In case you’re new here: LandonsLoop.com is the fastest growing newsletter covering Chicago.

Every Monday morning, I keep readers in the loop with breaking news, upcoming tech events, and now interviews with Chicagoans building meaningful things in the city.

Today I’m announcing a new column: Chicago Futurist.

It’s an interview series with founders, operators, and leaders that are transforming Chicago. Folks I’m genuinely bullish about.

Each conversation will share real insights on how startups are being built here, where founders find the best talent, how execs are thinking about AI, and how political leaders make decisions that shape our city.

The goal is simple: share knowledge and help Chicago build faster, smarter, and more connected.

I’m solving Chicago’s storytelling problem. We have the talent, companies, and big ideas here. It’s time to spotlight the people doing the work.

Adi Tantravahi is the CEO of Cofactor, a Chicago-based startup tackling one of healthcare’s most broken systems: how hospitals get paid.

Here’s our conversation:

AT: Cofactor builds AI that helps hospitals get paid for the care they’ve already provided. When a hospital submits a claim to an insurance company, about 15–20% get denied, often incorrectly. We review clinical documentation to make sure the claim and documentation tell the same story, and we automate the appeal process so hospitals can recover revenue they’re legitimately owed.

Denials are a $250 billion problem that health systems have largely accepted as the cost of doing business. Most appeals never get written because the labor costs more than the claim itself, leaving a massive pool of legitimate revenue uncollected.

Denials are also a wedge into the broader revenue cycle. By understanding why claims get denied and how to appeal them effectively, we’re uniquely positioned to prevent them and expand into the full spectrum of revenue integrity, starting with a clear entry point and immediate, measurable ROI.

AT: We knew it was working right out of the gate when we managed to 4x appeal efficiency almost immediately. A few months later, the real validation came when we started doubling the overturn rate for our partners. Teams went from skeptical to becoming our biggest advocates, proactively introducing us to other health systems and talking about expanding to more use cases. When things became repeatable across systems, we knew we were onto something.

We earn trust by starting small, proving value quickly, and deliberately driving change management. We set clear success metrics, provide full transparency into what our AI is doing, and keep humans in the loop.

We always show our work, including clinical reasoning, regulatory citations, and evidence so teams can audit everything. Just as importantly, we respect their expertise and work with them to refine the product. These teams know denials and clinical evidence better than any AI ever will, so the product is built to augment, not replace.

AT: We chose to build in Chicago for personal reasons, but it’s turned out to be a massive advantage for Cofactor. There’s a lot of alpha in the Midwest talent pool that sometimes gets overlooked, with incredible talent coming out of the universities here and people focused on execution and building things that matter.

It also turned out to be an incredible healthcare hub. Becker’s Healthcare is based here, so at least once a quarter, potential customers from around the country come to the city. There’s a constant stream of healthcare conferences and events we can tap into.

And from a recruiting standpoint, Chicago sells itself. World-class food scene, incredible architecture, museums, theatre, live music. It's not hard to convince people to move here, especially in the summertime.

We're excited to work with more Chicago health systems as we grow.

When building the team, we look for exceptionally smart people who deeply care about their work and making the world a better place. Everyone has to be comfortable moving at incredible velocity, wearing multiple hats, and figuring things out as they go.

We also prioritize in-person work. There’s no substitute for the speed of iteration, density of communication, and culture-building that happens when you’re in the same room solving complicated problems together.

AT: Our team operates with a simple principle that's hard to deliver: we provide value regardless of whether someone buys from us. We've found that giving healthcare professionals high-quality information in an easy-to-digest format, filled with insights that help them do their jobs better, makes them more willing to hear us out and trust us.

It's also a unique way to communicate with a market that's used to boring, low-effort SEO slop that provides zero actual value.

This market is crying out for authentic content that shows they're being heard. This is how we show them we care about their problems, we're committed to continuously innovating and solving those problems in a way that delivers demonstrably superior ROI, and we're taking the time to understand payer behavior and stay ahead of the game for them. We show our work, and people appreciate that.

AT: We started 2025 with zero health systems and ended it with four. We’re on track to triple that by the end of 2026, integrated into the daily workflow of hundreds of revenue cycle professionals.

The US healthcare system is drowning in administrative complexity. Payer behavior gets more aggressive every year and hospitals are chronically short-staffed. The administrative burden is compounding on itself.

We don't think it has to be this way. Our mission is to be the state-of-the-art reasoning layer for all the administrative complexity that comes with clinical work. We want to reduce that burden dramatically and give hospitals access to network effects by surfacing insights into payer behavior across the country, showing them exactly why claims get denied, and using that intelligence to drive real change management.

Days before the New Year, Chicago City Council passed a $16.7B budget for 2026, closing a roughly $1.2B gap.

For tech and startups, the outcome is mixed.

The biggest win: City Council blocked the proposed corporate head tax.

The head tax would’ve charged companies about $33 per employee per month, a policy that almost would push growing companies out of Chicago. Avoiding this was critical for keeping our city competitive.

The biggest hit: a higher digital tax.

Chicago raised taxes on software licenses, cloud services, and other digital goods from 11% to 15%.

While framed as a tax on “big tech,” it applies broadly to any company using SaaS or cloud infrastructure, including startups. This directly increases operating costs across the ecosystem.

The big takeaway: Chicago avoided its most damaging idea, but still chose to raise costs in other ways.

It’s also worth noting that a significant number of aldermen (along with the mayor) supported the head tax proposal.

Remember that before the next election.

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