In this episode of Max Value, host Ben Towne is joined by Sarah Craven, certified financial planner and exit planning adviser at Sand Hill Global Advisors, to discuss the fundamentals of exit planning for business owners. Using the analogy of a three-legged stool, they explore the three pillars of a successful exit: the business, the personal, and the financial. They emphasize that there is no one right time or one right answer — every exit looks different and must be driven by the individual owner’s goals, legacy, and life vision. Key topics include the readiness gap, the value gap, the wealth gap, deal structure, timing the market, and the emotional challenges of leaving a business. Both guests stress the importance of assembling a team of professionals early, starting with a business valuation as a triggering event, and recognizing that exit planning is simply good business planning done well in advance.
Chapter 1 – Welcome to Max Value
Ben Towne introduces the podcast and welcomes Sarah Craven, chief wealth manager and certified exit planning adviser at Sand Hill Global Advisors in Silicon Valley. The episode frames around exploring the fundamentals of exit planning for business owners.
Chapter 2 – Why Wealth Advisors Are Turning to Exit Planning
Sarah explains her motivation for branching into exit planning: she was struck by the statistics showing how many business owners feel unhappy, unprepared, or uninformed after selling. She notes that exit planning is closely aligned with the financial and personal planning work she has been doing for almost 30 years.
Chapter 3 – The Three Pillars of Successful Exit Planning
Sarah introduces the three-legged stool analogy: the business leg, the personal planning leg, and the financial planning leg. Each pillar is equally important — neglecting or under-weighting any one of them results in a wobbly stool and a sub-optimal exit outcome.
Chapter 4 – When Is the Right Time to Exit Your Business?
There is no one right time to exit — the decision must be driven by the individual owner’s needs, readiness, and goals. Ben and Sarah compare it to selling a house: market conditions matter, but only as part of a broader personal and financial plan that addresses where you’re going next.
Chapter 5 – The Personal Side of Exit Planning: Identity, Legacy, and Life After Business
The personal pillar covers identity, legacy, family dynamics, and life vision after the sale. Sarah highlights that this process can be emotionally taxing — almost like therapy work — and that business owners must reflect on what they want to leave behind, who they will be after the exit, and how their day-to-day life will change.
Chapter 6 – Financial Planning for Business Owners: Bridging the Wealth Gap Before Exit
The financial leg of the stool centers on identifying and closing the wealth gap — the space between what the owner has today and what they need to fund their retirement vision. Key elements include personal financial goals, investment strategy, income replacement, risk management, and pulling in tax advisors and estate planning attorneys to create an effective and efficient exit.
Chapter 7 – Is Your Business Ready to Sell? Closing the Readiness and Value Gaps
The readiness gap assesses whether a business is truly ready and able to be sold, identifying landmines such as owner dependency, customer concentration, or weak financials. The value gap addresses the difference between the business’s current appraised value and the amount needed to fund the owner’s exit plan — a gap that can often be closed by improving growth, reducing risk, and increasing profitability.
Chapter 8 – Timing Your Business Exit: Market Conditions, Deal Structure, and Long-Term Strategy
Even in a favorable market, a business with unresolved landmines will struggle to attract buyers or command a fair price. Ben walks through the reality of a sale process — typically 9 to 12 months — and highlights that earnouts and employment contracts mean the exit isn’t truly complete until all the money is received. Deal structure, private equity rollovers, and post-sale involvement are also discussed.
Chapter 9 – Exit Planning Is Just Good Business Planning
Good exit planning is simply good business planning done early. Using the house renovation analogy, Ben and Sarah illustrate that improvements made early allow the owner to both enjoy the upgrades and maximize value at sale — whereas last-minute fixes may not be enjoyed, and doing nothing risks getting hammered on price. Business value, unlike home value, can deteriorate quickly.
Chapter 10 – How to Start Exit Planning: First Steps for Business Owners
The first step is recognizing that the process may take three to five years and that no owner should go through it alone. Sarah recommends surrounding yourself with a great team of advisers, starting with a business valuation as a triggering event that can either confirm readiness or reveal what needs to be built. Ben reminds owners that selling a business is usually a one-time decision — there is only one at-bat to get it right.
Chapter 11 – Legacy, Fulfillment, and the Human Side of Exit Planning
Both Ben and Sarah reflect on what drives their work: relationships, impact, and legacy. Ben connects his focus on small business owners to his own family’s history of entrepreneurship, emphasizing that payoff doesn’t always mean money — it means blood, sweat, and tears translating into a meaningful outcome. Sarah closes by recommending John Warrillow’s The Art of Selling Your Business, noting that selling a business is an art, not just a science.
