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In The Trenches

Steve Divitkos
Entrepreneurship
Search Funds
Mergers and Acquisitions
Private Equity
Leadership
Entrepreneurial Operating System
Mental Health
Working Capital Adjustment
Small Business
Company Culture
Financial Due Diligence
Leverage
Leadership Development
Acquisition Entrepreneurship
Software Acquisition
Growth Management
Business Acquisition
Incentive Compensation Plans
Technical Debt
Happiness

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 monthlyEpisodes144Founded5 years ago
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EntrepreneurshipBusiness

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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 ⁠⁠... more

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.

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This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Boulay, ... 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 ⁠⁠⁠⁠⁠⁠... more

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

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Recent Guests

Rishi Sahel
CEO of Orion Cordage (Orion Rope Works and Canada Cordage)
Orion Cordage
Episode: A Peek Behind the Curtain: What Small Business Ownership *Really* Looks Like
Ronnen Harary
Co-founder of Spin Master
Spin Master
Episode: $2B Company Founder on Youth, Inexperience, and Why You're More Ready Than You Think
Larry Weinzimmer
Professor of Strategic Management, Bradley University; bestselling author of The Wisdom of Failure
Bradley University; author
Episode: The Wisdom of Failure: Growing from our Personal and Professional Setbacks
Cameron Herold
Founder of the COO Alliance; former COO of 1-800-GOT-JUNK
COO Alliance / 1-800-GOT-JUNK
Episode: Hiring Your Second in Command: With Cameron Herold, Founder of the COO Alliance and Former COO of 1-800-GOT-JUNK
Michael Bernard
Leading REBT practitioner and entrepreneur
REBT practitioner, entrepreneur
Episode: Identifying the Irrational Beliefs Hindering Your Decision Making
Dr. Jim Schleckser
Author of Great CEOs Are Lazy; founder of the CEO Project
Episode: "Great CEOs Are Lazy": Why the Best SMB Leaders Do Less—But Achieve More
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

Hosts

Steve Divikos
Host of In The Trenches
Steve Devitt-Gosz
Host of In The Trenches

Reviews

5.0 out of 5 stars from 91 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 States5 years ago
  • Great show. Love the content

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

    Apple Podcasts
    5
    Money machine1111
    United States5 years ago
  • Actionable, thoughtful, insighful

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

    Apple Podcasts
    5
    Corn1105
    Germany5 years ago

Listeners Say

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

Thoughtful, actionable content with world-class guests.
Engaging host and practical insights for operators and investors alike.
Content is practical and focused on SMB entrepreneurial realities.

Chart Rankings

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

Talking Points

Recent interactions between the hosts and their guests.

A Peek Behind the Curtain: What Small Business Ownership *Really* Looks Like
Q: How did you handle leadership and decision-making early in your tenure during COVID?
We leaned into a rallying narrative around serving critical infrastructure, empowered the team with a clear mission, and moved quickly to diagnose and act on problems rather than wait for a perfect plan.
A Peek Behind the Curtain: What Small Business Ownership *Really* Looks Like
Q: What did the business look like when you bought it in May 2020?
It was a sizable domestic cordage manufacturer with mid-20s revenue and about 20% EBITDA, but growth had been flat for five years. The opportunity was in applying a stronger growth engine, better systems, and price discipline to unlock value.
$2B Company Founder on Youth, Inexperience, and Why You're More Ready Than You Think
Q: What are the two buckets of support a business partner provides, and which is more meaningful in your experience?
Commercial collaboration and emotional support both matter, but having a mind meld and aligned vision with low ego is most critical for moving fast and making the right strategic calls.
$2B Company Founder on Youth, Inexperience, and Why You're More Ready Than You Think
Q: How do you define and pursue 'tail events' like Paw Patrol, and what role did luck versus planning play?
Tail events require readiness to seize rare opportunities; while planning and learning build capability, some outcomes hinge on serendipity and market timing that you can't fully predict.
$2B Company Founder on Youth, Inexperience, and Why You're More Ready Than You Think
Q: What percentage of your early successes came from things you learned before starting Spin Master versus learned after starting?
Early success was driven by naivety and intuition; learning on the go and surrounding yourself with positive people amplified opportunities, while past knowledge helped in pattern recognition but not as a sole driver.

Audience Metrics

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

Listeners per Episode
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Interests
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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 targets entrepreneurs and SMB CEOs who want practical, battle-tested guidance for scaling and leading in real-world environments. Episodes blend tactical frameworks (like 4DX execution, EOS, and risk-aware underwriting) with candid founder stories, leadership development, and operational improvements across M&A, HR, and technology. Listeners can expect a steady stream of actionable takeaways — from hiring a strong second-in-command to designing simple, effective incentive plans — delivered through in-the-trenches anecdotes and coach-like coaching from experienced guests.

What stands out is the breadth of guests, spanning operators, investors, HR professionals, and technology leaders, all focused on pragmatic, implementable progres... more

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How many listeners does In The Trenches get?

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To see how many followers or subscribers In The Trenches has on Spotify and other platforms such as Castbox and Podcast Addict, simply upgrade your account. You'll also find viewership figures for their YouTube channel if they have one.

Which podcasts are similar to In The Trenches?

These podcasts share a similar audience with In The Trenches:

1. Acquiring Minds
2. Built to Sell Radio
3. Acquisitions Anonymous - #1 for business buying, selling and operating
4. Moneywise
5. The Knowledge Project

How many episodes of In The Trenches are there?

In The Trenches launched 5 years ago and published 144 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

How do I contact In The Trenches?

Our systems regularly scour the web to find email addresses and social media links for this podcast. We scanned the web and collated all of the contact information that we could find in our podcast database. But in the unlikely event that you can't find what you're looking for, our concierge service lets you request our research team to source better contacts for you.

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What guests have appeared on In The Trenches?

Recent guests on In The Trenches include:

1. Rishi Sahel
2. Ronnen Harary
3. Larry Weinzimmer
4. Cameron Herold
5. Michael Bernard
6. Dr. Jim Schleckser
7. Jennifer Garvey Berger
8. Les Trachtman

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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