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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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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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!
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The Acquisition Entrepreneur and Mental 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*Over four years ago, in February of 2021, I decided to publicly share the emotional and psychological realities of my journey as an Entrepreneur and CEO between 2012 - 2020. In publishing my first ever blog post, I suppose I had four primary objectives:First, to make a small contribution to the collective understanding, awareness and discussion surrounding issues of mental health, particularly that of Entrepreneurs and CEOs.Second, to simply discuss my challenges publicly. After all, if I didn’t do my own part to contribute to the discussion around the worries, thoughts, and fears that Entrepreneurs and CEOs face, what right did I have to lament the fact that they weren't being discussed enough more broadly? Third, to speak to any leaders who might have been experiencing feelings similar to those which I had feltAnd, finally, to share some of the lessons that I had learned as a result of dealing with these challenges, some of which only became clear to me with the benefit of time and hindsightIn re-publishing that post today, my goals remain the very same. Though I had no plans or expectations after publishing the article in 2021, that single post was the first of 119 others that have followed over the past 4.5 years. I hope that at least one of these episodes has informed - perhaps even helped - some aspect of either your personal or professional life.
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Evaluating Customer Retention in Recurring Revenue Businesses: With Craig Zingerline
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 we take a deep dive into the concepts of customer retention and revenue quality in recurring revenue businesses. To help me unpack these ideas, I'm joined by Craig Zingerline, a serial entrepreneur who is now an advisor and mentor to a wide array of startups and technology companies. Among other things, we cover:A deep dive into the most common retention metrics, including which are most and least informativeSituations in which high retention metrics might actually tell you that something is wrong within the businessThings that he looks for that tend to be predictive of future customer retentionWhether he cares about the difference between voluntary and involuntary churnHow he thinks about software companies with high levels of service revenueWhether transactional revenue ought to be valued the same as per-user revenueAnd what else he looks at to evaluate the revenue quality of any given recurring revenue businessPlease 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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