How To Achieve Entrepreneurship Through Acquisition With Will Smith

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Table Of Contents

In this episode, Mike Gardon chats with Will Smith. Will founded Acquiring Minds in 2021 shortly after discovering acquisition entrepreneurship, a love-at-first-sight moment. Prior to Acquiring Minds, Will ran partnerships & business development at two SaaS companies in the Bay Area. Earlier in his career he founded multiple online businesses, some of which were acquired, some of which continue to thrive.


  • Will’s background
  • Acquisition entrepreneurship - what is it, how someone can get started
  • How Will’s time in South America shaped him and his direction
  • How Will went from startup to employee back to startup and what he learned through all of those directionals
  • How taking risks in work/business at a young age can pay off
  • Why Will chose to start a podcast


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  • Acquisition entrepreneurship: is the idea of buying an existing business and becoming the entrepreneur owner of that business.
  • SBA loan - one way that an individual can get into buying a business
  • Acquiring a business can create options for you. It can start as a side hustle or a second form of income.
  • Tips on how to invest in yourself
  • Indie Hackers - a site Will references
  • BizBuySell - a popular place where businesses are sold
  • Flippa - a place to buy websites and online businesses
  • Connect with Will on his website, Twitter, LinkedIn or his podcast.


Disclaimer: The transcript that follows has been generated using artificial intelligence. We strive to be as accurate as possible, but minor errors and slightly off timestamps may be present due to platform differences.

Mike Gardon (00:00):

Hi everyone. And welcome back to another episode of CareerCloud Radio. I'm your host Michael Gardon. I'm on a mission to help people build thriving work lives and in truth, there's never been a better time to control your destiny. The key is to understand your options and get intentional to help you along the way. I try to have interesting conversations with people that approach the idea of work a bit differently. And hopefully these conversations open up your eyes to the infinite options that there are to earn a living fine purpose, happiness and balance today's guest is Will Smith. No, not the Will Smith, but close. Will is a serial entrepreneur since his dorm room college days. And he is now a podcast host of Acquiring Minds, a podcast aimed at helping people achieve the entrepreneurship and freedom through the acquisition of existing small businesses.

Mike Gardon (00:48):

I was lucky enough to be one of Will's first guests and share my story of acquiring CareerCloud and other web-based businesses and taking that portfolio from side hustle to full-time since then Will, and I have shared lots of notes on entrepreneurship, acquisition, and life. So I wanted to bring Will on to share his very unique experience of thinking about career, his experience of living in South America for several years, and going from startup to employee back to startup. And then of course his new passion around entrepreneurship through acquisition, which I believe is an amazing path to putting together a side hustle or breaking free entirely from corporate strangle holds, holds to find your inner creativity piece and balance. I hope you enjoy this episode with my friend Will Smith. Will welcome to the podcast. How are you today?

Will Smith (01:34):

I'm doing great. Thanks for having me look forward to this conversation.

Mike Gardon (01:38):

Yeah, I'm uh, really excited to have you on the show for the audience. Listening Will host a podcast. I happened to be on his podcast, uh, when he was just starting out. He, uh, saw an article that I think was written about me on, I believe it was Starter Story about how I actually acquired this business and a couple other businesses and reached out and wanted to talk about it because his podcast is all about acquisition entrepreneurship, and that may be a new term for our audience. And so as I'm kind of talking and bringing on guests to broaden our horizons about what we can do with our careers, this was a really interesting topic, cuz it's something that I've done. It's something that, uh, Will has now interviewed a whole bunch of people on. And so I'm gonna start to today Will with asking you if you could just define that term for our audience and then we'll kind of go from there.

Will Smith (02:29):

Cool. Yeah, I'm thrilled too. And thanks again for having me Mike, on, on career cloud, this is gonna be a fun conversation. So acquisition entrepreneurship is the idea of buying an existing business and becoming the entrepreneur owner of that business in, in brief. And the benefits of it are that you are buying an existing enterprise. So something that already has customers and, and a team and profit. And so one way that you'll hear people refer to it in a kind of pithy way is you're buying a ringing phone and any entrepreneur knows that even if you have a great product, even if you have a great team, it just takes time, often years to build that ringing phone or the traffic that's going to your website. And so this is something of a shortcut to a business where there's already traffic to the website and a phone that rings.

Will Smith (03:18):

And then there are a few other pieces to this that are really important. The first is that before I got into this, I just thought that buying a business was something that just private equity people did or an already rich person did, or you know, company a does a company B, but it turns out that in the us, we're really fortunate with the SBA program. And so that you can take an SBA loan of up to 5 million and acquire an existing business with 90% of that money loan to you by the S SBA. I won't get into all the mechanics of it. It's not that complicated, but we'll just breeze through it here. But the point is you don't need to buy a business outright. If you can come up with 10, 20% of the enterprise value of the business, this to say, buy a million dollar business.

Will Smith (04:01):

If you can come up with a hundred thousand dollars, you can finance the rest of that and pay down that loan with the profits of the business itself. So this is something that in the eighties, people heard about a leveraged buyout that was done at the corporate level. You know, multi-million billion dollar transactions. Well, this is a version of the, that that an individual can do. And if you've never heard of this, and this is the first time you're hearing me talking about it the first time you're hearing of it, it might sound complex, weird, like something that I don't know unrealistic. But in fact, as I've learned from talking to so many dozens of people who are doing this, it's very doable. It is a really cool path on entrepreneurship. And the only other thing I'd say Mike about acquisition entrepreneurship is that this is a good time to be doing it because there's this generation of people, baby boomers who have built the small businesses across America and are now looking to exit those businesses cuz they wanna retire. So there are projections of these small businesses coming to market, coming for sale in a swell that that is gonna be really quite large. And so there's gonna be a lot of opportunities for acquisition entrepreneurship. I could say more, but I'll I'll stop there.

Mike Gardon (05:09):

Yeah, well I, you obviously have content for an entire podcast on the topic. I know you can talk about this, uh, all day and for weeks and months on end, which is fantastic. But again, the reason why I wanted to bring this convers to our audience is it's not just thinking about acquiring a large business. There are all sorts of sites and there are all sorts of people who are acquiring micro businesses and websites and, and you know, I've gone through that process as well for a side hustle or a second income stream while they're working their, their first job or their current job in. And I advocate for a lot of this type of thinking because it makes us more resilient when we have second income streams, third income streams, and we put effort into, as I have done with this business, we put effort into a side hustle and continue to consistently grow it ultimately to the point where it can replace our income as an employee, we've created options for ourselves.

Mike Gardon (06:06):

And so that's why I'm bringing this topic to our audience. So acquisition, entrepreneurship, there's entrepreneurship in terms of creating business for and scratch, you've kind of dabbled in both. You've also worked as an employee for companies. I have a lot of that kinda hodgepodge of, of, uh, slapping together a career in me as well. And so I'd like to kind of from here, go and just ask you to maybe kind of trace your career a little bit. Like where did you start and weave a story through your experiences of, of being an entrepreneur, selling companies, working for companies and then ultimately getting to, uh, what you're doing today?

Will Smith (06:47):

Sure. So I had a side hustle essentially in college, which was a, a, a website in the web hosting space. It was online marketing. This was during, but so early two thousands, late nineties even. And so wasn't called side hustle at the time, but it was a website that generated a few thousand dollars a month, which for a college student was considerable income. Probably even today. I was fortunate that I, I, I didn't have college loans. So this was really money in, in my pocket and, and very powerful. And as you can imagine, after that, I was kind of hooked. So I always wanted to be working more on that business. And, but I was also in college. So classes and partying and, and so on was always conflicting with my interest in, in putting time to this business when it came time to graduate.

Will Smith (07:33):

And I was interviewing with consulting companies and tech companies and so on, but not really feeling coming back from those interviews, not really feeling super motivated to go down into these paths. My then girlfriend was like, well, why don't you work? Do your business full time. And for some reason that hadn't occurred to me that I would just devote myself fully to this business. Well, that got me excited. I mean, that was immediately like, obviously it was higher risk, but it was like, yeah, that sounds like a lot of fun or giving my, giving my whole self to my business. That's what I did right out of college. And I really think that that set a precedent in my career. You know, my first thing out of college, I was working for myself and had I taken one of those consulting jobs or a program or a tech company. I think things would've unfolded very differently.

Mike Gardon (08:13):

Yeah. I popped in with a follow, sorry.

Will Smith (08:14):

Of course, of course.

Mike Gardon (08:15):

There's so much there already that I wanna ask about in college. What were you going after? How did you develop, I guess I'm looking at how, how did you develop an interest in what was going online to even start that business in the first place?

Will Smith (08:30):

So I was studying computer science. I had a job as a programmer at a, at a consulting company over the summer. I had learned to basically put together a website with a database backend. That sounds really fancy, but it's basically how every website operates, but this was in such early days of the web that like doing that was still very powerful. And there was a lot of opportunity. If you could develop a website where there was data on the backend that could send and receive data and, and then display it on the front end. So I won't go through the whole Genesis of the idea, cause it's probably more detail than you need, but in searching around a scratch my own, its for web hosting, because I wanted to put a website online. I saw these businesses, these websites that basically were shopping sites to help you find a web host.

Will Smith (09:11):

So you, you say, I want X, Y, and Z feature and I wanna pay much and I need this much bandwidth search. And then all these web hosts displayed. And I just was interested about that bus. So it was kind of meta. I was, I was like on this web hosting search, this directory of web hosting businesses cause I was looking for web hosting, but then I became interested in that site itself. And I remember basically clicking on the advertising link because these site just were papered with advertised, just like banners all over the place they were clearly doing really well. I knew that web hosting companies were proliferating cuz this was the advent of the web. If you wanted to have a website, which everybody more and more people did, you needed to pay a web hosting company for that. And basically I just triangulated that these web hosting directories were crushing it.

Will Smith (09:53):

And I was like, I could build this with the new skills that I've learned at this consulting company. I could build this, I had the itch to just like put something into the world, just kind of that creative itch. I wasn't actually financially motivated yet. I was still this college kid who like didn't, you know, didn't have to worry too much about money quite yet. But then so it was like, this could be a fun project and these websites seemed to be crushing it, let, let me go after it. And so, and wouldn't it be amazing if I could have like $3,000 a month in college with, and have nothing to spend it on other than whatever, you know, beer and travel or whatever, it was not travel. I was too young for, to be traveling much beer, I guess, $3,000 a month of beer. And I, after, uh, about a couple of years, I, I got there and it was incredibly rewarding. So, and then once I kind of got that taste for online businesses, as I said, I was kind of hooked and then I just got into the world and was reading about it and looking at other websites and I just became very kind of business mind about the web.

Mike Gardon (10:51):

Why do you think it didn't occur to you to just take that and run with it? Why right away, like what was it at your girlfriend kind of yeah. Switched on in your brain that made that a reality. I I'm interested in this because I've had moments in my career where I've been like, it seems like a really simple thing, but a, a switch flips. I'm like, oh, you just kind of see the world in a path and a, in a new light. So I'm just kinda interested in what might have flipped the switch there.

Will Smith (11:18):

I don't know. Maybe because the way I framing in life is so powerful. And maybe because I had always, the way I had had framed this website project to myself was it's hobby it's side hustle. It's beer money. It's not anything more than that. And so just cuz I had had that kind of my own bias that I had just created arbitrarily, I could have been more ambitious about it, but just hadn't been, it didn't occur to me that wow, no, this could be something larger. I remember she wasn't saying it because like she knew anything about the potential of the business itself. She wasn't like, oh the Tam of this could be, you know, you could, there's such a big market here, go after. No, it was just simply, she was observing me not being that interested in these other paths, the interviewing that I was doing for these more conventional pads.

Will Smith (12:05):

And at the same time watching me be frustrated that I could never give as much time to this side hustle business that I had as, as I wanted. And just kind of like put two and two together, you know, it was kinda like, well, why don't you do the thing that turns you on? And it's already making some money, could probably make more if you gave it a hundred percent of your time. So I think it was as simple as that. But I think the insight of your question is like, is that yeah, we should always be questioning and poking at our own framing of things. Because if we think about things differently in our own lives, then probably we can open doors that are arbitrarily closed in our own mind.

Mike Gardon (12:36):

Yeah. I totally agree with that. I mean, it's amazing how over my career and experiences I've seen, like it's just the simplest idea that seeking an outside perspective and it often doesn't need to be like a really smart, believable person in whatever you're doing, but just a shift in perspective can like shine a light on kind of your own self limiters. And we're I think for 97% of us, we're probably the biggest self limiters. The biggest limiters I should say. It's just so interesting that that's what it took is just a girlfriend saying, well, why wouldn't you just seems easy? Like why wouldn't you just try that, uh, yourself to put you on a different path? I mean, that was, that's pretty amazing.

Will Smith (13:20):

It's, it's a great point, Mike and I, and I Will just, I just Will reinforce the point that you just touched on it. I made earlier that like the way I always look back at that is, is how it did set me on a certain path. It's at a precedent in my life. I just think that the, yeah, these moments it's kind of like the Steve jobs thing, you can only connect the dots after the fact. You can't really do it looking forward. But um, I definitely now looking back, connect the dots back to that decision. Like if I had gone on a conventional path, I probably in that moment, I probably would've continued on a conventional path. And so it set me on another path. And so just always, yeah, I guess the takeaway there is always be thinking about a decision in a longer term, like what kind of path might this set you on? Not just immediately, what's gonna happen next month or even next year, but how might this decision impact where you're gonna be in 10 years that could probably freak you out. So don't overdo it, but you just see what I'm saying.

Mike Gardon (14:14):

Yeah. It's maybe it's connect thing. Right. You can get into like the decision tree. Right. And trying to like all of a sudden predict all of these different variables 10 years into the future. But I think I look at it more as like, um, the trunk or the branch of the tree, like is this path setting me on a, a course that's likely to be more aligned with my true self. I think that's where it is. Like you can never predict all of the different, tiny branches. You never can predict where you're gonna end up. But I think when you come to that fork in the road, like which side feels more aligned and, and it's quite often that simple to get put on another,

Will Smith (14:52):

That's a great way to put it one word I like that you hear people use a lot is, is directional. And so I think with these like decisions try to be directionally accurate and true to yourself. You don't need to, you're not gonna be perfectly. You're not gonna be able to map out your future perfectly decision by decision. But as long as you're roughly going in the direction, that feels right. Just keep doing directionally true things and you should be continuing to March in the right direction.

Mike Gardon (15:19):

What was the next directional for you after this?

Will Smith (15:23):

I had wanted to go abroad in college. I didn't. And so I had this other itch to scratch, which was what it was now called being a digital nomad. But I'll tell you, it just wasn't done. This was 2004. And so it was really an adventurous thing to do just anyway. So that business that I had in college had in fact grown, I kind of pivoted it and it wasn't exactly the same thing as it was back in college. I, I, I grew it and changed it a bit, fundamentally the same thing. And in, and in fact it was now supporting me and I wanted to live abroad. It was just something that I had always wanted to do. And so I moved to a, basically I moved to bueno SARS and with a laptop and continued operating the business from there. So that was another, you know, just big directional decision because once I was in Argentina and learning Spanish, I really wanted to learn Spanish.

Will Smith (16:17):

I then became comfortable with 12 months later saying, well, now I wanna try a different place and then moving to Brazil and then moving to Chile. And so I spent a good four years in three or four locations around south America, learning Spanish, learning Portuguese. So I was tri for a while. My Portuguese has since disappeared, but so anyway, but that first decision to go to Argentina, set me on that path. And by the way, now my wife is Chilean. I didn't meet her during my stint in Chile, but I think it's helped that I had lived in her city, in her country and speaker language. I think that that does tie back to our point of like connecting dots and, and doing things that are directionally accurate. I've always liked having a broad internationalist view on things. And I think her, one of the things she likes about me is that her being non-native to the us. So anyway, that decision to go to Argentina, then just set in motion kind of a four year adventure outside of the us.

Mike Gardon (17:17):

Excellent. Which, so you've started a couple businesses. I don't know. I dunno we're at, in the timeline yet, but I'm gonna fast forward a little bit. Cause you've started three and you've essentially sold three. Is that correct?

Will Smith (17:31):


Mike Gardon (17:32):

So get me to that point. I'm interested in kind of this, this guy that went from idea in college dorm, not maybe not a full-time thing to then starting three businesses and, and exiting, what's an exit sort of like for a person like you,

Will Smith (17:48):

This is what I'll say about that. So these exits were not billion dollar exits, but when you are 23 and it's 2003 and the tech industry is tiny compared to what it is now. And there aren't the, the concept of unicorn is still 10 years away, like having sold a business for low figures. So not even hu really not huge sums was a huge feather in my cap, just like professionally. It was a big victory and having let's call it $150,000. Let's say what that's, what it kind of was again, not big numbers by today's standards, but being 23 years old with $150,000 in cash living in south America. Let me tell you, I probably felt more freedom in that moment than a 50 year old billionaire feels, period. I mean, we all know that you need to combine your cent money with time. Like these are the two assets of wealth and we all realize with time, how much more precious time is it's not replaceable money is so being 23 with, okay, not a million dollars, not a billion dollars, but $150,000 in my back pocket living in Argentina.

Will Smith (18:56):

It was just incredibly the, the sense of freedom was just singular. And again, yeah, that I had a computer science degree clearly that was that, you know, I felt like a lot of strength there, professional potential there and then bringing, you know, developing a product, taking it to market and then selling it. You just doing the entire cycle was also, as I said, a victory. So what it felt like was just incredibly exhilarating sense of tailwinds, just the wind at my back. It was awesome. So even though it wasn't big numbers, I feel like I can sometimes relate to some of these incredible exits that you hear about press, because it was really just completely exhilarating at that moment when I was in my early twenties.

Mike Gardon (19:37):

Yeah. Really, really interesting. I mean, there's so much to pick apart there from the standpoint of being young and taking risk. I don't know how you felt about doing entrepreneurship, if you felt like that was a significant risk at the time I'm being so young with your kind of alternatives in terms of going into the workplace. But I think the, you know, I mean the point is I've always thought like take as much risk early in your life as possible because it's harder and harder to take a lot of risk. As you get older and accumulate more responsibilities, spouse, family, you know, what job, whatever it might be. Did that sort of sense of risk analysis come into your mind at all when you were doing it? Or was it just kind of like, no, this is cool. Like I'm confident and I can just go down this path.

Will Smith (20:30):

I think it came into my mind a little bit because people would, would be like, oh wow, dorm room entrepreneur type that kind of motif already was in the culture. So people would be like, oh wow. And I think occasionally people would be like, oh man, so risky or something. I, because I just remember feeling like this is so not risky. I'm young. I can fall back on a job. I have, I'm studying computer science, which is like the safest or, or the most door opening sort of degree you can, you can have, I mean, even more so today, much more. So actually now to be honest with you, I don't know if I thought about all that at the time, I didn't feel like a big risk, but over time, certainly over the subsequent years I realized that it didn't feel like that big a risk.

Will Smith (21:13):

And certainly now I'm 42 now. Oh my God. Like risk. I couldn't agree with you more strongly Mike about like take risk when you're young. I don't know why people think 20 year olds doing crazy things is risk. It's not risky. 40 year olds, 50 year olds doing crazy things is risky, especially if you got a family. So I'm all about people taking big shots when they're young. I Will say this though, because I feel like the hustle culture thing and that you see now where people are just, some people in that world are so hungry and they just devote their twenties is just all, all about getting as far as they can in their careers. So that, I don't know, by the time they can be like done by the time they're 35 or 40. I don't know that for me, that, that would've worked.

Will Smith (21:57):

Like I didn't use my twenties as productively. Uh, according to these, this kinda like hustle culture norms as I could have, although I was pretty productive, I'd say, but I was also doing a lot of that, that you could only do in your twenties, like living in like Buena Saturdays in Santiago, Chile. So I don't know. I think that big risks in your twenties, but also big fun in your twenties, how is, is what I would advocate for most people everybody's different, but that, that felt right to me then. And it continues to feel right to me.

Mike Gardon (22:25):

Yeah. I, I, I tend to agree when I was at the, that point in my career, not career even, you know, it was just, it was college. I mean, I started my career in the financial derivatives trading world and it was really, I mean, I had some proclivities for the markets and finance and stuff like that, but it was really more, the calculus of it makes sense for me to just take a giant shot, but right away when I'm young, because you just, your ability to bounce back is so much greater. So I took this big asymmetric risk. Like I didn't have to put up anything. I wasn't really risking much of anything except maybe my time and my ability to learn someone else was staking me with capital, you know, to, to do that. And I think on my balance worked out, I, I didn't hit a lottery.

Mike Gardon (23:12):

I didn't, I'm not one of these giant hedge fund guys. Right. But like on balance, it worked out better than probably if I would've started on the bottom rung at some company and worked my way up. So I do in everybody that I counsel with and talked to as well, like young people, that's him a number one piece of advice. Like, what does it feel like you wanna do right now? Like stop thinking about it. What does it feel like you wanna do right now? Follow that path first. And then along that path, what's the biggest shot you can take the biggest asymmetric risk reward you can take. That's kind of how I think about it. So that's really interesting that you've just walked down that, that path as well. So I got a couple questions on you kind of went from this culture of entrepreneurship to then working in companies as an employee. How did you think about that transition? What were your goals or what were you after in making that transition? Cause I've done that as well and come back full circle a as have you. And so I'm just curious as to what your kind of psychology and what you were thinking about at that time in your life.

Will Smith (24:19):

Sure. Well, part of it was that I was living in DC where I had co-founded a, another business and I was involved running and involved in that business because of my background in computer science, because of my background in entrepreneurship, I was just watching from afar, Silicon valley happen, and I just had the strong desire to get closer to it. And it took me some years kind of to make that decision because I had the operating business and my business partner and, and family and friends and a life in Washington DC. But eventually I did, I did make the move. And so once I got to San Francisco, it wasn't just about geographically being here. It was also about getting involved in, in the ecosystem here. And so getting a job was obviously a way to do that, but I also thought that I thought that working for a company could actually, there was a lot to learn there because I, I think being the entrepreneur that I had always been, it's a particular skillset, but then working on a team with more people around you having a boss, being an employee, I just thought that there was kind of, I felt like there was something there to learn.

Will Smith (25:25):

I didn't know what exactly. Maybe just being an employee would make me a better entrepreneur, better boss later, later on down the road. So it was kind of like, I felt like I wanted to get closer to tech. And so the, the fastest way to do that would be working at a company. And then also just personally, I thought that there could be a lot of growth by working within the context of a company that wasn't my own. And in fact, I was right about both of those. Uh, it was, it was a way to get involved very quickly into the SA industry. And I really valued my time at Insta page was the company. And I think I did learn a lot, I think by kind of rounded out some of my, the experience of working on a team in a different capacity as an employee and also in a larger team, the business that I had had in DC was a, a tiny company versus Insta page, which also wasn't a big company, but it was 50 people. So that was a lot more than what I was used to. All of these things I think really did, were really educational for me and kind of a, a deep way

Mike Gardon (26:21):

Added to the skillset added to the experience factor. And then you ended up, I don't know if it was right after Insta page, but you, you end up back kind of in the world entrepreneurship. Right. And again, I've done this as well. And so I'm interested in what was the decision like to leave? How did you execute that decision into the kind of the next phase of what you were doing in your life?

Will Smith (26:45):

Yeah, there was actually another company in between Insta page and when I struck out to be an entrepreneur, again, the reason that I did that was because I, I just continued to have the itch. So that, that in between experience of that company was kind of like not a great fit type situation. So I wasn't there very long and I felt that this was now I had kind of in a very quick way, gotten involved in the Silicon valley ecosystem that I had so wanted to be involved in while watching from DC. And then I just got the itch to go back to my roots, cuz I do feel like kind of my personality is entrepreneurial. It feels very, you know, you talk about kind of the trunks. I do feel like directionally, I'm always kind of the natural direction for me is to be doing something entrepreneurial after that, that experience I thought, well now is the, the time to, you know, I I've had gotten some of the experiences that I wanted from being in the startup ecosystem here in San Francisco, in Silicon valley.

Will Smith (27:42):

Now time just to go back to my root, to being an entrepreneur. The challenge for me was that I didn't know exactly what shape that would take. So there are so many different types of entrepreneurs and entrepreneurial energy and why some people and why people become entrepreneurs. There many different reasons. Some people are just, they have an idea and they just need to pursue this idea. It's just, they've got this burning desire and some others just like the, the lifestyle, the independence, the whatever, there, so many different things in this moment, I put myself in the second category. So I didn't have an idea that I was just absolutely possessed by, but I did want to go back to my original and kind of most natural path of being an entrepreneur, but that's child challenging because it's like, well, what precisely are you gonna do?

Will Smith (28:27):

What business are you gonna start? And that's actually what led me. There was some kind of intermediate steps there, but that's what led me to acquisition entrepreneurship and why I'm so excited about it because it's an opportunity to be an entrepreneur, even if you don't have, even if you're not putting people on Mars or doing the next Facebook or, you know, you don't have some unicorn idea that doesn't mean that the entrepreneurs among us don't want to be an entrepreneur. And so anyway, I I'm about to start talking about the benefits of acquisition entrepreneurship again. So I'll, I'll, I'll spare you unless you want me to, but that's really how that kind of vault.

Mike Gardon (29:01):

Okay. Yeah. I mean, again, similar to my story as, as we've talked about before, but you know, I was doing consulting innovation consulting for a large fortune 500 company. And I kind of said to myself, like, all right, I'm gonna give this a couple years. Like, I'm probably not the best employee, but I probably can learn some things. And then I'm either gonna go be CEO of one of these companies that we create and spin out, or I'm gonna go do my own thing after a certain period of time. And to your point around acquisition entrepreneurship, like I didn't have a burning idea either, but I had some SEO digital marketing skills from a previous life. And I just said, well, why don't I just kind of start to buy some sites here and there that I like and work on, 'em in the kind of in the garage and uh, at off hours and see if I can get it going.

Mike Gardon (29:53):

And so I think that's like, that's where I was kind of introduced to AC acquisition entre, newer ship was from that angle of the side hustle of really trying to pursue and maximize freedom for myself. I never have really looked at like a career track. Right. Like, but it's like, how can I put the pieces together of my life to have a great work life? Right. I don't care about balance. I think that all of this stuff up that we do is intertwined, but how can I put all that together? I've got three kids. And so that's all like, I was always thinking of that. And I just started looking around like, well, how can I do that most efficiently? And it seemed through acquisition entrepreneurship. So, and, and you were down that kind of very same path, which is great. So I know you wanna get into acquisition entrepreneurship.

Will Smith (30:48):

We don't have too much, I've said my piece. I can say more, but go ahead.

Mike Gardon (30:52):

Like, how did you decide on a podcast? Right?

Will Smith (30:55):


Mike Gardon (30:55):

Is I have a podcast right now. Right. And I'm, I'm, I'm quite honestly like, how do I grow this thing? Like, how do I make this bigger and do this? It seems to be so many, like how did you land on that idea and think, you know, and think you can make a goal of it.

Will Smith (31:10):

Yeah. So when I first uncovered acquisition entrepreneurship, I saw it as this kind of niche of entrepreneurship. That was really for all the reasons that I've been saying. And yet there didn't seem to be like kind of an authoritative brand media brand online, be that a website or a podcast, or what have you talking about this in a really professional way? As a side note, I had noticed in the, I no noticed I'd been listening to the podcast and, and on the website for many years, indie hackers and indie hackers is a website about for developers, programmers, technically oriented people who build online businesses and as entrepreneurs. And it's sort of a counterpoint to the Silicon valley unicorn go big or go home thing. It's like, actually, no, you can build a great thriving online, big business. It doesn't have to be the next Uber, the next Facebook.

Will Smith (32:07):

It can be some small niche, SAS app and an extremely rewarding experience. And so the founder of that, Corland Allen kind of identified this similarly, like a, a niche of entrepreneurship and it just, it had exploded and indie hackers that website and podcast, I mean to the point where like people now call themselves Indy hackers. So he called the website, Indy hackers, and now that's become a label for this entire kind of genre of entrepreneurship. And I was inspired by that because I was like, okay, here's somebody who's identified a type of entrepreneurship, put a stake in the ground, become the voice of that community, the voice of that path. And it seemed to me like acquisition entrepreneurship was ripe for a similar sort of voice or advocate or media property. So I see what in Cortland has done with any hackers is kind of a north star and that, that another property hopefully acquiring mines.

Will Smith (32:56):

Mine can be that for acquisition entre ownership. Now why a podcast? So I had initially thought this is gonna tie into what I said about earlier about framing. I had initially thought that I would put up that it would be a website with text interviews. And so I reached out to all these people that I had found that had acquired businesses and said, I didn't really have much of a website at the time or any brand and equity or anything that it was just starting from scratch. And I was emailing these people saying, Hey, I want to interview you and put it on this website. And it'll be a text, little an article interviewing you, basically not that complicated, like not that confusing of a pitch, but I just wasn't getting people responding to it. And then when I changed that to like, Hey, I have a podcast, Will you come be on my podcast about buying your business?

Will Smith (33:45):

That just landed so differently with people. They were like, sure. So the difference between taking the three sentences to be like, Hey, come and be interviewed by me. And I'm gonna write an article about it. And it's gonna go on this website, not that complicated, but still a little bit more versus, Hey, come on. My podcast, people were just like, yes, to the, the podcast question. And I got like crickets from the other question. So I kind of backed into doing a podcast cuz it was the only way I could get people to say yes to being interviewed. Now, in retrospect, it was so obvious to do podcasts in the first place. It's a natural medium to tell stories. It's the best medium to tell stories. So anyway, that's how I arrived at doing a podcast, Mike, because you're what you're getting at is like podcasts. It's incredibly crowded, very competitive. You know, why launch yet? Another podcast? I wasn't like I'm gonna launch a podcast. I was like, I'm gonna build a media property or run acquisition entrepreneurship. Doesn't matter what the format is, website, podcast, newsletter, whatever. And I just of the podcast, because it was the only way I could get people to say yes to being interviewed.

Mike Gardon (34:45):

That was a great frame. Like how you frame that wide exactly. Property instead of limiting yourself to one thing. It's really interesting. Yeah. I mean, I asked a question cause that selfishly, I wanna learn from you, right? Like I got this podcast, then I wanna figure out how to take a it bigger and reach more people and, and help people and all that kind of stuff. So that's great.

Will Smith (35:06):

Mike, actually, can I say one more thing on this?

Mike Gardon (35:08):

Yeah, absolutely. Go ahead.

Will Smith (35:09):

Because I don't know. Um, if your audience Will think about this, but one of the things that entrepreneurs often do is they try to find a new idea, a completely original product, right? And many entrepreneurs come up with an, then they Google and find out that somebody's already doing it and they say, oh, somebody's already doing it. And I've gotta go back to the drawing board. And this is a really common flaw in the way, many entrepreneurs approach, putting something into the market. And so what you see now is people pushing back on that and saying, no, like if in a competitive market actually go for competitive spaces because a competitive market tells you that there's demand there and there's already consumers who want this thing so better to, I mean yeah, better to go into a place where there's a lot of competition because you know, at least that there's an appetite for the thing.

Will Smith (35:55):

So podcast is great. An example of that because yes, there are so many podcasts. It is very competitive, but the reason there's so many podcasts is also because it's, it's this flourishing growing market. There's huge demand for this basically newish format of, you know, people consuming hour long, strictly audio content, which 10 years ago is bar there. So then the calculus is like, well, can I produce a product? If you wanna call a podcast, a product, can I produce a product that is a high quality product that is somehow differentiated, that is better than my competition. And if you look at your competition and, and say to yourself that yes, I can differentiate myself from these guys, then you should be scared by the competition. You should just feel that you need to deliver a differentiated product, but you can feel secure that there is already an audience there. And I personally have been burned by launching products into the void where there wasn't necessarily demonstrated appetite or demand for what I was doing. And it's just, you can't be, people want your thing. So I'm, I'm now a big advocate of going and that's circling back to acquisition, entrepreneurship itself. One of the other great things about buying a business is you already know that there's demonstrated demand because you're buying a business that's already has customers. So yeah. I just wanted to say that about competition.

Mike Gardon (37:14):

Yeah. Very, very good point. I think that's totally true. And I love the tying with acquisition entrepreneurship. If an audience member is sitting there in their job and they're thinking about God, I would like to try to start a business or I just don't know what idea I have or I don't know how to assess competition or any of this stuff. It's like, okay, well, one option is go buy a business. That's had 10 years of positive cash. It's like, exactly, it's a pretty good leading indicator there. I'm gonna throw you for a loop. I want to ask you maybe like how many people have you interviewed

Will Smith (37:48):

Episode 63 just dropped this morning. So I'd say 63, 63 conversations on acquisition entrepreneurship.

Mike Gardon (37:52):

If you could, off the top of your head, boil down the top two to five eye opening insights that you've learned from your audience about this topic of acquisition entrepreneurship. I mean, how would you characterize that for our audience?

Will Smith (38:09):

I think I do have those cuz certain themes come up over and over again. And they're not ones I necessarily would've expected first. I'd say this is doable. So part of me launching acquiring minds, but is like, I, you know, I'm interested in buying my own business. So I've been interview. I've been just completely immersed in acquisition entrepreneurship, but I'm the first to admit I haven't bought a business myself. So I'm learning from my guests with the expectation that I probably Will go out search for and buy a business. But when I was first starting the podcast, I was like, do people really buy these businesses for your audience? One of the most common websites where businesses for sale are listed kind of the Zillow of businesses for sale is BI by sell. It's called BI by sell BI by You can go on BI by sell and your own geography and see all these businesses for sale.

Will Smith (38:54):

The plumbing company, the cafe on the corner, the laundromat, the, the, whatever, the, the digital marketing agency. And I was very familiar with this site for years, but I'd always just kind of write it off and like, do people really buy these businesses? Like anyway, I was a little bit skeptical about this path to be honest. And so my first takeaway is that no, it is, is not easy. I don't wanna oversell it. It's definitely challenging, but it is certainly doable. I have 63 interviews to attest to that and many, many, many more, um, in the pipeline. And it is as financially compelling as the kind of back of the envelope. Math suggests. So that's number one. Number two is, um, I think that there's a real for entrepreneurial mind people to acquire businesses and improve them businesses that were founded by somebody who wasn't necessarily a business person, let's take a, a plumbing company.

Will Smith (39:47):

For example, oftentimes that 30 year old plumbing business, which might be a two or 3 million, 5 million business, maybe a 10 million business was found rounded by a plumber. And he just grew a crew around himself. And then one crew became two and three and four crews. And he was a plumber first and he was never necessarily super growth oriented or operations oriented or whatever. And there's so much opportunity for somebody who comes in and looks at one of these business with a fresh set of eyes, with an orientation to grow or to improve just somebody who is an entrepreneur first. It's a really exciting prospect cuz so many of the millions of small businesses we see around America are not actually, maybe they're not doing as well as they could. They're not actually optimized or growing as quickly as they could. So that's really cool. I'll stop after this one.

Will Smith (40:33):

I could cuz I could go on. But the third thing I'd say is there's this really cool intersection of white collar and blue collar. So I think many people know like blue collar jobs have dwindled in America to be a blue collar person in the forties, fifties, sixties, and seventies. You could be live a solid middle class life that's become more and more difficult. The percentage of the population that goes to college is, has just gone up and up up the celebration of professional careers now is just like very white collar oriented. And in this world of acquisition entrepreneurship, there's this really cool intersection of blue collar and white collar. So a lot of the people who are buying these businesses are white collar people, people who, you know, many of them might have an MBA and or they come from tech or whatever. Somebody like me whose experiences very white collar, but kind of a little more varied.

Will Smith (41:20):

And they might buy that plumbing business and be working with people who come from very different backgrounds. There can be kind of a, a six month transition of kind of a getting to know you. And it can be a little bit like both sides kind of sniffing each other out. But when all of that kind of the dust settles from an acquisition transition post acquisition, it's very, very rewarding for the acquisition entrepreneurs. People like pushing, you know, numbers around an Excel spreadsheet are writing code turns out not to be for a lot of people as meaningful as just working with crew and working with people. That's a theme that comes up over and over. I don't wanna suggest that all of my guests that the only path of acquisition entrepreneurship is buy a blue collar business. It's not, but it is a, it is a common one and it's just a really rich and interesting life choice for white collar people. I think to buy blue collar businesses and work with blue collar people and also not to get too high minded about it, but like the polarization in America, a lot of that does fall along blue collar and white collar. The red blue split is kind of blue collar white collar in many cases as well. So I just think that there is something healthy in blue collar and white collar people finding each other in some ways,

Mike Gardon (42:29):

Very cool stuff. Very cool stuff. And yeah, for the listeners, obviously there's a whole buying these small businesses that have been started over real businesses, right? And then there's also marketplaces to buy Amazon websites and Shopify sites and, and other types of digital type products like flip a and, and other places. I, I bought websites on flip a, so there's this whole world there. So if you're trying to figure out how to do a side hustle or wanna get another income stream going or just wanna make a change, you just want to get out right. Take a look at this world of entrepreneurship by acquisition and the best place to start. I've learned a ton from it already listening to it is Will's podcast. Acquiring mines, definitely check that out Will thanks for being here. Where else can our audience find out more about you learn more about you on the, uh, interwebs as they say.

Will Smith (43:24):

Yeah. Thanks Mike. I appreciate that. And thanks again for having me on this is, this is an awesome conversation. The website for acquiring mines is just acquiring And then there's a lot of conversation around acquiring this on Twitter. My Twitter handles at when there's a Will at, when there's a Will and you'll see me tweeting stuff and, and replying to other folks, there's this whole conversation on Twitter, around acquisition entrepreneurship. So if you're really interested, that would be, I'd encourage you to hop on there and, and follow me and, and others that Twitter Will recommend after you follow me.

Mike Gardon (43:55):

Awesome. And we Will make sure we link to all that in the show notes. So folks have the exact Twitter handle and, and uh, website and all that kind of stuff. Will my brother. Thanks again for being here. We really appreciate it. Love the conversation and we'll talk soon.

Outro (44:09):

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