In The Trenches

Craig Zingerline, a seasoned entrepreneur and mentor in growth marketing and product strategy, shares insights into customer retention in recurring revenue businesses. He dives into the most telling customer retention metrics and the surprising implications of high retention scores. Zingerline discusses the importance of different churn types and the value of upselling strategies. He also compares transactional versus per-user revenue models, highlighting what founders should focus on for long-term business sustainability. A must-listen for anyone in the startup world!

Dive into the fascinating world of asset intensity in acquisitions. Discover why the mere presence of capital expenditures shouldn’t automatically disqualify a business from consideration. Learn how to assess companies with heavier capital needs and why traditional EBITDA metrics might fall short. Explore alternative valuation metrics that can paint a clearer picture of a company's true worth. This discussion promises to challenge conventional thinking and offer fresh insights for savvy investors.

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!

Nicholas Andrews, Founder of Aspen Consulting Group, specializes in finance and operations consulting for small and medium-sized businesses. He delves into essential cash management strategies during economic uncertainty, emphasizing the impact of financial literacy among employees. Nicholas discusses the importance of transparency and how it enhances engagement, while also offering guidance on hiring finance leaders effectively. He encourages focusing on accomplishments rather than duties on resumes, ensuring that new hires can drive financial success in their organizations.

Collin Hathaway, Founder of Skylight Capital and a veteran of the home services industry, reflects on his entrepreneurial journey from acquiring a plumbing company during the 2008 financial crisis to navigating today's competitive market. He discusses the shift towards organic versus inorganic growth and the challenges of investor communication. Hathaway also shares personal stories about overcoming a heart attack and his insights on accountability, business valuation risks, and the importance of maintaining strong company culture amid financial pressures.

Discover the critical role of customer concentration in business acquisitions and how it shapes pricing strategies. The discussion emphasizes the need for diligent risk assessment when dealing with major clients. Learn about real-life case studies that reveal the complexities of valuation in companies with similar concentration levels. Explore strategies to mitigate risks associated with customer dependence and the importance of thorough due diligence. The insights shared highlight the necessity of robust planning as businesses grow and refine their outsourcing tactics.

In this enlightening conversation, lifelong entrepreneur John Ratliff shares his journey of scaling Apple Tree Answers through 24 successful acquisitions. He discusses innovative strategies that reduced employee turnover from 115% to 18%, emphasizing the importance of workplace culture and the 'Dream On' initiative. Ratliff also reveals insights on navigating M&A challenges, effectively transitioning CEO roles, and trusting instincts during acquisitions. His practical advice on fostering open communication and strategic delegation makes this discussion a treasure trove for service-oriented business leaders.

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.