In this episode of Winners Welcome, we sit down with Deon Nicholas, founder and CEO of Espa AI, the AI executive assistant built for founders, operators, and anyone trying to achieve more. Before Espa, Deon founded Forethought, where he raised over $115M and became one of the earliest leaders in AI customer service, well before the current AI wave.Deon shares how he first got into AI as a high school intern in 2009, why he believes we're entering a consumer renaissance powered by agentic AI, and what he's seeing now that most people haven't caught onto yet. We also get into how he thinks about talent in the age of AI, the humility-confidence balance every founder needs, what it takes to build a personal brand as a technical founder, and why Espa is designed to make executive-level support accessible to everyone, not just the top 1%.Subscribe for more conversations with founders, operators, and investors building what's next.Our podcast is sponsored by Gunderson Dettmer #PoweredByGundersonTimestamps:0:00 Intro1:08 Raising $115M Pre-AI, Pre-Pandemic1:27 Discovering AI in High School in 20094:00 Building His First AI Learning Tool5:43 From Waterloo to Silicon Valley7:17 Why Customer Service Became the First Big AI Market9:38 Founding Forethought and Winning TechCrunch Disrupt10:40 The Aha Moment Behind Espa and Agentic AI13:38 How Deon Uses Espa Every Day15:51 Going Zero to One Again in a New AI Era17:55 Competitive Programming and the Roots of Grit22:40 How to Recruit World-Class Talent27:55 The Long-Term Vision for Espa30:28 Storytelling, Brand, and Becoming the Face of a Company33:43 Building an Authentic Personal Story as a Founder36:08 Where to Find EspaMore on Deon:https://www.linkedin.com/in/deon-nicholas/Check out Espa AI:https://espa.ai/More on Gabby:https://www.linkedin.com/in/gabriellecazeau/More on Brandon:https://harlem.capital/team/brandon-bryanthttps://www.youtube.com/@Wallstreetpaperhttps://x.com/wallstreetpaperThe Winners Welcome Podcast, by Harlem Capital, brings elite founders and top investors into thoughtful conversations on pushing past possible, sharing the conviction, standards, and lessons behind building generational companies.Harlem Capital is a venture capital firm that backs the next generation of winners. The firm partners with exceptional founders with the irrational motivation to build generational companies. All Winners Welcome.We’d love to hear from you. Share your feedback at [email protected] or DM us @HarlemCapital, and if you’re enjoying the podcast, please subscribe, rate, and review.

In this episode, Aman Mathur joins us to unpack how AI is reshaping the way software gets built. We talk about what’s changed inside Replit as the platform has scaled, why AI agents are lowering the barrier to creation, and what it takes to move from experimenting with prompts to actually shipping real products. The conversation also explores the future of software creation as design, development, and deployment become increasingly compressed into one workflow.Aman Mathur is a product leader at Replit, where he has helped drive the company’s product strategy during a period of rapid growth and major AI breakthroughs. Replit is building an AI-powered platform that helps anyone create and launch software faster, from first-time builders to large enterprise teams, with a broader mission of bringing the next generation of software creators online.Our podcast is sponsored by Gunderson Dettmer #PoweredByGundersonTimestamps:0:00 Intro1:04 Aman's Background and Replit's Growth2:00 From Education Tool to AI-Powered Platform3:47 Early Days at Replit: What Went Right and Wrong5:11 Who Is Building on Replit Today6:04 From Side Project to Revenue: The New Builder Economy6:40 The Agent Timeline: Agent 1 Through Agent 410:39 The Design Canvas Explained13:01 How the Agent Thinks: Context, Projects, and Outputs14:04 Enterprise Adoption and the Fortune 50016:43 The Pressure of Hypergrowth17:38 Replit's Operating Principles and Culture20:05 The Vision: A Billion Software Creators22:27 Building on Mobile: What's Possible From Your Phone26:22 What's Next for AI Agents in the Next 12 to 18 Months28:26 Advice for Builders: Just StartMore on Aman:https://www.linkedin.com/in/aman-mathur/More on Brandon:https://harlem.capital/team/brandon-bryanthttps://www.youtube.com/@Wallstreetpaperhttps://x.com/wallstreetpaperThe Winners Welcome Podcast, by Harlem Capital, brings elite founders and top investors into thoughtful conversations on pushing past possible, sharing the conviction, standards, and lessons behind building generational companies.Harlem Capital is a venture capital firm that backs the next generation of winners. The firm partners with exceptional founders with the irrational motivation to build generational companies. All Winners Welcome.We’d love to hear from you. Share your feedback at [email protected] or DM us @HarlemCapital, and if you’re enjoying the podcast, please subscribe, rate, and review.

Today’s conversation with Mitchell Jones covers what most founders miss: survival comes first. We unpack second-time founder advantages, fundraising psychology, and long-term trust with investors. And we go deep on why AI agents demand a new payments infrastructure.Mitchell Jones is a fintech founder building Lava Payments, a modern payments infrastructure company focused on enabling faster, more flexible capital movement for businesses. Before launching Lava Payments, Mitchell Jones co-founded Lendtable, a fintech platform designed to help employees access capital to participate in employer-sponsored benefit programs.Our podcast is sponsored by Gunderson Dettmer #PoweredByGundersonTimestamps:0:00 Intro1:00 Mitchell Jones’ Background and Founder Journey2:02 What Mitchell Learned From Building Lendtable6:41 The Three Biggest Founder Lessons From His First Startup8:24 The Pros and Cons of Being a Second-Time Founder13:19 Why Mitchell Is Building Lava and Betting on AI Payments18:57 How Lava Helps AI Companies Track Usage and Monetize20:27 Fundraising Advice: How to Think Like a VC25:17 What Really Gets an Investor to Say Yes29:44 Why Founders Should Pitch Believers, Not Convince Skeptics32:01 Why Trust Comes Before the Transaction35:24 Mitchell on AI Applications, AGI, and the Future of Companies41:18 Great Man Theory and the Future of AI44:40 OutroMore on Mitchell:https://www.linkedin.com/in/mitchell-jones-333559a2More on Brandon:https://harlem.capital/team/brandon-bryanthttps://www.youtube.com/@Wallstreetpaperhttps://x.com/wallstreetpaperThe Winners Welcome Podcast, by Harlem Capital, brings elite founders and top investors into thoughtful conversations on pushing past possible, sharing the conviction, standards, and lessons behind building generational companies.Harlem Capital is a venture capital firm that backs the next generation of winners. The firm partners with exceptional founders with the irrational motivation to build generational companies. All Winners Welcome.We’d love to hear from you. Share your feedback at [email protected] or DM us @HarlemCapital, and if you’re enjoying the podcast, please subscribe, rate, and review.

Today’s conversation with Kate Ryder explores what it takes to build a category-defining company in one of the most complex and regulated industries in the world, healthcare. We discuss scaling Maven into a $1.7B company serving over 28 million members globally, the role of timing, resilience, and storytelling in building generational businesses, and how AI is beginning to transform care delivery, operations, and patient outcomes. Kate Ryder is the Founder and CEO of Maven Clinic, the largest virtual clinic for women’s and family health. Under her leadership, Maven became the first unicorn in its category, partnering with over 2,000 organizations across 175+ countries to support fertility, maternity, pediatrics, and menopause through a modern, digital-first healthcare platform.

Our podcast is sponsored by Gunderson Dettmer #PoweredByGunderson

More on our guest:

https://www.linkedin.com/in/kate-ryder-87474933/

More on our host:

https://www.linkedin.com/in/jarrid-tingle/

The Winners Welcome Podcast, by Harlem Capital, brings elite founders and top investors into thoughtful conversations on pushing past possible, sharing the conviction, standards, and lessons behind building generational companies.

Harlem Capital is a venture capital firm that backs the next generation of winners. The firm partners with exceptional founders with the irrational motivation to build generational companies. All Winners Welcome.

We’d love to hear from you. Share your feedback at [email protected] or DM us @HarlemCapital, and if you’re enjoying the podcast, please subscribe, rate, and review.

Today’s conversation with Ryan Williams explores what it really takes to modernize a trillion-dollar asset class and build through cycles in one of the most competitive markets in the world. We discuss raising over $100M from top-tier investors, facilitating billions in real estate transactions, and the leadership, conviction, and resilience required to earn trust in private markets.

Ryan Williams is the Co-Founder of Cadre, a technology platform that has powered $5B+ in real estate transactions and helped redefine access to institutional-quality investments. He is known for his work at the intersection of fintech and real estate, bringing transparency, liquidity, and data-driven infrastructure to historically opaque markets.

Our podcast is sponsored by Gunderson Dettmer #PoweredByGunderson

More on our guest:https://www.linkedin.com/in/ryanawilliams1/

Today’s conversation with KJ Sidberry explores where we are in the AI super cycle and why consumer technology may be entering a new renaissance. We discuss how AI could reshape healthcare, education, play, and storytelling, and what Google Ventures looks for in the next generation of founders.

KJ Sidberry is a Partner at Google Ventures (GV), where he focuses on consumer and AI-native companies. Previously an investor at Forerunner Ventures, he’s known for his thoughtful perspectives on technology, culture, and the future of consumer products.

Our podcast is sponsored by Gunderson Dettmer #PoweredByGunderson

Timestamps:
0:00 Intro + why KJ is one of the top voices in consumer AI
1:52 Why consumer is due for a renaissance
3:28 How AI democratizes access in healthcare and therapy
5:18 AI should make us more human, not less human
8:03 Lessons from Oura Ring and the future of consumer hardware
12:45 Why wearable tech is becoming identity and status
13:42 How AI could transform education
16:56 Personalized learning and better employment outcomes
19:35 Alpha School, AI learning, and new education models
21:39 The future of play: AI toys, companions, and parenting
26:01 Why storytelling may be one of AI’s biggest categories
30:34 What Google Ventures looks for in founders
33:10 How GV supports founders after investing
34:19 Where we are in the AI super cycle
36:45 The behavior changes AI may already be driving
37:26 Why joy and delight matter more than productivity alone
38:31 Founder advice: build with velocity and scratch your own itch
41:40 Outro

More on KJ:
https://www.linkedin.com/in/kjsid/

More on Brandon:
https://harlem.capital/team/brandon-bryant
https://www.youtube.com/@Wallstreetpaper
https://x.com/wallstreetpaper

The Winners Welcome Podcast, by Harlem Capital, brings elite founders and top investors into thoughtful conversations on pushing past possible, sharing the conviction, standards, and lessons behind building generational companies.

Harlem Capital is a venture capital firm that backs the next generation of winners. The firm partners with exceptional founders with the irrational motivation to build generational companies. All Winners Welcome.

We’d love to hear from you. Share your feedback at [email protected] or DM us @HarlemCapital, and if you’re enjoying the podcast, please subscribe, rate, and review.

In this episode, Nicole DeTommaso speaks with Andrew Gazdecki, founder and CEO of Acquire.

Having built multiple startups, including one he bootstrapped to $10M in annual recurring revenue, Andrew founded Acquire to make acquisitions easier for startups across the globe.

Tune in as Nicole and Andrew discuss bootstrapping versus venture capital funding, building a brand through content and media, getting acquisition offers, and more.

In this episode, Nicole DeTommaso connects with Beezer Clarkson, Managing Director at Sapphire Partners.

With over 15 years of experience in venture capital, predominantly on the LP side, Beezer provides insights into what institutional LPs look for when evaluating emerging managers.

They discuss Sapphire's new $2 billion program focused on emerging VC managers in partnership with CalSTRS, as well as the importance of having an authentic investing strategy and portfolio construction.

Tune in for tangible advice for early-stage funds on positioning for success in a tougher fundraising environment.

In this episode, Nicole DeTommaso speaks with Ruben Harris, Founder and CEO of Career Karma.

Ruben started Career Karma in 2018 to provide career navigation technology to help people explore growth opportunities, and has now raised $52 million in funding and serves over 1 million people per month looking for career advice.

Tune in as Nicole and Ruben discuss how he utilized media like Twitter and podcasting to jumpstart his entrepreneurial career, build Career Karma's audience, and fundraise. They also talk about Ruben's approach to developing strong convictions as a founder and get his take on AI.

In this episode, Nicole DeTommaso chats with Elizabeth Yin, co-founder and General Partner at Hustle Fund, a venture capital firm aimed at democratizing wealth through startups.

They delve into the importance of having a niche in VC, Hustle Fund's unique approach to investment promotion, and their focus on post-pre-seed startups with proven product-market fit.

Discover how grassroots methods like cold emailing play a role in product testing and feedback, and learn about Hustle Fund's support for non-serial entrepreneurs and their global funding opportunities.