Startup Acquisitions Stories w/ Brian Casel – Founder of ZipMessage

Brian is serial entrepreneur who has founded multiples SaaS startups and have sold five of his businesses in the span of 8 months. With most of them, Brian found the right buyer on Acquire. He’s now focused on his main SaaS startup called ZipMessage.

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Transcription:

Andrew Gazdecki:
All right. I’m here with Brian Casel. I’ve been super excited for this podcast, because I think Brian holds the record for most companies sold on Acquire. So Brian, thanks for joining me on the podcast.

Brian Casel:
Andrew, I’m excited to talk to you. I’ve been a fan of what you’ve been doing and obviously a fan of Acquire, especially these last few months. So yeah. Good to connect.

Andrew Gazdecki:
I appreciate that. Well, to kick things off, I’m sure everyone’s wondering, tell me about the products that you sold and how long of a timeline was it? All at once? Was it over a period of like a year or?

Brian Casel:
Yeah, so I guess sort of the headline is that I did sell or let go of five, you can call them businesses. Some of them are just really tiny projects, but some of them were actual businesses of mine. I let go of five of those over the last six months. And so right now I’m focusing on a business that I started about a year and a half ago called ZipMessage. Once I sold the biggest one of my businesses, which was called Audience Ops, and then I sold a few more, that sort of was the momentum to push me into just focus on this one, SaaS business ZipMessage now. And that’s the focus going forward. But Audience Ops was sort of, for me the bigger one, because that was a business that I was working on for about seven years. And I sold that in September of 2021.
And I did list that on Acquire, had a good experience there and had a really good offer there. But I was also like simultaneously on that one. I was talking to a few other people that I knew and I ended up selling it to someone not through Acquire, but that was, Acquire definitely played a big part of how that deal came together. And then the other one that I sold was a SaaS product called ProcessKit. Put that up on Acquire, had one offer ended up falling through, and then another one came around a couple months later. So that was a really surprisingly fast and easy process through Acquire. Two more like tiny ones. These were both like SaaS ideas that I started at one point or another. And I built it, launched it had a couple of customers, but I didn’t really follow through. I was sort of distracted with some of these other things in my portfolio.
So these two little ones, one was called Sunrise KPI, it was like a little analytics tool. The other one was called Thready, which was like a Twitter threading app. I had not touched those for over a year or two on each one. And so I was just like, let me just throw these up on Acquire just see what happens. And I was able to find two tiny exits on those. And then the last one, the most recent one was a course and community and like content site called Productize. My previous business was a productized service business. So I built a course and a whole community around productized services. But since I’m more into SaaS now and I’m not as in doing the whole course content thing anymore, I ended up selling that one to a friend of mine who was a long time member of that community, Sam Shepler. With that exit, which happened about a month ago, that’s it. That’s all have left. Now it’s just ZipMessage and some podcasting.

Andrew Gazdecki:
I was about to ask, I was like, do you have any more? Like geez. But I love how I meet with a lot of founders that just have so many side projects and it’s like, just focus on one maybe or, I mean, a good strategy is you have all these side projects and then one really starts emerging as the one that probably has, deserves the majority of your focus. So that’s awesome you’re able to sell all those.

Brian Casel:
Yeah. I mean, I think in my experience, where I am now, I’ve come to a point where I really, it feels good to focus on one thing. Because ZipMessage has more faster traction than other things that I’ve started especially in the SaaS space. So that feels good and I just really like to focus now. But I had this whole portfolio of other businesses, but it wasn’t like I started them all at the same time. I mean, but that Productize course business I started back in 2014, the Audience Ops business, I started in 2015, ProcessKit I started in 2017, I think. And so a lot of these things were like, I worked on them for like a year or two, pretty hard. And then I let them sort of run on autopilot or like in the case of Audience Ops, I had built up a team on that. And it was basically running without me and the goal there was to have a cashflow of business to grow and then free up my time to start working on SaaS products.
But then it took a while of experimenting with several SaaS ideas. And also for me to spend that time learning to upgrading my skills from front end to be able to build design products, full stack. Took me a few attempts to sort of get to now, which is like landing on ZipMessage a product that seems to be clicking better than the previous on. It gave me more confidence to finally say, “Okay, lets be sell off everything else and really just focus.”

Andrew Gazdecki:
Yeah. I mean, sometimes you got to get wrong gate to get it right.

Brian Casel:
Yep.

Andrew Gazdecki:
What is, you said zip liner, right? What does zip liner do?

Brian Casel:
ZipMessage.

Andrew Gazdecki:
ZipMessage. Sorry. You’re rattling off so many companies I’m-

Brian Casel:
I know.

Andrew Gazdecki:
…merging them in my head.

Brian Casel:
Yeah. ZipMessage it’s a video messaging tool for asynchronous conversations with anyone. So you can just send your ZipMessage link to anyone and now you’re in a asynchronous back and forth with that person. So the person could be a customer, a client, a remote teammate, even some of these deals that I was going back and forth during due diligence. We did that over ZipMessage asynchronously. So, it’s pretty similar to like using Loom except the difference is Loom is like one way, you would record a message and send it to someone and then it’s basically done. With ZipMessage, you can send a message that the other person can reply back and they don’t need to download or install or sign up for anything. They can just record right into their browser.

Andrew Gazdecki:
Nice.

Brian Casel:
And the other sort of difference is you get your own ZipMessage link. So, you can get like zipmessage.com/Acquire. And then that could be the place where people, that’s like your inbound intake for video messages from other people. So I like to think of it like, so if you’re doing like a lot of calendar bookings, a lot of meetings, you could start to replace those with async videos, but also like how you would pass around your calendar booking link, you could pass around your ZipMessage link to have asynchronous messaging going.

Andrew Gazdecki:
I like that. Well, if I see you come through Acquire, I’m going to reject it just so you can stay focused on this. It sounds like good one.

Brian Casel:
Yeah. Not for sale.

Andrew Gazdecki:
So, for people listening a lot of founders as, usually in almost all cases, it’s the first business they’re selling. What’s maybe the top three tips you would give a new founder looking to sell their business on Acquire.

Brian Casel:
Yeah. I mean the first one that I ever sold was back in 2015 and I worked with a broker on that to sell of the business. And I mean, overall, that was a pretty good experience, but it wasn’t cheap. So that was one of the big, exciting points for me when Acquire came about it was sort of a way to access buyers and get deals happening without, especially at this level. If you’re in the hundreds of thousands of dollars, like that’s a really significant broker fee that you would normally pay to a broker. It might make more sense when you’re in the upper millions, but at this stage that was really exciting. But anyway, going back to my first experience selling it was one of the things that I learned early on with that was, my first time selling, I thought that I had to make the business look perfect and pristine for the buyer. Otherwise buyers wouldn’t be interested in it.
And that’s actually pretty you wrong. I think the way to think about it is, just show your business whats and all like, it’s okay if there are gaps, it’s okay if things are not under optimized. Because that’s the opportunity that a buyer is looking for. If you’re a buyer, you’re looking to buy a business that you can come in and improve and grow. If you’re going to buy a business that’s just running perfectly. It’s going to be very difficult for that buyer to come in and grow it. So, don’t feel like, yes, you need to like clean up your books and have processes that make it ready to hand off to a buyer. But I learned to not stress over all the things that are like missing or the gaps in the business. That helped a lot.

Andrew Gazdecki:
Yeah. Sometimes that actually I’ve heard from a number of buyers is they’ll actually look for businesses like, and I don’t recommend this, but like poor website design. If they’re a experienced marketer, they can improve like free trial to paid conversions or something like that. And that’s a huge selling point. Or maybe you don’t have to point it out, but as a buyer, you see that. And you’re like, if I can just tweak like 10% and this business will increase. So I totally agree with you on that.

Brian Casel:
Yeah.

Andrew Gazdecki:
In terms of like negotiating with buyers, again, you’re kind of a veteran here. So, what are like some qualification questions that you usually ask buyers when they are interested in buying a business from you?

Brian Casel:
Well, I mean, this is an area where I think a broker does add value. In the cases where I sold on my own, you do have to do your own well vetting, but also you’re just kind of sifting through some noise of buyers who are just not as serious or they’re kicking the tires or they say they’re serious, but they’re really not. So if you’re working with a broker, they tend to kind of shield you from that. And they do a lot of that vet for you, but it comes at a cost. So there’s a trade off there. One of the first questions that I tend to ask a potential buyer. If they’re a stranger to me, I don’t know them would be to just ask, “Have you Acquire businesses before” not to say I would rule out selling to someone who has never Acquired something before, but if they have never Acquired something before that is an indication that they are not as experienced and serious in this process as others who have Acquired something before.
And if they haven’t, then maybe the next question would be, “How many other businesses have you been talking to about acquiring? And how long have you been looking?” Because the other thing that I’ve noticed about, again, going through several deals now in my career and several recently is that there’s a pretty wide spectrum in terms how these deals happen. One of them took three months from offer to close. Another one took five days from offer to closed like literally. And so some people are just like kind of crazy and stressful when it comes to due diligence and others are, they just value speed and no BS, just let’s do this. And again, that’s not to say you should be careless or you shouldn’t overlook things, obviously in a deal that’s any significant dollar out. You do want to do your due diligence, but some people want to play more games than others when it comes to contract negotiations and others just want to be more straightforward about it. And yeah, it’s just kind of all over the map.
And so the more experienced the person is, it’s a little bit tricky because it’s sort of a two way street on the one hand, somebody who’s more experienced has done more acquisitions in the past. They know the mechanics, they know the process, there’s, they’re going to ask for certain things and then they’re going to do due diligence. Then we get into contract negotiations and a wire transfer or whatever it may be, or like they, they’re not new to this. So, that makes it easier but then on the flip side, they might be more savvy. They might be a little bit more aggressive in the tactics that they use. So like they’ll sometimes they’ll use time to sort of grind you down. Like drag it on intentionally because as the seller, I know for me, most sellers want to get a, it done faster if possible. I’m working on a new business. I don’t want to be bogged down with selling this one.
Sometimes they’ll use that sort of thing against you. They’ll use, they’ll pull at your emotions, once you start down the process, it you’re mentally already selling the business, but it’s not actually done yet. So there’s a lot of little games that can be played throughout the process. And I’ve just, I don’t know what I’m doing most of the time, but it’s mostly legit just kind of trusting the gut and getting good advice from friends and advisors who’ve been through this sort of thing before. That helps a lot too.

Andrew Gazdecki:
Nice. And I really like that. And really what you’re doing is you’re making the buyer work to really get through your filter with just these simple questions. Like, have you Acquired a business? And if they don’t respond or they do respond, you ask them another question. And then they respond or they don’t respond. Other good questions could be like how if we get to the finish line, how would you finance this? Like just getting those questions kind of upfront could be, let’s say both parties a lot of time.

Brian Casel:
Yeah, for sure. I mean, I also did want to ask a lot about, like, tell me about your current business? Tell me about your background. What does your current team look like? And things like that just to get a good feel for it.

Andrew Gazdecki:
Yeah. And then I guess another question I would have is, so you’re getting ready to list on Acquire. Was there any materials that you prepared in advance or anything you’d recommend sellers kind of think about in advance?

Brian Casel:
Yeah, I did a bunch so, I had sold a business before, like years before, so I’ve been through a due diligence process before, so I knew the kind of work that goes into just preparing for that. On the larger deals that I did, lot of the due diligence work, like getting my books in order getting, just getting to the things that I know that they’re probably going to ask for. Doing a lot of that prep work, even before I listed helped a lot. So that by the time it got into a deal, there was very minimal time and prep work that I had to do.
I did create a very simple, I guess you can call it like a prospectus, it’s like a PDF with some, or it’s like a slide deck, I don’t know, five or six pages or something like that with kind of the big selling points, if you will. But, not the level that you would see in due diligence, but just like the high level numbers of revenue and like net profit and traffic and some of the key elements of the business and why it works and things like that. Something to show potential buyers. What I think of that document, it’s like something to show them, give them enough information that makes it interesting, but also makes them want to actually book a call with me and ask me more questions about the business and get to a point where they’re comfortable in enough to submit an offer.
You can’t expect just the listing page or just the asking price or just the name or something to be enough for a buyer to submit an offer. They’re going to need to, first of all, they’re probably looking at many other businesses, second of all, but you don’t want to give all the information up front, you want to sort of pull them in. If they’re interested in where this is going, let’s have a conversation and then let’s get to an offer if there’s one here.

Andrew Gazdecki:
Nice. I really like that. I guess another question I would have is there any part of your sales that you would do differently? Like now that you’ve kind of, you can roll back the tape and maybe like, oh, I wish I did that differently or any sort of like-

Brian Casel:
You asked a little bit earlier about like vetting the buyers. I think there were a few, like not the people who ended up buying the businesses, but I did have some offers and some inquiries and calls and follow ups with people who turned out to be probably less serious than they led on. And I probably could have done more to vet them. Not so actually sure what I else I would’ve done other than asking those questions, but looking back, there was one who actually did make an offer and we started down the road of due diligence, and then they ended up backing out for some random reason midway through. And two other people they would keep coming back to me every three days saying, “I’m about to send you an offer just about to send you an offer” and then nothing. But in the meantime, somebody else came along with a real offer. So that worked out.
So yeah, when you’re going in alone and you’re in a marketplace, like Acquire and I did supplement with other contacts that I have in the industry. So I was sort of mixing conversations from different places. Without a broker you’re sort of on your own. But that’s by design, right? I chose to go without a broker in intentionally because basically because Acquire exists that made this path a lot more viable, but it is more work and sometimes a little bit more like just dealing with a lot of noise before you get to. But that’s not to say that, there are definitely very real and serious and high quality buyers on the network. I met a lot of them. So they’re there it’s just there’s a mix.

Andrew Gazdecki:
That’s awesome. But I know we getting into the 30 minute marks, so I have three more questions for you that are, questions I just like to ask every person I interview. Well, just favorite book that you may have read in the last year?

Brian Casel:
I’m always terrible with these like rapid fires. The one that I’m reading recently is pretty good, “The Cold Start Problem” What’s his name? Andrew Chen.

Andrew Gazdecki:
Andrew Chen, The Cold Start.

Brian Casel:
Yes. Halfway through that. It’s really applicable to what I’m building now with ZipMessage, because it’s how to build on a network and use the freemium model and all that. So it’s been pretty good.

Andrew Gazdecki:
Nice. Who’s one entrepreneur that you really look up to?

Brian Casel:
This guy, Andrew Gazdecki, pretty impressive dude.

Andrew Gazdecki:
You need a better one, man.

Brian Casel:
Let’s see. I mean, I’m close friends with a bunch of founders who I talked to. I just hung out with a bunch of them last week we went snowboarding and talking business. We do that every year. So I just get a lot of value and inspiration from a whole group of close friends and advisors, and it’s kind of like a mastermind group, but we’ve been meeting up and going on these snowboard trips every year for like the last eight or nine years and that’s just been super helpful. So in general, I always recommend trying to find like a core group of mastermind buddies to hang out with.

Andrew Gazdecki:
Nice. Well, that’s pretty all I got for you. I really appreciate you taking the time on this podcast and congrats on selling all the businesses. When you sent me that email, I was like, are you serious? Like what I got to hear this story. But Brian, congrats on all your success, man. I’m rooting for you and your new company. If people want to get a hold of you, what’s the best way to contact you?

Brian Casel:
Yeah. Well, you can definitely get to me and check out the tool at zipmessage.com. I’m basically running the support desk over there right now.

Andrew Gazdecki:
I feel like we should integrate that like into Acquire. That would be like a perfect, we can check at afterwards, but it seems like-

Brian Casel:
Totally.

Andrew Gazdecki:
… a good use case in terms of like, here’s the answer to your questions and da da da.

Brian Casel:
Definitely. I mean, I literally did use it in a lot of the conversations and it is perfect for that because it’s easy to go back and forth with somebody who is like a link away. They’re not within a private slack workspace or something like that. It’s easy to share with anyone. So yeah, I would love to talk about that. So yeah, you could even send me a ZipMessage at zipmessage.com/brian that’s my link. And then I’m on Twitter @CasJam.

Andrew Gazdecki:
Well, Brian, thanks again for making the time and you hold the record for most companies sold on Acquire. If that ever gets broken, I’ll be sure to let you know.

Brian Casel:
Good stuff. Thanks.

Andrew Gazdecki:
Cheers, man.