2019 Annual Letter: Gaining Traction

Before getting to the podcast, 2019 was a tremendous year personally. I flew to DC for a FinTwit gathering hosted by Jamie Catherwood, graduated college with a new job, and got engaged.

Dear Readers and Listeners,

As I noted in my 2018 Annual Letter to Readers and Listeners, I love reading the annual letters put out by fund managers, CEOs, investment firms, and blogs. Last year, I set myself a goal of putting out something similar for my own work; these letters allow me to reflect on the growth of the podcast, discuss small company investing, and evaluate my personal learning.

Before getting to the podcast, 2019 was a tremendous year personally. I flew to DC for a FinTwit gathering hosted by Jamie Catherwood, graduated college with a new job, and got engaged. It was a life-changing year of excitement and change. Looking ahead into 2020, we’ll have the wedding in August, my fiancé will begin applying to physical therapy doctorate programs, and we might get a dog. It’s going to be a lot of fun!

For the second annual letter, I’ve presented data on the project below. 2019 was a year of growth and progress. Looking at the numbers, I’m shocked at how many people came across the project in some way this past year, especially when the only marketing I’ve done is post podcasts on Twitter, LinkedIn, and Searchfunder.com. The following table compares 2018 and 2019 in terms of new podcast episodes, podcast downloads, page visits, email list subscribers, and new blog articles:

Although the data above is important in tracking growth and general reach of the project, I want to stress that the core goals of my work with Think Like an Owner are learning and building relationships. Since data about page visits and downloads doesn’t show progress toward these difficult-to-quantify goals, I plan to seek out ways to better track and display those factors in the future. This will help me better present progress to you.

New Website

In reviewing 2019, let’s start with the obvious. I moved from thinklikeowners.com to my new personal site, alexbridgeman.com. I considered and ultimately made this move because there are other projects I’m interested in exploring in the future and I wanted to avoid creating a new website for each potential project. By creating a personal website, I’ve created a home for Think Like an Owner and any future projects and work.

I’m happy with the change as I now feel free to write about topics beyond acquiring small companies. Additionally, I added new features to the site that wouldn’t have made as much sense on thinklikeowners.com. New to the site is a “Work” page for my current and past roles at companies. There is also a “Links” page with my favorite resources I’ve discovered on small company acquisition, including what I’m calling “The Quick MBA in Small Company Acquisition” representing the best five links on the subject.


A week after graduating from University of Portland in May 2019, Justin Turner from Traction Capital Partners asked about a possible sponsorship of the podcast. As an admirer of what they’re building at Traction, I wanted to talk more. While the podcast is fairly inexpensive to run by most measurements, $100 a month is a helpful amount to have covered at this stage in my life. Mid-way through 2019 we came to an agreement. Traction now sponsors the podcast and I promote them at the beginning of each episode.

Sitting here at the end of 2019, I’m happy to report the sponsorship with Traction has been fantastic. Not only is it great to cover my costs, but it’s incredible having someone to reach out to for help and questions, especially when that person has a vested interest in my success. I’m excited to continue this relationship into 2020.

Tailwinds Newsletter

In 2019, I published the first edition of the Tailwinds newsletter with an aim to accomplish two things: to become a better writer and to share my thoughts and resources more widely and frequently. Nick Haschka, partner at Cub Investments, recommended the name “Tailwinds” with the idea that if you’re looking to build something, like a business or permanent capital, you should position yourself with a tailwind at your back. Considering I’m also an aviation geek, the name was perfect and I decided to go with it.

Although I initially released Tailwinds on a weekly basis, I received feedback that this was too frequent. I ran a survey to discover other readers’ opinions, and most agreed weekly was in fact too frequent and biweekly would be preferable. Biweekly has been frequent enough that I’m motivated to write often, but I’m not pushed to rush and put out work that I’m not excited about.

As for how the newsletter helped my goals of becoming a better writer and sharing more, the results have been positive. I now feel more comfortable and confident that both writing and quality have improved compared to the first edition of this letter. (Although I’ll let you, the reader, be the judge of that) I have also enjoyed being able to share links I come across with my readers. I find myself keeping close track of the articles I read, which is something I wasn’t doing before the newsletter.

Overall, Tailwinds has forced me to be more open with what I’m thinking about and the ideas floating around in my head. I’ve found a certain clarity from putting my thoughts into words that others will read. Often, my mind feels messy and jumps around to different ideas, but writing them down encourages me to organize. The newsletter has been helpful in so many ways and I’m excited to write more in 2020.


The final major update from 2019 is the addition of the Think Like an Owner community. I put together a Mighty Networks community with forum and messaging functionality and sent invites to my network. The goal was simple: to connect others in this space who weren’t aware of each other and encourage them to share ideas. And wow, has it been a learning experience for me…

I am not the best at running a community quite yet.

When I first started the forum, I posted conversations topics or ideas every few days, and it gained some traction. My hope was that over time it would grow to become its own organism where posts and conversation would flow without my frequent involvement. That wasn’t the case and as I reduced posting, the community saw less engagement. I either need to get better at running the community, or close it and try something else to build those connections. I need to post more and accept that I need to be much more active, or conclude a forum-like community isn’t the most effective medium in connecting professionals in this space.

I’m hopeful that by writing about the challenge here, others will reach out to share feedback and their ideas. I do think it can be successful, and long-term may be very successful, but it may take some rethinking. Please shoot me an email if you have thoughts or advice on what I might do here, including what would be most helpful to you as a community member.

Being an Interviewer

Interviewing is one part of the project that changed the most from the first podcast episode to now. When recording the episode with Trish Higgins, I wrote out every question I wanted to ask her on a notebook. The result was a less natural and smooth conversation that didn’t flow according to the guest’s own interests but rather my own. I abandoned this tactic and, after another episode or two, I stopped preparing questions altogether. Now I research guests more thoroughly in advance, give them prompting questions, and see where the conversation goes. I let them take more control and steer the conversation to what they want to talk about, rather than what I think will sound good in an interview. The result is a smoother episode that feels fun, relaxed, and much more interesting.

I’ve also tried to talk less during episodes and keep questions as short as possible. Sometimes if the answer makes sense on its own I’ll delete the audio asking the question so we can hear more of the guest and less of myself. I want listeners to feel like the guest is talking to them, with me being their voice and a conversation guide. I’ve heard good things about the interview style so far, but if there’s anything you’d like to see improved please reach out and let me know.

Personal Learning and Growth

The reach of the podcast has been astounding and it continues to spark new conversations with fascinating people. All my life if there was someone I wanted to talk to, I usually had to reach out cold through LinkedIn or email. The fact that listeners and readers from 36 countries are now reaching out to me, is mind-blowing. I was able to connect with countless professionals in 2019 in a way I’ve never been able to before.

When I set out to create the podcast, learning as much as possible was and still is the goal and the podcast has proved fruitful over the past year. Each conversation added information to the picture of small company acquisition. And while I have a clearer picture, I still do not feel like an expert and am still building up the intellectual confidence to write about the space. In many ways I feel like just as much of a newbie as when I started this project. That’s clearly not true, but when I began, I didn’t know what I didn’t know. As I explore this space, I’m starting to see and figure out how much I don’t know. There’s so much to explore.

Looking back at all those conversations, two things stand out to me about small company investors. First, there is no common background. In the podcast interviews, I’ve recorded episodes with professionals from hedge funds, consulting, software, banking, law, entrepreneurship, and real estate. Unlike fields such as medicine, education, or even larger private equity, there’s an informality to this space that isn’t picky about where you’re from or how you got here. All that matters is whether you can execute and do what you say you’re going to do. This observation alone makes the space fascinating to me.

Second, these professionals are not afraid to appear unconventional at times. In my conversations with Trish and Palmer Higgins from Chenmark Capital, they told me that when they acquired their first landscaping company after having worked in hedge funds, they had former co-workers and friends say things like, “What are you going to cut my grass now?” Nick Haschka went from consulting at McKinsey to acquiring a small horticulture company in the Bay Area. The team from Searchfunder.com all came from MIT engineering backgrounds. Buying small private companies was not a step along the traditional career paths they came from and I’m sure they got weird looks at cocktail parties. They broke the norm and dared to step out of line for something greater than the typical career path.

The lack of common background and looking unconventional describe what I’ve come to admire about these professionals. They dare to look different from their peers, friends, family, and co-workers so they can build their own path.


In the first year of operation, the podcast became finely tuned. Audio quality improved as a result of trial and error with microphones and recording techniques. Transcripts are available at release, rather than a few days or weeks later, thanks to a new transcription service called Rev.com. As I edited audio from more episodes I found myself navigating the software and interface with increased familiarity, reducing production time. Small growths in efficiency emerged throughout 2019.

Looking into 2020, more efficiency will come, but I want to get better at two things: writing well and building community. Writing as a skill is one I’m still working on and I have lots of room for growth. This skill takes practice and will come with time.

Building community may prove more challenging. I want to help connect this fragmented space in some way. The existing Think Like an Owner community might be the way to go and needs more work, or there might be a better or easier way. In any case, I want to build more, especially in person. I’ve gotten to meet a few listeners and readers, but I’ve yet to meet most of you. I’m envisioning a happy hour of sorts soon for followers of the project. I don’t know yet what it looks like or when it will happen, but I know I want to put something together this year. If you’re interested and have some ideas, please reach out and let’s chat.

Thank you to everyone who’s followed the project over the past year. I hope you’ve been enjoying it as much as I have and are excited for what’s to come in 2020 and beyond. This letter was fun to write and I look forward to writing more for the years to come.

Subscribe to our newsletter

Join small company investors, search funds, private equity firms, business owners, and entrepreneurs in reading the Think Like An Owner Newsletter


Up Next

2021 Annual Letter

What a year it’s been. My wife, Michelle, was accepted into Creighton University’s physical therapy doctorate program and in June 2021 we moved with our corgi, Cici, from Portland, Oregon to Omaha, Nebraska.

2020 Annual Letter: It’s Business Time

While 2020 was turbulent to say the least, it was the best year of my life. I married my lovely wife in late August, adopted a corgi, and began working on the Think Like an Owner podcast full-time.

2018 Annual Letter to Readers and Listeners

As a fun goal for myself, I’ve decided to start writing annual (and possibly quarterly) letters for the Think Like an Owner project to reflect on the growth of the podcast, discussion around the micro private equity market, and my personal learning.

Generic filters

2019 Annual Letter: Gaining Traction

Before getting to the podcast, 2019 was a tremendous year personally. I flew to DC for a FinTwit gathering hosted by Jamie Catherwood, graduated college with a new job, and got engaged.

Read More »