By STS Capital
In a recent episode of the InOrganic Podcast, hosts Ayelet Shipley and Christian Hassold sit down with Brenda Jacobsen, STS Managing Director, to explore what it really takes to prepare for a successful business exit and why the emotional side of selling is often the most overlooked in an M&A transaction.
Unlike many traditional advisors, Brenda brings the perspective of someone who has lived through the process herself. Before joining STS, she built and sold multiple businesses, including a regional network of medical clinics and a corporate mindfulness media company. Having sat on both sides of the table, she shares candid insights into founder alignment, valuation expectations, deal readiness, and the realities of navigating an exit process.
At the center of the conversation is a powerful idea: most exits don’t fail because of the market, they fail because founders wait too long to prepare, avoid difficult conversations, or never fully align on what success actually looks like.
Key insights from the conversation:
- Start the exit conversation earlier than you think: Founders should run their businesses as if they could sell tomorrow. Waiting until burnout, market shifts, or external pressure forces the conversation can significantly reduce optionality and value.
- Alignment among partners is critical: One of the most common issues Brenda sees is not active disagreement, but assumptions that were never discussed. Through STS’ “Owners Outcomes Exercise,” founders identify their required and preferred outcomes before going to market, helping avoid misalignment later in the process.
- The emotional side of selling is real: Selling a business is often the largest financial and personal decision of an entrepreneur’s life. Brenda explains why the right sell-side advisor acts less like a transaction manager and more like a steady guide through uncertainty, emotion, and major life transition.
- Valuation expectations must be grounded in reality: While comparable transactions and EBITDA multiples provide a starting point, founders often anchor valuation expectations around personal financial goals rather than market realities.
- Hidden clauses in equity documents can impact control: Brenda shares a real-world example of founders discovering late in the process that minority investors held approval rights over key decisions.
- Strategic buyers care about outcomes: Founders must be able to demonstrate how innovation is driving real business outcomes rather than relying on broad narratives.
- Incentivizing leadership teams matters: The conversation also explores phantom equity and creative incentive structures that keep key operators aligned and motivated through diligence, transition, and post-close integration.
Throughout the episode, Brenda reinforces a theme that defines the STS approach: an Extraordinary Exit™ is built long before a deal begins. It comes from intentional preparation, aligned leadership, strategic positioning, and understanding both the financial and emotional dimensions of the journey.
Listen to the full podcast here: https://www.youtube.com/watch?v=NLT0a-9nqC8&t=331s