I thought I was giving others unsolicited advice because “I wanted to help them”… in reality it was motivated by insecurity
once I unlearned my insecurity, the urge to give unsolicited advice simply stopped. completely effortless from then on
Despite what the AI memos would have you believe, most CEOs are quite timid about changing their organization.
Roles aren’t really changing. Teams aren’t being aggressively reshaped. More slop is being generated, but not more customer impacting things. It’s the same, maybe more or faster, not completely reimagined.
While you think most C-level leaders have AI psychosis, more (honestly) have AI paralysis.
I keep telling execs to put an org chart on a wall and start circling and X-ing. What changes? What goes away entirely? Highlight the ai native archetypes in your team. List agents alongside teammates.
Then—aggressively reskill and upskill your team.
As I say: change is coming. It can happen to you, or you can pull it forward.
It’s time to be honest, and then be bold!
Agentic coding tip
Pay down tech debt immediately
With agents, there should be no such thing as “tech debt”. An agent should simply pay down every bit of tech debt before presenting you with the “finished work”. Unlike humans, agent time is not very valuable; it can and should continue to work on something until it’s done, and shouldn’t make concessions assuming human constraints.
If an agent tells you that it’s “leaving something for later”, tell it to go finish it first before saying it’s done.
Example prompt (best if it is in your docs):
```
Do not leave any tech debt behind. If you have taken any shortcuts, go back and do them right. This is a hard acceptance criteria that must be completed.
```
Tip: If you have a daily workflow you want to automate, ask the agent to write down the steps so it can faithfully execute it every time. It is an extension of its skills.
It may take some iterations to reach deterministic results, but it’s worth the effort.
In my private repo, I have more plans than code.
You should, however, make sure to write a unit test against your plans so that when the model changes it does not catch you off guard.
💯 Founders want to be congratulated for closing that one large $100k enterprise contract that took them 6 months but the reality is that more companies are growing to millions in revenue in 6 months by use very different go to market approaches.
Building the old school way it literally just dying a slow death.
Overwhelm is not as it appears.
It appears to be too many things to do, when in reality it is not doing the things that need doing.
It appears to be too much emotion, when in reality it is not feeling your emotions all the way through.
It appears to be a constriction that you need to stop, when in reality
it is your life looking for an expansion that is being resisted.
Overwhelm is a sign that your identity is too small for the actuality you are becoming.
I think the main thing AI has taught me, through all the time savings it brings, is that I’m not a very interesting person
Faced with a surplus of free time, I realize I don’t really have hobbies besides content consumption
I’m forced to conclude that I don’t have very deep friendships, and am not a core member of any particular community
I’m not very cultured, I’m finding, and don’t have abiding interests in art or literature or history or much that isn’t directly related to my work
I have a work-centric life, in other words. AI pulls back the curtain on just how impoverished such an existence is, by disabusing me of its necessity
Given the freedom I’ve always said I wanted, I’m at a loss as to what to do with it, except plow myself even harder into work, thus exacerbating the lesson
There’s nothing more confronting to humans than freedom
I knew nothing when I started a media company (The Hustle). Nothing! Had never worked in the industry, didn’t know what CPM meant, didn’t know a single person who worked in the field.
So I reached out to a bunch of successful media founders, hoping they’d guide me.
But how on earth do you find someone super successful to give you, a piss ant with next to nothing to give in exchange, some good life changing advice?
I ended up finding this guy, Kevin Ryan, who, I think, is a billionaire. He started Gilt, MongoDB, and Business Insider.
I found his email and sent him a note asking to talk. Zero reply. So I kept following up with updates on the business and my life. Revenue growth, issues in the business, how I was feeling about it all. Almost like an investor update, but written in an entertaining way.
After doing this for months, I finally got a reply saying he was available in NYC for a very quick meeting
“What a coincidence,” I told him, "I happen to be in NYC, let’s do it!”
I was in SF at the time. And obviously didn’t have a trip planned to NYC but I booked the next flight anyway.
And it worked! Kevin met with me and in our short meeting gave me very needle moving advice that had a huge impact on my business and life.
This habit of googling cool people and then cold emailing them, it likely was the #1 most impactful thing on my career. I’d cold email them, get no reply, then follow up with business/life updates until I got a reply. I made the emails fun to read and people would get invested and think “ok, this guy might be legit, I’ll give him a chance.”
That’s how I met my Hampton cofounder Joe - I googled something generic like “fast growing media startups” and then I asked to hang out. We ended up becoming close buddies, after 6 years of being friends, cofounders.
In fact, this is how I met Shaan!
Nowadays, Twitter makes this much easier. Use the same profile picture across gmail, social, etc…post a ton, reply a ton, and people get to know you.
Moral of the story - nobody is out of reach. Make the ask…and follow up, follow up, follow up!
is anybody studying this?
one of the most interesting questions to me is how AI changes where people go for comfort, advice, reassurance, and decision-making
i know we probably don’t have enough longitudinal data yet to understand the full effects, but what happens socially when a lot of small bids for human connection get redirected elsewhere?
when the father question, the friend question, the mentor question, all become the AI question
Cohering one’s life around a single hard but meaningful goal is such a reliable producer of happiness.
Especially relative to strategies like: directly pursuing happiness.
Your willingness to embrace intensity is the best leading indicator of personal growth. What I mean by "embracing intensity" is feeling everything there is to feel inside you. It is the thing inside of you right now that has some discomfort.
Everyone thinks "do things that don't scale" is about building relationships with early users.
Yes AND it's about generating mistakes at maximum density.
When you're doing everything manually (onboarding, support, delivery) you hit errors every hour. Each error teaches you something the dashboard never will.
The manual work IS the learning. Automate too early and you freeze your ignorance in code (and now markdown).
Every summer I took Teles to market as if I was actually going to sell it.
I identified 3 to 5 potential buyers, put the package together, and went through the process.
Then I'd ask: "Based on all of this, what would you pay?"
They'd give me a number. I'd say, "Why not more?" They'd tell me exactly what needed to change.
I'd hand that list to my COO and say: This is your business plan for the year.
2 things happened every time:
1. They saw a business that could grow
2. They saw a team that could execute
Build your business to sell.
When you don't know your options, you don't have any.