Matt Kantor

My friend’s been out of work for almost a year.I had a coffee with him yesterday. We talked about his background and what he wanted to do.I suggested he try shifting more to marketingI took a sip of my too-small Cortado, and his reply - "I don't know anything about marketing".He was selling himself short - Shorter than my coffee.After 20 years in corporate communications, you likely know something about marketing. I'm sorry, its true.Often, you don't give yourself credit - as if you can only...

I used to work with a guy named D (I call him that here) — a great engineer, the type every startup quietly leans on when things get tough. He was T-shaped - he could work a bunch of different roles outside of their expected core. He built core infrastructure from day one. He could hang with the customer team or interview or design product features. He's a great guy to work with. But he was tired.Burned out.Quietly worn down by a role that no longer fit who he wanted to become. D dreamed of...

Imposter Syndrome Nearly Stalled My Life I knew my stuff. I still felt like a fraud. No matter what I built or shipped, that voice was always there. Not Good Enough. For years, imposter syndrome ran my life. And I didn’t even realize it. It showed up in small ways at first. I’d get stuck tweaking something to death — code, slides, specs, designs, even having a conversation. Chasing a version of “perfect” that didn’t exist. I’d say yes to every small project, terrified that saying no meant I...

“Too expensive,” Alana said. “And the name sucks.” We were eating oysters. I was showing her my new offer. It’s been 9 months since she could eat oysters. I walked her through the offer: the pricing, the positioning, the transformation. Six hours earlier, she said: “You’ve got 20 years of startup experience, decades of coaching + 3 years mastering LinkedIn from every angle. You know more about this platform than almost anyone. Wrap it in a bow. ” She was right.People are burned out on...

You know who never hesitates to ask for what they want?My kids. They’ll ask. Then ask again. Then keep going until you cave.They don’t take “no” personally.They just see it as part of the game. But most business owners avoid rejection like it’s contagious.We agonize over what to charge, how to pitch, whether we’re being “too much.” Why “No” Is Good for You I’ve started running an experiment: Collect 100 rejections a week Because when rejection becomes the goal, things change: You stop playing...

Automation Doesn’t Fix Broken Sales It just makes bad systems faster — and more expensive. Several months ago, I saw someone talking about building sales automation. “This GTM stuff is cool. If I automate outreach and follow-ups, I’ll save time and close more deals.” I was already testing out these tools so I understood the journey.. I didn't hear back - but I saw that his tagline and ICP had changed quite a bit. As someone who tends to keep adjusting until I get it right - I understood this...

It’s 1 AM, and in five hours, this newsletter goes out. An hour ago, my wife gave birth. In our bedroom. At 7 PM, the contractions started. I suggested we call the midwife. But the contractions were light. So my wife hesitated. So as a typical father, I did what any other birth partner would do. I asked ChatGPT what we should do. "GO NOW!" was the answer. Helpful? Sure. It didn’t ask for details. Getting more context would have been helpful. It didn’t check how far apart the contractions...