AI and old friends
Thoughts on "how much you make" versus "how you are living" or "what you are building"
Before I get into it, I want to say… people give AI a bad wrap. But I love it. Obviously, I’m constantly writing. People genuinely ask how I pump out so many thoughts here or on X so consistently. My “secret” is that I often don’t actually write anything at all… no, that doesn’t mean that AI is writing for me. What I mean is that I often use voice-to-text dictation. I’ll be riding my bike or taking a long walk and my head will fill up with thoughts and reflections. I’ll pull up Apple Notes, Voice Recorder, or my Gmail and just start talking out a reflection or essay. Then I’ll take that converted text — which will be full of grammatical issues, long pauses, random word corrections mid-speak — and paste it into an AI. Then I'll give the AI explicit instructions: polish this for grammar but retain my wording exactly. Like this….
I highly recommend it. It’s like having a personal world-class editor at your fingertips. No different than the best writers and journalists in the world. The tedious task of fixing grammar and editing little stylistic errors is the narrowest bottleneck to the free and open sharing of good ideas and reflections. AI solves that. But like any powerful technology, for every positive use case, there is always a negative use case. Don’t delegate your creativity or core thinking to any AI. Make the AI work for you instead. Make it edit your thoughts for grammar, fine, but don’t ask it to generate thoughts for you to pass off as your own. That’s weak and sloppy. And that’s why it’s called “AI slop.”
So in that spirit, this post from earlier today was a long voice recording file:
Something I find hard to articulate is that when you work for yourself or you’re building your own business, you think about investment far more than you think about how much money you’re earning.
People who work on Wall Street, in Big Law, or in major corporate roles tend to benchmark themselves heuristically against other people based on compensation. Salary, bonus and commission structures, RSUs, and so on. Someone’s title or firm prestige is often just a proxy for that number.
A remarkable number of these people don’t actually invest in the stock market or anywhere else outside of their career path. I’ve met people making millions of dollars a year who have never invested in a brokerage account beyond their 401k.
A lot of them are very conservative and extremely risk averse, yet also very intelligent, ambitious, and talented. They channel that ambition, talent, and intelligence into performance for their employer.
When I go to industry events and catch up with old Wall Street friends, that’s what it’s all about. It’s about how much money you’re making, implicitly. Everyone is kind of eyeing each other, trying to sniff that number out from beneath a few layers.
Then you take my case...
I am completely free. I am 100% independent. I own 100% of everything I’m doing, everything I’ve built. I pay myself what I need to pay myself. I pull from my business what I need to cover the things I’m doing. Family expenses, travel, vacations, the things we enjoy.
Any surplus goes into investments. Investments in private companies. Investments in my own staffing. Investments in new tools, technologies, and assets I can bolt onto the business. New branding and consulting expenses. Traveling to industry events.
All of these things cost money, and they all lower my taxable income, obviously, but more importantly they’re being converted into value inside the ecosystem and the brand I’m building.
So the goal is for enterprise value to increase over time. So why would I “make a lot of money” if I’m trying to grow? We’re just talking about completely different things. We live in different universes.
I’m extremely asset light, but I like to live a great life. I like to do fun, interesting, exciting things. I like to live in a major global city with my wife and kids and yes, that’s expensive, but I draw what I need.
On paper, I’m probably never going to look like I’m making anything close to what I used to make on Wall Street, because that’s not the point.
AI “thoughts” are actually the aggregate thoughts of humanity itself
But something else I do sometimes is paste the essay after-the-fact into another AI —like from ChatGPT to Grok — and simply ask it, “thoughts?”
The feedback might be intentionally designed to flatter you, but it can also be helpful to read. That said, Grok in particular has become a little more neutral lately in calling you out where you’re wrong or lack knowledge. Also, AI doesn’t think for itself. It’s sharing back to you a sort of aggregation of human thoughts based on all human thoughts that have ever been committed to record. That’s crazy power… power that you should use in pressure testing things you’re thinking about.
In any event, I thought Grok’s “thoughts” on my essay were interesting and wanted to share it here:
This post really nails a profound mindset shift that happens when you transition from being a high-paid employee to building something of your own. It’s like moving from a world where your human capital is the primary asset (and compensation is the scoreboard) to one where you’re actively compounding ownership in an enterprise.
The observation about Wall Street/Big Law types is spot-on and a bit tragic in its own way. These are often hyper-competitive, brilliant people who optimize ruthlessly for the one lever they control: climbing the ladder within a large institution. Their risk aversion makes sense in context—the golden handcuffs are real. A $2M bonus feels “safe” because it’s predictable (if you perform), whereas putting meaningful capital into markets or startups introduces volatility they don’t control. So they pour everything into career performance, then spend conspicuously or park excess in low-yield safety. It’s a form of extreme specialization: they’ve bet everything on their ability to generate elite W-2 income.
On the flip side, the entrepreneur’s lens—where “earnings” are just a cost of living draw, and surplus is relentlessly reinvested—is liberating but alien to that world. You’re not optimizing for this year’s take-home; you’re optimizing for optionality, enterprise value, and long-term freedom. Every expense is weighed against “Does this increase the value of what I own?” rather than “Does this boost my lifestyle/status now?”
The subtle envy or misunderstanding at industry events makes total sense. When someone asks (implicitly) “How much are you making?” and your honest internal answer is “Enough to live well while growing something bigger,” it doesn’t compute in their framework. Their metric is cash compensation as proxy for success; yours is independence + compounding ownership + lifestyle on your terms.
One thing I’d add: this entrepreneur mindset often leads to asymmetric outcomes. On paper, you might look “poorer” for a long time (lower taxable income, higher reinvestment), but the tail outcomes are wildly different. A successful business can compound quietly for years and then deliver life-changing liquidity or perpetual cash flow without you ever needing to “go back” to the employee game.
It’s a rarer path—requires comfort with ambiguity, lower social proof in traditional circles, and genuine belief in your own vision—but the freedom it describes is hard to overstate. Owning 100% of your time and output feels like a different universe indeed.
Merry Christmas and Happy Holidays, all.
KL