Jacob DeHart

a multidisciplinary entrepreneur whose career spans over two decades of building innovative, community-driven ventures across ecommerce, art, and hospitality.

Career Timeline

2020 — Present

In 2021, Jacob turned his attention to digital art and blockchain technology. His first project was a partnership with artist Mike Mitchell. Together they created The Visitors, a 10,001 piece generative digital art collection. The project sold out in one week, generating over $1.3 million in primary sales.

Building on this success, Jacob co-founded 0x420, a digital art consultancy with Mike Mitchell, and Mitch Putnam. Together they led successful collaborations handling art production, marketing, and distribution with artists such as Shepard Fairey, Tristan Eaton, Michael Reeder, Pussy Riot, Foodmasku, Russ Morland, and others. Collectively, their projects generated over $7 million in primary sales.

In 2023, Jacob collaborated with artist James Paterson (Presstube), musician Stephen Ramsay (Young Galaxy), and technologist Greg Sadetsky (GREG) to create KRILLER, a seven day, eternally looping, globally synced broadcast of synth-soaked ambient software art. A total of 6,300 ambient audio tracks were created and paired with dynamic visuals. Each track when played together creates a 7 day looping concert.

2010 — 2020

In 2010, Jacob joined the board of OMGPOP, a NYC-based gaming company founded by his friend Charles Forman, which was later acquired by Zynga for $200 million.

In 2011, Jacob and Charles co-founded Picturelife, a cloud-based photo and video backup service designed to provide users with a beautiful, intuitive way for organizing and reliving their memories. After raising multiple rounds of venture capital and building a world class team, Picturelife was acquired by SmugMug, with its team transitioning to Amazon to create Amazon Prime Photos.

In 2015 he created Thrilled.com, a service tailored to YouTube and Twitch creators that offered custom branding, graphic design, and ecommerce storefronts. Around the same period, he also co-created Pulpulp, a direct-to-consumer limited-edition print business focused on high-quality artwork.

In 2016, Jacob and his wife opened The Heritage, a 56-seat farm-to-table restaurant just outside of Chicago. They personally led the restaurant‘s interior design and culinary vision. The restaurant quickly gained acclaim, including a spot on the Chicago Tribune‘s list of the top 50 restaurants in the city by food critic Phil Vettel.

2000 — 2010

Jacob began his professional career as the co-founder of Threadless, which would become one of the internet‘s most influential creative communities. The site pioneered crowdsourced ecommerce by inviting users to submit and vote on T-shirt designs, creating a new model for participatory commerce that grew into a global phenomenon.

Threadless existed as part of skinnyCorp, a Chicago-based web design and development firm. After experiencing the explosive growth of Threadless, Jacob and his partner decided to focus on Threadless and other internal projects moving forward.

The early to mid 2000‘s offered opportunities to experiment with what would come to be known as Web 2.0. Over the course of this period a series of projects were launched including Extratasty (a crowdsourced cocktail recipe site), 15megsoffame (an early music-sharing platform), OMGClothing (user-submitted slogans turned into T-shirts), IParkLikeAnIdiot (a novelty bumper sticker ecommerce product), and NeedsHelp (a crowdfunding platform).

Threadless was a bootstrapped business, started with just a $1,000 investment from it‘s founders. In 2005, Jacob and his cofounder took investment from a VC firm at a $50 million valuation. In 2008, Jacob left skinnyCorp/Threadless at the age of 27 to explore new opportunities.

Recognition & Speaking

Jacob and his work has been recognized by Crain‘s Chicago Business (“40 Under 40”) and featured in a Harvard Business School case study. In 2008, Inc Magazine named Threadless.com “The Most Innovative Small Company in America.”

He has taught at the School of the Art Institute of Chicago and spoken at institutions including MIT Sloan School of Management, UCLA, Parsons School of Design, Columbia College, DePaul, and Dominican University. His speaking engagements include SXSW (Austin, TX), O‘Reilly Emerging Technology Conference (San Diego, CA), Customer Made (Copenhagen, Denmark), and Semi-Permanent (Lincoln Center, NYC). He has been interviewed by Anderson Cooper 360, National Public Radio (NPR), and other national media outlets.