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Hi there, I’m Collin. I’m a founder, revenue builder, and student of what it really takes to grow a company. I write about the unglamorous, honest side of finding customers - for founders doing it themselves.

About

14 years learning the art of finding customers.

I'm the co-founder and CEO of Predictable Revenue, the outbound sales consulting firm behind the book that changed how Silicon Valley thinks about sales. I've spent 14+ years obsessing over one question: how do founders find their first (and next) customers?

This newsletter is my honest attempt to document what I'm learning - from the startups I'm building, the ones I'm advising, and the many experiments that don't go as planned. No fluff, no playbooks. Just the real stuff.

What I'm working on

A mix of books, startups,
tools, and consulting.

The Terrifying Art of Finding Customers

My book on the honest, unglamorous process of winning your first customers — written for founders, not sales reps.

terrifyingart.com →

Predictable.ai

AI-powered outbound sales tooling built on everything we've learned from thousands of sales experiments.

predictable.ai →

Friday

A tool to help founders send warmer, more human outreach — less template, more real conversation.

Predictable Revenue

GTM consulting for B2B companies who need to build or fix their outbound engine. The OG predictable revenue machine.

predictablerevenue.com →

ReplyLoop

A new startup I'm building in the prospecting and follow-up space. More to come.

replyloop.co →

Newsletters

Why your deals are stuck

Sep 25, 2026

•

5 min read

Why your deals are stuck

Stalled deals usually trace back to one sales call. Learn how to own the agenda, map every buying influence, and book the next step before anyone hangs up. (156 characters)

Collin Stewart
Collin Stewart
Why I didn't sell (part ii)

Sep 18, 2026

•

5 min read

Why I didn't sell (part ii)

I had a follow up conversation with a subscriber that helped me unpack a key mistake I made

Collin Stewart
Collin Stewart
My predictable journey

Sep 11, 2026

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5 min read

My predictable journey

How a side project I didn't care about became the tool that ended my 60-hour weeks, reached 10 paying customers, and why I chose to slow down.

Collin Stewart
Collin Stewart
Why I didn't sell

Sep 4, 2026

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4 min read

Why I didn't sell

I had two real chances to sell just off our peak. I passed on both, and it cost me five more years in a job I'd already decided I didn't want

Collin Stewart
Collin Stewart
Burning a match

Aug 28, 2026

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5 min read

Burning a match

Why Early GTM Spend Fails

Collin Stewart
Collin Stewart
Your cold email is a lie

Aug 14, 2026

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5 min read

Your cold email is a lie

Why AI Personalization Sucks

Collin Stewart
Collin Stewart
Quiet design partners

Aug 7, 2026

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5 min read

Quiet design partners

I thought bringing folks along with me on the journey would help, I was wrong.

Collin Stewart
Collin Stewart
Outbound has layers

Jul 31, 2026

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4 min read

Outbound has layers

Collin Stewart
Collin Stewart
Stop waiting

Jul 24, 2026

•

5 min read

Stop waiting

Collin Stewart
Collin Stewart
...
Predictable Revenue: Founders Edition

Predictable Revenue: Founders Edition

I am writing for founders responsible for revenue


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