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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.
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Episodes

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 ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * In a previous post ( 75 Things That I Think Are True ), I compiled quotes from countless books, mentors, pod...

Apr 25, 202411 minSeason 9Ep. 6

The Constellation Software Playbook for Acquiring and Growing Software Companies

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠ * 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 * Constellation Software is one of the world's most widely followed and admired software companies, having acquired u...

Apr 11, 20241 hr 18 minSeason 9Ep. 5

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 * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠ * After many years of using company stock options as attraction, retention, and incentive alignment tools, I’ve come to app...

Mar 28, 202423 minSeason 9Ep. 4

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 * 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 * Today I'm joined by entrepreneur, CEO, and best-selling author, Rob Dube. In 1991, Rob co-founded imageOne, a managed p...

Mar 14, 20241 hr 27 minSeason 9Ep. 3

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 * This episode is brought to you by ⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠ * Many searchers understandably tend to have very similar questions and areas of uncertainty. Indeed, in most instances, I had ...

Feb 29, 202445 minSeason 9Ep. 2

Profit Before Anything Else: With Mike Michalowicz, Author of "Profit First"

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 ⁠⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠ * Today I'm joined by Entrepreneur, Investor, and Author Mike Michalowicz. In addition to being the author of 9 books, ...

Feb 14, 20241 hr 19 minSeason 9Ep. 1

Royce Yudkoff & Rick Ruback: Educators, Mentors, and Leaders Within the SMB Community

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠ * 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 * Today I am thrilled to be joined by two guests that, without the risk of hyperbole, have changed my life in more ways than ...

Feb 01, 20241 hr 2 minSeason 8Ep. 10

Jeff Stevens & A.J. Wasserstein on The Future of Entrepreneurship Through Acquisition

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 ⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠ * Today I'm joined by two of the most thoughtful, distinguished, and respected investors in the ETA ecosystem, Jeff Stevens and A.J....

Jan 18, 20241 hr 33 minSeason 8Ep. 9

Michael Girdley on The Rise of Holding Companies

This episode is brought to you by ⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠ * 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 * Today I'm joined by Michael Girdley , an entrepreneur and investor who has spent the past 30 years building a personal holding company b...

Jan 04, 202457 minSeason 8Ep. 8

Questions You Should Be Prepared to Answer Before Buying (or Selling) a Small Business

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 ⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠ * Over many years of evaluating acquisition targets alongside searchers, I’ve found that certain questions tend to apply more often than not. I’...

Dec 21, 202329 minSeason 8Ep. 7

What I'd Change if I Could Re-Do the First 90 Days of my Search: 3 Searcher Case Studies

This episode is brought to you by ⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠ * 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 * In today's episode, I will be speaking with 3 searchers, each of whom are at different stages of their respective search journeys. As I have done in...

Dec 07, 20231 hr 1 minSeason 8Ep. 6

Dr. Victoria Medvec on the Art and Science of High Stakes Negotiations

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 a full 15% off of any of their services for listeners of In the Trenches. ⁠⁠...

Nov 23, 20231 hr 35 minSeason 8Ep. 5

Peter Lehrman, Founder & CEO of Axial, The Largest Online Marketplace to Buy & Sell SMBs

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 assess the pros and cons of your target company’s insurance pr...

Nov 09, 20231 hr 24 minSeason 8Ep. 4

Conscious Leadership with Executive Coach and Best-Selling Author Kaley Klemp

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 a full 15% off of any of their services for listeners of In the Trenches. ⁠⁠⁠⁠J...

Oct 26, 202358 minSeason 8Ep. 3

Building a $5.5B Mid-Market Private Equity Firm: Brent Belzberg, Founder of Torquest Partners

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 assess the pros and cons of your target company’s insurance progra...

Oct 12, 20231 hr 16 minSeason 8Ep. 2

My Experience With Anxiety

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 a full 15% off of any of their services for listeners of In the Trenches. ⁠⁠⁠Just...

Sep 28, 202324 minSeason 8Ep. 1

A Deep Dive on Compensation

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 assess the pros and cons of your target company’s insurance program, inclu...

Sep 14, 20231 hr 7 minSeason 7Ep. 10

A Deep Dive on Hiring

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 firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on a...

Aug 31, 20232 hr 17 minSeason 7Ep. 9

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

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 assess the pros and cons of your target company’s insurance program, including...

Aug 17, 20231 hr 20 minSeason 7Ep. 8

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

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 firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all th...

Aug 03, 202317 minSeason 7Ep. 7

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

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 a full 15% off of any of their services for listeners of In the Trenches. Just go to ⁠⁠⁠...

Jul 22, 20231 hr 3 minSeason 7Ep. 5

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

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 assess the pros and cons of your target company’s insurance program, including any potenti...

Jul 22, 202354 minSeason 7Ep. 6

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

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 assess the pros and cons of your target company’s insurance program, including any potential ...

Jun 22, 20231 hr 54 minSeason 7Ep. 4

75 Things That I Think Are True

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 a full 15% off of any of their services for listeners of In the Trenches. Just go to ⁠⁠⁠⁠⁠th...

Jun 08, 202322 minSeason 7Ep. 3

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

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 assess the pros and cons of your target company’s insurance program, including any potential coverage g...

May 25, 20231 hr 10 minSeason 7Ep. 2

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

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 a full 15% off of any of their services for listeners of In the Trenches . Just go to ⁠⁠⁠the Conta...

May 11, 202323 minSeason 7Ep. 1

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

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 a full 15% off of any of their services for listeners of In the Trenches . Just go to ⁠⁠the Contact ...

Apr 27, 20231 hr 35 minSeason 6Ep. 10

The 2023 SaaS CEO Survey

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 everything else in between. Reach out to Anthony Rodriguez (arodriguez@avidbank.com) or Conor Tidgwel...

Apr 13, 202335 minSeason 6Ep. 9

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

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 preparation, among countless other things. I was a customer of theirs for 7 consecutive years while running ...

Mar 29, 202355 minSeason 6Ep. 8

How to Know When it's Time to Stop

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 eventually grew to become much less promising. These entrepreneurs are also (rightly) applauded, though this t...

Mar 22, 202318 minSeason 5Ep. 2
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