Forward Thinking Founders

Mat Sherman
  • 5.0 (102)
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  • UPDATED WEEKLY

Forward Thinking Founders is a founder podcast where we interview high potential founders from networks like Y Combinator, The Thiel Fellowship, Product Hunt, Twitter, etc. and brings to light what they're building for the world. Think of it like the opposite of How I Built This, where we interview founders before they are successful, then if they are, we have a moment in time we can look back on in the early days. Does the model work? Look at our early interviews and you'll have your answer.

  1. 970 - Using your Voice To Complete Complex Workflows On Your Computer w/ Connor Waslo (Caddy)

    3D AGO

    970 - Using your Voice To Complete Complex Workflows On Your Computer w/ Connor Waslo (Caddy)

    Mat Sherman catches up with Connor Waslo, co-founder/CEO of Caddy, a desktop voice interface that keeps you in flow by turning spoken intent into real work across tools like Linear, Slack, Calendar, Gmail, and Notion. Connor shares the origin story with cofounder Rajiv, hard pivots, and craft standards for their private beta. They compare SF’s tech gravity with New York, reflect on learnings from Loom through acquisition, and talk about how YC’s time pressure reshapes execution from September to Demo Day. You’ll hear concrete use cases—function-key capture, automatic screenshots and tickets, calendar creation—plus takes on context, tone, and why video + AI is earlier, better, and scarier than most realize. They close with founder routines, community, and a billboard-ready reminder: who you work with matters most. Time Stamps:00:00 Introduction and Backstory: How Mat and Connor First Met   01:05 What Caddy Is and How It Works   03:15 The Origin Story: Loom Pain Points, Prototypes, and Pivot Hell   05:41 Lessons From Loom and Transitioning to Founder Life   08:25 Moving to SF for Y Combinator   09:53 SF vs. NYC: Tech Density and Culture   12:49 Inside YC: Speed, Pressure, and Company-Building   15:12 Building in a Fast-Moving AI World   16:59 Current Use Cases, Private Beta, and Product Direction   19:52 Long-Term Vision: Context, Tone, and the Future of Work   26:07 What’s Emerging in SF: AI Video and New Frontiers   28:15 A Day in the Life of a YC Founder   32:05 Launch Plans: Waitlist, Beta Access, and Community   34:00 The Billboard Question: Connor’s Final Message   36:08 Closing Thoughts ★ Support this podcast ★

    36 min
  2. 969 - The Marketplace Bringing Naps to Hotels w/ Jared Lerner (Nappr)

    4D AGO

    969 - The Marketplace Bringing Naps to Hotels w/ Jared Lerner (Nappr)

    In this episode of Forward Thinking Founders, Mat Sherman chats with Jared Lerner, co-founder and CEO of Nappr, a marketplace redefining hotel stays by letting travelers book rooms for short, flexible durations. Jared shares how his own struggles with sleep sparked the idea, what it takes to build trust with hotels, and how Napper attracts both travelers and partners. They dive into Napper’s booking experience, marketing approach, and the differences between building in New York versus San Francisco. Jared also teases what’s next — from expanding hotel partnerships to launching a consumer hosting platform. 00:00 Introduction to Nappr 02:28 Understanding the Nappr Experience 05:05 The Founding Story and Mission 07:56 Navigating the Booking Process 10:49 Marketing Strategies and Brand Awareness 12:57 The Startup Scene: New York vs. San Francisco 18:31 Future Growth and Expansion Plans ★ Support this podcast ★

    26 min
  3. 968 - Building Cursor for Mobile Apps W/ Mahdi Nouri (CatDoes)

    OCT 24

    968 - Building Cursor for Mobile Apps W/ Mahdi Nouri (CatDoes)

    In this episode of Forward Thinking Founders, Mat Sherman chats with Mahdi Nouri, co-founder and CEO of CatDoes, a no-code AI mobile app builder empowering anyone to create apps without writing code. Mahdi shares the story behind CatDoes, the product decisions that shaped its growth, and how he’s navigating the fast-changing AI landscape. They discuss what it takes to build a startup from Germany, how it compares to Silicon Valley, and why accessibility and user experience are central to CatDoes’ mission. Mahdi also offers a glimpse into the future of AI-powered app creation and how CatDoes is making software building radically easier for everyone. ★ Support this podcast ★

    28 min
  4. 967 - Controlling Your Phone With AI w/ Adam Cohen Hillel (Dafdef / AI Key)

    OCT 20

    967 - Controlling Your Phone With AI w/ Adam Cohen Hillel (Dafdef / AI Key)

    In this episode of Forward Thinking Founders, Mat Sherman interviews Adam Cohen Hillel, co-founder of Dafdef, the company behind AI Key—a groundbreaking device that plugs into your phone and allows AI to directly control it. Adam discusses the development journey of AI Key, the importance of privacy and security, and the potential future applications of their technology. The conversation highlights the intersection of personal AI and user experience, emphasizing the need for a consumer-friendly approach in a rapidly evolving tech landscape. 00:00 Introduction to DafDef and AI Key 04:44The Technology Behind AI Key 10:06 Development Journey and Background 16:52 Use Cases and Future Applications 26:28 Vision for the Future of Personal AI ★ Support this podcast ★

    36 min
  5. 966 - Building AI Copilots To Slow Down Human Aging W/ Nikhil Yadala (Healome)

    OCT 14

    966 - Building AI Copilots To Slow Down Human Aging W/ Nikhil Yadala (Healome)

    In this episode of Forward Thinking Founders, Mat Sherman talks with Nikhil Yadala, cofounder and CEO of Helome, a company building AI copilots to help people slow their aging. Nikhil shares how Helome uses advanced “aging clocks”, AI models trained on blood biomarkers, to measure biological age and guide people toward healthier, longer lives. We explore his decade-long journey from mathematician to longevity founder, why he believes measuring aging is harder than curing it, and how he built an open-source AI assistant called Longevity GPT to make personalized health insights accessible to anyone, anywhere. Nikhil also opens up about moving from India to San Francisco, what the Bay Area’s startup culture taught him, and his candid take on Brian Johnson’s Blueprint experiment. Topics covered: What biological age really meansThe science behind AI-powered aging clocksHow Helome helps people test and track longevity markersLessons from building in the longevity spaceWhy SF accelerates founders faster than anywhere else Learn more about Helome at helome.one and try Longevity GPT at asklongevitygpt.com. ★ Support this podcast ★

    32 min
  6. Building Infra for Private, Sovereign, and User-aligned AI Systems w/ Will Preble (Covenant)

    SEP 29

    Building Infra for Private, Sovereign, and User-aligned AI Systems w/ Will Preble (Covenant)

    In this episode, we dive into one of the most pressing conversations in technology today: the balance between innovation and security in artificial intelligence. The discussion with Will Preble of Covenant Labs unpacks why maintaining control over AI models is critical, the looming risks tied to data security, and the potential fallout of compromised systems. From the threat of economic instability to the need for transparency and collaboration, this episode explores the stakes of AI’s rapid rise. Key Takeaways: Control over AI models is essential for long-term stability.Data security remains one of the biggest vulnerabilities in AI.Hacking risks could have devastating economic consequences.OpenAI and similar technologies must be protected with robust safeguards.Compromised AI has the power to destabilize global markets.Society must better understand AI’s influence on our lives and economies.A delicate balance is needed between advancing innovation and ensuring security.Collaboration and transparency are crucial to building trust.Proactive strategies are necessary to reduce risks before they spiral. ★ Support this podcast ★

    35 min
  7. 964 - Cat Turner On Building Cursor for Complicated Billing Workflows (Autaly)

    SEP 15

    964 - Cat Turner On Building Cursor for Complicated Billing Workflows (Autaly)

    In this episode of Forward Thinking Founders, Mat Sherman interviews Cathleen Turner, founder of Autaly, a software company focused on improving logistics businesses by automating invoicing and cash flow management. Cathleen shares her unique journey into the logistics industry, the challenges faced by third-party logistics providers, and how Autaly addresses these issues. The conversation also touches on the importance of networking on platforms like X (formerly Twitter), the balance between work and personal life, and valuable lessons learned as a founder. ★ Support this podcast ★

    33 min
  8. Building a Dating App Powered by AI W/ Jonathan Liu (Cupidly)

    SEP 2

    Building a Dating App Powered by AI W/ Jonathan Liu (Cupidly)

    In this episode of Forward Thinking Founders, host Mat Sherman interviews Jonathan Liu, founder of Cupidly. They discuss Jonathan's journey from a young coder to a startup founder, his experiences with venture capital and bootstrapping, and the innovative AI dating assistant he created. Jonathan shares insights on building a personal brand on X (Twitter), strategies for going viral, and his vision for the future of dating technology. 00:00: Introduction to Jonathan Liu and Cupidly 02:09: The Journey of a Tech Founder 04:39: From Coding to Startups 09:08: The Evolution of Jonathan's Projects 10:28: The Shift from VC to Bootstrapping 11:37: Building a Personal Brand on X 13:23: The Viral Phenomenon of Eunice 16:23: Tips for Going Viral 18:38: Future Aspirations and the Dating Tech Landscape ★ Support this podcast ★

    30 min
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5
out of 5
102 Ratings

About

Forward Thinking Founders is a founder podcast where we interview high potential founders from networks like Y Combinator, The Thiel Fellowship, Product Hunt, Twitter, etc. and brings to light what they're building for the world. Think of it like the opposite of How I Built This, where we interview founders before they are successful, then if they are, we have a moment in time we can look back on in the early days. Does the model work? Look at our early interviews and you'll have your answer.

Information

  • Creator
    Mat Sherman
  • Years Active
    2019 - 2025
  • Episodes
    967
  • Rating
    Explicit
  • Copyright
    © Mat Sherman
  • Show Website
    Forward Thinking Founders