Steve Divitkos

In The Trenches

Business EN ↓ 144 episodes

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

Business

Latest episode

Jul 9, 2026

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Episodes

A Deep Dive on Hiring 31.08.2023

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 Equ...

"A Guide to the Good Life": What Entrepreneurs Can Learn From Stoic Philosophy 17.08.2023

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%...

Venture Capital “Orphans”: Exploring an Emerging Search Fund Investment Thesis 03.08.2023

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 f...

When Search Funds Don’t Go As Planned (Part 2): With Jim Sharpe 22.07.2023

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...

Lessons Learned From 400+ Post-Exit Entrepreneurs: John Warrillow, Host of Built to Sell Radio 22.07.2023

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 cha...

When Search Funds Don't Go As Planned (Part 1): 3 Searcher Case Studies 22.06.2023

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...

75 Things That I Think Are True 08.06.2023

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 o...

The SMB Credit Markets: Bank Failures, Rising Interest Rates, and a Looming Recession 25.05.2023

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 ass...

The Merits, Risks, and Possible Unintended Consequences of Earn-Outs 11.05.2023

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 offerin...

Mental Health for High Achievers: Ambition, Anxiety, Perfectionism, and Balancing Striving vs. Self-Acceptance 27.04.2023

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...

The 2023 SaaS CEO Survey 13.04.2023

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 e...

Kent Weaver: Building, Working With, and Learning from your Board of Directors 29.03.2023

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 prepara...

How to Know When it's Time to Stop 22.03.2023

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 eventuall...

Are You Selling to the Wrong Customers? 16.03.2023

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 every...

Everything You've Ever Wanted to Know About Working with a Partner: With Dr. Noam Wasserman, Author of The Founder's Dilemmas 02.03.2023

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 pr...

Evaluating the Correlation Between Hours Worked and Success Achieved 16.02.2023

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 pr...

The Smallest Changes That Had The Largest Impacts: 4 CEO Case Studies 02.02.2023

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 pr...

Constructing, Managing, and Working with a Board of Directors 19.01.2023

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 effectivel...

Mike Zani, CEO of The Predictive Index: Hiring, Personality Profiling Tools, Working with a Partner, and Other Lessons from 20 Years as a CEO 05.01.2023

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 effectivel...

The Current State of the Debt Capital Markets 22.12.2022

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, work...

Evaluating 5 Very Different Approaches to Acquiring a Software Company 08.12.2022

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, work...

Brent Beshore: The "Forrest Gump of Private Equity" 24.11.2022

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 a...

Tools in Managing my own Psychology 10.11.2022

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 a...

A.J. Wasserstein: Reflections of a Founder, CEO, Investor and Educator 27.10.2022

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 a...

The CEO as Chief Capital Allocator 13.10.2022

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 a...

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