Product Management in Founder-Led Startups with David Lifson: From Startup to Scale

In this episode, David Lifson shares his extensive experience in product management across different stages of company growth, including startups and major companies like Amazon and Etsy. Lifson discusses the challenges of being the first head of product for a first-time founder, emphasizing the importance of knowing what you're getting into and how it can be both a career-defining opportunity and a rollercoaster ride. He gives insights on founders' common traits, the pressures of early-stage startups, and the shift needed once a company reaches product-market fit. Lifson also touches on his journey from Amazon to Etsy, and founding his own company, providing valuable lessons on leadership, decision-making, product strategy, and the dynamics of working with founders. The conversation delves into practical advice for those considering head of product roles at startups, including setting realistic expectations, choosing battles, and understanding the real job you're being hired for.

00:00 Welcome to the SD Show: A Candid Chat with David Lifson

00:07 Navigating the Product Management Journey: Insights from Amazon to Etsy

01:26 The Harsh Realities of Being the First Head of Product

02:07 Traits of First-Time Founders: A Product Manager's Perspective

04:16 From Big Tech to Startup Life: David Lifson's Career Shift

06:52 The Founder's Imagination vs. Reality: Navigating Startup Challenges

08:11 Identifying Red Flags in Founding Stories

09:29 The Misconception of Product Market Fit

11:36 The Complex Dynamics of Founder Decisions and Team Impact

18:37 Evaluating Founders and the Importance of Trust

20:34 Reflecting on Success and Failure in Startups

23:10 Discovering Pregnancy Through Tech

23:44 The Value of Failure in Founding Teams

24:22 Debunking the 'Data-Driven' Myth

25:36 The Misuse of Data and A/B Testing

27:47 Navigating NPS and Ethical Dilemmas

31:16 The Role of a Founder in Product Strategy

34:39 Strategic Execution vs. Blind Action

37:48 Navigating Early Stage Product Leadership

39:55 Choosing Your Battles Wisely

42:54 Ethical Lines and Cultural Health

47:45 Working with Founders: A Multi-Layered Challenge

David Lifson's Bio: David Lifson has led high performing teams at startups, public, and private equity backed companies, delivering high impact outcomes through clear vision, validated product strategy, and collaborative culture. He’s gone 0 -> 1 multiple times, as well as led teams supporting $350M in revenue. His experience leading teams spans 15 years, including four as CEO/GM and eight as Head of Product & Engineering. Dave has a bachelors and masters degree in Computer Science from Cornell University, and is based in Austin, TX.