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“I think greed is healthy. You can be greedy and still feel good about yourself.”

That was, no joke, part of Ivan Boesky’s speech to the graduating business class at UC Berkeley in 1986.

I’m just finishing Den of Thieves for the first time, and that’s not only a hilarious thing to say during a commencement speech. It also had me drawing parallels between ’80s Wall Street greed and Silicon Valley’s AI boom today.

If you haven’t read this (very old) story, I’m about to spoil it for you (oh no):

A few months after that speech, Boesky’s massive insider trading scandal blew up, lol. Apparently, feeling good about yourself and staying out of prison are two different things.

The ’80s were a wild time in finance. The market was flying, and an innovation called junk bonds helped fuel a wave of takeovers. Suddenly, buyers could raise enormous sums of money to acquire companies that would have been out of reach before.

There was a lot of money to be made. And when money starts moving that quickly, some people get a little too comfortable cutting corners.

Boesky traded on inside information. Michael Milken, the junk bond pioneer, later pleaded guilty to securities-law violations. They were among the high-profile finance guys caught up in the greed rush (see what I did there). And those were only the ones who got caught.

But junk bonds didn’t force these guys to commit crimes. The boom in high-yield bonds created a lot of opportunity, and a lot of temptation.

Sound familiar?

I get a similar feeling watching AI right now. Money is flying into the space. Every company seems to have an AI strategy, even if that strategy is adding “AI” to its website and hoping nobody asks them to explain how an LLM actually works (silly question, because nobody knows).

It’s easy to get sucked into the hype. Especially when it looks like everyone else is getting rich the best way: quickly.

Now, innovation isn’t the root of all evil. Wall Street is.

Kidding, sort of.

But seriously, this financial renaissance also produced some of the biggest pioneers still driving markets today. KKR grew rapidly during the ’80s through LBOs. Stephen Schwarzman co-founded Blackstone in 1985, using a similar model. Turns out not everyone needed a prison sentence to make a name on Wall Street.

With AI, the shortcuts probably won’t land you in prison. But, like Boesky and Milken, cutting corners can do serious damage to your reputation.

Examples: a website full of AI-slop copy. I’ve literally come across clients with fake customers + testimonials (clearly from AI) on their LIVE site.

Or the client who sends you an email that starts with, “I got that all polished for you, simply copy & paste this into your email…” without realizing they included the AI instructions.

Each shortcut saves a little time or makes a little money. But together, they can chip away at the trust and personality you spent years building.

Turns out your customers notice when you replace your company’s voice with a robot that writes sentences like, “It’s not just electrical work, it’s the pulse of a home.” Yuck.

Instead of killing your reputation, use AI to build a stronger company. Help your team respond to customers faster. Take repetitive admin off their plates. Make your hard-earned knowledge easier for the next employee to find. All this stuff can make your company easier to run, which can also make it easier to sell (and more valuable).

If you don’t know where to start, pay a niece or nephew to help automate a low-risk task you hate (like consolidating your monthly receipts into a spreadsheet) with an AI agent.

AI is so easy to use that it lets us fall into one of our greatest weaknesses: laziness. Don’t become a lazy user of AI or you might just end up in AI jail.

Thinking about selling your business? A confidential, no-pressure conversation can help you identify what makes your company valuable and where to strengthen it. Schedule a call →

Wispr Flow turns your voice into clean, professional text you can send the moment you stop talking. No rough transcription you have to clean up. Actual polished text, ready for email, Slack, or any app.

Speak the way you think. Go on tangents. Change your mind mid-sentence. Flow strips the filler, fixes the grammar, and gives you text that reads like you spent five minutes writing it.

Start flowing free

WOD: “Take a wide stance”

3 rounds:

Rest 90 seconds between rounds. Use a comfortable stance and controlled weight. Swap the goblet squats for bodyweight squats if needed.

founder challenge: the AI automation challenge

Write down five repetitive tasks in your business that AI could help automate. Think meeting summaries, first drafts, sorting enquiries, scheduling follow-ups or documenting a process.

Pick one. Test it this week with non-sensitive information and check the result yourself. Done means you have a list of five and one tested workflow you can improve or discard.

Don’t know how to use AI? Pay a high school kid to show you. Or ask your nephew. He’s probably already using it to avoid doing his homework.

Want a full week of these? Try the free 7-day founder fitness challenge →

This week: a Miami plumbing company with $1M+ in EBITDA.

see how your business would score → take the free Exit Audit

every second counts