Jen Sincero

Q&A: Jen Sincero, Author of ‘You Are a Badass At Making Money’

We sat down with the New York Times bestselling author, who will be reading at Boswell Books in Milwaukee on April 25.

Jen Sincero is a big fan of Milwaukee. One of her best friends lives in Milwaukee, and, in a way, is symbolic of her life journey. They’ve been through it all, from being broke to being rich. Their story began about fifteen years ago when they were both living in Los Angeles.

You Are a Badass cover
Image courtesy of Jen Sincero

“We were so broke, and we were trying to figure out what we were going to do with our lives,” recalls Sincero. “But we lived great lives and we always have fun. We didn’t have money, but we would laugh all the time and tell each other that we were in the Millionaire’s Club because we lived these really charmed lives. We read magazines in the middle of the day and went out for lunch whenever. We were broke as a joke, but we were still aware of the fact that we were working toward our own successes.”

As she entered her forties, Sincero realized she needed to change her mindset about her life choices. She took scary risks and got out her comfort zone. Her journey to being fearless is chronicled in her book You Are a Badass. The book has remained on The New York Times Bestseller list for almost a year and sold over a million copies.

Now, Jen is returning with a sequel, You are a Badass at Making Money. The book focuses on a contributing factor towards her success – money and ways to exploit its growth to the fullest. It addresses how to get rich, using a no-nonsense and down-to-earth style that gets at the root of what prevents us from making the most money we can make. She tries to write in a way that is applicable to anyone, no matter their situation.

You Are a Badass at Making Money cover
Image courtesy of Jen Sincero

These days, what was once a joke between Sincero and her friends has become a reality. And she hopes it can be for others, too.

“To this day, we still laugh about the Millionaire’s Club,” she says. “Every time we’d talk it’d be “Wooo! Millionaire’s Club!’ But we were focused on and very grateful for everything that we had in our lives already. And very focused and grateful for the things we were creating. And lo and behold, we’re both millionaires.”

Prior to her appearance Tuesday, April 25 at Boswell Books, we talked with Sincero about the book and her memorable tour of Miller Brewing Company.

How do you feel about finally releasing the book?

Relieved and excited. Relieved that it’s done. I feel I said everything that I wanted to say in a way I want about making money. I feel it’s pretty good. I’m very excited to have new work out into the world.

What was the biggest challenge of writing a sequel to such a popular book?

Oh gosh. Getting over my panic that it had to be just as good if not better than the first book or that it would live up to it. I finally realized all I have to do is the best job I could do and let myself off the hook, and the words starting flowing. Because before that, I was looking at a blank page for about a week.

One of the things I liked in the book are the pop culture and personal stories to illustrate your points. I think it made it more relatable for me. Did you decide early on to include stories like that?

Yeah. I think my whole transformation around money and my whole life in general has been such a process for me, and I felt that my story and sharing my past fears and worries and failures with people will make it easier for them to relate to and hopefully see some of themselves in. And understand that if I can do it that they can do it. Hopefully they’re funny and entertaining. I think that works the best when stuff is funny and entertaining, so I thought that would help people better digest the material to put it in that kind of package.

Compared to other get rich books, you have a more uncensored and personable approach to your writing style. Can you talk about that approach?

That’s an excellent way to describe it. I think especially since money was a huge, huge, stumbling block for me for so long. I was broke into my 40s. I feel I can speak with a lot of knowledge of being broke and I can also speak about being rich because I’ve definitely done both. [laughs]

Until you give yourself permission to get rich, you’re probably not going to let yourself do it.

Why did you feel there was a need for a more modern approach to getting rich?

Money is something that affects every single person on Earth. I think the more people with a positive, healthy relationship with it, the more good money will do the world. I think this is the kind of book I wanted to read when I was trying to make money. Also, a big part of my book I’m really excited about is that it gives people permission to get rich and I think that’s a huge, huge, piece that’s often overlooked in books about getting rich. It’s all about how to make money and invest smartly and all that. But until you give yourself permission to get rich, you’re probably not going to let yourself do it. It’s such a simple thing, but money is a loaded topic and we have such judgment and fear and disgust around it that I think that’s a very important piece of the puzzle.

How do you think the book relates to people living in Milwaukee?

I actually write about the Miller Brewing Company in the book. Because the last time I was in Milwaukee I took a tour and loved it. And I thought it was really interesting that they coarse corrected when Prohibition hit. I think that’s beautiful story of tenacity and keeping the torch light when times get tough. I thought it was very inspiring.

I really enjoyed that section.

Oh, good. Everybody should take the tour at Miller Brewing Company. [laughs]

For people on the fence here in Milwaukee about getting rich, what’s an easy first step to taking a leap of faith?

Really looking at what money is, and understanding that no matter how you think about it or what you’ve been raised to believe—that money is the root of all evil or that there’s something wrong with pursuing money—to really get clear about the fact that, as a human being on Planet Earth and in modern society—give me money. I think it’s important to stop criminalizing it, and start celebrating it, and healing your relationship and look how you look and think about it, and become aware of all the negative beliefs you’ve got, so that you can start unhooking from them and get out of your own way so you can start making some.

If someone is earning money for more than themselves, like for a family, what’s the most important thing they should know?

That it’s as available to them as they allow themselves to be. That money is really in their control. Everyone has different challenges in their life. Some people have a much bigger challenge when faced with making money. But everyone has the power to change their mindset to take big leaps of faith and to go for it. So, whether you’re with a family or whether you’re single or whatever your situation is, you can absolutely create the wealth you desire if you put in the work and watch your mindset and take big, scary leaps of faith.

So you don’t think there are any limits with someone with a family compared to individuals trying to make money?

Not at all. Lots of people with families make tons of money. And lots of people without families are broke. I don’t think that’s a deciding factor. Again, you may have more challenges, but I think it’s totally available.

For someone wanting to create their own business, have you found common paths to getting rich?

Yes. If you want to start a business and want to make money, you should get yourself educated, read as many books about making money as you can, go to seminars, invest in yourself, hire coaches, take classes, be brave and do things that scare the crap out of you on a regular basis. You don’t remain anywhere by remaining in your comfort zone. So, pushing yourself and stretching yourself to do things you’ve never done before that are outside your comfort zone is usually important.

You don’t remain anywhere by remaining in your comfort zone.

In the book, you mentioned the examples of Prince deciding not to open for anyone after getting booed by the Rolling Stones crowd and Jim Carrey writing a check and going after his goal. For Milwaukee musicians and comedians who want to be successful, what’s the most important thing to know?

Find out how other comedians and musicians are making money. I think a big culprit with being an artist is we hope that we can do what we love and the money will follow. Do what you love. Focus on income streams and the money will follow. So, if you want to be a professional musician instead of being a hobbyist, figure out how to monetize music. See how other people making money on music are making their money. Same thing with comedians. I think with the arts it’s about not being squeamish about making money with it. There’s a big stigma about it that you’re a sell-out or somehow not a real artist if you’re focusing on money. Focus on the art and the money. It’s doesn’t need to be an either/or situation.   

What’s your favorite thing about being a life coach?

Seeing people wake up to their own greatness and completely change their own lives. That’s one of the most exciting things I’ve ever witnessed.

Writing = ass + chair. Some people want to write it but don’t actually want to sit down and do it.

If people want to write a book, what are some of the most important things for people to know?

Writing = ass + chair. Some people want to write it but don’t actually want to sit down and do it. So, the big mystery is sitting down and doing it for a lot of people. And write all the time so you develop your voice. Keep showing up, keep writing. Keep showing up over and over and your voice will get clearer and clearer. You have to be brave about taking risks and saying things that you’re kind of scared to say. Because those are the things people will relate to. Playing it safe doesn’t really work as an artist. Writing in chunks is a great tip as well.



Joshua Miller covers music and culture for Milwaukee Magazine. He also writes for various other outlets in Milwaukee, Madison and Chicago. You can follow him at @JoshuaMMillerWI.