Clock Speed with Shamus Madan

Shamus Madan
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Aug 11, 2025 • 32min

How This Guy Bootstrapped A $6M ARR AI App

Josh Mohrer discusses the journey of developing the Wave app, sharing insights into its early development and the challenges faced, including combating copycats and acquiring users. He emphasizes the importance of overcoming skepticism with a strong work ethic and maintaining a work-life balance. The conversation delves into growth tactics, user acquisition costs, and leveraging Apple search ads. Josh offers entrepreneurial advice, highlighting the importance of speed in execution, idea selection, and key traits for entrepreneurs. He shares controversial opinions on business valuations, discusses stealth recording, and provides personal advice on patience. The episode concludes with lifestyle rules and a mention of the sponsor, Wave.co. Shamus Madan: 📩 Join The Dealroom: https://dealroompodcast.com/subscribe 🐦 Follow the host: https://x.com/shamusmadan Josh Mohrer 📱Check out Wave: https://wave.co/ 🐦 Follow the guest: https://x.com/joshmohrer (0:00) Introduction and Wave app insights (0:39) Early development and initial challenges (3:10) Combating copycats and user acquisition (5:33) Overcoming skepticism and hard work ethic (10:30) Work-life balance and growth tactics (12:53) User acquisition cost and Apple search ads (15:47) Entrepreneurial advice and speed in execution (19:33) Idea selection and entrepreneurial traits (24:09) Controversial opinions and business valuations (27:27) Stealth recording and personal patience advice (30:26) Personal tidbits and lifestyle rules (31:39) Episode closing and Sponsor: Wave.co
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Jul 24, 2025 • 46min

Meet The 28-Year-Old Who Built A $55 Million AI Startup in 18 Months

Joseph Krause shares his journey from leaving a PhD program to diving into entrepreneurship, drawing on lessons from his military service. He discusses his transition to Alley Corp and insights into venture capital, emphasizing the importance of convincing investors about the potential of material science. Joseph delves into building a successful company culture, leveraging AI, and identifying target customers. He outlines strategies for scrappy startup recruiting and raising $70M in funding. The conversation covers traits of successful entrepreneurs, handling failure, and running towards goals. Joseph offers advice for aspiring entrepreneurs, reflecting on discipline, maintaining focus, and embracing unsolved problems. Shamus Madan: 📩 Join The Dealroom: https://dealroompodcast.com/subscribe 🐦 Follow the host: https://x.com/shamusmadan Joseph Krause 📱Check out Radical AI: https://www.radical-ai.com/ 🐦 Follow the guest: https://www.linkedin.com/in/josephfkrause/ (0:00) Introduction and Joseph Krause's background (2:52) Leaving PhD for entrepreneurship (4:59) Lessons from military service to business (11:08) Transition to Alley Corp and venture capital insights (15:08) Convincing investors about material science potential (17:46) Building a successful company culture and team (21:09) Business model, AI leverage, and target customers (23:29) Startup recruiting strategies and scrappy beginnings (26:40) Raising $70M: Funding playbook (28:54) Vision and challenges for the future (32:40) The 51% rule and handling failure (34:33) Traits of successful entrepreneurs and overcoming failure (39:27) Motivations and running towards goals (40:09) Consolidated advice for aspiring entrepreneurs (42:09) Reflections to 20-year-old self and discipline (44:18) Maintaining focus and loving the process (45:06) Embracing unsolved problems and closing thoughts
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Jul 15, 2025 • 50min

Meet The 22 Year Old Making $150k Month From His Phone

Josh Suggs shares his entrepreneurial journey, starting with the founding of 203 Media and Tabs Chocolate. He discusses his transition from college to launching Study Buddy and overcoming initial challenges in NYC. Josh reflects on his decision to pursue entrepreneurship full-time while balancing college and business growth. He emphasizes the importance of commitment in scaling a business, transitioning from freelancing to leadership, and overcoming hiring challenges. The episode explores maintaining content quality, ambitions for 203 Media, daily routines, growth strategies, and achieving a six-figure month. Josh also discusses finding mentors, the power of hustle, and shares life advice and non-traditional approaches. Shamus Madan: 📩 Join The Dealroom: https://dealroompodcast.com/subscribe 🐦 Follow the host: https://x.com/shamusmadan Josh Suggs 📱Check out 203Media: https://www.the203media.com/ 🐦 Follow the guest: https://www.linkedin.com/in/josh-suggs-street-interview-ads-9912a3251/ (0:00) Josh Suggs' background and entrepreneurial journey with 203 Media (1:05) Influences and founding Tabs Chocolate (2:35) Transitioning from college to Study Buddy (4:00) Overcoming early challenges (6:33) Hustling in NYC and first successes (9:07) Decision to commit full-time to entrepreneurship (11:08) Balancing college with business growth (13:58) Scaling the business and the importance of commitment (20:22) From freelancing to business leadership (21:38) Building a team and overcoming hiring challenges (27:25) Maintaining content quality while scaling (29:16) Ambitions for 203 Media (32:01) Daily routines for success (34:26) Growth strategies and building business defensibility (35:44) Achieving the first six-figure month (37:57) Identifying new business verticals (40:02) Starting a business with limited resources (41:19) Finding mentors and talent (41:53) Best and worst advice received (46:18) One rule to live by and non-traditional approaches (49:17) The power of hustle and episode closing
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May 14, 2025 • 43min

Eli Cohen: How I Built A Multi-Million Dollar Business In My 20s

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 discusses financial success, bootstrapping, leveraging AI in marketing, and reflects on investments and failures, offering advice to his younger self and relating to non-entrepreneurs. Shamus Madan: 📩 Join The Dealroom: https://dealroompodcast.com/subscribe 🐦 Follow the host: https://x.com/shamusmadan Dan Porter 📱Check out OSMOS: https://www.osmos.co/ 🐦 Follow the guest: https://www.linkedin.com/in/eli-c/ (0:00) Introduction (0:08) Eli Cohen's journey from fintech venture to agency success (2:11) Overcoming early challenges and pivoting strategies (5:15) Rapid revenue growth and the role of partnerships (9:03) Value propositions and deal structuring for startups (12:23) Building a successful agency: Strategies and partnerships (15:13) Implementing processes, systems, and sales automation (18:56) The Hawk Method and scaling an agency (20:33) Learning from mistakes and persistence in sales (22:34) Mastering follow-up and client relationship management (25:34) Identifying signals to cease client pursuit (27:41) Agency growth through white labeling services (29:31) Insights on achieving financial success in your twenties (31:41) Bootstrapping a business and leveraging AI in marketing (36:09) Reflecting on best investments and learning from failures (38:09) Rejecting bad advice and cultivating a unique life philosophy (41:18) Understanding and relating to non-entrepreneurs (42:01) Advice to a younger self and closing thoughts
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Apr 7, 2025 • 47min

Overtime CEO: How I Sold My Business For $200M in 6 Weeks!

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. Shamus Madan: 📩 Join The Dealroom: https://dealroompodcast.com/subscribe 🐦 Follow the host: https://x.com/shamusmadan Dan Porter 📱Check out Overtime: https://overtime.tv 🐦 Follow the guest: https://www.linkedin.com/in/danporter (0:00) Introduction to Dan Porter (0:31) The success of Draw My Thing and entrepreneurial traits (0:58) Sponsor message (1:14) Selling a $200M company and user retention strategies (7:04) Balancing user experience with retention (9:33) Selling a business in six weeks (16:28) Changing your life's trajectory in a year (21:13) The power of storytelling in interviews and business (22:29) Employee rewards post-sale (23:33) Rehiring and giving back to employees (25:36) Lessons from industry icons (29:05) Professional sports league meetings insights (32:49) The art of storytelling and avoiding MBA hires (38:08) Life and negotiation advice (41:35) Reflecting on past choices and future aspirations (43:33) Networking and the value of authenticity (46:14) Closing remarks and sponsor mention
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Mar 18, 2025 • 34min

How This 20-Year-Old Built A $100k/Month Business From His Laptop

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, balancing freedom with accountability, and avoiding marketing misconceptions and trends. The episode concludes with Hamza's advice for young entrepreneurs and best practices for life. 🐦 Follow the host: https://x.com/shamusmadan 📩 Join The Dealroom: https://dealroompodcast.com/subscribe Follow the guest: https://x.com/HamzaAlsamraee Check out NewForm: https://newform.ai (0:00) Hamza Alsamraee's introduction and entrepreneurial journey (1:41) Transition to marketing agency and recognizing short form content (5:12) Acquiring first clients and sales strategies (9:08) Principles for creating effective ads and early success reflections (14:50) Insights on making the first $10-20k and sales insights (17:54) Overcoming business and personal challenges (20:35) Balancing life's demands and finding joy in work (22:45) Team dynamics: failure safety and balancing freedom with accountability (26:04) Marketing misconceptions and avoiding trends (28:38) Content opportunities and advice for young entrepreneurs (31:03) Life advice and best practices
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Feb 18, 2025 • 39min

I Asked A $2 Billion Investor For Advice

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 in a team, starting a company in the current market, and balancing long-term and short-term thinking in investments. Dan reflects on past decisions and offers guidance for aspiring venture capitalists. 🐦 Follow the host: https://x.com/shamusmadan 📩 Join The Dealroom: https://dealroompodcast.com/subscribe Follow the guest: https://www.linkedin.com/in/dan-ahrens-bb77a337/ Check out Left Lane Capital: https://www.leftlane.com/ (0:00) Introduction and background of Dan Ahrens (0:28) Traits of a great investor and advice for early career professionals (1:06) Influence of family on career choices (2:44) Common traits of successful individuals and the value of hustle (6:43) Founding LeftLane Capital and consumer market insights (10:24) The journey to raising a $630 million fund (13:00) Entrepreneurship and the role of age (15:09) Handling rejection and the value of thinking like an owner (17:02) Investment evaluation strategies (19:22) The importance of promoting from within and operating efficiently (22:53) Quick framework for evaluating new industries (23:43) Human-led sourcing in venture capital (27:06) Tips for overcoming career stagnation (29:22) Identifying key traits and A players in a team (31:47) Insights on starting a company in the current market (33:44) Reflecting on past decisions and advice to younger self (34:42) Balancing long-term and short-term thinking in investments (37:13) Guidance for aspiring venture capitalists
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Jan 28, 2025 • 27min

How A 23-Year-Old Built A $375 Million Business From Her Laptop

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 Follow the guest: https://x.com/alexavontobel Check out Inspired: https://www.inspiredcapital.com/ (0:00) Introduction to Alexa von Tobel and her entrepreneurial journey (0:36) Starting LearnVest during the Great Recession (2:07) Building LearnVest from Starbucks beginnings (4:32) Overcoming entrepreneurial challenges (7:23) Strategies for pitching to investors (10:26) Leveraging content to grow a business (15:59) Inside the acquisition by Northwestern Mutual (21:08) Reflections on sharing acquisition news with the team (22:49) Key advice and life rules from Alexa von Tobel (24:47) Discussing Inspired Capital's strategic goals (25:48) Exploring ambition and delusion in founders (26:41) Closing remarks and expressions of gratitude
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Jan 14, 2025 • 37min

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. 🐦 Follow the host: https://x.com/shamusmadan 📩 Join The Dealroom: https://dealroompodcast.com/subscribe Follow the guest: https://x.com/krishramineni Check out Fireflies: https://fireflies.ai (0:00) Introduction to Krish Ramineni and Fireflies origin story (1:09) Early career and lessons from Microsoft (2:14) Tips for college students on internships and creating opportunities (5:32) Journey from Microsoft to founding Fireflies (7:14) Overcoming financial hurdles in the early startup phase (10:49) Fireflies' pivotal shift to a meeting assistant product (13:29) Strategies for achieving viral growth (16:17) Key takeaways from mentor Vinod Khosla (18:22) Balancing purpose and profit in business (22:29) Work-life balance and personal happiness (23:30) Corporate bureaucracy vs. startup innovation (24:24) Building a lean and effective startup team (26:29) Unconventional wisdom for aspiring entrepreneurs (28:26) Traits of successful entrepreneurs and simplifying ideas (30:12) Leveraging AI in business opportunities (32:34) Learning from failures (34:25) Networking and advice for young entrepreneurs (37:11) Wrap-up and Sponsor: ${name}
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Dec 17, 2024 • 46min

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. 🐦 Follow the host: https://x.com/shamusmadan 📩 Join The Dealroom: https://dealroompodcast.com/subscribe Follow the guest: https://x.com/ankurnagpal Check out Carry: https://carry.com/ (0:00) Ankur Nagpal's journey to a million dollars through Facebook applications (0:32) Peter Thiel's tax strategy with founder shares in PayPal (2:46) Advice for college students and networking with industry leaders (5:29) Founding Teachable and its evolution (9:32) Building and scaling personal use products (10:11) Steps to scale Teachable's monthly recurring revenue and reverse engineering growth (16:37) Advice for founders feeling stuck and unique courses on Teachable (20:08) Teachable's acquisition offer and negotiation insights (25:13) Post-acquisition transition and new ventures (28:42) Investing and running a venture fund post-Teachable (30:02) Building new startups: Ocho and Carry (34:05) Key tax strategies for founders and real-life examples (37:53) Peter Thiel's Roth IRA strategy (39:45) Balancing CEO responsibilities and personal values (41:33) Best advice received and the importance of family connections (45:03) Advice to 18-year-old self and life reflections (46:10) Closing remarks and sponsor mention

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