The Inspired Stories Podcast
David Tobin, founder and managing partner of TobinLeff, started with coupon books in college, built a B2B telemarketing firm that he scaled to 60 people and sold under pressure rather than on his terms, and then spent years piecing together what went wrong. That painful exit became the foundation for everything he built next: an MA advisory firm focused on marketing, technology, and professional services companies that has now guided more than 250 clients through valuations, acquisitions, and sales over 16 years. ✨ Key Insights You’ll Learn: * College coupon books that sold for more than expected and nearly bought back a few years later * How a trade show accidentally launched a B2B telemarketing firm aimed at financial services companies * Why positioning financial advisors as exit planning specialists worked in the mid-90s before anyone had a name for it * The difference between increasing EBITDA and increasing your multiple — and why both matter * Why one plus one doesn’t equal three in a roll-up and what TobinLeff learned the hard way * Growth, margins, transferability, and client retention: the four value drivers buyers actually measure * Why 60 to 90 days of prep before going to market changes everything * Deal fatigue is real: what happens when a seller takes their eye off new business during the process * Why getting on a plane to meet a prospective client won an engagement that a Zoom call never would have * The difference between business brokers, MA advisors, and investment bankers — and why it matters 🌟 David’s Key Mentors: * His Father (Sydney Tobin): Named his first company after him; passed away when David was young and shaped his early drive * His Mother: Her line — experience is what you get when you don’t get what you want — stayed with him through his hardest exit * His Three Partner Colleagues (Former Marketing Agency Owners): Proved that good business sense built over years of ownership transfers directly to MA advisory work * The Buyers and Sellers He Observed Early On: Watching deal rooms before doing deals himself taught him what actually mattered in the process 👉 Don’t miss this conversation about what business owners get wrong when they think about selling, why the most painful exit David had turned out to be the most useful, and what separates a firm that commands 7x from one that gets 4x. 🔗 Connect with David Tobin: Website: tobinleff.com 📤 Transcript Available: The Lesson David Tobin Learned Running a 60-Person Firm He Couldn’t Scale: Manage for Profit 📺 Watch on YouTube: Inspired Stories Podcast 🌐 Our Website: The Inspired Stories Podcast 📤 Special Thanks to Anthony Codispoti & AddBack Benefits Agency — Providing innovative employee benefits solutions that improve employee well-being while optimizing your bottom line. Website: addbackbenefits.com
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