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The 3 Game-Changing Truths I Discovered Too Late That Could’ve Saved My Startup—and Your Sanity—20 Years Ago

The 3 Game-Changing Truths I Discovered Too Late That Could’ve Saved My Startup—and Your Sanity—20 Years Ago

If I could sit down with a new B2B founder today, these are the three conversations I’d make sure we had — the same ones I wish someone had with me early on.

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1. Don’t give it all away

Early on, most founders pay their first hires in equity. Each grant solves an immediate payroll problem but also sets the “going rate” for everyone who follows and nibbles away at the founder’s ownership. Over time, as more hires come on board expecting similar equity deals, the option pool expands, and suddenly, there’s not enough left to offer meaningful stakes to the senior leaders who matter most for the company’s next phase of growth.

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