01 An entrepreneur can build something great and lose themselves inside it. Seven or ten years from now, when CKO and EnrolledAgent.com belong to someone else, who in your life will be able to say, with certainty, that this did not happen to you?
02 Every founder eventually faces a trade between growth and something they hold sacred. What are the top things you would refuse to compromise, even if refusing them cost you incredible success?
03 Set aside the financial outcome for a moment. What is the version of success, measured in life rather than dollars, that would make all of this worth it? And what is the version that, even if quieter than you imagined, you would feel content with?
CKO today
The present shape of CKO.
04 Who are the people you have built around you, and how is the team structured today (partners, senior staff, support, contractors)?
05 Which services carry the most revenue, and which carry the most margin?
06 Where is CKO running stronger than someone outside the firm would assume?
07 Every endeavor is held back by something. Looking honestly at the next twenty-four months, what is the single most consequential constraint, system gap, or hire that, once resolved, would unlock the most ground?
Platform history
The arc of EnrolledAgent.com.
08 Few things teach a founder more than a venture that did not unfold as hoped. What did you believe about Enrolled Agents and the market when you first built EnrolledAgent.com that you no longer believe now, and what have the years since taught you about what this market will and will not pay for?
09 What was the season of your life and your other businesses when EnrolledAgent.com moved into the background?
Market wedge
The top three.
10 Of CKO's current book of business and the existing user base on EnrolledAgent.com, which three client types or verticals show the strongest signal that EnrolledAgent.com could serve them well right now?
11 Of those three, which is the one EnrolledAgent.com should focus on first, and why?
12 What would make those clients choose EnrolledAgent.com over what they have access to today?
13 Not every buyer is the right home for what you have built. Of the companies positioned to acquire something like EnrolledAgent.com one day (Intuit, H&R Block, Wolters Kluwer, Thomson Reuters, Drake, the PE roll-ups), which would you most want EnrolledAgent.com to land inside of, and which would feel like a loss even at the right price?
14 Markets reward those who see what others miss. Reading the EA and tax-tech landscape today, what do you believe about where this market is headed in the next five to seven years that the conventional view is missing?
15 AI is one of the most consequential pieces of leverage available to firms like yours right now. Where is it already showing up inside CKO and EnrolledAgent.com today, formally or informally, and where in your judgment should the line sit between AI as a tool your team uses to grow the firm, AI as a feature clients see and pay for, and AI as something you would never put between you and a client?
16 Founders do not break from one bad day or one bad week. Small invisible cracks build up over time and do them in. What does a sustainable rhythm look like in your life, and which hours must remain untouched, even when the work asks for more?
17 As we prepare to begin this journey, what would you most want to know about who I am, how I work, and the philosophy that grounds it?
An initial read
The horizon.
Before our call, I had no idea Enrolled Agents existed as a credential, much less as a profession. Since then I have gone deep. What follows is an initial read on EnrolledAgent.com, since that is where the acquirer conversation sits. There is more to share, and the deeper work belongs in Discovery and in person, when we have the chance to sit down. For now, here is enough for you to see how I am thinking about your business.
The first thing that surprised me in the data was how big the active EA community actually is. The IRS reports more than 60,000 credentialed Enrolled Agents in its current statistics, with even more on its full active roster.[1] My read is that EnrolledAgent.com is sitting on top of a real national supply of licensed professionals, and no other platform has organized that supply at scale. That is rare, and it matters.
What this kind of asset costs, when it is built well, is no longer abstract. In January 2025, Thomson Reuters paid $600 million in cash for SafeSend, a tax workflow business with about $60 million in expected 2025 revenue.[2] In July 2024, Wolters Kluwer paid €325 million for a European cloud accountancy portfolio with €34 million in 2023 revenue.[3] Those are not the prices buyers pay for directories. Those are the prices buyers pay when three things are true:
The platform is software the professionals actually use as part of their daily work, not a website they visit occasionally.
The platform comes with a list of verified, licensed people the buyer would otherwise have to spend years recruiting and credentialing on their own.
The platform brings in steady recurring revenue, meaning customers pay every month or every year rather than once.
The pattern is consistent. The buyers are paying for the network of professionals and the daily-use software that runs on top of it.
The companies you would expect to be in that conversation are already saying so publicly. Intuit's 2024 Investor Day described its strategy as combining AI with networks of credentialed experts. H&R Block partnered with OpenAI in April 2025 to bring AI capabilities into its tax-professional network. Thomson Reuters has named AI investment a stated strategic priority and has been acquiring tax workflow businesses on a regular cadence.[4] None of this is hidden. The buyers have told the market what they want.
Where the lasting advantage actually comes from, in my read, is not the AI itself. AI is the engine. The lasting advantage comes from the things that are hard for a competitor to copy, even years later. The credible analysts looking at how these kinds of platforms are valued through 2026 keep returning to the same three factors. The first is information that took years to gather and that a competitor cannot quickly recreate. The second is a network of professionals that would take a buyer years to recruit and verify. The third is trust earned inside a regulated profession, where reputation cannot be bought overnight.[5] An EnrolledAgent.com that captures verified EA supply, structured engagement data, and compliance-safe consumer demand has a real chance to build all three. An EnrolledAgent.com that does not is a directory, and directories are not what these acquirers are paying for.
The path from where EnrolledAgent.com is today to where it could sit inside that conversation is the sum of every meaningful decision in CKO and EnrolledAgent.com between now and then. How the platform is bootstrapped or funded, what gets built first, how it stays on the right side of IRS and state regulations as it grows, and who is in the room when buyers eventually come to the table.
What I am hoping for in this work is the chance to come alongside you as a partner. To pray, plan, and prepare for how to build EnrolledAgent.com into something the biggest players in this market would pay top dollar to acquire, and to walk through those years in true success without compromising your character, your values, your relationships, or your soul. The first half is hard. The second half is harder. Both are possible by the grace of God. That is the work I would be honored to do with you.
Send my answers to Georges
Sources
[1] Internal Revenue Service, Return Preparer Office Federal Tax Return Preparer Statistics , data current March 1, 2026.
[2] Thomson Reuters, Thomson Reuters Acquires SafeSend, Expanding Tax Automation Capabilities , press release, January 2, 2025.
[3] Wolters Kluwer, Wolters Kluwer acquires European cloud accountancy portfolio , press release, July 29, 2024.
[4] Intuit, Intuit unveils new AI-driven expert platform experiences at Investor Day 2024 , September 26, 2024; H&R Block, H&R Block and OpenAI announce joint initiative , April 15, 2025; Reuters, Thomson Reuters beats revenue forecasts, raises AI investment , November 5, 2024.
[5] Solomon Partners, The Information Services Selloff: Why the Market Is Missing the Moat , February 12, 2026; Mawer Investment Management, Data Moats in the Age of AI: What Still Matters? , February 25, 2026; Morningstar, Intuit's Switching Costs Support a Wide Economic Moat , May 23, 2024.
