The Peel with Turner Novak

Jenny Fleiss, co-founder of Rent the Runway and Roll Rider, shares her journey creating a fashion rental revolution without a tech background. She dives into how social media fueled her startup and the importance of sustainability in fashion. Jenny discusses innovative fundraising methods using customer testimonials, the challenges of logistics, and her latest venture creating a scooter suitcase for families, demonstrating entrepreneurship alongside her kids. Plus, she shares her thoughts on AI's impact on e-commerce.

Daryna Kulya, Co-founder of OpenPhone and a startup marketing expert, shares her journey from Ukraine to building a successful business phone solution. She discusses innovative customer acquisition strategies using platforms like Facebook Groups and Reddit. Daryna emphasizes the importance of founder-led content and effective design in scaling to over 100k users. She also navigates the transition from free trials to paid models and the impactful role of customer feedback in developing their service.

Lisa Rapuano, a retired professional investor famous for beating the market for 15 consecutive years, shares insights from her remarkable journey. She discusses her early bets on companies like AOL, Dell, and Amazon, revealing key lessons from Jeff Bezos. Lisa emphasizes the importance of independent thinking in investing and contrasts practical and theoretical approaches to finance. She also highlights the significance of sound capital allocation while transitioning from investor to startup CFO, stressing the need for effective financial strategies and inclusivity in the finance industry.

Gokul Rajaram, an early-stage technology investor and product leader, shares invaluable insights from his time at iconic companies like Meta and Coinbase. He discusses lessons learned from titans like Zuck and Sergey Brin, emphasizing quick decision-making and defining your Ideal Customer Profile (ICP). Gokul also reveals why a bottoms-up approach to market sizing is essential and shares his hot takes on startup titles. Dive into the evolution of seed investing and the importance of responsiveness in shaping successful tech ventures.

Guy Podjarny, founder of Blaze, Snyk, and Tessl, discusses his journey in developer security and AI-native development. He shares his four quadrants framework for building AI startups and reveals why these ventures tend to be riskier. Guy dives into the challenges of hiring in tough markets, effective early marketing strategies, and the nuances of selling vs. building a company. He also reflects on lessons learned from Snyk's beginnings and highlights the importance of understanding customer needs for successful tech adoption.

Chris Hladczuk, Co-founder and CEO of Hanover, shares insights from his transformative journey in fund administration. He candidly discusses his shift from Goldman Sachs to tech, revealing strategies to build an impressive online presence. The conversation dives into the decline of traditional B2B SaaS, the underrated importance of sales and copywriting, and how to navigate the startup landscape effectively. Chris also emphasizes the role of a strong company culture, utilizing AI for productivity, and his unique approach to networking and client engagement.

Charley Ma and Mahdi Raza, co-founders of Pathlight Ventures and early employees at unicorns like Plaid and Robinhood, share invaluable insights from their journeys. They discuss the challenges of gaining initial customers, the significance of networking, and the importance of choosing between early and late-stage startups. The duo emphasizes the need for adaptability, discusses equity compensation intricacies, and reflects on their experiences conquering fears and uncertainties to build a successful venture fund in a tough economic landscape.

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.