6 Mins Read

Defining Your Skill Stack: What Jay-Z Can Teach Us About Strategic Sales & Financial Freedom

Brandon Fluharty |

Brandon Fluharty |


A big thank you to our partners who keep this content free for you:

Ever watch the show Billions on Showtime? It’s about the high stakes game of financial trading…with a lot on the line. Every performer at Axe Capital has access to a mindset performance coach, Wendy Rhoades. When I started working with Amber Deibert in 2019 on my path to a $1.5M-earning year, I described her as my “Wendy Rhoades.” Now, you can work with her too!

Are you looking to break into enterprise sales? My former manager, Jake, is hiring for an Enterprise Sales Executive at Revel Systems. I’ve been super impressed with how the company has evolved since I left in 2017. It’s a remote position, OTE is $260K, and there are tons of great perks (I can attest to them personally). Perfect for the proven MM seller with a strong restaurant and/or retail network that’s ready to break into ENT sales. Apply here.

If you click a link and make a purchase in this newsletter, I may earn a small commission (at no extra cost to you).


⚡️ Today’s level up ⚡️

Today’s edition breaks down the concept of “skill stacking” and why it’s critically important in the progress of your strategic selling career and the pursuit of an awesome life.

Let’s go!

Read time: <7 minutes

If you missed last week, read it here.


Don’t hate on generalists

Be a generalist with your skillset but a specialist with your outcomes.

In his book Range, David Epstein makes an excellent, research-backed case for the power of being a generalist in a modern world designed for specialists.

I won’t get into the details of the research, but if you want to learn more, you can pick up the book or read this excellent summary from Sloww.

It got me thinking about my own career and the value I’ve derived from taking a generalist path to stacking up my skills so that I can leverage them now in a way to design my future very intentionally.

And now that I have the vantage point of working with others and seeing their progression, I want to lay out the concept of “skill stacking” so that you can broaden your range and better take control of designing the life you want.

Sales is a great career path to expand your range

The beautiful thing about sales is there is no linear path to success.

Interview Jamal Reimer, and he will have a different path to sales success than Ian Koniak, who will have a very different path than mine. Yet each of us has been able to use corporate sales as a way to escape the corporate world for good.

That same potential exists in you.

The key is developing a skill stack that you can purposefully use to broaden your range.

Here’s how to think about it.

A masterclass in skill stacking from Jay-Z (w/ a little help from Alex Hormozi)

“Financial freedom is my only hope

F*ck livin’ rich and dyin’ broke

I bought some artwork for one million

Two years later, that sh*t was worth two million

Few years later, that sh*t was worth eight million

I can’t wait to give this sh*t to my children

Y’all think it’s bougie, I’m like, it’s fine

But I’m tryin’ to give you a million dollars worth of game for $9.99”

Everywhere you look today, someone’s either looking for a shortcut or a trying to pawn a hack.

The problem with this short-term thinking is it short circuits your brain and hard wires you to constantly start, stop, and restart. “The grass will always be greener on the other side,” you think. This puts you on a hamster wheel that spins really fast, but gets you nowhere (something I’ve visualized with The Emotional Cycle of Change).

In a talk Alex Hormozi gave last year, he said something pretty powerful:

“The biggest deficiency people have is their expectation. Because we have these very lofty expectations, everyone’s trying to become a millionaire in the next 90 days. If I were to get you to sign a contract that says I promise you that you will be a millionaire in 5 years, but you won’t learn anything for 5 years until you become a millionaire, would you be willing to sign it? Most people say they would, but they don’t live like they would. And I promise you, if you live like you would, you would hit it, but everyone just starts over every 90 days.”

Better to get rich for sure, then get rich quick.

The power of being in sales is that everything you learn compounds.

→ As you start out, cold calling prospects develops the skills of routine and process. You learn how to rack up the “no’s” in order to improve live communication.

→ As you progress in your career, you develop the need to create presentations, business cases, and proposals. You learn how to present value to enable action.

→ Progress further, and you develop ways to get customers to come to you vs you chasing them. You learn the value of designing a category and inspiring a transformation.

Let’s keep going with this concept, because skill stacking creates asymmetrical returns, something you’ll want to get working in your favor.

Let’s say someone likes math in school. They learn bookkeeping in high school at a local hardware store. They get into accounting out of college. Then they learn tax strategy. Then they learn corporate insurance. From there they learn how to structure mergers. Then they elevate to influencing capital markets.

You can see how they change in each chapter and could go from an interest (math) to learning (bookkeeper) to becoming a professional (accountant) to becoming critical (controller) to climbing to the top (CFO) to making it rain (hedge fund manager).

Now for a little fun, here’s how Jay-Z stacked his skills to ditch the Marcy projects of Brooklyn to become a music legend and business mogul.

To carve an alternative path away from drug dealing, he found a hidden talent in spitting rhymes. Then he nurtured that by being able to write lyrics. Then he sold bootleg CDs of his songs out of a trunk of a car. The he got good at promoting himself to get heard and seen. Then he took control of his future by starting a record label. Then he scaled it by identifying other talent.

And of course, his best achievement was learning from his mistakes and being able to stay married to Queen B!

My journey on paper looks anything but a linear progression, but the skills I was able to stack make so much sense in retrospect.

After dropping out of college, I landed at a soccer education startup in Long Island where I ran our 1:1 and small group training. I received what felt like an MBA while getting paid and having tons of fun with great people.

Then, I had the opportunity to become an Account Manager at a music marketing company while DJing at night in NYC. It exposed me to managing timelines and quality service for demanding clients, not to mention how to read a room effectively.

Then after moving to a small town in Florida, I had to reboot my career by selling to SMBs. It gave me the “hand-to-hand combat skills” of selling and eating what I killed. Eventually I moved from print, to TV, to eventually digital marketing where I got introduced to SaaS.

From there, I moved on to an IT consulting firm that focused primarily on mid-market restaurant chains. I was not familiar with the restaurant space, but spending a year shadowing the CEO constructing IT-as-a-Service deals gave me an immersion in how to scale them using technology.

That experience helped me land an Enterprise AE role at a hot late stage startup that focused on restaurant POS. My previous experience helped me hit the ground running and learn how to position more complicated deals to larger brands.

Then the highest I could climb was graduating to pursuing strategic accounts (all Fortune 500 brands). Even though it was a completely new industry for me (Conversational AI and Contact Centers), I had enough strategic thinking skills and experience to leverage all of it to make life-changing income.

Now, I am diversifying those income streams and making business decisions based off of interests and impact vs money. That frees me up to explore the rest of my life on my terms.

I’ll leave you with 3 questions:

1. What is your skill stack?

2. What are your deficiencies?

3. What is keeping you from what you want?

Helpful? If so, respond below with a 👍 or 👎.

See you next week!


Here’s how I can help you right now:

1 | Unlock the 7 Figure Seller OS

Learn how to use design and systems thinking to become a 7 figure seller. There are 3 options to allow you to customize your learning journey.

2 | Download The 7 Figure Open Letter

Get the creative strategic selling strategy that landed a $5.9M deal with a top 4 major global airline. Bonus inside!

3 | Book a 1:1 coaching session right now

You can book a 60-minute coaching session with me (although the Pro above option provides access to 1:1 coaching with me at a 70% discount. Note, just a handful of available coaching slots remain for 2023).

What did you think of this article?

Share this:

Stop Missing Out

Subscribe And Get This Content Straight To Your Inbox

Steal All Of My Guides For Free

Frameworks To Reach Your Full Potential

Steal the spreadsheets, blueprints, and templates I used to design my operating system and have been using ever since.

2022 Brandon Fluharty. All rights reserved.

Skip to content