Un-Gatekeeping Sales
I've spent 15 years helping founders stop burning runway on sales strategies that were never meant for them. This is the stuff I wish someone had told them earlier. Real frameworks, for your stage.
getting to no
Most closing advice is about getting to yes. One of the best moves I know gets you to a "no" faster, and it makes the "yes" better.
I use it on calls all the time. Someone books time with me, tells me what they're working on, and I play back my understanding of their situation. Then I tell them w...
Oct 07, 2026
Fewer deals, more $$$
You've got 20 open deals. You're spending roughly the same amount of time on all 20.
A follow-up here, a check-in there, everyone gets a little bit of you every week. It feels like you’re staying on top of things. It feels like work. It also means your best deal and your worst deal are getting al...
Sep 23, 2026
Closed won (and you didn’t even know)
It's 5:58 AM and you're checking your phone before you're even fully awake.
Not for anything specific…you're checking to see if the prospect replied, if anyone sent the followup, if the demo is still on for today. If *all the things* are still in motion.
You have something real. Revenue is growi...
Sep 17, 2026
I didn’t know the rules, so I made them up
You know those people with clipboards trying to wave you down on the street? That was me in college.
Except I was going door-to-door in New York City. In apartment buildings, knocking on doors until someone asked how we got in there anyway?
Nobody really trained me on what a "normal" ask was sup...
Sep 10, 2026
Before you fire your new AE, read this
Six months ago you made your first real sales hire.
They had the right background, did well at their last company, maybe they said they had built some processes. Finally, someone to take deals off your plate so you can get back into other parts of the business!
But six months in, it’s not worki...
Aug 12, 2026
You trust 12 of your 47 open deals (be honest)
You have 47 deals in your pipeline. If you're honest, you'd bet money on maybe 12 of them.
The other 35 aren't deals (anymore). But you haven’t had that conversation with yourself yet.
A pipeline you don't trust doesn't only mess up your forecast. It lets you feel like you're fine when you're not...
Jul 29, 2026
I made the CTO look stupid (and lost $227K)
I lost a $227K deal because I made the CTO look stupid.
This was (obviously) not my plan. But... my whole pitch was built on how much better my product was than the system they were already running.
Slide after slide, I laid out everything that system couldn't do, everywhere it fell short, every ...
Jul 15, 2026
Before you scale the wrong thing
"We're at $4.5M. We want to hit $12M next year. Do we have the right team to get us there?"
This is how a founder started off a call with me recently.
On the surface, things looked fine. The sales team was closing deals. Revenue was growing. People were busy.
But when I started digging in, thing...
Jul 01, 2026
what if you're just growing?
A lot of entrepreneurs are people who have always been good at things.
That's why they go for big goals in the first place. They're highly capable. They know how to figure things out. They've been rewarded for this.
And then they start building a company.
And every single step asks them to do som...
Jun 17, 2026
you're not bad at hiring, you are bad at interviewing.
A few weeks ago I ran a final round interview for a senior enterprise sales role.
The candidate had over 10 years of experience…running an accessory brand. Never sold software. No experience in the industry whatsoever.
He had made it through four rounds of interviews to get to me.
Why? Because th...
May 07, 2026
why your deals keep slipping
You know the feeling.
You're 22 minutes into a sales team meeting and you are still on the first deal. Someone's gone down a rabbit hole. You realize you're not getting to the other 9 deals.
Or: you're in a 1:1 that turned into a meandering pipeline review (again).
Or: you're talking about the sa...
Apr 22, 2026
which game are you playing?
At the end of last year, a founder I know decided his company would be a failure if they didn't reach a $100M valuation in 2026.
They had about $2M in revenue.
It sounds dramatic, but this is the standard more and more founders are holding themselves to. 10X in Year 1, $100M by Year 3. Anything l...
Apr 08, 2026
Un-Gatekeeping Sales
