In Depth

Adam Guild, co-founder and CEO of Owner, started his entrepreneurial journey with a successful Minecraft server before pivoting to help independent restaurants thrive. He shares how COVID-19 accelerated Owner's growth and the unconventional outbound strategies that drove customer engagement. Guild emphasizes the importance of emotional connection in retaining clients and discusses the qualities he seeks in new hires. His story highlights the evolution from early struggles to achieving product-market fit in the competitive restaurant tech landscape.

Eeke de Milliano, Head of Global Product at Stripe, shares her vast experience from roles at Retool and Constellate. She discusses the daunting challenges of executive hiring, pinpointing red flags and key qualities to look for in candidates. Eeke emphasizes the importance of aligning a new leader's vision with company values and offers practical advice for successful hiring. She also explores how introspection and understanding one's strengths can streamline the process, alongside valuable lessons learned from transitions between startups and established companies.

In this chat, Kevin Busque, co-founder and CEO of Guideline, shares his mission to transform 401(k) plans for small businesses. He discusses how his experiences at TaskRabbit revealed the pitfalls of traditional retirement systems and motivated him to create a user-friendly, transparent platform. The conversation dives into strategic partnerships, especially with Gusto, and the importance of customer feedback in developing their innovative services. Kevin's 'Do the hard thing first' mindset has been key to overcoming challenges and driving Guideline's impressive growth.

Bill Magnuson, co-founder and CEO of Braze, and Kevin Wang, CPO, share their incredible journey from a TechCrunch Hackathon to a $4.4B platform. They discuss insights on the mobile revolution and breaking traditional startup rules. The duo emphasizes the importance of first principles thinking and ethical data practices in tech development. They strategically navigate competition and adapt to market shifts, proving resilience is key in building meaningful customer relationships. Tune in for their fascinating take on growth and innovation!

Varun Anand, Co-founder and Head of Operations at Clay, shares insights from his journey in building a $1.25B startup that leverages data and AI for GTM innovations. He discusses transformative shifts to product-led growth, highlighting unconventional tactics like using WhatsApp and Reddit for outreach. Varun emphasizes the significance of hiring passionate individuals and strategic branding in a competitive tech landscape. He also advocates for unique compensation strategies to nurture talent and foster a culture that values personal contributions.

Tristan Handy, the Founder and CEO of dbt Labs, shares his journey of transforming a consultancy into a $4 billion cloud-based data platform. He reveals unexpected strategies for community building and driving software adoption after open-sourcing their tools. Tristan discusses the pivotal moment for seeking venture funding and emphasizes the importance of humility in creating a user-centric startup. He also touches on the impact of cloud technology on data analytics and the personal growth challenges faced in entrepreneurship.

Yuhki Yamashita, Chief Product Officer at Figma and former product leader at Uber, Google, and Microsoft, shares his insights on product design and storytelling. He discusses Figma’s evolution as a browser-based design tool and the importance of simple yet powerful products. Yuhki emphasizes the need for adaptability when transitioning from big tech to agile environments and the significance of storytelling in product development to engage users. His reflections on the dynamics of teamwork and nurturing taste highlight the journey from good to extraordinary product management.

Steve Blank, an Adjunct Professor at Stanford and expert in defense innovation, shares his insights on navigating the complexities of selling to the Department of Defense. He emphasizes the stark differences between commercial and military market strategies, detailing how startups can find mission solution fit. Steve discusses common pitfalls startups face and the significance of building key relationships in national security. He also highlights the transformation of Silicon Valley's attitude towards defense founders, offering fresh strategies for success in this unique sector.

Anneka Gupta, Chief Product Officer at Rubrik and former leader at LiveRamp, shares her insights from nearly two decades in tech. She reveals how LiveRamp skyrocketed from $30M to $200M ARR in just three years. Gupta discusses the balance between specialization and broad expertise, the significance of mentorship, and the complexities of migrating Fortune 500 clients post-acquisition. She also highlights the need for product managers to enhance their commercial sensibility and the value of diverse experiences in product leadership for effective decision-making.

Matt Lerner, Founder and CEO of SYSTM and author of "Growth Levers", shares insights on startup growth strategies that have propelled over 200 companies. He discusses identifying key growth drivers and emphasizes the importance of understanding customer needs through 'locksmith moments'. Matt uses case studies like Popsa to illustrate how acknowledging bottlenecks and effective messaging can boost growth. He also highlights the transition to a growth-focused mindset and the pivotal role of leadership in shaping successful organizational strategies.