
If you're building a business without thinking about ownership structure, equity, and long-term strategy, you're taking on more risk than you realize. The way your company is set up from day one—your cap table, vesting terms, and legal structure—directly impacts your ability to raise capital, scale, and eventually exit. In my conversation with Bob Gillespie, we break down the financial decisions most founders either overlook or misunderstand, and how those choices can quietly erode enterprise value over time. Where Founders Lose Leverage Before They Even Scale What I see happen all the time is founders making early decisions that feel simple in the moment—but create major constraints later. Splitting equity without vesting, choosing an LLC when a C corporation would better support fundraising, or skipping key filings like an 83B election can all lead to misalignment, unnecessary taxes, and a cap table that investors won't touch. These aren't technicalities—they're structural decisions that determine who owns what, how dilution plays out, and whether your business is actually built for growth or just operating day-to-day. The Ownership and Capital Moves That Actually Matter If you're thinking about scaling, raising capital, or eventually selling your business, these are the areas you need to understand:<span class= "EOP SCXW5
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