Clock Speed with Shamus Madan

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. 🐦 Follow the host: https://x.com/shamusmadan 📩 Join The Dealroom: https://dealroompodcast.com/subscribe Follow the guest: https://x.com/dunn Check out Pie: https://www.getpie.app/ (0:00) Introduction to Andy Dunn and Bonobos (0:26) Devastating news and cofounder challenges (0:39) Bonobos' journey from Stanford to Walmart acquisition (1:09) Bonobos' first year and Silicon Valley's early consumer internet (2:06) Brian Spaley's sales success and CEO transition (4:38) Shift in focus and private equity involvement (6:41) Raising initial funds and disrupting the men's pants market (11:45) Bonobos' growth and organic PR strategies (14:07) Branding and the importance of customer service (18:26) Speed in execution and tech misconceptions (22:35) Customer service stories and authenticity (26:07) Co-founder conflicts and empathetic communication (31:00) Mental health, depression, and coping mechanisms (36:28) Learning from dark times and the serendipity of the Walmart deal (49:46) Post-acquisition reflections and advice to younger self (53:51) The value of partnerships in entrepreneurship (55:06) Closing remarks and sponsor mention

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. 🐦 Follow the host: https://x.com/shamusmadan 📩 Join The Dealroom: https://dealroompodcast.com/subscribe Learn More About CalAI: https://apps.apple.com/us/app/cal-ai-calorie-tracker/id6480417616 (0:00) Introduction to Zach Yadegari and Totally Science (2:31) Zach's Self-Taught Coding Journey (4:01) The Impact of Totally Science's Popularity (5:59) Zach's Transition to the Startup World (7:40) Ambitions and Acquisition of Totally Science (11:04) Introduction to Cal AI and Its Functionality (13:39) Scaling Cal AI with Influencer Marketing (17:00) Balancing Entrepreneurship with Education (21:17) Bootstrapping and Rapid Idea Validation (24:28) Achieving Milestone Revenue at 17 (26:18) The Cost of Being a Young Founder (29:16) Learning from Failures and Understanding Distribution (32:07) Launching Viral Tech (33:42) Dealing with Failure and Privacy (36:45) Questionable Advice and Personal Rules (39:39) Zach's Advice to His Younger Self (41:16) Episode Outro

Sean O'Sullivan, a seasoned entrepreneur and the head of a $1.5 billion investment firm, shares his inspiring journey from struggling to make ends meet to selling his first company for $15 million at just 28. He discusses the key traits of successful founders and offers practical advice for navigating today's market. Sean reflects on his early days of programming and founding MapInfo, emphasizing innovative growth strategies. He also explores the significance of deep tech investments and the emerging megatrend of sustainability in manufacturing.

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. (0:00) Introduction and overview of Anthony Pompliano's experiences (0:19) Timeless advice and foundational principles (1:17) Impact of September 11th on Anthony's perspective and military motivation (5:53) Dealing with pressure in military and business (8:54) Early entrepreneurial ventures and lessons learned (10:55) Balancing ambition with practical constraints (14:09) Business ideas for college students and insights from Shamus's data collection (19:45) The book that changed Anthony's life and its continued impact (25:18) Frameworks learned at Facebook and connecting with humanity in business (29:59) The role of line striping businesses in future transportation and challenges in buying traditional businesses (38:26) AI, overlooked business opportunities, and earnings from early Ethereum mining (42:18) Common mistakes entrepreneurs make when scaling (44:40) Traits that separate hyper-successful billionaires from the average person and how to live an extraordinary life (51:14) Best investment ever made and greatest failure with lessons learned (54:17) Advice to 20-year-old self and closing remarks

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. 🐦 Follow the host: https://x.com/shamusmadan 📩 Join The Dealroom: https://dealroompodcast.com/subscribe Learn More About Nucleus Genomics: https://mynucleus.com/ Huge shout out to Savraj Singh for making this episode possible! (0:00) Kian Sadeghi's personal tragedy and the inspiration behind Nucleus (2:54) The decreasing cost and value of genome sequencing (6:10) Learning about human biology and the decision to drop out (10:49) Overcoming challenges and raising funds for Nucleus (14:57) Advantages of being a young founder and explaining genome sequencing (19:19) The future of genome data and integration with personal hardware (23:13) Building Nucleus: Challenges, consumer trust, and prioritizing tasks (31:12) The role of PhDs and the long-term vision for Nucleus (33:29) Learning from failures, current fears, and handling stress (36:09) Best and worst advice and reflections for the younger self

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. 🐦 Follow the host: https://x.com/shamusmadan 📩 Join The Dealroom: https://dealroompodcast.com/subscribe Learn More About Saturn: https://www.joinsaturn.com/ (0:00) Introduction and early success of Dylan Diamond (1:00) Dylan's journey from Tesla intern to dropping out (2:00) Dylan's background in engineering and early projects (5:04) The creation and adoption of the Saturn app (11:20) Balancing Tesla work with app development (16:32) Meeting co-founder Max and early startup lessons (19:30) The growth of Saturn and decision to pursue it full-time (23:19) Strategies for Saturn's growth and overcoming challenges (27:55) Critiquing social media models and Saturn's monetization (35:01) Key lessons from building Saturn and staying focused (38:47) Reflections on past failures and personal advice

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. 🐦 Follow the host: https://twitter.com/shamusmadan 📩 Join The Dealroom: https://dealroompodcast.com/subscribe Learn More About GreenPal: https://www.yourgreenpal.com/ (0:00) Introduction and early entrepreneurial experiences (2:45) Growth and scaling of the lawn mowing business to $10M (8:50) Lessons learned from selling the business (10:31) Transition to Green Powell and overcoming early challenges (15:57) Learning from failures and validating the business idea (21:03) Journey of learning software development (25:08) Transitioning to a tech platform and building a development team (29:29) Challenges and strategies in building a new marketplace (34:28) Monetizing Greenpal and content marketing strategies (43:55) Quick fire round and advice to younger self (50:14) Final thoughts on personal growth and compound interest (50:52) Sponsor: Green Powell

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. 🐦 Follow the host: https://twitter.com/shamusmadan 📩 Join The Dealroom: https://dealroompodcast.com/subscribe Learn More About Creme Digital: https://www.creme.digital/ (0:00) Jacob Klug: Early inspiration and first steps (1:12) Jacob Klug: Early entrepreneurial ventures (4:23) Jacob Klug: COVID-19 as a catalyst for business growth (10:11) Shamus Madan: College perspectives and decisions (16:30) Jacob Klug: Starting the no code agency with no capital (18:15) Jacob Klug: Strategies for acquiring initial clients (24:39) Shamus Madan: Managing a successful business at twenty (29:50) Shamus Madan: Future goals for the company (33:11) Jacob Klug: Learnings from building an agency (47:16) Jacob Klug: Advice to his sixteen-year-old self

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 pivotal career decision with Tumblr (1:14) Introduction of Gina Gotthilf (4:09) Gina's experience with a former boss who was a heroin addict (8:27) How Gina got the opportunity at Tumblr (12:17) The importance of networking for career growth (15:52) Trust and risk in startups (19:21) Common misconceptions about PR (34:52) Meeting President Obama: The White House demo day experience (45:56) Working with startup founders in Latin America: The story behind Latitude (53:45) Closing questions with Gina Gotthilf

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 📩 Join The Dealroom: https://dealroompodcast.com/subscribe Learn More About Chess.com: https://chess.com (0:00) Introduction to Eric Allebest and Chess.com (1:07) Early life and entrepreneurial journey of Erik Allebest (9:53) The realities of entrepreneurship and challenges of running a $100 million business (14:15) Erik Allebest on maintaining balance in entrepreneurship (20:12) Building a strong company culture in a remote setting and the founding story of Chess.com (26:20) Erik Allebest's growth strategies for Chess.com (34:27) Discussion on AI and cheating in online chess (39:17) The stresses of managing a growing company and reaching $100 million in revenue (43:31) Erik Allebest discusses his perspective on wealth and its impact on life choices (46:10) Erik Allebest shares what advice he would give to his younger self (47:08) Conclusion of the episode