
In The Trenches
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.
Latest episodes

4 snips
Jul 4, 2024 • 1h 6min
You Don't Have an Engineering Problem, You Have a Product Management Problem
In this podcast, they discuss the importance of product management in software companies and how it can affect engineering, sales, and customer support. The guest, a product management expert, shares insights on hiring product leaders, prioritizing features, and dealing with sales requests. They also talk about the challenges faced by software CEOs in large sales transactions and the significance of soliciting feedback from customers and internal stakeholders.

Jun 20, 2024 • 28min
Evaluating The Most Common Forms of Debt Used to Finance Small Business Acquisitions
Exploring the different forms of debt used in small business acquisitions, including bank debt, mezzanine debt, seller financing, and SBA loans. It evaluates the benefits and risks of each type of debt and how they can be leveraged effectively to finance business purchases.

Jun 6, 2024 • 1h 26min
From $7M to $50M via 14 Acquisitions: A Consolidation Success Story With Jay Davis & Jason Pananos
Jay Davis and Jason Pananos, successful entrepreneurs who transformed their careers through strategic acquisitions, share their remarkable journey from $7 million to $50 million in revenue. They discuss the importance of timing and resilience during their growth phase, detailing how each acquisition shaped their trajectory. Insightful topics include navigating post-acquisition integration, the role of platform companies, and the nuances of building strong business partnerships. Their experiences reveal valuable lessons on maintaining adaptability and fostering relationships in the competitive world of business acquisitions.

May 23, 2024 • 1h 7min
Why You May Be Ignoring Brokered Deals at Your Peril
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’s episode is all about participating in brokered transactions, and working with brokers more broadly (by "brokers", I am referring to investment banks, accounting firms, business brokers, or any other sell-side advisor whose job it is to help clients sell their companies). To inform our discussion today, I’m joined by Ryan Farkas, a Partner, Managing Director and the Practice Leader in M&A and Capital Markets at BDO, who has successfully closed countless sell-side advisory transactions spanning dozens of industries.

May 9, 2024 • 20min
Why You May Want to Reconsider Your Industry Roll-up Strategy
Exploring the trend of industry roll-ups, challenges of fragmentation, post-acquisition integration, financing strategies, M&A growth considerations, and skeptical views on consolidation theses within the search fund ecosystem.

Apr 25, 2024 • 11min
45 (More) Things That I Think Are True
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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In a previous post (75 Things That I Think Are True), I compiled quotes from countless books, mentors, podcasts and blogs to present 75 ideas that I believed to be fundamentally true, spanning both business and personal considerations. Since publishing that post last year, I have come across 45 additional quotes that I thought were also worthy of presentation. I hope that some of these new submissions also distill a lifetime of wisdom into only a few words.

19 snips
Apr 11, 2024 • 1h 18min
The Constellation Software Playbook for Acquiring and Growing Software Companies
Explore Constellation Software's playbook for acquiring and growing software companies, focusing on key metrics, the rule of 40, criteria for business leaders, transitioning older companies to SaaS models, enhancing software applications, managing seller involvement, and effective product management post-acquisition.

Mar 28, 2024 • 23min
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 14, 2024 • 1h 27min
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").

Feb 29, 2024 • 45min
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
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