Delve into the intricate world of software company acquisitions. Discover how unique financial metrics distinguish software deals from traditional purchases. Uncover potential hidden challenges like technical debt that can alter investment decisions. Learn about the critical importance of cash flow over mere revenue growth when evaluating potential acquisitions. Finally, explore various strategies for structuring deals to align with diverse investment theses. It's an insightful guide for anyone looking to navigate the software acquisition landscape!

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.

Join industry veterans Jim Edmunds, partner at Search Fund Partners, Badge Stone, co-founder of WSC, and Kent Weaver, investor in over 150 search funds, as they explore the declining acquisition rates in the search fund landscape. They analyze factors like increased competition from private equity and evolving valuation dynamics, particularly in software acquisitions. The discussion also highlights the importance of authenticity in building trust, confronting 'searcher fatigue,' and navigating the complexities of today’s market while remaining optimistic about future opportunities.

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

Dr. Daniel Crosby, a behavioral finance expert and New York Times best-selling author, dives into the psychological factors that shape our financial decisions. He discusses how fear and uncertainty influence spending and risk-taking, often leading us away from simple solutions. Crosby emphasizes the importance of purpose over material wealth, highlighting that true happiness comes from experiences and meaningful connections. He also explores the balance between persistence and knowing when to let go, urging us to spend wisely to buy back time and maximize joy.

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     *     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.

Discover the power of leverage beyond just financial strategies. Explore various forms of leverage that can boost productivity, including technology and strategic partnerships. Learn how a software CEO applies these concepts for exponential growth, prioritizing key features and niche markets. Uncover practical tips to maximize impact without increasing effort, making the most of limited resources for entrepreneurs and investors alike.

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.

Michael Horowitz, a savvy entrepreneur, transformed his career by acquiring and scaling 20 Wingstop locations before making a successful exit. He discusses the lucrative opportunities in franchise ownership and why it remains under-discussed among small business owners. Listeners will learn about the importance of choosing the right franchisor, the financial metrics that signal success, and insights on navigating franchise agreements. Horowitz also emphasizes the value of brand recognition and the benefits of structured support for first-time franchisees.