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. -- SPONSORS: 🧲 Learn why Craft, Bedrock, NEA and 100s more trust Harmonic’s data to source deals. Harmonic is the most complete startup database, finding new companies as soon as they incorporate and tracking them through IPO. Head to https://bit.ly/harmonicturpentine (and make sure to mention Turpentine VC during your demo.) 💥 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 [email protected]. -- 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/. -- 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