Technical Debt: What it is, How Much of it You Can Live With, and How to Incorporate it into an Investment Thesis
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*Chris Smith is the Managing Partner of Spellbound Partners, a a company that helps acquirors with technical due diligence, fractional CTO services, and outsourced development services, among other things. Chris has over 25 years of experience building software platforms, and is an expert in cloud computing and software as a service (SaaS). He has been a part of numerous founding startup teams and has led multiple teams through high-growth transitions.Much of what we discuss today is intended to uncover how much “technical debt” any given target company may possess within its code base. Though substantially every software company has some amount of technical debt, those that are weighed down by an asymmetric burden of it tend to experience very real business problems that non-technical acquirors and CEOs may not fully appreciate. As a result, prospective acquirors would be well served to thoroughly diligence the amount of technical debt possessed by any given target company, and proceed very carefully (or perhaps not proceed at all) with those companies who seem to possess much more than their fair share of it.
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1:26:21
Announcing the Launch of Mineola Fund II
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.
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Stress, Panic Attacks, Debilitating Anxiety, and a $170M Exit: iContact Founder Aaron Houghton
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.
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1:17:43
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Rob Markey: Creator of the Net Promoter Score and Founder of Bain's Global Customer Strategy Practice
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.
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1:19:35
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1:19:35
Building Better CEOs: Lessons From a Veteran Executive Coach
This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years*This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses * Today I'm joined by Sherman Black, a CEO coach who focuses primarily on leaders running small and mid-sized enterprises. In our discussion today we cover a wide range of topics, including some of the following: Misconceptions around what CEO coaches do (and don’t do)When & how to hire a coachHow to think about cost and ROI in making that hiring decisionWhether a coach needs direct experience as a CEO themselvesWhether your coach should have a direct line of communication with your Board and/or senior leadership teamHow to quickly evaluate the health of the relationship between the CEO and her direct reportsHow coaches think about popular small business operating systems like EOS…and many others Please enjoy!
The only podcast dedicated exclusively to Entrepreneurs and CEOs running Small to Medium Sized Businesses (SMB).
Nobody knows what it’s like to be an Entrepreneur or CEO unless you’ve been one. Though many understand the rewards of company leadership, very few understand the arduous journey that’s required to get (and stay) there.
I share my own lessons as an Entrepreneur and CEO, and interview experts spanning Sales, Leadership, Mental Health, M&A, and Operations (among others) all with a single goal: To improve the personal and professional lives of Entrepreneurs and CEOs running SMBs.
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