In Depth
First Round
Welcome to In Depth, a new podcast from First Round Review that’s dedicated to surfacing the tactical advice founders and startup leaders need to grow their teams, their companies and themselves. Hosted by Brett Berson, a partner at First Round, In Depth will cover a lot of ground and a wide range of topics, from hiring executives and becoming a better manager, to the importance of storytelling inside of your organization. But every interview will hit the level of tactical depth where the very best advice is found. We hope you’ll join us. Subscribe to “In Depth” now and learn more at firstround.com
Episodes
Mentioned books
35 snips
Jul 24, 2025 • 1h 10min
What Braintrust got right about product-market fit | Ankur Goyal (Founder and CEO)
Ankur Goyal, Founder and CEO of Braintrust, shares his journey from dropping out of college to leading AI innovations. He discusses early lessons on software quality from MemSQL and the frustration that sparked Braintrust’s creation. Ankur reveals why they strategically delayed their market launch and dives into finding product-market fit in the AI landscape. He emphasizes that great software arises from a sense of 'paranoia,' highlighting the balance between skepticism and optimism in entrepreneurship.
42 snips
Jul 1, 2025 • 55min
How Gusto built a $9.5 billion company by identifying a burning problem
Tomer London, co-founder and Chief Product Officer at Gusto, discusses his journey from helping in his father's clothing store to building a $9.5 billion payroll platform. He emphasizes the importance of hiring for humility and embracing customer rejection as a path to innovation. London shares insights on conducting scrappy customer research and why emotional urgency is crucial for product development. He reveals how Gusto evolved from payroll solutions to a multi-product platform, focusing on creating tools that truly resonate with small business owners.
43 snips
Jun 19, 2025 • 1h 41min
How rejecting conventional wisdom grew Sentry to a $3 billion company | David Cramer (Co-founder and CPO)
David Cramer, Co-founder and CPO of Sentry, made his journey from high school dropout to tech entrepreneur, creating an open-source error monitoring tool used by 90,000 companies. He shares how a single code snippet evolved into a $3 billion business. Cramer highlights the underrated power of open source, his obsession with excellence, and the importance of connecting with customers. He also offers insights on rethinking marketing strategies and competitive dynamics in the tech space, emphasizing that challenging conventions can lead to monumental success.
94 snips
Jun 10, 2025 • 1h 33min
Inside Linear: Why craft and focus still win in product building | Karri Saarinen (Co-founder and CEO)
Karri Saarinen, Co-founder and CEO of Linear, shares fascinating insights from his tech journey. He discusses his early passion for computers, and crucial lessons from his first startup failure. Karri emphasizes the value of small, focused teams and the importance of validating product ideas through genuine user feedback. He also explores the role of Finnish culture in prioritizing quality over rapid growth, and the need for a clear design vision tailored to user needs. This conversation shines a light on the essence of creating impactful software.
124 snips
May 22, 2025 • 1h 20min
How Wes Kao coaches founders to influence, lead, and get what they want | Wes Kao (Executive coach, co-founder of Maven)
Wes Kao, an executive coach and co-founder of Maven and the AltMBA, shares insights into effective leadership and communication. She introduces her 'personality-message fit' framework, debunking myths around charisma. Wes emphasizes the significance of self-awareness and authenticity in communication. She explains how to navigate the complexities of founder-executive dynamics and addresses the importance of clarity in strategic thinking. With anecdotes on raising personal standards, this conversation is a masterclass in influence and self-expression.
May 8, 2025 • 1h 15min
From reluctant founder to $2B valuation: The story of Persona | Rick Song (Co-founder and CEO)
Rick Song, co-founder and CEO of Persona, shares insights from his journey transitioning from a secure role at Square to launching a game-changing identity verification platform. He discusses the importance of skepticism in shaping early strategies and explores the challenges of scaling in competitive markets. The conversation also highlights unexpected customer validations, evolving pricing strategies, and lessons learned from his co-founder. Rick emphasizes the critical nature of product-market fit in an AI-driven world and the value of strong partnerships in entrepreneurship.
66 snips
Apr 29, 2025 • 1h
How a weekend hack became a multimillion-dollar AI startup | Adit Abraham (Co-founder & CEO at Reducto)
Adit Abraham, co-founder and CEO of Reducto, previously a Product Manager at Google and a researcher at MIT's Media Lab, shares the journey of turning a weekend hack into a multimillion-dollar AI startup. He discusses how customer insights drove a pivotal business shift towards document processing. Adit reveals the strategies behind landing significant customers, including a Fortune 10 giant, and emphasizes the importance of genuine relationships in sales. With a successful $24M Series A under their belt, he offers candid advice for founders on navigating challenges and embracing failure.
6 snips
Apr 24, 2025 • 1h 8min
1Password’s growth story | How they went from bootstrapped to $6B company | Jeff Shiner (CEO)
Jeff Shiner, CEO of 1Password and former IBM executive, shares the journey of transforming a small, bootstrapped team into a $6B powerhouse. He explains why bootstrapping isn't always ideal and the logical leap to B2B solutions. Launching the product before billing proved successful, even as security measures almost hindered growth. Jeff reflects on the emotional rollercoaster of raising $200M in funding, the importance of user-centric design in security, and how true leadership is about supporting the team through challenges.
Mar 27, 2025 • 1h 23min
Scrappy tactics and a huge post-COVID pivot | Owner’s unconventional journey to product-market fit | Adam Guild (Co-founder and CEO of Owner)
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.
77 snips
Mar 6, 2025 • 60min
What makes (or breaks) executive hires | A deep dive with Eeke de Milliano (Head of Global Product at Stripe)
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.
