Date: 2026-08-03 Source: content - Blake Stewart
Signal
Blake met with strawberry.me, the team behind BetterHelp.com. They are replicating BetterHelp’s model for career coaches (career coaching marketplace). They are spending heavily on paid: $1M/month Meta, $500K/month Google, $250K/month podcasts. They are exploring newsletter advertising.
Blake is ready to send a proposal but paused to flag a potential competitive concern: strawberry.me’s business coaching service may compete with Rye Valley’s expert network (likely Hard Calls / JOLT context). Blake pinged Michael to review before sending.
Status
Resolved 2026-08-04: Michael reviewed the competitive concern and approved the K proposal (strawberry.me Sponsorship Approved).
Why It Matters
$1.75M/month in paid media = serious advertiser budget. If the competitive concern is not material, this is a high-value Hard Calls newsletter sponsor candidate. If it is material, worth knowing before a commercial relationship starts.
Action
Michael to decide: green-light the proposal or decline / adjust scope. No entry yet in the prospect pipeline.