The Trader Who Builds Billion-Dollar Companies: Tom Sosnoff on Thinkorswim, Tasty, and What Comes Next

Send us Fan MailI sat down with Max Levchin, Co-Founder and CEO of Affirm and one of the living legends of tech and fintech. He co-founded PayPal with Peter Thiel and Elon Musk, invented anti-fraud technology that's still foundational today, and has spent the last 14 years building Affirm into one of the largest publicly traded fintechs in the world with a mission to replace credit cards with transparent lending. He is one of the most thoughtful and brilliant founders I've spoken with. Want more podcast episodes? Join me and follow Fintech Leaders today on Apple, Spotify, or your favorite podcast app for weekly conversations with today’s global leaders that will dominate the 21st century in fintech, business, and beyond.Do you prefer a written summary? Check out the Fintech Leaders newsletter and join ~85,000+ readers and listeners worldwide!Miguel Armaza is Co-Founder and General Partner of Gilgamesh Ventures, a seed-stage investment fund focused on fintech in the Americas. He also hosts and writes the Fintech Leaders podcast and newsletter.Miguel on LinkedIn: https://bit.ly/3nKha4ZMiguel on Twitter: https://bit.ly/2Jb5oBcFintech Leaders Newsletter: https://bit.ly/3jWIpqp

Send us Fan MailI sat down with Rob Heyvaert, Founder and Managing Partner of Motive Partners, a fintech-focused private equity firm with over $6Bn in AUM, 80 portfolio companies representing over $15 trillion of assets in the wealth management space. Rob is a serial entrepreneur who started his first company at 24, sold it to IBM, and later founded Capco and sold to FIS to hundreds of millions of dollars, before launching Motive in 2016. He is a true fintech builder and it was inspiring to learn from him. We recorded this episode live at Motive's NYC office as part of New York Fintech week.Want more podcast episodes? Join me and follow Fintech Leaders today on Apple, Spotify, or your favorite podcast app for weekly conversations with today’s global leaders that will dominate the 21st century in fintech, business, and beyond.Do you prefer a written summary? Check out the Fintech Leaders newsletter and join ~85,000+ readers and listeners worldwide!Miguel Armaza is Co-Founder and General Partner of Gilgamesh Ventures, a seed-stage investment fund focused on fintech in the Americas. He also hosts and writes the Fintech Leaders podcast and newsletter.Miguel on LinkedIn: https://bit.ly/3nKha4ZMiguel on Twitter: https://bit.ly/2Jb5oBcFintech Leaders Newsletter: https://bit.ly/3jWIpqp

Send us Fan MailI sat down with Renaud Laplanche, Co-Founder and CEO of Upgrade, a consumer fintech valued at $7.3 billion. Since 2017, Upgrade has originated over $45 billion in credit to 7.5 million customers, crossed $1 billion in annualized revenue, and has been cash flow positive for years. Renaud also founded Lending Club and took it public in what was the largest US tech IPO of 2014. He is one of the most accomplished entrepreneurs in fintech and someone I personally admire. We discussed building a multi-product platform from day one, how a company acquisition became their best customer generation engine, the first AI-native product Upgrade is shipping soon, and much more. Outside fintech, Renaud is an avid Sailor holds the Guinness World Record for the fastest Newport to Bermuda sailing crossing. Want more podcast episodes? Join me and follow Fintech Leaders today on Apple, Spotify, or your favorite podcast app for weekly conversations with today’s global leaders that will dominate the 21st century in fintech, business, and beyond.Do you prefer a written summary? Check out the Fintech Leaders newsletter and join ~85,000+ readers and listeners worldwide!Miguel Armaza is Co-Founder and General Partner of Gilgamesh Ventures, a seed-stage investment fund focused on fintech in the Americas. He also hosts and writes the Fintech Leaders podcast and newsletter.Miguel on LinkedIn: https://bit.ly/3nKha4ZMiguel on Twitter: https://bit.ly/2Jb5oBcFintech Leaders Newsletter: https://bit.ly/3jWIpqp

Send us Fan MailI sat down with Tom Sosnoff, one of the most successful entrepreneurs in financial services. Tom spent 19 years on Chicago’s CBOE trading floor and then left to build Thinkorswim, the first online broker specialized in options, which he sold to TD Ameritrade for $600 million. He then built Tastytrade and sold it nine years later for a billion dollars to IG Group. He is now building Lossdog, a career optimization platform to help fight wealth inequality. What I enjoyed the most of this conversation is how genuine Tom is. He’s kind and cares about fairness and inequality. Prioritizes legacy over money. And he is a builder at heart that loves to take risks.Want more podcast episodes? Join me and follow Fintech Leaders today on Apple, Spotify, or your favorite podcast app for weekly conversations with today’s global leaders that will dominate the 21st century in fintech, business, and beyond.Do you prefer a written summary? Check out the Fintech Leaders newsletter and join ~85,000+ readers and listeners worldwide!Miguel Armaza is Co-Founder and General Partner of Gilgamesh Ventures, a seed-stage investment fund focused on fintech in the Americas. He also hosts and writes the Fintech Leaders podcast and newsletter.Miguel on LinkedIn: https://bit.ly/3nKha4ZMiguel on Twitter: https://bit.ly/2Jb5oBcFintech Leaders Newsletter: https://bit.ly/3jWIpqp

Send us Fan MailI sat down with Andrew Endicott, fintech entrepreneur and my co-founder at Gilgamesh Ventures. Andrew is also the author of the recent book "Is Finance Technology?", a practical guide for founders, operators, and investors in financial services. The book covers everything. From the common mistakes that kill fintech companies, to how to think about risk, fraud, and regulation across verticals.I highly recommend picking up a copy. Few people have operated across as many roles and verticals as Andrew has. Having been a financial services lawyer, investment banker, entrepreneur, board member, and now investor, this book reflects that breadth.Timestamped Overview:00:00 Finance origins and early technology05:56 Necessity driving creativity07:42 Solving everyday consumer challenges13:49 Impact of emerging technologies16:44 Fintech innovation and successful founders19:30 Challenges of choosing customers and partners21:39 Dealing with fraud challenges26:00 First movers in payment industry31:11 Writing the book and changing views32:46 Fintech companies becoming banks37:01 Venture capital trends and shifts39:32 Writing process and challenges42:27 Hoping to inspire future entrepreneursWant more podcast episodes? Join me and follow Fintech Leaders today on Apple, Spotify, or your favorite podcast app for weekly conversations with today’s global leaders that will dominate the 21st century in fintech, business, and beyond.Do you prefer a written summary? Check out the Fintech Leaders newsletter and join ~85,000+ readers and listeners worldwide!Miguel Armaza is Co-Founder and General Partner of Gilgamesh Ventures, a seed-stage investment fund focused on fintech in the Americas. He also hosts and writes the Fintech Leaders podcast and newsletter.Miguel on LinkedIn: https://bit.ly/3nKha4ZMiguel on Twitter: https://bit.ly/2Jb5oBcFintech Leaders Newsletter: https://bit.ly/3jWIpqp

Send us Fan MailI sat down with Ali Mazanderani, Chairman of Lesaka, a nasdaq traded, leading fintech in Southern Africa with over $400 million in revenue and 2 million active customers. Ali is a fintech veteran investor and builder, who’s been closely involved with several multi-billion dollar fintechs in emerging markets, including Stone, Pine Labs, Kushki, Thunes and is also a co-founder of Teya.‌We discussed why Southern Africa is one of the most exciting fintech opportunities in the world, how Lesaka is turning 120,000 merchants from cash-only to digital, the strategy behind acquiring Bank Zero, and why being a publicly traded company is a feature, not a bug.Timestamped Overview:00:00 Intro & Ali’s Background05:00 Creating positive impact through fintech09:23 Founding Taya Joy in Building10:32 Customer first approach to success14:49 Benefits of Public Market Discipline18:12 Fintech's Limited Impact in Africa20:36 South Africa's business opportunities25:45 Bank Zero Digital Advantage27:46 Customer-First Mindset & Innovation32:27 Key Focus Growth and ARPU Trends33:41 Value Over Price Wins Customers38:35 Driving Merchant Payment Efficiency42:52 Digitizing Africa's Future43:58 Ambition for global excellence47:14 Authenticity and empathy drive successWant more podcast episodes? Join me and follow Fintech Leaders today on Apple, Spotify, or your favorite podcast app for weekly conversations with today’s global leaders that will dominate the 21st century in fintech, business, and beyond.Do you prefer a written summary? Check out the Fintech Leaders newsletter and join ~85,000+ readers and listeners worldwide!Miguel Armaza is Co-Founder and General Partner of Gilgamesh Ventures, a seed-stage investment fund focused on fintech in the Americas. He also hosts and writes the Fintech Leaders podcast and newsletter.Miguel on LinkedIn: https://bit.ly/3nKha4ZMiguel on Twitter: https://bit.ly/2Jb5oBcFintech Leaders Newsletter: https://bit.ly/3jWIpqp

Send us Fan MailMiguel Armaza interviews George Robson, Partner at Sequoia Capital, one of the most legendary venture firms in the world. Founded in 1972 by Don Valentine, Sequoia has backed some of the most successful tech and fintech companies in history including Nvidia, Apple, Google, Nubank, and Stripe. Sequoia-backed companies make up over 25% of the Nasdaq's market cap, and add up to $13+ trillion in market cap.George is one of 19 investing partners at Sequoia and was previously a product manager at Revolut. We discuss how Revolut built a multi-product machine by treating every team like a startup, how Sequoia uses storytelling to calibrate its investors on what generational founders look like, and why the next wave of fintech winners will be full stack companies that internalize the technology instead of selling it to incumbents.Timestamped Overview00:00 Intro & George’s Background04:14 Finding My People at Revolut07:37 Building Self Sufficient Cross Functional Teams10:57 Focus on Growth and Profitability14:45 Crucial Decision and Growth17:49 High-Conviction Investment Strategy19:07 Parth's Inspiring Entrepreneurial Path23:38 Entrepreneur Growth and Resilience28:19 Storytelling Key to Early Success31:05 Effective Board Dynamics34:14 Entrepreneurs Investors and Problem Discovery36:42 Outsiders Tackling Big Markets40:21 Rewriting Business Laws of Gravity44:04 Humbling Reads and Insights46:17 Doug Leone Fierce and KindWant more podcast episodes? Join me and follow Fintech Leaders today on Apple, Spotify, or your favorite podcast app for weekly conversations with today’s global leaders that will dominate the 21st century in fintech, business, and beyond.Do you prefer a written summary? Check out the Fintech Leaders newsletter and join 80,000+ readers and listeners worldwide!Miguel Armaza is Co-Founder and General Partner of Gilgamesh Ventures, a seed-stage investment fund focused on fintech in the Americas. He also hosts and writes the Fintech Leaders podcast and newsletter.Miguel on LinkedIn: https://bit.ly/3nKha4ZMiguel on Twitter: https://bit.ly/2Jb5oBcFintech Leaders Newsletter: bit.ly/3jWIp

Send us Fan MailMiguel Armaza sits down with Michael Calvey, one of the most successful and legendary emerging markets investors of our time. Mike moved to Moscow at age 27 in the early 90s and built Baring Vostok into a powerhouse with $10+ billion invested in Russia. They backed now-decacorns like Yandex, Revolut, Tinkoff, and Kaspi at their earliest stages. Yandex alone was a 450x return for the fund.Along the way, he survived a 98% market crash, was detained by Russia's secret service, and made billions of dollars for his investors.He's also incredibly thoughtful about the ingredients of great founders, what separates the ones who win from those just chasing money, how the best companies constantly stack new S curves, and why being a hands-on owner but never a hands-on manager is the key to a great investor-founder partnership.Timestamped Overview00:00 From Oklahoma to Russia - Intro & Michael’s Background10:32 Building an Elite Emerging Markets Team14:36 Geopolitics, Economics, and Market Resilience20:25 Fewer Investments, Better Focus24:08 Successful Entrepreneurs Value Purpose28:47 Management KPIs and Key Insights33:45 3 Cs of Ownership Focus42:53 Marketplace vs. Fintech Growth Dynamics44:02 Marketplace Dominance and Financial Complexity52:25 Emerging Markets: Talent vs. Geopolitics54:51 Emerging Markets and Fintech Ventures01:00:20 Medici Family: Banking and Intrigue01:05:59 Starting Over as Entrepreneur Want more podcast episodes? Join me and follow Fintech Leaders today on Apple, Spotify, or your favorite podcast app for weekly conversations with today’s global leaders that will dominate the 21st century in fintech, business, and beyond.Do you prefer a written summary? Check out the Fintech Leaders newsletter and join ~85,000+ readers and listeners worldwide!Miguel Armaza is Co-Founder and General Partner of Gilgamesh Ventures, a seed-stage investment fund focused on fintech in the Americas. He also hosts and writes the Fintech Leaders podcast and newsletter.Miguel on LinkedIn: https://bit.ly/3nKha4ZMiguel on Twitter: https://bit.ly/2Jb5oBcFintech Leaders Newsletter: https://bit.ly/3jWIpqp

Send us Fan MailMiguel Armaza welcomes Edward Woodford, founder and CEO of ZeroHash, to Fintech Leaders for a candid, insightful conversation on the future of blockchain infrastructure and the lessons learned from nearly a decade of building in crypto.Edward offers a unique perspective as a London-born, MIT-educated entrepreneur who’s seen ZeroHash grow into one of the most critical and least visible companies powering the global blockchain ecosystem. He shares his journey— from getting rejected by Oxford and taking the leap to the US, to building his first fintech business and discovering Bitcoin at the MIT bookstore.Join Miguel and Edward for a conversation packed with actionable insights for fintech founders, builders, and investors aiming to navigate the fast-evolving landscape at the intersection of crypto, infrastructure, and financial innovation.Timestamped Overview00:00 Intro & Edward’s Background05:49 Balancing Business and Personal Life08:58 MIT Bitcoin and Career Exploration13:14 Tech-Driven Market Shift Insights16:07 Tokenization and Global Interoperability20:08 Impact of the founding team21:54 Founding team dynamics explored26:32 Power versus influence in investing29:25 Effective Infrastructure Pricing Strategy33:44 Weighted performance-based churn metric35:00 Founder Mode Intensity DefinedWant more podcast episodes? Join me and follow Fintech Leaders today on Apple, Spotify, or your favorite podcast app for weekly conversations with today’s global leaders that will dominate the 21st century in fintech, business, and beyond.Do you prefer a written summary? Check out the Fintech Leaders newsletter and join ~85,000+ readers and listeners worldwide!Miguel Armaza is Co-Founder and General Partner of Gilgamesh Ventures, a seed-stage investment fund focused on fintech in the Americas. He also hosts and writes the Fintech Leaders podcast and newsletter.Miguel on LinkedIn: https://bit.ly/3nKha4ZMiguel on Twitter: https://bit.ly/2Jb5oBcFintech Leaders Newsletter: https://bit.ly/3jWIpqp

Send us Fan MailMiguel Armaza sits down with Nikolay Seleznev, Co-Founder of Uzum, Uzbekistan’s first tech unicorn rewriting the playbook for e-commerce and fintech in Central Asia. From Moscow to Tashkent, Nikolay Seleznev brings global banking experience and entrepreneurial grit to a country leapfrogging straight into the digital economy.In this episode, Nikolay Seleznev shares the origin story of Uzum and how a simple, subpar online shopping experience sparked the vision for a super app serving millions. He dives into the challenges of building next-day delivery and financial services from scratch—without warehouses, 3PL infrastructure, or widespread digital adoption. Discover how Uzum managed to issue 4 million debit cards in a single year, reach 20 million monthly active users, and outperform their first-year GMV forecast by 4x, all while driving massive change in a historically cash-based society.Timestamped Overview00:00 Intro & Nikolay’s Background05:45 Building a Super App Ecosystem08:05 Time as the ultimate resource10:51 Uzbekistan’s rapid transformation15:13 Commerce and Fintech Ecosystem Overview20:12 Building trust through products23:15 Uzbekistan’s first unicorn funding26:57 Scaling success and adaptation28:22 Super app strategy adjustments32:02 Super Apps and Local Adaptation35:41 Self-focused entrepreneurial perspectiveWant more podcast episodes? Join me and follow Fintech Leaders today on Apple, Spotify, or your favorite podcast app for weekly conversations with today’s global leaders that will dominate the 21st century in fintech, business, and beyond.Do you prefer a written summary? Check out the Fintech Leaders newsletter and join ~85,000+ readers and listeners worldwide!Miguel Armaza is Co-Founder and General Partner of Gilgamesh Ventures, a seed-stage investment fund focused on fintech in the Americas. He also hosts and writes the Fintech Leaders podcast and newsletter.Miguel on LinkedIn: https://bit.ly/3nKha4ZMiguel on Twitter: https://bit.ly/2Jb5oBcFintech Leaders Newsletter: https://bit.ly/3jWIpqp