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Hey friends 👋
Ever had a big enterprise prospect come knocking and suddenly your entire startup strategy is up for debate?
Yeah, we see this all the time…
So this week we’re tackling the seductive allure of enterprise deals. You know the ones—big logos, bigger contract values, and that intoxicating feeling of “legitimacy.”
But it’s never that simple, is it?
Most enterprise plays are distractions dressed up as opportunities.
Long sales cycles (6-18 months vs. weeks), customization demands that kill repeatability, and the classic trap of pausing your working sales motion to chase a single whale.
We dive into three real-world scenarios in which founders are considering an enterprise pivot. From cybersecurity tools chasing Fortune 500 pilots to legal tech crushing it with small firms but tempted by big logos, we break down each move and rate it on our conviction scale.
Sometimes, selling to enterprise really is the right move. The key? Evidence over ego. Paid pilots over promises. And never, ever betting your last 11 months of runway on a sample size of one.
And then, Frivolous Thoughts:
* JDM finally finds his new EDC backpack (the near-perfect Simon Sinek Optimist bag from Solgaard).
* Cameron shares his Sacramento theater adventures with some unexpected horror movie tie-ins.
As always, thanks for listening.
—Cameron and JDM
