Four startups, two states, one through-line: find the market everyone else stepped over.
Most days now Jordan Birnholtz is in the business of doubt. At Trarian, the company he co-founded with Michael Ulin, the job is to look at a patent and ask the question its owner least wants asked: what if it isn't valid?
Trarian underwrites what Birnholtz calls the trillion-dollar patent asset class, starting with the risk that a patent could be knocked out. The pitch is speed and certainty: feed in a patent, get back an analysis of how likely it is to be invalidated, how an opponent would do it, and which pieces of prior art would carry the argument - in days, not weeks. It is diligence as a product, aimed at a market that has mostly run on gut and billable hours.
By day he practices the live version of that same problem. Birnholtz is an intellectual-property litigation associate in the Chicago office of Kirkland & Ellis, one of the largest law firms on earth. Patents are no longer an abstraction to underwrite; they are the things he argues over in front of judges. The two roles feed each other. The litigator sees which arguments actually land. The founder builds the tool that finds them faster.
He got here on purpose. After roughly a decade of building companies, Birnholtz enrolled at Northwestern Pritzker School of Law and graduated cum laude in 2025. Along the way he interned at Paxton AI, a legal-AI startup, and co-authored a Journal of Criminal Law & Criminology study on true threats and free speech. The founder learned to read the rulebook. Then he started using it.
What stays constant across the resume is the instinct. Birnholtz keeps finding the overlooked seam - the underbanked customer, the cash-only NFT buyer, the unpriced patent risk - and builds something that fits it.
IP litigation is an odd landing spot for someone who spent years optimizing signup funnels, and that is precisely why it suits him. Patent fights are part technical argument, part storytelling, part raw economics - the value of a portfolio swings on how a single claim is read. A founder who has spent a decade learning what makes people act, and an information-science graduate who has spent that same decade thinking about how data moves, turns out to be unusually well cast for the work. The courtroom is just another market with its own incentives to decode.
In 2014, Birnholtz and two co-founders looked at the American pawnshop and saw a marketplace hiding in plain sight.
PawnGuru let people photograph what they wanted to pawn and collect competing offers from shops nearby, instead of walking item-in-hand from counter to counter hoping for a fair number. The customer was the one the rest of fintech ignored: the roughly 30 million underbanked Americans who run on cash and short-term loans. The company grew to more than 1.5 million consumers and worked with hundreds of pawn shops. Birnholtz ran growth and operations, holding the COO and CMO titles through 2020.
Then the through-line bent toward politics. He co-founded The Tuesday Company, whose Team app turned a campaign's supporters into organizers - relational organizing built for a phone screen. In 2018 it was used by more than 100 Democratic campaigns and progressive organizations. The product was civic; the skill was the same one he had sharpened at PawnGuru, which is getting large numbers of people to do something on their phones.
He also kept a foot in venture and finance, co-founding Bitbox Ventures and Midtown and making an angel investment in Portal Spaces in 2019. None of it was a straight line. All of it was the same person, looking for the next underpriced thing.
The PawnGuru thesis is worth sitting with, because it explains the rest. Banks treat the cash-only customer as a rounding error; payday lenders treat them as prey. PawnGuru treated them as a market that simply lacked liquidity and information. Give a borrower competing offers and a phone, and a transaction that once depended on whoever happened to run the nearest shop becomes something closer to a fair auction. That is a deeply unglamorous insight, and it scaled to seven figures of users precisely because nobody fashionable wanted to chase it.
The Tuesday Company applied the same logic to a different shortage. Campaigns have armies of willing supporters and almost no infrastructure to turn that willingness into action. Team treated relationships as the scarce resource and built software to mobilize them - the friend-asking-a-friend that actually moves votes. Different cause, identical move: find the thing people undervalue, then make it liquid.
An online marketplace that brought competitive bidding to pawn transactions, serving the underbanked at scale. Co-founder, COO and CMO.
Maker of the Team app for relational organizing, used by 100+ Democratic campaigns and progressive groups. Co-founder and chief product officer.
A Solana-based NFT marketplace where Birnholtz ran marketing. The team later pivoted the brand to Bash.gg.
As co-founder and CMO of Neon, Birnholtz helped put the world's first NFT vending machine on a New York City sidewalk in the Financial District. You walked up, tapped a credit or debit card, and walked away with a box holding a code for a digital collectible. No wallet, no seed phrase, no crypto required.
The idea, by the company's own telling, started over a team lunch. The machine made the abstract suddenly physical - a piece of internet money you could buy the way you buy a soda. It was equal parts product and performance art, which was rather the point of that whole era.
His partner on the deployment was Kyle Zappitell, a former Xbox mobile gaming engineer. Birnholtz brought the growth playbook; Zappitell brought the build.
Co-founded with Jonathan Polter and Jessica Zahnd to remake pawn transactions as an online marketplace.
Serves as COO and CMO, growing PawnGuru past 1.5 million consumers and hundreds of shops.
Co-founds the maker of Team, used by 100+ Democratic campaigns and progressive organizations.
Backs Portal Spaces as an angel investor.
Co-founds and markets a Solana NFT marketplace; launches the world's first NFT vending machine in NYC.
Works at a legal-AI startup while in law school - the bridge from founder to lawyer.
Graduates cum laude from Northwestern, joins Kirkland & Ellis as an IP litigator, and co-founds Trarian.
The bridge from startups to the bar was not a clean break. It was a couple of years of doing both at once.
While at Northwestern, Birnholtz interned as a law extern at Paxton AI, a startup building artificial-intelligence tools for legal work. The placement reads like a thesis statement: a founder who had spent a decade shipping consumer software, now embedded where software meets the practice of law. It is the same intersection Trarian would later mine.
He also did the scholarly version of the work. With professor Matthew B. Kugler, Birnholtz co-authored “True Threats, Public Safety, and Free Speech,” an empirical study of the consequences of the Supreme Court's Counterman decision, published in the Journal of Criminal Law & Criminology. It is a long way from NFT vending machines - a careful, data-driven look at where threatening speech stops being protected. The throughline is the empiricism. He has always preferred to measure the thing rather than guess at it, whether the thing is a signup funnel or a First Amendment doctrine.
Graduating cum laude in 2025 was the formal stamp on a self-directed retraining. The serial founder had decided that the most interesting unsolved problems he kept circling - value, risk, rights, who owns what - all ran through the law. So he went and learned it, then went looking for the market inside it.
He holds degrees in economics, history, information science, and law - a collector of disciplines who keeps finding ways to fuse them.
His startup sold NFTs from a sidewalk machine that took an ordinary debit card. No wallet required, which was the whole joke and the whole point.
He went from marketing meme-era collectibles to litigating patents at one of the world's largest law firms - inside of a few years.
On X he still lists his title as “cofounder & meme dealer,” a souvenir from the Neon days he hasn't bothered to update.
A patent is worth what someone will pay for it - until a court decides it was never valid in the first place.
That gap between paper value and real value is the market Trarian is chasing. Birnholtz wants to treat patents like an asset class you can underwrite, beginning with invalidity, and to do it fast enough that the analysis is useful before a deal closes or a case is filed. It is a founder's bet placed by someone who now spends his days inside the courtroom version of the same fight. Whether the patent asset class gets underwritten the way Trarian imagines is an open question. The instinct that got him here - go where the value is mispriced - is not.