This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠

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This episode is brought to you by ⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠

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Today I'm joined by two of the most thoughtful, distinguished, and respected investors in the ETA ecosystem, Jeff Stevens and A.J. Wasserstein, to discuss the future of acquisition entrepreneurship. The paper that inspired this episode, written by both Jeff & A.J., can be accessed here:

Jeff Stevens is the Founder of Anacapa Partners, a firm with over 20 years of experience structuring, operating and investing in search fund-owned companies. Jeff was an acquisition entrepreneur himself, having managed 3 funded searches during the period from 1990-2005, each one culminating in the acquisition of a SMB.

A.J. Wasserstein is the Eugene F. Williams, Jr. Lecturer in the Practice of Management at the Yale School of Management. His research, writing, and teaching concentrates on search funds, entrepreneurship, programmatic acquisitions, and small businesses. In addition to his role as an educator, A.J. is also a private investor in lower middle-market businesses.

This episode is brought to you by ⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠

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This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠

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Today I'm joined by Michael Girdley, an entrepreneur and investor who has spent the past 30 years building a personal holding company boasting over $100M in annual revenue, comprised of 12 businesses across software, technology, consumer retail, and education, among others. Outside of managing his holding company, Michael is deeply involved in the North American SMB ecosystem: He co-hosts Acquisitions Anonymous, a podcast that reaches over 10,000 listeners weekly, where he and his co-hosts dissect real businesses currently up for sale. He also offers two online courses, educating prospective entrepreneurs on the Holding Company model, as well as best practices on how to find and acquire a great small business. He is also an active investor in small- and medium-sized software companies through another holding company, Dura Software, that invests in mission-critical B2B software companies spanning multiple niches.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠

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This episode is brought to you by ⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠

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Over many years of evaluating acquisition targets alongside searchers, I’ve found that certain questions tend to apply more often than not. I’ve presented each of these FAQs in today's episode, in hopes that they play a small role in how you structure your own due diligence process, and in turn how you think about the relative merits and risks of the opportunity in question. If you're a buyer, the list that follows can be thought of as a starting point for “Commercial Due Diligence 101”. If you're a seller, you should be prepared to address each of these questions and information requests if you're ever planning to sell your small to medium sized business. Please enjoy!

This episode is brought to you by ⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠

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This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses

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In today's episode, I will be speaking with 3 searchers, each of whom are at different stages of their respective search journeys. As I have done in the past, I will again be asking these guests only a single question: Knowing what you know now, if you could go back and re-do the first 90 days of your search, what might you do differently? This question is an important one because every searcher that I’ve ever met (including myself) learns so much along the way, and as a result we often reflect back on our first few months and wish we knew then what we know now. My hope is that this episode will help you learn from those who have come before you in this regard.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Symphony⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. ⁠⁠⁠⁠⁠Just go to ⁠⁠⁠⁠⁠the ⁠⁠⁠⁠Contact form on their website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and tell them that you’re a listener of the podcast to receive this discount!

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by ⁠⁠⁠⁠⁠⁠⁠August Felker⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 customers across a decade of operation, including countless searchers and CEOs within the ETA community

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Today I'm joined by Peter Lehrman, the Founder and CEO of Axial Market. For those of you who don’t know, Axial is the North America’s #1 online platform that connects buyers and sellers of small and medium sized businesses. Axial is used by over 20,000 investors, M&A advisors and CEOs, allowing them to connect on a confidential basis to explore M&A, debt, buyout, and growth equity transactions, to name just a few. Over 10,000 transactions are posted each year on Axial, covering companies that generate anywhere between $2.5M – $250M in revenue. Prior to Axial, Peter worked in private equity at SFW Capital Partners and was part of the founding team at Gerson Lehrman Group (or “GLG”, for short), a platform where investors and other users are able to connect on-demand with experts spanning a countless number of industries and disciplines.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Symphony⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. ⁠⁠⁠⁠Just go to ⁠⁠⁠⁠⁠the ⁠⁠⁠⁠Contact form on their website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and tell them that you’re a listener of the podcast to receive this discount!

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This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by ⁠⁠⁠⁠⁠⁠August Felker⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 customers across a decade of operation, including countless searchers and CEOs within the ETA community

Kaley Klemp is a highly sought after CEO coach, YPO forum facilitator, and best-selling author. In 2015, Kaley co-authored The 15 Commitments of Conscious Leadership, a book that was met with instant critical and commercial success, and followed that up in 2021 with The 80/80 Marriage, a book about how to strengthen and build relationships between spouses using some of the tools, techniques and ideas that she had previously employed with her executive coaching clients. Within the Young Presidents Organization (“YPO”), Kaley has facilitated retreats for more than 200 member and spouse forums throughout the world, and is a highly sought after speaker, recently having presented at Google alongside her husband, and with her TED Talk, “Stop Trying to Change”, racking up over 20 thousand views on YouTube. Prior to her coaching, speaking, and facilitator roles, Kaley was a management consultant with Deloitte, and prior to that she was a student at Stanford University, where she earned a B.A. in International Relations and an M.A. in Sociology, with a focus on Organizational Behaviour.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by ⁠⁠⁠⁠⁠⁠August Felker⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 customers across a decade of operation, including countless searchers and CEOs within the ETA community

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This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Symphony⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. ⁠⁠⁠Just go to ⁠⁠⁠⁠⁠the ⁠⁠⁠⁠Contact form on their website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and tell them that you’re a listener of the podcast to receive this discount!

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I have debated whether to write this blog post for quite some time now. Because topics related to mental health tend to generate more engagement than other more commercially-oriented content, I didn’t want this post to be interpreted as being hollow or self-promotional in any way, to the extent that it generates higher-than-normal clicks or page views for me. In spite of this, two things compelled me to finally publish this: (1) I wanted to simply discuss the topic of anxiety publicly, in hopes that my doing so will play some small role in helping others feel comfortable doing the same. (2) My hope is that some subset of