After 18 years leading Guidewire (~$10B), Marcus Ryu made the transition from CEO to partner at Battery Ventures. In the episode, Marcus shares his journey of co-founding Guidewire in 2001, steering the company through its IPO in 2012, and building one of the largest vertical software businesses in the world. He shares his insights on how to build a durable company in troubling times, what he looks for in entrepreneurs, the future of vertical software, and much more.

(00:00) Intro

(01:31) The Philosophical Approach to Investing and Strategy

(03:27) Unpacking the Strategy: Diagnosis, Market Definition, and Execution

(04:31) The Intricacies of Investment Decisions and Entrepreneurial Insight

(10:39) From Philosophy to Silicon Valley: A Personal Journey

(12:29) The Dot-com Bubble and Lessons Learned

(26:19) Guidewire's Founding: Identifying a Niche in the Insurance Industry

(37:13) The Early Days: Building from Scratch

(37:34) The Founder's Balance Sheet: Energy, Time, and Market Demand

(37:54) Starting with Nothing: The Humble Beginnings of a Startup

(38:14) The Power of Insight and Precision in Startup Success

(39:58) Product Development and Market Strategy: The Binder's Role

(40:37) The Brutal Reality of Go-to-Market: Rejection and Resilience

(42:59) The Parable of the Horse: Navigating Startup Highs and Lows

(45:23) Overcoming Legal Battles and Finding a Moral Purpose

(48:37) The CEO Transition: Learning from Leadership Changes

(50:49) Foundational Principles for Sustaining Founder Relationships

(53:41) Cultivating a Company Culture Based on Core Values

(01:01:31) The Journey from Founder to Investor: A New Chapter

(01:03:53) The Role of a Board and Achieving Founder-Investor Alignment

(01:08:25) Managing Founder Psychosis and Scaling as a Leader

(01:12:52) The Founder's Journey and Commitment

(01:13:27) The Philosophical Underpinnings of Insurance

(01:14:03) Insurance: A Civilizational Necessity

(01:15:01) The Impact of Insurance on Society and Innovation

(01:19:32) Navigating the Complexities of Insurance Regulation

(01:21:07) The Dark Side of Ad Tech and Its Societal Impact

(01:28:41) The Challenge of Communication and Leadership

(01:31:46) The Future of Software: Vertical Specialization

(01:42:05) Evaluating Founders and the Essence of Entrepreneurship

(01:45:56) Emerging Opportunities and the Specificity of Markets

(01:48:53) Concluding Reflections on Authentic Leadership

Executive Producer: Rashad Assir

Producer: Leah Clapper

Mixing and editing: Sam Dewees and JR Bohannon

Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA

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About the Show

Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes.