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Jason Okra

InvestorFounder

CEO at Wayline · Founder at Cribspot

San Francisco, California, United States

FoundedCribspot · YCWayline · YC

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About

Jason led WeWork's All-Access commercial business and WeLive coliving product, served as head of software development at hospitality provider Jupe, and previously founded and bootstrapped Baker Street property management company and Cribspot, a multifamily property-technology startup that was acquired by ApartmentList in 2018.

CEO at WaylineYC S25

Intro paths

YC

Jason went through Y Combinator (Summer 2025) — any YC alum in your network can reach them through the YC community.

GP

Their group partner at YC was Gustaf Alstromer, General Partner at Y Combinator — the partner who ran Wayline's batch and knows the company first-hand. YC profile ↗

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In turn, Jason can intro founders to Wayline's investors below.

Wayline's investors · 12

Aliaksandr HudzilinBatch VenturesBlast.Club$5.5M checksGreat Wave VenturesNew York · $250K – $1M checksJames Beshara FundVeniceMoonfire VenturesLondonPeterson Venture PartnersSalt Lake City · $5M – $25M checksPioneerToronto, OntarioRebel FundSan Francisco · $100K – $5M checksValia VenturesLondon · $50K – $50M checksY CombinatorSan Francisco · $500K checks · since 2025Zeno VenturesGeneva

Co-founders at Wayline

EREric Rowell
Eric RowellCTO
JO
Jason Okra Eric RowellFounder

Founder at CribspotYC W15

Intro paths

YC

Jason went through Y Combinator (Winter 2015) — any YC alum in your network can reach them through the YC community.

→

In turn, Jason can intro founders to Cribspot's investors below.

Cribspot's investors · 7

Grand VenturesGrand Rapids · $250K – $2M checksGreeTokyoHyde Park Venture PartnersChicago · $500K – $3M checksInvest DetroitDetroitService Provider CapitalVailVenture Investment AssociatesPeapackY CombinatorSan Francisco · $500K checks · since 2015

Co-founders at Cribspot

EDEvan Dancer
Evan DancerCTO/Lead Engineer - Javascript (Ember), Ruby (Rails), React Native
TJTim Jones
Tim JonesCTO
JOJason Okrasinski
Jason OkrasinskiExecutive Officer, Director

Investments

Investor

Motives

Per curated public sources.

Frequently asked questions

Who is Jason Okra?
Jason led WeWork's All-Access commercial business and WeLive coliving product, served as head of software development at hospitality provider Jupe, and previously founded and bootstrapped Baker Street property management company and Cribspot, a multifamily property-technology startup that was acquired by ApartmentList in 2018.
Where does Jason Okra work?
Jason Okra is Founder of Cribspot and CEO at Wayline.
What companies did Jason Okra found?
Jason Okra founded Cribspot, Wayline.
What companies has Jason Okra invested in?
Investments tracked here include Motives.

Founder mafias

About this profile. Compiled from public sources — Wayline's own website and public professional profiles — and summarised by Fundraising Fox; every fact is kept with where it came from. Spotted an error, or would rather not be listed? Email privacy@fundraisingfox.com · How we build profiles · Your rights