“The key to overnight success is the first 10 years.”

I’m not sure where this quote originates from. I first heard it repeated from a friend of a friend that I met while speaking at Chase Bank in New York City for National Savings Month. The quote resonated with me. It still does.

In fact, if you’ve had the unfortunate experience of hearing me talk recently, you know I repeat it all the time. The quote played a prominent theme in my most recent talk at Google. Technically, the title of my presentation was inspired by Champagne Papi.

While I continue to hold out hope that my mixtape career will have a late-stage resurgence, you can find me here ghostwriting for the illustrious, award-winning Paychecks and Balances to keep my light bill paid and dessert wine bar full. In my nearly four decades, I have been fortunate to go from $5.15 an hour (age 16) to $515 an hour (or more) across a variety of pursuits that now include auditor, author, speaker, writer, and most recently, entrepreneur. Below are a few key lessons (and failures) I learned along the way that I believe will help you map your own path to financial freedom and personal fulfillment.

Step 1: When Others Believe in You, Believe in Them

Opportunity is when preparation and luck collide. Other times, the only key to getting discovered is putting yourself out there to be discovered.

Years of mentoring have shown me it typically takes the average person about three to five years to realize they were capable of accomplishing their goal three to five years earlier. But, it’s hard to teach someone to believe in their own talents (especially the natural talents). Maybe your role is just to be there in their corner patiently encouraging them to realize their own greatness. I know I’m grateful to all the men and women who rooted for me before I rooted for myself.

For example, the path to success I stumbled into is to write a blog you think no one will read (and get named Best Millenial or Gen Z Blog), drop a book no one will buy (and end up on CBS News to talk about it), and drop a personal finance podcast “aint nobody gonna listen to!” as I concluded in 2013 (and hit over 1 million downloads in three years). As my brother-in-law remarks on those with the uncanny ability to fall bass-ackwards into opportunity, “I Forest Gump’d my way through life.”

You don’t have to get it perfect before you get it right. Maybe you just need to get it out there.

Step 2: Find Your Audience

Little known fact, another quote I often reference was originally told to me by my father. In my public presentations, I generically refer to this person as “a mentor told me once…” This isn’t untrue. My father, a former professor himself, was my first mentor.

When I was in my early 20s and suffering a quarter-life crisis about my lack of perceived accomplishments as compared to others on Social Media he advised me to slow down and “Use your 20s to learn, your 30s to apply, and your 40s to teach others the lessons you learned when you were their age.”

To date, much of my life story is more about self-correction than comeback story. I make no excuses. I buried myself in debt. When all hope was lost, I turned to The Man upstairs and the man in the mirror to figure out a way to get myself out of the mess I created. I know I’ve been fortunate. I also don’t believe my story is unique or particularly difficult to repeat with the right support and guidance.

The real chicken or egg conundrum I often face is the existential crisis of, “would I be as ‘wise’ as I am today but for the lessons learned because of the ignorant transgressions of my youth?”

I certainly wouldn’t have written a book, because what would I have written about? Would our podcast exist? Would I have gotten any of the aforementioned press opportunities? Would I have the connections I have today? The network? The friends? The fans?

How deep does the rabbit hole go?

Don’t get me wrong. The lesson here is not that you should only gain wisdom after making the dumbest mistakes possible. However, hopefully, it is comforting to know that even dumbasses like myself are capable of redemption.

Unfortunately, some of us–present company included–only learn our best lessons after experiencing our worst mistakes. While this is a great recipe for writing entertaining blogs and books, it is also a surefire way to make a lot of money living your Best Life while staying walking dead broke.

Rather than waste your time repeating the mistakes of your Senior Millennial mentors, I recommend you become the benefactor of their blunders without paying the full penalty of making them yourself. Live vicariously through us, but don’t live like us. After all, “only a fool learns from their own mistakes. The wise learn from observing the mistakes of others.”

A man who views the world the same at age 50 as he did at age 20 has wasted thirty years of his life. – Muhammad Ali

Step 3: Age Is More than a Number

You can learn a lot in 10 years. You should learn even more in 40.

There is a strangely large number of grey-haired individuals with foreheads permanently etched with wrinkles from decades of abuse at the hands of their furrowed eyebrows. The thought that a young person somewhere might make a mistake brings a Grench-like smirk to their face. These individuals seem to salivate at the idea of running out like an unchained Pomeranian to bark unsolicited advice at any person two decades their junior with completely unhelpful observations that too often contain the phrases…

“Back in my day…”




While I confess there is some internal joy that I feel deep down in my Senior Millennial bones at the idea of yelling at children, I must resist such temptations. I believe I have more to offer than unhelpful reflections of “when I was your age,” which is often code for “I’m about to lecture you.”

Why chastise young people for making the exact same mistakes I made when I was their age? Instead, maybe I can offer insight, perspective, and comfort that this won’t be the last mistake they will ever make, and equally important, this mistake won’t be the end of their world either.

You can lead, you can follow, or you can get the hell out of the way.

To be clear, I ain’t got all the answers. I barely know all the questions. I do, however, have a litany, a plethora, and a MULTITUDE of experiences that unequivocally and undeniably prove what will absolutely not work. My “expertise” is derived from a lifetime of failing again, again, and again after that for good measure.

A man with an experience is not at the mercy of a man with an opinion. – Mr. Ramsey

Step 4: Find Your Inspiration

One of my favorite parts of our platform has become our ability to share and amplify other people’s stories too. This is an incidental benefit that comes from writing for almost two decades and podcasting for over half a decade. I have witnessed the Glo Up of many friends, subject matter experts and guests all over the internet and media. Observing the growth of the freshmen to Senior Class Millennial is pretty cool. I wish I had better words to describe it, but actions speak louder than words. So, check their resumes for yourself:


Hopefully, somebody somewhere will benefit by doing as I say, not following as I did. And, if I am completely wrong, I can find comfort in knowing there are still plenty of years left for me to yell at kids for accidentally stepping on my perfectly manicured lawn when I retire early to a home…down by the river.

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