Jake Cahan

Seventy million Americans have debt in collections. Most of them have, at some point, been threatened - with arrest, with garnishment, with a phone that will not stop ringing. Jake Cahan looked at that number and saw a software problem hiding behind a human cruelty problem.

His company, January, is a New York fintech that does the unglamorous, deeply unfashionable work of recovering money people owe. The twist is in how. January's platform is built to be, in Cahan's own framing, both "really compliant" and "really compassionate" - and still really effective. It resolves more than 90% of accounts without a human in the loop, which means no script-reading agent, no late-night intimidation, no theater.

Cahan founded the company in 2016 under a blunter name: Debtsy. The premise was a quiet observation about incentives. Lenders, he noticed, were increasingly nervous about handing their borrowers - and their reputations - to traditional collection agencies. "Creditors aren't intentionally trying to put their borrowers in a position to be harassed," he has said. "Ultimately, they're trying to maximize the net present value of their debts." The harassment was a bug nobody had bothered to fix because the people on the receiving end had no leverage.

What makes the pitch interesting is that it is not charity. January charges a contingency fee - it earns only when a borrower actually resolves their debt. Decency, in other words, had to also be a better business. Cahan's whole thesis rests on the idea that a borrower treated like a person pays back more reliably than a borrower treated like a target.

The long, slow years of "blind fanaticism"

January did not arrive fully formed. Cahan is unusually candid about the grind. "Like many founders, I underestimated the challenge," he admits. He has described the company's early engine as "blind fanaticism" - the kind of belief that keeps you going when adoption is glacial and the prestige is nonexistent. Debt collection does not get you on magazine covers.

The first believers were credit unions. "They were excited by the prospect of delivering better experiences for their financially struggling members," Cahan says. From that foothold, January worked its way toward banks, debt buyers, and fintech lenders - the institutions that need collections to function but would rather not be associated with how it's traditionally done. Early clients included BCU, Octane, Alliant Credit Union and RBFCU.

The strategy was deliberately narrow at first. "We started off by solving the really, really hard problem of how do you collect at scale in a really compliant manner," he explains. Nail the hardest thing - compliant, humane recovery that actually works - and the adjacent problems become solvable. The frugality was a feature, not a constraint. "We focused on doing much more with much less," Cahan says. "The frugality helped us achieve some amazing results, such as being able to handle 150 times more capacity."

From real estate to recovery

Cahan did not come up through the collections world. He studied computer science at Brown University, where he was also an undergraduate teaching assistant, and did coursework in complex systems and business at the University of Michigan. His first chapters were in real estate and proptech: internships at Manocherian Brothers and Vornado Realty Trust, then a venture-investing seat at Third Prime Capital, and a data startup of his own called SourceRE, built to sharpen real-estate investment decisions with data.

That background - part engineer, part investor, part operator - shows up in how he talks about January. He frames consumer collections not as a moral lecture but as "objectively one of the most broken and antiquated parts of consumer finance." The interesting question to him is the systems question: how do you make something this large work better for everyone touching it at once?

The Series B and the bet on now

In December 2023, January closed a $12 million Series B, bringing total funding to roughly $28 million. The numbers behind it told the story Cahan had been waiting years to tell: between the Series A and the Series B, the company quadrupled both its revenue and its client count, and helped hundreds of thousands of Americans resolve debt - with millions more nudged toward firmer financial footing.

The earlier $10 million Series A, led by Brewer Lane Ventures, had come with a roster of angels that doubled as a credibility stamp: a former CEO of Credit Suisse, plus founders from Braze, Bread, GLG and TrialSpark. When asked what the Series A fundraising process was actually like, Cahan answered in a single dry word: "Riveting!" His real advice for founders is less sardonic and hard-won: "Simplify your story, then simplify it some more."

His ambition for January is unapologetically large - to become "the single platform that addresses all of those collection and recovery needs" across consumer finance. And his read on the moment is urgent. "Consumers and lenders face a financially dire situation," he has warned. "It's only getting worse." Which is exactly why, he argues, "now is the time to accelerate our growth." A decade in, the blind fanaticism has acquired some very clear eyes.

Not a solo act

Cahan co-founded January alongside Kurt Spindler, and the company has grown to roughly 120 people - a long way from the early days when headcount sat in the dozens. Between the Series A and the Series B, January more than doubled its team, a sign of a company that had stopped proving the concept and started scaling it. The technology stack underneath reflects the engineering instincts Cahan brought from Brown: a modern, cloud-native build leaning on AWS, React, React Native, Python, Snowflake and a growing roster of AI tooling.

The point of all that machinery is not to remove humans from the equation entirely - it is to make the human moments count. Traditional collections leans on volume: dial enough numbers, send enough letters, and some fraction pays. January's approach inverts the logic. By automating the compliant, repetitive groundwork, it frees the system to meet borrowers where they actually are, across whatever channel they prefer, with a complete record of every interaction. The company describes this as omnichannel debt resolution, and it is less a feature list than a worldview: people in financial distress respond to being understood, not pursued.

The contrarian math of being decent

Most fintech founders chase the glamorous front end of money - the spending, the investing, the buy-now-pay-later checkout button. Cahan went the other direction, toward the part of the cycle everyone would rather pretend doesn't exist. It is a deliberately unsexy choice, and it is precisely why January has a moat. The hard, compliance-heavy work of collecting "at scale in a really compliant manner or really compassionate but still really effective manner," as he puts it, is exactly the kind of problem competitors avoid because it offers no shortcuts.

There is a structural elegance to the model that appeals to the investor in him. Debt settlement firms are antagonistic to creditors. Collection agencies are antagonistic to consumers. January's wager is that you can stand in the middle and serve both - rehabilitating the relationship between borrower and lender rather than picking a side. When that works, the creditor recovers more, the borrower keeps their dignity, and January earns its contingency fee. Three parties, aligned, in an industry built on the assumption that someone always has to lose.

Whether that wager pays off at the scale Cahan imagines is the open question of the next few years. But the early evidence - quadrupled revenue, a quadrupled client base, hundreds of thousands of resolved accounts, and a Series B raised in a brutal funding climate - suggests the contrarian bet has legs. In June 2025, he turned up on the Founders Friday series to tell the story to a new audience, still the same founder who once described his own fuel as blind fanaticism, now with a decade of receipts to back it up.