My favorite business podcasts for 1099s

I started learning about business in 2010, mostly by reading various business books and business-adjacent books.

What has been fun for me over the last few years though has been listening to business podcasts. There are a billion of them, but here are a few that I keep coming back to.

How I Built This by Guy Raz

Guy Raz, the host, interviews entrepreneurs about their businesses and shapes the interview into a compelling story.

The show has very high production quality and Guy does an excellent job of making it fun to listen to.

For an aspiring 1099, I think you'll be able to relate to some of the uncertainty and doubt the entrepreneurs faced as they were building their busineses but also be inspired by their creativity and hustle to get to where they are today.

Built to Sell by John Warrillow

John Warrilow, a successful entrepeneur who has built and sold multiple businesses, interviews entrepreneurs who have also sold their business.

There are a few things I like about this show:

  • Unlike How I Built This, you get to hear about non-famous businesses and more "normal" entrepreneurs who aren't tech companies or major consumer brands. It's cool to learn a small consultancy can sell for millions of dollars.
  • It does a good job of teaching you what makes a business valuable and sellable to an acquirer. As a 1099 you don't really have a sellable business becaues it's just you doing all the work. There is nothing to sell. But if you were to expand, hire a few employees, build out some systems and win a few prime contracts, that could be valuable to an acquirer.
  • There are lots of stories about how the entrepreneurs got out of some business pickles using tricks, wit, and ingenuity
  • It's also honest about some of the lucky and unlucky things that happen to you as an entrepreneur

My First Million by Sam Parr and Shaan Puri

Okay so this podcast sounds super cheesy just based on the title. That's because it's hosted by these two BROs (I capitalized bros because they are the epitome of bro personalities) who just riff on business ideas and whatever pops into their head into the moment. Sometimes they interview people, and other times it's just them talking about business ideas that could make millions.

As a 1099 it's hard to think of anything that would directly help you, BUT, it's just really fun and the guys are really authentic. You'll probably absorb some ideas sub-consciously that you'll think about another time and maybe apply to a future business.

BUT it's definitely an acquired taste. I'm not a bro so I thought I would hate it but when I'm listening to it at the gym or on my commute I will just burst out laughing multiple times because they're hilarious.


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