Both Parents Are Doctors. He Still Didn't Get It.
ikhil Krishnan grew up in a household full of medical expertise. Both parents: physicians. Healthcare: dinner table conversation. And yet somehow, the American health system remained bewildering - a maze of acronyms, misaligned incentives, and bureaucratic absurdity that even the children of doctors couldn't parse without a translator.
That tension - deeply personal, stubbornly confusing - became the founding thesis of Out-of-Pocket. Not a policy brief. Not a clinical journal. A newsletter that asked a radical question: what if we made healthcare actually entertaining to learn about?
The answer, launched in February 2020 at possibly the most consequential moment in modern healthcare history, was a resounding yes. Out-of-Pocket grew from zero to 30,000+ subscribers with a combination of sharp analysis, genuinely funny memes, and a refusal to hide behind jargon. The tagline is no accident: "Come for the memes, stay for the analysis. Or just stay for the memes, whatever floats your boat."
Before Out-of-Pocket, Krishnan was already building something. At CB Insights, he ran the healthcare research desk and grew their health newsletter to over 90,000 subscribers - a fact that should be noted more often when people talk about Nikhil as an overnight success. After that, he spent time at TrialSpark as a Strategic Partnerships Manager, working at the intersection of clinical trials and business development. He graduated from Columbia University in 2014 with a background in sustainable development and business management. His early career included stints at Uber, the Small Business Administration, and Relationship Science - the kind of eclectic resume that produces people who see every industry from the outside.
What makes Krishnan unusual in the healthcare media landscape isn't just the humor - it's the systems thinking underneath. He has consistently identified structural problems others gloss over: the principal-agent problem where insurers pay for what patients use (killing price sensitivity); the layered regulatory mess of federal rules atop state subsets atop employer contracts; the way "midline" healthcare policy manages to capture the worst of both government regulation and free-market competition without the benefits of either.
He's not a pundit. He's a cartographer of dysfunction who happens to be very funny about it.
More Than a Newsletter
Out-of-Pocket started as a Substack. It became something harder to categorize: part media brand, part education platform, part community hub, part venture pipeline. The newsletter remains the core - a weekly deep-dive into the business of healthcare that treats readers as smart adults capable of handling real complexity, as long as it comes with a few well-placed memes.
But Krishnan has built the surrounding infrastructure with the same logic he uses to analyze healthcare: find the system's pressure points, build something useful there. Healthcare crash courses launched with 1,000+ signups and 250+ attendees showing up live. Hackathons with Google Cloud and Deerfield followed. A job board. An invite-only Slack community for healthcare innovators. A scout fund for early-stage investing.
Investing Thesis
Krishnan backs early-stage healthcare startups through a scout fund - a natural extension of a media brand that talks to more healthcare founders than most seed-stage VCs. Here's what he's looking for:
Career Timeline
Achievements
- Built Out-of-Pocket newsletter from 0 to 30,000+ subscribers
- Grew CB Insights healthcare newsletter to 90,000+ subscribers before founding his own
- Created and sold a medical bankruptcy card game on Amazon
- Self-published "If You Give A Mouse Metformin" - an illustrated children's book about clinical trials
- Launched crash courses with 1,000+ signups and 250+ live attendees per run
- Hosted events and hackathons with 32 sponsors in a single year
- Co-hosted AI hackathons with Deerfield and Google Cloud
- Built and runs a scout fund for early-stage healthcare startups
- Featured in Crain's New York Business, Nieman Journalism Lab, Substack Podcast
- Founded Get-Real Club - a platform for structured social connection on the internet
Quotes
Who He Is
Krishnan is the kind of person who spends six months building a card game about medical bankruptcy - not to make money, not to build an audience, but because it's funny to him. That instinct runs through everything he does. The humor isn't a hook to get people to read serious content. The humor IS the serious content. Healthcare is absurd. Acknowledging that isn't making light of something important - it's the most accurate possible take.
He's also a connector. The Get-Real Club, the Slack community, the bar talk series, the walking tours - these aren't marketing tactics. They're expressions of someone who genuinely believes that most interesting things happen at the intersection of people who wouldn't otherwise meet. Out-of-Pocket the newsletter became Out-of-Pocket the ecosystem partly because Krishnan treats his readers less like an audience and more like an ongoing conversation he's been meaning to have.
His approach to investing mirrors his approach to media: build genuine expertise first, let the financial opportunity follow. The scout fund wasn't the plan when he started the newsletter in 2020. But five years of deep-dive healthcare analysis and a community of healthcare founders and operators means he now sees opportunities earlier than most, and with better context than almost anyone.