The Operating Week Ahead – Aspirations vs. Actual Results

A Weekly Curated Jumpstart for Your Operating Week Ahead

One lens, a few sharp moves, and a short list of inputs to help you operate better in an AI-shaped economy this week. If you only have 10 minutes: read Pine on customer aspirations, skim the Palantir agent thread, and try the tiny experiment at the end.

And most importantly, have an amazing, productive, killer week!

- john -

---

You Might Enjoy These:

• 0 to 55,000 - The First 90 Days Playbook - What I’d Do Differently Knowing What I Know Now

• WINNING THE LOSER’S GAME: The Creator Economy and the Companies We All Need to Build

• Operating Stories: How JP Morgan Chase Showed the Rest of Us What AI Transformations Can Achieve (Part One)

• Operating Economics: Building Antifragile Companies

• How Three Decades Rewrote the Economics of Companies

---

Three Things I’m Thinking About

1. Leverage beats generic hustle.

Bono once told Spotify founder Daniel Ek: “Good things come to those who work their asses off and never give up.” Truer words.

But the application hits a bit different in our current moment. The tasks that have constituted substantive work over our careers are now meant to be built into prompts, applications and directions for agents. The key mindset adjustment is not to think of automation in terms of time saved for leisure activities; it’s to double down on working the same number of hours to produce 10x (100x?) the output. Our prompts, workflows, and distribution systems can compound our output while we sleep. That means we can accomplish in days what once took weeks or months. Just as startups think in terms of exponential growth, so should we be applying the same logic to our work and ambitions. We are all becoming companies. (McKinsey: Agents, Robots, and Us)

Week Ahead Prompt: Where can you swap “more hours” for “better leverage” with AI or automation this week?

2. Intentions don’t ship. Execution does.

Nobel economists Milton Friedman warned against judging policies by intentions rather than their results. The same applies to your company, career and working strategy. It is now cheap and fashionable to announce an AI-strategy or to speak to one’s expertise in the field; it is rare to see a single measurable workflow redesigned so a human and an AI agent actually share the work and accomplish more than would be otherwise possible, together. This week, I’m less interested in what people believe about AI and more interested in what’s visibly faster, cheaper, or better because of it. (McKinsey: Agents, Robots, and Us)

Week Ahead Prompt: Name one workflow where you can define a clear before/after metric — then invite an AI agent into the loop.

3. Face your customer’s new reality.

Jack Welch said to face reality as it is, not as you wish it to be. Pine’s new HBR piece on customer aspirations shows how fast that reality is shifting. In a world of AI-generated abundance, customers are less impressed by features and more drawn to offers that move them closer to who they want to become. Most of us are still building for the customer we met three years ago, not the one reshaped by remote work, AI tools, and rising uncertainty. This week, start thinking differently about your customer. Start llistening to the ‘Why’ of what they actually want.

Week Ahead Prompt: What is one customer aspiration that has changed in the last 12 months that your product or service hasn’t acknowledged yet?

---

Three Articles Worth Reading

“AI and the Human Condition” — Stratechery (System) A wide-angle lens on how AI abundance changes the meaning of work, value, and being human. Read it less as tech news and more as a framing device, then ask: What kind of distinctly human value will my company still provide when AI is everywhere?

“Agents, Robots, and Us: Skill Partnerships in the Age of AI” — McKinsey Global Institute (System / Macro) McKinsey maps where AI agents and robots already substitute or complement human work, and how “skill partnerships” between people and machines will evolve. Skim the exhibits on changing skills and imagine designing your business from scratch. AI is your first hire, humans are added at the junctures where judgment and relationships matter most.

“Do You Know What Your Customers’ Aspirations Are?” — B. Joseph Pine II, HBR (Customer / Growth) Pine argues the real offering is change, helping customers progress toward aspirations ranging from security to transformation. Read it with a pen and your favorite notebook. Circle the aspiration that best matches your top customer segment, then ask whether your current offer actually moves that aspiration forward or just describes it.

---

What to Listen to and Watch

This week’s theme: seeing around corners with AI and operators who actually ship.

Podcast: “Do This If You Want to Build A Business You Love” (Dave Ramsey Interview) — Alex Hormozi, Ep 871 Even is Dave Ramsey’s content is not something that speaks to your immediate needs, as a Creator, Founder and business builder, you need to understand his story and how he has built Ramsey Solutions. The man is a customer serving, content distributing GOAT.

YouTube: “Adam Neumann: This is How You Build Iconic Companies” — The Ben & Marc Show (a16z) Neumann, Andreessen, and Horowitz unpack WeWork, Flow, and what it means to take another swing at category-defining scale. When I first listened to this over the holidays, the immediate take away was Marc and Ben saw the WeWork failure as the driver behind investing in Neumann again. The interview is also fascianting when it comes to their discussion of Flow building out their entire operational tech stack without the help of traditional B2B software vendors, instead choosing to build a custom stack entirel. That model has so much to do with where the market for B2B software is going.

Short on time? Start where they dig into product and community for the new venture.

X Thread: Palantir on AI Agents

Palantir Chief Architect Akshay Krishnaswamy joins Senior Counselor Jordan Hirsch to discuss the future of work and artificial intelligence. Building on the Working Intelligence project showcasing AI deployments that enhance workers, Akshay explains how properly built AI systems can liberate human creativity and capture the vast untapped intelligence in the people on the frontline — making those with the deepest expertise not expendable, but ever more valuable.

Palantir frames AI agents as operational teammates that perceive, decide, and act inside complex organizations. Companies are using them to pressure-test their own agent ideas: what boring, high-frequency, currently human-heavy problem inside your business would benefit from an agent quietly running in the background?

---

Long-Cycle Listening

(All Available for Free Listening as Audiobooks on Spotify with Premium Plan)

Not “finish this week” picks. Treat them as background curriculum for the next month.

Against the Gods: The Remarkable Story of Risk — Peter L. Bernstein (History / Risk) How humans slowly learned to quantify and share risk, from early probability to modern finance. Notice how each leap in risk understanding created new business models — then ask what the risk tools of the AI era might be for yours.

The Fish That Ate the Whale: The Life and Times of America’s Banana King — Rich Cohen (Biography) An entrepreneur building an empire in an unglamorous, operationally gnarly domain. Listen for how logistics, distribution, and a willingness to operate in overlooked markets created outsized power. Then translate that lens to today’s less crowded niches.

Day Trading Attention — Gary Vaynerchuk (Actionable for Creators) A tactical guide to finding underpriced attention and shipping imperfect experiments fast. Don’t try to copy his entire tempo. Pick one platform, one daily micro-experiment you can actually sustain, then review the data in a month.

---

Operating Quotes

“Good things come to those who work their asses off and never give up.” — Bono to Daniel Ek

Operator translation: Disciplined, consistent, maniacal execution is the variable.

“One of the great mistakes is to judge policies and programs by their intentions rather than their results.” — Milton Friedman

Operator translation: Outcomes > Opinions

“Face reality as it is, not as it was or as you wish it to be.” — Jack Welch

Operator translation: Wishes are not realities.

---

Build Your Digital Advisory Board

If you’re curating a small board of advisors in your feed, these five earn a seat this week for me:

Scott Galloway (Story / Macro) — Cuts through noise on markets, demographics, and power dynamics in tech. Follow him for sharp narratives that force you to ask whether your own story is honest and differentiated.

Will McTighe (Messaging / Systems) — Want to build your brand on LinkedIn, start with Will. Watch how he structures hooks, builds offers, and creates feedback loops between content and product.

Tyler Cowen (Economics / Judgment) — Long-term, global view on growth, talent, and decision-making in strange times. Treat his work as training for your judgment muscles, especially around trade-offs and opportunity cost.

Gary Vaynerchuk (Distribution / Execution) — A constant reminder that distribution, volume, and experimentation still beat perfectionism. Let his feed push you toward more tests, more posts, and more small bets in public.

Alex Hormozi (Offers / Conversion) — Relentlessly focused on building simple, compelling offers and the systems that sell them. Study how he frames value, risk reversal, and proof — then audit whether your own offer is anywhere near as clear.

---

One Tiny Experiment for This Week

The Aspirations Audit. Block 30 minutes. List the five most repetitive tasks you touched today. Circle one that AI could meaningfully assist — not fully replace. Prototype a simple handoff of part of that task to an AI tool. Then write one sentence about how this change makes your customer’s aspiration more achievable, not just your life more convenient.

The difference between “AI helps me” and “AI helps my customer through me” is the whole game.

---

If this nudges you to redesign even one element of your workflow, introduces you to somone new, or simply provides a little inspiration to start your work, than it did its job.

Hit reply with how this helped or could be better. I read every response.

And most importantly, have an incredible week of work. Crush it.

- j -

---

Appendix: All Links in One Place

Articles

• AI and the Human Condition — Stratechery

• Agents, Robots, and Us: Skill Partnerships in the Age of AI — McKinsey Global Institute

• Do You Know What Your Customers’ Aspirations Are? — B. Joseph Pine II, HBR

Podcasts & Videos

• Do This If You Want to Build A Business You Love (Dave Ramsey Interview) — Alex Hormozi, Ep 871 (Spotify)

• Adam Neumann: This is How You Build Iconic Companies — The Ben & Marc Show, a16z (Apple Podcasts)

• Palantir on AI Agents — X / @PalantirTech

Audiobooks

• Against the Gods: The Remarkable Story of Risk — Peter L. Bernstein (Amazon)

• Against the Gods — Peter L. Bernstein (Spotify)

• The Fish That Ate the Whale — Rich Cohen (Amazon)

• The Fish That Ate the Whale — Rich Cohen (Spotify)

• Day Trading Attention — Gary Vaynerchuk (Amazon)

• Day Trading Attention — Gary Vaynerchuk (Spotify)

---

John Brewton documents the history and future of operating companies at Operating by John Brewton. He is a graduate of Harvard University and began his career as a Phd. student in economics at the University of Chicago. After selling his family’s B2B industrial distribution company in 2021, he has been helping business owners, founders and investors optimize their operations ever since. He is the founder of 6A East Partners, a research and advisory firm asking the question: What is the future of companies? He still cringes at his early LinkedIn posts and loves making content each and everyday, despite the protestations of his beloved wife, Fabiola, at times.