As a kid, I watched Seahawks games in the Kingdome. Years later, I watched that same stadium implode from a rooftop—standing next to Eddie Vedder, coffee in one hand, cigarette in the other. Years later, I learned the Nordstrom family once owned the team—which came full circle when Dan Nordstrom seed-funded my first startup, Playmark, alongside George Aposporos, Amazon’s first VP of BD. George had the relationships, vision, and strategy. I had a product plan and the engineering team to execute. Together, we started with one paying customer and built a platform we could sell to every major sports league looking for a way to manage licensing rights and royalty payments.

In 2012, we launched the first online royalty platform for managing likeness rights in commercial products—starting with all 1,800 NFL players across all 32 teams.

The Playmark platform transformed how the NFL Players Association licensed digital likenesses to brands like EA and Topps. We automated royalty collection and payment, putting 8% of sales directly into players’ pockets—often amounting to 6-7 figures of additional annual income.

Licensing approval times dropped from six months to six weeks. One licensing manager could now do the work of ten. CFOs loved it.

But the efficiency that made Playmark powerful also threatened internal fiefdoms—slowing enterprise adoption and stalling sales. Distribution lesson learned. We sold the technology rights to the NFLPA and returned capital to investors. A clean, hard-earned exit.

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There should be a word like “adulting” for parenting your parents. When I stepped into that role, I tried to help mine set up a will, trust, and medical directives. I pointed them to online templates or suggested hiring an elder lawyer. My parents didn’t trust the forms—they felt confusing and worried they'd make a mistake. And my parents thought lawyers would be too expensive, which is one of many reasons they hadn't done it yet. So I did it all for them with some guidance from my attorney. That’s when I realized: preparing for the future was worth it for people with wealth, but broken for everyone else.

In 2016, a former colleague and I co-founded Tomorrow to make estate planning simple and accessible for the 99%—people who’d never hire a lawyer, never get around to it, and never want to leave a burden behind.

We built a network of 100+ attorneys across all 50 states to make it fully legal—then used illustrations, animation, and storytelling to make it fully human.

The Tomorrow app helped 1 million people plan for the future by making choices clear and leaving the document until the end—when all the decisions were done. Questions presented adapted programmatically to each family’s unique structure and local laws—no templates, no jargon. In under 10 minutes, you'd get an email with ready-to-sign PDFs that have held up in court.

It wasn’t just beautiful—it worked. Year-over-year growth hit 216%, and users left reviews like:

“Easy peasy. Makes doing adult things easy and fun. If this didn’t exist, I likely would not ever have a will.” – Stacie

In 2022, on our path to Series B, Tomorrow was acquired by digital insurer Ethos. The product is now fully integrated and drives higher LTV by offering estate plans alongside term-life policies. Click the link above to see it.