Want me in your ear instead? Hit “Listen Online” at the top of this email.

I told a founder to change everything.

New VP of Sales. New VP of Marketing. Double ad spend. All in the same quarter.

She left our conversations confident.

Fast forward a few months… She's not so sure anymore.

The company was at an inflection point.

The old marketing leader was heading out. They needed a new VP of Sales. They were also evaluating a VP of Marketing.

The instinct (and the instinct of any spreadsheet you'd build to model the decision) was to stagger the two hires. Bring on the sales leader first. Let him ramp for 6 months. Get a little revenue growth. Add the marketing hire later when the cost feels safer. Pull back ad spend to be “cautious” of budget.

I recommended the opposite. Stack both at once. Hit the gas.

The founder’s response: "I'm not 100% sure we've got the cash."

I asked directly whether she had three or six months of runway to cover roughly $200k in additional salary. She said "we have enough." But "enough" with a question mark.

She was being responsible, not timid.

Revenue had been stale for months. I was asking her to stack two senior salaries on top of a marketing function that was mid-rebuild. There was no outside board. The savings were hers. If this didn't work, the consequences weren't going to land on a CFO or a venture fund. They were going to land on a kitchen table.

Most founders I work with hit a version of this moment. The model is changing, the team is changing alongside it, and the bank account is the only thing left that feels stable enough to make decisions from.

Then the bank account says, “Excuse me, you’re asking to add $1M+ this year in expenses with no additional revenue to cover it yet?”

She was right to be nervous.

Three reasons I told this founder to push forward.

1. She was doing the affordability math against the wrong company.

Revenue is a lagging indicator.

What hits your bank account today is the result of decisions you made 90 days ago. Sometimes longer.

Which means when she was looking at her cash position and asking whether she could afford the new hires, she was calculating what the old company could afford while paying for what the new company would produce. Past funding future.

The gap between “past ops” and “future ops” always feels like failure. In reality, it's just the transition running its course.

2. A VP of Sales with no pipeline isn't a VP of Sales.

Hire him alone, ahead of the marketing leader, and he walks in to an empty pipeline. His first 90 days don't get spent closing. They get spent manufacturing pipeline—or wondering if he made the right choice joining the ranks. He becomes a marketer with a quota. By the time real leads are landing, he's 6 months in and hasn't done the job you hired him for. Now you’re wondering if he was the right hire.

They couldn’t ease on ad spend during the transition either. Load the pipeline first. Let the marketing leader build the funnel. Then the sales leader has something he can actually close on Day 1.

3. Staggering hires doesn't halve the cost. It doubles the duration.

Hire one, wait six months. Hire the other, wait another six months.

Now you're a year deep into a rebuild that should've taken half that.

Stack them and they build the revenue function together. As a team. The cost looks bigger up front because it is bigger up front. But the time spent in the transition valley is half. (And, if you hired right, you now have two A-players building a compounding revenue function in unison.)

The slower version is the more expensive version. It just spreads the cost out over time. Like a medicine you cut with water. It goes down easier, sure. But you have to take it for twice as long to get the same effect.

We made the call. Both VPs are in and doing great. They resisted the urge to pull back on ad spend.

It was a bold choice.

Five months later, the cost line landed exactly when I told her it would.

That's the valley. Cost hit the bank account, result still underway. The decision is doing exactly what it was supposed to do.

That’s the price of boldness.

But they’re headed out of the valley.

The new revenue team has averaged $500k/week out of the gate. The company is staring down the barrel of its first $1M cash month.

But the cautious version of this decision doesn't end here. The cautious version ends another 6 months from now, with the same eventual hires, the same worries, the same revenue gaps, but twice the runway burned getting to the other side.

Caution only delays the cost of a transition.

Perfectionism in execution is the only place it belongs. I don't need full confidence in the decision. I need full confidence in my ability to execute it down to the smallest detail. If I can't get there, I don't move until I can.

The question isn't whether the plan is airtight. It's whether the execution is precise enough to generate a real answer once you move.

One more question, while it's fresh.

What came to mind while you were reading this?

That's the one. It surfaced for a reason.

Your business is waiting for you to name it.

— Chris Piper

Your friend that just made a bold decision in their business and is now doing this? Do ‘em a solid and send them this email.

I want to start sharing more of what I’m building in real-time with clients. Is this interesting? Helpful? Boring? Reply and let me know. (Please. Otherwise I don’t know.)

Here’s something I cooked up this week.

YouTube Comment Scraper + Behavioral Change Analyzer

Problem: Disney Co. asked a creator-founder for KPI data showing their content actually changes behavior. No such data existed. We needed to generate defensible organic evidence fast, without a survey.

Solution: A Python script built in Claude that pulls top long-form videos via the YouTube Data API, fetches up to 200 comments per video, runs each batch through Claude to flag behavioral change signals, and outputs a branded Excel workbook with action type, confidence rating, and summary per comment. Now we’ve got the data, the confidence, and can go close this big brand deal.