In this episode, I sat down with Jeff LoCastro, a serial entrepreneur, innovation “artist,” and the Founder/CEO of Neener Analytics. Jeff’s built and scaled companies across wildly different industries (including being part of the early executive team behind Classmates.com) and he’s got a rare ability to spot patterns “100 miles down the road” before most people even see the first mile.

We get into how Jeff thinks about entrepreneurship, why “zero to one” misses the point, and what it really takes to turn “pixie dust” (a crazy idea) into something so real that Visa wants to partner with you. Then we dive deep into Neener’s mission: helping people build financial identity using small data, so consumers can own their personal data and use it on their own terms.

1. [2:10] — Jeff on why he’s “never had a real job” and why corporate life was never going to fit
2. [6:45] — The real origin story of Classmates.com (and why the “college dropout at 2am” myth is… a myth)
3. [13:30] — Jeff’s through-line across industries: following problems he can see “100 miles ahead”
4. [19:40] — Why Jeff calls himself an artist, and what that reveals about building companies
5. [27:55] — “Zero to one” vs. zero to 100: where the real difficulty (and reward) actually lives
6. [34:30] — The goosebumps moment: pitching, then hearing Visa say “we want to partner with you”
7. [40:20] — Neener Analytics explained: cracking the code on small data + cognitive AI for financial risk
8. [47:15] — The “two bankers” story: “I know you” vs. “I know people like you” (and why big data fails people)
9. [55:10] — Real-world results: reducing defaults and recapturing approvals with a “single click”
10. [1:02:40] — What changes when consumers can use personal data like currency, and why it means less to steal
11. [1:10:15] — Jeff’s advice to founders: don’t build from consensus, trust your gut (and learn fast if it’s wrong)

1. Jeff’s LinkedIn: https://www.linkedin.com/in/jeff-locastro-24087b15/
2. Jeff’s Website: https://neeneranalytics.com/
3. Patent Hacks Website: https://www.patenthacks.com
4. Trevor Skene LinkedIn: https://www.linkedin.com/in/trevor-skene/