CRACKED Wealth: After the Exit

Everyone in Silicon Valley will tell you how to raise, hire, and ship. Almost nobody tells you what to do the day it actually pays off.

So we're fixing that.

CRACKED Wealth is a curated, invite-only night in San Francisco for founders and operators who are approaching, navigating, or just past an exit. IPO, acquisition, secondary, tender offer, whatever it is. We're putting two founders who've literally lived it on stage and asking them everything.

THE SPEAKERS

KJ Dhaliwal, Co-founder and CEO of Lotus Health AI
KJ sold Dil Mil, the South Asian dating app, for $50 million in 2019, after taking it through Y Combinator and growing it into the largest South Asian dating app in the world. Instead of retiring, he went right back in. In May 2024 he launched Lotus Health AI, a free primary care provider available 24/7 in 50 languages, which has since raised a $35 million Series A co-led by CRV and Kleiner Perkins, bringing total funding to $41 million.

Jake Castillo, Co-founder of Cal AI
Jake left management consulting and co-founded Cal AI, the AI-powered nutrition and calorie tracking app, with Zach Yadegari, a former high school intern. The app hit over 15 million downloads and $50 million in annual revenue in under two years, and MyFitnessPal announced its acquisition of Cal AI in March 2026.

One founder is 7 years past his exit. The other is months past his. Put them side by side and you get the whole timeline of an exit in one night.

WHAT WE'RE GETTING INTO
- What to set up before the exit, not after
- QSBS, holding periods, and the tax clocks most founders don't know are running
- Lockups, tender offers, and secondaries: when to take money off the table and when to wait
- Turning a concentrated position into a real portfolio without blowing it up
- The psychological whiplash of sudden wealth that nobody warns you about
- Life after the wire hits: identity, relationships, and what comes next

THE NIGHT
6:00 PM  Doors, drinks, mingle
6:30 PM  Welcome from Goodfin
6:35 PM  Fireside chat with KJ and Jake, moderated by Viraj Ala
7:20 PM  Open AMA, nothing off limits (anonymous questions welcome)
7:40 PM  Drinks and networking with founders at the same stage

THE RULES
No pitch decks. No sales pitch. No wealth managers working the room. Just honest conversation, off the record, with people who get it. Seats are capped at 50 to keep it intimate, and every registration is reviewed by the hosts.

ABOUT THE HOSTS
Goodfin is a private markets investment platform built for founders, operators, and accredited investors: the people building what's next and deciding what to do with the wealth it creates.

Viraj Ala Media is the voice behind CRACKED. Viraj interviews Silicon Valley's top founders and investors, including partners at Sequoia, a16z, Khosla, Lightspeed, and Menlo, for an audience of 250K+ followers and 15M+ monthly views.