3 Lessons I Learned from Watching Two Millionaires Talk About Money

Having too much money brings a different set of challenges.

That’s one of the takeaways from this conversation between two millionaires. It’s one episode of the “Deep Dive with Ali Abdaal.” This time Ali sat down with Andrew Wilkinson.

Here’s the link to the YouTube episode if you want to watch it.

Ali Abdaal started medical school, then became a YouTuber, and since then has run an online education business. But I didn’t know about Andrew Wilkinson. Andrew went from barista to billionaire, coming from a middle-class family.

“I’m as Stressed as You Are”

For me, hearing Andrew say he was stressed too was one of the most shocking parts of that conversation — right at the start.

We might believe that money makes life easier. But from that conversation: it just brings a new set of challenges. We have to choose our own money adventure and when to stop.

This reminds me of a past boss.

He was a well-known entrepreneur in my city (and maybe in my whole country). He came from a wealthy family and ran more than a couple of successful businesses. But when he tasted the bat soup in 2020, there was no money to add more time to his countdown timer.

I guess money can’t buy certain things. For everything else, there’s a credit card. I’m stealing that from a TV commercial.

“Be a Financial Prepper”

Be paranoid. Only the paranoids survive.

During the conversation, Andrew shared he’s a prepper. Not in the sense of keeping a basement full of weapons, canned food, and gas masks ready for a zombie apocalypse. But in the sense of having multiple income sources.

“Be unbreakable financially”

In 2024, I had to internalize that lesson thanks to yet another round of layoffs in the software industry. I lost my main income source, a.k.a salary. I had other income sources, but not enough to cover my monthly expenses.

Robert Kiyosaki is right: “Build your asset column” and “Make your assets pay for your luxuries.”

I had to truly live it to learn it. Knowledge is only potential power unless put into practice.

“The best way to feel rich is to have cashflow”

Be the Sushi Master or the Chipotle Founder

Apart from the money lessons, my most important takeaway from this podcast episode is to:

“Design your life around your flow state”

We could choose to be the best sushi master of the world — worth a Netflix documentary — or the Chipotle founder.

One has mastered his craft to the point of perfection. Maybe he’s happy having only one restaurant and serving one smallish crowd. The other took a different route and created a reproducible business with thousands of locations, taking himself out of the equation.

That’s success seen from different perspectives.

Both of them followed what they enjoyed doing. Each followed a different adventure.

It sounds like the story of a businessman who ran into a fisherman taking a nap in a hammock under a palm tree. After a long conversation and giving a business plan for free, the businessman realizes that the entrepreneurial journey he was sharing with the fisherman will end with a nap in a hammock under the same palm tree.

In any case, follow your flow state and delegate things you don’t enjoy.


Towards the end of the conversation, Ali started to ask for advice to expand his own business. It was interesting to hear the business and money insights from a billionaire who came from the middle class. It wasn’t advice for everyone, but I took this last part:

“Sell something boring to a rich person. Don’t sell a complex product to cheap people.”