Building durable wealth without trading away health, family, or life.

Speaking topics & sample questions

Six angles, each with a sample question for your pre-call doc.

1. 01

   Strategic tax planning for founders past $1M

   Why most high-earning founders are still running a reactive April tax process — and the year-round moves that actually shift effective rates.

   Sample question

   “You write that most founders don’t have a tax problem, they have a tax-planning problem. What do you mean by that, and what does the gap usually look like in dollars?”

2. 02

   Health first, wealth next

   Why the fittest founders tend to build the most durable businesses — and what breaks when a founder treats their own body as infrastructure debt.

   Sample question

   “You’ve written that the fittest founders build the most durable businesses. Where does that conviction come from, and what do you actually see fall apart first when a founder neglects their body?”

3. 03

   The scaling game: recurring vs. project income

   Why project-based service businesses ceiling out — and the mindset and structural shifts that move owners into recurring revenue.

   Sample question

   “You’ve written that project-based service businesses ceiling out without the founder seeing it. How does that ceiling actually show up in the P&L, and what’s the structural shift into recurring revenue?”

4. 04

   Mental health as a founder’s compounding asset

   How unexamined psychology quietly caps revenue — and the practices high performers keep hidden because they sound soft.

   Sample question

   “You’ve called mental health a founder’s "secret to wealth." For someone hearing that for the first time and rolling their eyes, how would you make the case?”

5. 05

   Midlife reinvention for business owners

   Career pivots, identity restructuring, and goal-setting that actually changes outcomes — for founders who suspect their 40s are the real game.

   Sample question

   “A lot of your readers are in their 40s and quietly wondering if it’s too late to reinvent. What do you tell them?”

6. 06

   Building a business your family wants to be part of

   Entity structure, estate planning, and generational wealth framed as family-design rather than tax accounting.

   Sample question

   “When you say "build a business your family wants to be part of" — what does that look like operationally for a founder making $400K+?”

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