20VC: The Largest Venture Backed D2C Consumer Exit; PillPack: $0-$300M Revenues in 5 Years & The Biggest Lessons Scaling the B2B Business to $300M in 2.5 Years with TJ Parker, Co-Founder @ PillPack
5th June 2023
Dylan Serota is the Founder & Chief Strategy Officer @ Terminal, the startup that helps you create world-class technical teams through remote operations as a service. They recently raised a phenomenal $13m Series A with some of the world’s most renowned names including Lightspeed, KPCB, Craft, Thiel, Atomic and Jerry Yang just to name a few. As for Dylan, he is also a Founder-in-Residence @ Atomic, one of the valley’s most exciting new institutions which both founds and funds companies and includes the likes of Hims, TalkIQ (acq by Dialpad) and more. Prior to Atomic and Terminal, Dylan was Head of Platform @ Eventbrite where he led platform product org, built third-party developer ecosystem and platform partnerships.
In Today’s Episode You Will Learn:
1.) How Dylan made his way into the world of startups with Eventbrite and how that led to his realisation on the future of development operations with Terminal?
2.) Why does Dylan believe that it is important for startups to build distributed teams earlier in their growth curve than often suggested? What are the key aspects to making remote teams work well? Why does Dylan believe that “companies overvalue their culture”? How does Dylan assess culture across remote teams?
3.) Jason lemkin says “startups can either hire a stretch VP or a burnt out mediocre VP”, does Dylan agree with this? How does Dylan assess the balance between hiring functional specialists vs jack of all trades? When is the right time to make the transition from generalist to specialist?
4.) Hw does Dylan analyze and assess a startup leaderships team ability to adapt and prioritize speed? What is key to successful decision-making today in startups? How does Dylan think about the importance of speed when it comes to product ideation and iteration?
5.) What does Dylan believe is the biggest mistake many people make early in their career? What are the commonalities of the truly successful people in how they have structured their careers? How does Dylan think about the balance between title vs salary vs experience? What should one optimise for and when?
Items Mentioned In Today’s Show:
Dylan’s Fave Book: The Selfish Gene by Richard Dawkins
As always you can follow Harry, The Twenty Minute VC and Dylan on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
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2nd June 2023