Parker Conrad has spent the last 8 years building Rippling into a $13B company, marking his redemption after being ousted from Zenefits. In his second appearance on the podcast, Parker and I discussed Paul Graham's "founder mode" essay and how he operationalizes it at Rippling. He also reflected on the key lessons he's learned throughout his career, highlighting the differences in how he ran Zenefits compared to Rippling today. Additionally, Parker shared his candid views on the challenges of having investors as board members and why he believes much of VC "value add" is overrated.

(00:00 ) Intro

(01:31 ) Parker's Leadership Principles at Rippling

(02:16 ) The Importance of Anecdotal Evidence

(04:09 ) Balancing Founder Mode and Team Collaboration

(05:08 ) The Risks of Over-Extrapolating Founder Mode

(06:56 ) The Reality of Sales Compensation

(08:15 ) Hiring Founders for New Products

(11:10 ) The Pace of Execution in a Company

(11:21 ) The 'C on a Box' Dilemma

(12:07 ) The Speed vs. Quality Debate

(13:56 ) The Viral Tweet Incident

(16:51 ) Governance and Board Dynamics

(20:04 ) Choosing the Right Investors

(29:57 ) The Role of Career VCs as Board Members

(33:43 ) Misaligned Incentives Between Founders and Investors

(35:43 ) Navigating Business Challenges

(36:27 ) Sam Altman's Crucial Support

(38:45 ) The Role of Venture Capitalists

(40:06 ) The Value of Y Combinator

(43:16 ) Fundraising and Valuations

(01:00:39 ) Lessons from Past Ventures

(01:06:05 ) Building Compound Software

(01:09:33 ) The Future of Compound Software Businesses

(01:10:04 ) Microsoft's Unassailable Approach

(01:10:40 ) Building Narrow vs. Compound Software

(01:12:16 ) Investment Decisions in New vs. Existing Products

(01:14:42 ) Platform Development and Resource Allocation

(01:16:32 ) The Journey from Chem Major to Software Visionary

(01:18:34 ) Challenges and Strategies in Multi-Product R&D

(01:25:32 ) Improving Customer Support Metrics

(01:28:50 ) The Role of a Founder in Product Management

(01:31:23 ) Hiring and Cultivating Executive Talent

(01:39:07 ) The Motivation Behind Rippling's Success

(01:41:58 ) Conclusion and Final Thoughts

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.