20VC: Why Fundraising Is Like Dating and How to Play The Game Successfully & How To Increase The Flexibility of Your Burn When Growth is Ambiguous with Rachel Blumenthal, Founder & CEO @ Rockets of Awesome

Rachel Blumenthal is the Founder & CEO @ Rockets of Awesome, the startup that is reinventing the way parents shop for their kids clothes. To date, Rachel has raised over $19m in VC funding from the likes of Kirsten Green @ Forerunner, August Capital, General Catalyst, Gwyneth Paltrow and Female Founders Fund to name a few. Prior to Rockets of Awesome, Rachel founded fashion jewelry brand, Rachel Leigh. Rachel scaled the business to being available in over 300 stores worldwide and being named one of Oprah’s “Favourite Things”. Before that Rachel began her career in the publicity department at Yves Saint Lauren.

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In Today’s Episode You Will Learn:

1.) How Rachel went from founding a company that created one of Oprah’s “favourite things” to reinventing the way parents shop for their children today?

2.) Why does Rachel believe that “fundraising is like dating”? What does Rachel mean when she says “you have to play the game”? What does this literally look like in practice? What works in generating investor interest? What does not? Where does Rachel see many make mistakes in the fundraising process?

3.) How does Rachel think about capital efficiency with the evolution of her business? What tips and suggestions does Rachel give to increasing burn flexibility when future growth is ambiguous? Why does Rachel disagree with the thesis of raise money when you don’t need it? What length of time does Rachel believe is the right time to raise for?

4.) Rachel has said before that, “the best investors are operators”. What makes Rachel believe this? What are the drawbacks to operator VCs? What are the benefits to non-operator investors? What makes the truly special investor? How can a founder stress test this prior to their investment? What advice would Rachel give to a non-operator VC to improve their empathy and experience with founders?

5.) Rachel previous sly said to me that “being a woman in this male-dominated environment is everything the stereotype suggests”, what moment or story particularly resonates for Rachel when saying this? How did she respond? How can less confident first time minority founders respond in these situations?

Items Mentioned In Today’s Show:

Rachel’s Fave Book: Fast Company, Inc

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