A seasoned CEO shares personal insights on entrepreneurship, including challenges of isolation and uncertainty, psychological struggles like imposter syndrome and fear of failure, and embracing vulnerability for personal growth and leadership authenticity.

In this podcast, they discuss the importance of product management in software companies and how it can affect engineering, sales, and customer support. The guest, a product management expert, shares insights on hiring product leaders, prioritizing features, and dealing with sales requests. They also talk about the challenges faced by software CEOs in large sales transactions and the significance of soliciting feedback from customers and internal stakeholders.

Exploring the different forms of debt used in small business acquisitions, including bank debt, mezzanine debt, seller financing, and SBA loans. It evaluates the benefits and risks of each type of debt and how they can be leveraged effectively to finance business purchases.

Jay Davis and Jason Pananos, successful entrepreneurs who transformed their careers through strategic acquisitions, share their remarkable journey from $7 million to $50 million in revenue. They discuss the importance of timing and resilience during their growth phase, detailing how each acquisition shaped their trajectory. Insightful topics include navigating post-acquisition integration, the role of platform companies, and the nuances of building strong business partnerships. Their experiences reveal valuable lessons on maintaining adaptability and fostering relationships in the competitive world of business acquisitions.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * 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 is all about participating in brokered transactions, and working with brokers more broadly (by "brokers", I am referring to investment banks, accounting firms, business brokers, or any other sell-side advisor whose job it is to help clients sell their companies). To inform our discussion today, I’m joined by Ryan Farkas, a Partner, Managing Director and the Practice Leader in M&A and Capital Markets at BDO, who has successfully closed countless sell-side advisory transactions spanning dozens of industries.

Exploring the trend of industry roll-ups, challenges of fragmentation, post-acquisition integration, financing strategies, M&A growth considerations, and skeptical views on consolidation theses within the search fund ecosystem.

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 ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * In a previous post (75 Things That I Think Are True), I compiled quotes from countless books, mentors, podcasts and blogs to present 75 ideas that I believed to be fundamentally true, spanning both business and personal considerations. Since publishing that post last year, I have come across 45 additional quotes that I thought were also worthy of presentation. I hope that some of these new submissions also distill a lifetime of wisdom into only a few words.

Explore Constellation Software's playbook for acquiring and growing software companies, focusing on key metrics, the rule of 40, criteria for business leaders, transitioning older companies to SaaS models, enhancing software applications, managing seller involvement, and effective product management post-acquisition.

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 ⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠ * After many years of using company stock options as attraction, retention, and incentive alignment tools, I’ve come to appreciate their merits, risks, and possible alternatives. I intend to share these lessons with you today. More specifically though, I will argue that while options do have their time and place, there are often much simpler and less expensive alternatives that arguably have a greater impact on attraction, retention, and incentive alignment.

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠ * 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 entrepreneur, CEO, and best-selling author, Rob Dube. In 1991, Rob co-founded imageOne, a managed print services business based in Oak Park, Michigan, that has won countless awards across countless publications for it’s growth, culture, and employee engagement, among many other accolades.   Today we discuss Rob's newest book, Shine: How Looking Inward Is the Key to Unlocking True Entrepreneurial Freedom. This book is all about how CEOs can manage their inner worlds, which stands in stark contrast to most business books, that focus almost exclusively on how CEOs can manage their outer-worlds. Rob co-authored the book alongside Gino Wickman, who is the author of the widely-read Traction, the book that introduced the world to the Entrepreneurial Operating System ("EOS").