Jan. 14, 2021

Lucy Deland (Inspired Capital) - Founding Paperless Post, How Design Became Critical To Software, and Why She's A Generalist Investor

Lucy Deland (Inspired Capital) - Founding Paperless Post, How Design Became Critical To Software, and Why She's A Generalist Investor

My guest today is Lucy Deland, Partner at Inspired Capital, who back early-stage founders with transformative ideas, brilliant teams, and relentless determination. Some of her investments include Geneva, Habi and Dandy.


A couple of books that inspired Lucy:

Amazing Grace by Jonathan Kozol

Why We Sleep by Matthew Walker.


Here's some questions I ask Lucy:

  1. Since you went from investor to founder to investor, where it makes sense to start is what attracted you to focus your career on technology and innovation?
  2. What was the insight that led you to founding Paperless Post?
  3. What led you to going back to your "roots" (so to speak) and become an investor again?
  4. Tell me a little bit about Inspired Capital and the formation.
  5. What were some of the lessons learned from your experience as COO that made you a better investor?
  6. I know that you're a generalist, but thesis driven. How do you approach which categories to focus on and opportunities?
  7. In our prior conversation, we spoke about some of the differences when your customer is a consumer, SMB and enterprise. When it comes to technology, IU, and feature set, depending on who you are selling to, what are your must haves?
  8. How has your due diligence process been disrupted by COVID?
  9. What are some of the different milestones a company has to have at the seed vs. series A?
  10. What are current trends (that are consumer facing) that you're focused on?
  11. What's one thing that you would change when it comes to venture capital?
  12. What's the best piece of advice that you received?
  13. What's one piece of advice that you have for founders?