The Peel with Turner Novak

Zeb Evans, the Founder and CEO of ClickUp, shares his journey, influenced by six near-death experiences. He recounts early entrepreneurial ventures, including one that brought the FBI to his door, and lessons learned from his time at Disney. Zeb reveals how ClickUp bootstrapped to nearly $10 million in ARR, discusses hiring lessons while scaling to 800 employees, and highlights the importance of listening to user feedback. He also dives into ClickUp's product evolution and their recent chat feature launch.

Bobby DeSimone, the Founder and CEO of Pomerium, shares his insights on access control and security. He discusses the staggering impact of the biggest corporate hack and a breach caused by an unsecure air conditioner. Bobby reveals how Pomerium leverages an open-source approach for secure user access without a VPN. He highlights the failures of traditional security methods and the importance of a Zero Trust model. The conversation also touches on his journey as a technical founder and the pivotal lessons learned in enterprise sales and funding.

Tyler Denk, Co-founder and CEO of beehiiv, shares his journey from being the second employee at Morning Brew to building a successful newsletter platform. He discusses scaling to 3.5 million subscribers and the $75 million exit to Business Insider. Tyler reveals the secrets behind beehiiv’s rapid growth, including their unique no-meeting days and innovative product positioning. He also reflects on the challenges of remote team dynamics, a significant loss in his co-founding team, and lessons learned during unexpected crises.

Michelle Valentine, co-founder and CEO of Anrok, a sales tax compliance platform for software companies, shares invaluable insights on managing sales tax in a digital economy. She discusses the rapid evolution of software business models and offers tips for scaling companies while avoiding tax headaches. Michelle recounts her impressive experience raising Anrok's seed round in just 48 hours and provides advice on strategic hiring and customer acquisition. Dive into her thoughts on the unpredictable landscape of AI investments and how to leverage new technologies effectively.

Aaron Rubin, Founder and CEO of ShipHero, shares his entrepreneurial journey from nearly bankrupting his Jiu-Jitsu apparel brand to launching a $12B warehouse management system. He discusses the challenges of e-commerce, the misconceptions surrounding warehouse robotics, and critiques the 4PL model. Rubin highlights TikTok Shop's rapid growth, how companies like Temu and Shein navigate customs, and the critical importance of strategic hiring in business success. His insights blend personal anecdotes with industry expertise, revealing the grit behind innovation.

Logan Bartlett, a Managing Director at Redpoint and host of a well-known tech podcast, dives into fascinating topics. He shares insights on the origins of his podcast and how he navigated the web3 bubble. Logan discusses the importance of historical market cycles and data trends in AI, plus his advice for aspiring investors. He also reveals underrated investors and the value that VCs bring beyond capital, critiquing conventional investment philosophies. Expect humor and deep dives into the landscape of venture capital and startup investing!

Ryan Denehy, CEO of Electric, shares insights from his entrepreneurial journey. He reflects on selling his first startup to USA Today and facing financial struggles while launching Electric. Ryan emphasizes the importance of a clear sales pipeline and avoiding buzzwords in marketing. He discusses the challenges of solo founding and building a strong board, highlighting the impact of financing dynamics and the necessity of strategic hiring. Automation in IT management is also explored, showcasing how technology can simplify complex tasks for businesses.

Frank Rotman, Co-Founder and CIO of QED Investors, shares his journey from launching Capital One to shaping the fintech landscape. He discusses the evolution of financial services over 30 years, emphasizing customer-centric innovations. Rotman also analyzes crucial valuation strategies for emerging managers and the importance of understanding local markets when investing. He highlights the successes of Nubank and offers insightful advice on navigating the complexities of fintech and compliance in today's digital economy.

Yossi Levi, the visionary behind Car Dealership Guy, shares his journey from a family car lot to a $28 million business and founding Gettacar. Topics include innovative marketing strategies, hard lessons in product-market fit, and building a lean B2B media empire.

Guest Edwin Dorsey, author of The Bear Cave, discusses short selling, finding bad companies, using FOIA requests, corporate red flags, targeting minorities, and newsletter growth strategies. He shares insights on researching companies, exposing unethical practices, and leveraging customer sentiment. The podcast also explores short selling mechanics, customer sentiment impact on companies, insider selling significance, building newsletters, and exposing fraudulent practices in public companies.