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.

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.

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.

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.

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.

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.

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.

Meet The Founder Who Built The Uber of Lawncare

Bryan Clayton joins Shamus Madan to discuss his entrepreneurial journey, starting with his early experiences and scaling a lawn mowing business to $10M. Bryan shares insights from selling that business and transitioning to Greenpal, tackling early challenges and learning from failures. He details his journey into software development, building a tech platform, and forming a development team. Bryan also discusses the challenges of creating a new marketplace, monetizing Greenpal, and effective content marketing strategies. The episode concludes with a quick fire round, advice to his younger self, and final thoughts on personal growth and compound interest.

How This 20-Year-Old Built A $100k/Month Business With $0

Jacob Klug, a 20-year-old entrepreneur, embarked on a remarkable journey when he co-founded Creme Digital. At Creme, they specialize in creating beautiful software products at a fraction of the traditional cost and time. Their portfolio ranges from MVPs for startups to internal tools for Fortune 500 companies. What’s even more impressive? All their software is built using no-code tools like Bubble. This is the story of how he did it.

Meet The Marketing Genius Behind Duolingo's Viral Growth

Shamus Madan interviews Gina Gotthilf, covering her pivotal career decision with Tumblr, an unexpected experience with a former boss, and she grew Duolingo to 200M users with PR. They discuss trust and risk in startups, PR misconceptions, meeting President Obama, and her work with Latin American startups at Latitude.

Erik Allebest: How I Bootstrapped Chess.com To $100M in Revenue

In this episode, Shamus Madan interviews Chess.com's Erik Allebest about his entrepreneurial journey, the challenges of running a $100 million business, and maintaining balance. They delve into building company culture in a remote setting, growth strategies, and the impact of AI on online chess.

Casper Founder: How I Built A $575 Million Business At 31

When Neil Parikh was in medical school, he called his parents to say he was taking a year off to move to NYC. At the time, they were furious, but little did he know that would be one of the best decisions of his life. He partnered with his friend, whom he met at a coworking space, to build a DTC mattress company. Their most recent valuation was at over $1 Billion. This is the story of Casper and the secret behind their viral growth.

Sequoia Just Backed This Founder To Replace Advertising Forever

At just 12 years old, Sam Obletz decided to put his studies on the back burner and start a computer integration company with his friend. Today, he has come a long way from building computers and is now on a mission to change advertising forever. This is his multi-billion dollar plan.

Meet The $29 Million Founder Creating The Future of Education

The education system is broken, but Tade Oyerinde is on a mission to save it with his startup Campus. He raised tens of millions from Sam Altman, Dr. Shaquille O'Neal, and many others. This is his multi-billion dollar plan.

Joe Lemay: How We Went From -$400k To A $50 Million Exit Selling Reusable Notebooks

In 2016, Joe Lemay's balance sheet for Rocketbook was -$400k, and no VC would touch him. Bootstrapping was his only option. After four years of sweat and tears, he and his co-founder, Jake, built the company to a +$50M exit. This is the story of Rocketbook.

Bobby Brannigan: How I Went From $250k In Debt To Bootstrapping A $100M Business

In this episode, Shamus Madan chats with Bobby Brannigan about his entrepreneurial journey, from his father's grocery store to stock trading and textbook business. They discuss Bobby's innovative strategies, business financing, handling lawsuits, and market competition. Bobby shares his personal journey, including a life-changing backpacking trip and the influence of mentorship. The discussion ends with insights into scaling a business and Bobby's decision to sell his venture.

Lucie Basch: How I Co-Founded A Mobile App That Saved 300 Million Meals

In this episode, Shamus Madan chats with Lucie Basch about her fight against food waste, the creation and scaling of her platform, Too Good To Go. They discuss the economic and environmental impacts, onboarding challenges, international expansion, and the importance of a company's story. Lucie also shares advice for aspiring entrepreneurs.

Noah Kagan: Revealing The Marketing Strategy I Used To Build A $100M Business

In this episode, Shamus Madan converses with Noah Kagan about his journey from his early marketing experiences to his time at Facebook and Mint. They discuss 'Test and Invest', a strategy used by AppSumo, and Noah shares advice he'd give to his younger self.

Ben Van Leeuwen: How I Founded A $300k/Day Business Selling Ice Cream At 24-Years-Old

In this episode, Shamus Madan talks with Ben Van Leeuwen about his journey in the ice cream industry, starting a business with limited capital, and building a positive culture. They discuss hiring strategies, finding capital for growth, overcoming challenges, and the reality of overnight success.

Matt Chan: How I Bootstrapped a $40k/Month Lead Generation Agency In Six Months

In this episode, Shamus Madan converses with Matt Chan about his entrepreneurial journey. They discuss Matt's transition to entrepreneurship with Alpine Media, his experiences in agency work, and how he ventured into the pool building industry. Matt shares his encounters with personal challenges, including a robbery in Greece, and how he overcame initial failures. The episode concludes with his insights on goal setting, team building, and refining the sales process.