Sam Jacobs

These are my favorite conditions.

Calling it "writing" is no longer accurate. Assembling. Editing. Collaborating. Virtually everything I'm reading right now is clearly constructed with AI in some way. You can tell by the sentence construction. Over use of the word "quietly". The phrase "no fluff". The negative positive sentence construction. "That's not this, it's that" My preferred workflow is AI as research assistant and outline drafter. From there I write the body, edit, and ensure that the piece stays in my "voice." Others are doing that as well. But virtually nobody is simply starting from a blank screen or sheet of paper and "writing". This is not a judgement or condemnation. It's simply an observation. We live in wild times. (This is a picture of me writing this post just now because posts with pictures of you in them get higher engagement I think. Thank you for your attention to this matter.)

When electricity first appeared in factories, manufacturers simply replaced steam engines with electric motors. The production layouts stayed exactly the same. Productivity barely changed. It took decades before managers realized that electric motors allowed machines to be distributed throughout the factory floor rather than connected to a single central drive shaft. Once factories reorganized around what electricity made possible, productivity surged. Robert Solow showed something similar in a famous 1957 paper: most economic growth can't be explained by adding more labor or capital. It comes from better ways of combining those resources. We're in the middle of this moment with AI right now. The tools themselves aren't the breakthrough. The breakthrough comes when people reorganize work around what the tools make possible. Most organizations haven't done that yet. samfjacobs.substack.com/p/the-operator…

A master furniture maker doesn't arrive at a job and ask what tools the workshop has available. They bring their own chisels, planes, measuring instruments, and specialized saws. Over time they accumulate custom jigs designed for very specific tasks. Those tools aren't products meant for sale. They're extensions of the craft. Something similar is emerging in knowledge work. Operators are building their own AI workflows, automation scripts, small internal applications, research pipelines. Not products. Toolkits. If software becomes inexpensive to produce, the competitive advantage shifts away from the existence of software itself. It moves to the people who know how to combine tools with judgment and context to solve real problems. The best carpenters were never defined solely by the tools they owned. They were defined by how they used them. samfjacobs.substack.com/p/the-operator…

Here's something that changed how I think about my job: Every dollar you spend on acquisition is trapped. Trapped until a customer pays you back. The speed at which that happens — your payback period — is one of the most important numbers in your business. Fast payback means you can reinvest faster and grow faster. Slow payback means you’re waiting. And a high LTV:CAC ratio? Not automatically a good thing. I know a company at 17:1. That sounds like bragging rights. It’s not. It means they’re not investing enough in growth. We want healthy, not just high. The bigger shift: revenue has a cost. If you’re leading a GTM team, you’re not just hitting a number — you’re allocating capital. The best operators understand that. These are the kinds of conversations we have in Intro to P&L Fluency. The next cohort starts April 7 — three Tuesdays (April 7, 14, 21), 90 minutes each. Built for GTM leaders who want to actually understand the business they’re running. Link in comments: joinpavilion.com/pavilion-unive…

Prior to starting my company, I’d been fired 4 out of my last 5 jobs. It took a huge toll on my mental health, but I’m better at managing my depression today because of it. Here are a few things I’ve done to help reorient my mindset, stay focused, and stay positive: - Journal affirmation and gratitude every day - Exercise 60 minutes every day - Prepare a “Good Day Sheet” (a simple list of 5-7 things that if I do them, I know I’m more likely to have a good day) - Say “I love to you” to myself out loud and regularly - Reread parts of the Untethered Soul and remind myself that happiness is a choice - Read novels - Meditation and mindfulness - Text random people that I care about the moment they pop into my head and tell them how much they mean to me - Forgive myself but reflect on what I can do better for next time - Remind myself to take the long view and view setbacks as experiences - Remind myself that life is short and I can tell myself any story I want while I’m kicking around on this planet I try to do these things every day. Mostly I’m successful. But sometimes I’m not and that's OK. Here's the bottom line: Be kind to yourself. Be supportive to yourself. You deserve to be happy.

@pmarca @davidsenra Marcus Aurelius? Abraham Lincoln?

It is 100% true that great men and women of the past were not sitting around moaning about their feelings. I regret nothing.

We are in a world of commodity software products where people think they can vibe code what you've spent 10 years building in 30 minutes on the weekend. You need real marketing to differentiate yourself. Your marketing can't just be "Ha ha they don't have any security and we're SOC-2"

You don't need a "Chief Storyteller". That's your head of Marketing. You need a marketing department. Stop being a moron. Just hire a great marketer.

Last week, I was on the phone with a friend of mine who is a CRO. He’s a specific kind of CRO. He runs revenue at a $50M company that’s growing roughly 25% this year. But he also carries a $5M personal quota, a number he regularly hits and exceeds. He’s currently negotiating his compensation, and the framework he’s using is simple: he’s doing the job of a CRO, managing a reasonably sized team. And he’s also doing the job of a high-performing enterprise account executive. Not only is he willing to sign up for that number, he likes the work. He enjoys leading. He enjoys closing. And he’s built the infrastructure and support around himself to do both. He’s leveraging the right tools, he’s disciplined and responsive, and he is capable of handling multi-threaded multi-stakeholder conversations with some of the best companies in the world. He’s asking for a $1M compensation package. The math works. A CRO of a $50M business should probably make around $6-700K with a $300K-$350K base. A strong enterprise AE closing $3–5M should make another $300–500K. If my friend hits the number, he’s giving ownership a very good deal. The company may not see it that way. But that is the reality.

A RevOps guy showed me 3 apps he built in a weekend with Claude, Lovable & Replit. Each one could be a company. He asked me what to do with them. My answer: most shouldn't be companies. They should just be tools. Full essay → samfjacobs.substack.com/p/the-operator…

My 6 rules of doing business: 1. Look to help others before you help yourself. 2. Do as much as you can for other people and ask nothing in return. 3. Try as hard as you can to stop keeping score. 4. Play a long big game instead of a short small game. 5. Build relationships not transactions. 6. And try to use the power of love, optimism, and gratitude to power as much of your decision-making as possible. Bottom line: Believe in something bigger than yourself and come from a place of hard work and compassion and you should do just fine.

Watching this reminded me why I will never be a billionaire: Travis is an incredible entrepreneur. He has an incredible force of will. At one point he says (paraphrasing): "If you're a marathoner and you're at Mile 21 you're either in pain. And if you're not, someone is about to catch you." This was in the context of "going all the way". Elon might call it "hardcore". It's clear that becoming a billionaire might require that level of intensity. Problem for me: I'm not really that personality type. I'm hoping I'm smiling at Mile 21. (Literally. I'm running Barcelona tomorrow). Every time I try to mimic what I think being a CEO is like and go 100% balls to the wall hardcore it feels empty and fake. My greatest creations have come not from a desire to "eat glass" as Jordi and John mention. My greatest creations come from joy. The simple act of creating. Childlike wonder. I write songs. I build companies. I build apps (now). I write books. I write newsletters. The best of it comes from the sheer joy of expressing myself without fear of judgement, recrimination, accusation. The thing that happens when you hear something in your head, pick up your guitar, and a few hours later it's a song. And maybe a year after that it's on Spotify and recorded with professional musicians. The very long game of creating something beautiful. I get self-conscious when I watch those videos. Because I feel like I'm an imposter. Maybe I am. But in my most honest moments I know that my greatness doesn't come from the competitive mindset. It comes from the creative mindset. I know there are other entrepreneurs out there like me. I know there's more than one way to be successful. I acknowledge there might be only one way to be a billionaire. But I'm betting and I'm convinced you can make lots of money while still nurturing an entirely different part of your personality. The love of the game. That's why I do what I do. The love of creating stuff. See you at Mile 21.

Most founders misunderstand how to make money. It’s not about winning deals. It’s not about hiring tons of reps. It’s not about your sales methodology. It’s not about building a headcount driven revenue model. It’s about getting a meeting. The meeting is the atomic unit of your growth engine. A salesperson with the best playbook and no meetings gets fired. A salesperson with tons of meetings and no process will still close a deal here or there. Your best and most important investments should flow into getting better and better meetings. That means investments in demand generation and marketing. Which means investments in messaging, differentiation, and your ideal customer profile. Messaging + ICP > Demand Generation > Meetings > Pipeline > Money That’s the flow.

I'm sick of VPs of Sales that don't understand how to read financial statements. I'm sick of Heads of Sales that don't understand that hiring more salespeople does not make more money. You know what makes more money? More meetings. You have to invest in the creation of meetings. Meetings create opportunities. Opportunities create money. Salespeople turn opportunities into money. But they don't create opportunity. A salesperson with the best process in the world and no meetings, gets fired. A salesperson with no process at all, but with tons of meetings, can make you money. So the way that we make money, is to invest in demand generation. Of course, this is easier said than done. But that's what you've got to do. So the VP of sales that says the way that we're going to hit our target is hiring 10 more reps... That's not the right person for the job.

The entire SaaS valuation framework was built on 5 assumptions: cheap acquisition, high switching costs, low cost to serve, growing retention, and high-margin growth. How many of those are still true for agentic businesses? I count zero.

I was out the other night with a good friend who is CRO of a PE-backed ed-tech company doing $25M in ARR. She laughs that the title is “Chief Revenue Officer” but she’s really the sole enterprise seller at this company. She has 2 BDR-types that help set meetings and do research on prospects. She handles 90% of all sales calls and all good leads are routed to her. She closes $5-7M in new business every year. She works about 30 hours a week. She makes 7 figures. The founders of the company are delighted with her. She loves her job. The company is growing 30% YoY and is profitable, some part of that from her new business acquisition and a lot of it from natural expansion from happy customers. This is the new world of revenue generation. Sustainable, durable medium-growth profitable businesses that funnel their best leads to a handful of experienced sellers who buyers want to talk to. The leads come from a good product. They come from a small team of researchers. They come from partners sharing good opportunities to mutual benefit. They come from word of mouth. And they are routed to someone that can close them, enjoys the work, is grateful for the work, and delivers results.

Every time a first-time community founder uses the word "scale", an angel loses its wings.

The average tenure of a GTM CXO is 18 months and falling. But what's the average tenure of an AI/Agentic GTM CXO? This is the important question of the day.