In The Trenches

In this engaging discussion, Chris Smith, Managing Partner at Spellbound Partners with over 25 years in software development, explores the elusive concept of technical debt. He reveals how shortcuts can lead to significant business problems and outlines common pitfalls in software companies. Chris underscores the necessity of thorough due diligence for acquirers, providing strategies for assessing and managing technical debt. With insights on hiring and growth, he highlights the importance of aligning tech strategies with investment theses.

In 2022, we launched Mineola’s first fund to help entrepreneurs navigate the tactical, commercial, and personal challenges that are an inevitable part of the acquisition entrepreneurship journey. Almost four years later, we’re excited to continue this work through Mineola Fund II. Playing a small role in helping people realize their entrepreneurial dreams has proven to be an incredibly fulfilling way to spend my professional life. I hope to be able to do this very same thing for many more years to come.

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

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

Sherman Black, a seasoned CEO coach with extensive leadership experience, shares valuable insights on the world of coaching for small and mid-sized enterprises. He debunks misconceptions about what coaches really do and explains when to hire one. The conversation dives into evaluating the ROI of coaching and the importance of a coach's relevant experience. Sherman also offers practical tips for managing relationships with boards and assessing team dynamics, along with advice on operating systems that can streamline business processes.

Explore the deep connection between entrepreneurship and mental health, highlighting the struggles of CEOs navigating isolation and pressure. Personal stories reveal the emotional weight of leadership, while discussions on self-care stress its necessity for sustainable success. The impact of imposter syndrome and burnout on young entrepreneurs is addressed, encouraging vulnerability and open conversations. Aligning actions with core values is also emphasized to foster a healthier mindset in leadership.

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.