Billion Dollar Moves™ with Sarah Chen-Spellings | Global Venture Capital cover art

Billion Dollar Moves™ with Sarah Chen-Spellings | Global Venture Capital

Billion Dollar Moves™ with Sarah Chen-Spellings | Global Venture Capital

By: Sarah Chen-Spellings
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Conversations with billionaires, unicorn founders, and the world’s leading funders. Hosted by Sarah Chen-Spellings, a global investor and entrepreneur, Billion Dollar Moves examines how enduring companies — and the capital behind them — are built. Through long-form conversations, the show explores decision-making under uncertainty, capital allocation, and the inflection points that shape category-defining businesses. From early platform backstories to allocator frameworks used across private markets, the focus is on judgment, incentives, and long-term value creation — beyond headlines and hype. New episodes weekly. Built for those who take the long view. Billion Dollar Moves is proud to be part of the Hubspot Podcast Network with 10 million downloads a month as a group.© Billion Dollar Moves™ with Sarah Chen-Spellings Economics Personal Finance
Episodes
  • How Midday Squares Is Building a Billion Dollar Brand Through Community, Chaos & Conviction | Jake Karls

    How Midday Squares Is Building a Billion Dollar Brand Through Community, Chaos & Conviction | Jake Karls
    May 28 2026
    In this final episode of Billion Dollar Moves for a bit, I sit down with Jake Karls, Co-Founder and Rainmaker of Midday Squares, for a candid conversation about building one of North America’s boldest founder-led consumer brands. Jake shares how he, his sister, and his brother-in-law went from making 50 bars a day in a Montreal condo kitchen to building an automated factory capable of producing more than 150,000 bars daily. We talk about why the co-founders committed to therapy from day one, how founder-led storytelling helped turn customers into a community, and why great marketing is not simply content—it is making people feel part of something. Jake also opens up about burnout, anxiety, his decision to step down as CMO, Midday Squares’ pivot beyond chocolate, and the work required to build a company that can eventually stand without its founders. For founders, funders, family businesses, and consumer investors, this is a conversation about trust, brand, resilience, and what it really takes to build for the long term. Watch the full conversation and subscribe for more discussions at the intersection of capital, leadership, and long-term value. 00:00 - Intro: Building something that can outlast you01:20 - Meet Jake Karls and Midday Squares02:15 - From a Montreal condo kitchen to 150,000 bars a day03:35 - Why build another snack brand?04:20 - Finding white space in a crowded market05:20 - Building a company with family06:00 - Why the co-founders committed to therapy07:15 - The two best investments they ever made08:00 - Communication as protection against founder conflict09:20 - Asking, “How are you really feeling?”10:00 - When the CEO stepped away for her mental health11:00 - Building structure without losing the soul12:05 - The product differentiation behind Midday Squares13:00 - The cocoa crisis that threatened the company14:00 - Betting on the no-bread PB&J pivot15:20 - The road from $40M to $100M16:00 - Why the founders work in three-year tours16:40 - Raising equity and government-backed debt17:15 - Scaling manufacturing without growing too fast19:00 - Building US retail distribution strategically20:00 - Why attention matters as much as product-market fit21:00 - Turning a snack company into a “band”22:00 - Why content is not marketing22:35 - How community helped Midday Squares break into Costco24:10 - Selling community, not just a product24:40 - Building a memorable founder persona26:00 - The roles each founder plays in the brand27:15 - Why Jake stepped down as CMO28:00 - Becoming the company’s Rainmaker29:00 - The risk of building a founder-led brand30:00 - Making the company less dependent on its founders30:30 - From anxiety and tears to trust in the team31:20 - Hiring people better than the founders32:30 - Building a brand that can stand on its own33:30 - Why overnight success often takes 10 to 20 years34:00 - Jake’s burnout and nervous breakdown35:40 - The warning signs he ignored36:20 - What recovery taught him about ambition36:45 - The Wall Street meeting that changed how he showed up38:15 - Authenticity, memorability, and having fun38:40 - Taste-testing the no-bread PB&J39:20 - Why the journey matters even if the outcome is uncertain39:55 - Final reflections from Billion Dollar Moves About Jake Karls Jake Karls is Co-Founder and Rainmaker of Midday Squares, a better-for-you snack company founded in Montreal alongside his sister, Lezlie Karls, and brother-in-law, Nick Saltarelli. The company began in a condo kitchen producing 50 bars a day and has since grown into a major North American consumer brand with a fully automated manufacturing facility, millions of customers, and ambitions to become a global afternoon snacking platform. Jake leads relationship-building, brand momentum, media, retail partnerships, and investor engagement. He is widely known for Midday Squares’ founder-led storytelling strategy and its unfiltered approach to documenting the realities of entrepreneurship. Billion Dollar Moves Podcast | The Top Global Venture & Business Podcast for Founders & Funders | Backed by HubSpot Podcast Network Conversations with billionaires, unicorn founders, and the world’s leading funders. Hosted by Sarah Chen-Spellings, Billion Dollar Moves examines how enduring companies—and the capital behind them—are built. Through long-form conversations, the show explores decision-making under uncertainty, capital allocation, and the inflection points that shape category-defining businesses. From early platform backstories to allocator frameworks used across private markets, the focus is on judgment, incentives, and long-term value creation—beyond headlines and hype. Built for those who take the long view. FOLLOW SARAH: Instagram: https://instagram.com/sarahchenglobal LinkedIn: https://linkedin.com/in/sarahchenglobal
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    41 mins
  • She Built a Billion-Dollar Company—Then Learned When to Walk Away | Suneera Madhani

    She Built a Billion-Dollar Company—Then Learned When to Walk Away | Suneera Madhani
    May 21 2026
    In this episode of Billion Dollar Moves, I sit down with Suneera Madhani, founder of Stax and Worth, for a candid conversation about building, scaling, exiting, and knowing when it is time to begin again. Suneera shares how a rejected idea became a billion-dollar payments company, why focus and customer obsession mattered more than any single formula, and what she learned from raising capital as a young Pakistani-American woman building outside Silicon Valley. We also talk about liquidity, private equity, rolling too much equity into a deal, losing control after a majority recap, and the difficult truth that a company can stop feeling like yours long before you officially leave. For founders, funders, and family offices, this is a conversation about conviction, ownership, wealth, and the discipline to know when to hold on—and when to let go. Watch the full conversation and subscribe for more discussions at the intersection of capital, leadership, and long-term wealth. 00:00 - Intro: Building, letting go, and a new chapter02:35 - Growing up in an immigrant entrepreneurial family04:40 - The confidence her father gave her07:25 - Risk, family expectations, and becoming a reluctant entrepreneur09:30 - The rejected idea that became Stax11:30 - Reinventing payments through a subscription model14:00 - Being laughed out of the room15:15 - Quitting her job and starting Fattmerchant16:20 - From $5M to $5B in payments17:00 - Building a memorable brand18:10 - From Fattmerchant to Stax21:10 - Scaling from $100M potential to a billion-dollar company22:00 - Why everything breaks as a company grows24:30 - Focus, customer obsession, and a winning culture26:15 - Raising capital as a minority woman founder27:30 - Scrappiness, rejection, and the first investor yes30:00 - Why she chose to build in Orlando31:35 - Preparing for an exit34:00 - Revenue growth and the majority recap35:30 - Selling at the height of the market36:00 - What founders get wrong about diligence38:15 - Creating a competitive private equity process39:00 - Choosing the right buyer40:30 - The deal terms she would rethink41:30 - Why she wishes she had taken more cash43:20 - The reality behind her exit44:00 - When the company stops feeling like yours46:00 - Why founders should sometimes sell and walk away47:10 - Building again after exit49:00 - Why Worth became the next fintech50:00 - Solving business credit and underwriting54:00 - Why onboarding is a revenue problem55:00 - Eliminating bias with better business data58:30 - The vision for the Worth wallet59:45 - Reaching $10M ARR in 18 months01:00:30 - Raising capital differently the second time01:01:00 - Rapid fire01:02:00 - Know your worth and take chips off the table01:02:35 - Why funding women is a billion-dollar move01:03:00 - CEO School and building the next generation of women-led companies About Suneera Madhani Suneera Madhani is a fintech entrepreneur, investor, and founder of Stax, a payments platform that reached unicorn status after processing tens of billions of dollars in transactions. After exiting Stax, she co-founded Worth, a financial technology company focused on modernizing business underwriting, onboarding, and credit intelligence. She is also the founder and host of CEO School, a platform and community supporting women entrepreneurs as they build, scale, and create wealth. Billion Dollar Moves Podcast | The Top Global Venture & Business Podcast for Founders & Funders | Backed by HubSpot Podcast Network Conversations with billionaires, unicorn founders, and the world’s leading funders. Hosted by Sarah Chen-Spellings, Billion Dollar Moves examines how enduring companies—and the capital behind them—are built. Through long-form conversations, the show explores decision-making under uncertainty, capital allocation, and the inflection points that shape category-defining businesses. From early platform backstories to allocator frameworks used across private markets, the focus is on judgment, incentives, and long-term value creation—beyond headlines and hype. New episodes weekly.Built for those who take the long view. PODCAST INFO:Podcast website: https://billiondollarmoves.comWatch on YouTube: https://tinyurl.com/sarahchenglobalJoin the community: https://sarah-chen.ck.page/billiondol... FOLLOW SARAH:Instagram: @sarahchenglobalLinkedIn: @sarahchenglobal
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    1 hr and 4 mins
  • From Preserving Wealth to Investing Globally | Erika Aquino on Billion Dollar Moves

    From Preserving Wealth to Investing Globally | Erika Aquino on Billion Dollar Moves
    May 14 2026
    Erika Aquino is a next-generation family office allocator and angel investor building on a Filipino family business legacy. In this episode of Billion Dollar Moves, Erika shares how her family moved beyond wealth preservation to deploy capital with purpose across wellness, education, sustainability, and the future of work. We discuss how she allocates to venture, why she prefers pre-seed and seed-stage companies, what she looks for in founders, and why proximity to the problem matters. Erika also speaks candidly about mental health, personal resilience, fiduciary responsibility, and the lessons she carries from supporting more than 25 early-stage companies around the world. 00:00 Introduction 01:00 Erika Aquino’s Family Legacy 03:00 Success as a Community Measure 04:10 From Wealth Preservation to Purpose 07:20 Allocating 25% to Venture 08:45 Building a Global Investment Mandate 09:35 Direct Investments vs. Funds 11:00 Why Erika Invests at Pre-Seed and Seed 11:35 Backing Scrappy Founders 13:00 Expanding Access to Angel Investing 14:00 Investing in Solutions Close to Home 15:15 What Erika Looks for in Founders 16:20 Building a Global Founder Ecosystem 17:30 Investing Across Different Markets 19:00 Fiduciary Duty and Venture Debt 20:20 Erika’s Mental Health Journey 23:10 How Personal Experience Shapes Her Investing 24:40 Supporting Underdog Founders 26:20 Advice for New Family Office Investors 28:20 The Role of Angel Investors 29:40 The Rise of the Modern Matriarch 31:00 Lessons on Money, Ambition, and Vulnerability 32:00 Own Your Confidence, Purpose, and NumbersAbout Erika Aquinohttps://www.erika-aquino.com/ -- Billion Dollar Moves Podcast | The Top Global Venture & Business Podcast for Founders & Funders | Backed by HubSpot Podcast Network Conversations with billionaires, unicorn founders, and the world’s leading funders. Hosted by Sarah Chen-Spellings, Billion Dollar Moves examines how enduring companies — and the capital behind them — are built. Through long-form conversations, the show explores decision-making under uncertainty, capital allocation, and the inflection points that shape category-defining businesses. From early platform backstories to allocator frameworks used across private markets, the focus is on judgment, incentives, and long-term value creation — beyond headlines and hype. New episodes weekly. Built for those who take the long view. PODCAST INFO: Podcast website: https://billiondollarmoves.com Watch on Youtube: https://tinyurl.com/sarahchenglobal Join the community: https://sarah-chen.ck.page/billiondol... FOLLOW SARAH: https://linkedin.com/in/sarahchenglobal https://instagram.com/sarahchenglobal
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    33 mins
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