About Tom & Ariana Sylvester - Parents, Serial Entrepreneurs & Business Strategists

About us

From college sweethearts to a married power couple helping Family Entrepreneurs build the lives and businesses they love.

Meet Tom

Tom of House Sylvester, Second of His Name, Husband of the Queen, Father of the Mini-Mes, Seeker of the Pizza, the Idea Man, Starter of Businesses and King of Call of Duty.

“A super amazing quote to help everyone know how cool I am.”

From computer nerd to serial entrepreneur, I am the definition a “renaissance man”.

I worked 3 jobs to get myself through high school and into college.  I have 2 degrees, an undergrad in computer science and a masters degree in business management.  I LOVE being an entrepreneur, much to Ariana’s dismay, at least initially.

I help people who want more out of life transform their life and business through first clarifying their ideal lifestyle, then building a business that enables that lifestyle.

Meet Ariana

(Pretty sure nothing can top Tom’s bio 😂 )     Animal Lover, Fueled by Iced Chai Lattes, Recovering Control Freak, Mom to 2 hilarious, adorable, maniacal, tiny humans. Movie Watcher, Fantasy Novel Devourer & Sheldon Cooper (Big Bang Theory) fan. Known to sporadically break out in song.

“My husband is crazy and I REALLY like iced chai.”

From a Zoology degree to becoming the secret behind the businesses, I am the brain of all the operations here at the Sylvester household.

As an only child with 2 moms,  I was raised to be a strong, independant & passionate woman. Over the years I’ve had a variety of jobs and experiences that have contributed to my skills & personal growth.

Marrying an entrepreneur (though I didn’t know it at the time) has been one of the most frustrating but also rewarding experinces of my life! And I love nothing more than helping entrepreneurs to find their focus and prioritize their tasks, so they can find a process that works for them while building their business and managing their family (without sacrificing one for the other).

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Our Story

How Did We Craft Our Ideal Lifestyle?

I spent a lot of time at the water fountain that first week (as it was right outside her door).

We began dating a week after meeting when she lured me in with chocolate donuts.

Throughout the next 4 years, we continued to grow our relationship as we worked on finishing our degrees.

Founder & CEO

The Beginning

Ariana was literally the first girl that I met at college.  We lived down the hall from one another and both played soccer.

People began calling us “the married couple” soon after we began dating.

New Life

With college coming to a close, we made plans to move in together and tried to figure out what we would do after college.

We now had $75,000+ in student loan debt, $3,500 in credit card debt and no jobs.

We struggled to find an apartment without having jobs.  Things were getting stressful.

Prior to leaving school, a friend recommended that I read a book called “The Automatic Millionaire”.  That book opened my mind to the fact that we could get out of debt and become wealthy.

The essence was to cut unnecessary expenses (like buying a cup of coffee each day), saving/investing money before paying your bills and leveraging the power of time to have $1,000,000+ by the time you retire.

We ended up finding an apartment that would rent to us.  By the end of summer we both founds jobs and we started working towards our goals.

I quickly realized that a “traditional job” was not as exciting as it had seemed when we left college.

I had a tiny cubicle that I sat in, staring at a computer for 8-10 hours a day.

I knew that I did not want to wait 45 years of working a traditional job to be wealthy.

So I set a goal to “retire” (become financially free) by 35.  That meant that we had 15 years (err.. 14 years) to achieve this goal.

I began seeking alternatives routes to becoming financially free.

I started with the stock market, even though Ariana was nervous, but I quickly realized that I did not know what I was doing.  I also realized that you needed to have money to make money, and we did not have money.

I looked into opening a franchise business but did not have the money for it.

I was getting frustrated and had NO clue where to focus.

Ariana basically said “No” to every idea that I came up with to make money.

I attended some multi-level marketing (MLM) events and realized that they weren’t for me.

I then stumbled onto real estate, but again Ariana shut it down as she “did not want to become a landlord”.

Defeated, I began to give up on my dream and succumbed to the fact that I would not be able to build a business to allow our financial freedom and that I would spend the next 45+ years working for someone else…

And then it happened.



I was driving home from a terrible day at work when an ad came on the radio.

“Sick of your job and not living the life that you want? Do you want to learn how to build real wealth and start living your life? Join us for this limited 2-hour free training on how to become a real estate investor!”

This was it.

I went home and signed up.

Unfortunately, after the first training ended up being a 2-hour sales pitch, and the second training ($500 ticket I split with my cousin) was full of information but no areas to focus on, I was disappointed.

Of course at the end of the 2nd training, they offered their “advanced courses”, which ranged from $5,000 – $30,000. We had nowhere near that amount of cash, so we began walking out.

Then it hit me.  The fear of failing again.

That this was my last opportunity to really make my goal of financial freedom come true.

So my cousin and I convinced ourselves to purchase 4 advanced training courses. The total cost?  $15,000!

How did I pay for it? Well, I put it on a credit card.  A high-interest credit card.  Actually… two credit cards, because I did not have one that much space available.

Oh, and I did all of this without talking to Ariana.

A Bump (Block?) in the Road

Ariana here.

So here is where the story gets interesting…

Up until this point, Tom was on his own trying to start all of these businesses.

I had no interest in being involved, but that came to screeching halt when he decided to spend that $7,500 without asking me!

I could no longer avoid this problem.

I felt betrayed.  I felt confused.  Who was this man that I thought I knew?

We were supposed to be getting married in less than a year. We had just bought a house together.

There needed to be some serious discussions to figure out what the heck we were doing. 

We were SO not on the same page. 

We weren’t even in the same book!

So how did we fix that small problem?

Step 1: Have the tough discussions. After a lot of crying (on my part) and tons of soul searching, we finally figured out that we wanted a lot of the same things in life. But we had very different ideas on how we were going to get there.

Step 2: GET on the same page. That’s where the “goal planning” comes in. At first we sucked at it!  (Tom was always thinking business, I was thinking life.)


As the years went by we continued to perfect our goal planning process. We were aligned on our “Big Picture.”

I saw Tom struggling to work his job AND handle the behind the scenes of the real estate, so I started to help as I floated from job to job.

We got pregnant with our first child.

Tom decided to start ANOTHER business

We made the decision for me to leave my job and stay home with our baby, which freed me up to be present, and also take the reigns on some of the behind the scenes preparations to open our newest venture:

A wine & liquor store.

(Yeap, you read that right)

An “Oh Crap” Moment

Life seemed to calm down for a time. Until I went and had a big ole’ full-blown


Let’s rewind a bit. We had an amazing, rapidly growing little girl. I had settled into running the day-to-day of the 2 businesses while taking care of her.

Then we had a rapid fire of BIG changes all within a little over a year.

  • Tom started yet ANOTHER business (this time it was online, and we started with a blog)
  • Tom started a new job as a traveling consultant (as in fly out Monday morning and fly in Thursday night kind of gig. Every week!)
  • I got pregnant with our second child
  • We “re-branded” our online business, went to our first live event together (my first EVER) & started a podcast

I was pulled in even deeper into the entrepreneur life, and this time it required a lot more from me.

Somewhere along the way, I completely lost

any sense of who or what I was anymore.

Our son was not an easy child. I was sleep deprived, nutrient deprived (breastfeeding & complete lack of self-care) and beyond exhausted.

I was raising a 3 year old and an infant basically on my own during the week, then trying to be a happy wife on the weekends when Tom was home.

I was angry & irritable all the time, then would feel moments of intense guilt. Sometimes I was just sad.

Tom didn’t see it, as I became a pro at hiding it. I didn’t want to stress him out any more than his job already did, and being away from us.

Eventually, that ticking time bomb had to explode.

It was the closest we’ve ever come to giving it all up… 

Founder & CEO

The Next Chapter

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Sometimes, life doesn’t go quite the way you expect it to. I’ve learned that many times now, and this time was no different.

It was HARD making the decision to keep moving forward with the businesses. I wanted so badly to just give up, and go back to living a “normal” life.

Then I thought back to EVERYTHING we had accomplished together. Through all the ups & downs, we had done something amazing.

So we kept going. My meltdown was actually a BIG wake up call for both of us, and forced us to take a good look at our life & re-visit our goals.

MAJOR changes started taking place for us.

Change #1: No more “work-from-home” momming for me. At least, not in the sense that the kids are at home when I work!

Change #2: Intense focus on a plan to pay off debt, once and for all (we invested in a course, kept each other accountable & stuck to it!)

Change #3: Re-defining of our roles in each business, and a setting some solid income goals.

Change #4: Clarity around the bigger vision for our online business, and the essential pivot into the “Family Entrepreneur” space.

And that brings us to today.

We’ve made a LOT of mistakes along the way.

Some things we’ve done the hard way, and we want to save others the pain of going through that.

So that’s our mission. Using our journey & ALL the amazing lessons we’ve learned along the way to do just that.

The rest of the story is still being written… 

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