Welcome back to the Real Conversations Newsletter!

My name is Jacob O’Connor and I’ve interviewed 300+ high performers for my podcast, Real Conversations. Every Tuesday I send out 3-4 of my biggest takeaways from that weeks podcast episode. Short, concise, and never spam.

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Today’s newsletter post is from this weeks Real Conversation’s episode with Sam Parr- The Hustle, My First Million, & Retiring with over $20M by age 31. Know someone who you think might be interested in this newsletter? Forward this email to them (we’d appreciate it 😉).

Sam Parr: The Hustle, My First Million, & Retiring with +$20M

Sam Parr is one of the more unique individuals that I’ve had on the podcast. He has an unconventional way of thinking and a “why couldn’t I do that?” attitude that led him to making a lot of money (by design) at an early age. Here are 3 takeaways from my episode with Sam:

1. Act Fast

One drunken night when Sam was in college in Nashville, Sam and another friend started joking about starting a hot dog stand on campus. Except it wasn’t a joke— the next morning Sam was still thinking about the idea so he went ahead an actually started it. It wasn’t successful, but he learned about a new form of business called “internet companies”.

He googled “where do you internet companies live?” and the answer was California. So Sam moved to San Francisco to try and start an internet company.

He does a few things, none of which are overly successful, but ends up meeting someone running a small email newsletter. This person was making a decent living sending out emails…Crazy…

So Sam thought, “Well if he’s making a decent living off a small newsletter, what if I just made a really popular newsletter? I bet I could make a lot of money”.

And thus, The Hustle was a born. A 6-day-a-week newsletter focused on the Tech and Startup ecosystem.

He didn’t overthink the business, he just went out and started taking action.

2. Run the Numbers

“I talked to a bunch of rich people, and asked, ‘how much do you spend a month?’ and the answer was like $80,000”

Sam knew he wanted to make a lot of money, but how much is actually enough money for him to live the lifestyle he wanted? And how would he get there?

He began asking successful individuals that he knew about their monthly burn. After one conversation he decided $80k / month was the right number for him.

He ran the math backwards and came to the conclusion that if he could sell a company and make $20-25M, then he could invest that money in the stock market and withdrawal $80k / month for the rest of his life.

This works because the stock market averages 8-10% returns annually, and if Sam wanted to spend ~$1M annually, his $20M in the stock market would return ~$2M (10%) annually allowing him to live off the returns.

He went all in on The Hustle and did an extraordinary amount of research. He began learning about copywriting, he was writing a newsletter 6 days a week, he was networking like crazy…

And about 5 years after starting, he grew to roughly 2 million subscribers and sold The Hustle to HubSpot and made ~$25M personally (numbers vary).

3. Cap your Downside

Reflecting on his journey, Sam said he wasn’t afraid to move to California or start these businesses because at a young age he learned about capping his downside.

“Before I moved, I asked my parents: ‘If things don’t work out, can I move back home?’”

They said yes.

He then looked up plane tickets from California to St. Louis and saw it was about $500. So he set aside $500 and knew he’d be ok if things didn’t work out in San Francisco.

He’s continued to apply this strategy in various ways with each of his following businesses.

He’s now an angel investor, owns and operates a few different businesses for fun, and is the host of the popular podcast, My First Million, which had over 100M downloads last year.

You can watch / listen to the episode here. 

You can follow Sam on Twitter here. 

You can follow me on Instagram here. 

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-Do Hard Things & Live a Meaningful Life-