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In The Trenches

Steve Divitkos
Entrepreneurship
Negotiation
Holding Companies
Constellation Software
Leadership
Mergers and Acquisitions
BATNA
Employee Retention
Stock Options
Business Quotes
M&A
Private Equity
Acquisition Entrepreneurship
Acquisition Strategies
Harvard Business School
Axial Market
Software Acquisition
Brokered Transactions
Mergers and Acquisitions (M&A)
Search Funds

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 ex... more

PublishesTwice monthlyEpisodes136Founded5 years ago
Number of ListenersCategories
BusinessEntrepreneurship

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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... more

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

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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... more

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

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Key Facts

Accepts Guests
Accepts Sponsors
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Number of Listeners
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Recent Guests

Jennifer Garvey Berger
Author of Changing on the Job and founder of Cultivating Leadership
Cultivating Leadership
Episode: The Four Stages of Leadership Maturity: Why the CEO Must Change Before the Company Can
Les Trachtman
An experienced entrepreneur, educator, and author
Episode: “Don’t F*ck It Up": Les Trachtman on Avoiding Post-Close Founder Succession Mistakes
Stacey Carroll
HR expert with extensive knowledge in compensation and benefits, founded HR Experts on Call.
HR Experts on Call
Episode: Why Most Incentive Plans Fail—and How Thoughtful CEOs Get Them Right
Alex Hodgkin
Entrepreneur, CEO, and co-founder of the Entrepreneurship Through Acquisition program at the University of Chicago's Booth School of Business
Meritage
Episode: Installing an Operating System in Your Business: Lessons from Real EOS Implementations
Jed Morris
CEO who experienced bankruptcy and rebuilt his life and business
Episode: Facing the Worst-Case Scenario: How Jed Morris Lost His Business and Rebuilt His Life
Geoff Woods
Author of The AI-Driven Leader and expert in AI application for leadership and business growth.
AI Leadership
Episode: How AI is Transforming the Acquisition and Operations of Small Businesses
Chris Smith
Managing partner of Spellbound, which assists companies with technical due diligence and outsourced development services
Spellbound
Episode: Technical Debt: What it is, How Much of it You Can Live With, and How to Incorporate it into an Investment Thesis
Aaron Houghton
Serial entrepreneur, founder of iContact and current CEO of Dory, focused on mental health for high performers
Dory
Episode: Stress, Panic Attacks, Debilitating Anxiety, and a $170M Exit: iContact Founder Aaron Houghton
Rob Markey
Creator of the Net Promoter Score and founder of Bain's Global Customer Strategy Practice
Bain & Company
Episode: Rob Markey: Creator of the Net Promoter Score and Founder of Bain's Global Customer Strategy Practice

Hosts

Steve Divikos
Host of In The Trenches; SMB founder/leader with focus on practical growth and leadership.
Steve Devitt-Kos
Host involved in SMB leadership topics; frequently discusses EOS, acquisitions, and operations.

Reviews

5.0 out of 5 stars from 87 ratings
  • Helpful for operators, investors, or anyone in the business world

    Steve’s podcast is packed with insight and incredibly helpful content. He is engaging, the guests are world class, and it’s a strategic and tactical guide for anyone looking to improve in business.

    Apple Podcasts
    5
    busuuamp
    United States2 years ago
  • Extremely thoughtful and insightful

    I’ve listened to both of Steve’s podcasts on mental health as an entrepreneur and CEO. As an aspiring CEO/Entrepreneur I found the personal experiences he shared very thought provoking. Thanks for being so vulnerable!

    Apple Podcasts
    5
    DougW10001
    United States4 years ago
  • Great show. Love the content

    Great content thats very practical and useful. Keep it up!

    Apple Podcasts
    5
    Money machine1111
    United States4 years ago
  • Actionable, thoughtful, insighful

    Steve does a great job bringing out the crucial moments of SMB entrepreneurship here.

    Apple Podcasts
    5
    Corn1105
    Germany4 years ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Guests reliably highlight crucial moments in SMB growth and leadership.
Value-packed episodes with world-class guests and practical guidance.
Thoughtful takes on mental health for entrepreneurs and CEOs.
Content is highly actionable for SMB operators and investors.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Talking Points

Recent interactions between the hosts and their guests.

“Don’t F*ck It Up": Les Trachtman on Avoiding Post-Close Founder Succession Mistakes
Q: How common is the experience of a founder wanting to remain involved post-sale?
While many founders seek to maintain a connection, it varies from case to case, often depending on their emotional attachment to the company.
“Don’t F*ck It Up": Les Trachtman on Avoiding Post-Close Founder Succession Mistakes
Q: Do you agree that managing the relationship with the seller is among the most important tasks for a new CEO?
Yes, especially since a non-functional or toxic relationship can damage the company significantly.
Installing an Operating System in Your Business: Lessons from Real EOS Implementations
Q: Should a CEO hire a professional implementer to aid in implementing EOS?
It depends; self-funded entrepreneurs may do well self-implementing, but professional implementers can provide valuable expertise and accountability.
Installing an Operating System in Your Business: Lessons from Real EOS Implementations
Q: What are the three primary situations when it's not advisable to implement an operating system?
When the CEO is new and doesn't understand the business yet, during a major crisis, or when there is misalignment with an operational board of directors.
Installing an Operating System in Your Business: Lessons from Real EOS Implementations
Q: What other operating systems might CEOs consider?
Other operating systems include Scaling Up by Vern Harnish and Pinnacle, each offering different tools and complexity levels.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

Listeners per Episode
Gender Skew
Location
Interests
Professions
Age Range
Household Income
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Frequently Asked Questions About In The Trenches

What is In The Trenches about and what kind of topics does it cover?

This show centers on the journeys of entrepreneurs and SMB CEOs, blending practical business tactics with personal resilience. Across episodes, listeners glimpse leadership evolution, M&A nuances, incentive design, operating-system implementations in growing companies, and the mental health realities of high-performing founders. Guests span HR, finance, coaching, acquisition entrepreneurship, and technology leadership, often tying lessons to real-world outcomes like smoother leadership transitions, better organizational alignment, and smarter investment theses. A standout theme is the focus on actionable frameworks (EOS, four stages of leadership maturity, working capital considerations, and risk-controlled investment philosophies) paired w... more

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Which podcasts are similar to In The Trenches?

These podcasts share a similar audience with In The Trenches:

1. Acquiring Minds
2. Acquisitions Anonymous - #1 for business buying, selling and operating
3. The Knowledge Project
4. Invest Like the Best with Patrick O'Shaughnessy
5. Moneywise

How many episodes of In The Trenches are there?

In The Trenches launched 5 years ago and published 136 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on In The Trenches?

Recent guests on In The Trenches include:

1. Jennifer Garvey Berger
2. Les Trachtman
3. Stacey Carroll
4. Alex Hodgkin
5. Jed Morris
6. Geoff Woods
7. Chris Smith
8. Aaron Houghton

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