Shows
M&A LaunchpadUps & Downs of the CEO Life with Steve DivitkosIn this episode of the M&A Launchpad Podcast, hosts Feras Moussa and Casey Minshew welcome special guest Steve Divitkos, discussing the challenges of launching and growing a search fund. Steve shares his experiences as a first-time CEO, the emotional toll, strategic decisions, and the eventual exit from his company. Steve dives deep into what it’s like to be a CEO. For example, the challenges he faced around the perception of young CEOs, as well as the decision process between firing and hiring top talent. At the end of the day, Steve states that the path to growth is no...
2024-11-1437 min
In The TrenchesDr. Bill Hudenko: Professor of Psychology at the Dartmouth School of Medicine and a 4x Founder & CEOThis episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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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
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Today I'm joined by Dr. Bill Hudenko, an Assistant Professor of Clinical Psychology at the Dartmouth School of Medicine. In addition to his experience as a professor and clinician, Dr. Hudenko is also a 4x CEO & Entrepreneur, having founded and sold several companies that have utilized technology to improve mental health outcomes for customers. Because of his incredibly unique career that spans coding, entrepreneurship, psychology, medicine, leadership, and technology,
2024-08-151h 12In The TrenchesFrom Combat to Classrooms: How Jim Vesterman Went from Special Forces to a 13.5x Return in 8 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-Sized Businesses
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This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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My guest today is Jim Vesterman, currently a lecturer at the Wharton School at the University of Pennsylvania. Prior to joining the faculty at Wharton, Jim was the CEO of Raptor Technologies, a company that he purchased through his own search fund in 2012, and ran through to a successful exit in 2020. Under Jim’s tenure, Raptor technologies grew from serving 7,000 schools in the United States to serving over 40,000 schools with an in...
2024-08-011h 26In The Trenches17 Lessons on the Psychology of Being a Searcher and CEOThis episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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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
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During my ~10 years as a searcher and CEO, I had an endless number of commercial problems and opportunities that required my attention at any given time. However, it was often the personal considerations that kept me up at night: I rarely lost sleep over whether to raise prices by 5% or 15%, but instead was kept awake by the idea that even asking the question suggested that I didn’t truly know what I was doing. I wasn’t...
2024-07-1831 minIn The TrenchesYou Don't Have an Engineering Problem, You Have a Product Management ProblemThis 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
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This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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Based on my own experience as a software CEO, I think that Product Management is one of the most important - and one of the lest well understood - ingredients to building a successful software company. Many software businesses (particularly mature ones still led by their original Founders) don't have any product management function at all. While this may be tenable under the Founder's leadership, it is almost never tenable when the company...
2024-07-041h 06In The TrenchesEvaluating The Most Common Forms of Debt Used to Finance Small Business AcquisitionsThis episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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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
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Though it is correct to suggest that all acquisitions are funded through some combination of cash-on-hand, debt, or equity, it’s also a bit of an oversimplification. Indeed, the financing options available to prospective acquirors are numerous, and in today’s blog post, I focus specifically on debt, and evaluate the four most common sources of leverage used to finance the purchase of small and medium-sized businesses. These include ban
2024-06-2027 minIn The TrenchesFrom $7M to $50M via 14 Acquisitions: A Consolidation Success Story With Jay Davis & Jason PananosThis 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
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This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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I recently published a blog post, Why You May Want to Reconsider Your Industry Roll-up Strategy, within which I detailed many of the ways in which consolidation strategies can go wrong. In today’s episode, I want to look at the opposite side of that coin and dig deeply into an instance where a consolidation strategy went very right.
I'm joined today by Jay Davis & Jason Pananos, who, after...
2024-06-061h 26In The TrenchesWhy You May Be Ignoring Brokered Deals at Your PerilThis episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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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
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Today’s episode is all about participating in brokered transactions, and working with brokers more broadly (by "brokers", I am referring to investment banks, accounting firms, business brokers, or any other sell-side advisor whose job it is to help clients sell their companies). To inform our discussion today, I’m joined by Ryan Farkas, a Partner, Managing Director and the Practice Leader in M&A and Capital Markets at BDO, who has successfully closed countle
2024-05-231h 06In The TrenchesWhy You May Want to Reconsider Your Industry Roll-up StrategyThis 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
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This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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Though pursuing the consolidation of an industry is not necessarily a new thesis within the search fund ecosystem, I have observed that it has become increasingly popular over the past few years among prospective searchers. Though there have been, and will continue to be, many consolidation success stories within the search fund ecosystem, I suspect there will be an equal number of failures, though this latter outcome will surely be much less publicized. Though...
2024-05-0919 minIn The Trenches45 (More) Things That I Think Are TrueThis 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
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This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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In a previous post (75 Things That I Think Are True), I compiled quotes from countless books, mentors, podcasts and blogs to present 75 ideas that I believed to be fundamentally true, spanning both business and personal considerations. Since publishing that post last year, I have come across 45 additional quotes that I thought were also worthy of presentation. I hope that some of these new submissions also distill a lifetime of wisdom into o
2024-04-2511 minIn The TrenchesThe Constellation Software Playbook for Acquiring and Growing Software CompaniesThis episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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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
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Constellation Software is one of the world's most widely followed and admired software companies, having acquired upwards of 500 lower-middle-market software companies since its founding in 1995. Our guest today, Mike Dufton, is the CEO of the Volaris group, one of the six major operating units within Constell
2024-04-111h 17In The TrenchesEvaluating Stock Options as Attraction, Retention, and Incentive Alignment ToolsThis 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
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This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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After many years of using company stock options as attraction, retention, and incentive alignment tools, I’ve come to appreciate their merits, risks, and possible alternatives. I intend to share these lessons with you today. More specifically though, I will argue that w...
2024-03-2822 minIn The TrenchesCan Ambition and Inner Peace Coexist? With Rob DubeThis episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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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
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Today I'm joined by entrepreneur, CEO, and best-selling author, Rob Dube. In 1991, Rob co-founded imageOne,
a managed print services business based in Oak Park, Michigan, that has won countless awards across countless publications for it’s growth, culture, and employee engagement...
2024-03-141h 26In The TrenchesAnswers to Recurring FAQs from Current and Prospective SearchersThis 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
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This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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Many searchers understandably tend to have very similar questions and areas of uncertainty. Indeed, in most instances, I had these very same questions and areas of uncertainty myself prior to raising my own search fund in 2012. As a result of the frequency with which I'm asked...
2024-02-2944 minIn The TrenchesProfit 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
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This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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Today I'm joined by Entrepreneur, Investor, and Author Mike Michalowicz. In addition to being the author of 9 books, Mike is himself a serial entrepreneur, having founded, operated, and successfully exited several companies across his multi-decade career. He now spends much of his professional time writing, speaking, and coaching CEOs and entrepreneurs on the various systems that helped ma...
2024-02-141h 19In The TrenchesRoyce Yudkoff & Rick Ruback: Educators, Mentors, and Leaders Within the SMB CommunityThis episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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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
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Today I am thrilled to be joined by two guests that, without the risk of hyperbole, have changed my life in more ways than I can count. Royce Yudkoff & Rick Ruback are both professors at the Harvard business school, and co-teach two wildly popular courses called “The Financial Management of Smaller Firms” and “Entrepreneurship through Acquisition”, both of wh...
2024-02-011h 02In The TrenchesJeff Stevens & A.J. Wasserstein on The Future of Entrepreneurship Through AcquisitionThis 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
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This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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Today I'm joined by two of the most thoughtful, distinguished, and respected investors in the ETA ecosystem, Jeff Stevens and A.J. Wasserstein, to discuss the future of acquisition entrepreneurship. The paper that inspired this episode, written by both Jeff & A.J...
2024-01-181h 32In The TrenchesMichael Girdley on The Rise of Holding CompaniesThis episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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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
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Today I'm joined by Michael Girdley, an entrepreneur and investor who has spent the past 30 years building a personal holding company boasting over $100M in annual revenue, comprised of 12 businesses across software, technology, consumer re...
2024-01-0457 minIn The TrenchesQuestions You Should Be Prepared to Answer Before Buying (or Selling) a Small BusinessThis 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
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This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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Over many years of evaluating acquisition targets alongside searchers, I’ve found that certain questions tend to apply more often than not. I’ve presented each of these FAQs in today's episode, in hopes that they play a small r...
2023-12-2129 minIn The TrenchesWhat I'd Change if I Could Re-Do the First 90 Days of my Search: 3 Searcher Case StudiesThis episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses
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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
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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 the past, I will again be asking these guests only a single question: Knowing what...
2023-12-071h 00In The TrenchesDr. Victoria Medvec on the Art and Science of High Stakes NegotiationsThis 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 form on their website and tell them that you’re a listener of the podcast to receive this discount!
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This episode is brought to you by Oberle Risk Strategies, the leading insurance broker...
2023-11-231h 35In The TrenchesPeter Lehrman, Founder & CEO of Axial, The Largest Online Marketplace to Buy & Sell SMBsThis 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 gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 customers across a decade of...
2023-11-091h 24In The TrenchesConscious Leadership with Executive Coach and Best-Selling Author Kaley KlempThis 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 form on their website and tell them that you’re a listener of the podcast to receive this discount!
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This episode is brought to you by Oberle Risk Strategies...
2023-10-2657 minIn The TrenchesBuilding a $5.5B Mid-Market Private Equity Firm: Brent Belzberg, Founder of Torquest PartnersThis 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 gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 customers across a d...
2023-10-121h 16In The TrenchesMy Experience With AnxietyThis 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 form on their website and tell them that you’re a listener of the podcast to receive this discount!
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This episode is brought to you by Oberle Risk Strategies, the leading insu...
2023-09-2824 minIn The TrenchesA Deep Dive on CompensationThis 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 gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 cust...
2023-09-141h 07In The TrenchesA Deep Dive on HiringThis 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 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 Trenc...
2023-08-312h 17In The Trenches"A Guide to the Good Life": What Entrepreneurs Can Learn From Stoic PhilosophyThis 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 gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over...
2023-08-171h 19In The TrenchesVenture Capital “Orphans”: Exploring an Emerging Search Fund Investment ThesisThis 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 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 t...
2023-08-0317 minIn The TrenchesWhen Search Funds Don’t Go As Planned (Part 2): With Jim SharpeThis 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 form on their website and tell them that you’re a listener of the podcast to receive this discount!
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This episode is brought to you by Oberle Risk Strategies, the leading insurance brokera...
2023-07-221h 02In The TrenchesLessons Learned From 400+ Post-Exit Entrepreneurs: John Warrillow, Host of Built to Sell RadioThis 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 gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has se...
2023-07-2253 minIn The TrenchesWhen Search Funds Don't Go As Planned (Part 1): 3 Searcher Case StudiesThis 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 gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle...
2023-06-221h 54In The Trenches75 Things That I Think Are TrueThis 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 form on their website and tell them that you’re a listener of the podcast to receive this discount!
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This episode is brought to you by Oberle Risk Strategies, the lead...
2023-06-0822 minIn The TrenchesThe SMB Credit Markets: Bank Failures, Rising Interest Rates, and a Looming RecessionThis 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 gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those fin...
2023-05-251h 09In The TrenchesThe Merits, Risks, and Possible Unintended Consequences of Earn-OutsThis 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 form on their website and tell them that you’re a listener of the podcast to receive this discount!
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Thi...
2023-05-1123 minIn The TrenchesMental Health for High Achievers: Ambition, Anxiety, Perfectionism, and Balancing Striving vs. Self-AcceptanceThis 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 form on their website and tell them that you’re a listener of the podcast to receive this discount!
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2023-04-271h 34In The TrenchesThe 2023 SaaS CEO SurveyThis 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 Tidgwell (ctidgwell@avidbank.com) to learn more.
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This episode is brought to you by Symphony. Symphony not only performs technical due dili...
2023-04-1334 minIn The TrenchesKent Weaver: Building, Working With, and Learning from your Board of DirectorsThis 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 my own company, and am speaking as a happy customer. Book a call with Founder and CEO, Fern Gordon (Ferngordon@theprofitline.com) or visit th...
2023-03-2955 minIn The TrenchesHow to Know When it's Time to StopIt'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 time it’s for the foresight, objectivity and courage that they demonstrated in making what must have been an incredibly difficult decision to “quit”.
So, which is it? Should entrepre...
2023-03-2217 minIn The TrenchesAre You Selling to the Wrong Customers?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 Tidgwell (ctidgwell@avidbank.com) to learn more.
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This episode is brought to you by The Profit Line. The Profit Line i...
2023-03-1628 minIn The TrenchesEverything You've Ever Wanted to Know About Working with a Partner: With Dr. Noam Wasserman, Author of The Founder's DilemmasThis 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 my own company, and am speaking as a happy customer. Book a call with Founder and CEO, Fern Gordon (Ferngordon@theprofitline.com) or visit th...
2023-03-021h 37In The TrenchesEvaluating the Correlation Between Hours Worked and Success AchievedThis 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 my own company, and am speaking as a happy customer. Book a call with Founder and CEO, Fern Gordon (Ferngordon@theprofitline.com) or visit th...
2023-02-1614 minIn The TrenchesThe Smallest Changes That Had The Largest Impacts: 4 CEO Case StudiesThis 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 my own company, and am speaking as a happy customer. Book a call with Founder and CEO, Fern Gordon (Ferngordon@theprofitline.com) or visit th...
2023-02-021h 30In The TrenchesConstructing, Managing, and Working with a Board of DirectorsThis 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 effectively risk-free: If at the end of the first three months you're not happy with the direction of your business, he will give you your money back. On top of...
2023-01-1921 minIn The TrenchesMike Zani, CEO of The Predictive Index: Hiring, Personality Profiling Tools, Working with a Partner, and Other Lessons from 20 Years as a CEOThis 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 effectively risk-free: If at the end of the first three months you're not happy with the direction of your business, he will give you your money back. On top of...
2023-01-051h 30In The TrenchesThe Current State of the Debt Capital MarketsThis 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, working with Warren is effectively risk-free: If at the end of the first three months you're not happy with the direction of your business, he will give you your...
2022-12-2259 minIn The TrenchesEvaluating 5 Very Different Approaches to Acquiring a Software CompanyThis 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, working with Warren is effectively risk-free: If at the end of the first three months you're not happy with the direction of your business, he will give you your...
2022-12-0830 minIn The TrenchesBrent Beshore: The "Forrest Gump of Private Equity"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 any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else.
Cayn...
2022-11-241h 27In The TrenchesTools in Managing my own PsychologyThis 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 any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else.
Cayn...
2022-11-1022 minIn The TrenchesA.J. Wasserstein: Reflections of a Founder, CEO, Investor and EducatorThis 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 any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else.
Cayn...
2022-10-271h 13In The TrenchesThe CEO as Chief Capital AllocatorThis 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 any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else.
Cayne...
2022-10-1320 minIn The TrenchesBuy at 5X EBITDA, Sell at 8X Revenue: The On-Premise to SaaS Transition of FieldEdgeMy guests today are Steve Lau and Rameez Ansari, co-CEOs of AutoLeap, a software company that services auto repair shops, that counts Bain Capital Ventures among its investors.
Prior to founding AutoLeap, Steve and Rameez purchased, operated, and sold D'Esco (later renamed FieldEdge), a software company that helps entrepreneurs run their HVAC, Plumbing, and Electrical Contracting businesses. Steve and Rameez purchased the company from its original founder in 2015 at 5X EBITDA, when its product was entirely on-premise and its revenue was generated solely through the sale of perpetual use licenses. After successfully transitioning the...
2022-09-291h 18In The TrenchesKnowing Who, When, and How to FireUnfortunate at this reality may be, I would argue that firing (specifically knowing who, when, and how to fire) is a required core competency for any CEO, and is arguably as important as hiring, communication, capital allocation, and other tools within the CEO’s toolkit. The extent to which this is an unpleasant (and perhaps even unpopular) topic to discuss doesn’t negate its critical importance in building and sustaining a healthy and vibrant company.
Some may associate the idea of firing with toxic, authoritarian, or fear-based work cultures. While firing can lead to these types of outcomes if done in a...
2022-09-1519 minIn The TrenchesSell-Side M&A Advisors: How to Choose One, How Much They Cost, and The Importance of the "Fine Print"Today’s episode is for anybody who ever plans to sell a company.
Most entrepreneurs will sell a business once in their entire careers (if they’re lucky), and as a result many understandably don’t have a lot of context or experience in the finer points of exiting, specifically when it comes to how to select an M&A advisor. Most advice that I’ve come across in this domain is frankly too high level to be useful, so today I wanted to get really detailed on how to select an M&A advisor, how much you shou...
2022-09-011h 07In The TrenchesStrategic Considerations When Evaluating a Letter of Intent to Sell Your BusinessFor many business owners, few things are as exciting as receiving a Letter of Intent (“LOI”) from a prospective purchaser. Beyond the sense of validation stemming from the fact that a sophisticated counterparty sees an asset worth paying for, many business owners likely view an LOI as a just reward for decades of hard work, sacrifice, and illiquidity.
Understandable as these reactions may be, I would argue that they are premature at best, and misleading (or even incorrect) at worst.
This audio blog attempts to speak to prospective sellers of small or medium-sized businesses about what L...
2022-08-0415 min
How2Exit: Buy, Don't Build - M&A of Small BusinessesHow2Exit Episode 54: Steve Divitkos - Founder of Mineola Search Partners and a Search Fund Investor.Mineola Search Partners is a firm that invests in Search Funds, the entrepreneurs who run them, and the companies that they acquire.Prior to Mineola, Steve was the CEO of Microdea, a document management and workflow automation software company serving the transportation and logistics industry. Steve acquired the business from its original founders in 2014, and successfully sold the company to a strategic acquirer in 2020 after having served as its CEO for approximately seven years. During Steve’s tenure as CEO, Microdea’s equity value quadrupled, providing his investors with a 20% compounded annual return on their original investment. In his...
2022-08-0358 min
Top M&A EntrepreneursSearcher to CEO and Exit to Search Fund Investor, Steve Divitkos Top M&A Entrepreneurs Take the Business Buyer Readiness Assessment → Jon talks to Steve Divitkos. Steve was in PE, became searchers, acquired a company, grew it, sold it, and is now the Founder of Mineola Search Partners, a company that invests in Search Funds, the entrepreneurs who run them, and the companies that they acquire.Show NotesIntro: 00:0000:45 Where did you start and why become a searcher?02:32 What is search fund - what is your cut of acquisition04:48 Why would a search fund investor install you as CEO with Z...
2022-07-2537 minIn The TrenchesAll Things Finance & Accounting: Managing Cash & Liquidity, Employee Financial Literacy, Capital Allocation, Preparing for Macroeconomic Turbulence, and Hiring Your First CFOToday's episode is all about the finance & accounting function: My guest is Nicholas Andrews, who is the Founder of Aspen Consulting Group, a company that performs finance, accounting, and operations consulting for a wide range of small and medium sized businesses. Aspen’s services include technical accounting, corporate finance, valuations, operations planning and M&A due diligence, among others.
Our conversation begins with several questions about how to manage cash and other sources of liquidity amid all of the macroeconomic volatility & uncertainty we’re currently witnessing. We then discuss the topic of employee financial literacy, including the question of how tran...
2022-07-211h 16
In The TrenchesBusting the Biggest Myth About Purchasing and Operating Small CompaniesIn this episode, I attempt to debunk a common misconception among prospective acquirors, particularly those looking to purchase a business for the first time. This myth states that the smaller the business in question, the easier it is to purchase and operate.
In the material that follows, I will attempt to explain why the exact opposite statement is likely true: That smaller companies are actually much harder to both purchase and operate when compared to their larger peers.
2022-07-0713 minIn The TrenchesRunning a Business During Inflationary Periods and Understanding Pricing Power (with Jim Sharpe)My guest today is a particularly personal and a particularly special one for me: I have been fortunate to call Jim Sharpe a mentor and friend for over 10 years now, and I am thrilled that he agreed to join the podcast.
In this week's episode, we discuss the realities of running a business during high inflation environments, including the risks and opportunities that may present themselves during such times. We also discuss how CEOs should think about pricing their products and services in response to inflationary pressures, and finally how they should deal with vendors who attempt to pass through...
2022-06-231h 01In The TrenchesThe Biggest Temptation of a Software CEOIn his book, The Five Temptations of a CEO, author Patrick Lencioni discusses five areas in which CEOs tend to inadvertently prioritize the wrong things. These “temptations”, as he calls them, can lead to poor decision making at best, and can risk the very survival of the company at worst. My experience leading a software company taught me that there is a sixth temptation, unique to software, that seemed to present itself on a near-daily basis. More specifically:
The biggest temptation of a software CEO is to throw bodies (specifically engineers) at problems.
It is this...
2022-06-0915 minIn The TrenchesEmployee Burnout and The Great ResignationMy guest today is Carin-Isabel Knoop, Executive Director of the Harvard Business School Case Research & Writing Group. Carin has spent decades writing cases on managers and leaders all over the world, across a wide array of functions and industries. In 2019, alongside co-author John Quelch, she published Compassionate Management of Mental Health in the Modern Workplace, a book that dove deeply into the relationship between work life and mental well-being, and suggested in which managers can and should act as the "chief mental health officers" of their respective teams.
In today's episode, we dive deeply into the following qu...
2022-05-261h 08In The TrenchesShould You Become an Entrepreneur?Today's episode is aimed towards those who may be wrestling with the question of whether or not to finally pursue their entrepreneurial dreams. I walk you through how I made this decision myself in 2012, and also attempt to compliment those considerations with some of the lessons and reflections that I’ve garnered in the 10 years since then, which of course benefit from the clarity that only seems to come with hindsight.
Whether or not to take the entrepreneurial plunge is a deeply personal question, and as a result no objectively correct answer exists to address it. What I argue in thi...
2022-05-1220 minIn The TrenchesHaving Hard Conversations (Live Panel Discussion from 2022 MIT Sloan Search Fund Summit)In this week's episode, we discuss the importance of having difficult conversations, something that CEOs find themselves doing on a near-daily basis. We discuss three primary types of difficult conversations, including a) Hard conversations around internal company dynamics (eg: terminations); b) Hard conversations about dynamics external to the company (eg: politics); & c) Difficult conversations that CEOs must sometimes have with themselves (eg: how and when to ask for help).
This is a particularly special episode of In The Trenches for a number of reasons, including:
It is our first ever video podcast! (Video available only through...
2022-04-281h 00In The TrenchesA Leader’s Most Important SkillMy experience as a CEO taught me that the most important skill for any leader to possess is that of clear and effective communication. Indeed, a CEO’s strategy is only as good as her ability to communicate it.
Though some of the basic tenets of effective communication are obvious and intuitive, others are less so. My experience leading a company over many years illustrated that good organizational communication often went well beyond the basics.
In this episode, I will share with you some of the most important lessons that I learned about effective communication within my own company, including if...
2022-04-1416 minIn The TrenchesQuality of Earnings Analysis: What You Need to Know Before Buying a BusinessMy guest today is Chris Hutchinson, a Partner in Ernst & Young's Transaction Advisory Services Group.
Chris has over 15 years of experience advising clients on M&A, financings, valuation projects, and due diligence mandates, with a specific focus on private lower-middle-market businesses. Chris and his team have completed an untold number of Quality of Earnings ("QofE") mandates spanning countless industries, including software, technology, business services, distribution, and retail, among others.
Chris and I discuss what a QofE is, why it's necessary, and common trends and themes that buyers should look out for. We also discuss the working capital adjustment: What it...
2022-03-311h 01In The TrenchesLessons Learned in Capitalizing an AcquisitionAmong the myriad variables that must be carefully considered when acquiring a business is the question of how the acquisition is going to be financed. In today's episode, I will provide you with an overview of the specific lessons that I learned when financing my own acquisition in 2014.
I begin by discussing the critical importance of the link between capital structure and strategy, and then discuss more specific lessons learned in raising the debt required to finance the acquisition.
Please enjoy!
2022-03-1721 minIn The TrenchesAaron Ross: Author of "Predictable Revenue" and "From Impossible to Inevitable"Though Aaron Ross wears many hats, he is perhaps best known for co-authoring the global best seller Predictable Revenue, often referred to as “The Sales Bible of Silicon Valley,” which details an outbound prospecting system that’s created more than $1 billion across Salesforce.com and other companies. Most recently, Aaron published From Impossible to Inevitable, a book co-written alongside Jason Lemkin (serial tech entrepreneur, venture capitalist, and founder of SaaStr.com, the world’s #1 resource for SaaS entrepreneurs), which is a "hypergrowth playbook" based on the successes of companies like Twilio, HubSpot, Marketo, and Salesforce.com.
In addition...
2022-03-0351 minIn The TrenchesThe Entrepreneur and the Spousal RelationshipThe role of spouse to an entrepreneur or CEO is not an easy one, as they are directly impacted by the emotional high and lows that are typical of the journey: They act as a source of consolation during the bad times, keep us grounded during the good times, and in many cases play a large (though often unnoticed and under-appreciated) role in our ultimate successes and failures.
In spite of the importance of the role that spouses play however, the role of a spouse or partner in the entrepreneurial journey is a very under-discussed topic, at least within the...
2022-02-1721 min
Acquisitions Anonymous - #1 for business buying, selling and operatingAnalyzing Software Businesses for Sale with Steve Divitkos, experienced industry CEO - e66We're joined this week by Steve Divitkos, Search Fund Investor & former CEO of Microdea.Steve has a background in private equity investing and after attending Business School he funded a Search Fund in 2012. He is originally from Canada.We examine two Saas businesses currently for sale.Thanks to our sponsors!Trout CPA is a full-service accounting firm offering M&A specific services of valuations, quality of earnings studies, and due diligence review services.The BEYOND8figures podcast (Beyond8Figures.com...
2022-02-0847 minIn The TrenchesBob Pritchett: Author of "Fire Someone Today" and Founder & Executive Chairman of Faithlife SoftwareMy guest today is Bob Pritchett, and I’m really excited to be sharing this episode with you. Bob first came on my radar when I read his book titled “Fire Someone Today”, which was published in 2006. Right before I purchased my first software company, one of my investors and mentors purchased the book for me as a gift, and promised me that, in spite of the fact that I had likely never heard of the book, it was full of countless gems for entrepreneurs and CEOs running SMBs. And he was right: Fire Someone today remains one of my favori...
2022-02-031h 14In The TrenchesThe Working Capital AdjustmentThe Working Capital Adjustment is part of substantially every M&A transaction, yet it is the calculation (and concept) with which most business owners remain largely unfamiliar. Without a proper understanding of what the working capital adjustment is, why it's necessary, and ways in which it can be manipulated, business owners risk leaving a lot of money on the table when dealing with a more sophisticated and experienced counterpart (even AFTER the sale of their business is already complete).
If you don't like the idea of having to wire money back to your buyer after they've wired y...
2022-01-2012 min
A Dealmaker's DNA with Ilan JacobsonEpisode 45: Steve DivitkosAre you running on autopilot? Do you know how to turn off the autopilot? Today’s guest says that people spend more time on autopilot than they’d like to think, and it can prevent them from getting on the right path. Listen in to this interview with Steve Divitkos, an entrepreneur and the former CEO of Microdea. In this episode, you’ll hear about how Steve views entrepreneurship, why introspection is so difficult, and what Steve did right and wrong as a new CEO.
Topics Discussed in This Episode
How Steve was expo...
2022-01-1135 minIn The TrenchesAll Things Hiring with Randy Street: Co-Author of " Who: The A-Method for Hiring" and Vice Chairman of ghSMARTToday’s episode is all about Hiring, and we’ve managed to secure one of the world’s foremost experts on the subject.
My guest is Randy Street. Randy is Vice Chairman of ghSMART, which is a global consulting firm that helps CEOs, boards, and investors build valuable companies specifically through hiring and developing world class leadership teams. During Randy's tenure, ghSMART has grown tenfold, and has been ranked by Forbes as one of America’s Best Consulting Firms from 2017-2020.
Randy first came on my radar when I read the book that he wrote in colla...
2022-01-061h 10In The TrenchesConsiderations Unique to Acquiring a Software Company (Product)In today's episode, I discuss the signs that prospective acquirors should look out for when attempting to uncover how much “technical debt” any given target company may possess within their code base. Though substantially every software company has some amount of technical debt, those that are weighed down by an asymmetric burden of it tend to ship code less frequently, struggle to keep pace with competitors, regularly miss release targets, and are generally much more expensive and capital intensive to operate and grow.
In this way, what start out as technical problems quickly accumulate to become significant business problems.
Thus, pros...
2021-12-2327 minIn The TrenchesVerne Harnish: Founder of The Entrepreneurs' Organization (EO), Author of "Scaling Up" and "Mastering the Rockefeller Habits"Verne Harnish quite literally wrote the book (or, in his case, books), on being an entrepreneur and CEO running a small to medium sized business.
Verne is the founder of the world-renowned Entrepreneurs’ Organization ("EO"), a global network of entrepreneurs and CEOs that boasts over 16,000 members worldwide. For the past 15 years, Verne has chaired EO’s premiere CEO program, the “Birthing of Giants” held at MIT, a program in which he still teaches today.
Verne is also the Founder and CEO of Scaling Up, a global executive education and coaching company with over 200 partners on six continents.
Verne may be best kno...
2021-12-091h 00In The TrenchesImplementing a Formal Operating System Like EOS or the Rockefeller HabitsThroughout recent history, there has been substantial growth in the number of companies who have decided to implement formal “operating systems” to govern certain strategic and operational decisions within their businesses. Though there are many operating systems in existence today, two of the most widely used systems are EOS (based on the book Traction, by Gino Wickman) and The Rockefeller Habits (based on the books Mastering the Rockefeller Habits and Scaling Up, both by Verne Harnish).
I implemented an operating system (EOS) in my own company beginning in 2015, and we continued to operate under its various principles and structures until succ...
2021-11-2515 minIn The TrenchesThe Realities of Managing Extremely Rapid GrowthToday’s show is all about GROWTH. Specifically, I want to dig into the personal and professional realities of running a high growth company that often aren't terribly visible from the outside looking in. Today, I talk to Anthemos Georgiades (or Anth, for short), who is the founder and CEO of Zumper, an apartment rental platform based out of San Francisco.
If anybody knows about running a rapidly growing company, it’s Anth. Consider this: Despite being founded less than 10 years ago in 2012, Zumper now boasts over 250 employees and 75 million active users, making it the biggest residential rental platform in North...
2021-11-111h 19In The TrenchesConsiderations Unique to Acquiring a Software Company (Financial)Acquiring any business is hard. Acquiring a software company is no exception, and indeed may prove to be even more intimidating to the inexperienced acquiror due to certain non-obvious considerations unique to software companies and the business models under which they operate.
In this audio blog, I explore several of these unique and non-obvious considerations for the prospective software acquiror to consider based on my own experience acquiring, running, and selling a small- to medium-sized software company over the course of many years. Specifically, for every topic that I profile, I discuss why it’s important to dig one level de...
2021-10-2818 minIn The TrenchesWhat M&A Lawyers Want CEOs to Know About Selling Their CompaniesToday's episode is all about the legal issues and considerations involved in selling a small to medium sized business ("SMB"), many of which tend to be unfamiliar to CEOs and Entrepreneurs.
My guest, Mario Nigro, is one of Canada's preeminent M&A lawyers, and currently serves as a Partner in the Mergers & Acquisitions and Private Equity & Venture Capital Groups at Stikeman Elliot based out of Toronto. From a legal standpoint, Mario has worked with substantially every type of stakeholder within the SMB ecosystem (business owners, CEOs, entrepreneurs, strategic acquirers, private equity firms, banks, non-bank lenders, financial advisors, d...
2021-10-141h 17In The TrenchesLessons From my First Month as the CEO of a Newly Acquired CompanyIn January, 2014, I became the CEO of a software company (after having acquired it from its original founders), powered by all of the wisdom and experience that one would expect from a 27-year-old who had never managed as much as a fruit stand in his entire life. The pace was intense, the volume of information to be processed was overwhelming, and the lessons learned were numerous.
In this audio blog, with the benefit of 10 years' worth of hindsight and perspective, I attempt to share with you some of the major lessons and observations gleaned from my few months as the...
2021-09-3020 minIn The TrenchesRich Manders: Lessons from Founding, Growing, Buying, Selling, Coaching, and Investing in SMBsMy guest today is Rich Manders, who has essentially done everything that a CEO and Entrepreneur can do: He has founded companies, operated and grown them substantially, sold them (several times), acquired them (several times), and now acts as a coach for other CEOs and Entrepreneurs looking to do the same.
Rich Co-Founded and led iAutomation, a Massachusetts-based machine control and automation company, and grew the company from $0 to $90M in sales with 180 employees. After selling that business to The Riverside Company (a leading global Private Equity firm), Rich stayed on with the business, and alongside his p...
2021-09-161h 27In The TrenchesWhy Your Business Needs a Set of Core Values (or Why Yours May Not be Having an Impact)Early in my tenure as a CEO, I thought core values were tired, hollow, and meaningless platitudes that companies created simply because they felt they had to. Many of you may view them in a similar light. What I came to learn over time however was that my skepticism towards core values wasn’t because the CONCEPT of them was hollow and meaningless, but instead because so many companies had done such a poor job in establishing theirs, and as a result, their core values BECAME tired platitudes that nobody paid attention to.
We ev...
2021-09-0212 minIn The TrenchesBuilding and Managing a World Class Product Management DisciplineToday’s episode is specific to software companies, and is all about the Product Management operation. As most software executives can attest to, a non-functioning (or worse, a non-existent) product management operation can get companies into all kinds of trouble, and those problems often manifest across Engineering, Sales, Customer Support, and other areas. Some software companies, particularly more mature ones, often start out without a formalized product management discipline, but companies who pursue any degree of scale often quickly realize just how critically important this discipline is.
My guest today is Rich Mironov, who is...
2021-08-191h 04In The TrenchesBusting the Biggest Myth About Selling Your BusinessAs a business owner, if you're thinking about the sale of your company as being the singular event that will finally eliminate all of the risks that you've personally assumed for so many years, then I hate to be the one to tell you this, but: Think again.
Indeed, in my experience, the single biggest myth about selling a company is that the seller bears no further risk after the sale of his or her company is completed. In most cases, especially with respect to the sale of SMBs, this is simply not true.
In this audio blog, I will sh...
2021-08-0523 minIn The TrenchesUnderstanding and Managing The Psychological Toll of Being an Entrepreneur or CEOIn today's episode, I speak with Dr. Eliana Cohen, a Clinical Psychologist who works with (among others) a wide variety of Entrepreneurs and CEOs. Dr. Cohen's practice integrates performance psychology, strategy, emotional intelligence, and knowledge of neuroplasticity and the brain to serve her various clients. In our discussion, we cover a lot of ground including the psychological similarities that Entrepreneurs and CEOs tend to present, how to differentiate between healthy and unhealthy levels of worry and/or anxiety, how leaders tend to conflate their own happiness with the success of their businesses, signs to watch that may suggest that m...
2021-07-221h 21In The TrenchesLessons in Managing my own PsychologyBen Horowitz, the former CEO of Opsware and now world-renowned Venture Capitalist, once said: “By far the most difficult skill for me to learn as CEO was the ability to manage my own psychology . . . very few people talk about it . . . In the end, this is the most personal and important battle that any CEO will face.”
I suspect that almost all entrepreneurs and CEOs know exactly what he meant when he said this. My own experience taught me that unless you are deliberate about managing your own psychology as a leader, you risk becoming a sort of “victim”...
2021-07-0821 minIn The TrenchesCEO Coaches: What do they do, how do they work with CEOs, and why might you consider hiring one?In this episode I interview Warren Coughlin, who has been a Coach to SMB CEOs for upwards of two decades, helping them achieve everything from hugely successful exits, to 7-figure salaries, to significantly reduced day-to-day operational roles, and countless other outcomes.
Warren is the creator of The Business That Matters Playbook, a tool that streamlines and automates the strategic planning process for CEOs and Entrepreneurs. His coaching practice focuses not only on the business itself, but also on the entrepreneur at a personal level, working with them to ensure that they craft meaningful values and live a...
2021-06-241h 09In The TrenchesMigrating Your Software Company from On-Premise to SaaS (Part 2)In Part 1 of this Audio Blog, we evaluated some of the more common challenges that companies face when attempting to migrate both their product and revenue models from that of on-premise to SaaS. I guided my own company through this transition over many years. Though we did end up achieving some success, our transition ultimately went too slow, required too much time and capital, and came in below our initial targets. In this Audio Blog (Part 2), I leverage this first-hand experience to walk you through the tactics and strategies that you can put into place to make your own t...
2021-06-1022 minIn The TrenchesWhat I Learned During my First (Failed) Attempt to Sell my BusinessAs CEOs, many of you are undoubtedly considering the possibility of selling your business at some point in the future.
In 2018, I attempted to sell my own business, though was unsuccessful in doing so. From start to finish, the sale process took upwards of 12 grueling months. Hundreds of potential suitors were narrowed down to a dozen or so, which in turn were narrowed down to a single acquiror with whom we completed the extensive financial, legal, technical, and commercial due diligence process.
Just as we were beginning to draft the final purchase agreement, the transaction fel...
2021-06-0424 minIn The TrenchesConsiderations in Selecting Your M&A AdvisorAs CEOs & Entrepreneurs, I suspect many of you have at least considered the possibility of an exit, whether it be in the near or long-term future. In my experience selling my own business, the selection of my M&A Advisor was perhaps one of the most important decisions that I had to make, and in retrospect so many other decisions (and their outcomes) flowed directly from this one critical choice. I once chose a bad advisor, and have since worked with a great one.
Based on these experiences, I have an enhanced appreciation for the specific variables...
2021-06-0221 minIn The TrenchesPricing Power: How Small Changes Can Have Big ImpactsAs CEOs & Entrepreneurs, we all know that there are a countless number of levers that one can pull to grow revenue or profitability, all of which will have varying degrees of impact. Increasing prices is one such lever, however it is somewhat unique. In this audio blog, I explain why.
I argue that in certain circumstances, raising the prices that you charge to existing customers is one of the fastest, most effective, and “lowest friction” ways to unlock a nascent revenue and profitability opportunity that may reside within the base of customers that you already possess.
...
2021-05-3117 minIn The TrenchesThe Private Equity Perspective on Acquiring, Operating, and Selling Software CompaniesMy guest today is Jordan Bettman. Jordan is a Partner and Co-founder of Radian Capital, a New York-based Private Equity firm focused on B2B software and technology-enabled services businesses. Radian currently has ~$500 million of assets under management, and is now investing out of their second fund.
Prior to co-founding Radian, Jordan was a Partner at Bain Capital Ventures for nearly a decade, where he focused largely on financial services and back-office technology investments. He currently serves on the Board of Directors of 5 private technology businesses, and through Radian has made direct investments (both majority and minority...
2021-05-271h 28In The TrenchesMigrating Your Software Company from On-Premise to SaaS (Part 1)Today’s audio blog is specific to software, and concerns the migration from i) a business model characterized by on-premise hosting and one-time perpetual-use licensing fees, to ii) a new business model characterized by cloud-based hosting and a subscription licensing. This process is generally referred to as the "On-Premise to SaaS Migration".
Most software companies founded over the past fifteen years or so have never known anything other than the latter model, however, for anybody running a company still selling on-premise software under a perpetual-use pricing model (or is considering investing in one) , I'd humbly suggest that yo...
2021-05-2624 minIn The TrenchesHiring Your Senior Leadership TeamIn my experience as a CEO, I came to learn that surrounding myself with A+ people (particularly at the senior leadership team level) was one of the most impactful things that I could do for both myself and my company. Even if you are above average with respect to your ability to hire great people (most people think that they are – yet most people are not), it is a virtual guarantee that you'll make some mistakes as you build out your leadership team.
I certainly did. It took me many years (and many mistakes) to learn about gre...
2021-05-1720 minIn The TrenchesWhy So Many Companies Rarely Achieve Their Annual GoalsToday’s episode is all about execution, and more specifically what you need to do to give yourself the best odds of actually executing on the goals that you set for your organization.
There’s a well-known maxim that you might be familiar with that states “Strategy without execution is hallucination”, and in today’s audio blog I’ll share with you why I think that’s true. I’ll do so by sharing some of the lessons that I’ve learned over the years related to executing on the strategy you set. In my experience (and in the experience o...
2021-05-1722 minIn The TrenchesThe Entrepreneur and Mental Health (Part 2): My Advice to YouIn today's post, I share with you the lessons I’ve learned to deal with (or prevent, as much as possible) the mental health toll that entrepreneurship (or leadership, or success) can take: Of course, these lessons are only now clear to me with the benefit of hindsight vision being of the 20/20 variety. When you’re constantly in the trenches, like so many Entrepreneurs and CEOs are, it’s difficult to see the forest from the trees. For this reason, I hope you’ll find this Audio Blog to be highly practical, and full of strategies that you can actually...
2021-05-1316 minIn The TrenchesThe Entrepreneur and Mental Health (Part 1): My JourneyIn this Audio Blog, I provide you with a brief summary of my own mental health journey as a leader. My goal isn’t to provide you with an exhaustive account of my journey, but rather to simply discuss it publicly. After all, if I don’t do my own part to contribute to the discussion around the worries, thoughts, and fears that Entrepreneurs and CEOs face, what right do I have to lament that it isn’t being discussed enough more broadly? This will be my only Audio Blog solely about me. Though it may be less practical for yo...
2021-05-1319 minIn The TrenchesSales: Hiring, Onboarding, Compensating, Scaling & Supporting a World Class Sales TeamIn this episode I interview Dave Prusinksi, currently the Chief Revenue Officer at SafeAI, a hyper-growth silicon valley company in the autonomous vehicle space. Here is why I think Dave is a person worth listening to:
Prior to his current role, Dave spent 10 years as the Executive Vice President of Sales and Marketing at FleetComplete, a technology provider to fleet-owning businesses around the world. Under Dave's leadership, FleetComplete grew from $6M ARR to $150M in total revenue, achieving an average 50% revenue CAGR for 9 of his 10 years.
Dave played an in...
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