Jacob DeHart

Early Career

Jacob began his professional career as the co-founder of skinnyCorp, a Chicago-based web design and development firm. While developing client work under skinnyCorp, Jacob and his partner launched what would become one of the internet's most influential creative communities—Threadless. 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.

This period also gave rise to a series of experimental projects, many of them with novel business models but released before their time, 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).

After bootstrapping Threadless with $1000 and growing it to a $50MM business, Jacob exited skinnyCorp/Threadless at the age of 27 to explore new paths. From 2008 to 2011, he worked independently on several ventures, including CulinaryCulture, a social platform for food lovers to share recipes, favorite spots, and events. He also joined the board of OMGPOP, a NYC-based online entertainment company that developed Flash games and was later acquired by Zynga for $200MM.

Cloud Services & Digital Products

In 2011, Jacob co-founded Picturelife, a cloud-based photo and video backup service built to provide users with a beautiful, intuitive experience for organizing and reliving their memories. After raising multiple rounds of venture capital and scaling the team, Picturelife was acquired by SmugMug, with its team eventually transitioning to Amazon to help develop Amazon Prime Photos. Jacob remained in Chicago to pursue independent ventures.

From 2015 to 2018, he launched Thrilled.com, a service tailored to YouTube and Twitch creators that provided custom branding, graphic design, and ecommerce storefronts. During this same period, he also co-created Pulpulp, a direct-to-consumer limited-edition print business focused on high-quality artwork.

Hospitality

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.

Digital Art & Blockchain

Between 2021 and 2025, Jacob turned his attention to digital art and blockchain. Partnering with artist Mike Mitchell, he co-created The Visitors, a generative digital art project comprising 10,001 unique pieces distributed via the Polygon blockchain. The project sold out in one week and grossed over $1.2MM.

Building on this success, Jacob co-founded 0x420.io, a digital art consultancy alongside Mitchell and Mitch Putnam. Together they led successful collaborations with artists including:

• Shepard Fairey (7,400-piece collection, $2.5MM)
• Michael Reeder (5,000 pieces, $1.5MM)
• Tristan Eaton (5,000 pieces, $1.5MM)
• Pussy Riot, Foodmasku, Russ Morland, and others

Collectively generating over $6MM in primary sales.