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Dalton + MichaelDalton + Michael

How Startups Close Million Dollar Deals

In this episode of Dalton + Michael, they discuss how founders can approach selling six- and seven-figure deals, even when they have no personal experience with deals of that size. Many founders default to building self-service products because those are the kinds of products they are used to buying. But for many startup ideas, limiting yourself to self-service can cap the size of the opportunity. Dalton and Michael talk through what it takes to sell bigger contracts, how founders can learn enterprise sales, and why closing large customers may be more approachable than it seems. Dalton + Michael is brought to you by @Standard_Cap Dalton Caldwell on X: https://x.com/daltonc Michael Seibel on X: https://x.com/mwseibel

Dalton CaldwellhostMichael Seibelhost
Jun 1, 202618mWatch on YouTube ↗

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  1. DC

    And so if you charge a similar amount as a startup, and it sort of resembles the way the other vendors charge, the customer will be like, "Oh, that makes sense." It'll fit right in.

  2. MS

    Yeah.

  3. DC

    Versus when you're a founder and you try to price it in a totally weird way.

  4. MS

    [laughs]

  5. DC

    It'd be like if you were-

  6. MS

    [laughs]

  7. DC

    ... if you were, like, a hotel, and you're like, "Oh, you pay with seashells." You know?

  8. MS

    Yeah.

  9. DC

    Like, "We don't take money here." [upbeat music]

  10. MS

    This is Dalton + Michael. Today we're gonna talk about how do startups get big deals, six-figure deals, seven-figure deals, eight-figure deals. How do they get big deals? And the kind of subtitle here is, are you selling tools or are you selling outcomes?

  11. DC

    I think a very common first office hour topic for companies that get accepted into YC is some version of them saying, "Dalton, how do I get big deal?" [laughs] You know, it's like, like they, they, they haven't even Googled it, right?

  12. MS

    Mm.

  13. DC

    This is just like a-

  14. MS

    [laughs]

  15. DC

    And I think the context is that most people understand self-service-

  16. MS

    Yes

  17. DC

    ... because they've signed up.

  18. MS

    Yes.

  19. DC

    Like, who hasn't signed up for GitHub or-

  20. MS

    Yes

  21. DC

    ... signed up for Figma or, you know?

  22. MS

    Yes.

  23. DC

    We're all used to signing up for SaaS-

  24. MS

    Yes

  25. DC

    ... putting in our credit card-

  26. MS

    Yes

  27. DC

    ... and paying for stuff. And so I don't think you'd need that much direction as a founder on how to create-

  28. MS

    How to charge $10 a month.

  29. DC

    Yeah.

  30. MS

    [laughs]

Episode duration: 18:12

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