Scaling With People Sell Without Regret with Joseph LoPresti
What if your biggest win isn’t the highest revenue month but the day you walk away on your terms? We go straight at the myths around exit timing, value creation, and “someday” planning with succession expert and wealth strategist Joseph LoPresti, breaking down the moves that turn a chaotic founder led operation into a transferable, high multiple business. From defining your Freedom Point to engineering enterprise value that a buyer will pay for, this conversation trades vague platitudes for clear steps any owner can start today.
We start by reframing success: income feeds your lifestyle, but enterprise value funds your freedom. Joseph explains how earlier planning widens your options, why three to five years is a sweet spot, and how to assess where you stand against best in class multiples in your industry. We dig into the buyer’s lens—recurring revenue, documented processes, leadership beyond the founder, competitive advantage you can articulate—and why “growing the bottom line” isn’t enough if growth depends on you. You’ll hear practical ways to reduce owner dependency, build predictable cash flow, and protect the value you’ve already created.
Then we tackle the money mechanics that too many founders leave to the last minute. Pre sale tax planning, entity structure, trusts, and capital gains mitigation need runway to work. Joel maps a two track approach: on the business side, assess, protect, enhance, and harvest value; on the personal side, model lifetime cash flow, set your Freedom Point, align investments, reduce taxes, and design your legacy with proper asset protection. We also unpack the power of coordinated advisors over siloed advice, and close with a personal action plan that clarifies ideal buyers, your post close role, and how your team will be treated during the transition.
Ready to sell without regret and live with intention after the deal? Press play, grab the free e book at exitbydesignbook.com, and tell us what metric you’ll fix first. If the show helped you think bigger about your exit, subscribe, share it with a founder friend, and leave a quick review so more builders can find these strategies.