial company that was going to be fronting the loan for the buyer backed out of the deal. And so we went from everybody's ready to go The next day, um, you know, we had escrow set up. We were ready to roll, and now there's no financing anymore, and so the buyer was scrambling. I was scrambling. The deal almost fell apart because, um, you know, it, it just, it wasn't what we had signed up for on either side, and we were all frustrated with it. You, you were as well. I know Kai was. I mean, it was, it was a bit of a mess, um, and through no fault of anybody's, um, And so it was extremely frustrating. And at the end of the day,…

AI assessment note: “the financial company that was going to be fronting the loan for the buyer backed out”

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Q you know, very straightforward, very direct, very honest with the health of the business. And buyers appreciate that too. Um, so again, kudos to you on that. I guess my next question would be, now that you've successfully sold your business, you've been through an acquisition with ups and downs, do you go back in time and give yourself three pieces of advice? What do you think those would be?

A Ooh, three pieces of advice. All right. Um, number one, and I kind of knew this before, but I would make sure I reiterate it, and it's just like, I mean, it's like sales in any regard, but, um, A deal's not done until it's done, right? Like, I mean, like I said, we were all good and ready to grow, go. Escrow was set. I was counting on that wire transfer a little too much. And when it didn't happen that day, it was, it was a blow. And, um, you know, we had gotten 99% of the way there. And again, by, um, circumstances outside of our control, that's just kind of what happened. And so just reminding myself that Hey, it's not done. It's all it's done. I think that that's super important. Um, number two, I think something I was a little slow to was figuring out the structure of the deal that I wanted and being honest with myself about it because I wanted it to be attractive to buyers. Um, so I wanted it to be flexible and I was genuinely open-minded into the deal, but at the same time, I wish I would have put some parameters on it For myself, you know, I, a minimum of X amounts, um, up front. Here's my maximum length term on seller financing. You know, I wish I would have been a little clearer with what I actually wanted because, um, I wasn't 100% sure. If I probably examined it a little more thoroughly, maybe if I had another conversation or two with Kai about it, he could have help…

AI assessment note: “Ooh, three pieces of advice. All right. Um, number one”

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Q for like attorneys and stuff. They don't need mobile apps. Um, but hey, we'll, we'll happily make them. Um, all right, let's move to the point where you got, um, you know, your own software platform. Uh, tell me about the initial build for that. How long did it take? What like features did it have to have? What was like the big differentiator? I think I know the answer.

A Well, first it just started off with like replicating the features that our customers were using on, uh, essentially like on your platform. Right. Um, so that, that was like kind of step one, then we can migrate them off. And then once we had that, then we could kind of expand the feature set and kind of like V one of the platform was, was just truly that. It's like, how do we just replicate what you have? And then we had V two of the platform where we kind of created like a different architecture where it was like much more modular, um, kind of like the WordPress of mobile app for, You could have these, you know, each, each feature in the app was like a modular unit of functionality. You kind of pick and choose from like Lego pieces for your app. Um, and then maybe to see customize and add additional ones. Um, but I think like V one of our platform probably took us almost a year to build. Um, and then like, as you guys are adding more features, like we had to kind of catch up to those as well.

AI assessment note: “V one of our platform probably took us almost a year to build.”

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Q Nice. So things are, things are going well. You have customers, product market fit. What made you want to sell the business?

A Um, I mean, I, I forget exactly the year, but, um, a few years ago, I considered selling the business, um, because I was considering, um, raising money for the job searching tool, um, and thought, like, I can't be running two product lines at the same time, so I priced it way too high, did not get enough interest, um, but then this time around, I decided to Um, legitimately sell the business, um, for a bunch of reasons. Like, personally, I just had a child, so that is just, like, a big personal change and tough to deal with the stress and the long hours, and, um, I just felt like as I was, um, I mean, he's six months old as of this weekend, but, like, in the early days of having a child, it, it sucks that you're thinking about As you're holding in, like, all the crap that you have to code up, or, like, all the emails that you have to write, and it just, like, doesn't, doesn't feel right, um, and I had been running it for a while, like, it was, I was about six years in, um, the, the job search product that I'd been working on, um, had basically, like, the business fundamentals of the, of the product changed, um, and so I was, Just ready for, like, a new start. I'd also just moved to Atlanta, so a lot of reasons, um, but the, the mock interviewing tool especially was like a, a healthy, multi-year, profitable business that I knew I could get a good return on and find the right par…

AI assessment note: “personally, I just had a child, so that is just, like, a big personal change”

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Q Yeah, yeah, kids, kids are hard. It's a, it's a full-time job is, is how I like to think of it. Um, tell me about your experience with acquisitions. Had you ever sold a company before? Was this your first Time going through a formal process?

A Um, yeah, this was my first time doing it. Um, I actually really enjoyed the process, like, a lot more than I thought I would. Um, it's, I mean, I, I definitely enjoyed it because of Acquire.com. If I was just, like, going out, cold emailing people or something like that, it would not have been a fun process, but the fact that potential buyers were just, like, coming to my door every day and having a bunch of meetings, um, Yeah, just meeting a lot of people, um, it's flattering when a lot of people want to buy the thing that you worked on for so long, um, trying to understand people's motives, and why they want to buy this thing, and like, what kind of wacky deal terms they might try to come up with to screw you over, um, negotiating with them, um, but acquire.com is great, it's just, yeah, it's, It's a time. I think if it had, you know, fallen through, then I might not have liked it.

AI assessment note: “yeah, this was my first time doing it. Um, I actually really enjoyed the process”

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Q Emily? How did she help you through the acquisition process?

A Um, she helped me a lot of ways. So, um, she helped me, we met in the beginning, like, probably every week, um, figuring out How to write up the, you know, the public facing blurb to not give too much away, but make it intriguing enough, um, figuring out how to price it. Um, there, there's also a point when you're in an acquisition process where you have a bunch of people interested, but no one's going to jump until someone else jumps and like gives you an offer or like there's some deadline. Um, so she helped me figure out how to get over that hump. Um, And how to set a deadline, and how to push everyone to the deadline, and, um, for the, um, for the diligence process, which is probably the scariest part for the person selling the business, um, figuring out what documents we need, like, how to structure the diligence process to not have this thing fall through, um, and then transitioning everything over is a surprisingly big lift to, like, Move all the SaaS apps over and onboard the tech team and tell all the customers and meet with all the customers. Yeah, it's a lot, but she was really helpful.

AI assessment note: “she helped me a lot of ways. So, um, she helped me, we met”

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Q Nice. How'd you get your first customers or your first users?

A Uh, so I think the first few came from Reddit. I was building this. I shared it on a few Reddit communities, and because it was an open source product, I wasn't really monetizing it because it was kind of easy to get a little bit of traction in the beginning. Uh, people saw it as an open source product, and they just commented, voted, and people started Uh, sharing ideas on, on GitHub. And that was kind of when I decided to make it like the stuff that I mentioned, so people can easily sign up instead of having to install it on the servers and so on. But like the first few users, like three, because at this stage I wasn't charging anyone, was basically Reddit.

AI assessment note: “so I think the first few came from Reddit. I was building this. I shared it”

Answered produced feed D 5 · C 5 · P 4 · Cm 4 4.60

Q me. So I want to know, um, a little bit more about, we're going to back up a little bit in terms of, uh, you know, Matt from our M&A advisory team. Can you tell me a little bit more? How much did he help you? What specifically did he tell you that was maybe surprising or was there anything you did where you felt was instrumental to getting acquired?

A Um, yeah, I think, um, I think just generally having an advisor by your side, uh, it just helps you to feel more, uh, safe or secure, um, about going through this whole process, because obviously there are some things you don't know how to handle, and well, you can use trapgpt to ask for it, uh, which I also did. Uh, but you know, just having a person who understands the process, um, by your side, it's, it's really helpful. So I think there were two, um, two major, uh, infliction points where I needed mapped out. First one was the listing. And obviously you're wondering, I had this idea, oh, I'm gonna make the listing really, really, you know, I'm not gonna Put too many materials to the listing, and then, you know, kind of make it, if you want to know more, just reach out and, you know, I'm gonna share more info about our company. And, um, Matt said, well, that's, that's not the way to do it.

AI assessment note: “First one was the listing... And, um, Matt said, well, that's, that's not the way”

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Q there's clearly ones where maybe there's none at all, and that's probably the ones that you don't want to acquire. Moving over towards the founder side, I think this is a good segue. You look at a lot of businesses. You look at a lot of different SaaS startups. What are some common mistakes you think founders make when they go to sell their business? Could be evaluation, could be.

A Yeah, yeah, and I, and I think valuation is the biggest mistake. Um, in a sense, I think that, I think that the, It's an acquisition where the seller gets a fair price for their work, but where the buyer can make money without needing to be heroic about it. I saw recently a business where the founder wanted to sell. He had clearly mismanaged the business, like not really taking, he was not really taking care of the business, but he was asking for a very high multiple. Because he thought, oh, if, if, if you work on it, revenue will grow, but he hadn't really built any strong foundation, like, like a long-term foundation, and I was like, yeah, but if I do all that work, I'm taking the risk, I'm doing the work, and in a way, yeah, I, I need all that to work in order for me to be able to make any money, and I think that it's, for me, That's a problem because it means that my margin of safety is zero, and that's bad. You need to have, to allow for some margin of safety. I mean, if you have the best business in the world, sure, like if you have a, and I, you know, a business with super low retention, like super high MRR, and you have lots of private equity firms that are bidding for it, or you have a strategic that is knocking at your door. Sure, that business, sell it for as high as you can and go to a beach afterwards, but I would say for a regular bootstrap SaaS that has competiti…

AI assessment note: “valuation is the biggest mistake”

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