How AI Can Fix Gen Z’s Financial Gaps with Jason Schappert from Moola
Lifeselfmastery's podcast I Startups I Venture Capital
Release Date: 06/19/2025
Courageous Marketing: How Udi Ledergor Scaled Gong from Zero to Unicorn
Lifeselfmastery's podcast I Startups I Venture Capital
I am thrilled ot have the Chief Evangelist at Gong, where he spent nine years helping build the company from zero to a multi-billion-dollar valuation. A five-time B2B marketing leader, bestselling author of Courageous Marketing, angel investor, and board member In this conversation, Udi Ledergor, Chief Evangelist at Gong, shares his journey from product management to leading marketing at a billion-dollar company. He emphasizes the importance of human-centric marketing, the need to challenge traditional best practices, and the significance of creating valuable content that resonates with...
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Railsware's Journey from Agency to SaaS Powerhouse with Sergiy Korolov
Lifeselfmastery's podcast I Startups I Venture Capital
I am excited to have Sergiy, who is the Co-CEO of Railsware and co-founder of multiple products In this conversation, Sergiy Korolov, CEO of Railsware, discusses his journey from software developer to entrepreneur, the evolution of his products like Mailtrap and Coupler, and the challenges faced in the tech industry. Sergiy shares insights on transitioning from service to product, the importance of understanding user segments through surveys, and the role of AI in enhancing productivity. He also reflects on the complexities of email delivery and strategies for competing against larger...
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Rise of Defence Tech from Brad Harrison from Scout Ventures
Lifeselfmastery's podcast I Startups I Venture Capital
I am thrilled to have , a former Army Ranger turned venture capitalist, and the founder and Managing Partner of Scout Ventures. Brad invests at the intersection of national security and critical technology innovation, backing companies like Unite Us, ID.me, Voyager Space, and Tomahawk Robotics — which was recently acquired by AeroVironment. In this conversation, Brad Harrison, a former Army Ranger turned venture capitalist, shares his journey into the world of venture capital and the founding of Scout Ventures. He discusses the importance of mission-driven investments, particularly in the...
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Emerging Market Lessons That Make Better Investors with Elias Mufarech from Collide Capital
Lifeselfmastery's podcast I Startups I Venture Capital
I am thrilled to have who is a Senior Associate at Collide Capital, a pre-seed to Series A venture fund investing in fintech, future of work, and supply chain software. In this conversation, Elias Mufarech, a senior associate at Collide Capital, shares his insights on venture capital, the importance of operational support for founders, and the evolving landscape of startup expectations. Elias discusses his journey from building fintech software in Latin America to investing in startups, highlighting the critical lessons learned along the way. He emphasizes the need for founders to have strong...
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Ankur Patel from Multimodal on Building Agentic AI for the Enterprise
Lifeselfmastery's podcast I Startups I Venture Capital
I am excited to have who is the founder and CEO of , where he's automating the most complex workflows in finance and insurance. He has 15+ years of work experience across companies like J.P. Morgan and Bridgewater In this conversation, Ankur Patel, founder and CEO of Multimodal, traces his path from JP Morgan and Bridgewater to building AI agents that automate complex workflows in finance and insurance. He explains how early exposure to data science and macro trading convinced him that AI would reshape enterprise work. He discusses why agentic AI is fundamentally different from...
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How Vivek Krishnamurthy from Commerce Ventures Thinks About Venture, AI, and Markets
Lifeselfmastery's podcast I Startups I Venture Capital
I am thrilled to have , who is a Partner at , where he's spent over 8 years investing in commerce infrastructure and fintech. Before Venture, he was an Investment Banking Analyst at Financial Technology Partners. He's particularly bullish on AI's transformation of insurance, backing companies like Kin Insurance, Liberate, and Authentic. In this conversation, Vivek Krishnamurthy, a partner at Commerce Ventures, discusses his journey into venture capital, the evolution of investment strategies, and the intersection of commerce and fintech. Vivek shares insights on the impact of AI on business,...
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Dallas Price from Forum Ventures on Venture Studios, Founder-Market Fit, and What Actually Wins in AI
Lifeselfmastery's podcast I Startups I Venture Capital
I am excited to have , a Venture Builder at , where he helps launch and scale six B2B SaaS startups every year through their AI Studio. His work centres on turning early-stage concepts into real companies, guiding founders across product, go-to-market, and fundraising In this conversation, Dallas Price, a venture builder at Forum Ventures, discusses his journey into the startup world, the workings of a venture studio, and the current landscape of AI startups. Dallas shares insights on navigating chaos in startups, the importance of defensibility, new distribution channels, and evolving pricing...
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Capital Evolution: A New Era of Capitalism with Seth Levine and Elizabeth McBride
Lifeselfmastery's podcast I Startups I Venture Capital
I am excited to have , venture capitalist and co-founder of Foundry, and , international business journalist and founder of Times of Entrepreneurship. Together, they co-authored The New Builders and now their latest book, , explores how American capitalism is shifting—and why businesses, not government, may hold the keys to building a more inclusive and prosperous future. In this conversation, Seth Levine and Elizabeth McBride discuss their new book, 'Capital Evolution,' which explores the shifting landscape of American capitalism. They delve into the challenges posed by neoliberal...
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Art and Science of Pricing Strategies with Marcos Rivera of Pricing I/O
Lifeselfmastery's podcast I Startups I Venture Capital
I am thrilled to have , the founder and CEO of , where he helps B2B SaaS companies capture the value they've built. Former Head of Pricing at Vista Equity Partners, he's priced over 400 SaaS products and has authored Street Pricing. In this conversation, Marcos Rivera, founder and CEO of Pricing.io, discusses the intricacies of pricing strategies in B2B SaaS. Marcos shares his journey from product management to pricing, highlighting common mistakes companies make, especially in underpricing their products. He emphasizes the importance of understanding customer needs, the blend of art and...
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Navigating the AI Investment Landscape with Aabhas Khanna of MyAsia VC
Lifeselfmastery's podcast I Startups I Venture Capital
, is General Partner at MyAsiaVC, a venture syndicate and fund with $125M AUM backing 250+ companies, including 5 unicorns. Previously at HSBC and Deloitte, he now invests in pre-seed and seed AI-native startups across enterprise growth, healthcare, fintech, and advanced manufacturing, focusing on obsessive founders tackling overlooked challenges. In this conversation, Aabhas Khanna, a general partner at MyAsia VC, discusses his journey from working in large corporations to venture capital. Aabhas shares insights on evaluating AI startups, the importance of founder quality, and the unique...
info_outlineI 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
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YouTube: youtube.com/lifeselfmastery
Twitter: https://twitter.com/rohitmal
LinkedIn: https://www.linkedin.com/in/rohit857/
Agency: https://bit.ly/41YuNnx