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 ↗

EPISODE INFO

Released: June 1, 2026
Duration: 18m
Channel: Dalton + Michael
Watch on YouTube: ▶ Open ↗

EPISODE DESCRIPTION

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

SPEAKERS

Dalton Caldwell
host
Startup investor and Y Combinator partner focused on advising early-stage founders.
Michael Seibel
host
Y Combinator partner and longtime startup founder focused on company building and founder coaching.

EPISODE SUMMARY

In this episode of Dalton + Michael, featuring Dalton Caldwell and Michael Seibel, How Startups Close Million Dollar Deals explores how startups win million-dollar contracts by selling outcomes, not tools Big deals become possible when your pricing and packaging look familiar next to established vendors, so customers can evaluate you side-by-side without confusion.

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