Oct 1, 2026
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4 min read
Brian Lamb explains how buying your shares, structuring a sale, and transferring equity to a trust can affect your tax bill, and your control over the proceeds.
Sep 29, 2026
3 min read
Why your first million might not change your daily life, and how pricing the life you actually want gives you a clearer financial target.
Sep 23, 2026
Why a winning startup investment can still leave you waiting for cash, plus the spending habits that can outlive the reasons you started saving.
Sep 21, 2026
Why the same $250k investment can make perfect sense for one person and be a huge mistake for someone else.
Sep 16, 2026
Why a founder’s exit can turn an owner into a lender, plus the investing blind spot that can survive a successful business sale.
Sep 11, 2026
2 min read
Why I use cash flow to fund a longer-term bet, and why more deals don’t always mean more diversification.
Sep 10, 2026
Why a $100M franchise system is not $100M of franchisor revenue, plus the recurring service opportunity that can remain after a restaurant closes.
Sep 4, 2026
Why a $100M portfolio can still feel empty, plus the simplicity premium hiding beneath the polished complexity of alternative investments.
Aug 27, 2026
5 min read
Why $500K of income can become a trap, plus the ownership math that changes a 20-year career.
Aug 20, 2026
Why a $10M exit can trigger a bad allocation, plus the illiquidity premium Jeremy Roll refuses to waive.
Aug 14, 2026
6 min read
Why a $500 million paper fortune wasn't real liquidity, plus the venture math that can tolerate 80% zeros while waiting for a 100x outlier.
Aug 12, 2026
Almost every private investment you've been shown puts you in the same position.
Aug 5, 2026
70% of people haven't talked to a living soul about money in a year, plus the $20 experiment that still works even when you force people into it.
Aug 1, 2026
A $30,000 Christmas week that cost nothing out of pocket, and why chasing airline status is mostly a waste of your time.
Jul 22, 2026
The $44M founder who won't take a vacation, and why the hardest part of an exit has nothing to do with the deal.
Jul 16, 2026
The tax strategies behind eight and nine-figure exits, and what a decade of 27% IRRs going to zero taught him.
Jul 14, 2026
A founder who built an eight-figure company around the life he wanted, and a fund manager who moved to Costa Rica with three kids and runs her whole business from a laptop.
Jul 3, 2026
What 8,000 HNW investors actually buy, plus a live panel on where they're putting capital now.
Jul 1, 2026
Issue #25 - Two quick wins from the platform this quarter, and one new development behind them.
Jun 22, 2026
Issue #24 - Anyone with a spreadsheet and some capital can buy a business. The hard part is everything that comes after, and almost none of it lives in the numbers you underwrote.
Jun 16, 2026
Issue #23
