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Hi! I'm Okra πŸ‘‹Β  β€” Β I'm a...


Hey, I'm Jay! ⏎

I'm a builder and designer,

Storyteller and creator.


I've spent the last decade founding, operating, and building companies.

My Story

I grew up playing board games, camping outdoors, and building cool stuff like Lego cities, pinewood derby racers, and science fair projects. Here's a look at the experiences that have shaped me.

Hi! I'm an entrepreneur and generalist that's passionate about building products that make the world incrementally better.

New Jersey Born


I grew up in a red-brick, white-sided, suburban middle-class home in central New Jersey β€” right where the state's armpit meets New York. We called pizza a 'plain tomato pie' and used highway exit numbers to reference where we lived.



I spent afternoons and summers building Lego cities, trading Pokemon cards, playing board games (like Risk, Stratego, and Settlers of Catan), and battling friends head-to-head to RTSΒ video games (like Stronghold, Command & Conquer, and Starcraft).

Eagle Scout


I became a Boy Scout and Eagle Scout; Along the way, camping in remote places like Alaska, high adventure hiking along the Appalachian mountains, leading the troop during summer excursions, and managing service projects to rebuild local parks and churches.



I interned at @SeatGeek, a ticket booking marketplace, focusing on SEO and content β€” specifically music festivals generating tens of millions of visitors, annually.

University of Michigan


I attended the University of Michigan (@umich) and graduated with a Bachelors in Business Administration.

Digitas Rosetta


I worked at Rosetta Consulting Group, a subsidiary of Digitas Marketing Company, before leaving to start my own company. Although I only worked there for three months, I worked on two mini-projects with Blackberry to assess their customer segmentation and strategize how to revitalize their business.



Circa 2012, the rental search market was fragmented. The industry was demonstrably long-tailed, with mom-and-pop landlords still using hand-drawn 'For Rent' signs, faded from years of sun-exposure.

Frustrated, I worked with fellow UM wolverines β€” @Tim and @Evan β€” to simplify the problem. We started with a search engine to aggregate the rental listings from all the other listing sites β€” a renter's one stop shop for housing.

We eventually expanded to 100+ campuses, 'graduated' from Y-Combinator, and raised $2.5MM in funding. Yet, we struggled to find market-fit. The Occam razor is that startups are plain hard. Like Connect Four, startups require a long time to play out and you often lose with an unforced error. As Paul Graham, one of Y-Combinator's founding partners, wrote in an earlier essay:"don't die" β€” "be the cockroaches".

In 2018, our team found a soft-landing at @ApartmentList. In the end, over a six-year period, we helped 48,495 users find an apartment rental and housed 3,431 tenants in managed properties .

You can read more about our story here.



Baker Street Properties is a traditional real estate property management company that combines existing software with custom code and processes to automate the rental experience.

WeWork is a commercial real estate company providing beautiful, flexible shared workspace for distributed companies.

Jupe is an offgrid (electric) flat-packable dwelling manufacturer - think Tesla for mobile dwellings used for glamping, festivals, and shelter housing.
Webflow is a low code tool for visually building/designing online websites.

Wind in my Sails

I'm passionate about where we live, who we are and what we know (or, don't know).

ome, abode, dwelling, pad, crib, the roof over one's head; A home comes in many forms, but its meaning and significance is the same.

I've seen this issue up close over the last six years, as housing costs have outpaced income growth and gentrification has pushed people further away from city epicenters. Families, students, and professionals struggle to find affordable housing; later on, battle to avoid eviction -- the catalyst for endless poverty.


irtual reality and artificial intelligence are blending the line between real and imagined. This has the potential to disrupt industries β€” social media, news, history, real estate, etc. β€” in ways more damaging than many anticipate will come from autonomous vehicles

"The real danger if we hear enough lies, then we no longer recognize the truth at all" β€” Chernobyl, Craig Mazin


he Internet has made information more accessible than ever. However, it's becoming increasingly difficult to make sense of what's fact, important, and relevant. This paradox of choice has led to more noise and uncertainty.

I'm passionate about curating useful information, crowdsourcing local knowledge, and disseminating learnings β€” specifically, failures.


overty can be a trap β€” struggling to maintain Maslow's most basic hierarchy of needs like shelter and food. For the people that have fallen into it, or been brought up in this environment, it is an insurmountable hole to climb out of.

As technology continues to disrupt and consolidate wealth, it will be increasingly more important to figure out how to lift up disadvantaged communities, races, and countries.