What Should Founders Be Optimizing For? With Parker Conrad and Parker Thompson

Today's episode of Turpentine VC is a throwback to a conversation Erik Torenberg recorded with Parker Conrad and Parker Thompson that debates how much "value-add" investors can offer founders, issues around the misalignment between investors and founders, and the underdiscussed factors that influence VC deals. Parker Conrad is the co-founder and CEO of Rippling (and co-founder/CEO of Zenefits) and Parker Thompson is a current partner at SAX Capital (formerly Partner at Angellist). The conversation was recorded in 2018. Access global engineering without the headache and at a fraction of the cost: head to https://choosesquad.com and mention “Turpentine” to skip the waitlist.

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💥 Access global engineering without the headache and at a fraction of the cost: head to https://choosesquad.com and mention “Turpentine” to skip the waitlist.

This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co.

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RECOMMENDED PODCASTS: The 10x Capital Podcast

If you like Turpentine VC, check out our show The 10x Capital Podcast with David Weisburd, where David talks to the investors behind the investors: https://10xcapitalpodcast.com/.

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TIMESTAMPS:
(00:00) Intro
00:46 The Mystery of Startup Bill Jackson: Unraveling the Twitter Persona
(02:11) Investor Insights: The Good, The Bad, and The Ugly
(05:51) The Role of Investors: From Therapists to Strategists
(08:18) Brand Power and The Investor's Influence
(09:15) The Board Pleasing their LPs
(18:57)Navigating Founder-Investor Dynamics: A Real Talk
(19:28) The Seed Stage Perspective: Aligning with Founders
(26:07) The Boardroom Dilemma: Control, Influence, and Alignment
(36:44) Choosing the Right Investors: Lessons from Zenefits to Rippling
(37:01) Navigating Investor Relationships: Insights and Advice
(38:34) The Ideal Board Composition and Investor Dynamics
(39:22) Understanding VC Power and Protecting Your Company
(41:03) Real-world Challenges with Investors and Board Members
(42:51) Strategies for Entrepreneurs Facing Investor Pressure
(43:52) The Importance of Knowing Your VC's Business Model
(45:24) Raising Capital: Balancing Valuation and Partnership
(51:02) The Role of Unions and Standardization in Entrepreneurship
(54:33) Optimizing Fundraising Strategy for Long-term Success
(1:07:22) Closing Thoughts on Venture Capital Dynamics
(1:09:08) Wrap