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In The Trenches

In The Trenches

By Steve Divitkos

The only podcast dedicated exclusively to Entrepreneurs and CEOs running Small to Medium Sized Businesses (SMB). Nobody knows what it’s like to be an Entrepreneur or CEO unless you’ve been one. Though many understand the rewards of company leadership, very few understand the arduous journey that’s required to get (and stay) there. I share my own lessons as an Entrepreneur and CEO, and interview experts spanning Sales, Leadership, Mental Health, M&A, and Operations (among others) all with a single goal: To improve the personal and professional lives of Entrepreneurs and CEOs running SMBs.
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Strategic Considerations When Evaluating a Letter of Intent to Sell Your Business

In The TrenchesAug 04, 2022

00:00
15:32
Evaluating Stock Options as Attraction, Retention, and Incentive Alignment Tools

Evaluating Stock Options as Attraction, Retention, and Incentive Alignment Tools

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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After many years of using company stock options as attraction, retention, and incentive alignment tools, I’ve come to appreciate their merits, risks, and possible alternatives. I intend to share these lessons with you today. More specifically though, I will argue that while options do have their time and place, there are often much simpler and less expensive alternatives that arguably have a greater impact on attraction, retention, and incentive alignment.

Mar 28, 202422:55
Can Ambition and Inner Peace Coexist? With Rob Dube

Can Ambition and Inner Peace Coexist? With Rob Dube

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 entrepreneur, CEO, and best-selling author, Rob Dube. In 1991, Rob co-founded imageOne, a managed print services business based in Oak Park, Michigan, that has won countless awards across countless publications for it’s growth, culture, and employee engagement, among many other accolades.

 

Today we discuss Rob's newest book, Shine: How Looking Inward Is the Key to Unlocking True Entrepreneurial Freedom. This book is all about how CEOs can manage their inner worlds, which stands in stark contrast to most business books, that focus almost exclusively on how CEOs can manage their outer-worlds. Rob co-authored the book alongside Gino Wickman, who is the author of the widely-read Traction, the book that introduced the world to the Entrepreneurial Operating System ("EOS").

Mar 14, 202401:26:39
Answers to Recurring FAQs from Current and Prospective Searchers

Answers to Recurring FAQs from Current and Prospective Searchers

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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Many searchers understandably tend to have very similar questions and areas of uncertainty. Indeed, in most instances, I had these very same questions and areas of uncertainty myself prior to raising my own search fund in 2012. As a result of the frequency with which I'm asked these questions, I've presented each of them in today's episode, and have also included my opinion on what the answers may be. Some of the questions include:

  • Constructing a cap table
  • Differences between the Canadian and US search ecosystems
  • Is the search fund market too crowded/saturated
  • The trade-off between price and business quality
  • What the best searchers do in their first 3-6 months
  • Proprietary vs. brokered deal flow generation
  • When to visit a prospective seller
  • Success rates of industry agnostic searches
  • Having an industry & geographic focus
  • Homogeneity among search investors re: industry preferences
  • How to spend your first week as a new CEO
  • Should I create a 100-day plan?
  • How to communicate the ownership change to customers
Feb 29, 202444:56
Profit Before Anything Else: With Mike Michalowicz, Author of "Profit First"

Profit Before Anything Else: With Mike Michalowicz, Author of "Profit First"

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 Entrepreneur, Investor, and Author Mike Michalowicz. In addition to being the author of 9 books, Mike is himself a serial entrepreneur, having founded, operated, and successfully exited several companies across his multi-decade career. He now spends much of his professional time writing, speaking, and coaching CEOs and entrepreneurs on the various systems that helped make him successful, including (and especially) his "Profit First" system, a highly tactical guide to organizing your entire company around achieving endurable profitability.

Feb 14, 202401:19:11
Royce Yudkoff & Rick Ruback: Educators, Mentors, and Leaders Within the SMB Community

Royce Yudkoff & Rick Ruback: Educators, Mentors, and Leaders Within the SMB Community

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 am thrilled to be joined by two guests that, without the risk of hyperbole, have changed my life in more ways than I can count. Royce Yudkoff & Rick Ruback are both professors at the Harvard business school, and co-teach two wildly popular courses called “The Financial Management of Smaller Firms” and “Entrepreneurship through Acquisition”, both of which focus on how to acquire, finance and operate your own smaller firm. They also co-published the widely read book, The HBR Guide to Buying a Small Business, published by Harvard Business Review Press, which acts as the definitive source of wisdom and guidance for a countless number of acquisition entrepreneurs


Feb 01, 202401:02:18
Jeff Stevens & A.J. Wasserstein on The Future of Entrepreneurship Through Acquisition

Jeff Stevens & A.J. Wasserstein on The Future of Entrepreneurship Through Acquisition

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.

Jan 18, 202401:32:45
Michael Girdley on The Rise of Holding Companies

Michael Girdley on The Rise of Holding Companies

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.

Jan 04, 202457:07
Questions You Should Be Prepared to Answer Before Buying (or Selling) a Small Business

Questions You Should Be Prepared to Answer Before Buying (or Selling) a Small Business

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!

Dec 21, 202329:04
What I'd Change if I Could Re-Do the First 90 Days of my Search: 3 Searcher Case Studies

What I'd Change if I Could Re-Do the First 90 Days of my Search: 3 Searcher Case Studies

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.

Dec 07, 202301:00:32
Dr. Victoria Medvec on the Art and Science of High Stakes Negotiations

Dr. Victoria Medvec on the Art and Science of High Stakes Negotiations

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

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Today I'm joined by Dr. Victoria Medvec, a Professor of Management and Organizations at the Kellogg School of Management at Northwestern University. In addition to her professorship, Dr. Medvec is the CEO of Medvec and Associates, a consulting firm focused on high stakes negotiations and strategic decisions. She is also the author of the best-selling book, Negotiate Without Fear, which was published in 2021. Dr. Medvec is a renowned global expert in the areas of negotiations, often advising senior executives and Boards of Directors from companies around the world. Her clients include IBM, Cisco, McKesson, General Electric, Merck, McKinsey, BlackRock, Goldman Sachs, McDonalds, Bristol Myers Squibb, and J.P. Morgan Chase, to name just a few.

Nov 23, 202301:35:24
Peter Lehrman, Founder & CEO of Axial, The Largest Online Marketplace to Buy & Sell SMBs

Peter Lehrman, Founder & CEO of Axial, The Largest Online Marketplace to Buy & Sell SMBs

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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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.

Nov 09, 202301:24:16
Conscious Leadership with Executive Coach and Best-Selling Author Kaley Klemp

Conscious Leadership with Executive Coach and Best-Selling Author Kaley Klemp

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


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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.

Oct 26, 202357:49
Building a $5.5B Mid-Market Private Equity Firm: Brent Belzberg, Founder of Torquest Partners

Building a $5.5B Mid-Market Private Equity Firm: Brent Belzberg, Founder of Torquest Partners

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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My guest today is Brent Belzberg, Founder and Senior Managing Partner of TorQuest, a middle market private equity firm that he founded in 2002 that has since grown to ~$5.5B in assets under management. In 2018, Brent was appointed as a Member of the Order of Canada, Canada’s highest civilian honor, for his work as a business leader and philanthropist. He also received Queen Elizabeth II’s Platinum Jubilee Medal in 2023 for his significant contribution to Canada and the province of Alberta.

Oct 12, 202301:16:24
My Experience With Anxiety

My Experience With Anxiety

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


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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 readers will respond to some subset of the points below with a nod of their heads, and a sentiment of “Yes, I’ve felt something similar myself”.

Sep 28, 202324:21
A Deep Dive on Compensation

A Deep Dive on Compensation

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 spent the past several weeks going through almost 3 years of In The Trenches archives to tease out all of the best insights that we’ve been able to collect from each of our guests specific to Compensation. I won’t need to convince any CEO of how important compensation is, and how fraught with peril it can be when it isn’t done right. Below is a list of our guests and topics, which include timestamps, so you can skip between the segments that are most interesting to you:

  • (3:06) Verne Harnish: Crafting Company-Wide Compensation Plans
  • (20:55) Dave Prusinski: Sales Compensation
  • (37:48) Rich Manders & Brent Beshore: Equity or Options as a Form of Compensation
  • (51:00) Jim Sharpe: Managing Wage Inflation & Salary Expectations
  • (55:05) Randy Street: Surprising Lessons Specific to Compensation
  • (1:03:05) Bob Pritchett: Compensation Mistakes
Sep 14, 202301:07:02
A Deep Dive on Hiring

A Deep Dive on Hiring

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Symphony⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. On September 8th, 2023, Symphony will be live-streaming a webinar on searchfunder.com all about the technical due diligence process when acquiring a software company. Use this link to sign up: ⁠https://www.searchfunder.com/event/view/1200⁠. 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 * I have spent the past several weeks going through almost 3 years of In The Trenches archives to tease out all of the best insights that we’ve been able to collect from each of our guests specific to Hiring. I won’t need to convince any CEO of how important the hiring process is, and how fraught with peril it can be when it isn’t done right. Below is a list of our guests and topics, which include timestamps, so you can skip between the segments that are most interesting to you: (3:30) Randy Street: Co-author of Who: The A Method for Hiring, which introduced the Topgrading hiring method to the world (22:39) Verne Harnish: Founder of the Entrepreneurs’ Organization (“EO”), & author of Mastering the Rockefeller Habits and Scaling Up (37:43) AJ Wasserstein: Professor at the Yale School of Management. Prior 2x CEO and active SMB investor (43:40) Mike Zani: CEO of The Predictive Index, and author of The Science of Dream Teams (52:27) Steve Divitkos: Hiring Your Senior Management Team: Founder of Mineola Search Partners (1:12:50) Anthemos Georgiades: Hiring in High Growth Environments: Founder and CEO of Zumper, an apartment rental platform that boasts 250 employees, 75 million active users, and 17 million app visits per month (1:27:09) Nicholas Andrews: Hiring for the Finance & Accounting Function: Founder of The Aspen Consulting Group (1:42:40) Rich Mironov: Hiring in Product Management: One of North America’s preeminent Product Management thought leaders, having spent 40 years in the software industry in numerous capacities (1:55:20) Dave Prusinski: Hiring in Sales: Former EVP of FleetComplete. Grew annual revenue by ~25x, achieving a ~50% revenue CAGR for 9 of his 10 years

Aug 31, 202302:16:58
"A Guide to the Good Life": What Entrepreneurs Can Learn From Stoic Philosophy

"A Guide to the Good Life": What Entrepreneurs Can Learn From Stoic Philosophy

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. On September 8th, 2023, Symphony will be live-streaming a webinar on searchfunder.com all about the technical due diligence process when acquiring a software company. Use this link to sign up: https://www.searchfunder.com/event/view/1200. 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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My guest today is Dr. William Irvine, author of the best-selling book A Guide to the Good Life: The Ancient Art of Stoic Joy, and one of the world's most influential writers on, and practitioners of, stoic philosophy. Dr. Irvine spent 38 years teaching at Wright State University in Dayton, Ohio, having recently earned Professor Emeritus status there. Dr. Irvine earned his BA in Mathematics and Philosophy from the University of Michigan and an MA and PhD in Philosophy at UCLA.

Aug 17, 202301:19:50
Venture Capital “Orphans”: Exploring an Emerging Search Fund Investment Thesis

Venture Capital “Orphans”: Exploring an Emerging Search Fund Investment Thesis

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠Symphony⁠⁠⁠⁠⁠⁠⁠⁠⁠. On September 8th, 2023, Symphony will be live-streaming a webinar on searchfunder.com all about the technical due diligence process when acquiring a software company. Use this link to sign up: https://www.searchfunder.com/event/view/1200. 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


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Recently, searchers have voiced an increasing level of interest in targeting “VC orphan” companies as acquisition targets: These tend to be healthy and modestly growing companies that have raised at least one round of institutional venture capital, have achieved product/market fit, but have failed to produce the triple-digit growth rates that are all but required for them to continue to command the time, attention, and capital of their VC-backers. Might searchers also consider this very different company profile, in addition to that which has served as the foundation of the Search Fund investment vehicle over the past three decades? Today's episode attempts to explore this question, presenting observations that both support and refute the thesis.

Aug 03, 202317:00
When Search Funds Don’t Go As Planned (Part 2): With Jim Sharpe

When Search Funds Don’t Go As Planned (Part 2): With Jim Sharpe

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.



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Today’s episode is the second in a two-part series on when search funds don’t go as originally planned. On last week’s episode, we spoke with four entrepreneurs to get a first-hand account of how and why their paths deviated from their original plans. In today’s episode, we look to compliment those first-hand accounts with reflections from Jim Sharpe, a highly respected search fund investor of almost 20 years, and himself a former Searcher and CEO. Today we ask Jim to discusses the trends, commonalities, and themes that he has observed among searchers who failed to consummate an acquisition, and also those who did consummate an acquisition, but failed to "thrive" thereafter, either commercially or personally. Please enjoy!
Jul 22, 202301:02:56
Lessons Learned From 400+ Post-Exit Entrepreneurs: John Warrillow, Host of Built to Sell Radio

Lessons Learned From 400+ Post-Exit Entrepreneurs: John Warrillow, Host of Built to Sell Radio

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. * 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! * My guest today is John Warrillow, author of the bestselling book Built to Sell: Creating a Business That Can Thrive Without You, and Founder & CEO of The Value Builder System, a sales and marketing software tool for business advisors to find, win and keep their best clients. Built to Sell was recognized by both Fortune and Inc magazines as one of the best business books of 2011, and has been translated into 12 languages since its initial publication. John is also the author of The Automatic Customer: Creating a Subscription Business in Any Industry and The Art of Selling Your Business: Winning Strategies & Secret Hacks for Exiting on Top. John is also the host of Built to Sell Radio, a hugely popular podcast where he has interviewed over 400 SMB founders about their exits. Forbes ranked Built to Sell Radio as one of the ten best podcasts for business owners. Before founding The Value Builder System, John started and successfully exited four companies.
Jul 22, 202353:44
When Search Funds Don't Go As Planned (Part 1): 3 Searcher Case Studies

When Search Funds Don't Go As Planned (Part 1): 3 Searcher Case Studies

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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If one were to attend a randomly selected group of Search Fund conferences, they'd be forgiven for thinking that every search fund is a smashing success. When I was both a searcher and a CEO, I often left these types of events with a certain sense of insecurity and self-doubt, as everybody seemed to be more successful, more confident in their abilities, and more decisive in their actions. Yet, the data does not at all support the idea that everybody seems to be doing better than you are: One-third of search funds reliably fail to acquire a business, and of those that do, roughly one-third of them fail to return more than 1.0x the original capital. In today's episode, we speak with four entrepreneurs whose ETA paths deviated from their original plans, not only to learn from their hard-earned wisdom, but also to celebrate their courage and the wonderful professional successes that they've all gone on to achieve since.
Jun 22, 202301:54:01
75 Things That I Think Are True

75 Things That I Think Are True

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. * Like many of you, I’m a sucker for a good quote. The best quotes often distill a lifetime of wisdom into only a few words, which is likely why some of them continue to resonate for decades (and in some instances, even centuries) after first being articulated. Over the years, I’ve compiled quotes from countless books, mentors, podcasts, and blogs, and in today's episode, I present this collection of quotes to you, in hopes that some of them impact you as much as they’ve impacted me. Most importantly though, I’m proud to finally be able to tell my wife that all of those years of highlighting books in bed have finally led to a tangible piece of output. Please enjoy!


Jun 08, 202322:19
The SMB Credit Markets: Bank Failures, Rising Interest Rates, and a Looming Recession

The SMB Credit Markets: Bank Failures, Rising Interest Rates, and a Looming Recession

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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To say that it's been an active 6-12 months in the banking sector would be an understatement: Beginning as recently as January, 2022, we've seen the US Federal Funds rate increase from .08% to 4.83%, the rapid collapse of Silicon Valley Bank, and the rescue of First Republic Bank by JPMorgan, representing the second largest bank failure in the history of the United States. Against this backdrop, CEOs and prospective acquirors of small businesses understandably have a lot of questions about their banking partners, their ability to secure loans, and the terms under which they might be able to do so. To get us up to speed on the state of lower-middle-market credit in North America, I'm joined by Anthony Rodriguez and Conor Tidgewell of Avidbank, who walk us through what has changed, the "new normal", and what it all means for entrepreneurs and CEOs running (or seeking to acquire) a small business. Please Enjoy!


May 25, 202301:09:36
The Merits, Risks, and Possible Unintended Consequences of Earn-Outs

The Merits, Risks, and Possible Unintended Consequences of Earn-Outs

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.


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When acquiring small to medium sized businesses, buyers often utilize a tool called an “earn-out”, which is a form of contingent consideration that sellers may receive at some point in the future in addition to the cash that they stand to receive at closing. Though earn-outs can be useful and mutually beneficial tools for both buyers and sellers under the right circumstances, without careful structuring and consideration they can fraught with risk and unintended consequences.

Before you propose an earn-out as part of your own acquisition, I’d encourage you to think through some of the risks and considerations that we discuss in today's episode. Please enjoy!

May 11, 202323:10
Mental Health for High Achievers: Ambition, Anxiety, Perfectionism, and Balancing Striving vs. Self-Acceptance

Mental Health for High Achievers: Ambition, Anxiety, Perfectionism, and Balancing Striving vs. Self-Acceptance

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 ⁠Avidbank⁠. Avidbank is one of the most experienced search fund lenders in North America, having funded over 40 separate transactions since 2014, for a total of over $300M. They are deeply familiar with the search fund model, and understand the nuances of the fundraising process, dealing with sellers, communicating with your equity investors, LOI reviews, and everything else in between. Reach out to Anthony Rodriguez (arodriguez@avidbank.com) or Conor Tidgwell (ctidgwell@avidbank.com) to learn more.


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My guest this week is Andy Johns, whose memoirs could be titled "a tale of two careers". In his "first" career, Andy was an executive within the start-up and technology ecosystems, with growth and product oriented leadership roles at Facebook, Twitter, and Quora, among others. Following his time at these three companies, Andy became VP of Growth, VP of Product, and eventually President at Wealthfront, an automated investment platform that currently boasts $27 billion AUM across 470,000 accounts.


Now, in his second act, Andy spends his time helping others heal from emotional pain, transform themselves, and discover their life purpose. He is the Founder of clues.life, an online collection of wisdom, information, stories, and research on mental health, personal transformation, and the pursuit of meaning and purpose. He is also the author of a very popular substack, where he writes about the mental health struggles often faced by high achievers like himself.


Apr 27, 202301:34:48
The 2023 SaaS CEO Survey

The 2023 SaaS CEO Survey

This episode is brought to you by ⁠⁠Avidbank⁠⁠. Avidbank is one of the most experienced search fund lenders in North America, having funded over 40 separate transactions since 2014, for a total of over $300M. They are deeply familiar with the search fund model, and understand the nuances of the fundraising process, dealing with sellers, communicating with your equity investors, LOI reviews, and everything else in between. Reach out to Anthony Rodriguez (arodriguez@avidbank.com) or Conor Tidgwell (ctidgwell@avidbank.com) to learn more.

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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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Though search funds have historically acquired companies within countless different industries, software has been among the most popular and sought-after industries among searchers for many years now. Because of this, I chose to conduct a survey of SaaS CEOs (who became owners/CEOs by way of the search fund model) for two reasons: (1) To better understand the complexion of the "typical" software acquisition within the search fund ecosystem; & (2) To see whether or not the the complexion of the "typical" software acquisition has changed over time.


As you will see from the data presented in today's episode, I feel safe in concluding that, yes, the profile of the typical SaaS acquisition has indeed changed over the past few years, in some cases quite materially. Today's episode will walk you through how and why I arrived at this conclusion.


*Special Note for today's episode*: Because this post is necessarily heavily on stats and graphs, I would strongly suggest viewing the blog post (as I can only verbally describe graphs so well!), which you can find at this link.

Apr 13, 202334:37
Kent Weaver: Building, Working With, and Learning from your Board of Directors

Kent Weaver: Building, Working With, and Learning from your Board of Directors

This episode is brought to you by The Profit Line.  The Profit Line is a boutique finance and accounting firm that provides a wide range of accounting services to small and medium businesses generating anywhere between $5M to $50M in revenue. On a fractional, outsourced basis, they do day-to-day bookkeeping, bank reconciliations, month-end accruals, tax compliance, and financial statement preparation, among countless other things. I was a customer of theirs for 7 consecutive years while running my own company,  and am speaking as a happy customer. Book a call with Founder and CEO, Fern Gordon (Ferngordon@theprofitline.com) or visit their LinkedIn page to learn how they might be able to help you exactly as they helped me.

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This episode is brought to you by Avidbank. Avidbank is one of the most experienced search fund lenders in North America, having funded over 40 separate transactions since 2014, for a total of over $300M. They are deeply familiar with the search fund model, and understand the nuances of the fundraising process, dealing with sellers, communicating with your equity investors, LOI reviews, and everything else in between. Reach out to Anthony Rodriguez (arodriguez@avidbank.com) or Conor Tidgwell (ctidgwell@avidbank.com) to learn more.

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Today, I'm joined by Kent Weaver, somebody who has decades of experience serving on the Boards of SMBs. Kent is an acquisition entrepreneur himself, having acquired a Sacramento-based health care business after a ~2 year search. After running the company for close to 9 years, he exited successfully, and has been investing in SMBs ever since. He has invested in over 150 search funds and 80 operating businesses, and has served on over 25 boards spanning health care, software, business services and consolidation strategies. Given Kent’s depth of governance experience, I thought he’d make a great resource for current or prospective CEOs who might be wrestling with questions related to how to construct, communicate with, and learn from their own Boards. Please enjoy!


Mar 29, 202355:26
How to Know When it's Time to Stop

How to Know When it's Time to Stop

It's not hard to understand the importance of persistence to the entrepreneurial journey. Entrepreneurs who overcome substantial hardships on their eventual road to success are (rightly) applauded for the otherworldly persistence that they demonstrated in doing so.

Yet many entrepreneurs are able to finally achieve success only after moving on from several prior ventures whose prospects eventually grew to become much less promising. These entrepreneurs are also (rightly) applauded, though this time it’s for the foresight, objectivity and courage that they demonstrated in making what must have been an incredibly difficult decision to “quit”.

So, which is it? Should entrepreneurs persist at substantially any cost, or should they be wise enough to know when they’d be better off doing something else entirely? How does one know when to perceive persistence as an asset, and when to perceive it as a liability?

In late-2020, I decided to step down as the CEO of my own company after approximately 7 years at the helm. Since then, I have spoken to countless entrepreneurs and CEOs wrestling with similar decisions. In each instance, they asked how I made my decision, which is why I’ve decided to write this post.

Though I can’t tell you specifically what you should do, I can at least share with you the questions that I asked of myself in coming to my own decision.
Mar 22, 202317:56
Are You Selling to the Wrong Customers?

Are You Selling to the Wrong Customers?

This episode is brought to you by Avidbank. Avidbank is one of the most experienced search fund lenders in North America, having funded over 40 separate transactions since 2014, for a total of over $300M. They are deeply familiar with the search fund model, and understand the nuances of the fundraising process, dealing with sellers, communicating with your equity investors, LOI reviews, and everything else in between. Reach out to Anthony Rodriguez (arodriguez@avidbank.com) or Conor Tidgwell (ctidgwell@avidbank.com) to learn more.

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This episode is brought to you by The Profit Line.  The Profit Line is a boutique finance and accounting firm that provides a wide range of accounting services to small and medium businesses generating anywhere between $5M to $50M in revenue. On a fractional, outsourced basis, they do day-to-day bookkeeping, bank reconciliations, month-end accruals, tax compliance, and financial statement preparation, among countless other things. I was a customer of theirs for 7 consecutive years while running my own company,  and am speaking as a happy customer. Book a call with Founder and CEO, Fern Gordon (Ferngordon@theprofitline.com) or visit their LinkedIn page to learn how they might be able to help you exactly as they helped me.

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Among the countless strategic decisions that software CEOs must make, the decision of which end markets to serve doesn’t seem to command the time, attention, and level of thoughtfulness that it probably should. More specifically, substantially every small or medium-sized software company must answer the following two questions:

  1. Should I sell to SMBs or to larger enterprises?
  2. Should I sell my product into a single industry vertical, or multiple industry verticals?

Though these are of course not the only questions that software CEOs must answer with respect to the markets that they serve, they tend to be among the most important and most frequently posed ones. The purpose of this blog is to speak to both of these questions in turn.

Mar 16, 202328:04
Everything You've Ever Wanted to Know About Working with a Partner: With Dr. Noam Wasserman, Author of The Founder's Dilemmas

Everything You've Ever Wanted to Know About Working with a Partner: With Dr. Noam Wasserman, Author of The Founder's Dilemmas

This episode is brought to you by The Profit Line.  The Profit Line is a boutique finance and accounting firm that provides a wide range of accounting services to small and medium businesses generating anywhere between $5M to $50M in revenue. On a fractional, outsourced basis, they do day-to-day bookkeeping, bank reconciliations, month-end accruals, tax compliance, and financial statement preparation, among countless other things. I was a customer of theirs for 7 consecutive years while running my own company,  and am speaking as a happy customer. Book a call with Founder and CEO, Fern Gordon (Ferngordon@theprofitline.com) or visit their LinkedIn page to learn how they might be able to help you exactly as they helped me.

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This episode is brought to you by Avidbank. Avidbank is one of the most experienced search fund lenders in North America, having funded over 40 separate transactions since 2014, for a total of over $300M. They are deeply familiar with the search fund model, and understand the nuances of the fundraising process, dealing with sellers, communicating with your equity investors, LOI reviews, and everything else in between. Reach out to Anthony Rodriguez (arodriguez@avidbank.com) or Conor Tidgwell (ctidgwell@avidbank.com) to learn more. 

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My guest today is Dr. Noam Wasserman, recognized as one of the world's foremost experts in how to form and maintain high performing partnerships in entrepreneurial contexts. Dr. Wasserman is currently the Dean of the Sy Syms School of Business at Yeshiva University in New York City, and was previously a professor at Harvard Business School for 13 years. His now famous book, The Founder’s Dilemmas, quickly became an Amazon #1 bestseller, and has since won countless awards. In our conversation today, we discuss what to consider when seeking out a partner, the important conversations that prospective partners ought to have with each other, what role passion and persistence should play in the entrepreneurial journey, and how to apply his various concepts and frameworks to our personal lives.

Mar 02, 202301:37:54
Evaluating the Correlation Between Hours Worked and Success Achieved

Evaluating the Correlation Between Hours Worked and Success Achieved

This episode is brought to you by The Profit Line.  The Profit Line is a boutique finance and accounting firm that provides a wide range of accounting services to small and medium businesses generating anywhere between $5M to $50M in revenue. On a fractional, outsourced basis, they do day-to-day bookkeeping, bank reconciliations, month-end accruals, tax compliance, and financial statement preparation, among countless other things. I was a customer of theirs for 7 consecutive years while running my own company,  and am speaking as a happy customer. Book a call with Founder and CEO, Fern Gordon (Ferngordon@theprofitline.com) or visit their LinkedIn page to learn how they might be able to help you exactly as they helped me.


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This episode is brought to you by Warren Coughlin, CEO Coach and founder of JumpStart Coaching. Warren focuses exclusively on coaching CEOs running SMBs, and has been doing so for over 20 years. One of my biggest regrets across my 7 years as a CEO was not hiring a coach, and I want to prevent others from making the same mistake. For listeners of In The Trenches, working with Warren is effectively risk-free: If at the end of the first three months you're not happy with the direction of your business, he will give you your money back. On top of that, Warren is offering $3,000 off of his coaching program for listeners of In The Trenches. Just go to warrencoughlin.com/trenches to learn more. 


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Though there are countless books, blogs, podcasts, and social media accounts that serve as thoughtful and informative resources for current and prospective entrepreneurs, unfortunately there appears to be an equal number of resources that demonstrate seemingly no limit to the fundamentally bad advice that they’re willing to impart upon others. "Hustle Culture" has unfortunately become so prevalent online that I felt it necessary to provide the entrepreneurial community with my own perspective on the matter.

Feb 16, 202314:38
The Smallest Changes That Had The Largest Impacts: 4 CEO Case Studies

The Smallest Changes That Had The Largest Impacts: 4 CEO Case Studies

This episode is brought to you by The Profit Line.  The Profit Line is a boutique finance and accounting firm that provides a wide range of accounting services to small and medium businesses generating anywhere between $5M to $50M in revenue. On a fractional, outsourced basis, they do day-to-day bookkeeping, bank reconciliations, month-end accruals, tax compliance, and financial statement preparation, among countless other things. I was a customer of theirs for 7 consecutive years while running my own company,  and am speaking as a happy customer. Book a call with Founder and CEO, Fern Gordon (Ferngordon@theprofitline.com) or visit their LinkedIn page to learn how they might be able to help you exactly as they helped me. 

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This episode is brought to you by Warren Coughlin, CEO Coach and founder of JumpStart Coaching. Warren focuses exclusively on coaching CEOs running SMBs, and has been doing so for over 20 years. One of my biggest regrets across my 7 years as a CEO was not hiring a coach, and I want to prevent others from making the same mistake. For listeners of In The Trenches, working with Warren is effectively risk-free: If at the end of the first three months you're not happy with the direction of your business, he will give you your money back. On top of that, Warren is offering $3,000 off of his coaching program for listeners of In The Trenches. Just go to warrencoughlin.com/trenches to learn more.

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This is a very special episode of In The Trenches: In today’s episode, I will be interviewing 4 different CEOs of 4 different SMBs, and asking them just a single question: "What are some of the seemingly small changes you’ve made that have had the largest impacts?"


When taking over a new business, new CEOs often speak of operational “low hanging fruit”, so I wanted to ask this same question to 4 different CEOs to learn more about just what this low hanging fruit is.


Each CEO that I’ll be speaking with today is at a different stage of their journey: Betsy, who I’ll begin the episode with, is still in her first year in the CEO seat. Sheret, our next leader, has been CEO of his company for ~2 years. Robin Kovitz has been leading her company for ~8 years, and finally Adrian, our final CEO, ran his company for ~7 years before a successful exit to a strategic acquiror in 2019.


Does growth and success tend to result from a large number of seemingly small changes, or a small number or larger changes? That’s what we’ll endeavor to answer today, informed by 4 CEOs at very different stages of their respective journeys.

Feb 02, 202301:30:28
Constructing, Managing, and Working with a Board of Directors

Constructing, Managing, and Working with a Board of Directors

This episode is brought to you by Warren Coughlin, CEO Coach and founder of JumpStart Coaching. Warren focuses exclusively on coaching CEOs running SMBs, and has been doing so for over 20 years. One of my biggest regrets across my 7 years as a CEO was not hiring a coach, and I want to prevent others from making the same mistake. For listeners of In The Trenches, working with Warren is effectively risk-free: If at the end of the first three months you're not happy with the direction of your business, he will give you your money back. On top of that, Warren is offering $3,000 off of his coaching program for listeners of In The Trenches. Just go to warrencoughlin.com/trenches to learn more.


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This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report.  Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else. Cayne Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them.


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CEOs running newly public companies, those who have raised external equity for the first time, and those occupying the CEO seat for the first-time are often intimidated by the idea of reporting into a Board, and are uncertain of how to construct, manage, communicate with, and learn from them. This combination of uncertainty and inexperience often creates undue stress for CEOs, and can create situations in which they are more focused on impressing their Boards than they are on leaning on them for support, guidance, and mentorship.

Over many years as a CEO reporting directly into a Board (and now as an investor who sits on Boards and works directly with CEOs myself), I’ve come to learn a few things about how to construct, manage, communicate with, and learn from this critically important group of people.

This episode is my best attempt at sharing these lessons with you. 

Jan 19, 202321:30
Mike Zani, CEO of The Predictive Index: Hiring, Personality Profiling Tools, Working with a Partner, and Other Lessons from 20 Years as a CEO

Mike Zani, CEO of The Predictive Index: Hiring, Personality Profiling Tools, Working with a Partner, and Other Lessons from 20 Years as a CEO

This episode is brought to you by Warren Coughlin, CEO Coach and founder of JumpStart Coaching. Warren focuses exclusively on coaching CEOs running SMBs, and has been doing so for over 20 years. One of my biggest regrets across my 7 years as a CEO was not hiring a coach, and I want to prevent others from making the same mistake. For listeners of In The Trenches, working with Warren is effectively risk-free: If at the end of the first three months you're not happy with the direction of your business, he will give you your money back. On top of that, Warren is offering $3,000 off of his coaching program for listeners of In The Trenches. Just go to warrencoughlin.com/trenches to learn more.

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This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report.  Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else. Cayne Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them.

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My guest today is Mike Zani, CEO of The Predictive Index. The Predictive Index serves more than 9,000 clients across 142 countries, helping businesses optimize their hiring and team composition decisions through behavioral science, software, and professional consulting from the world's top workplace behavioral specialists. Mike has been CEO of The Predictive Index for approximately 8 years, after having purchased the business from its original founders. Prior to leading The Predictive Index, Mike successfully purchased, operated, and sold two other companies in the employee wellness and manufacturing industries.


The Predictive Index is one of the most widely-used personality profiling tools utilized by SMB CEOs when making hiring decisions, and in today's discussion we discuss these types of tools at length: When they're most useful (and when they're not), the most frequent sources of hiring mistakes, how transferable they are to blue collar industries, how we might utilize them in our personal relationships, and how he would utilize similar tools if looking to buy another business, to name just a few.


Please enjoy!  

Jan 05, 202301:30:53
The Current State of the Debt Capital Markets

The Current State of the Debt Capital Markets

This episode is brought to you by Warren Coughlin, CEO Coach and founder of JumpStart Coaching. Warren focuses exclusively on coaching CEOs running SMBs, and has been doing so for over 20 years. One of my biggest regrets across my 7 years as a CEO was not hiring a coach, and to the best extent possible, I want to prevent others from making the same mistake. For listeners of In The Trenches, working with Warren is effectively risk-free: If at the end of the first three months you're not happy with the direction of your business, he will give you your money back. If that doesn’t say confidence, I don’t know what does. On top of that, Warren is offering $3,000 off of his coaching program for listeners of In The Trenches. Just go to warrencoughlin.com/trenches to learn more. 


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This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report.  Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else. Cayne Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them.

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This episode attempts to directly address many of the questions that I’ve been asked over the past 6 months related to the current state of the debt markets: How pricing has changed, how credit availability has evolved, what risks banks are no longer willing to underwrite, how their diligence processes have changed, how non-price terms have evolved, and so on. To help me better understand the current state of the debt markets, I reached out to Cory Kaiser and Tim Eaton, both of whom work at TD in their commercial lending group: Cory is Vice President of commercial banking and has been with TD for over 21 years, and Tim is an associate vice president, who has been with TD for 23 years. Over the past two decades, their focus has been (and will continue to be) on lending to lower-middle market private companies, not just to finance their acquisitions, but also to finance growth, working capital, and recapitalizations, to name just a few. I hope this episode helps to clarify some of the questions that you might be wrestling with yourself. Please enjoy!

Dec 22, 202259:39
Evaluating 5 Very Different Approaches to Acquiring a Software Company

Evaluating 5 Very Different Approaches to Acquiring a Software Company

This episode is brought to you by Warren Coughlin, CEO Coach and founder of JumpStart Coaching. Warren focuses exclusively on coaching CEOs running SMBs, and has been doing so for over 20 years. One of my biggest regrets across my 7 years as a CEO was not hiring a coach, and to the best extent possible, I want to prevent others from making the same mistake. For listeners of In The Trenches, working with Warren is effectively risk-free: If at the end of the first three months you're not happy with the direction of your business, he will give you your money back. If that doesn’t say confidence, I don’t know what does. On top of that, Warren is offering $3,000 off of his coaching program for listeners of In The Trenches. Just go to warrencoughlin.com/trenches to learn more. 

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This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report.  Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else. Cayne Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them.

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Enterprise software is considered to be among the world’s best business models. However, getting access to the world’s best business model doesn’t come cheaply: Software businesses most frequently trade at multiples of recurring revenue, which stands in contrast to most other industries in which businesses tend to trade at multiples of EBITDA or cash flow. 

But not all software investment theses are created equally: There are indeed several different approaches to acquiring and building a software company, and each approach presents a different investment thesis, requires different operational and value creation strategies, and is likely to command different asking prices. In today's episode, I present and evaluate 5 very different approaches that buyers might consider in their pursuit of a software business. Though this list of approaches is by no means exhaustive, it does capture those that I tend to see most frequently. 

Please enjoy!

Dec 08, 202230:36
Brent Beshore: The "Forrest Gump of Private Equity"

Brent Beshore: The "Forrest Gump of Private Equity"

This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report. I have personally read though, analyzed, and relied upon several of their actual QofE reports in my capacity as an SMB investor, and can personally attest to the quality of the work that they do. Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else.

Cayne Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them.

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My guest today is Brent Beshore. Brent is Founder and CEO of Permanent Equity, a private investment firm that invests in Founder-owned private companies. Permanent Equity is a (very) long-term investor that typically intends to hold portfolio companies indefinitely, often without the use of any leverage.

In addition to his role as an investor, Brent is also a prolific writer: He is a regular contributor to Forbes, and also publishes and releases materials for free on Permanent Equity's website, spanning topics like operating, selling, and investingin SMBs, among others. Brent is also the author of The Messy Marketplace, a book that aims to demystify the process of selling a company.

I must say that this conversation was a real pleasure for me to have. Brent is a really thoughtful guy who has a lot of really unique and insightful views on buying, running, and selling SMBs. And, of all the many conversations that I’ve had recently, this one might cover the most ground: So strap in for a very wide-ranging discussion, and please enjoy. 

Nov 24, 202201:27:10
Tools in Managing my own Psychology

Tools in Managing my own Psychology

This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report. I have personally read though, analyzed, and relied upon several of their actual QofE reports in my capacity as an SMB investor, and can personally attest to the quality of the work that they do. Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else.

Cayne Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them.

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In today’s episode I get unapologetically tactical, and discuss the specific tools, routines, and practices that I have found to be particularly effective in managing my own psychology as an entrepreneur and CEO. I chose to write about this topic based on the following three deeply held beliefs: (1) A CEO’s ability to manage herself is at least as important as, if not more important than, her ability to manage her business; (2) Unless you are deliberate about managing your own psychology, you risk becoming a sort of “victim” to the circumstances that happen to present themselves in your life at any given time; & (3) Over time, the mood of the broader employee base often directly reflects that of the leader. 

I hope at least some of these prove to be helpful for you


Nov 10, 202222:33
A.J. Wasserstein: Reflections of a Founder, CEO, Investor and Educator

A.J. Wasserstein: Reflections of a Founder, CEO, Investor and Educator

This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report. I have personally read though, analyzed, and relied upon several of their actual QofE reports in my capacity as an SMB investor, and can personally attest to the quality of the work that they do. Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else.

Cayne Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them.

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My guest today is A.J. Wasserstein, 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. He was the President of Onesource Water, the third-largest bottleless water service business in the U.S., which was sold to Water Logic, a U.K.-based strategic acquirer, in 2016. Previously, A.J. was the founder and CEO of ArchivesOne, the third largest records management company in the U.S. ArchivesOne was sold to Iron Mountain (NYSE: IRM) after 17 years of operation.

A.J.'s incredible collection of writing can be accessed here.

Oct 27, 202201:13:42
The CEO as Chief Capital Allocator

The CEO as Chief Capital Allocator

This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report. I have personally read though, analyzed, and relied upon several of their actual QofE reports in my capacity as an SMB investor, and can personally attest to the quality of the work that they do. Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else.  

Cayne Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them. 

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Episode Description: Relative to its importance, capital allocation seems to be a relatively under-discussed subject among SMB CEOs. The subject is at least as important as more common day-to-day issues like hiring, culture, or compensation, though it rarely seems to occupy the same share-of-mind. Though capital allocation isn't a discipline that CEOs consciously or explicitly deprioritize, it often loses the battle for their time and attention when competing with more common day-to-day issues like those mentioned above.  

As a CEO you’d be wise to regularly look at your business through the lens of an investor to ensure that you’re allocating your company’s scarce financial resources towards their highest and best use. In today's episode, I discuss some relevant lessons that I’ve collected over the years related to capital allocation, some of which I hope are helpful to you.

Oct 13, 202220:24
Buy at 5X EBITDA, Sell at 8X Revenue: The On-Premise to SaaS Transition of FieldEdge

Buy at 5X EBITDA, Sell at 8X Revenue: The On-Premise to SaaS Transition of FieldEdge

My guests today are Steve Lau and Rameez Ansari, co-CEOs of AutoLeap, a software company that services auto repair shops, that counts Bain Capital Ventures among its investors.


Prior to founding AutoLeap, Steve and Rameez purchased, operated, and sold D'Esco (later renamed FieldEdge), a software company that helps entrepreneurs run their HVAC, Plumbing, and Electrical Contracting businesses. Steve and Rameez purchased the company from its original founder in 2015 at 5X EBITDA, when its product was entirely on-premise and its revenue was generated solely through the sale of perpetual use licenses. After successfully transitioning the company to one that sold a cloud-based product and generated revenue on a subscription basis, they sold the company to a private equity firm for 8X revenue in 2019.


For the past 5-10 years, investors have salivated over the return potential inherent in transitioning a sticky enterprise software product with low customer churn from on-premise to SaaS. Though returns like those generated by Steve and Rameez certainly illustrate that such transitions can be successfully made, the headlines often ignore how brutally difficult this transition tends to be, both operationally and financially.


Though software investors and operators will find this episode relevant for what are probably obvious reasons, I’d also suggest that any CEO, in any industry, ought to pay attention to the lessons that Steve & Rameez learned, especially if they’re considering a transformation of any sort within their own companies. We talk about shifts in organizational culture, changes in salesforce compensation, how to communicate the need for change within a company, how to respect the history and legacy of a business while still keeping an eye towards the future, how non-technical CEOs can run a technically-oriented business, and much much more.

Sep 29, 202201:18:50
Knowing Who, When, and How to Fire

Knowing Who, When, and How to Fire

Unfortunate at this reality may be, I would argue that firing (specifically knowing who, when, and how to fire) is a required core competency for any CEO, and is arguably as important as hiring, communication, capital allocation, and other tools within the CEO’s toolkit. The extent to which this is an unpleasant (and perhaps even unpopular) topic to discuss doesn’t negate its critical importance in building and sustaining a healthy and vibrant company.

Some may associate the idea of firing with toxic, authoritarian, or fear-based work cultures. While firing can lead to these types of outcomes if done in an arbitrary, thoughtless, or fear-inducing way, if and when done correctly, it can actually become one of the CEO’s primary tools in building a healthy, inclusive, fair and meritocratic culture.

It’s important for me to note that this isn’t because firing itself is value-creating. It clearly isn’t. Being flippant or cavalier with the professional lives of your employees represents the surest path to destroying your company. Instead, one of the primary reasons why firing is so (unfortunately) important is because of how difficult, error-prone, and subjective most hiring processes are.
Sep 15, 202219:23
Sell-Side M&A Advisors: How to Choose One, How Much They Cost, and The Importance of the "Fine Print"

Sell-Side M&A Advisors: How to Choose One, How Much They Cost, and The Importance of the "Fine Print"

Today’s episode is for anybody who ever plans to sell a company.

Most entrepreneurs will sell a business once in their entire careers (if they’re lucky), and as a result many understandably don’t have a lot of context or experience in the finer points of exiting, specifically when it comes to how to select an M&A advisor. Most advice that I’ve come across in this domain is frankly too high level to be useful, so today I wanted to get really detailed on how to select an M&A advisor, how much you should expect to pay them, what’s included & excluded from the fees that they charge, and other critical contractual terms you should be aware of before hiring one of them.

To help us answer some of these questions, I’m joined today by John Carvalho. John is the President of Stone Oak Capital, an M&A advisory firm that focuses exclusively on middle market businesses, with a specific focus on transactions between $10 and $100 million.

John is also the Founder of Divestopedia. Since its inception in 2012, Divestopedia has become THE place to go for anybody contemplating selling their company: It contains a dictionary of more than 500 M&A related terms, thousands of articles on the exit process, and is now one of the world's leading online resources for selling a mid-sized business.

In addition to his experience advising CEOs, John is also an entrepreneur himself, having co-founded Wolverine Energy Services Inc. in 2012 with an initial acquisition of a $5 million revenue oilfield services company. From the first acquisition to 2020, John and his business partner acquired 16 more businesses, grew revenue to $240 million and took the company public.

Sep 01, 202201:07:26
Strategic Considerations When Evaluating a Letter of Intent to Sell Your Business

Strategic Considerations When Evaluating a Letter of Intent to Sell Your Business

For many business owners, few things are as exciting as receiving a Letter of Intent (“LOI”) from a prospective purchaser. Beyond the sense of validation stemming from the fact that a sophisticated counterparty sees an asset worth paying for, many business owners likely view an LOI as a just reward for decades of hard work, sacrifice, and illiquidity. 

Understandable as these reactions may be, I would argue that they are premature at best, and misleading (or even incorrect) at worst. 

This audio blog attempts to speak to prospective sellers of small or medium-sized businesses about what LOIs are (and more importantly, what they are not), and to review how experienced buyers may strategically utilize them as tools to further their own objectives, sometimes at the expense of those of the seller.


Aug 04, 202215:32
All Things Finance & Accounting: Managing Cash & Liquidity, Employee Financial Literacy, Capital Allocation, Preparing for Macroeconomic Turbulence, and Hiring Your First CFO

All Things Finance & Accounting: Managing Cash & Liquidity, Employee Financial Literacy, Capital Allocation, Preparing for Macroeconomic Turbulence, and Hiring Your First CFO

Today's episode is all about the finance & accounting function: My guest is Nicholas Andrews, who is the Founder of Aspen Consulting Group, a company that performs finance, accounting, and operations consulting for a wide range of small and medium sized businesses. Aspen’s services include technical accounting, corporate finance, valuations, operations planning and M&A due diligence, among others. Our conversation begins with several questions about how to manage cash and other sources of liquidity amid all of the macroeconomic volatility & uncertainty we’re currently witnessing. We then discuss the topic of employee financial literacy, including the question of how transparent CEOs should be with company financials, and then move to questions of capital allocation and how CEOs should think about spending the cash that they generate, and finally we conclude with several considerations related to hiring, specifically focusing on the question of how CEOs should think about hiring a senior finance & accounting leader, which I suspect many listeners are attempting to do for the first time. Please enjoy!
Jul 21, 202201:16:52
Busting the Biggest Myth About Purchasing and Operating Small Companies

Busting the Biggest Myth About Purchasing and Operating Small Companies

In this episode, I attempt to debunk a common misconception among prospective acquirors, particularly those looking to purchase a business for the first time. This myth states that the smaller the business in question, the easier it is to purchase and operate.

In the material that follows, I will attempt to explain why the exact opposite statement is likely true: That smaller companies are actually much harder to both purchase and operate when compared to their larger peers. 

Jul 07, 202213:31
Running a Business During Inflationary Periods and Understanding Pricing Power (with Jim Sharpe)

Running a Business During Inflationary Periods and Understanding Pricing Power (with Jim Sharpe)

My guest today is a particularly personal and a particularly special one for me: I have been fortunate to call Jim Sharpe a mentor and friend for over 10 years now, and I am thrilled that he agreed to join the podcast.
In this week's episode, we discuss the realities of running a business during high inflation environments, including the risks and opportunities that may present themselves during such times. We also discuss how CEOs should think about pricing their products and services in response to inflationary pressures, and finally how they should deal with vendors who attempt to pass through price increases to them.
Jim has been at at the Harvard Business School since 2009, holding positions as a Senior Lecturer in the MBA and Executive Education programs, an Entrepreneur in Residence, and now serves as a Visiting Executive. In 1987, Jim purchased Extrusion Technology, an aluminum extrusion fabricator that he ran as CEO for over 20 years. In 2008, Jim sold the company to a private equity firm, having grown the company from $4MM to $32MM in revenue throughout his ownership tenure. Jim is now an active investor in small and medium sized businesses, holding ownership positions in more than 50 entrepreneurial companies.
Jun 23, 202201:01:55
The Biggest Temptation of a Software CEO

The Biggest Temptation of a Software CEO

Jun 09, 202215:41
Employee Burnout and The Great Resignation

Employee Burnout and The Great Resignation

My guest today is Carin-Isabel Knoop, Executive Director of the Harvard Business School Case Research & Writing Group. Carin has spent decades writing cases on managers and leaders all over the world, across a wide array of functions and industries. In 2019, alongside co-author John Quelch, she published Compassionate Management of Mental Health in the Modern Workplace, a book that dove deeply into the relationship between work life and mental well-being, and suggested in which managers can and should act as the "chief mental health officers" of their respective teams.  

In today's episode, we dive deeply into the following questions and issues: 

  • Link between employee burnout and turnover
  • Signs for leaders to look for that may be predictive of turnover
  • Prevention strategies, for both the CEO and her employees
  • Can CEOs maintain “high performance cultures” while simultaneously managing the risk of employee burnout?
  • How to detect emotional depletion within yourself
  • Personality traits that are positively correlated with burnout risk 
  • Separating your own sense of happiness from the success of your business at any given time
  • How acquirors of businesses can and should perform due diligence on the employee base that they're acquiring

Please enjoy!

May 26, 202201:08:35
Should You Become an Entrepreneur?

Should You Become an Entrepreneur?

Today's episode is aimed towards those who may be wrestling with the question of whether or not to finally pursue their entrepreneurial dreams. I walk you through how I made this decision myself in 2012, and also attempt to compliment those considerations with some of the lessons and reflections that I’ve garnered in the 10 years since then, which of course benefit from the clarity that only seems to come with hindsight.
Whether or not to take the entrepreneurial plunge is a deeply personal question, and as a result no objectively correct answer exists to address it. What I argue in this episode however is that the answer itself will only be as good as the introspection, thought processes, and clarity of insights that led to it in the first place.
Entrepreneurship is generally much less risky than most might think, though it is also significantly less glamorous than its depiction in most forms of media today. Though most people understandably focus on the risk of walking the entrepreneurial path, it’s equally important to acknowledge of risks of not doing so.
Please enjoy!
May 12, 202220:40