Ep. 8
How to Sell like a Startup Founder with Jeremy Diamond

The Sales Conversation

Episode Overview

This episode features Jeremy Diamond, founder of the blog Startup Deck Review, which is dedicated to studying startup pitch decks. He has a rich media background and is an MBA graduate from the University of Washington Foster School of Business. In this episode we will be covering 3 key factors in a winning pitch, how to communicate your “Grit”, and advice for sellers in how to improve their selling conversations.

Episode Timestamps

[1:27] How Jeremy Got Focused on Helping Startups Master Their Pitch

  • Originally worked in TV production for Discovery and Animal Planet.
  • Decided to move to Seattle, get an MBA at the UW, and wanted to work for a tech company.
  • Worked for a startup that wanted someone who could think through things from a business perspective.
    • How he got into helping companies fundraise.

[3:55] 3 Key Factors in Driving a Winning Pitch

  • Their strong understanding of the customer problem that the founder has a mission to solve.
  • Their passion to solve the problem. Jeremy talks about their “marrying the problem”
  • Their grit. What any investor would be looking at in a founder of a startup:
    • What problem solving “grit” they have to bring to the market.
    • Investors want to know what they are investing in.

[9:58] “Grit” – the 3rd Factor

  • Grit is a subjective thing.
  • When investors are entering into a long relationship with people, they want to know that those people are going to be worthy of the money that they’re investing.
  • More unique to Venture Capital.

[11:09] Story on How a Founder Communicated “Grit”

  • Airbnb pitch deck
    • Founders sold commemorative cereal boxes during the 2008 election
    • Saw a desire path:
      • Recognized that certain data was not being understood by existing hospitality/lodging.
    • As an investor you’re asking these types of questions:
      • What was their character during that challenging time?
      • What sorts of actions did they take?
      • Were they creative in how they marketed and solved the problem?
      • Were they creative in how they operated their business?

[12:17] Communicating to your customer that you have the “Grit”

  • Making sure that the customers investment in you (your company/your solution) will be money well-spent.
  • Paul Smith: Story Telling for Sales
    • Different stories you can tell as a seller.

[13:33] Advice for Sellers

  • Social Proof.
  • Bring in traction:
    • Investors will argue.
  • Illustrate why your solution is better than the competition and how you’re going to compete.
  • Get and incorporate feedback into your pitch:
    • People like to help as long as they like to give constructive criticism and as long as you like to receive constructive criticism.
  • “Cold” Communication.

Additional Resources

Start Up Deck Review Blog
Jeremy’s Email
Airbnb Founder Grit Story at 20:47

If you have a pitch deck that you would like to suggest Jeremy to review, feel free to reach out!

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