What I'm Doing and How It's Going

How I went from a $350K FTE to $700K+ doing my own thing

I’ve needed to write this for a long time, for multiple reasons.

  1. Lots of people have been asking what the hell I’m doing. Like do I work somewhere? What do I actually do all day?

  2. Tons of my friends are either miserable at work or are getting laid off

  3. I believe that the time for being identified by—and tied to—corporate jobs is passing, and it’s time to transition to what comes next

I want to cover each of those and then talk about what we can do about it.

1. Lots of people have been asking what the hell I’m doing

My most urgent but least important reason for writing this is to just update people on what I’m doing. I have constant conversations with people I used to talk to a lot who say things like, “So you still at Apple?” And when I’m like, “Nah, I left there years ago and went to Robinhood for a couple of years.”, they’re like,

“Wow, had no idea.”

Fair enough. I do the same to lots of people too. We don’t have time to keep up on LinkedIn updates for the hundreds of people we know.

So, short version, I was at IOActive, left to go to Apple to build the BI function and platform for InfoSec for 3 years (before Covid). Left there to go to Robinhood for 2 years to build their Vuln Management team/platform. Then at the end of last year I left RH to go independent.

That was a couple months before GenAI popped, and the timing couldn’t have been more perfect.

1.1 Why I quit the Matrix standard system

You’ve probably seen a million of these types of pitches:

Let me show you how to make 3.7 billion dollars every 15 minutes!

Scammer or narcissist, usually

I’ve seen those too, and I avoid them. Maybe some are real, but I have no interest in an Amazon drop-shipping or an Orphan Bloodletting business. Or whatever the hell they’re doing.

My reason for making the transition was very simple. It wasn’t about money. I was making good money in corporate InfoSec. No. I just had to get away from corporate jobs where one or more of these were true:

  • Leadership didn’t know what they wanted

  • They knew what they wanted but couldn’t articulate it

  • They could articulate it, but couldn’t execute

  • So the company spends most of its time in planning sessions that will be ignored within a few weeks, only to do it again in a couple of months

  • Hours, days, and weeks of time wasted on Zoom calls because of the problems above

  • They hire and fire with the empathy of a moldy sandwich

  • I was spending all my time on a thing I didn’t think improved the world as much as I could have doing something better

In other words, I felt I was wasting my limited time on Earth.

It was SOUL-CRUSHING, and I was done dreading Mondays.

1.2 What I’m doing now

I’ve transitioned to answering the most important question I’ve ever heard.

What would you do if you weren’t afraid?

That’s a life-changing question, and you should be asking it often.

When I asked myself that question I realized I should be working for myself, building things that help people, consulting with people to help them, and putting that content into the world somehow.

So today I run Unsupervised Learning, which is not just the newsletter/podcast but the parent company of three separate pillars.

  1. Builder: First, I’m building a platform for solving all sorts of problems around purpose, focus, and execution—both for individuals and companies. See above! If that sounds vague, that’s ok, we’re still not talking about the product publicly yet. The first product we’re building on that platform addresses the primary cause of Startup Death. I’ll say more once the product is public, but it’s 🔥. Or at least that’s what I tell myself, and the feedback has been excellent from those who’ve seen it.

  2. Consultant/Advisor: I’m also doing some consulting and advising to stay connected to customers and customer problems. I have a custom security assessment that I created and deliver myself for customers. It combines technical vulnerabilities and business resilience considerations into a concise, prioritized action plan for reducing the most risk for the least amount of time/money. I also advise companies on both security posture, AI strategy, and go-to-market.

  3. The Podcast/Newsletter: And finally I have Unsupervised Learning the newsletter and podcast. This can best be thought of as the exhaust from everything I learn during the week. All the books I read. All the videos I watch. All the podcasts I listen to. And most importantly—all the problems I see and (hopefully) solve when dealing with real challenges while building, consulting, and advising.

In other words—Building, Helping, and Sharing.

To be clear, this is not all figured out. I have a decent system in place (I think), but it’s not like I’m making millions, or even sitting on millions. No, I’m hustling, and it’s still stressful.

But I’m ok with that. More than ok. I’m exhilarated by it. Because this stress is for something I actually believe in.

I get to spend my time thinking about how to help people. Helping friends. Helping customers. And ultimately trying to help everybody. It’s literally my company’s mission.

To help companies and individuals discover, articulate, and achieve their purpose in life.

The Unsupervised Learning Mission

How I make money in this model

UL newsletter subscribers

Some of you are only here because of the subtitle of this post, which mentioned I’m now making somewhere around $700K / year. Hopefully by the end of this you’ll get a lot more from the post than that, but here are the basic income streams.

People, by the way, have told me not to share this in the past because it’s too personal, or too revealing and the system can be copied. I don’t care. I want people to copy this. I want to free people. More on that in the next section, but first the streams.

  • Newsletter and Podcast Sponsors: When you have a highly intelligent and engaged audience like UL’s, companies trying to get their name out there want to get in front of them. If you’re not huge like multiple millions you can’t really do like Athletic Greens or stuff like that. You have to do specialized companies that make more per sale. Thanks to Clint Gibler of TL;DR sec for lots of collaborations over the years on this. He’s one of the smartest people out there on sponsor management. Honestly the trick is having someone that’s good at it, and who you can pay at least part-time to manage leads, copy, etc. I could write a whole book on this, but there are a million good YouTube videos on doing it well. Annual Income: ~$450K

UL’s paid tier

  • Paid Memberships: In addition to sponsorships, UL also has a paid tier membership that gets people not just the newsletter and podcast, but also access to the community, member content, and lots of other stuff. If you’ve ever heard of “1,000 true fans”, that’s a great way to think about this. Annual Income: ~$130K

  • Consulting: Like I have in the diagram, I created a security assessment methodology and report that I’m really proud of and think provides tons of value. I do like 3-6 of these per year. And again, I’m not sharing any of this revenue with other people. It’s all under UL. Annual Income: ~$80K

  • Retainers: Another great source of income (and stress relief) is having one to three retainers going with your favorite companies/customers. This is where they pay you a certain amount per month no matter what, with the ability to ping you or ask for X, Y, Z at a particular SLA that you agree on. Like jumping on customer calls, writing content for them, talking through strategy with the leadership team, etc. Annual Income: ~$130K

  • Advising: This one is mostly equity. I probably have around 10 irons in that fire, with only 3 that I spend a lot of time on. This one is also great for your soul because you should only be doing this with companies you really love and want to see do well. Annual Income: ~$??? (who knows, they only yield when they IPO and do well)

  • Speaking: This one is a newer stream, but I am having good success with it. I’m looking to do maybe 1 talk a month, with one or so per quarter that’s in-person. I’m currently charging between $7.5K and $25K for these slots depending on a bunch of variables. Annual Income: ~$100K?

  • Courses: Not yet. Maybe 2024?

  • Books: I have one book that came out in 2016, but no immediate plans to write the next one. Maybe 2025 at the earliest.

If you look at the really big people, they’re all about the courses and books because they produce recurring income. I’m just not that cool yet. I’m too focused on building my product right now and courses and books take forever to write and market. One day.

Also, those big people have considerable, full-time teams working for them to make it all possible. I have a couple part-time people.

So anyway, if you add all that up you end up with a pretty good number—especially compared to being stressed out of your mind for half that much. Our projections are actually something like $650-$900 for the year, depending on how things go.

Financial downsides

In this model you’re definitely spending money to make money.

The numbers sound good, but there’s a lot of stress involved on the money side too. The biggest problem is that any of those streams make up a lot of the total, and there is lots of outgoing money as well.

  • If the economy sputters, sponsors will stop buying slots

  • If the economy sputters, fewer people will buy assessments

  • If your retainer companies don’t do well they’ll cancel or reduce the retainer

  • If there’s covid you won’t do as many onsite speaking engagements

  • Etc.

So you always have to be thinking about the incoming threads, whether they’re healthy, and whether you need to spin up others for more resilience to conditions.

Also, there are expenses:

  • Hosting for site / newsletter / etc

  • Hosting / services for product development

  • SaaS tools

  • Advertising the newsletter / podcast

  • Salaries

  • Accountant

  • Lawyers

  • Travel

  • Licenses

  • Insurance

  • Random stuff

This isn’t thousands or tens of thousands a year. It’s over $100K. Plus taxes on top of that. It’s considerable. In other words, this lifestyle is often precarious, at least at the early stage I’m at.

Right now I feel free to work for a couple of weeks from London (yay!). But at any moment I could also be free to live on my buddy’s futon because all my income dried up (opposite of yay).

So that’s the money situation. Now onto my main reason for writing this.

2. Tons of my friends are either miserable at work or are getting laid off

How many people do you know who actually enjoy their work?

This is happening to millions of people in the working world right now, and I’m seeing it everywhere in my own circles. I don’t know many people who are happy to go to work. At least not that have “regular” jobs (whatever that means).

Do you? How many people do you know that have a regular 9-5 job where it’s just a regular company, and they have a regular manager, and they’re happy?

Of course this is multivariate. There are surely lots of reasons for people being less happy at work. Maybe we’re all spoiled brats. Maybe we don’t know how good we have it. But my theory is that it’s largely the following:

  • Companies have realized they gave away too much power in the push to create a “great place to work”. They put snack rooms and off-sites and events ahead of performance for a very long time, and sometime around Covid they realized they’d made a huge mistake.

  • So now they’re clawing it back. They’re doing this through RIFs, Return to Office (which is another way to do a RIF), and aggressive trimming of those who aren’t performing or don’t have the right “anything for the company” attitude.

  • The result is that employees are now seeing through the illusion. They’re like, “Wait a minute…these people don’t actually care about me or my future.” Correctomundo. It’s a numbers game. Or, more accurately, it’s a performance and profit game. It’s all about performance and profit and the rest is hand-waving designed to attract top-end talent and buff their reputations. They treat star players like pro athletes and everyone else like cattle.

NOTE: I’m talking about companies as the machines they are, not all managers. There are plenty of great managers inside these companies that treat their people well. But in my model that’s true despite the truth above, not as a counter to it.

  • RIFs seem to be an accepted technique for cutting costs in many industries now, where as they seemed to have a much more negative hue like 5 or 10 years ago. Again, that could be my own interpretation.

  • So employees are becoming disillusioned, demotivated, and generally depressed. I don’t want to overextend here because anecdata is not data, so I’ll just say that this my impression from not only my own friend and associate circles, but also reading on broader trends.

The result from all of this is that the promise of going to school, getting a stable job at a company, and having some sort of future from that is—or at least feels—more tenuous than ever. I’d have to review lots of data to see if that’s true for sure, but perception is often the reality that matters, and I think that’s definitely the case here.

Now to the broader issue.

3. I believe that the time for being identified by—and tied to—corporate jobs is passing, and it’s time to transition to what comes next

If you ask the average 9-5 worker who they are, they’ll tell you where they work.

How sad is that? What kind of antiquated, old-world, industrial-revolution bullshit is this?

My interpretation of the previous section is that we’re moving into a major societal transition, i.e., the move from Corporate Identities to Individual Identities.

You are not your job. Your worth is not defined by your corporate manager’s opinion of you. You are not your timesheet-punching-performance. Your worth is not whether you read the memo, or used a cover sheet.

Fuck all that.

We’ve had decades—no—generations—where one’s self-worth came from their profession. And not just their trade, but the company where they work. And of course people were also parents and friends and members of society as well, but it’s almost like those were secondary to work.

For all the reasons in the previous sections, I think it’s time for that to end. It’s time for us to think of ourselves as Individuals first.

The problem is the asymmetry of power, where the corporate machine treats the employee like something to be instantiated and discarded.

And to be clear, it’s possible to take Individualism too far as well. And there’s already an unhealthy version of this in primadonas and 100x engineers that cause far more trouble than the value they create. I’m not advocating becoming an asshole and asking for all green M&Ms at your next position.

I’m also not saying all jobs are bad. Work is amazing. I’m very pro-work. Startups are awesome. And there are many great corporations as well. Places where it’s possible to work with a properly dialed-in work dynamic.

The problem isn’t corporations. The problem is the relationship we’ve built over generations around working at them. The problem is our indoctrination into the belief that they are important, and we are the little scrubs that should just be happy we have a job.

It’s lame to quote oneself, but “Fuck all that.”

A healthier way

Think about work like a relationship. It’s hard to be a good partner if you’re not first healthy and independent on your own.

Like I said, there’s nothing wrong with working at a company. Even a corporation. The key is the dynamic between them and you.

We need it to be more equalized. And that doesn’t mean equal. Just more equal. The company’s mission is still what matters, and any employee or contractor needs to understand that.

But it can be more equal. In fact there’s already a good model for it, and I’m sure you’ve seen it before.

Think about how companies treat the named, super-talented employees they have. They get tons of stock. They have tons of leeway. They are listened to in meetings. They’re invited to the table. And they get promoted.

Why? Because the company knows:

  1. They’re very talented, and…

  2. They can go work anywhere else.

The problem with most corporate workers—and indeed most people who can’t find a job or are in constant fear of being laid off—is that they don’t have those two things.

Why is that? I think it’s in large part because of the mindset I talked about above. It comes down to competence and confidence. Look at how different these two mindsets are:

Wow, can’t believe I got a job! I sure hope they like me. Can’t believe I’m really an ACME employee! Can’t wait to tell all my friends! Now they’ll respect me!


Now compare that to this:

Cool, pretty excited to be working on this project. I hope they don’t have me doing any dumb shit and wasting my time. I came here to work with these smart people and actually accomplish something, and if they end up being dumb I’m out of here.


And don’t get riled up because I’m using the NPC language. I don’t even really like the framing. Seems a bit rude. But Holy Shit it’s powerful and descriptive. I am using it here precisely because it’s provocative.

And I’ve been that NPC.

For many years. I’m telling you this because I want you to be one for less time than I was.

So what are you saying?

Put your mask on first.

What I’m saying is that it’s fine to be part of a startup, or a business, or a job, or a corporation. Fine. Not a problem. All good.

But you have to be yourself first. The true version of yourself. The powerful version of yourself. You have to be that named, super-talented version.

And that requires that you focus internally, on yourself.

In other words, you need to focus on your identity. Your mission. Your goals. Your metrics. You have to know what those are. You have to figure them out and be able to describe them to others.

Then you grow your skills. You learn in public. You share things on a website. In a newsletter. Etc. Not so you can become some blow-hard “influencer”.

No. So you can become the full version of yourself. The version that doesn’t hide. And feel shy. And stay quiet when you know the answer.

Once you become that, only then will you be ready to go into a corporate job in the proper orientation. And then you can have a wonderful, healthy, and fruitful stint at the company.

Maybe that lasts 2 years. Maybe you stay for 12. But you do it on your terms, without being treated like a goddamn stapler.


Think of how much better life would be if you were the best version of yourself. This is you restrained at 10%. Imagine what you could do at 100.

Ok, that was a lot. Sorry. Like I said, I’ve been meaning to write this for months. Here are the main points:

  1. Yes, I have a job.

  2. I’m building, helping, and sharing.

  3. And I’m doing it for myself, which is glorious.

  4. And I want you to do it too, because I think we’re leaving the worker-first era and entering the human-first era.

Ask yourself what you would do if you weren’t afraid. And move towards that life.

I’m here to help, and I’m rooting for you. 🫶 


  1. Thanks to Jason Haddix, Joseph Thacker, and Saša Zdjelar for talking through many of these concepts over the last several months.

  2. I want to make it very clear that there’s nothing wrong with just having a regular job and being happy with that. Especially when you’re not defined by your job. What I’m warning against is people defining themselves by a job, where they’re not able to be their true selves, and where they’re in danger of losing that job because of changing times. This is why I’m advocating for this mentality shift. I’m not saying everyone needs to become an “influencer”. I’m saying people need to take on some of those characteristics in order to immunize against the change that’s coming. And the only aspect of influencing that I’m referring to is the aspect of defining and being true to yourself. The time for hiding ourselves and blending into the background is past, because those that do this will become invisible to the machine. And the machine will punish you for it. The machine used to treat those people decently well, and that’s coming to an end. This is why I encourage you to become yourself.

  3. I also know it’s infinitely harder to “do what you would do if you weren’t afraid” while you have kids and a family to support. Sometimes fear is a good thing, like fearing your kids not eating. But at some point, and for many that point came a long time ago, and that threshold passes. And then you have to ask how much better their lives could be if you were the best version of yourself vs. the version you’re settling for. Do not give up on your potential.