Give First Week: The Long Game, How Trust & Will Built a Category from Scratch

Eight years ago, Trust & Will (Techstars 2018) was three friends in their late twenties, a shared discomfort talking about wills with their families, and a hunch that estate planning deserved its own TurboTax. At Give First Week, co-founder and CEO Cody Barbo sat down with Ryan Kuder, Techstars MD Emeritus and his MD from the Techstars Anywhere class of 2018, to trace how that hunch became the largest online estate planning company in the U.S.: 83 million raised, 100 employees, 1.3 million families served, and more than 135 million in cumulative revenue.

The early days were slow by design. Barbo and his co-founders started by messaging everyone they knew who was married, had kids, or owned a home, building a 1,000-person waitlist almost entirely from direct outreach before their beta even launched. Growth came from getting the basics right before chasing scale: better customer support than the market leader, five-star reviews even when something broke, and small, consistent marketing tests with micro-influencers. It took until August 2019 to hit a $1 million run rate, a milestone Barbo still remembers standing in the office for.

The unit economics were backwards for a long stretch, and cash got tight enough that the team was down to about two months of runway heading into their Series A. What got them through, Barbo said, was a clear distribution narrative: partnerships with financial advisors, banks, and insurers to diversify beyond direct-to-consumer. That story, plus a tightly run process, closed the round with three term sheets in four weeks.

Growth accelerated hard during COVID, when the business went from roughly $800,000 to $2.6 million in under a year, largely on the back of organic search work the team had invested in a year earlier. A later round that looked dead, an investor passed on their Series A after flying them out to say no in person, came back around nine months later as a full-circle Series B, oversubscribed within days.

Barbo credits the compounding relationships built over nearly a decade, including a co-founder partnership with Daniel that's held steady on equal pay and equal equity since day one. But the piece he returned to most was personal discipline: protecting the first hour after waking and the last hour before bed, a consistent 5 a.m. routine, and being fully present for his kids before switching entirely into founder mode. "You got to take care of yourself first," he told the audience, before the business.

Trust & Will also became a certified B Corp, a multi-year process Barbo says was worth it for the team members and customers who choose the company because of its mission, not just its product.