Steve Divitkos
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.
Author
Steve Divitkos
Category
Podcast website
Latest episode
Jul 9, 2026
Where to listen?
Podcasts in the app Replaio Radio Coming soonPodcasts are coming to the app soon. Install now and be the first to see a whole new take on podcasts
Episodes
A Peek Behind the Curtain: What Small Business Ownership *Really* Looks Like 09.07.2026 1:24:28
This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years * This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Pro...
$2B Company Founder on Youth, Inexperience, and Why You're More Ready Than You Think 25.06.2026 1:11:48
This episode is brought to you by Kilpatrick, a leading global law firm with a dedicated search fund team that works with searchers from inception, to acquisition, to exit . * This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years * This...
When Both Sides Are Right: Navigating the Trade-Offs That Define Leadership 11.06.2026 24:15
This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years * This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider...
The Wisdom of Failure: Growing from our Personal and Professional Setbacks 28.05.2026 1:00:30
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 * This episode is brought to you by Kilpatrick, a leading global law firm with a dedicated search fun...
The Real Reason Why Most Companies Miss Their Annual Goals 14.05.2026 25:41
This episode is brought to you by Kilpatrick, a leading global law firm with a dedicated search fund team that works with searchers from inception, to acquisition, to exit . * This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years * This episode is broug...
Ten Ways to Underwrite a Conservative and Realistic Base Case 30.04.2026 21:37
This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years * This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search F...
Hiring Your Second in Command: With Cameron Herold, Founder of the COO Alliance and Former COO of 1-800-GOT-JUNK 16.04.2026 55:32
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 * This episode is brought to you by Boulay, the industry standard for Quality of Earnin...
Identifying the Irrational Beliefs Hindering Your Decision Making 02.04.2026 1:20:09
This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years * This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Fund...
"Great CEOs Are Lazy": Why the Best SMB Leaders Do Less—But Achieve More 19.03.2026 1:55:20
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 * This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and...
Are Search Funds Moving Up Market? 05.03.2026 12:48
This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years * This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds a...
The Four Stages of Leadership Maturity: Why the CEO Must Change Before the Company Can 19.02.2026 56:52
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 * This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and au...
“Don’t F*ck It Up": Les Trachtman on Avoiding Post-Close Founder Succession Mistakes 05.02.2026 1:18:07
This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years * This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other...
Why Most Incentive Plans Fail—and How Thoughtful CEOs Get Them Right 20.01.2026 1:02:54
I suspect that the CEOs in our audience are likely to agree that crafting a truly effective incentive compensation plan is simultaneously one of the most difficult, and one of the most important, tasks that a small business CEO will face. Charlie Munger is famous for saying “ Never, ever think about something else when you should be thinking about the power of incentives .” He's also said “ I thin...
Installing an Operating System in Your Business: Lessons from Real EOS Implementations 08.01.2026 55:33
This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years * This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Smal...
The Working Capital Adjustment 23.12.2025 14:22
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 * This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit...
Hard to Kill: A Four-Part Framework for Evaluating Small Business Acquisitions 11.12.2025 21:16
This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years * This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Smal...
Facing the Worst-Case Scenario: How Jed Morris Lost His Business and Rebuilt His Life 27.11.2025 1:28:43
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 * This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit...
How AI is Transforming the Acquisition and Operations of Small Businesses 13.11.2025 1:01:23
This episode is brough to you by System Six, an outsourced finance, accounting, and tax partner to over 300 businesses nationwide * This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years * This episode is brought to you by ...
Technical Debt: What it is, How Much of it You Can Live With, and How to Incorporate it into an Investment Thesis 30.10.2025 1:26:21
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 * This episode is brought to you by B oulay, the industry standard for Quality of Earnings, tax, and audit se...
Announcing the Launch of Mineola Fund II 22.10.2025 1:11
In 2022, we launched Mineola’s first fund to help entrepreneurs navigate the tactical, commercial, and personal challenges that are an inevitable part of the acquisition entrepreneurship journey. Almost four years later, we’re excited to continue this work through Mineola Fund II. Playing a small role in helping people realize their entrepreneurial dreams has proven to be an incredibly fulfilling...
Stress, Panic Attacks, Debilitating Anxiety, and a $170M Exit: iContact Founder Aaron Houghton 16.10.2025 1:17:43
This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years * This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-M...
Rob Markey: Creator of the Net Promoter Score and Founder of Bain's Global Customer Strategy Practice 02.10.2025 1:19:35
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 * This episode is brought to you by B oulay, the industry standard for Quality of Earnings, tax, and audit servi...
Building Better CEOs: Lessons From a Veteran Executive Coach 18.09.2025 1:10:52
This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years * This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medi...
The Acquisition Entrepreneur and Mental Health 28.08.2025 32:12
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 * This episode is brought to you by B oulay, the industry standard for Quality of Earnings, tax, and audit services...
Evaluating Customer Retention in Recurring Revenue Businesses: With Craig Zingerline 14.08.2025 1:16:10
This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years * 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-...
Similar podcasts
Replaio is not a podcast publisher; show names, artwork and audio belong to their authors and are distributed through public RSS feeds.