If you've been burned

Half the founders I get on Fit Calls start by telling me what already didn't work.

Author

Kara McMaster
April 28, 2026

Half the founders I get on Fit Calls start by telling me what already didn't work:

  • LinkedIn outreach that produced twelve conversations and zero deals

  • Cold email that went dark after four weeks

  • Paid ads that spent $8,000 to generate one MQL who ghosted

  • Three different agencies, each of which disappeared from Slack around month six

That story is so common I recorded a video specifically for founders who've been through it:

Kendra runs operations at a web development agency. Before we spoke, she had tried LinkedIn outreach on her own, cold email through a tool she'd bought twice, paid ads her last agency had run for ninety days with nothing to show, and three agencies she no longer has kind words for. She almost didn't take the call.


What had actually failed her was a generic playbook applied to a market that punishes generic playbooks. Web agencies sell high-trust retainers to buyers who have usually been burned by other agencies, which means the reader on the other end of any cold message is starting from a baseline of suspicion. The baseline of suspicion only cracks when the message is so specific that the reader assumes you must have already talked to someone on their team. Anything generic gets filed under "agency spam" in the first two lines.


Three months after we started, Kendra had three discovery calls in a single day and a $100K retainer sitting in her pipeline.

"We have a $100k deal in the pipeline thanks to Kara! Today I have 3 discovery calls. It's been a good while since we last had that. I'm very excited."

If your honest reaction to the word "outbound" is a small internal flinch, you're the reader this email is for.


One caveat. I say no to about half the founders who get on Fit Calls. This doesn't work if:

  • Pre-revenue or still validating whether people want what you sell

  • Under roughly $500K annual revenue (the setup fee would be a survival question, not a growth investment)

  • Counting on pipeline from us to cover next month's bills (cycle is three to ten weeks from setup to first booked conversations)

  • Weekly dashboards with color-coded charts are what you want from a partner

If none of that describes you and you're curious what a rebuild would look like for your market, forty-five minutes is forty-five minutes.

Kara