I skipped last week due to a trip to Portugal. Now I’m recharged and ready to write.

This week, we’ll cover:

Let’s dive in.

Search funds, or ETA, are a relatively unknown shortcut to becoming a CEO.

Most people think the only paths are:

ETA offers a third route. You buy a good business with real customers, revenue, and profits, then acquire it from the old owner.

You neither suffer endless middle-management apprenticeship nor need to invent a product and hope the market cares. You take control of real assets and improve upon them.

Through our self-funded search, Saddletree Partners, my wife and I acquired a group travel business and became owners-operators in 9 months from creating our fund to closing our first acquisition. That is the appeal of ETA at its best. It is not a shortcut around hard work. It is a shortcut to the hard work that actually matters.

The steps to succeed are pretty simple to describe, but much harder to execute:

That, to me, is why ETA is such an interesting path. It lets ambitious people skip the queue and step directly into leadership. But it only works if you are prepared to do the actual work of being a CEO.

FYI: Check the jobs section for a portfolio CEO role at a search-fund like business called American Operator.

Find the Hiring Manager & Their Work

When you’re considering applying to a company, the first thing to do is identify the hiring manager. Often, the title is listed on the job description (e.g. “this role reports to…”). Figure out who that person is; LinkedIn searching for the company name and title name often works.

Find something they’ve done that you genuinely admire and want to learn more about, whether a podcast appearance, a blog post, or a talk at a conference.

If you can’t find anything OR do not genuinely admire them, NONE of the following advice will work. This is because humans are really good at telling when someone is blowing smoke up their ass. So you must have some foundation of admiration to come across as authentic.

To find their work, you can try this AI prompt (with web search enabled):

Reaching Out

LinkedIn or Twitter DMs can work if you can verify the person is active. But professional email is best. Tools like Apollo.io or Hunter.io can help with finding emails.

Then reach out with something like:

“Hi {Name}, your {resource} about {topic} made me rethink how I approach {X}. But I disagreed with your point {Y} because of {Z}. Do you have 15min to chat about it next week?”

This works because:

Find the Hole in Their Thinking

Most people become successful by being right about the world; if you can point out a hole in their thinking, they will most likely want to correct it.

Here’s a prompt for finding that hole - continue in the same chat you used previously:

This prompt can help, but you will get the hiring manager’s time by familiarizing yourself with their projects by actually doing the work yourself to read it and think about it.

Get on the Phone

Once you’re on the phone / videochat, it’s simple. Treat it like a first date. Get to know each other. Talk about the topic that caused you to reach out. Really understand their perspective, especially if there is a point of disagreement between you.

And before you get off the phone, if things have gone well, ask for another 15-20min meeting in 2 weeks to keep the conversation going. Just like getting a second date.

The Second Call

In the intervening period, apply for the job.

When the second call comes around, say something to this effect:

“I had so much fun chatting last time that I actually applied to {role}. I’d love to work with you. But I’m sure tons of people reach out asking for referrals. I don’t want that. I just want to hear about the problems the firm is facing that caused you to open this role.”

Then just do some active listening. Really absorb what problems they’re facing, their causes and symptoms.

Finally, ask for another meeting. (Note: even if this doesn’t eventually get you a referral, you’ve likely earned yourself a mentor. Keep the meeting cadence up and send them helpful things, explain useful perspectives, and generally be a source of value.)

Identifying Problems and Solutions

After the second conversation, contemplate the problems you heard about. You can use this AI prompt to help:

Either way, email the person with an overview of how to solve their problems. More detailed is generally better. Some people worry that employers will take their ideas without hiring them. This does happen at times, but typically just knowing the answer is not enough; the company needs extra labor to implement the solution, otherwise they wouldn’t be hiring.

If you’ve built trust, this shouldn't feel awkward. In fact, it’ll make you the obvious candidate.

Andrej Karpathy, former Director of AI at Tesla and a founding researcher at OpenAI, recently released a new project that maps how exposed different jobs may be to current AI.

The tool pulls data from the U.S. Bureau of Labor Statistics across 342 occupations and overlays an LLM-generated estimate of “Digital AI Exposure.” The result is an interactive visualization showing job size, pay, growth, education requirements, and how much of the work could plausibly be done by today’s AI systems.

Why this matters: Karpathy is one of the few people who has both built frontier AI systems and spent time thinking seriously about how they interact with real-world work.

This project gives us a concrete way to explore where AI pressure will likely show up first. And unsurprisingly, it suggests that a lot of screen-based white-collar work might go the way of the dodo soon.

Here are the 4 most interesting remote job openings I’ve seen this week, all paying $150k or more: