Hey friends 👋
This week's Office Hours brought the heat with some classic founder dilemmas that hit way too close to home.
Tuesday's solo session (Cameron’s still travelling) dug into pricing psychology and launch paralysis, while Friday's guest panel (featuring Ben and Rajiv) tackled everything from B2B discovery calls to marketplace liquidity.
And… Ben and I may have turned it into happy hour 🍻
Substack Session (Tuesday):
Three founders walked into a bar with pricing problems, launch delays, and investor ultimatums. We covered why $19/month might be signaling the wrong value, why "one more thing to fix" is killing your momentum, and why you should never let a single investor dictate your company's direction. The recurring theme? Stop optimizing for the wrong metrics.
Replay's above — hit play and dig in.
LinkedIn Session (Friday):
Quick hits from LinkedIn this week:
B2C Mobile App Pricing. When your investor says "show progress" before the next board meeting, it's usually code for "we're not seeing enough revenue signals." Focus on proving college students will actually pay for your solution, not just engage with it.
B2B Discovery vs Sales. You ran 30+ discovery calls but only got 3 pilots? You're mixing customer discovery with sales conversations. Stop asking if they "love the idea" and start uncovering their actual pain points and priorities.
Freemium Conversion Woes. Customers say they'd pay but won't commit? You're probably solving a problem that's not urgent enough or severe enough. Consider ditching freemium entirely and forcing everyone through a trial-to-paid model.
Waitlist Reality Check. 2000 people on your waitlist but only 50 convert to beta? That's not a waitlist problem, that's a targeting problem. You're getting tire-kickers, not serious customers.
Catch the replay and see how it all played out →
We’re live every week:
Tuesdays 9am PT on Substack
Fridays 12pm PT on LinkedIn
Bring your questions, your traction woes, your failed features — or submit ahead of time.
Want the full schedule? Check the calendar of upcoming Office Hours events →
—jdm
