Batch: Achievements
- Part of W14 Y Combinator batch, a major startup program
- Built Zesty from scratch, grew to $35M ARR and served thousands weekly
- Zesty acquired by Caviar/Square in 2018, a big exit
- Led product teams at DoorDash, focusing on gig economy solutions
- Currently heading Checkr Pay, streamlining payments and onboarding for gig workers
- Oxford Math grad, ranked in top ten, showing top-tier brains
Say hello to Chris Hollindale
Y’all gotta know about Chris Hollindale – this guy’s a straight-up tech and startup OG. He’s part of that W14 YC batch, so he’s been through the grind and knows how to build shit from scratch. The dude’s got a crazy solid background, starting from the UK where he crushed it in tech consulting for big finance firms like CHP Consulting. Then, he jumped into the startup world and threw himself into the deep end with Zesty in 2013.
Zesty was his baby – a corporate catering startup that made healthy, delicious meals from local spots, serving thousands weekly in the Bay Area. Under his leadership, Zesty hit $35 million ARR and became the real deal in the food tech scene. The kicker? They got acquired by Caviar/Square in 2018. That’s a big win, showing he knows how to build something that people actually want and that investors get hyped about.
But Chris isn’t just about building startups. After Zesty, he kept crushing it – jumping into roles at DoorDash, where he was a Product Manager and Group Product Manager. That’s where he really got into the hustle of gig economy stuff – building products that help gig workers and simplify their workflows. Now, he’s running Checkr Pay, making payments and onboarding smoother for gig workers – basically fixing the infrastructure behind the gig economy.
Got a startup idea and seeking investment? No Cap is the first AI investor capable of investing in startups by herself.
Talk to herWhat’s dope about him? It’s his whole process. Started in finance tech, then built something from nothing, sold it for a big win, and now he’s pushing the future of work and payments. It shows he’s got serious motivation – not just to make a quick buck but to actually solve real problems people face every day. The fact he studied math at Oxford and ranked in the top ten? That’s just proof he’s got the brains and discipline to back up his hustle.
Bottom line – Chris is that rare mix of tech nerd, business builder, and practical problem-solver. He’s not in it for the fame, just for the impact – changing how companies deliver food, how gig workers get paid, how startups grow. If you ask me, he’s the kind of founder who’s just getting started and will keep pushing till he’s changing the game in big ways. No Cap.
Select your comment type:
If something is wrong about Chris Hollindale, there's inaccurate information or there are updates, please let us know, we'll update it for you and everyone ;)