The Dealroom with Shamus Madan

The Dealroom with Shamus Madan
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The Dealroom with Shamus Madan

Join Shamus Madan as he interviews industry leaders like Mark Cuban and Tim Draper, sharing insights on building billion-dollar businesses to inspire the next generation of entrepreneurs.

  1. 1 DAY AGO

    How A 20-Year-Old Started A Multi-Million Dollar AI Business

    Krish Ramineni joins the episode to share his entrepreneurial journey from Microsoft to founding Fireflies. He discusses the origins of Fireflies, its transformation into a meeting assistant product, and the strategies that fueled its viral growth. Krish offers insights on overcoming financial challenges in the early startup phase, balancing purpose and profit, and the importance of maintaining work-life balance. He contrasts corporate bureaucracy with startup innovation and emphasizes the value of building a lean team. The episode explores traits of successful entrepreneurs, leveraging AI, and learning from failures, with practical advice for young entrepreneurs seeking to create opportunities.

    37 min

  2. 2024-12-17

    Ankur Nagpal: Selling Teachable For $250 Million & Revealing Secret Tax Strategies

    Ankur Nagpal shares his entrepreneurial journey, from making his first million through Facebook applications to founding Teachable. He discusses the evolution of Teachable, scaling its revenue, and navigating its acquisition. Ankur offers advice for college students on networking and for founders feeling stuck. Post-acquisition, he delves into his new ventures, Ocho and Carry, and running a venture fund. The episode explores key tax strategies for founders, including Peter Thiel's Roth IRA strategy, and balancing CEO responsibilities with personal values. Ankur reflects on the best advice received, the importance of family connections, and offers wisdom to his 18-year-old self.

    46 min

  3. 2024-12-10

    Andy Dunn: How We Built Bonobos Into A $300 Million Business

    Andy Dunn joins the show to discuss the founding and growth of Bonobos, from its inception at Stanford to its acquisition by Walmart. He delves into the challenges faced with co-founder dynamics and the transition of CEO roles. Andy shares insights on raising initial funds, disrupting the men's pants market, and the importance of branding and customer service. He reflects on mental health struggles and the serendipitous Walmart deal. The episode explores lessons learned from dark times, the value of partnerships, and offers advice to his younger self. Andy emphasizes the importance of speed in execution, authenticity, and empathetic communication.

    55 min

  4. 2024-11-05

    How This 17-Year-Old Built A $1M/Month Business From His Laptop

    Zach Yadegari joins the show to discuss his journey from self-taught coder to successful entrepreneur. He shares how he sold his first company, Totally Science, for $100k, his new venture, Cal AI, and the tactics they've used to scale to seven-figures per month in revenue. Balancing education with entrepreneurship, he emphasizes bootstrapping and rapid idea validation. He reflects on the challenges and costs of being a young founder, learning from failures, and understanding distribution.

    42 min

  5. 2024-10-15

    I Asked A $1.5 Billion Investor For Advice

    Sean O'Sullivan shares his entrepreneurial journey, from not being able to afford food to selling his company for $15 Million at 28 years old. He discusses the traits of a great founder and offers advice for young entrepreneurs navigating today's market. Sean reflects on his early programming days and the founding of MapInfo at age 21, detailing the motivations behind the company and the challenges faced in scaling and going public. He explores the role of venture capital and his transition to active investing with SOSV, focusing on deep tech. The conversation delves into risks, the value of investing in first-time founders, and megatrends in manufacturing and climate tech.

    42 min

  6. 2024-09-17

    Anthony Pompliano: Turning $50k/Year Into $100 Million

    Join Anthony Pompliano and Shamus Madan as Anthony shares his journey from military service to entrepreneurship. He reflects on the impact of September 11th, handling pressure, and balancing ambition with practicality. The discussion covers business ideas for students, the book that changed his life, and Facebook frameworks that connect humanity in business. Anthony explores AI, overlooked opportunities, and insights from early Ethereum mining. He highlights common scaling mistakes, traits of successful billionaires, and offers advice to his younger self. Tune in for valuable lessons and insights from Anthony's experiences.

    56 min

  7. 2024-09-03

    This Ivy League Dropout Can Predict How You Might Die

    Kian Sadeghi shares his journey, beginning with a personal tragedy that inspired the creation of Nucleus. He explains the decreasing cost and increasing value of genome sequencing and his decision to drop out of UPenn to focus on build a biotech company. Kian shares the challenges he faced and the strategies he used to raise $18 Million from investors such as Alexis Ohanian. He highlights the advantages of being a young founder and demystifies genome sequencing. The conversation explores the future of genome data, its integration with personal hardware, and the hurdles in building consumer trust. Kian also reflects on the role of PhDs, the long-term vision for Nucleus, the lessons learned from failures, and how he manages stress.

    39 min

  8. 2024-08-20

    The Secret Behind Creating Viral Apps & Becoming The Youngest Intern at Tesla

    Dylan Diamond shares his entrepreneurial journey, starting with making websites in 4th grade to becoming Tesla's youngest intern at 17 to dropping out of UPenn to pursue building a company. He discusses his engineering background, early projects, and the creation and adoption of the Saturn app. Dylan balances his Tesla work with app development, meets co-founder Max, and reflects on early startup lessons. The conversation covers Saturn's growth, strategies, and challenges faced, as well as critiques of social media models and monetization strategies. Dylan concludes with key lessons from building Saturn, reflections on past failures, and personal advice.

    42 min
See All (137)

About

Join Shamus Madan as he interviews industry leaders like Mark Cuban and Tim Draper, sharing insights on building billion-dollar businesses to inspire the next generation of entrepreneurs.

Information

  • Creator
    The Dealroom with Shamus Madan
  • Years Active
    2021 - 2025
  • Episodes
    137
  • Rating
    Clean
  • Copyright
    © Copyright 2025 The Dealroom with Shamus Madan
  • Show Website
    The Dealroom with Shamus Madan

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