Eli Cohen shares his journey from fintech to agency success, highlighting early challenges, strategic pivots, and rapid revenue growth through partnerships. He explores value propositions, deal structuring, and building a thriving agency with effective systems and sales automation. Eli introduces the Hawk Method for scaling, emphasizing learning from mistakes and persistence. The episode covers mastering follow-up, knowing when to stop pursuing clients, and growing through white labeling. Eli di...
May 14, 2025•43 min•Ep. 141
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.
Apr 07, 2025•47 min•Ep. 140
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 navigating business and personal challenges while balancing life's demands and finding joy in work. He emphasizes the importance of team dynamics, balanc...
Mar 18, 2025•34 min•Ep. 139
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 efficiently. He provides insights on human-led sourcing in venture capital and overcoming career stagnation. The episode delves into identifying key traits i...
Feb 18, 2025•39 min•Ep. 138
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.
Jan 28, 2025•27 min•Ep. 137
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...
Jan 14, 2025•37 min•Ep. 136
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 strat...
Dec 17, 2024•46 min•Ep. 135
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 valu...
Dec 10, 2024•55 min•Ep. 134
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.
Nov 05, 2024•42 min•Ep. 133
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 a...
Oct 15, 2024•42 min•Ep. 132
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 su...
Sep 17, 2024•56 min•Ep. 131
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 fut...
Sep 03, 2024•39 min•Ep. 130
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 criti...
Aug 20, 2024•42 min•Ep. 129
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 con...
Jul 23, 2024•51 min•Ep. 128
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.
Jun 25, 2024•49 min•Ep. 127
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.
Jun 04, 2024•1 hr 4 min•Ep. 127
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.
May 07, 2024•47 min•Ep. 126
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.
Apr 09, 2024•52 min•Ep. 125
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.
Mar 26, 2024•51 min•Ep. 124
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.
Mar 12, 2024•58 min•Ep. 124
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.
Feb 27, 2024•52 min•Ep. 123
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.
Feb 13, 2024•51 min•Ep. 122
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.
Jan 30, 2024•29 min•Ep. 121
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.
Jan 16, 2024•40 min•Ep. 120
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.
Dec 12, 2023•25 min•Ep. 119
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.
Nov 30, 2023•39 min•Ep. 118
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 venture capital for Simple Closure.
Nov 09, 2023•37 min•Ep. 117
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 entrepreneurs.
Oct 26, 2023•22 min•Ep. 116
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 independence and personal growth.
Oct 12, 2023•30 min•Ep. 115
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 also explore the future of payment services and the impact of self-driving cars on ride-sharing. Emil offers advice for startups and shares about his ...
Sep 26, 2023•35 min•Ep. 114
