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Asking My Richest Friends How They Made Their First Million

So I FaceTimed my richest friends for life advice. I wanted to know how to make a million dollars based on their personal experiences.

I asked:

The first question I asked them: How did you make your first million?

Here’s what they had to say…

Asking My Richest Friends How to Make a Million Dollars

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Neville: Multiple Income Streams Add Up

It’s honestly kind of boring.

I had a company called House of Rave in college that was making me a couple thousand bucks per month and then AppSumo was making very good money. And then also I have a company called Copywriting Course. So I had multiple income streams that all started adding up and at the same time I was also maxing out a Roth IRA and my savings account and all that kind of stuff.

And slowly one day you just become… You hit that number.

David: Sold His Company

When I sold Grasshopper, I never had money before that. I just had enough money in the bank to have living expenses, live where I wanted to, have the car I wanted, but I never had like, “money” money.

We sold for $175 million.

Nick: You don’t know when you become a millionaire

I had a web hosting business when I was in high school and college, then I bought some stocks, and then I worked in an avionics business, and my family company.

I don’t exactly remember the EXACT moment that it went over to $1 million until you actually sell the business. Oftentimes you don’t know that it happens.

Neville: Your money is spread out

In my case, I didn’t know the exact moment I became a millionaire because your money isn’t just in a checking account, right? Your money is spread across like a Roth IRA investment account or something.

So if you have a Roth IRA and it increased by 25% because some stock did really well — well technically maybe now you’re a millionaire, and you just don’t even know it happened.

Any advice for people that are trying to make their first million?

David: Don’t worry about the $1 million dollar goal

First of all, I wouldn’t worry about that goal specifically.

Instead, how do you have freedom of choice and what amount of money would that take?

But I’ve found that it’s really investing in yourself. That doesn’t mean you can’t have a job or do things along the journey, but people that make a lot of money have invested in themselves — either in their own business, or building their own things. It could be a portfolio of real estate, it could be a hundred other things, but it’s all themselves.

Neville: Why do you want $1 million dollars?

I remember even thinking, why do you want a million dollars?

And I think the reason is just security, stability, and all that kind of stuff.

And I think it’s cool to have a number there to hit, but then once you hit it — it’s almost like a lot of goals in life — you’re kind of like that was neat… Alright, keep moving.

When did you realize you were rich? Because I think there’s a big disconnect between when people are millionaires vs. when they’re actually RICH

Nick: Didn’t need to rent out his apartment anymore

I had an apartment in New York City that I was paying a lot of money (like $5000 a month) for and I was trying to rent it out every night for friends that were visiting, and a friend of mine was like, “Why are you trying to get a couple hundred dollars, you have all this money? Just give it to your friends!”

Tynan: Automating his finances

I always wanted to automate my finances. My money came in from various little projects and I had to pay off my credit card (I pay off all my credit cards every month), but I didn’t know for sure that I had enough money in my account to cover it, so I would have to check every month: How much are all the bills? Do I have to take money out of some investment or something like that?

And then once I got to the point where that could be fully automated, then I felt like I never had to worry about money again, and I could just kind of do whatever I want to do all day.

David: Having more freedom

I think there were two times:

  • Knowing that I had freedom to do things. I could go on vacation and know that within the business, someone would do the stuff I needed to get done.
  • And then to be able to make choices. If I want to go somewhere and just pay for it, I can. I can go to Greece for two weeks, or go somewhere and stay anywhere I want.

Neville: Spending $920 on a plane ticket to Vegas

One time, I was going to a last minute bachelor party in Vegas, and I was like, “I don’t care what it costs, I’m just gonna buy it.”

The ticket was like $920 and I was like… “Oh wait, I can afford it! I’m just gonna do it.” Whereas before I’d be like, damn I can’t go.

That made me feel rich.

And it wasn’t so much the money. It was just that access and freedom that I didn’t even have to worry about what it was going to cost. That felt really good.

Who is the happiest person you know?

Neville: My friends who work regular jobs

A lot of my friends that have regular jobs. They have a great life, they make a good amount of money, they work in a great job, they work with cool people, they have kids, and a dog… And I think that’s pretty great. It’s pretty awesome. That’s a dream.

They find happiness in whatever they do.

Tynan: It’s about your perspective

What I’ve found is that it’s really a matter of perception.

It’s not even so much about whether good things are happening to you or are bad things happening to you — it’s about how you’re weighting the things that are happening to you. And how are you perceiving them?

Are you focusing on the positive things or are you focusing on the negative things?

For me, I forget what even prompted this, but I had this idea that whenever anything bad happened to me, I was going to find something positive about it.

So if I had a dog and the dog died, I would think like, “Well at least I don’t have to pay for food anymore, right?” So I wouldn’t be glad my dog died, but you find a positive thing.

I did it for a month, and I felt like it had some impact. And then I did it for another month. And then I kind of forgot about it in the third month. I was like, “Oh man, I used to do that,” and then as soon as I thought about that part, I automatically also thought, “Yeah, but now I have more time,” and I realized… Wait, I’m just doing it automatically now.

Neville: Happiness ≠ Money

I don’t think it has to do with money that much.

I mean, it helps to have your bases covered, right? Money can’t buy happiness, but it’s really hard to be super happy without a lot of money. You have to have some sort of resources to cover yourself.

But because it’s all invested somewhere, or you have it in a savings account — you’re not actually spending a million dollars.

I think when you’re a kid, you think you’re going to make a million bucks and you’re going to spend it on cars and shoes and whatever. But in reality, it’s not like that.

I think as a reward, I bought myself a KitKat bar or something.

Do millionaires have morning routines?

David: It’s not about the routine, it’s about making the time

I think morning routines are very dependent on the person.

I have ones that are probably not typical. I wake up and read my phone in bed — which everyone says not to do.

But I think the most important thing is having a routine and scheduling time. Because we have a limited amount of time. So I write my weekly newsletter, and that’s on my calendar. I block it out the same way I block out my morning routine for the gym.

Neville: Anti-morning routine

I try to wake up as late as possible.

I try to lay in bed as long as possible.

The new thing is, now I just play on Twitter in the mornings and that’s kind of fun and look through photos of dogs and stuff like that.

I don’t have a morning routine other than I try to drink caffeine at some point on weekdays and I try to stay in bed as long as I can.

I don’t know, it’s different at different times in your life, right? When I was 20, who the hell knows what my morning routine was! But I think when you have kids and a dog and a wife and all that kind of stuff, there has to be some sort of routine to get everyone on the same schedule.

I can totally see that happening in the future — but if you’re just by yourself, then I think your routine can be whatever the hell you want it to be.

I don’t think there’s any set routine. I personally don’t have one.

Oh, there is one thing. I moved all my appointments back to 1 PM so nothing ever starts in my week before 1 PM.

Key Takeaways

So what it comes down to, is that there’s no one way how to be a millionaire.

Neville became a millionaire by having a bunch of different income streams. David became a millionaire by selling a company that he co-founded.

And being a millionaire means different things to different people! For Nick, it was not renting out his apartment anymore. For Tynan, it was being able to automate his finances and not worrying if he had enough in his account to cover it.

What everyone seemed to say, is that it’s not about the million dollar goal — it’s about having freedom. Freedom of time, and freedom of choice. So if you want to be a millionaire too, focus on making freedom the goal, and maybe you can live like a millionaire a lot sooner than you think.


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