This Week in Startups

Brian Halligan, Co-founder and CEO of HubSpot, dives into the wisdom garnered from scaling a leading inbound marketing platform. He shares how The Grateful Dead influenced HubSpot’s philosophy on customer experience and innovative marketing strategies. Halligan also reflects on evolving leadership strategies and managing a diverse workforce in the Glassdoor Era. He emphasizes the transformative power of introversion in tech and offers insights into creating exquisite customer interactions that drive success.

Alex MacCaw, CEO and co-founder of Clearbit, shares insights from his journey at notable companies like Twitter and Stripe. He discusses the power of data for marketers, especially through Clearbit X, which revolutionizes customer targeting. Alex emphasizes the necessity of prioritizing cash flow over high valuations and reflects on the implications of GDPR on tech giants like Facebook and Google. He also opens up about the transformative impact of CEO coaching on his leadership skills and the importance of mental health in the workplace.

Lidia Yan, CEO and co-founder of NEXT Trucking, is revolutionizing the industry with her two-sided marketplace focused on drayage. She shares her journey into trucking and the challenges faced as a woman entrepreneur. Lidia discusses how NEXT disrupts traditional brokerage systems, the impact of technology on pricing, and the industry's struggle with driver shortages. She also highlights the evolving role of e-commerce giants like Amazon and offers insights on achieving early profitability in startups.

Phil Libin, CEO of All Turtles and former Evernote head, introduces his innovative state machine theory that transforms startup growth strategies. Pete Flint, from NFX, shares insights on transitioning from founder to venture capitalist, while Rebecca Lynn of Canvas Ventures discusses early-stage VC dynamics and recruiting methods. Dave Samuel from Freestyle Capital talks about mentorship with founders, and Nate Smith, Lever's CTO, delves into effective hiring practices for startups.

Rahul Vohra, founder and CEO of Superhuman, shares innovative strategies for creating a 'Product-Market Fit Engine' in the email space. He emphasizes the challenge of transitioning to a paid model in a free market. The conversation includes insights from angel investors Jeff Clavier, Ben Ling, and Clara Brenner, discussing the current state of venture capital, the importance of early revenue, and how to ensure effective governance. Tim Thyne from Help Scout wraps up with tips on enhancing customer service to fuel business growth.

Tim Junio, CEO and co-founder of Expanse, a cybersecurity firm, shares insights from his time as a CIA analyst. He discusses the alarming trends of cyber threats, including Russian election interference and the vulnerabilities posed by unsecured IoT devices. Junio emphasizes the critical need for 'attack surface visibility' in large organizations and explores the implications of foreign infiltration in tech. He also raises optimism around cybersecurity advancements while highlighting the dangers of human error and the significance of strong password management.

Caroline Hansen, co-founder of Hubster, discusses fostering community through accessible outdoor games. Patrick O'Connor, from 3AM Innovations, unveils tech to enhance firefighter safety using real-time tracking. Michael Lee, CEO of Evolve Energy, shares insights on AI solutions to cut residential energy costs. Stonly Baptiste, co-founder of Urban.us, highlights the importance of city-centric startups. Together, they explore innovative solutions tackling waste reduction, traffic safety, and sustainable energy management.

Zander Lurie, CEO of SurveyMonkey, discusses the impact of customer and employee feedback on growth strategies. He shares insights on corporate governance lessons from WeWork, emphasizing the need for a diverse board. The conversation touches on direct listings versus IPOs and the significance of adapting to the evolving public market. Yosiat Gimbernard from Odoo joins to highlight how integrated business solutions can empower scalability, offering a fresh perspective on the modern business landscape.

Didier Elzinga, CEO and co-founder of Culture Amp, began his journey in visual effects before revolutionizing employee engagement with his platform. He discusses the pitfalls of traditional performance evaluations and emphasizes the need for ongoing feedback. Elzinga explores the evolving demands of modern employees, including work-life balance and innovative compensation models. He critiques Silicon Valley's approach to culture, advocating for genuine values over superficial perks. Listeners also gain insights into building trust through vulnerability in leadership and the significance of emotional connections in teams.

Aileen Lee, Founder and Managing Partner of Cowboy Ventures, has been a trailblazer in diversifying tech and VC. In this discussion, she shares her experiences confronting early gender bias in math and her journey from GAP to Silicon Valley. Aileen dives into the skewed funding landscape, highlighting the dangers of prioritizing growth over sustainability, particularly using WeWork as a case study. She offers insights from her investment in Dollar Shave Club and emphasizes the importance of diversity in the tech ecosystem, urging for stronger inclusion initiatives.