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

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

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

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/
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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

Latasha Gillespie, former global executive at Amazon, shares how culture, customers, and risk were evaluated inside one of the world’s most powerful companies.

We discuss Amazon’s six-page decision process, what Latasha learned from Jeff Bezos, why diversity is a growth strategy, and how greenlight decisions determine which stories, audiences, and ideas are able to scale.

For founders, investors, and leaders, this is a conversation about reducing blind spots, protecting brand trust, and building for the customers of tomorrow.

TIMESTAMPS
00:00 Introduction
01:35 From Caterpillar to Amazon
03:35 The Career Lesson That Changed Everything
06:15 Diversity as a Growth Strategy
10:10 Tying Leadership Incentives to Outcomes
13:00 Knowing When It Was Time to Leave
15:10 Building Amazon’s Global Strategy
17:00 Presenting a Six-Page Memo to Jeff Bezos
19:00 Why Jeff Bezos Spoke Last
20:40 Building for Tomorrow’s Customers
22:20 Moving Into Amazon Studios
24:20 Where Power Sits in the Greenlight Process
29:00 Turning Values Into Systems
30:20 The Three Greenlight Questions
33:00 Identifying Reputational Risk
35:00 Media’s Role in Shaping Culture
37:00 Building Better Decision Frameworks
41:00 Leadership Lessons and Closing Advice

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About Latasha Gillespie
As Founder and CEO of Logos Media Group Holdings LLC, Latasha Gillespie leads a purpose-driven media holding company dedicated to creating impactful brands, platforms, and experiences at the intersection of faith, culture, and commerce. Through thoughtful storytelling, meaningful engagement, and strategic partnerships, the company aims to elevate culture while fostering connection and leadership across both digital and physical spaces.

With more than a decade of leadership experience in diversity, equity, and inclusion, along with expertise in business analysis, financial analysis, and project management, Latasha has contributed to global organizations including Amazon and Caterpillar. Her commitment to transformational leadership also extends to her service as an Executive Board Member of the Getty House Foundation, where she supports initiatives designed to create meaningful community impact.

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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

In this episode of Billion Dollar Moves, I sit down with David Berry, Co-Founder and Managing Partner of Averin Capital, for a conversation about building billion-dollar breakthroughs in healthcare.

David has founded more than 30 companies, including seven valued over $1B, and has helped shape companies across biotech, AI drug discovery, microbiome therapeutics, agriculture, and health infrastructure.

From losing a childhood friend to brain cancer, to asking why the hardest problems are worth pursuing, David shares how mission, science, and capital come together to create venture-scale healthcare companies.

For founders, funders, and family offices investing in the future of health, this is a conversation about conviction, ethics, and building for impact at scale.

Watch the full conversation and subscribe for more discussions at the intersection of capital, governance, and long-term wealth.

00:00 - Intro: Why go after the biggest problems?

01:12 - Truth vs. belief in science

03:00 - The myth that humans only use 10% of their brains

04:28 - Rethinking cancer and inherited assumptions

05:38 - How big ideas emerge from questioning “truth”

06:30 - Entrepreneur vs. investor: The N of one

08:10 - Building Seres Therapeutics and the microbiome frontier

11:00 - Turning strange science into a venture-scale company

12:20 - Why drug development does not always have to take 10–15 years

14:10 - Valo Health and AI-powered drug discovery

17:15 - Product-investor fit in biotech

20:30 - Why companies fail: Teams, resilience, and near-death moments

22:15 - Averin Capital and the transformation of health through technology

23:20 - BioLink and the future of continuous health monitoring

26:00 - Ozempic, access, and ethics in healthcare

31:10 - Women’s health, clinical trials, and bias in medical data

35:00 - David’s vision for Averin Capital

39:00 - How family offices should think about investing in health

40:00 - The next billion-dollar moves in healthcare

40:35 - Rapid fire

About David Berry

David is Co-Founder and Managing Partner at Averin. As an innovator and a company builder, he has been driven by the power of technology to transform industries. David has been a founder of over 30 companies, including 7 that have been valued at over $1B.

David was previously a General Partner at Flagship Pioneering. He was also founder and CEO of Valo Health, where he raised over $500M and executed a transformative partnership with Novo Nordisk.

David received his M.D. from Harvard Medical School and his Ph.D. from MIT through the biological engineering division, where he worked with Professors Robert Langer and Ram Sasisekharan. David works closely with Biolinq amongst other Averin companies.

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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/billiondollarmoves

FOLLOW SARAH:
https://linkedin.com/in/sarahchenglobal
https://instagram.com/sarahchenglobal
https://x.com/sarahchenglobal