Founders, SAFEs, and the Real Cost of “Easy Money”: Inside Startup Boston Week’s Equity Clarity Session

Equity decisions made in a startup’s earliest days can echo for years, often in ways founders don’t fully see until it’s too late. That reality was front and center at The Founder’s Guide to Equity Clarity: SAFEs, Term Sheets, and the Road to a Clean Cap Table, a packed session at Startup Boston Week presented by the team at Peak Corporate Counsel, including Bob Baker and Matt Shrimpton.

The full event video is embedded below if you’d like to watch the conversation start-to-finish, or keep reading for an overview.

The session pulled back the curtain on how seemingly straightforward fundraising tools, particularly SAFEs, can quietly reshape ownership, control, and leverage once a company reaches a priced round.

Why “Later” Is Often Too Late

From the start, the speakers emphasized a pattern they see repeatedly in early-stage companies: founders treat SAFEs as temporary, low-friction capital, only to confront their real cost during a seed or Series A raise.

“Most founders don’t worry about SAFEs when they issue them,” Baker explained. “They worry about them when they convert.”

That moment when all SAFEs convert at once, an option pool is resized, and new investors come in is often the first time founders see the true dilution they’ve accumulated. By then, the decisions are locked in.

The Founder–VC Relationship Is a Long Game

Rather than framing venture capital as adversarial, the session focused on alignment and misalignment between founders and investors. VCs are managing portfolios, timelines, and returns for limited partners. Founders are building companies they live with every day.

Those incentives overlap, but not perfectly.

That’s why term sheets, even at just two to five pages long, matter far more than many first-time founders expect. “This is step zero,” the presenters noted. “What you agree to here ripples through every future round.”

A Tale of Two Term Sheets

To make the risks concrete, the Peak Corporate Counsel team walked through a fictional startup scenario, modeling two different term sheets for the same company.

In one version, broad “inclusive” language around valuation and SAFEs resulted in outsized dilution for the founding team. In the alternative, more founder-friendly structure, small changes in wording led to meaningful differences in post-round ownership.

The takeaway wasn’t that one approach was universally right, but that precision matters. Even a one- or two-point swing in ownership at seed can compound dramatically over time.

SAFEs: Simple, Popular and Often Misunderstood

SAFEs remain the dominant early-stage fundraising instrument, largely because of their speed and simplicity. But the session cautioned against treating them as consequence-free.

Valuation caps, discounts, and conversion mechanics all interact in ways that aren’t always intuitive. A low cap that feels generous to an early investor can become painfully dilutive if a company’s traction accelerates.

“Raising on SAFEs is still raising a round,” Baker said. “You just don’t see the dilution yet.”

A Shifting Early-Stage Landscape

During the Q&A, speakers noted a subtle but important shift in early-stage funding. While institutional VC remains cautious, more angel investors and family offices are stepping in, often with greater flexibility and fewer governance demands.

For founders, that can mean friendlier terms and delayed board pressure but only if they understand what they’re agreeing to.

The Bottom Line: Know Before You Sign

The session closed with a clear message: clean cap tables aren’t accidental. They’re the result of intentional decisions, early modeling, and honest conversations with counsel before a term sheet is signed.

Founders don’t need to become lawyers, but they do need to slow down long enough to understand how today’s “easy” capital shapes tomorrow’s leverage.

As Startup Boston Week continues to spotlight the realities of building in today’s market, this session served as a reminder that clarity (not speed) is often the most founder-friendly move of all.

The full event video is embedded above (or you can watch it directly on YouTube) to catch the complete Q&A and founder stories shared from the stage.