Un-Gatekeeping Sales Newsletter

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.

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

your best customers = the companies you've never heard of

In my first enterprise sales role, I’d spend over a year chasing logos. Maersk. Target. Walmart. Ralph Lauren. Home Depot. I’d get so excited about the potential with these companies and what it would mean for my startup to have them as a customer. Meanwhile, the deals that were closing every m...

Mar 13, 2026

does your outbound…compound?

Last month, a founder needed help generating more pipeline. I started by asking what they'd already been doing and what kind of results they were getting. They were running pretty consistent outbound campaigns to their ICP. Copy was decent, they were doing the work. And... the response rate wa...

Feb 25, 2026

it’s not them, it’s you

A founder booked a call with me last week. She mentioned they'd just let go of their second sales hire in 18 months and weren’t sure where to go next. "I keep hiring the wrong people," she said. "They had great backgrounds and have done this before. But they just... couldn't figure it out. Am I ...

Feb 11, 2026