My Guest Today’s guest is Chris Hillier, an entrepreneur, investor, author, and longtime operator in the world of small and mid-sized businesses. He co-founded Benefit Health Advisor during the Great Recession, returned to Colorado after earning his MBA from Stanford, and over the next sixteen years helped grow the company at more than 30% annuallyContinue reading “The Case for Focus, Profitability, and Saying No to Growth for Its Own Sake”
Author Archives: sdivitkos
A Cybersecurity Survival Guide for Small Businesses
My Guest In 2026, you probably don’t need to look terribly far to read about both the frequency and seriousness of cyber attacks on both individuals and small businesses. Because of how unfortunately common these attacks have become, and because of how difficult they can be to understand if not explained at an appropriate levelContinue reading “A Cybersecurity Survival Guide for Small Businesses”
A Glimpse Into The First 90 Days as a New CEO
My Guest How to approach the first 90 days as a new CEO, including what to do and what not to do, is also among the most frequently asked questions that I’ve received over the past 14 years. For this reason, I thought it would be helpful to interview 3 CEOs, each at different stagesContinue reading “A Glimpse Into The First 90 Days as a New CEO”
The Most Meaningful Lesson that I’ve Learned Over the Past 12 Months
Today’s episode is a slight departure from our usual format, but I think it’s one that you’re really going to enjoy. Regular listeners of the show will know that I often conclude with the same question, and that question is: “What is the most meaningful lesson that you have learned over the past 12 months,Continue reading “The Most Meaningful Lesson that I’ve Learned Over the Past 12 Months”
A Peek Behind the Curtain: What Small Business Ownership *Really* Looks Like
My Guest The point of today’s episode is to give the uninitiated a peak behind the curtains, and to provide but one example of what leadership really looks like at the ground level. My guest today, Rishi Sahel, is a great example of a CEO who has withstood more than his share of punches toContinue reading “A Peek Behind the Curtain: What Small Business Ownership *Really* Looks Like”
$2B Company Founder on Youth, Inexperience, and Why You’re More Ready Than You Think
My Guest Ronnen Harary is the Co-Founder and Chairman of Spin Master Toys, the global children’s entertainment company behind PAW Patrol, Bakugan, Melissa & Doug, Rubik’s Cube, and Toca Boca. Alongside his longtime business partners, he co-founded Spin Master in Toronto in 1994 and eventually transformed it from a two-person startup into the fourth-largest toyContinue reading “$2B Company Founder on Youth, Inexperience, and Why You’re More Ready Than You Think”
When Both Sides Are Right: Navigating the Trade-Offs That Define Leadership
Listen to This Blog Post One of the most challenging aspects of leadership is navigating the seemingly endless collection of tensions and trade-offs that exist within any organization. These situations are difficult precisely because they rarely involve a choice between something that is clearly right and something that is clearly wrong. More often, leaders findContinue reading “When Both Sides Are Right: Navigating the Trade-Offs That Define Leadership”
The Wisdom of Failure: Growing from our Personal and Professional Setbacks
My Guest Dr. Larry Weinzimmer is a Professor of Strategic Management at Bradley University and is the best-selling author of The Wisdom of Failure, a book based on a groundbreaking 7-year study of what 1,000+ managers across 21 industries really learned from their personal and professional failures. In addition to being a best selling author,Continue reading “The Wisdom of Failure: Growing from our Personal and Professional Setbacks”
Ten Ways to Underwrite a Conservative and Realistic Base Case
Listen to This Blog Post When building a model and underwriting an acquisition more broadly, many prospective acquirors understandably struggle with how to balance calculated optimism about the future on one hand, with a sense of what is realistically achievable on the other. While investing is an inherently optimistic act (after all, you wouldn’t makeContinue reading “Ten Ways to Underwrite a Conservative and Realistic Base Case”
Hiring Your Second in Command: With Cameron Herold, Founder of the COO Alliance and Former COO of 1-800-GOT-JUNK
My Guest Cameron Herold is the former COO of 1-800-GOT-JUNK, a franchised junk removal business that he helped grow from $2M to $106M in revenue during his 6-year tenure as COO. Based on that experience, in 2016 Cameron founded the COO Alliance, a peer group for Chief Operating Officers (or those whose roles are bestContinue reading “Hiring Your Second in Command: With Cameron Herold, Founder of the COO Alliance and Former COO of 1-800-GOT-JUNK”