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
How AI Is Shaping the Future of Sales with Doreen Pernel from Scaleway
Lifeselfmastery's podcast I Startups I Venture Capital
I am thrilled to have Doreen Pernel, Chief Sales Officer at Scaleway, Europe's leading sovereign cloud provider. She's built and scaled sales teams across Meta, Dataiku, Box, and Bloomberg, navigating Sydney, New York, London, and Paris. In this conversation, Doreen Pernel, Chief Sales Officer at Scaleway, shares her insights on sales leadership, cultural adaptability, and innovative strategies in the cloud computing industry. She discusses the importance of resilience in hiring, the evolving role of cold calling, and how to motivate teams against larger competitors. She also reflects on the...
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Unlocking Subscription Success with Daniel Layfield
Lifeselfmastery's podcast I Startups I Venture Capital
I am thrilled to have Daniel Layfield, who is Director of Product Management at Diligent and founder of Subscription Index, advising subscription businesses on monetisation. In this conversation, Daniel Layfield shares his journey from finance to product management, discussing his experiences at Code Academy and Diligent. He emphasises the importance of understanding churn, effective pricing strategies, and the role of AI in product management. Daniel also explores the complexities of subscription models, the significance of metrics, and the impact of price localisation on revenue. Timestamps...
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Scaling Product Organizations in the Age of AI with CallRail's Ryan Johnson
Lifeselfmastery's podcast I Startups I Venture Capital
I am excited to have , who is the Chief Product Officer at CallRail, an AI-powered lead intelligence platform serving 200,000+ businesses with over $100M ARR. In this conversation, Ryan Johnson, Chief Product Officer at CallRail, shares his journey from finance to product management, discussing the evolution of CallRail from a call tracking service to a lead intelligence platform. He emphasises the importance of scaling product organisations, balancing sales and product-led growth, and navigating the challenges posed by AI disruption. Ryan also delves into pricing strategies, monetisation...
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Evolution of Pricing Strategies in Business with Gary Bailey
Lifeselfmastery's podcast I Startups I Venture Capital
I am thrilled to have , founder of Strategim, a monetisation & pricing expert with a deep background in financial services, accounting, pricing, and AI. In this conversation, Gary Bailey, a monetisation and pricing expert, shares his journey from accounting to product management and pricing. He discusses the importance of pricing as a core discipline in business education, the evolving role of finance in pricing strategies, and the impact of AI on SaaS pricing models. Gary emphasizes the need for training the next generation in pricing and the role of a monetization architect in modern...
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Art of Pricing Strategies in SaaS with Naveen Mohan at Otter
Lifeselfmastery's podcast I Startups I Venture Capital
I am thrilled to have Naveen Mohan, who leads monetisation at , bringing deep experience from Adobe and Loom. With a Carnegie Mellon Information Systems degree and software engineering background, he combines data science expertise with product management. In this conversation, Naveen Mohan, Product and Monetisation Lead at Otter.ai, shares his journey from data science to product management, emphasising the importance of experimentation in pricing strategies and the evolution of monetisation in tech startups. He discusses the balance between soft and hard paywalls, the rise of hybrid pricing...
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How Superlinked is building the Next Generation of AI Search with Ben Gutkovich
Lifeselfmastery's podcast I Startups I Venture Capital
I am excited to have , co-founder of , helping AI engineers build information retrieval systems using vector embeddings. In this conversation, Ben Gutkovich, co-founder of Superlink, shares his journey from a software engineer to an entrepreneur in the AI space. He discusses the differences between consulting and building technology, the challenges of recruiting talent in a competitive market, and innovative strategies for business development. Ben also addresses the impact of remote work on startups, insights into M&A deals, and predictions for the future of AI. He emphasises the...
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Future of Fundraising in the Age of AI with Casey Woo of Operators Guild
Lifeselfmastery's podcast I Startups I Venture Capital
I am excited to have , founder of , a community of 800+ top operators. He is also a General Partner at FOG Ventures, where he's witnessing how AI is killing the 18-month fundraising cycle, enabling 1000x returns in half the time. In this conversation, Casey Woo, founder of Operators Guild and general partner at Fog Ventures, discusses his journey from Wall Street to the startup world, the evolving landscape of fundraising, and the impact of AI on job roles and business operations. He emphasises the importance of generalists in startups, the need for effective distribution strategies, and the...
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Navigating the Crypto Landscape with Harvey Liu of Levex Exchange
Lifeselfmastery's podcast I Startups I Venture Capital
I am happy to have Harvey Liu, the CEO of , where he’s building a cutting-edge platform for spot and futures trading in digital assets. In this conversation, Harvey Liu, CEO of Levex Exchange, discusses his journey from computer science to venture capital and now leading a crypto exchange. We explore misconceptions about blockchain, the psychology of trading, the challenges of asset tokenisation, and the importance of a strong team and culture in business. Harvey shares insights on investing principles, strategies for startups going global, and the dynamics of venture capital, emphasising...
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Transforming Education Through Digital Infrastructure with Shankar Maruwada from EkStep Foundation
Lifeselfmastery's podcast I Startups I Venture Capital
I am excited to have , Co-Founder and CEO of EkStep Foundation, a pioneering non-profit working to improve learning outcomes for millions of children in India through technology and learner-centric platforms. Shankar has been featured in ’s ‘Policy 50’, a definitive list of the 50 leaders who are steering and shaping India’s digital economy. In this conversation, Shankar Maruwada shares his journey from corporate leadership to social impact through the Ekstep Foundation. He discusses the importance of digital infrastructure in education, the lessons learned from the Aadhaar initiative,...
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Investing in Peace with Shane Martin of B Ventures
Lifeselfmastery's podcast I Startups I Venture Capital
I am excited to have —a venture capitalist who’s rewriting the playbook for what investing can look like. He’s an investor at , the first-of-its-kind global peace VC fund that backs tech founders building solutions for both profit and peace. In this conversation, Shane Ray Martin, a venture capitalist at B-Ventures, discusses his unique journey into the world of venture capital, emphasising the potential profitability of peace tech. He shares insights on the challenges of pitching peace tech to investors, common mistakes founders make in their pitches, and the balance between instincts...
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/
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