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How Startups Close Million Dollar Deals

2026-06-01 · 16:37 UTC ·Dalton + Michael ·1 min read

Brief

Dalton Caldwell and Michael Seibel (Dalton + Michael) present a short presentation (published 2026-06-01) on how founders should pursue six- and seven-figure contracts instead of restricting themselves to self-service products. The hosts explain that enterprise sales skills can be learned, that self-service often limits ARR, and that moving to consultative/contract sales makes large deals more achievable; sponsor: Standard_Cap.

Why it matters

Dalton Caldwell and Michael Seibel (Dalton + Michael) — video published 2026-06-01 — argue founders can close six- and seven-figure deals even without prior enterprise experience by learning enterprise sales practices rather than defaulting to only self-service models.

Key details

  • They state that defaulting to self-service products can cap the total opportunity and recommend shifting toward consultative/contract sales to win larger contracts; episode is sponsored by Standard_Cap and includes links to Dalton and Michael on X.
Cleaned source text

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 Caldwell on X: https://x.com/daltonc

Michael Seibel on X: https://x.com/mwseibel

Channel: Dalton + Michael

Published: 2026-06-01

Video URL: https://www.youtube.com/watch?v=puOtyUD5qUo