How to Seed Businesses While Still Playing Pro?

Why should I think about business now if I'm still playing?

Because the worst outcome is reaching the end of your career and thinking 'what do I do now?' The foundational principle here is never be reactive to retirement. Your career gives you income, access, and credibility that a normal entrepreneur would take decades to build — but only while you're active. If you wait until you retire to start learning how business works, you'll be learning at exactly the moment you need to be earning. That's the trap this framework is designed to prevent.

Won't starting a business distract from my performance?

It will if you start too many things too early. That's an explicit pitfall: beginning multiple ventures before mastering your primary craft creates distraction that harms both. The solution is the 'don't want to be learning when I want to be earning' principle — pick one or two deliberate learning investments, not to dominate them, but to understand how they work. A minority stake in a startup, a small hospitality business, or an equity position in an agency lets you learn without demanding your full attention.

What kind of businesses should I start with?

Start with learning investments, not empire-building. The point isn't to run these businesses — it's to understand how they work so the learning curve is behind you when you can commit full energy post-career. Consider which of the four pillars — Media, Agency, Investments, Foundation — you're most drawn to, and take a small, low-stakes position there. If you love content, invest in or observe a media operation. If you're fascinated by deals, take a minority stake and watch how negotiations run.

How do I evaluate the investments I do make?

Apply the Founder First Principle: before assessing the idea, market, or product, ask whether the founder can take the business ten levels. A great idea with a founder who can't scale is a losing investment — and emotional attachment to concepts is exactly how early capital gets lost. Then apply the cross-pollination test: does this business speak to anything you already own or your platform as an athlete? That connection is both your value-add and your leverage for a better deal.

How do I protect my earnings during this phase?

Build financial literacy as survival infrastructure, not optional. High earners lose wealth through the absence of literacy, not low income — and predators operate through trusted referral networks precisely because athletes assume social proof equals safety. Learn good debt versus bad debt, budgeting, and how to read a deal. Build structural gatekeeping: second and third opinions, full visibility of transactions before signing, and one or two objective advisers who aren't emotionally compromised.

What should my end goal be?

To arrive at retirement with experience, relationships, and options — not a portfolio of half-built distractions. If you seed deliberately during your earning years, transition becomes a switch from the 'preparation phase' to the 'all energy in' execution phase, where you already know how these businesses work. That's the difference between building an empire and scrambling to figure out what to do next.

Next step

Identify which single pillar you're most curious about, then find one small, deliberate learning investment in that space this year. Keep it minority and low-stakes. Your job is to observe how it works, build relationships, and put the learning curve behind you — all without compromising your performance on the field.