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  *  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!

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 Hiring, and we've managed to secure one of the world's foremost experts on the subject.Randy Street is the Vice Chairman of ⁠ghSMART⁠, a global consulting firm that helps CEOs, boards, and investors build valuable companies specifically through hiring and developing world class leadership teams. Alonside ghSMART's chairman and founder, Geoff Smart, Randy also co-authored ⁠Who: The A Method for Hiring⁠, a book that I view as being required reading for all entrepreneurs and CEOs running SMBs. The very specific hiring method that they detail within this book ("Topgrading") changed the way that I made all of my hires across my entire company.In our discussion today, we discuss how to evaluate people & teams that you haven't personally hired, post-hire considerations, lessons from 30+ years of working with CEOs and management teams, compensation, and how to identify and address conflicts within leadership teams.

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  *   Across all known search funds since the inception of the model in the 1980s, ~63% of funds have gone on to acquire a company. However, since 2014, the acquisition rate has decreased, hovering around ~57% over the past 10 years. Today I'm joined by three of the most experienced and respected investors within the search fund ecosystem to discuss A) Why the acquisition rate among search funds has fallen over the past 10 years; and B) Whether the rate of acquisition is likely to fall further in the years to come.Joining me today are Jim Edmunds (Search Fund Partners), Badge Stone (WSC), and Kent Weaver (Granite Point Partners).Today's episode revolves around the testing of 8 hypotheses, submitted to us via a survey of 1,000+ searchers & CEOs. Those hypotheses include:Encroachment: PE moving further down market?Capacity: Investors with too many searchers in their portfolios?Competition: Too many search funds in the market?Dilution of Talent/Commitment: Too many part-time searchers?Valuation Expectations: Sellers no longer willing to transact at palatable multiples?Cost of Capital: Search funds have a higher cost of capital relative to other buyers?Searcher Fatigue: Sellers and intermediaries becoming disillusioned with the value proposition of search funds?Email: Deliverability challenges too much to overcome?Please enjoy!

This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle 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 by⁠⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠*Raam Jani is one of the most experienced lawyers in the Search Fund ecosystem, and within the small business M&A ecosystem more broadly. In our discussion today, we cover some mechanics (including when one should begin the legal diligence process, how to avoid overwhelming sellers with too many information requests, and how he deals with situations where his legal counterpart is less experienced in matters of M&A). We cover frequent stumbling blocks within the M&A process (including how to evaluate the true extent of the key person risk that resides within any given seller, what areas of the purchase agreement tend to be most contentious, and why he advocates for rep & warranty insurance). And finally we conclude with some general market observations, including whether he thinks the lower middle market is as inefficient as it was 5-10 years ago.

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  *   As an American searcher, are you aware that you might be able to receive $10M+ of your exit proceeds completely free of federal tax? As a Canadian searcher, are you aware that you might be able to receive $1M+ of your exit proceeds completely free of federal tax? If you're not, then you might want to give this episode a listen. We split today's episode into two parts: The first half will focus on US searchers and investors, and will explore the QSBS program (aka Section 1202) offered by the US federal government. The second half (starting at the 47 minute mark) will focus on Canadian searchers and investors, and will focus on the CCPC program and the lifetime capital gains exemption offered by the Canadian federal government. Both programs have the potential to be incredibly lucrative for searchers and investors alike, though both remain unfamiliar to many. I hope this episode plays a small role in changing that. Timestamps - USA: 0:00 - 47:00- Canada: 47:00 - 1:11:00

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 * Dr. Daniel Crosby is a behavioral finance expert, the Chief Behavioral Officer at Orion Advisor Solutions, a Clinical Psychologist, and a New York Times best-selling author. In our wide-ranging discussion today, we discuss meaning, purpose, fear of the unknown, when to continue vs. when to persist, why we tend to ignore simple solutions to complex problems, why pessimism sounds more intelligent than optimism, how to use our money to buy back time, and how to spend our money in ways that will maximize happiness and contentment.

This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and small business audit services 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     *     The "long term hold” strategy is one that has received an increasing amount of attention within the acquisition entrepreneurship ecosystem of late. To further explore this thesis, I was joined by Zac Carman, CEO of ConsumerAffairs.com for 14+ years. In our discussion, we unpack Zac's long-term-hold strategy and discuss the extent to which it was deliberate or emergent, how he has managed liquidity requirements for both himself and his investors, the commercial and personal reasons why a LTH strategy makes sense for him, and if he thinks it makes sense for an entrepreneur to target a LTH strategy before acquiring their first company.

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     *     Archimedes said “Give me a lever long enough, and a place to stand, and I will move the earth.” Though the concept of leverage is most commonly associated with the use of debt to finance the acquisition or operations of a company, there are countless other forms of leverage that we ought to be aware of, given that all of us have to contend with the reality of finite time and resources. Instead of asking what else they should be doing to achieve their goals, entrepreneurs and investors might instead consider asking: “How can I magnify the impact of what I'm doing, without doing more of it?”. Today we explore 10 different forms of leverage, and provide a few ideas around practical application.

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     *     Want to know what it's like to work with me as an investor? ⁠⁠⁠Check out our testimonials page here⁠⁠⁠.     *   Those who have never run a rapidly growing company are unlikely to appreciate the operational challenges associated with doing so. Indeed, while running my own company, I found our highest growth year to be the most difficult, both operationally and personally. We outgrew our systems, had to change our people, had to add entirely new departments, and I found that my own role as the CEO had to evolve both quickly and significantly. To help us better understand the day-to-day realities associated with running a high-growth company, we're joined today by Anth Georgiades, co-Founder and CEO of Zumper, North America's largest apartment rental platform. Since it's founding in 2012, Zumper has grown revenue at triple-digit annual growth rates, and has raised over $150M in Venture Capital funding. Today, Zumper boasts over 250 employees, and 75 million active users.

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     *     Want to know what it's like to work with me as an investor? ⁠⁠Check out our testimonials page here⁠⁠.     *   Franchise ownership is an entrepreneurial path that remains under-discussed and under-explored within the small business community. Yet, for the right person, it can represent a highly lucrative opportunity with several built-in risk mitigation mechanisms. My guest today, Michael Horowitz, acquired 7 Wingstop locations in 2018 and continued to grow his footprint over the next 5 years until a successful exit to a strategic acquirer in 2023. As we discuss in our conversation, the entrepreneurial gods don't deduct any points for leveraging a business model that is proven to work.

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     *     Want to know what it's like to work with me as an investor? ⁠Check out our testimonials page here⁠.     *   Back by popular demand today, for his second tour of duty on the podcast, is Brent Beshore. Brent is the Founder and CEO of Permanent Equity, a private investment firm that invests in Founder-owned small to medium sized businesses. Beyond his commercial acumen, one of the things that I most admire about Brent is how he takes a deeply personal approach to his work, utilizing tools and frameworks from disciplines like philosophy, psychology, and religion to inform how he thinks about conducting himself both personally and professionally. This is one of the reasons why a seemingly black and white conversation about investing went into domains like fear of failure, the source of our identities, and why young professionals ought to demonstrate more vulnerability, among other topics. My first conversation with Brent, published in November of 2022, was one of our most highly rated episodes, and something tells me that this one might even top it.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * Want to know what it's actually like to work with me as an investor? Check out our testimonials page here. * Today's episode features five unrelated thoughts on how to lead and grow a healthy and vibrant company. None of them are long enough to justify a stand-alone blog post, but all of them are important enough to highlight for current and aspiring CEOs.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * Properly managing the relationship with the outgoing seller is likely to be among your most important tasks within your first 6 months as the new CEO. I say this because a non-functional (or worse, a toxic) relationship between the incoming and outgoing owners has the potential to damage a company more than customers leaving, employees quitting, or competitors fear-mongering ever could. To help us better understand the perspective of a selling Founder, I was joined this week by three founders, all of whom chose to sell their companies to a Search Fund within the past few years. Joining me today is Alicia Browner (Founder of Prelude), David Marshall (Founder of Performio), and Robert Day (Founder of Integrity Advocate).

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * Rich Manders has done almost everything that an entrepreneur and CEO can conceivably do: He co-Founded a Massachusetts-based automation company and grew it to $90M in revenue. He sold that business to a Private Equity firm, then stayed on with the business to help them acquire 7 tuck-ins, growing the company by 6x and producing a 50% IRR. He has since started a coaching practice, and now works with SMB CEOs across North America. His story is the subject of a Harvard Business School case study, where he has also taught several courses and seminars. Our discussion today covers how PE buyers are likely to evaluate your business, including internal systems, capital allocation, management team quality, pricing, and countless other variables.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * Today I am thrilled to welcome Carl Richards to the podcast. Carl has spent decades as a Certified Financial Planner, is the creator of the Sketch Guy column (which appeared weekly for a decade in The New York Times), is a best selling author (most notably of The Behavior Gap: Simple Ways to Stop Doing Dumb Things with Money), is a podcaster (most recently, the host of 50 Fires: A Podcast About Money and Meaning), and is a frequent contributor to countless financial and other publications, including Morningstar Advisor, Marketplace Money, Oprah.com, and Forbes.com, among others. In our conversation today, we cover: How in some instances money can indeed buy happiness; Why money is like alcohol; Why you should aim to “die with zero”; How to run small experiments to see what types of spending are likely to produce happiness for you; Why you may want to think about money as you would gathering firewood in a remote cabin in the wilderness; And much, much more.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * As an entrepreneur myself, it's clear to me that in some ways the realities of my chosen career path have magnified and heightened the challenges that are common to all relationships, and in other ways have added completely new dynamics that most other couples can't directly relate to. Today, I attempt to shine a light on the role that spouses play in the entrepreneurial journey from the perspective of both the spouse and the entrepreneur. To help me do this, I'm joined by Dr. Jennifer Musselman, a globally-recognized Marriage and Family Therapist and Executive Coach for high-performing executives and entrepreneurs. Dr. Musselman's clinical work focuses on the interplay of work, life, self-identity and marriage, including the common stressors that impact performance and relationship satisfaction for entrepreneurs and other business leaders. Link to The Entrepreneur and the Spousal Relationship: Part 1

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * Today I'm joined by 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, we had a very wide ranging conversation that I think you're really going to 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 ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * 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 integrated suite of K-12 school safety software. Jim ultimately sold the company to JMI Equity, and returned an astounding 13.5x MOIC and 53% IRR to his search fund investors. Jim also served in the United States Marine Corps in the Special Operations forces and was awarded the Combat Action Ribbon and the Navy and Marine Corps Achievement medal for his service in Iraq in 2004. Jim graduated from Amherst College with his bachelor's degree in Economics and Spanish and earned his M.B.A. from the Wharton School in 2006.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * 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 anxious about what mix of equity and debt to include in a letter of intent, but was instead anxious about the prospect of not finding a company to acquire at all after spending two years in pursuit of one. For this reason, I thought it might be helpful to compile some of the lessons that I've learned over the years that cover the “human side” of acquisition entrepreneurship. I hope at least one of them provides you with a reason to reflect on your own situation, and perhaps make a change for the better in the process.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * 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 is acquired and led by a CEO with minimal industry experience. It is also my experience that many problems that seem to be attributable to the engineering group (technical debt, high levels of customization, regularly missing deadlines, etc.) are actually product management problems masquerading as development problems. This episode, originally published in 2021, is as applicable today as it was then. My guest today is Rich Mironov, who is North America's preeminent Product Management thought leader. He has spent 40 years in the software industry in numerous capacities, and currently acts as a Coach, Consultant, and Interim Executive for CEOs and Heads of Product across Canada and the United States, advising them on a diverse range of issues spanning product, marketing, engineering, and sales. Rich has led Product Management at six software companies, and has now consulted for more than 170 technology businesses of all sizes. He is the author of "Product Bytes", a hugely popular and long-running blog on software, start-ups, product strategies, Silicon Valley, and the inner life of product managers. Our conversation covers hiring a Product leader and Product team, how to think about prioritizing products/features/functions, how Product should interface with Sales and other internal departments, how involved CEOs should be in Product, and what fatal mistakes he's seen Product Managers make.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * 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 bank debt, mezzanine debt, seller financing, and SBA loans.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * 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 graduating from business school in 2008, acquired Vector Disease Control, a company that they grew from ~$7M to ~$50M in revenue in ~7 years through successfully executing on 14 bolt-on acquisitions.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * Today'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 countless sell-side advisory transactions spanning dozens of industries.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * 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 I'm not against consolidation theses in and of themselves, I do find myself more skeptical than most when presented with one. In today's blog post, I'll attempt to explain why

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * In a previous post (75 Things That I Think Are True), I compiled quotes from countless books, mentors, 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 only a few words.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠ * Constellation Software is one of the world's most widely followed and admired software companies, having acquired 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 Constellation, that itself owns upwards of 200 portfolio companies.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠ * After many years of using company stock options as attraction, retention, and incentive alignment tools, I've come to appreciate their merits, risks, and possible alternatives. I intend to share these lessons with you today. More specifically though, I will argue that while options do have their time and place, there are often much simpler and less expensive alternatives that arguably have a greater impact on attraction, retention, and incentive alignment.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠ * Today I'm joined by entrepreneur, CEO, and best-selling author, Rob Dube. In 1991, Rob co-founded imageOne, a managed print services business based in Oak Park, Michigan, that has won countless awards across countless publications for it's growth, culture, and employee engagement, among many other accolades.   Today we discuss Rob's newest book, Shine: How Looking Inward Is the Key to Unlocking True Entrepreneurial Freedom. This book is all about how CEOs can manage their inner worlds, which stands in stark contrast to most business books, that focus almost exclusively on how CEOs can manage their outer-worlds. Rob co-authored the book alongside Gino Wickman, who is the author of the widely-read Traction, the book that introduced the world to the Entrepreneurial Operating System ("EOS").

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠ * Many searchers understandably tend to have very similar questions and areas of uncertainty. Indeed, in most instances, I had 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 these questions, I've presented each of them in today's episode, and have also included my opinion on what the answers may be. Some of the questions include: Constructing a cap table Differences between the Canadian and US search ecosystems Is the search fund market too crowded/saturated The trade-off between price and business quality What the best searchers do in their first 3-6 months Proprietary vs. brokered deal flow generation When to visit a prospective seller Success rates of industry agnostic searches Having an industry & geographic focus Homogeneity among search investors re: industry preferences How to spend your first week as a new CEO Should I create a 100-day plan? How to communicate the ownership change to customers

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠ * Today I'm joined by Entrepreneur, Investor, and Author Mike Michalowicz. In addition to being the author of 9 books, 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 make him successful, including (and especially) his "Profit First" system, a highly tactical guide to organizing your entire company around achieving endurable profitability.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠ * Today I am thrilled to be joined by two guests that, without the risk of hyperbole, have changed my life in more ways than 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 which focus on how to acquire, finance and operate your own smaller firm. They also co-published the widely read book, The HBR Guide to Buying a Small Business, published by Harvard Business Review Press, which acts as the definitive source of wisdom and guidance for a countless number of acquisition entrepreneurs

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠ * Today I'm joined by two of the most thoughtful, distinguished, and respected investors in the ETA ecosystem, Jeff Stevens and A.J. Wasserstein, to discuss the future of acquisition entrepreneurship. The paper that inspired this episode, written by both Jeff & A.J., can be accessed here: Jeff Stevens is the Founder of Anacapa Partners, a firm with over 20 years of experience structuring, operating and investing in search fund-owned companies. Jeff was an acquisition entrepreneur himself, having managed 3 funded searches during the period from 1990-2005, each one culminating in the acquisition of a SMB. A.J. Wasserstein is the Eugene F. Williams, Jr. Lecturer in the Practice of Management at the Yale School of Management. His research, writing, and teaching concentrates on search funds, entrepreneurship, programmatic acquisitions, and small businesses. In addition to his role as an educator, A.J. is also a private investor in lower middle-market businesses.

This episode is brought to you by ⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠ * Today I'm joined by Michael Girdley, an entrepreneur and investor who has spent the past 30 years building a personal holding company boasting over $100M in annual revenue, comprised of 12 businesses across software, technology, consumer retail, and education, among others. Outside of managing his holding company, Michael is deeply involved in the North American SMB ecosystem: He co-hosts Acquisitions Anonymous, a podcast that reaches over 10,000 listeners weekly, where he and his co-hosts dissect real businesses currently up for sale. He also offers two online courses, educating prospective entrepreneurs on the Holding Company model, as well as best practices on how to find and acquire a great small business. He is also an active investor in small- and medium-sized software companies through another holding company, Dura Software, that invests in mission-critical B2B software companies spanning multiple niches.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠ * This episode is brought to you by ⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠ * Over many years of evaluating acquisition targets alongside searchers, I've found that certain questions tend to apply more often than not. I've presented each of these FAQs in today's episode, in hopes that they play a small role in how you structure your own due diligence process, and in turn how you think about the relative merits and risks of the opportunity in question. If you're a buyer, the list that follows can be thought of as a starting point for “Commercial Due Diligence 101”. If you're a seller, you should be prepared to address each of these questions and information requests if you're ever planning to sell your small to medium sized business. Please enjoy!

This episode is brought to you by ⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses * In today's episode, I will be speaking with 3 searchers, each of whom are at different stages of their respective search journeys. As I have done in the past, I will again be asking these guests only a single question: Knowing what you know now, if you could go back and re-do the first 90 days of your search, what might you do differently? This question is an important one because every searcher that I've ever met (including myself) learns so much along the way, and as a result we often reflect back on our first few months and wish we knew then what we know now. My hope is that this episode will help you learn from those who have come before you in this regard.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Symphony⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. ⁠⁠⁠⁠⁠Just go to ⁠⁠⁠⁠⁠the ⁠⁠⁠⁠Contact form on their website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and tell them that you're a listener of the podcast to receive this discount! * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by ⁠⁠⁠⁠⁠⁠⁠⁠August Felker⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company's insurance program, including any potential coverage 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 operation, including countless searchers and CEOs within the ETA community * Today I'm joined by Dr. Victoria Medvec, a Professor of Management and Organizations at the Kellogg School of Management at Northwestern University. In addition to her professorship, Dr. Medvec is the CEO of Medvec and Associates, a consulting firm focused on high stakes negotiations and strategic decisions. She is also the author of the best-selling book, Negotiate Without Fear, which was published in 2021. Dr. Medvec is a renowned global expert in the areas of negotiations, often advising senior executives and Boards of Directors from companies around the world. Her clients include IBM, Cisco, McKesson, General Electric, Merck, McKinsey, BlackRock, Goldman Sachs, McDonalds, Bristol Myers Squibb, and J.P. Morgan Chase, to name just a few.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by ⁠⁠⁠⁠⁠⁠⁠August Felker⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company's insurance program, including any potential coverage 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 operation, including countless searchers and CEOs within the ETA community * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Symphony⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. ⁠⁠⁠⁠Just go to ⁠⁠⁠⁠⁠the ⁠⁠⁠⁠Contact form on their website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and tell them that you're a listener of the podcast to receive this discount! * Today I'm joined by Peter Lehrman, the Founder and CEO of Axial Market. For those of you who don't know, Axial is the North America's #1 online platform that connects buyers and sellers of small and medium sized businesses. Axial is used by over 20,000 investors, M&A advisors and CEOs, allowing them to connect on a confidential basis to explore M&A, debt, buyout, and growth equity transactions, to name just a few. Over 10,000 transactions are posted each year on Axial, covering companies that generate anywhere between $2.5M – $250M in revenue. Prior to Axial, Peter worked in private equity at SFW Capital Partners and was part of the founding team at Gerson Lehrman Group (or “GLG”, for short), a platform where investors and other users are able to connect on-demand with experts spanning a countless number of industries and disciplines.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Symphony⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. ⁠⁠⁠⁠Just go to ⁠⁠⁠⁠⁠the ⁠⁠⁠⁠Contact form on their website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and tell them that you're a listener of the podcast to receive this discount! * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by ⁠⁠⁠⁠⁠⁠August Felker⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company's insurance program, including any potential coverage 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 operation, including countless searchers and CEOs within the ETA community * Kaley Klemp is a highly sought after CEO coach, YPO forum facilitator, and best-selling author. In 2015, Kaley co-authored The 15 Commitments of Conscious Leadership, a book that was met with instant critical and commercial success, and followed that up in 2021 with The 80/80 Marriage, a book about how to strengthen and build relationships between spouses using some of the tools, techniques and ideas that she had previously employed with her executive coaching clients. Within the Young Presidents Organization (“YPO”), Kaley has facilitated retreats for more than 200 member and spouse forums throughout the world, and is a highly sought after speaker, recently having presented at Google alongside her husband, and with her TED Talk, “Stop Trying to Change”, racking up over 20 thousand views on YouTube. Prior to her coaching, speaking, and facilitator roles, Kaley was a management consultant with Deloitte, and prior to that she was a student at Stanford University, where she earned a B.A. in International Relations and an M.A. in Sociology, with a focus on Organizational Behaviour.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by ⁠⁠⁠⁠⁠⁠August Felker⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company's insurance program, including any potential coverage 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 operation, including countless searchers and CEOs within the ETA community * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Symphony⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. ⁠⁠⁠Just go to ⁠⁠⁠⁠⁠the ⁠⁠⁠⁠Contact form on their website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and tell them that you're a listener of the podcast to receive this discount! * My guest today is Brent Belzberg, Founder and Senior Managing Partner of TorQuest, a middle market private equity firm that he founded in 2002 that has since grown to ~$5.5B in assets under management. In 2018, Brent was appointed as a Member of the Order of Canada, Canada's highest civilian honor, for his work as a business leader and philanthropist. He also received Queen Elizabeth II's Platinum Jubilee Medal in 2023 for his significant contribution to Canada and the province of Alberta.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Symphony⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. ⁠⁠⁠Just go to ⁠⁠⁠⁠⁠the ⁠⁠⁠⁠Contact form on their website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and tell them that you're a listener of the podcast to receive this discount! * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by ⁠⁠⁠⁠⁠August Felker⁠⁠⁠⁠⁠⁠⁠⁠⁠ (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company's insurance program, including any potential coverage 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 operation, including countless searchers and CEOs within the ETA community * I have debated whether to write this blog post for quite some time now. Because topics related to mental health tend to generate more engagement than other more commercially-oriented content, I didn't want this post to be interpreted as being hollow or self-promotional in any way, to the extent that it generates higher-than-normal clicks or page views for me. In spite of this, two things compelled me to finally publish this: (1) I wanted to simply discuss the topic of anxiety publicly, in hopes that my doing so will play some small role in helping others feel comfortable doing the same. (2) My hope is that some subset of readers will respond to some subset of the points below with a nod of their heads, and a sentiment of “Yes, I've felt something similar myself”.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by ⁠⁠⁠⁠August Felker⁠⁠⁠⁠⁠⁠⁠⁠ (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company's insurance program, including any potential coverage 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 operation, including countless searchers and CEOs within the ETA community * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Symphony⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. ⁠⁠Just go to ⁠⁠⁠⁠⁠the ⁠⁠⁠⁠Contact form on their website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and tell them that you're a listener of the podcast to receive this discount! * I have spent the past several weeks going through almost 3 years of In The Trenches archives to tease out all of the best insights that we've been able to collect from each of our guests specific to Compensation. I won't need to convince any CEO of how important compensation is, and how fraught with peril it can be when it isn't done right. Below is a list of our guests and topics, which include timestamps, so you can skip between the segments that are most interesting to you: (3:06) Verne Harnish: Crafting Company-Wide Compensation Plans (20:55) Dave Prusinski: Sales Compensation (37:48) Rich Manders & Brent Beshore: Equity or Options as a Form of Compensation (51:00) Jim Sharpe: Managing Wage Inflation & Salary Expectations (55:05) Randy Street: Surprising Lessons Specific to Compensation (1:03:05) Bob Pritchett: Compensation Mistakes

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Symphony⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. On September 8th, 2023, Symphony will be live-streaming a webinar on searchfunder.com all about the technical due diligence process when acquiring a software company. Use this link to sign up: ⁠https://www.searchfunder.com/event/view/1200⁠. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all 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! * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by ⁠⁠August Felker⁠⁠⁠⁠⁠⁠ (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company's insurance program, including any potential coverage 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 operation, including countless searchers and CEOs within the ETA community * I have spent the past several weeks going through almost 3 years of In The Trenches archives to tease out all of the best insights that we've been able to collect from each of our guests specific to Hiring. I won't need to convince any CEO of how important the hiring process is, and how fraught with peril it can be when it isn't done right. Below is a list of our guests and topics, which include timestamps, so you can skip between the segments that are most interesting to you: (3:30) Randy Street: Co-author of Who: The A Method for Hiring, which introduced the Topgrading hiring method to the world (22:39) Verne Harnish: Founder of the Entrepreneurs' Organization (“EO”), & author of Mastering the Rockefeller Habits and Scaling Up (37:43) AJ Wasserstein: Professor at the Yale School of Management. Prior 2x CEO and active SMB investor (43:40) Mike Zani: CEO of The Predictive Index, and author of The Science of Dream Teams (52:27) Steve Divitkos: Hiring Your Senior Management Team: Founder of Mineola Search Partners (1:12:50) Anthemos Georgiades: Hiring in High Growth Environments: Founder and CEO of Zumper, an apartment rental platform that boasts 250 employees, 75 million active users, and 17 million app visits per month (1:27:09) Nicholas Andrews: Hiring for the Finance & Accounting Function: Founder of The Aspen Consulting Group (1:42:40) Rich Mironov: Hiring in Product Management: One of North America's preeminent Product Management thought leaders, having spent 40 years in the software industry in numerous capacities (1:55:20) Dave Prusinski: Hiring in Sales: Former EVP of FleetComplete. Grew annual revenue by ~25x, achieving a ~50% revenue CAGR for 9 of his 10 years

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by ⁠⁠⁠August Felker⁠⁠⁠⁠⁠⁠⁠ (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company's insurance program, including any potential coverage 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 operation, including countless searchers and CEOs within the ETA community * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Symphony⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. On September 8th, 2023, Symphony will be live-streaming a webinar on searchfunder.com all about the technical due diligence process when acquiring a software company. Use this link to sign up: ⁠https://www.searchfunder.com/event/view/1200⁠. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all 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! * My guest today is Dr. William Irvine, author of the best-selling book A Guide to the Good Life: The Ancient Art of Stoic Joy, and one of the world's most influential writers on, and practitioners of, stoic philosophy. Dr. Irvine spent 38 years teaching at Wright State University in Dayton, Ohio, having recently earned Professor Emeritus status there. Dr. Irvine earned his BA in Mathematics and Philosophy from the University of Michigan and an MA and PhD in Philosophy at UCLA.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠Symphony⁠⁠⁠⁠⁠⁠⁠⁠⁠. On September 8th, 2023, Symphony will be live-streaming a webinar on searchfunder.com all about the technical due diligence process when acquiring a software company. Use this link to sign up: https://www.searchfunder.com/event/view/1200. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all 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! * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by ⁠August Felker⁠⁠⁠⁠⁠ (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company's insurance program, including any potential coverage 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 operation, including countless searchers and CEOs within the ETA community * Recently, searchers have voiced an increasing level of interest in targeting “VC orphan” companies as acquisition targets: These tend to be healthy and modestly growing companies that have raised at least one round of institutional venture capital, have achieved product/market fit, but have failed to produce the triple-digit growth rates that are all but required for them to continue to command the time, attention, and capital of their VC-backers. Might searchers also consider this very different company profile, in addition to that which has served as the foundation of the Search Fund investment vehicle over the past three decades? Today's episode attempts to explore this question, presenting observations that both support and refute the thesis.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by ⁠August Felker⁠⁠⁠⁠⁠ (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company's insurance program, including any potential coverage 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 operation, including countless searchers and CEOs within the ETA community. * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠Symphony⁠⁠⁠⁠⁠⁠⁠⁠⁠. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to ⁠⁠⁠⁠⁠the ⁠⁠⁠⁠Contact form on their website⁠⁠⁠⁠⁠⁠⁠⁠⁠ and tell them that you're a listener of the podcast to receive this discount! * My guest today is John Warrillow, author of the bestselling book Built to Sell: Creating a Business That Can Thrive Without You, and Founder & CEO of The Value Builder System, a sales and marketing software tool for business advisors to find, win and keep their best clients. Built to Sell was recognized by both Fortune and Inc magazines as one of the best business books of 2011, and has been translated into 12 languages since its initial publication. John is also the author of The Automatic Customer: Creating a Subscription Business in Any Industry and The Art of Selling Your Business: Winning Strategies & Secret Hacks for Exiting on Top. John is also the host of Built to Sell Radio, a hugely popular podcast where he has interviewed over 400 SMB founders about their exits. Forbes ranked Built to Sell Radio as one of the ten best podcasts for business owners. Before founding The Value Builder System, John started and successfully exited four companies.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠Symphony⁠⁠⁠⁠⁠⁠⁠⁠⁠. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to ⁠⁠⁠⁠⁠the ⁠⁠⁠⁠Contact form on their website⁠⁠⁠⁠⁠⁠⁠⁠⁠ and tell them that you're a listener of the podcast to receive this discount! * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by August Felker⁠⁠⁠⁠ (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company's insurance program, including any potential coverage 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 operation, including countless searchers and CEOs within the ETA community. * Today's episode is the second in a two-part series on when search funds don't go as originally planned. On last week's episode, we spoke with four entrepreneurs to get a first-hand account of how and why their paths deviated from their original plans. In today's episode, we look to compliment those first-hand accounts with reflections from Jim Sharpe, a highly respected search fund investor of almost 20 years, and himself a former Searcher and CEO. Today we ask Jim to discusses the trends, commonalities, and themes that he has observed among searchers who failed to consummate an acquisition, and also those who did consummate an acquisition, but failed to "thrive" thereafter, either commercially or personally. Please enjoy!

This episode is brought to you by ⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by ⁠⁠⁠⁠August Felker⁠⁠⁠ (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company's insurance program, including any potential coverage 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 operation, including countless searchers and CEOs within the ETA community. * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠Symphony⁠⁠⁠⁠⁠⁠⁠. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to ⁠⁠⁠⁠⁠the ⁠⁠Contact form on their website⁠⁠⁠⁠⁠⁠⁠ and tell them that you're a listener of the podcast to receive this discount! * If one were to attend a randomly selected group of Search Fund conferences, they'd be forgiven for thinking that every search fund is a smashing success. When I was both a searcher and a CEO, I often left these types of events with a certain sense of insecurity and self-doubt, as everybody seemed to be more successful, more confident in their abilities, and more decisive in their actions. Yet, the data does not at all support the idea that everybody seems to be doing better than you are: One-third of search funds reliably fail to acquire a business, and of those that do, roughly one-third of them fail to return more than 1.0x the original capital. In today's episode, we speak with four entrepreneurs whose ETA paths deviated from their original plans, not only to learn from their hard-earned wisdom, but also to celebrate their courage and the wonderful professional successes that they've all gone on to achieve since.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠Symphony⁠⁠⁠⁠⁠⁠. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to ⁠⁠⁠⁠⁠the ⁠Contact form on their website⁠⁠⁠⁠⁠⁠ and tell them that you're a listener of the podcast to receive this discount! * This episode is brought to you by ⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by ⁠⁠August Felker⁠ (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company's insurance program, including any potential coverage 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 operation, including countless searchers and CEOs within the ETA community. * Like many of you, I'm a sucker for a good quote. The best quotes often distill a lifetime of wisdom into only a few words, which is likely why some of them continue to resonate for decades (and in some instances, even centuries) after first being articulated. Over the years, I've compiled quotes from countless books, mentors, podcasts, and blogs, and in today's episode, I present this collection of quotes to you, in hopes that some of them impact you as much as they've impacted me. Most importantly though, I'm proud to finally be able to tell my wife that all of those years of highlighting books in bed have finally led to a tangible piece of output. I recognize that this is an typical format for our podcast, but my hope is that this episode will be more dense with wisdom and tactical advice than anything that I've published before (because the wisdom contained within is largely attributable to other people!). Please enjoy!

This episode is brought to you by ⁠⁠⁠Oberle Risk Strategies⁠⁠⁠, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by ⁠August Felker (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company's insurance program, including any potential coverage 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 operation, including countless searchers and CEOs within the ETA community. * This episode is brought to you by ⁠⁠⁠⁠⁠Symphony⁠⁠⁠⁠⁠. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to ⁠⁠⁠⁠⁠the Contact form on their website⁠⁠⁠⁠⁠ and tell them that you're a listener of the podcast to receive this discount! * To say that it's been an active 6-12 months in the banking sector would be an understatement: Beginning as recently as January, 2022, we've seen the US Federal Funds rate increase from .08% to 4.83%, the rapid collapse of Silicon Valley Bank, and the rescue of First Republic Bank by JPMorgan, representing the second largest bank failure in the history of the United States. Against this backdrop, CEOs and prospective acquirors of small businesses understandably have a lot of questions about their banking partners, their ability to secure loans, and the terms under which they might be able to do so. To get us up to speed on the state of lower-middle-market credit in North America, I'm joined by Anthony Rodriguez and Conor Tidgewell of Avidbank, who walk us through what has changed, the "new normal", and what it all means for entrepreneurs and CEOs running (or seeking to acquire) a small business. Please Enjoy!