Issue #33: My Plans for Think Like an Owner

My life has recently changed in two big ways.

First, I got married on August 29th in a small ceremony at my family’s home in Portland, OR with 25 of our closest family and friends. The original plan was for 130 guests, but with the pandemic we brought things down to 25 and upped quality on food, drinks, and music.

It was a blast. I can truthfully say I thoroughly enjoyed my wedding. I had a special moment with every single guest, nothing went wrong or awry during the ceremony, and everyone had fun. If you’re getting married in the future, a small wedding is fantastic. Although going forward you probably won’t be able to use coronavirus as an excuse to keep things small without offending anyone, like we did.

The second big change is I am now working on Think Like an Owner full time. Thanks to sponsorships from Live Oak, Hood & Strong, and Barrel, I can now spend all my time and energy making great podcast episodes, writing more, building more relationships, and working on side projects with professionals I admire.

I loved working with Nick Fisher and Jason Lesh at Pilot Wealth Management. I met them in high school, stayed in touch over the years, interned with them in college, and graduated as an associate for them. I consider them both mentors and life-long friends, regardless of my employment status with them. I feel incredibly blessed to have gotten to work with such wonderful people and their heartwarming families. Leaving the firm was painful, but I’m so excited for what’s ahead.

The goal of Think Like an Owner remains the same. To learn about acquiring and operating small companies while building great relationships and friendships with professionals in the space. Now I can execute on this mission with all my time and energy. Many new things will come from this newfound resource.

Episode frequency – The weekly release frequency of the podcast will continue and strengthen. I’m starting to build a meaningful backlog of incredible guests that will raise the bar for the podcast in quality and insight.

Twitter & writing – I’m becoming more active on Twitter and in writing. You’ll see me around more and I’ll be writing more articles, including a few articles co-written with other investors I admire. I’ve found the more I share online, the more folks are willing to share with me and I’m so excited to keep building these wonderful relationships.

Searcher survey – Current and former searchers often hear from prospective searchers wanting to learn about their experience and many of the same themes are brought up. I’ve put together a survey allowing searchers to answer the FAQs about their search that can be sent ahead of any conversations with prospective searchers. This gives the interested person important background information, saves the searcher at least an hour on the phone, and makes the eventual conversation more productive for both sides.

The larger goal with the survey is to publicly share survey results here on this site to form a database where any prospective searcher can review FAQs from dozens of searchers, collectively saving many hours of time for both sides. Anyone interested in the model can quickly glean insights from dozens of searchers about their process and experience and get up to speed much faster than going call by call with searchers.

If you’re a current searcher, operating a company, or have already exited your investment, please consider filling out the survey and sharing your experience with those seeking your wisdom and the wider search fund community.

Website redesign – The website and podcast cover art are getting a makeover. My current style is minimalism, but in a boring, uncreative way that lacks personality. This will be changing within the next few weeks, stay tuned! It will be more obvious this project is about small businesses, not just a personal blog.

Among these changes in the short-term are my long term ambitions for the project. My work in the small company investing space to-date could be accurately described as that of a reporter and commentator. I’ve interviewed dozens of great investors, searchers, business owners, experts, and written often about my thoughts and observations. Going forward, I envision my role becoming an active participant.

The role I’m imagining for myself comes with a few constraints. The primary constraint is geography. My wife is interviewing with physical therapy doctorate programs around the country and starting next year, and continuing for the next three years, we will be heading to one of those programs. That will mean moving to Seattle, NYC, Phoenix, Miami, or my financial favorite, Omaha. I will need to work remotely from any of these locations.

This rules out an outright search for a company to acquire and operate. There’s no sense in acquiring a company in any of these cities if we aren’t looking to stay there long-term. I view it similar to buying a house, something we are also not ready for. If a search is to be done, it should be done where we see ourselves staying for at least a decade. Additionally, I don’t think searching complements my current skill set. I have no experience as an operator or a deal-maker and there’s no way to know if I’d be successful or not.

One skill I can point to is my ability, in major part thanks to the podcast, to build new relationships with smart and interesting people. This skill pairs well with, among other things, investing in search funds and I’ve been giving the idea a great deal of thought. Readers of my first and second articles on rolling funds saw some of my thinking. I’m still pondering the best angle to become an active investor, whether that’s investing my personal capital (albeit limited as a 23 year old), creating a rolling fund, syndicating, or working alongside a current search fund investor. I’d also love to hear your thoughts, dear reader, on this and if you have any ideas or insights to share on becoming an active participant.

Summing up, I will continue to grow the podcast both in number of episodes and quality of conversations. I’m a big admirer of Invest Like the Best and I strive to get Think Like an Owner to that same standard for the small company investing community. This space is fascinating and deserves far more attention than it gets. I hope the podcast is a positive contributor to the space and community. I want to thank all of you for your help, advice, time, wisdom, and generosity over the past 18 months since starting the podcast. I couldn’t get here without you all or get where I want to go and I want you to know how much your continued support means to me.

Think Like an Owner Sponsors

Live Oak Bank – Live Oak Bank is a seasoned SBA lender focused on search funds, independent sponsors, private equity firms, and individuals looking to acquire small companies. Live Oak has closed billions of dollars in SBA financing and is actively looking to help more small company investors across the country. If you are in the process of acquiring a company or thinking about starting a search, contact Live Oak directly to start a conversation at

Hood & Strong, LLP – Hood & Strong is a CPA firm with a long history of working with search funds and private equity firms on diligence, assurance, tax services, and more. Hood & Strong is highly skilled in working with search funds, providing quality of earnings and due diligence services during the search, along with assurance and tax services post-acquisition. They offer a unique way to approach acquisition diligence and manage costs effectively. To learn more about how Hood & Strong can help your search, acquisition, and beyond, please email one of their partners Jerry Zhou at

Barrel – Barrel is a digital marketing agency that helps companies create revenue-generating websites, emails, and marketing campaigns. Clients include L’Oreal, ScottsMiracle-Gro, Barry’s, and SmartyPants Vitamins. Barrel has extensive experience working with venture capital and private equity firms to help audit, optimize, and grow their portfolio brands. To learn more about Barrel, visit or email and mention Think Like an Owner podcast.

Interested in sponsoring?

Capital Notes

  • If you’re a current or past searcher, please consider filling out the searcher survey and sharing your experience with the community. The more searchers we can get responses from, the more new members to the search fund community can benefit.

  • Rich Jordan, who recently acquired a plumbing company, wrote this excellent Twitter thread about his experience building a team and getting buy-in from employees.

  • Joel Blake, who was recently on the podcast, has been making a few videos on SMB acquisitions and operations. Here’s one of him showing investors how to use LinkedIn to find targets.

If you found an interesting article, podcast, or interview that I missed, please let me know, I’m always looking for interesting stuff.


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I’m always looking to connect with folks interested in this space, don’t hesitate to reach out.