Hey friends 👋
You’ve got 43 customers using your product for free, a pilot converting at 4 out of 11, and a franchisor who just announced they’re building your product themselves—for free.
This week’s office hours was a live collision of founders at very different stages, all running into the same underlying problem: they’re optimizing for the wrong thing at the wrong time.
JDM and Cameron tackle five questions live from YouTube and LinkedIn:
a funeral home consolidator mid-pricing negotiation
a B2C wellness app chasing a launch before knowing who they’re selling to
a CrossFit gym SaaS getting sherlocked by its own franchisor
a baby sleep consultant product that discovered its pilot structure too late
a surf school booking tool trying to solve seasonality before it’s solved willingness to pay.
We break down enterprise pricing psychology, the trap of logo-hunting, why “stoned beach dudes” is not a customer segment problem, and how a transaction-based revenue model might untangle a seasonal billing headache.
We recorded in person again, the rain is visible through the window, Cameron’s deep into Justified, and JDM is watching Harrison Ford gracefully exit Shrinking.
And, as always, thanks for listening.
—Cameron and JDM
Timestamps
00:00 Intro
02:15 Live Q: When to hold firm vs. concede on pricing
10:30 Q2: Building momentum before MVP launch
20:00 Q3: Getting sherlocked by the franchisor
25:00 Q4: 4 out of 11 pilot conversions and what the split actually means
30:30 Q5: Union workers who don’t buy their own software
36:00 Q6: Seasonality, and when to charge
43:30 Frivolous Thoughts: the future of TV (which is now)
