Hustle Like a Human

Starting with nothing in New York

Loren's early years read like a stress test. He came to the United States from Australia as a boy, started college at 15, finished before he was 19, and landed in New York City without much of a plan beyond the conviction that he would sort it out once he got there.

Sorting it out meant construction work, bartending, fixing computers, and building websites for anyone who would pay. There were stretches where he was living on a few dollars a day. He describes that period as the thing that turned youthful confidence into something sturdier: not the belief that everything works out, but the belief that there is nearly always a next move available if you keep looking for it.

That conviction is what eventually carried him through entrepreneurship, technology, investing, real estate, and into Business Exits, where he now sits across the table from founders at one of the biggest moments of their working lives.

Why trust tends to win over a long enough stretch

One of the longer threads in the conversation is Loren's argument that business does not have to be a contest where someone has to lose for you to win. He makes the case that being straight with people, telling them things they would rather not hear, and genuinely watching out for the other side's interests are not just decent ways to behave. Given enough time and enough transactions, they turn into an advantage that is hard for a competitor to copy.

It is a practical point as much as a moral one. In a business where most clients sell a company once in their lives, reputation compounds. The deals Loren gets called into years from now will come from how the current ones are handled.

Boredom, fatherhood, and changing what you are aiming at

The conversation also goes somewhere many business interviews avoid: what happens after the hustle has worked. Loren is candid about the pull between ambition and the obligations that come with a family, between wanting freedom and having made commitments, and about the restlessness that shows up when the thing you spent years chasing is no longer the hard part.

The shift he describes is from one question to another. Early on, the question is what am I capable of pulling off. Later it becomes a narrower and more useful one: what is actually mine to do, and what should I let someone else handle or let go of entirely?

What AI might take, and what it might give back

The longest stretch of the episode is about artificial intelligence, and what makes it worth listening to is that neither man pretends to have it figured out. They circle the same question from different angles, agree more often than not, and say out loud that they don't know where it lands.

The worry on the table is skill atrophy. If you hand off the work, do you lose the ability to do it? Loren's answer is that the people most affected are the ones who never built the skill to begin with, because they'll now have no reason to. He also makes the case that some of what we call skill is really just a product of how office work evolved. A generation of people became very good at entering information into Excel and Salesforce so it could be passed around a team, and that isn't the same as being good at the job.

Where both land is on the soft skills. Being in a conversation, actually hearing what the other person said instead of queuing up your next point, and giving a real response is a genuine skill, and one they agree has to be practiced. The open question is what builds it. Is it taking good notes afterward, or is it the moment itself? And if software handles more of the clerical work, leaving more person-to-person time, might those skills get stronger rather than weaker? Neither of them commits to an answer.

The conversation gets personal when it turns to their kids. Loren points out that his own generation was the first to grow up with everything a few keystrokes away, and that not having to memorize facts arguably gave him more room to think. What he'd tell a child now is less about any particular field than about staying curious and learning how to learn, which is what he took from his own liberal arts degree. A friend of his, an engineer by temperament, said he'd push his kids toward creative work.

A case for the trades

One passage stands out for anyone who owns a service business. Loren isn't especially worried about the economic disruption, and he uses food delivery to explain why. A large number of people currently drive around collecting meals and dropping them off. Self-driving vehicles will eventually take that work, and the usual reaction is to treat that as a crisis.

His read is different. The country could support ten times more plumbers and electricians than it currently has, and they would still make a very good living. There's also a question of satisfaction buried in it: whether delivering a meal gives a person the same thing as plumbing a house, building something, or finishing a job they can point at. He asks the same question about manufacturing, and whether assembling phones is really the future worth aiming for.

For owners in HVAC, plumbing, electrical, and the other trades, that's a useful frame. The work is hard to automate, demand keeps climbing, and the people doing it are getting harder to replace, all of which shows up in what these businesses are worth when it comes time to sell.