Securing Your Exit: A Business Owner Playbook for Succession and Long Term Wealth Planning

According to The Business Journals, a fresh piece frames succession and wealth planning as the next chapter every owner eventually has to write — and Greenhouse Grower's recent coverage of a Cultivate'26 panel makes the friction points painfully concrete. Four family-business leaders, including Walters Gardens CEO Karin Walters and Spring Meadow's Deppe, sat down to trade stories of stumbles and small wins, and the thread tying their journeys together is the one most owners avoid until it's too late. If you're building something meant to outlive you, the question isn't whether this conversation starts — it's whether you start it on your terms.

What the panel kept returning to

Every one of the four panelists left the family business around college with no intention of returning. Saunders earned an engineering degree planning to own a factory — today he runs what he calls "a factory of plants." Deppe left for accounting before deciding the farm was worth coming back to, and Walters picked up most of her operational knowledge by reading her dad's accounting books, because, as she put it, "my dad was not the best person when it came to training." None of them had formal horticulture backgrounds. They learned the business by absorption, by hiring good people into roles they trusted, and by staying close to the work. That's not a quirk of one industry — it's the same pattern that shows up wherever founders build from scratch and then hand off.

Where it falls apart — and how to unblock it

The most useful warnings came from the messy middle. Walters told the room her father was furious when he found out the family had hired outside consultants — so they solved it by letting him pick the firm. Saunders and his brothers brought in two consultants early, each of whom told them to start the conversation now rather than later, and they're still working with those advisors as they shape what the third and fourth generations will own. Deppe leaned on peer groups and retired mentors, eventually forming an advisory board from those relationships. The takeaway for you: the work isn't glamorous, it isn't linear, and almost every founder will resist it at first. Your job is to make the next step easier than the excuse.

What to put on your calendar this quarter

If you're an owner reading this, three moves I'd push for this month. First, name the person or team who will inherit real decision rights — not a title, but a budget and a seat at the table. Second, audit the wealth side in parallel with the operating transition: who controls what, where the illiquid assets sit, and whether the structure can actually move when you need it to. For owners with digital holdings on the balance sheet, getting institutional-grade custody lined up before a transition is non-negotiable — BitGo's new LINK service is one example of the plumbing worth evaluating now, not during a crisis. Third, schedule the awkward conversation with your successor and one outside advisor in the room. Ask yourself honestly: if something happened to you in the next twelve months, would the business actually continue to run?