How AI Can Fix Gen Z’s Financial Gaps with Jason Schappert from Moola

I am thrilled to have Jason Schappert, the CEO of Moola, an AI-powered stock scoring and decision engine designed to empower the next generation of investors to achieve true financial freedom. Earlier - MzeroA was named one of the Inc. 500’s top-growing private companies and recognized as a “Best Place to Work.”

In this episode, Jason Schappert, founder of Moola, shares his journey from pest control routes to an eight-figure exit. Jason dives into bootstrapping his aviation edtech startup, turning early YouTube lessons into a thriving business, and scaling with scrappy tools and mindset. He unpacks key lessons on culture, hiring, and preparing for acquisition—plus why clean books matter more than user growth. Jason also discusses starting Moolah, an AI-powered finance app, and his philosophy on investing, crypto, and building through downturns. He shares advice on feature-locking MVPs, no-code tools, and embracing AI early—and much more!

Timestamps

00:02 – Jason's origin story: growing up in an entrepreneurial family and moving to Florida.

01:41 – Early lessons from his parents and his first flying experience at age 12.

03:31 – Starting MZeroA from his parents' house and his "wrong side of the deal" realization.

05:53 – Discovering GoPro cameras and using them to film flight lessons.

07:42 – Turning YouTube videos into a subscription-based business.

10:07 – The powerful advice: "You don’t have to get it right, you just have to get it going."

11:49 – Losing their first acquisition deal due to messy bookkeeping.

14:08 – Turning the loss into an opportunity: hiring a fractional CFO and cleaning up the books.

16:38 – Viewing an acquisition like dating: aligning visions with the buyer is critical.

18:25 – Culture wake-up call: “This business is like a fraternity that makes money.”

20:46 – Hiring based on culture fit, not just skill; story of a cop-turned-COO.

22:44 – Jason’s hiring criteria: personality, hunger to learn, curiosity.

23:25 – Managing extreme personalities and team morale during exits.

25:37 – Post-exit identity crisis and getting back in the game within 48 hours.

28:02 – The philosophy of “hit the ball in one more time” and launching Moolah.

29:57 – Using AI to help users identify small savings and grow investments.

31:55 – How Jason allocates his portfolio across stocks, crypto, and other assets.

34:22 – XRP, Bitcoin, and the potential of #2 or #3 crypto players.

36:05 – Real estate investments: owning 600+ rental units and market observations.

37:58 – Emerging markets: ETFs, Africa, India, and policy-influenced investment strategy.

40:01 – European markets, regulation challenges, and strategic shifts.

42:14 – Building tech products without coding: tools, Upwork, and early hustling.

44:12 – Feature-locking MVPs and dealing with SEC, FINRA, FDIC regulations.

46:19 – Global expansion plans: why Latin America is next for Moolah.

48:14 – Advice to Gen Z & college grads: embrace AI, prompt engineering, and tech savviness.

Jason’s Links 

LDN– https://www.linkedin.com/in/jasonschappert/

Website – https://moo.la/

My Links 

Podcast: https://lifeselfmastery.com/itunes

Newsletter: https://partner-grow.beehiiv.com/subscribe

YouTube:  youtube.com/lifeselfmastery

Twitter: https://twitter.com/rohitmal

LinkedIn: https://www.linkedin.com/in/rohit857/

Agency: https://bit.ly/41YuNnx