This is the $200M deal no one saw coming. Dan Porter was days from bankruptcy when a side project, Draw My Thing, became the #1 game in the world. Six weeks later, he sold his company for $200M. Then he did it again — founding Overtime, now valued at half a billion. This is how he changed his life in 12 months… and built a media empire from scratch…

Hamza Alsamraee shares his entrepreneurial journey, detailing his transition into the marketing agency world and the recognition of short-form content's potential. He discusses strategies for acquiring initial clients and principles for creating compelling ads, reflecting on early successes. Hamza offers insights on making the first $10-20k and nav…

Dan Ahrens shares his journey from family influences to founding Left Lane Capital and raising a $630 million fund. He discusses the traits of great investors and offers advice for early career professionals, emphasizing the value of hustle and thinking like an owner. Dan explores evaluating investments, promoting from within, and operating efficie…

At 23, Alexa von Tobel dropped out of Harvard to launch a financial education company, LearnVest, during the Great Recession. She put her life savings into starting the business. Years later, she sold it for $375 Million. This is her story. 🐦 Follow the host: https://x.com/shamusmadan 📩 Join The Dealroom: https://dealroompodcast.com/subscribe Follo…

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 purpos…

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 …

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 custo…

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 r…

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 th…

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…

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 invest…

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, me…

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 te…

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…

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.(0:00) Introduction(0:23) Gina's…

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. 🐦 Follow the host: https://twitter.com/shamusmadan 📩 …

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 …

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. Follow the host: https://twitter.com/shamusmadan 📩 Join The Dealr…

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. Follow the host: https://twitter.com/shamusmadan 📩 Join The Dealroom: https://dealroompodcast.com/subscribe Learn more about C…

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. Connect with Joe Lemay here: https://www.linkedin.com/in/lemayjoe/ Follow the host: https://…

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 a…

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. Meet Luc…

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. Not long after graduating from UC Berkeley, Noah became employee #30 at Facebook, where he …

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. It was the summer of 2004. Ben Van Leeuwen was looki…

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 i…

In this episode, Shamus Madan speaks with Dori Yona about his entrepreneurial journey, from his early ventures to the founding of Ernie. They discuss the challenges of shutting down a company, leading to the creation of Simple Closure, a solution that simplifies this process. Yona shares insights on customer acquisition, growth, and securing ventur…

In this episode, Shamus Madan talks to Ritwik Pavan about his journey from creating his first app, Flappy Yeeke, to establishing Linker Logic Technologies. They discuss Ritwik's transition to Vade, the inception of Krava, its role in addressing the housing crisis, and future goals. Ritwik shares his long-term vision and advice for aspiring entrepre…

In this episode, Shamus Madan interviews Kat Cole, discussing her early life, work experiences, and decision to drop out of college. They delve into overcoming stereotypes, imposter syndrome, and the challenges of being a young executive. The importance of financial education and self-love are also discussed, with Cole offering advice on independen…

In this episode, Shamus Madan talks with Emil Michael about the importance of mentors, his career journey post-Harvard, and his transition to the public sector. They discuss the shifting honor from public to private sector and Emil's experience at Uber, including its growth, international expansion challenges, and evolution into a 'SuperApp'. They …

In this episode, Shamus Madan interviews Hussein Fazal, discussing his entrepreneurial journey, the transition from bootstrapping to VC funding, and breaking into a duopolistic market. They also talk about Steph Curry's investment, remote work culture, and traits of successful entrepreneurs. The year is 2008. Hussein Fazal just quit his tech job to…

In this episode, Shamus Madan speaks with Jason Shuman about the challenges of entrepreneurship, from dealing with self-doubt to choosing business locations. They discuss strategies for building a strong VC network, the difficulties of raising capital, and how to handle business failure. The conversation wraps up with Jason's approach to seed inves…

In this episode, Shamus Madan chats with Bob Muglia about his career from early digital communication to Microsoft and beyond. They discuss startup expansion, cloud computing, AI, and the importance of focus and values in business. The conversation also delves into the future and risks of AI, societal implications, and Bob's book "The Data Pernoor.…

In this episode, Shamus Madan interviews Matt Higgins, discussing his journey from poverty to becoming the youngest press secretary in history. They delve into topics like self-reliance, the relationship between opportunity and data, and the importance of supportive partnerships. The conversation also touches on personal growth through depression, …

In this episode, Shamus Madan interviews Neil Blumenthal, co-founder of Warby Parker. They discuss Blumenthal's journey from Vision Spring to Warby Parker, the importance of customer experience, and the company's expansion strategies. They also delve into the future of glasses industry, Warby Parker's social impact, and key takeaways for entreprene…

In this episode, Shamus Madan converses with Ben Lamm about his journey from early life to becoming the founder of Colossus Biosciences. They discuss the company's mission, the inspiration behind it, and the challenges of biodiversity loss and raising funding. They also talk about balancing investor advice, the role of celebrity involvement, and de…

In this episode, Shamus Madan converses with Josh Felser about his entrepreneurial journey, the importance of pioneering in new technologies, and the role of AI in climate tech. They delve into Felser's leadership style, transition from entrepreneurship to venture capitalism, and the significance of investing in Climate Tech. The episode also touch…

In this episode, Shamus Madan chats with Courtney Reum, co-founder of M13. They discuss Courtney's journey from Goldman Sachs to entrepreneurship, the role of investment banking in business success, and the unique dynamics of founding a business with a family member. They delve into the concept of 'doing the impossible' in business, the transition …

In this episode, Shamus Madan talks to Mike Salguero about his entrepreneurial journey, from his early ventures to the birth and growth of ButcherBox. They discuss the impacts of venture capital, hiring strategies, and the future of meat consumption, concluding with advice for young adults. Let’s talk about entrepreneurship. Over the last few decad…

In this episode, Shamus Madan chats with Wes Kao about her early career, transition into entrepreneurship, and the role of Maven in online learning. They discuss the impact of COVID-19 on e-learning, the potential of solopreneurship, and the future of online education. Wes Kao is the Co-Founder of Maven, the platform for cohort-based courses. Prior…

In this episode, Shamus Madan interviews venture capitalist Maryanna Saenko. They discuss her journey from science and engineering to venture capital, the formation of Future Ventures, and their investment strategy in future tech companies. The conversation also explores the concept of winner-take-all markets, Saenko's interest in sustainable solut…

In this episode, Shamus Madan interviews Indus Khaitan, discussing his journey to Oracle, the challenges faced by immigrant entrepreneurs, and the importance of networking. They delve into Khaitan's role at Quollum, the customer acquisition process, and valuable advice for aspiring entrepreneurs. Indus Khaitan is the CEO of Quolum. He has over two …

In this episode, Shamus Madan converses with Noam Bardin about his tech journey and the creation of Post. They delve into comparisons between Post and TikTok, Post's business model, and its moderation policies. They discuss user engagement, verification processes, misinformation, and the community's role. The impact of social media on mental health…

In this episode, Shamus Madan talks with Oscar Muñoz about his journey from his grandmother's lessons to becoming the first Hispanic CEO of a major airline. They discuss Oscar's transition into the beverage industry, the role of mentors, strategies for turning around struggling companies, and the impact of personal health crises on his business dec…

In this episode, Shamus Madan engages with Matt MacInnis, discussing his journey from founding Inkling to his transition to Rippling. They delve into the concept of Rippling as a compound startup, misconceptions about such startups, and how to manage growth in economic tightening. They also touch on ethical layoff management and insights for future…

In this episode, Shamus Madan converses with ChatGPT-4 about the challenges in the current secondary education system. They delve into the role of AI in revolutionizing education, balancing automation with learning, and personalizing education using AI. They also discuss fostering critical and creative thinking and the need to prepare educators for…

In this episode, Shamus Madan interviews Adam Pritzker, discussing his unique business approach influenced by anthropology, the transition of General Assembly from a co-working space to an educational institution, and the role of culture, service, and values in business success. They also dive into the mission of Assemble Brands in the retail fashi…

In this episode, Shamus Madan talks with Heather Hartnett about her journey with Human Ventures. They delve into the tech ecosystem, discuss evaluating potential ventures, and share insights into their founder community. Heather also provides advice for aspiring fund managers, the role of hospitality in business, and the dynamics of social media. H…

In this episode, Shamus Madan interviews David Abney, former CEO of UPS. They discuss Abney's early career, the future of logistics with AI, and UPS's unique strategies like the right-turn policy. The conversation also covers the role of partnerships, acquisition strategies, key takeaways for future business leaders, and essential skills for succes…

In this episode, Shamus Madan talks with Brian Scudamore about his entrepreneurial journey, the expansion of The Rubbish Boys, and the role of franchising in business growth. They discuss Elon Musk's strategy of firing and rehiring employees, Brian's experiences on the Oprah and Ellen shows, and Shamus's podcasting journey. They also discuss handli…

In this episode, Shamus Madan interviews Brian Smith, founder of UGG. They delve into UGG's origin story and its connection to surfing, discuss the brand's growth phases and struggles, and explore the pivotal shift in UGG's advertising strategy. They also talk about the power of emotions in advertising, the challenges faced in Brian's entrepreneuri…