Early checks for founders solving real, unglamorous problems.
We invest our own capital at pre-seed and seed, and we show up after the wire clears: architecture, hiring, diligence, the hard first version. Our current portfolio starts with Cindera.
Yesteryear Ventures, Inc. · San Diego, California
Patient capital.
Hands-on building.
Yesteryear Ventures is a private holding company. We invest our own capital in early-stage technology companies, help build them with two decades of operating experience, and hold what we believe in for a long time.
What we do
Three ways we put capital and experience to work.
Yesteryear was built the old-fashioned way: by doing the work first and investing in what we learned. The three lines below are how the company earns, compounds, and endures.
A small number of engagements a year where a technical operator changes the outcome.
Fractional CTO seats, technical diligence for investors and acquirers, and short, intense builds. It is how Yesteryear began, and how we came to know several of the founders we back.
Over time, long-duration assets alongside our companies.
Yesteryear is structured to hold what we never want to sell — land, property, and the rare business that earns a permanent place. This is a direction we are building toward, and we say so plainly.
Looking ahead
Founder track record
Twenty years of building things that had to work.
Before Yesteryear wrote a check, its founder spent two decades shipping software — at a defense contractor, a payments startup acquired by American Express, a fashion marketplace, and a care platform he co-founded and still leads as CTO.
20+years building software and engineering teams
3companies co-founded, including Upwards
$240M+raised by companies he has helped build and lead
2acquisitions across companies he helped build
Figures describe the career of our founder, Jesse Forrest, across companies he co-founded or held senior engineering roles in. They are not a description of Yesteryear's portfolio.
Portfolio spotlight
Cindera: a living wildfire-readiness score for every home.
Cindera gives homeowners one clear number for how ready their property is, a short prioritized plan to raise it, and proof that satisfies insurers and grant programs. Cities, fire departments, HOAs, and insurers use it to keep neighborhoods protected and insurable. It sits squarely in a thesis we care about: resilience, property, and the systems that decide what gets insured.
CinderaAngel investment · Climate resilience & property
Illustrative. Visit Cindera for a real score.
Where we spend our attention
We invest where we have scar tissue.
Every sector below is one where our founder has shipped product, hired teams, or lived with the consequences. That is the only edge an angel honestly has.
The care economy
Child care, elder care, and the employers and public agencies that pay for it. The market is enormous, underbuilt, and run on goodwill. We know it from the inside.
Resilience, property, and insurance
Homes, land, and the systems that decide what is insurable. Climate is rewriting those rules; the software that keeps up will matter for decades.
Marketplaces with real supply
Two-sided businesses where the hard part is trust and logistics, not growth hacking. Our founder helped scale one of the largest fashion resale marketplaces in the United States.
Payments and financial plumbing
Boring, essential infrastructure. We have built virtual-currency platforms, payment flows, and the reconciliation nobody wants to think about.
Vertical software for serious operators
Tools for people who run physical businesses — care providers, trades, operators — where software is a means, not the point.
“The best companies I've been part of were built on things that aren't new at all: patience, craftsmanship, and doing what you said you'd do. We named the firm after the part of the past worth keeping.”Jesse Forrest, Founder & Managing Partner
The founder
Jesse Forrest is the co-founder and CTO of Upwards, the Los Angeles–based care platform that has raised more than $60 million and matches families with child care across the United States. Before that he was Director of Engineering at Tradesy and led engineering teams at American Express and Sometrics. He has co-founded three companies and seen two acquisitions.
Get in touch
Building something that should still matter in ten years?
We read every note. A few lines about what you're building, who it's for, and what's working is the right place to start.