About
A multidisciplinary entrepreneur whose career spans over two decades
of building innovative, community-driven ventures across ecommerce,
digital art, cloud services, and hospitality.
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:
Collectively generating over $6MM in primary sales.
Recognition & Speaking
Throughout his career, Jacob has taken on diverse roles including
CEO, CTO, full-stack developer, designer, and product strategist.
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.
Today, Jacob continues to advise startups, invest in new ideas, and
build products that sit at the intersection of creativity, technology,
and community.