Blogging isn’t what it used to be.

These days, bloggers, unfortunately, are unable to quickly make as much as they did only a few years ago. Personally, I’d launch with a podcast nowadays – but back when I started in 2016, it was relatively common to see a blogger make $300-$500 within a few weeks or at least a few months.

Overall, most bloggers mostly do it for fun. ProBlogger found that 50% of their sampled 1,500 bloggers were earning $100 or less each month.

That’s how my blog started – just me, writing for fun.

Prolly the very same way many of you are thinking of getting started or may have already gotten started with your freelance sites, or created your first blog successfully, or my favorite, quickly setup your profitable membership site.

If not now, when? 😉

For selfish reasons, my blog posts also doubled as a major “cop out.”

You see…my editor at the time was this strikingly beautiful woman. Lucky for me, her editing skills allowed my site to be legible readers – and soon, after we ended up getting married 😍- our story of being on the same page began to spread. We were committed to this “crazy” goal of Financial Freedom and getting our money under control.

A few people were visiting the site but soon there were dozens, and then hundreds, and then thousands, and then tens of thousands, and then hundreds of thousands.


I’m not at the million-mark quite yet, but I bless the earth I walk on that I’m able to enjoy #FinancialFreedom. Not only enjoy it, but also continue to deepen the enjoyment as this lifestyle continues to bring new challenges and new opportunities.

New Opportunities Come From Great Influence

I invite you back in time now with me…

…to 2017

…back at a time…when influence and opportunity were only beginning to meet.

In the past 6 months, Grant, from Millennial Money and I, have been on our own epic money journey. We are pulling together one of the latest, greatest, hottest podcasts out there. We’re beyond stoked with the success stories we see each day so for this post I wanted to dive more into the personal side of this partnership.

(Quick note: I actually wrote this up two years ago, so this is inside the scenes of a podcast that landed in PodBean’s Top 10 Business Podcasts for our premier year! Funny to think I actually hesitated on buying the ‘expensive’ $200 mic.)

I’ll give you a behind the scenes look at working with a serial entrepreneur and the 5 lifelong lessons of great influence from THE Millennial Millionaire.

(If you are not familiar with Grant’s story…then first off, I have to ask: Have you been living under a rock?

If unfamiliar, you can view his background over at

He wrote one helluva book! I was honored to be by his side during the multiple editions Grant had to rewrite to fully polish the content for his publisher. A common phrase I hear lately is, “the power is in the edit,” which I wholeheartedly believe. But, with Grant, I saw it for the first time in action. Props to him for putting in hundreds, if not thousands of hours in this book and his Millennial Money mission.

That’s the true power of a book.

SO MUCH all packed into a few pages because there are teams of editors scraping away the fluff.

If this was a Harry Potter book, sure the fluff is great.

When it comes to money and millennials, we see through that in a heartbeat.

Not only does Grant provide the raw inside details of how he went from $2.26 to a self-made millionaire in 5 years, but he is able to speak to the reader in a very relatable tone – sharing real-life advice along the way when it comes to money and how it mingles in our lives – whether we like it or not. Best of all, he’s done the legwork to incorporate various paths to Financial Freedom, not just his.

Grant is fulfilling his dream to make Financial Freedom more accessible to people everywhere. Mind boggling to think me and him were making this the Podcast’s vision 1,000 days ago now.

Time flies…

…So, my story with Grant.

Where else to start when it comes to 5 lessons…but the beginning:

#1 – Opportunity: Could vs. Would

Life is all about the choices we make; the opportunities we choose to seize vs. those we choose to pass on.

One such opportunity sprung up when I received a Twitter message from this man named Grant. He said he was 30, a recent self-made millionaire, and he was fascinated about the FIRE blogosphere.

After you hit the 6-month and 1-year marks, you begin to see a lot of email as a blogger. I became used to seeing invitations for lunch or drinks in Chicago. Many bloggers visit the city or happen to live nearby so it makes for some excellent networking.

Pictures under Our Stary Tree
Financial Freedom is what you make of it.

As luck would have it, Grant is almost my neighbor, so at first, it was like any other form of communication. We linked up and connected on many, many topics. We have a mutual love for money and for how it works and how others can get it to work for them.

My takeaway from working with Grant is that I developed a deeper understanding of the difference between Could and Would.

Many people say they “could” do this or “could” do that, but most people prefer to talk, talk, talk. You may even know some of these talkers!

“Yes, I would do that,” is a much more powerful message and frame of action than saying, “I could do that.”


Subtle, but could doesn’t imply any effort or willpower will need to be exerted towards a goal or task. Sadly, a lot of us think we “could” do something, but often times, we are faced with the reality, that we “will,” not do those things.

So, quit telling yourself you “could” do it. Instead — whatever it actually is — ask yourself…

will you do it?

As with any frame of execution, there needs to be a strategy, which leads to my 2nd take away from Grant.

#2 – Blue Ocean Strategy

Who wouldn’t want to explore that blue ocean?

Grant and I are both avid readers, so naturally, we’ve connected over a lot of our favorite books. The top book we connected on very early was an old business book from 2005.

The book’s premise is simple: find and create an entirely new market and this way you don’t have to worry about market dynamics from a saturated market with many competitors and players.

Grant’s approach to creating 5-minute podcast episodes was our early attempt at executing a Blue Ocean Strategy. I had not come across such a short format podcast, so I was more than thrilled to be launching something completely new in addition to also launching a podcast.

For more on strategy, check out this excellent recap:

Developing a life strategy is a must. If you haven’t formulated your life strategy, then check on the podcast episode above and get started formulating your life strategy!

Extra points to anyone who can intertwine Blue Ocean Strategies with Your Life Strategy!

#3 – Daily Investments, Highest ROI & Residual Value

Don’t think solely of money but expand further, and ask yourself clarifying questions such as:

  • “What’s my highest ROI right now?”
  • “What daily investment can I make with my money OR my time that will produce a high ROI?”
  • “If the return is high, what will be the residual value?”
  • “Is it a short term high ROI at the expense of a 10x gain down the road?”

These are the types of questions I now ask myself after having spent a good amount of time with Grant.

Our time is extremely precious; so it is best not to undervalue it or underutilize it.

Sometimes the highest ROI is actually some long needed R&R. Sharpening the saw is sometimes more effective than continuously trying to chop down the tree.

More often than not, the highest ROI is straight up SCARY. It might be asking our boss for a raise, or switching careers entirely. It might be launching that side hustle you’ve always been dreaming about or it could be moving closer to your work and saving money by living in a smaller home, like we did.

ROI doesn’t have to be 100% about money. If we couple our daily investments with our strategy, then we lock into a powerful symbiotic relationship. Our strategy becomes clearer as we execute on our daily tasks.

This leads me to my next point.

#4 – Find Your Voice

Finding your unique calling card in life is where the REAL money is.

How many billionaire employees have you heard of in your life?

The answer is zero because true creators, visionaries, and entrepreneurs are people who tap into their own voice.

Oddly enough, Grant was struggling to find his voice early on with his blog. He naturally faced an obstacle in that he is hyper-successful but he’s attempting to give extremely valuable advice to everyone, including those who haven’t started or who have fallen on hard times.

Rather than pander to the audience, Grant doubled down on his strengths.

We live in a hyper-connected world now thanks to technology always being at our fingertips..

To stand tall, on a set of your own principles and values is a bold move, one that we don’t see as often as we should.

Find your voice by tapping into your strengths. Don’t pander to a mass market if it means walking away from your principles and values.

#5- Passion

Passion fuels growth much more than intelligence.

When we’re passionate about the material or the relationships or the career, then we’re maximizing our engagement, which leads to growth, development, and success.

If you’ve ever been, “in the zone,” then you know what I’m talking about.

Grant lives and breathes with passion for all the projects he’s working on. Much of this engagement is by choice. He chooses the projects based on what he is passionate about. He dictates the direction and executes against his strategy.

Compare this approach with the failed approach we all see all the time: Someone is struck with a “million dollar idea,” and tells a few friends. You know the type. He sits on it and talks about how great it will be and how people would truly benefit from such an upgrade or enhancement. Months of talk go by and he doesn’t take any action. And then somebody else invents the product and shares it with the world.

Being interested and being passionate are two things. Find your passion and create more opportunities to further engage in that passion.

Extra points here if your passion involves a side-hustle-money-making opportunity!

(quick tips I found helpful when finding my passion: ask questions such as, “If money wasn’t an issue, what would we do with my time?”, “If we just got back from a relaxing vacation, what type of work would we want to engage in?”, “What brings joy to me and my family?” — it also helps to ask these questions in a brand new environment where the old habits and patterns are unable to influence our answers)

(bonus #6) Stephen Covey vs 50 Cent

We all should give Grant a bit more credit when it comes to his overall music background. Specifically, hip-hop, and to this is an analogy, I like to use between Curtis Jackson and Stephen Covey.

50’s [Jackson’s] approach to living, as outlined in his book 50th law, is essentially, trust no one. We should — based on the book — have full faith in our abilities of course, but trusting in others is a dangerous game. Understandably, he was shot 9 times so his trust issues might be getting in the way of the cooperative nature of business and growth, overall.

Stephen Covey is famous for his 7 Habits of Highly Effective People, where he describes cooperation as the highest level of productivity.

Grant embodies this cooperative approach over individual effort.

Yes, we should do all that we can, but we should also work within teams that engage us, challenge us, and help us grow.

Opening up for further personal and professional growth also opens us up to be exposed and hurt. This is why we need to trust our business acumen and financial savviness when it comes to new opportunities.

Plus, it makes the entire journey much more enjoyable when we connect with like-minded individuals. The online blogging community is a perfect example of an incredible collection of helpful individuals seeking to leave a positive impact.

(bonus #7) More than Just Money

When it comes to entrepreneurship, one would think the lifeblood of a business is the pursuit of profit. Early in my work with Grant, I learned to expand my own thinking far beyond the borders I’d previously set for myself.

Money is merely one of many tools in our toolbox. We have many assets in our lives and many of those assets are intangible things we are unable to hold – such as our relationships, our network, our skills, and our money mindset.

These assets can never be underrated and so I encourage you to absorb the same lessons I picked up from working side by side with a serial entrepreneur: Live your life with passion, find your voice, develop a life strategy, differentiate between what you could do vs. what you will do, and seek out people who will help you grow.

If you take away half of what I did from my time with Grant, then you’ll be well on your way to financial freedom or whatever piece of independence you’re striving for.


P.S. I would be remiss to not mention the greatest influences in my life, my family, so check out the NEW podcast: Entrepreneur’s Happy Hour – officially launching this week! 🙂

My Co-host Kevin and I bring expert interviews, members within our sites that have won that week’s community challenge, along with our take on various topics each week.

My real investor co-host, Kevin is all the way over in sunny Florida hosts this show with me here in Chicago. We love talking about all the ways millennials are side hustling and learning entrepreneurial skills on the side, to maximize their value.

Pin It on Pinterest