E60: The M&A Truths No One Tells Founders | Advice from an Operator w/Brenda Jacobsen

What does it really take to sell your business — and are you actually ready?In this episode of the InOrganic Podcast, we sit down with Brenda Jacobsen, Managing Director at STS Capital Partners, a sell-side M&A advisory firm focused on helping founders and operators find the right strategic buyer — not just the highest bidder. What makes Brenda unique? She's not a banker by training. She's a former operator who built and sold three companies herself, including a regional network of medical clinics and a corporate mindfulness media company. She's been on your side of the table.Brenda walks us through the full arc of what it means to navigate a business exit — from the first internal conversation with your co-founders, to closing day, and everything in between.In this episode, we cover:🧠 Why most partner misalignments happen before you ever talk to a banker📋 The "Owner's Outcome Exercise" — a simple framework to get founders aligned on what success actually looks like⏰ When to start having exit conversations (hint: it's earlier than you think)📉 How to read the hidden clauses in your equity docs that could cost you control of your exit💰 Current M&A valuation ranges for digital marketing agencies (3–6x EBITDA) and what moves the needle🤖 Why you need to stop "BS-ing your AI story" — and what buyers actually want to see🏥 A fascinating case study on data ownership in outsourced radiology and why it changed the deal conversation entirely👻 How phantom equity can keep your key operators invested all the way through close❤️ The emotional side of selling — and how the right sell-side advisor acts less like a banker and more like a witnessWhether you're planning to sell in 12 months or 12 years, this conversation is packed with practical, honest advice from someone who has lived both sides of the deal table.Connect with Christian and AyeletAyelet’s LinkedIn: https://www.linkedin.com/in/ayelet-shipley-b16330149/Christian's LinkedIn: https://www.linkedin.com/in/hassold/Web: https://www.inorganicpodcast.co🎙️ Guest: Brenda Jacobsen, Managing Director, STS Capital Partners🌐 Learn more about STS Capital: www.stscapital.com📌 Subscribe to the InOrganic Podcast for weekly conversations on M&A, growth, and building businesses worth buying.#MergersAndAcquisitions #BusinessExit #Entrepreneurship #SellYourBusiness #PrivateEquity #MiddleMarket #MAStrategy #BusinessGrowth #Founders #InOrganicPodcast Hosted on Acast. See acast.com/privacy for more information.