San Diego · 2006–
I build the technical organizations behind products that have to work.
I.
Jesse Forrest is a founder, operator, and engineer in San Diego. The work has always been the same, even when the industry changed: hire the people, choose the simple system, and stay long enough to see whether it actually held.
He built product and engineering at Upwards from a blank page through Series B, rebuilt an engineering organization at Tradesy, and before that shipped software in payments, clinical care, and defense. He now invests his own capital through Yesteryear Ventures and sits on the board of the company he co-founded.
II. Selected work
Founder
A private holding company. I invest my own capital in a small number of early-stage companies and advise founders on architecture, hiring, and the version of the product that has to ship.
Co-founder, CTO, & Board Member
Co-founded the care platform. Built product and engineering from zero through Series B ($40M+ raised). Employer and government partnerships, including U.S. Army Reserve childcare access; provider tools so home caregivers can run a real business.
Director of Engineering
Every product should have five lives instead of one. I rebuilt the engineering organization through a period of rapid growth at a fashion resale marketplace whose thesis was sustainable consumption — making resale as simple, safe, and stylish as retail. Later acquired by Vestiaire Collective.
Co-founder
The first long company: a marketplace and operations platform for sports and recreation. Event coordinators could list leagues, teams, clubs, classes, and games, then promote, manage, and take payment. Players used it to find what was happening nearby. Nine years of building from scratch, overlapping the later roles on purpose.
Technical Lead
Evidence-based clinical decision support: SaaS that put current order sets and care plans in front of doctors and clinicians at the point of care, so the guidance they used was current and the care they delivered was more consistent. A shorter chapter, and a through-line: products that have to work for people, not just for a dashboard.
III. Now
Founder · Operating
Patient capital and hands-on building. I write a small number of checks with my own money, and I stay close to the technical and organizational problems I have spent a career solving.
Co-founder & Board Member
I stepped out of the operating chair at the end of 2025. The company remains the longest build of my career. I stay as a co-founder and director.
IV. How I work
Tools matter. People matter more. The engineering organization has to care about product, culture, and the customer who never sees a pull request.
Understand the business objective first. Then pick the reliable thing. Complexity is easy to defend and expensive to live with.
Eight years at Upwards. Nine at FindSportsNow. The interesting work starts after the launch, when the product has to keep working for real families, real inventory, real money.
An investment is not an operating role. A board seat is not a day job. Plain speech keeps everyone honest, including me.
Contact
Founders, operators, and people I have worked with are welcome. A few lines about what you are building — or why you wrote — is the right place to start.
