Founder-Led Sales Arc

Lead-Lined Clothes

Connor Price shouldn't work on paper, and that's exactly why he does. On living your brand when the market pulls one way and who you are pulls the other.

Kevin OLeary··3 min read

I've been obsessed lately with a Canadian rapper who prays, adores his family, and turned down the machine to stay independent.

Connor Price shouldn't work on paper. Clean-cut Christian dad from Toronto, flowing with the swagger of the golden era I grew up on. For a kid raised on 90s rap and hip-hop, his style is timeless, and the contradiction is the whole point. He's not playing a character. He's standing all the way inside who he actually is, and you can hear it in every track.

Here's what nobody tells you about brand. Living it is the hardest work there is.

Writing the values down is easy, I've done it in an afternoon. The hard part shows up later, when the market pulls one way and who you are pulls the other, and you have to pick. Every founder hits a moment where living your values gives way to things like:

  • Softening an opinion because the consensus felt stacked against you
  • Pricing your product/services off something you found online or cloned from a competitor
  • Rejecting an epic hire because, as a new leader, you don't want to spend social capital convincing OGs that you know your stuff

Growing is scary. Doubt can feel like lead-lined clothes, heavy enough that standing still starts to look like wisdom.

Yet, when you figure out who you truly are, the path opens up. All that energy you were burning on the disguise goes back into the bigness that was in there the whole time. The exact thing you've been sanding down turns out to be the thing people came for.

Connor Price got big being exactly who he is, the family man with the vintage flow, and the more of himself he lets show, the bigger it gets.

He's been doing one thing since the small-venue days that tells you everything. There's a song called Buddy he made with Hoodie Allen, and at every tour stop he pre-picks a fan to come on stage and rap with him, live.

I watched it first at a 2k person venue and then again last month in front of nearly 10k. The young kid came up nervous, and when his first verse hit, the nerves fell away and the explosion of energy transported him into what I imagine was a living dream.

To say that this experience was legendary is to do it a disservice. Loudest the venue got all night, and it wasn't for the headliner.

That's the part nobody tells you about standing fully in who you are. The room it creates isn't just for you. Somewhere tonight that kid is carrying a moment that will live in his system forever, and it happened because one artist decided the realest version of his show had space for something different.

More than anything, this is an artifact of me (re)granting myself permission to be the most me version of myself, always.

Kevin OLeary

Written by

Kevin OLeary

Founder of Nicl. Twenty years in go-to-market. Writes about founder-led sales, AI-native GTM, and the referral co-op.

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