Tim Ludwig Transcript

Tim has been a great early supporter of The Operator’s Handbook and continues to be a close advisor as I build this new media company. Tim believed in me early in the podcast creation and continues to be an impactful mentor in my career today. He is the perfect person to host this special episode, and I’m incredibly grateful for all the time and wisdom he has shared with me. Please enjoy this turn the tables episode with Tim Ludwig and I.

This is Tim Ludwig, and I’m here to interview Alex Bridgeman, the normal host for Think Like an Owner. A little bit of background on me to kick things off before we dive in and start asking Alex some questions. I’m a longtime search fund investor and owner of Ohana Capital, which is my private holding company for small businesses. I first connect with Alex back in April of 2019, when he was just getting started. I think he had five episodes in the bag at that point and just a handful of downloads. And today, two years later, he tells me that he’s now got 67 episodes of the podcast recorded and listening is up a 100X since then. So over 120,000 downloads. Congratulations Alex.

Thanks Tim. Yeah, you’re the perfect person to do this interview because I really appreciate your early support very early on. And I think if there was a board of directors for Think Like an Owner, you’d be a very core member of it. I’ve really appreciated your support. And I would consider friendship over the last two years or so. So I’ve been really enjoying that. But yeah, as an intro for myself, I was born and raised in Portland, Oregon. We lived primarily in the Portland area, but we lived in Pittsburgh for three to four years when my mom was in her residency program. And while we were there, the doctor at the hospital that my mom was a resident at had Steelers tickets. And so every so often, we’d get to go to a game because as a doctor, you can’t always go to every game on Sunday.

So we became Steelers fans, but we were flying back and forth between Portland and Pittsburgh a lot. And so I became an aviation geek and I loved airplanes. I loved every act of flying, even getting your baggage or walking down the jetway or sitting down at the plane and looking around at your seat and trying to guess the best row on the plane that’s going to have the best window alignment with your seat. Every aspect of flying, I just loved it. And so as a kid, I would love playing with planes and all that sort of thing. But every so often in the newspaper, there would be an article about an airline. And I remember the first route that JetBlue announced into Portland. It was a JFK to Portland flight and it was a full page ad, and I thought that was just the coolest thing ever, it was a pretty new airline at the time.

And to have a nonstop flight to JFK in New York, the big apple was really exciting to me. And so it was fun to read about their business. And I started reading about other businesses alongside that business section. And so I thought, “Oh, this is really interesting.” And especially I loved every article about the airport or airplanes, airlines. And as a kid, I would draw out a map of the state of Oregon and then plan out what my airline one day would be. And I planned out a hub in Bend. It was called the Oregon Air Network. We’d have flights from Bend to Eugene or to Burns or Pendleton. It would never have worked economically, but to me, it was so much fun planning out a route map. At that time, I had considered all businesses were either airlines or something else.

And eventually I thought, “Well, that something else is probably really interesting too.” And so I read the business section more and more. And then into school, I started an investment club because I thought stocks were also really interesting. And it turns out I’m not good at managing high school students because it didn’t last very long, but it was fun to explore other businesses and see what other folks were finding because we had a stock competition through Google Finance. That was really fun. Marijuana was just beginning to become legalized. So one friend bought a weed stock that doubled overnight and we thought he was the most genius stock picker of the whole group, but it faded out because I wasn’t very good at managing it, but it was fun to study the Berkshire model. And I thought that was an interesting model because you could buy these private businesses and then use the cashflow to buy other ones. I thought, wow, that’s really cool. But Berkshire is gigantic and not relatable at all anymore.

And so I started to get curious on other people on a smaller scale doing that business and buying other companies. And so I started looking around, but if you don’t have the key word for something, it’s really hard to find a solution. Like we had a barbecue and the first night it broke and I was trying to figure out what is the problem? Because the auger wasn’t pulling wood into the fire anymore and it was losing temperature. I thought, “Okay, I don’t know what’s wrong, but I’m trying to Google and figure it out.” And eventually figured out there’s a certain bolt and you figure out the name of it. And you go to Home Depot and get the new one. And once you have the keyword, it takes 10 seconds to find the solution. But until then, it takes hours.

And it was the same thing with businesses. I didn’t really know the term search fund or micro private equity or private equity at all, but then listening to Invest Like the Best and hearing Brent Beshore and Harvard professors and Chenmark on the show was like, “Wow, okay. There is a world of people that do this and here are the terms to go find it.” And suddenly you can start searching and find all these people. And I thought, “Wow, this is a really interesting world that I’ve kind of run into. By far the most interesting place I’ve found in finance or business.” And up to that point, I thought being a value hedge fund manager will be kind of a fun role, but realized that pushing numbers around on the screen…

Can I just stop you there for a second?


You just covered a lot of ground. You went from marijuana stocks to Berkshire Hathaway, to small businesses and search funds. What was the span of time between that evolution in your business interests?

I think from up until high school, it was airline focused, drawing route maps. And then in high school, stocks became interesting and a few friends had talked about them. I thought, “Oh, this is interesting, you can literally participate in another company’s earnings without actually doing anything.” And that concept is really cool that internal leverage you can build. So I’ve started following them and that’s where the marijuana stocks came in. And then college was okay and I’m starting to listen to podcasts. I find these really interesting, found Invest Like the Best because a lot of folks I respected really listened to it closely and cared a lot about it.

At the time, I was still… I thought being a value fund manager would still be really fun. And so I talked to Jake Rosser who was a fund manager in Portland and I was able to get lunch with him and he recommended I get on Twitter. And so with Twitter, you can also find other podcasts and that sort of thing. But that was around college. And then actual launching the podcast was end to college.

Prior to the launch of the podcast, was there any inclination on your part to do something entrepreneurial or were there small entrepreneurial ventures along the way? Or how did that come to be that you actually decided and you may not even consider yourself an entrepreneur when you launched the podcast, but was there any sort of history or gut sense on your part that this was a path that you were likely to take at some point in your career?

I definitely knew I wanted to be an entrepreneur, but my focus for awhile was starting an airline, even though the economics are terrible. I admired folks like David Neeleman, who can find five airlines with 10 kids. I just thought that was a Herculean effort. I admire him a lot for it. But to me, it was airlines for awhile. And then as you start to discover other businesses, you kind of figure out, “Okay, well I could be an entrepreneur in a bunch of different ways.” Don’t really know what that looks like yet. I didn’t necessarily think of the podcast as an entrepreneurial venture. I thought of it more as a fun project to get to know people. And it’s just grown since then into maybe more of an entrepreneurial endeavor.

At what point did that shift take place when it went from a hobby to indulge your interests, to something that says, “Hmm, maybe this is actually where I want to spend all of my time, rather than just a portion of my time.”

I started the show in November, 2018, which was the first semester of my senior year. And I was working for this wealth management firm with Nick Fisher and Jason Lashon. Nick Fisher is someone I’ve known since high school. And he was really encouraging on the podcast front. And I think he was really instrumental in starting it. And for awhile, it was kind of my just fun hobby to get to meet people. And I remember flying out to Jamie Catherwood’s happy hour in DC and meeting a few folks. The podcast at the time was six, seven episodes maybe. It was super tiny, but one person there was like, “Oh yeah, you do Think Like an Owner, right? That’s your podcast.” And it just blew my mind that someone I didn’t know have listened to it and cared about it to say hi. And that’s the first time I was like, “Okay, well, someone actually cares about this. So maybe it could be something more.”

But didn’t really think about it until it was probably a year after I graduated in that summer of 2020, where there’s a few folks I was chatting with, who said like, “You should look at this. There’s people who are starting to make businesses out of podcast through sponsorships or other means, and they’re working on it full time.” And I thought, “That’s pretty cool.” I enjoy doing this podcast. And at the time it was monthly and I didn’t really enjoy doing a monthly podcast. It was still something I had to do all the effort to put together. I had to do the audio editing and putting the website together. And I knew that I wanted a weekly podcast, but to do a weekly podcast, you need help because putting an episode together was five to six hours of time, editing the audio, setting up the email, all that sort of stuff.

And so I knew I needed help, but to get help, I needed revenue, generally. And so I was thinking about like, “Okay, well who would be a good sponsor for a podcast focused on investing in small companies?” And I thought, “Well, folks like banks or accounting firms would probably be good fits.” And so I reached out to a few and Live Oak and Hood & Strong were excited to be a part of it. And then we had a few other sponsors joined later like Oberle in. It was the realization like, “Wow, okay. We could not only get sponsors who could benefit from the podcast, but that would allow me to work on it full-time, make it into a weekly podcast. And it could become like a larger project than it already is.” I thought of it kind of is raising money to build a podcast.

And at that point, I was like, “Wow, okay. This could actually be full time.” And that encouragement from people who were saying, “Yeah, try it out.” And I think that was enough to get me to explore it a little bit. And once I signed sponsors, I put in my two weeks notice at the wealth management firm. My final day was the Thursday before my wedding. So I started marriage off unemployed.

Starting two new ventures at once.

Indeed. Yep.

Did you have specific metrics in mind that were the critical points for you to make the decision to go forward or is it merely the sponsorships? And did you write a business plan? I mean, did you take some of the more traditional steps or everything had been happening organically and it just sort of evolved into you leaving your job and gathering the sponsors?

I think evolved more organically. I didn’t have a particular business plan. I had ambitions and I wrote about those ambitions to sponsors. I’d told them you can help me build this podcast, that’s going to be really valuable. And it could be a larger project, but only with help from folks like you. And to me, that was enough of a business plan to kind of see a vision for what the show could be. But up to that point, I hadn’t really spent much effort marketing it. I talked about it on Twitter and got to know a few folks through a newsletter I was writing. I’ve fallen off the bandwagon of writing newsletters. I should write a little bit more. I’ve stopped it in the last few weeks or so. But at that point, it was mostly organic and it just expanded with one small step each way.

What were your emotions when you left your job and decided to go on this full-time, especially with the start of a new marriage happening simultaneously? And what was the support like from your wife?

Oh my gosh. Yeah. Michelle was super instrumental in all of this. She’s always encouraging of the podcast. She thought it was the coolest thing that I could put something out there and then folks actually download it and listen to it. I still have this screenshot of the first 50 downloads and the idea that nobody was listening or that someone was listening that I didn’t know, was super cool to me and especially cool to Michelle. And so she was always encouraging me. And whenever I would tell her after dinner, “Hey, sorry, sweetheart. I have to edit this podcast episode. I can’t spend much time with you this evening.” She was perfectly fine with it. And that was okay.

So her support was huge and her support to do the podcast full-time was even greater. And so her support in letting me try out this venture that had a lot more risk than my job did meant the world to me. But I think elation was the first feeling, like holy cow, this will actually work. Like this can be a success. But also the tremendous fear that now it’s on you to provide for yourself. And I effectively gave myself three months to prove that the model could work and see if sponsors would renew after that because we had signed three months agreements. And so I thought, “Okay, I have three months to build this into something meaningful and see where it goes.”

And luckily enough, it worked, but I was really afraid that it was just going to fall apart. And after three months, I was going to be out with no job and no podcast and have to figure something else out. But elation and fear in equal amounts, I think was the primary feeling.

That’s great. And certainly, very common to all the feelings I’ve ever felt as an entrepreneur. You mentioned earlier, I think you described the podcast as being about investing in small businesses. Listening to the arc of the episodes over the past couple of years, it really seems like it’s grown beyond that initial mandate. What’s the evolution been like from your perspective and what kinds of stories and people do you gravitate to now maybe in contrast to what you were looking for and doing earlier on in the podcast?

I think folks who acquired businesses and actively sought them out, so searchers or search investors, independent sponsors, PE firms, people who bought and acquired small companies were by far the most interesting to me at the start. And so a lot of my guests focused on the investment aspect of buying small companies. With every episode, I usually record an episode with someone I just find personally interesting. I figured if I’m interested in this, there might be someone else out there who likes listening to this type of episode. So I’m just going to create a podcast that I myself would want to listen to.

That’s just been the guiding principle through any episode I record. But it slowly evolved to more of the management and operations of running a business. I began to see that as much more interesting because buying a business, it’s something that a searcher might spend two years on, but then they spend seven to 10 years or more actually running the business. And so I thought, “Wow, there’s actually a lot more stuff that goes on running a business.” And previously I didn’t find it that interesting. I thought running a business was kind of mundane. But over time I thought, wow, this is actually a super intricate puzzle that needs to be solved every single day and has lots of people and customers and vendors and parts of the company that have to fit together. And it’s the operator usually holding it together sometimes just by their fingertips.

And I found that just so much more interesting. And so I eventually have gravitated more to the operations, but there’s still a blend. Every so often, I still find someone who has usually a mixture of the two where they run a business, but they usually acquired the business or they’re looking to buy another one, but they’re actively in the operation seat, running their company.

Thinking about the podcast, you’ve created just a wonderful environment for you to learn and absorb from people all over the country that are doing something that you’re really passionately invested in. From that perspective, and talking to the successful operators and investors, for you, what have emerged as the common traits or themes from those people, the messages that sort of carry on from one episode to the next that you can point to holistically and say, “These are the common threads that weave everything together here.”

I think a lot of these folks are action first. They definitely do research of course, and look through the different options that they have, but they’re really inclined towards taking action on something rather than doing months and months of research. So if there’s a problem in their business, they often have to just respond immediately. And so folks who have that mentality are often really good entrepreneurs, from the entrepreneurs that I’ve spoken to. But they’re also just not afraid to do something that’s really different from the typical path for what they’re working on.

So if they’re in banking, private equity, consulting, or in a large corporate business, it’s not usually in the path of those careers to go buy a small company, like a boring sweaty business that’s maybe in the middle of nowhere, it’s not typically of that path. And so these folks are often okay with that though. They’re okay with maybe looking a little funny or they go to their holiday parties with their families and their family is asking, “What happened? Where did your finance job in New York go? What are you doing in Wichita?” There’s a few funny stories from that, just entrepreneurs having to explain what they do, again. But I just love folks who can do that, who have the resolve to choose something very different that they see opportunity in. And I think there’s a really strong current of that trait throughout a lot of the entrepreneurs that I’ve talked to.

How about with the investors or the investor operators, maybe that invest but also operate? Any similar or any differences?

I think they’re fairly similar. A lot of the investors I’ve spoken to were searchers or operators beforehand. And so I think they take that same mindset, but just apply it to investing. I think a lot of them have a divergent view of things too. They view business fundamentally differently than maybe a public market investor does just because they’ve seen what the inside of a business actually looks like. And so the questions they ask are usually revolved around people and systems and that sort of thing. So I think they just have a way to view businesses a little bit differently than most folks. But that’s a good question. I haven’t thought about that one before.

In my experience, I know when I started investing, it completely reshaped how I thought about businesses and jobs. And it made me think, or sort of rewind the tape like coming out of college, the decision process that I went through to select a job was very different than the one that I would’ve made later in my career after I’d done some investing, and just being able to put the two pieces together about what makes a good job or a good company versus what makes a good investment and the marriage of those two, to me, made it feel like a much more comprehensive view that in my own case, I think would have led to some different outcomes.

After all those episodes, there’s got to be some really special and memorable moments from the podcast. Any that come immediately to mind?

I think the immediate one for me is the first episode. I was part of this entrepreneur program at University of Portland called E-Scholars. And we had this trip to New York that the program did every fall. And I had listened to the Chenmark episode recently a few times and I decided, let’s see if I can convince my professor to let me travel to Portland Maine during the three or four days we were in New York and go visit someone at Chenmark, anyone. And so I got approval from him to at least travel a little bit. And I cold called Chenmark and Palmer Higgins actually picked up. And I was asking him, “Is there anyone from Chenmark, who’s going to be available for a podcast potentially.” And he said, “Oh, Trisha’s going to be heading down to Boston on business during that time, you could take the train up and see her.”

So I thought, “Great, okay, I’ll meet her there.” And emailing back and forth with Trish. She was between meetings and agreed to meet with me for, I think, 45 minutes or so. So not even the full hour and a half that I usually do for a podcast. And there wasn’t really a great place to meet. So we ended up meeting at this shopping mall in Boston. And so I took the train up. I took the SL because I thought it’d be fun. I’d love trains and I thought it’d be fun to try the faster one. I wasn’t a huge fan because it was really rickety on the old… it was on the same tracks that the regular trains took. I was trying to take notes ahead of the meeting, ahead of the podcast on my computer and the screen would just vibrate. And I had to take a nap instead.

But I met her at the mall and we were looking around to try to find a quiet space at the mall. And I went into one of the banks that was there and I asked him if I could use their conference room. And the first one went back to the manager, the manager was saying no because there are other meetings of course taking place. So we sat outside, it was just a table near a food cart. And so if you listen to the episode, you can hear people walking by or chairs being pushed back. I think there was a few loud kids who’d walked by at one point, but it was so funny because at that point, I hadn’t done a podcast before ever. And so I’d wrote down my questions ahead of time on this notebook and I asked them pretty much in order.

And so it didn’t flow very naturally as I quickly learned later on for recording podcasts. But Trish was super generous with her time and perfectly willing to sit down with me, even in this small to record the episode. And on the way back, I was so excited that I actually recorded an episode and I had taken my microphones, and to protect them on the flight, I wrapped them in my clothes so that they got knocked around, the clothes would protect them a little bit. But when I got home back in Portland, I took all my clothes and threw them into the washing machine with the microphones. And I didn’t realize that the microphones were in there until I took them out to go into the dryer. And I heard this loud clang as I threw the clothes into the dryer, realizing that both my microphones had been washed, but I tried them for episode two and they still worked.

And so this microphone right now that I’m using was through the wash and has been through the wash for all 67 episodes afterwards, after that first episode. So these are resilient, the Honda Civic’s microphones.

That’s great. Any other moments that come to mind?

There’s a few smaller ones, convincing Collin Hathaway to be on the podcast. I’d seen his website in Seattle and there weren’t that many, and there still aren’t that many small company investors in the Portland Seattle area. So I pretty much tried to cold email everyone that was in the area and Collin was able to respond. And from the first phone call, I knew I wanted to have him on the podcast because he was really interesting. And he was really reluctant at first, but I emailed him every few months to try to get him on the podcast. And he always said no, but one time he said yes, and so I immediately tried to schedule very quickly an episode and put it together and he didn’t like the way he sound on the first one, he said he was tired, but on that second recording, he thought it was pretty good.

And so we released it and he sent it out to his network, which sounds like at a pretty substantial network because it got a lot of downloads. And from that point on, he was super interested in the podcast. He sent me an email every few days. Like sometimes the question would just be in the subject, how many downloads now? There’d be no message. And it was fun to just see him go from kind of, not necessarily skeptic, but just not super interested to being really interested and excited about the podcast after seeing that folks he respected had listened to it and liked it and he got good feedback on it.

So that was another special moment to me. But other tiny moments, like whenever someone introduces me to someone in their network, I always take it as the highest compliment possible. If you’re willing to share a friendship with somebody that you know really well with me, I take that as just a giant compliment. And I’m always appreciative of those.

I think you’re doing an amazing job, building a community of people that support you and support the efforts. And I was chuckling to myself when you were talking about your persistence in getting Collin Hathaway, because I’ve definitely been on the receiving end of your gentle nudges to get me to do all kinds of things. And you are, if nothing else, very, very persistent. The podcast is obviously been really fulfilling and successful. And I know over the past few quarters, you’ve been working in your skunkworks to develop a number of new projects. Any of those that you’re ready to talk about and can share a little bit more with your audience on?

The one I’m most excited about is The Operator’s Handbook, which we can talk about a little bit more after describing a few others. But that concept is a print only publication on running small companies, and each article is an interview with an operator on a specific challenge in their business. So how did you raise prices? How do you retain great technicians? Those sorts of topics. And then in a print only format, roughly quarterly or so. We can talk more about that in a little bit, but there’s a couple others that I’ve tried and I’m always trying to tinker with some project.

And most of the time, the project is interesting for three weeks or so, and then I start to lose interest and then I ended up giving it up and not trying it either after either I’m not interested or it doesn’t seem like a viable project. And so I stopped. But I’ve tried a few things. One thing I tried was recreating the podcast in Roam Research. The one interesting thing about Roam is you can put in lots and lots of texts and then you can tag certain pieces of text and then also make it all searchable. So I can put in all of the episode transcripts into Roam and then you can search for keywords or specific stories and that sort of thing.

I’m not convinced that Roam Research is super usable from a UI standpoint. So I’m not sure that there’ll ever be a project I release publicly, but maybe I might use elements of that in The Operator’s Handbook. I’ve shied away from most consulting as I try to focus on my own stuff. I thought about investing in searchers. But one challenge I’ve run into is I don’t think I’m necessarily a great investor or picker of searchers. So that strikes me as a little bit more advanced of a skill set that hopefully I’ll build over time. I don’t feel quite ready for immediately, but also the time commitment. I think it takes a lot of time to do it really well.

And if I’m going to do it, I want to do it well. And I don’t think I have the time available to do it to the degree that I’d like to. And also it just puts a lot of stress on your time if you’re not able to devote substantial parts of your day and week to it. So I’m going to hold off on that one for now. But I also thought about doing a podcast network and just having a couple other podcasts, like Think Like an Owner, underneath the Think Like an Owner banner. And I’m going to pause on that one too for a little while. I think I want to make sure I can focus on good projects. And one thing I’ve found out is that I’m not very good at managing more than really two or three things at once.

If I have four or five things I’m trying to do, I often don’t do any of them very well. And so I’m trying to find a little bit more focus in the work that I do. And so The Operator’s Handbook and the podcast are my two main projects at the moment that I’m focused the most on.

It sounds like a really good pipeline of future projects and an exciting lineup of current and near-term things. Let’s circle back to The Operator’s Handbook because that’s something that’s near and dear to me, and at least what I want as a consumer. Growing up, one of the things that I think was pretty foundational to my own interest in small business was Inc. Magazine. And over the years, it seems like it’s drifted from its original content towards things that are more VC backed and startup and high growth and leaving out sort of the boring niche industries that I’m most excited about.

And there really hasn’t been much of a replacement for that in mainstream media. I think there’s small pockets of communities like the one that we’re a part of on Twitter. But I perceive there to be a real unmet need there. And I’m wondering if The Operator’s Handbook is your response to that.

I think so, but I think it’s also just something that kind of like the podcast, I started the podcast because I couldn’t find a podcast like Think Like an Owner for the small business investing and operating space. And so I created it myself. And I was also looking for a publication around the same time you had your tweet of the Outstanding Investor Digest, where I was looking for a similar publication, something a little bit, maybe more high-end like the manual of ideas or grants interest rate observer that could cater to running a small company. And I didn’t really find anything that I thought was super compelling.

And so I thought, well, I’ve already done a little bit of the work with Think Like an Owner, just getting to know different owners and what they care about and what their challenges are. And so maybe this is a good platform to build on and add something like Operator’s Handbook, which is a print publication. And we can focus on that market that has been historically underserved or at least recently underserved. I also just think I haven’t found anything like it. There’s not that many folks who really focus on the act of running a small company. It seems almost like it’s perceived as a small market when in fact, I think it’s one of the largest markets. It’s just, there’s not a huge elephant in the room. It’s just a bunch of small companies all across the country, but there’s not a few big shiny examples besides the large tech companies or anything startup and VC type that gets a lot of attention.

And so it just seems to go underserved. But I think something like the handbook can serve to that group. And a lot of our focus on that has been let’s build something that doesn’t have distractions, let’s make it reader supported so there’s no ads. So you open it and every page is meant for you, the reader, to help maximize the time that you have, that is extremely valuable, but we don’t want to distract you. We want to make it paper so there’s even less distractions. So there’s no email notification coming up on a print magazine, and we can focus on telling stories because I think stories are just more interesting. I don’t really enjoy reading how to articles unless it’s trying to fix a barbecue.

And so how can we make interesting content around operating a small business, but with story format. And I’ve kind of done that with the podcast already with interviewing. And so we can interview folks on their challenges in their business and just asking about how did you solve this challenge? Instead of writing an article about how can you raise prices in your business, let’s interview Trish Higgins, who raised prices in her business and have that as an article, where we can tell the owner, “We’re never going to tell you how to run your business, but we’re going to tell you stories about other folks ran their businesses and maybe some ideas could come from you reading that article and seeing if there’s any insights you might apply to your own business.” That’s the general philosophy we’ve taken with also things like boring is beautiful.

We both believe this, of course, that the smaller, more mundane businesses are super interesting and fascinating, and we should devote more focus to them. They’re not flashy Airbnb type companies, but they’re really, really interesting to us and a lot of different people. And so catering to that, we can make the physical design like a Moleskine notebook. It’s very cardboard kind of journal feeling. So very simple, not distracting, but also really exciting and novel to hold and play around with and take notes on. So there’s a few philosophies and principles we’re trying to apply from the small business world to the handbook that hopefully translate really well to readers.

Sounds amazing. How often will you release additions of The Operator’s Handbook?

We’re going to try to release quarterly more or less. We want to write for operators and only operators. So no ads of course. And focusing exclusively on reader supporting. And so keeping with that mantra, we want to make sure we’re only producing content that’s really good. And I’m not convinced yet that we can do that on a consistent basis on a strict, to the day, at the end of every quarter, mailing out a new issue. I think we can get to that point pretty soon, but I don’t want to have to mail an issue that isn’t that good, just because I have to get an issue out by a certain day.

I think as we build up, we can get to a more consistent schedule, but I want to make sure that the reader’s interest is always at the forefront. And to me, a consistent schedule immediately is not entirely aligned with doing that.

When’s the first issue coming up?

Hopefully in the next two weeks or so.

Oh wow.

Yeah. We have a few emails to send out to folks just explaining our philosophy around the handbook with a sample article from Rich Jordan, which has been a really good friend throughout all of this. I was pestering him like I pestered you. I was pestering Rich about what are some different publications you’ve read? And he shared this marine focused publication that had some really interesting articles and they did some cool graphic stuff. And so he was helpful in thinking through a few of these ideas too, but we did an article on hiring and retaining train technicians. So his plumbers, because the first day he bought his business, all of them wanted to leave because they got offers from other companies.

So holding onto them was like an immediate concern of his. And so he was the perfect person to write an article on. And so we have him as the sample article and his article will appear in the first issue, but the sample article will be from that first issue as a taste for what other types of articles we’re going to be putting together.

I can’t wait. This sounds absolutely fantastic. Thinking a little bit further ahead now. You’ve got the beginnings of a media empire here. Where do you think the Think Like an Owner franchise will be 10 years from now?

I don’t necessarily have strict goals and what I want to create. I just know that I really enjoy connecting with folks running and operating and buying small companies. So as long as my projects fulfill that need, I think that’s perfect. That’s exactly what we need to do. I’ve tried to adopt the growth of that goals mindset, to an extent, I lean heavily type A and so most of my life I’ve written out goals and I follow them really closely. So trying to avoid doing that is really hard mostly because I think it’s hard to predict who you’ll be in 10 years.

So for example, 10 years ago, I wanted to be a fighter pilot and join the air force and fly fighter jets. And so 10 years later, I’m now running a podcast. So very different careers, but I think I’ve found the place that I really enjoy and want to build a career in. And so, as long as my projects are continuing to feed that interest of learning how companies are run and acquired and grown, I think that’s going to serve our projects well. But I think the handbook can grow into a larger platform with the podcast as kind of an ancillary project and media business. And then we can add things like conferences. We can add perhaps a mastermind group, research reports, other things on top of the handbook and podcasts that can help continue to share stories about operators, how they run their companies and get them to connect with each other in interesting ways.

And I think as long as I’m doing that, I’ll be pretty happy.

It really created a very special opportunity for yourself with a lot of optionality. And it’s a really kind of a business model that would have been very hard if not impossible to create 10 years ago. I think all of the technology tools that support this creator economy, I think you’re taking advantage of, and you can work anywhere. You can interact with people that are interesting to you and share that with other people, you’re continuously learning and providing a nice lifestyle for yourself and your family. It’s pretty wonderful.

It’s pretty wonderful. And to your point about the tools, something like Zoom, where I can actually record the interview, that by itself is very new. But even stuff like Print and Ship, where I can take a PDF and send it along with the CSV file of all the addresses. So I can send both of those things to the printer and they print off the publication, the handbook, and they send that first issue directly to the reader. So I’m not sitting at home and a truck drives by with a palette of magazines that I need to now mail out. I don’t have to do that anymore, which is phenomenal. And so to your point about technology, there’s a lot of technology that makes this easier.

And so there’s definitely an element of luck of the draw in terms of when you were born, where all of these things align perfectly. Like the technology aligned really well, the growth in the search fund model and buying small companies has aligned really well with all of this. And then my interest in discovering that model has also aligned really well. So there’s a lot of luck involved that makes these things interesting. But yeah, you’re right. What a fun time to be a creator.

And social media as a distribution platform and a marketing arm.

Absolutely. Yeah. Twitter has been extremely powerful for the podcast. It’s the one platform I really lean into and I’ve found it incredibly helpful. There seems to be a nice sharing, friendly, open attitude on Twitter with folks who run and own small companies. And it’s been really fun to see the SMB community really flourish on Twitter and be a node to a certain degree of that community as it grows is really, really fun. I love chatting with people on Twitter. It’s super fun.

Me too. It’s been probably the highlight of the last 18 months for me in terms of my business activities. All right, Alex. In typical Think Like an Owner of fashion, I want to close with a few questions. First being, if you could teach any course in college, what would it be and why? Some of these questions may sound familiar to you?

They do. I love asking this question because there’s always a class that somebody wants to teach, not necessarily class that they want to teach, but there’s a topic that they know a lot about that they’re passionate about, that they would love to share with people. And it’s always exciting to see or hear what that topic is. And for me, I love this Steve Jobs quote, where he says something to the effect of “All the things around you and your world were built by people who are no smarter than you. And you can build on them, you can change them, influence them, and you have this power that you’re not really aware of.”

I think that quote is phenomenal because that recognizes that entrepreneurs and founders are human. They’re not doing superhuman things, even though I think we’ve glorified entrepreneurs to a certain extent in the last 20 years or so. These entrepreneurs, on a day-to-day basis, are doing really things that aren’t necessarily require super human ability to do. And so the class I would teach is every week or twice a week, we bring in an entrepreneur, a writer, artist, someone who can just talk us through your day, like literally what do you actually do from 8:00 to 5:00 PM? What does your schedule look like? What tasks are you doing? With the idea being let’s figure out what tasks are involved in running a company.

And I think from just my conversations with owners, a lot of the things I realized is running a company is hard, it’s challenging, but it’s not intellectually complex. It’s not a hard thing to just figure out how a process is put together. It’s hard to execute it, but the actual workings of it are fairly understandable. And so it will be fun to show that to students where you are capable of running a business like this. You could build a great business, you could write a good book or be a fund manager or something else. It’s entirely possible for you to do that. It’s not super complicated and mysterious. And I think it’d be fun to reveal some of that.

I love that. Yeah. I think at that stage in people’s lives, there’s so many unknowns that if you could just peel back the curtain a little bit, I think people might make very different and much more informed choices about the first stages in their professional careers.

I think it would also reveal some of the power of delegation too, where a founder isn’t doing everything in their business. They often have a huge team around them that’s really important and does a lot of the work with them. And so I think folks realizing that they’re running this company, but they’re not super human. They’re not doing every aspect of the business. They have help around them. And I think that would humanize entrepreneurs to a great degree. If you were in front of a group of students and you talked about all the people in your team and how… yeah, to market our business, we have a whole team to do that, to develop product. We have a total team that does that. Sales are done by another group of people. And it’s not just the founder doing all of those things.

And I think sharing a little bit of that too, would be empowering to students when they realize that to found a company, I don’t have to do every single thing in the company. Maybe at first, but I don’t have to be a superhuman for the entire length of the company’s history.

Everybody can be a collaborator.


This is sort of a Peter Thiel question. What belief did you use to hold strongly that you’ve changed your mind on?

I think just relating to the previous answer with team. I think when I would hear folks on podcasts or read articles and founders and owners, they talk about the team being the most important thing right in their business, I thought it was kind of overrated or maybe they were just pandering to their employees who might be listening or watching the interview. I thought that can’t be true. There must be something else like strategy, or pricing or their marketing is really good or something else about the company is key to its success.

But as I’ve grown the podcast, and once I was able to get sponsors, I immediately hired Matthew Passey to run my podcast editing process. My cousin David Bridgeman does my website and email. With Operator’s Handbook, I have Taylor Cautherine, she was working at an accounting firm and was a guest speaker at my school. I got to talk with her a little bit more and she worked at a forensic accounting firm. And so a lot of her work was in writing up memos that would be read in courts in divorce cases where there’s a business involved, for example. And so they had to be really well-written and punctuation and grammar had to be perfect because it was going to become a legal document to an extent.

And so she’s a really good writer and I’ve enlisted her help because she had a baby recently and she enjoys editing. And I offered to pay her to help me put this handbook together and she was excited to do it. And so now that I’ve got effectively three people helping me in various ways run the podcast and the handbook I’m like, “Wow, okay. Having a team is actually huge.” These folks are really good at what they do or they’re better than me at it. And I don’t have to do it anymore and I can pay them and it helps build their business. And it’s so much more fun because I can now do more things. There’s more leverage with my time and the projects that I can work on.

And I’ve done the full Winnie. Team is by far the most important thing because without a team, you really can’t build something substantial and hugely meaningful. And there’s folks who’ve done it with very small teams, but there’s still a team involved. And I really come around on team. And I think having a great team around you is key to building a good business.

I agree. I was reading something, I think just yesterday, about the definition of a business and paraphrasing, it was something to the effect of a collection of people working together to achieve something that none of them could achieve on their own as individuals.

I love that quote too. The not being able to achieve it as individuals is very true. If I still had to do all the audio editing, that would be six hours per week. With a weekly podcast, that would be every single week. My time would be sucked up by just running a podcast. I would not be able to do the handbook. I would not be able to own a dog and take her out for walks every now and then. So there’s so many things that are enabled by having a team that it’s really incredible.

Absolutely. My favorite question that you ask is this one, which is, what’s the best business you’ve ever come across?

I love this question too, because I leave it purposefully vague. Some folks ask like, “Well, best buy what measure? By revenue per employee, by the business model? What?” I leave it open-ended because I want to hear what best is to that person, because everyone thinks that there’s a different definition of best. Some people love customer service focused businesses that just try to create the best possible customer experience, not necessarily regardless of the economics, but they will sacrifice margin to create a wonderful experience for customers.

Others find just the scalability of something incredible. So Mike Boyd talked about a website that creates website templates and it’s run by one person and has huge amounts of revenue from a single team effectively. Me personally, I love businesses that enable a person to monetize their own intellectual curiosity, because to me, that’s what the podcast has done for me. It’s allowed me to build a business and be paid for creating stuff that I’m interested in creating and following my own curiosity. And so I admire businesses where the founder has found a way to do that for themselves.

And some great examples to me are Stratechery, The Diff, Grant’s Interest Rate Observer, Being Alive Ideas, even hedge funds. Like a hedge fund, in a lot of ways, if it’s… a lot of the value hedge funds that I’ve looked at are run by one person. Maybe they have an assistant somewhere, but usually that one person is just hugely interested in buying small companies or buying public companies or what have you. And so for them to monetize their own curiosity is really cool. And so my favorite example of these is probably Stratechery. And Ben Thompson is in Taiwan. He’s remote. It sounds like he has an assistant, maybe a second one, but he is clearly super passionate about tech and the business of tech and how tech is changing and evolves over time.

And so to see that he’s built this engine that allows him to just follow his own curiosity and work anywhere he wants, that’s infinitely scalable, the more subscribers he has, it doesn’t mean he does X number of hours more work, to be able to build a business like that and follow that is really, really cool. So I’m a big admirer of people who are able to build businesses around their curiosity.

That makes me think of Shane Parrish and Farnam Street as well. I think he fits that model.

Exactly. Yep. And Patrick O’Shaughnessy is another example. Ted Seides to a certain degree. All those folks who are able to build their start off as blogs or podcasts, and they grow into something a little bit bigger. And I agree those are really, really fascinating business. And Outstanding Investor Digest. Stuff like that too.

No, that’s great. Well, Alex, thank you so much. This is the first time I’ve been a podcast host and I really appreciate you giving me the opportunity to learn more about you. It was really interesting and I appreciate you sharing so much about your journey and yourself and all the great things that have happened already with Think Like an Owner and all the great things to come. Congratulations on all the success.

Thank you, Tim. It’s been wonderful to get to know you and your support has been absolutely huge for the podcast. I don’t think it would be to this degree of interesting or unique without your help and without your support. So thank you for helping me out at a very early point in the podcast. It’s been really fun to get to know you and work with you more.

Well, these are the kind of relationships that are most fulfilling to me in life, and I’m trying to lean into them as much as possible the older I get. So it’s a mutual admiration society here.

Wonderful. Well thank you for doing so.


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