How Dan Henry Went from Delivering Pizzas to an 8 Figure Online Business.

How Dan Henry Went from Delivering Pizzas to an 8 Figure Online Business.

"Dan, you owe $250,000 to the IRS back Taxes."

“Dan, you owe $250,000 to the IRS back taxes.”

This was the moment that defined me as an entrepreneur, but let’s back up…

My entrepreneurial journey started in my early 20s. I was a young musician that spent most of my time playing guitar and working as a pizza boy.

I spent seven years with the same daily schedule. Get up, research how to be a successful entrepreneur. Go to work and deliver pizza. Come home, wash the grease smell off, play music. Repeat.

Seven years. Seven years of hoping to get a five dollar tip at my next delivery so I could pay my rent…

Until the day I finally cracked.

It was -16°. With windchill factored in, it was -51° in the Chicago suburbs. I drove to the outer limits of our delivery zone. I spent 15 minutes alone scraping the windshield just to get out of the parking lot.

I walked up six flights of stairs because the building had no elevator. I delivered pizza to a man named Gupta. I was sure I would get an amazing tip for basically risking my life to travel through a frozen tundra to get him his medium pizza.

Not only did he stiff me, but he complained the pizza wasn’t hot enough. My manager made me take the entire trip all over again. Yes, even the second time out, I didn’t receive a single penny.

A week later I quit and decided to start my own business.

The next several years were rough. I did everything. I started an Italian ice cart and traveled with a carnival. I then expanded to cotton candy and even airbrush tattoos at birthday parties.

Later on, I started a blog and an SEO agency, and probably several businesses I don’t even remember…

I started to become somewhat successful and even bought my first nightclub.

I thought things were going extremely well. I developed several skills as an entrepreneur, learned how to market online, acquired some sales skills, and things were generally looking up.

I sold my night club for a pretty big profit, and instead of being smart, I did what any young person with new money would do.

I lost it all.

I made a bad investment, went all in on one thing, and lost everything.

Things got so bad at one point that the electricity kept getting shut off. I took my last few dollars and instead of buying food, I bought water bottles and tried to sell them on the side of the road to get the lights back on.

In my final moments of desperation, I started reaching out to business owners and offered to help them with their marketing, for free. I acquired my first testimonials and then started charging for my services.

I landed a client here, a client there, and before I knew it I was getting on my feet.

Within a very short amount of time, I had created a pretty lucrative marketing agency and things were starting to look up again.

That’s when I got the letter. The letter I wouldn’t wish on my worst enemy.

Because I was young and simply didn’t know how to run a business, I had not properly kept my books back when I owned that nightclub, and the IRS said I owed $250,000 in back taxes.

Just when I thought my life was turning around, I got kicked back down again.

The next several hours were a blur. But I remember coming across one article where a guy launched an online course and made $200,000 in a month.

I thought this is my only shot. I know a lot of stuff, I have a lot of skills, people are always asking me to show them how to do things, I have to be able to make this work.

I went into learning mode and read every book, listened to every podcast, watched every webinar, and decided to go all-in on launching my first educational program.

This is when my life changed forever.

That very first month, the program did $100,000 in sales.

You know what it cost me to create that product?

Nothing. Just my time. I was literally just selling my advice. I couldn’t believe how profitable this was…

That’s when I knew I needed to become a master of selling information. It was my ticket to the life I had always dreamed of, and now it was time to make it happen!

Within five months, I hit $1 million in sales.

Over the next few years, I released more programs on various subjects. Mindset. Copywriting. Even how to network at conferences…

I created courses, coaching programs, a mastermind group where people could get more direct access to me, and various other digital products. (Even software for marketing agencies!)

What started as just an idea, grew quickly to over $15 million in sales.

At this point, I looked for the next logical step in my career.

I become one of the best in the world at selling my advice. So I decided to help other experts grow their information business.

I released a book called Digital Millionaire Secrets: How I Built an 8-Figure Business Selling My Knowledge Online.

That book became a Wall Street Journal and USA Today bestseller and helped thousands of entrepreneurs create a business out of what they know.

I then made a radical change in my business. I deleted most of our courses, and decided to only offer direct coaching, where my team works closely with our clients to help them create, grow and scale a digital product business.

Currently, we have helped over 1,000 clients create a profitable online business, and helped over 100 entrepreneurs hit 7 figures.

We’ve helped them raise their prices, charge their worth, and radically level up in a very short amount of time.

Needless to say, everything about my life has changed.

I went from living in broke down rentals with slumlords, to buying my dream home, an 8,000 square-foot house on the water.

So many other things changed along the way as well. I went from worrying about affording healthcare, to easily paying out of pocket for heart surgery that insurance wouldn’t cover, potentially saving my life.

When my son Bruce was born, he had a rough time coming into this world and spent two weeks in the NICU. We didn’t even know if he would survive. I was able to take that entire time off and sit right by his side, hope and praying he would be ok.

If by some chance he wasn’t, I wanted every moment possible with him. I’m happy to report he is now a healthy boy and doesn’t shut up!

Then comes my mother. Every son wants to take care of his mother. My Mom has diabetes, and is high risk for COVID. So when the pandemic hit, it was hard for her to safely work. When I was younger, she always used to take care of me, give me money, and made sure I could pursue my dreams.

So I decided to pay all her bills and buy her a house. Being able to afford care for your family is one of the best feelings in the world.


But let’s be real, as good as it feels to do things for others, you have to take care of you as well.

Most recently, I did the one thing I dreamed about since I was a little kid. My Father would tell me stories of his time working as a Captain in the 80s. When someone bought a yacht, he would sail up and down the east coast delivering them to their new owners.

I always wanted to own my own private luxury yacht, and in December 2020, I stroked a single check and bought one. Not only that, but I even found a way to turn a profit with it. I created a company called MillionaireCruise.com and began offering business masterminds and consulting events on the vessel.

I’ve since sold the yacht, but it was really fun while it lasted.

All this hard work even led to some amazing hidden benefits I didn’t expect. For instance, becoming such an authority in my space brought me invitations to speak on some of the biggest stages in entrepreneurship.

As well, we have won some of the biggest awards in marketing for our work. I was even invited to share the stage with Tony Robbins once!

I’m not telling you those things to brag, I’m telling you them because the first step to becoming successful… is to believe.

My seven years of being a struggling pizza boy could have been shortened to just six months.

I was working towards my goals, but to be honest, deep down I simply didn’t yet believe this was possible. I thought everyone that displayed their wealth was either lying or somehow achieved it by being dishonest.

But that’s when I realized those who are offended by wealth, will never obtain it.

I changed my mindset and that’s when things rapidly turned around.

What’s Happening in My World Now

In 2022 I retired from selling consulting and info products to focus on my new company, CloseDeals.com, where we build and manage sales teams for companies that sell high-ticket products. Other than that, I am always releasing new content, much of it from my paid programs, on my youtube channel.

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