Derek R. Haswell

exec coach, entrepreneur, community steward, farmhand, school builder, dad x3 || supporting high consciousness x high agency

[Derek R. Haswell @DRHaswell]

For any ingrained behavior, there’s usually a constellation of patterns that keep a person feeling stuck.

Unwinding those usually involves a mix of big aha moments where people experience a major discontinuity (like these), alongside smaller wins.

They compound if you stick with it, but the tipping point often isn’t clear until you’re looking in hindsight.

The most experienced practitioners I know don’t promise “one-shots” — that kind of agenda undermines the work.

[Chris Lakin @chrislakin]

A year ago I observed a coach who was extremely confident he could help any person with any issue. Intrigued, I witnessed over a dozen first sessions that ended in: “That was crazy! This is awesome!” “THANK YOUUUUUU [7 heart emojis] THANK YOU [heart emoji] My heart is filled with gratitude” “This is LIFE-CHANGING!”

However, when I checked in with these people a few weeks/months later to track results, it was clear their lives hadn't improved. They might've stopped avoiding, procrastinating, etc. for a few days or even weeks after talking to him… but in almost every case they quickly relapsed. There were few exceptions.

This is what bypassing looks like up close.

[Derek R. Haswell @DRHaswell]

@jonnym1ller Great recap. What a time to be alive!

[Lenny Rachitsky @lennysan]

My biggest takeaways from @danshipper:

1. The future of work will happen inside Codex or Claude Code. Instead of putting AI into your SaaS tool, you’ll use your SaaS tools inside your favorite AI agents' in-app browser. Dan spends all his time in Codex now—writing documents, managing email, doing research, everything. He's using Google Docs, PostHog, and everything he needs within the agent's in-app browser. The agent can see what he’s doing, and has all of his context, so he and his agent collaborate quickly and super effectively.

2. Automation is a lie—every automation needs a human. Dan's company doubled in size this year despite being incredibly AI-forward. Why? Because in order to make automation work well, you need humans making sure everything keeps working. This is why benchmarks are misleading—they measure AI on problems we’ve already framed and can score, but there’s always a higher frame.

3. PMs will win the AI era. Marcus, a former PM who previously ran Axios’s writing product, joined Every after getting super AI-pilled. Now he runs their product Spiral, and ships faster than anyone on the team. He pairs technical knowledge with spiky product sense, deep user empathy, and an eye for what matters. Dan thinks any PM who gets really AI-native will be incredibly dangerous because the building is done for you—what matters is figuring out what to build and if it’s great.

4. Full-stack designers are becoming superheroes. Designers used to make beautiful interactions that engineers didn’t want to build or couldn’t execute properly. Now designers don’t need to hand things off; they can build it themselves. Designers are naturally creative people, and AI is the perfect tool for them because it lets them bring their vision to life without the traditional bottlenecks.

5. SaaS is not dead. In fact, Dan is bullish on SaaS stocks. When users bring their own AI (via Codex or Claude Code) to use SaaS products, the user—not the SaaS company—pays for tokens. This saves SaaS company’s margins. Since the agents need their own seats, Dan predicts that agents will create massive new demand for SaaS because there will be tons of agents using these products at high volume.

6. Every company will have one “super-agent” inside their Slack that every employee will use. Dan initially thought every employee would have their personal work agent, like a shadow AI org chart, but he’s completely flipped his view. He realized agents need humans who care about them. When someone gets tired of maintaining their personal agent, it becomes useless. The winning model is one forward-deployed engineer or AI-savvy person who maintains a company-wide agent (like Shopify’s River or Viktor), and then it trickles down to more specialized team agents as models improve and become less fiddly.

7. The AI job apocalypse is not happening, but you do need to evolve to stay relevant. Models make yesterday’s human competence cheap. But because everyone uses the same models, it all looks the same if you use it the default way; it becomes commoditized slop. Humans then take that frozen competence and use it to make something new and interesting for their specific situation. The key: “ride the models”—use them for everything you do, try new models when they drop, keep turning over rocks.

8. We will read way more AI-generated writing, and we will like it. Human writing is incredibly important for things that matter, but for internal docs, planning, and email, AI-generated is often better because most people are bad at writing strategy documents.

9. Build software for humans and agents to use together. The current model is building a CLI that an agent uses independently. Instead, you and your agent should be using the app together. This creates new design challenges—agents can make a billion requests in three seconds, so you need approval flows, inboxes that summarize what happened, logs, and easy rollback.

10. Forward-deployed engineers are the new most essential role. The big model companies have teams of people managing their internal agents, and those teams aren’t going away. It’s different from traditional software building, and certain engineers love it. As models get better, this role will evolve—you’ll be managing more agents doing more things.

[Derek R. Haswell @DRHaswell]

@JonMSchwartz Gotcha.

Operator 8 would not be pleased with this either.

[Derek R. Haswell @DRHaswell]

@Ultraroboticsco 🔥

[Derek R. Haswell @DRHaswell]

@Tim_Org Same. Tastes so much better too.

But hard to do when we lived in (or around) Boston.

[Derek R. Haswell @DRHaswell]

@bhalligan Curious — what are the most effective ways you see founders making the shift from the bottom trend to the top one?

[Derek R. Haswell @DRHaswell]

Having now raised animals that we eat (chickens, turkeys, lamb), I can’t unsee how important it is for animals to live happy, healthy lives until harvest.

The more disconnected we get from our food (and nature writ large), the harder it is to spot the things that are so clearly bad for our society as a whole.

Call your state rep.

[Lewis Bollard @Lewis_Bollard]

Despicable: the House just passed a farm bill that includes the SOB Act to keep pigs imprisoned in crates.

Our last hope is to keep this out of the Senate farm bill. Call your senators at [phone] and tell them NO farm bill bill with the Save Our Bacon Act in it.

[Derek R. Haswell @DRHaswell]

“Optimism requires creativity. Doom is easier to imagine, so we have to nurture optimism and be irrationally optimistic, because that’s the only way out.”

[Naval Podcast @navalpodcast]

Executive Brief of our latest episode:

‘Nothing Ever Happens’ Is Over

1. As companies grow, the communication overhead gets very high, so the traditional answer is hierarchy. This creates politics, permissioning, and a world where the CEO needs ‘founder mode’ just to talk to an engineer.

2. The alternative is a fully interconnected graph: everyone can talk to anyone, with a light hub-and-spoke around one person trying to keep the whole product in his head.

3. This only works if every node is highly intelligent. You need people who can navigate their way to the person they need to talk to, cooperate directly, and survive without management theater.

4. In that kind of company, AI starts replacing the explicit intranet. It can go through the codebase and tell you who in the organization is likely to be an expert, so you don’t need everything manually documented.

5. You don’t need fixed dashboards when AI can create them on the fly. AI can constantly be doing data analysis and reporting for you—reports on demand.

6. There are two, maybe four, companies that are dominating AI. The question is whether AI becomes a commodity business, a monopoly business, or an oligopoly business.

7. The famous meme “Nothing Ever Happens” is over. Post-COVID, the world is changing a lot faster.

8. Drone warfare changes the structure of violence in society. Drones bring mutually assured destruction down to the individual level.

9. Hardware is getting unlocked through software. AI means hardware companies can make good enough software, because agents can interact with the hardware directly.

10. Optimism requires creativity. Doom is easier to imagine, so we have to nurture optimism and be irrationally optimistic, because that’s the only way out.

[Derek R. Haswell @DRHaswell]

@Tim_Org A beautiful share, Tim. I’m sorry to hear about your brother. May he find peace on the next leg of his immortal journey. ❤️

[Derek R. Haswell @DRHaswell]

@khemaridh @nateliason 👀

[Derek R. Haswell @DRHaswell]

@Montebello @jonnym1ller Who told you about the stuffed animals?

And there are lambs in our house, but they’re currently in my freezer 😬

[Derek R. Haswell @DRHaswell]

@Montebello @jonnym1ller Both of you guys have been subjected to me wearing blankets during our calls because Oxygen > warmth.

I think this is the most overlooked simple fix that most people don’t even know they’re struggling with.

[Derek R. Haswell @DRHaswell]

Tablestakes!

[Brian Halligan @bhalligan]

No matter what kind of company you are...start making your internal company data legible to AI. Today.

As a founder, you are essentially building two versions of your company: the one humans work in and the digital twin that AI agents navigate to do the heavy lifting for you.

[Derek R. Haswell @DRHaswell]

@jonnym1ller @drmichaellevin 👏

[Derek R. Haswell @DRHaswell]

Small Claude Code quality-of-life improvement for those using Claude's app: have it auto-unarchive a session if you re-start a conversation in it.

Helps keep things cleaner if your inbox-zero habits are as ingrained as mine.

[Derek R. Haswell @DRHaswell]

@Tim_Org Congrats, Tim!

[Derek R. Haswell @DRHaswell]

@Tim_Org What?? Where?

[Derek R. Haswell @DRHaswell]

@Tim_Org During farm chores?