In The Trenches

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠*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  *  Aaron Houghton is a serial entrepreneur, having launched more than 10 companies in his career, with the most famous arguably iContact, an email and marketing automation tool that he sold for $170M prior to his 30th birthday. Among countless other accolades, Aaron was selected as an E&Y Entrepreneur of the Year in 2008, and was listed to Inc Magazine's 30 Under 30 list in 2010. He now spends his time running Dory, a company that helps high performers under high levels of stress optimize their performance.In Aaron's words, his "success came with the hidden costs of long-term stress including panic attacks, debilitating anxiety, burnout, and mental breakdown”. We dig into the psychological realities of entrepreneurship quite deeply in our discussion today, and discuss how his struggles led to a five-year study of how entrepreneurs manage stress, and the tools & techniques they can utilize for achieving high performance while maintaining mental and physical health.

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 ⁠⁠⁠B⁠⁠⁠⁠⁠⁠⁠oulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠*Rob Markey is the creator of the Net Promoter Score ("NPS"), which has grown to become the de facto metric for measuring the health, loyalty and satisfaction of a customer base. He is also a longtime Partner at Bain & Company, where he founded and leads their Global Customer Strategy practice.Rob is the co-author of The Ultimate Question 2.0: How Net Promoter Companies Thrive in a Customer-Driven World, a New York Times and Wall Street Journal bestseller. Rob also teaches at Harvard Business School, and serves on several nonprofit and corporate boards, where he helps leaders build customer‑centric businesses.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠⁠*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 Sherman Black, a CEO coach who focuses primarily on leaders running small and mid-sized enterprises.  In our discussion today we cover a wide range of topics, including some of the following: Misconceptions around what CEO coaches do (and don’t do)When & how to hire a coachHow to think about cost and ROI in making that hiring decisionWhether a coach needs direct experience as a CEO themselvesWhether your coach should have a direct line of communication with your Board and/or senior leadership teamHow to quickly evaluate the health of the relationship between the CEO and her direct reportsHow coaches think about popular small business operating systems like EOS…and many others Please enjoy!

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 ⁠⁠⁠B⁠⁠⁠⁠⁠⁠oulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠⁠*Over four years ago, in February of 2021, I decided to publicly share the emotional and psychological realities of my journey as an Entrepreneur and CEO between 2012 - 2020. In publishing my first ever blog post, I suppose I had four primary objectives:First, to make a small contribution to the collective understanding, awareness and discussion surrounding issues of mental health, particularly that of Entrepreneurs and CEOs.Second, to simply discuss my challenges publicly. After all, if I didn’t do my own part to contribute to the discussion around the worries, thoughts, and fears that Entrepreneurs and CEOs face, what right did I have to lament the fact that they weren't being discussed enough more broadly? Third, to speak to any leaders who might have been experiencing feelings similar to those which I had feltAnd, finally, to share some of the lessons that I had learned as a result of dealing with these challenges, some of which only became clear to me with the benefit of time and hindsightIn re-publishing that post today, my goals remain the very same. Though I had no plans or expectations after publishing the article in 2021, that single post was the first of 119 others that have followed over the past 4.5 years. I hope that at least one of these episodes has informed - perhaps even helped - some aspect of either your personal or professional life.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠*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 we take a deep dive into the concepts of customer retention and revenue quality in recurring revenue businesses. To help me unpack these ideas, I'm joined by Craig Zingerline, a serial entrepreneur who is now an advisor and mentor to a wide array of startups and technology companies. Among other things, we cover:A deep dive into the most common retention metrics, including which are most and least informativeSituations in which high retention metrics might actually tell you that something is wrong within the businessThings that he looks for that tend to be predictive of future customer retentionWhether he cares about the difference between voluntary and involuntary churnHow he thinks about software companies with high levels of service revenueWhether transactional revenue ought to be valued the same as per-user revenueAnd what else he looks at to evaluate the revenue quality of any given recurring revenue businessPlease enjoy!

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 ⁠⁠⁠B⁠⁠⁠⁠⁠oulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠*Although the vast majority of Search Funds seek to acquire businesses that are both “asset-light” and “capital-light” (that is, companies that don’t have a large base of tangible assets that need to be added to, refurbished, or replaced to either maintain operations or pursue growth), I don’t believe that the mere presence of capex should necessarily disqualify a company from consideration. In this episode, we begin by exploring the circumstances within which capex can be a tolerable part of any given deal, and we’ll conclude by discussing how buyers should adjust their approach to valuation based on the asset intensity of the target company in question.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠*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’s episode explores the intersection of healthcare and private investing, and specifically explores the merits and risks of acquiring the actual healthcare providers themselves.To help me explore this thesis, I could think of no better guest than Scott Becker. Scott is a Partner in the healthcare groupat McGuireWoods, a full-service U.S. law firm that serves clients ranging from startups to Fortune 500 companies. He previously served on the Board of Partners of the firm and chaired the Healthcare group for nearly 13 years. He provides counsel to hospitals, Ambulatory Surgery Centers, surgical hospitals, pharmaceutical companies, single- and multi-specialty medical practices, and a variety of healthcare industry entrepreneurs. Please enjoy!

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 ⁠⁠⁠B⁠⁠⁠⁠oulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠*Today'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. 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 transparent CEOs should be with company financials, and then move to questions of capital allocation and how CEOs should think about spending the cash that they generate, and finally we conclude with several considerations related to hiring, specifically focusing on the question of how CEOs should think about hiring a senior finance & accounting leader.Please enjoy!

This episode is brought to you by ⁠⁠⁠⁠⁠⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠*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  *  My guest today is Collin Hathaway, the Founder of Skylight Capital, a micro-cap private equity firm that invests primarily within the home services ecosystem.Collin got his start as an entrepreneur after acquiring a small plumbing company at the outset of the great financial crisis in 2008. Since then, he has acquired and operated several other home services companies operating within the plumbing, HVAC, and roofing verticals, to name just a few. In our conversation today, we cover how the home services market has evolved since he first entered it in 2008, his views on organic versus inorganic growth theses within home services, whether the market is too competitive today, what he’s learned about the art (and science) of raising money, how he communicates bad news to investors, and what he learned from experiencing a heart attack at only 36 years old.

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 ⁠⁠⁠B⁠⁠⁠oulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠*When evaluating a small business to acquire, to suggest that some form of concentration is common is likely an understatement. Indeed, in most cases, concentration of some variety is a borderline inevitability. Though this often takes the form of customer concentration (the focus of this blog post), it can take other forms as well, including key person concentration, supplier concentration, reseller concentration, and technology/platform concentration, among other forms.The aim of this blog post is to discuss when customer concentration is acceptable (and when it is not), how to incorporate its associated risks into the transaction’s price and structure, how to diligence the likelihood of those risks manifesting, and the types of business models where the defection of large customers should be viewed as an expectation, and not as an improbable risk.

This episode is brought to you by ⁠⁠⁠⁠⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠*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's guest, John Ratliff, is a lifelong entrepreneur who founded a call center company called Apple Tree Answers, which he scaled through 24 separate bolt-on acquisitions, growing it over 3,000% prior to selling to a strategic buyer in 2012. He then went on to become a partner at an investment bank, where he has advised on countless small business transactions. All told, he has sat in nearly every seat at the M&A table — as a founder, buyer, seller, and now advisor. In our conversation today, we cover:How he reduced frontline turnover from 115% annually to 18% annuallyLessons from acquiring 24 companies, including what he did differently in deals 23 & 24 relative to deals 1 & 2How John stayed intimately connected to 650 employees across 24 locations How he designed himself out of the day-to-day operations, spending just 15–25 hours per week inside of his businessHow to spot real sellers, how to navigate the notoriously tricky transition between incoming & outgoing CEOs, and how to identify red flags in due diligencePlease enjoy!

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 ⁠⁠⁠B⁠⁠oulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠*If you have ever had to decide how to price a product or a service, or if you foresee yourself having to make such a decision one day, I implore you to listen to today’s episode, in no small part because of how many practical takeaways you’re likely to leave with.I’m joined today by Casey Brown, the founder of Boost Pricing, a consulting company that helps their clients with all things pricing, including not just setting prices, but also the often overlooked tactical details of how to actually go about executing on pricing changes.In addition to being the Founder of Boost pricing, Casey is also a prominent keynote speaker, having delivered a TEDx talk in 2015 with over 5 million views to-date. She has degrees in both Chemical Engineering and Business, and if you listen to our conversation today, you won’t be surprised to hear that Casey cares about three primary things when it comes to her clients: Being fearless about price increases, getting paid what they’re worth, and increasing profitability fast.

This episode is brought to you by ⁠⁠⁠⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠*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 week, I'm joined by Dr. Sherry Walling, a clinical psychologist, speaker, podcaster, and best-selling author. She is also the Founder of ZenFounder, which aims to help entrepreneurs and CEOs navigate issues of transition, rapid growth, loss, and any manner of complex human experience. She is also the host of the ZenFounder podcast, which has been called a “must listen” by both Forbes and Entrepreneur Magazine and has been downloaded more than 1M+ times.Sherry first came onto my radar when she published her first book, the aptly named The Entrepreneur’s Guide to Keeping Your Sh*t Together, which discusses many of the topics that we’ve explored over the years in this podcast related to managing your psychology as an entrepreneur and CEO.Her most recent book is titled Exit Strategy: The Entrepreneur’s Guide to Selling Your Business without Regret, which goes beyond purely commercial considerations, and explores the largely unexplored personal considerations specific to the largest transaction of most entrepreneurs’ lives.

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 ⁠⁠⁠B⁠oulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠*One of the most common investment theses among acquisition entrepreneurs revolves around building an internal sales function where no such function has existed in the past. While this makes intuitive sense on the surface, just how easy is it to build a sales team from scratch? Do you hire the leader first, or do you hire an individual contributor first? Does it matter if your sales reps have experience in your particular industry? How do you evaluate the success of new hires if you have a long sales cycle? How do you change an incentive compensation plan in the middle of a fiscal year? Should lead generation be outsourced or brought in-house? How involved should a SMB CEO be in sales? These are just some of the many questions that we explore with my guest this week, Dave Prusinksi. Dave is the Chief Revenue Officer at SafeAI, a hyper-growth silicon valley company in the autonomous vehicle space. 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 integral role in the acquisition of 6 companies, leading the sales and marketing due diligence processes, and ultimately integrating the operations of the acquired businesses into that of FleetComplete.  Dave was also a central member of the deal team helping to lead FleetComplete through multiple investment and acquisition rounds themselves, managing the sales & marketing due diligence processes in each instance.  Dave has served as a Revenue Coach to several SMBs, working directly with their CEOs and Heads of Sales to optimize their sales and revenue generation processes. All of the companies with whom Dave has worked thus far have now exited with great success.  

This episode is brought to you by ⁠⁠⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠*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 week, I attempt to educate listeners on several non-obvious considerations - highly specific to the enterprise software business model - that must form a core part of any diligence and deal structuring process. Today’s episode will be broken into 3 segments:In part 1, I will discuss several financial considerations that differentiate a software acquisition & diligence process from a more "traditional" oneIn part 2, I discuss several product-specific considerations that prospective acquirors ought to pay particular attention to, especially those who are non-technical, with no prior software experienceFinally, in part 3, I outline 5 very different ways in which prospective acquirors can go about structuring the acquisition of a software company, because – as you’ll hear – not all software investment theses are created equally.Please enjoy!