What rebels have taught us about money

Something happens to you the closer you get to reaching financial independence (FI).  With each passing day, you give considerably fewer fu**s than you did the day before.  Your tolerance for old-thinking slowly fades and you start to see things differently.  Even things you were once absolutely certain about seem…different.

We spent the end of 2018 in chill-mode since Baby r&R was out of daycare. Much of this time was spent fighting baby coodies that he kindly spread to us like glitter from a Christmas card.

This much needed down-time also gave us a chance to reconnect and enjoy the first Christmas in our new home together as a family.  It was great watching his wittle voice develop and observing his newfound infatuation with cars and trucks… or as he says it “dies” and “dahtts” cuz you know…C’s are hard bro.

While we try to limit screen-time for our and his benefit, we indulged a bit more than we normally would filling the hours with corny holiday movies and a handful of classics on Netflix, Hulu and Amazon Prime video.  During our binge-watching, we found ourselves drawn to characters and seeing once-familiar storylines in a different light.  Most notably, the story of the rebel.

You know, the one that decided to go left when everyone else went right.  Or the not-quite right lady that risked it all for a crazy idea?  Are they nuts?  Are they selfish?  Are they misunderstood visionaries or is their raging arrogance going to get them or somebody killed?

In some cases, the answer was yes to all of the above.  But in many of the biopics we’ve seen, the rebel was right all along.  Particularly when the the money was funny, the rebel was the one who always came out on top.

There are several examples of this, but we’ll only focus on the few that resonated with us.  Let’s start with Michael Bivins, an original member of New Edition (NE).  If you’ve seen the New Edition story then one of the primary storylines is how he challenged authority, broke away from what was expected of him as a group member and started his own thing.  The outcome was the formation of BBD, an epic run with his own new label that gave birth to other notable acts such as Boyz II Men.

Now we can’t see all of NE’s books but it’s safe to assume that compared to his group members, he’s doing alright for himself which is a HUGE feat in the cut-throat music industry.  Despite NE’s fame, Bivins found the courage to look beyond the screaming fans and “do the math” on their contract while the rest of the group was just “happy to be there” and hesitant to rock the boat.

That rebellious nature afforded Bivins the opportunity to renegotiate his deal from the “traditional” points per album sold model to an ownership model where he had control over his masters and earned more from the record over time.  There’s not much details on this, for obvious reasons, but here’s a quick snippet of a fairly recent interview with Biv and in our opinion, an incredibly insightful perspective on how he developed the blueprint for BBD. Peep the free game below in his Breakfast Club interview.

Let’s change genre’s a little bit though, and take a closer look at NWA and the way their story unfolded in Straight Outta Compton.  In it, Ice Cube, [like Bivins] could sense the math wasn’t adding up and couldn’t quite wrap his head around how the artists were only receiving a tiny slice of the pie.


Like rebels tend to do, he challenged authority, conventional wisdom and the majority opinion of his group members to re-structure his deal.  Unfortunately for NWA fans, this lead to his departure from the group and the creation of his own label.  For Ice Cube, it lead him to cementing his place in the hip hop hall of fame, an incredible multi-decade film career and the fledgling growth of the Big 3 Basketball league of which he is co-creator and “face of the brand”.

Things didn’t pan out as well for his former group members though [for a variety of reasons] but the core message still holds true.  Cube had the courage to step out on his own, believe in his talent and create his own lane during a time where he could’ve easily opted to float down the “gravy train”.

We saw this unfold again as we binge watched Narcos Mexico, a biopic on the Cali Cartel who rose to power in the 1980’s as the largest cocaine and marijuana distributors in the world.  In short, it all starts with a local guy who found the juevos to challenge his place in heirarchy to the regional drug boss, thus leading to the first country-wide conglomerate of regional distributors and a new system that rewarded them beyond their wildest imaginations.

Hey, we’re not saying there isn’t an ugly side to the story, but from a purely leadership standpoint, what Miguel Felix Gallardo did was nothing short of brave, brilliant and yes…rebellious. Even Bill Gates admitted to being a fan of Narcos!


But even if we look outside of the music or drug industry, there are examples of rebellious thinking coming out on top.  Whether it’s Michael Jordan’s revolutionary deal with Nike, Dave Chappelle’s departure from Comedy Central, Oprah Winfrey’s power move to start her own network or pretty much anything Elon Musk touches the message is clear—

your wildest dreams don't come true when you follow the establishment. Click To Tweet

Recently, we’ve seen Tristan Walker take the Bevel brand to new heights with their acquisition, Issa Rae grow her brand with HBO and Cover Girl, Rihanna destroy expectations with Fenty,  Shonda Rhimes chuck the deuces at ABC to join Netflix and Donald Glover carve out his own lane on TV, film and music.

The list of success stories is long, growing, dripping with dopeness and filled with rebels.  Of course, the wildest stories are the one’s we tend to gravitate to, but that doesn’t take away from what these people were able to accomplish.

So what does this mean for regular people like us?

Well, the solution is not to plant ideas to take over the world or to be the next Issa, Shonda, Donald, or whoever else is on your vision board.  I mean, that’s cool if you can but everybody isn’t cut from that cloth. Regular people can learn from these stories,tap into their inner rebel, look at the bigger picture and learn from the trailblazers.

Though you may be fighting battles on a smaller scale, there are plenty of lessons to be learned, especially if your goal is to earn more money than you have in the past or to retire early.

It’s easy to be satisfied with your earnings because you have more today than yesterday or even last year.  The hard part is thinking about and taking action on the possibilities.   That requires courage and forward thinking, not just comparing your current state to the less comfortable state of the past.

This could be finally cutting cable to save yourself an extra $40 a month. It could mean, spearheading the conversation with family to get a family plan for your phone service. It could also mean admitting to yourself that you made a mistake buying that big ass house and you’re not on a path to ‘earn’ your way out of the hole your in. Sometimes, you need to rebel against yourself or what is expected of you by others.

So maybe, it’s time we give rebels the credit they deserve.  After all, many of them are doing pretty well for themselves though they’ll readily admit it wasn’t easy. Maybe it’s time we stop writing people off as crazy for challenging the status quo. And maybe it’s time we all tap into our inner rebel more, so seeing wild and crazy dreams come true can seem…normal.


  1. I just listen to your guys interview on choose FI and went to your blog. I really have enjoyed your material and perspective! I look forward to working through your content.

Leave a Reply