Who are Ariana and Tom?

Tom SylvesterTom, Serial Entrepreneur, Husband, Father and Avid Call of Duty Player

Most relationships have two types of people, one entrepreneur, and one rational person.  In this relationship, Tom is definitely the entrepreneur. Tom has a varied background, with formal education consisting of BA in Computer Science and a MS in Business Management, among a variety of certifications.  Tom has worked with a variety of organizations, from startups to Fortune 50 companies, focused on Product Development and Information Technology.  Basically, he is an expert at understanding how to design and create products, from information to software.  Additionally, he has deep knowledge and experience helping organizations and individuals become more productive by removing waste and finding where the remaining time should be focused to maximize value. As an entrepreneur, Tom has started a variety of companies.  Some were not successful, but several were, which are still running today.  It took several years of pleading and convincing, but eventually Tom was able to get Ariana to join him and they now work on and grow their businesses together.

Ariana SylvesterAriana, Reality Checker, Wife, Mother and Chai Lover

If Tom is the entrepreneur, then Ariana is definitely the everything else in the businesses and their relationship. Ariana went to college for the most obvious degree that would help become an entrepreneur… Zoology.  Ok, so maybe not, but that $50,000 education did help when coming up with the name for one of the many failed businesses.  After realizing that a career in Zoology was not likely to happen, Ariana tried out several office jobs.  When she become a mother, she was able to stay home and get paid from the two successful businesses that they had started. As reluctant as she was at the beginning, these days you can find her balancing a baby on her hip, while making some peanut butter and jelly sandwiches, all while managing and automating the existing businesses so that the focus can be on starting new ones.

Our Family

This is why we do what we do.

Family Photo

Our Businesses

We believe transparency is important, especially as you seek guidance and support in growing your business.  Below you can dive deeper and learn more about each of our businesses and how we run them.  We are not just business coaches, we are business owners as well.

Real Estate Investing      Retail Wine & Liquor Store      Serial Startups Business Coaching     Online Business Internet Marketing

What is Serial Startups?

Serial Startups is a community for people that want to start a business to achieve their goals and secure their desired lifestyle.  It is the resource that we wish we had when we started our first business, as it would have saved us tens of thousands of dollars and years of stress, frustrations and mistakes.

Would you like to learn from our mistakes and accelerate your business success?

Every day we meet and talk to people who have a passion and idea for starting a business, but something holds them back.  We also see people who jump from one business to another business, without ever having success in any of them.  To be clear, that is not Serial Startups.  Our coaching focuses on our 3 stage process that we have used to successfully create our own multiple streams of income:

Step 1 – Start & Grow to Profitability

Start one business (or income stream as we often refer to them as) and put in the work/foundation to grow it to a point of profitability.  This requires a lot of work up front, in both working in the business (to make it run) and on the business (to make it grow).

Step 2 – Automate & Continue Growth

Once your business is profitable, the next step is to create processes and systems to automate/outsource your business.  This will free up your time to focus on growing the business and not running the business.

Step 3 – Invest in Your Next Income Stream

One you have money (from building a profitable business) and time (from automating and outsourcing), you can then greatly reduce the time you spend on the income stream and then invest that time and additional income into building the income stream.  Or if you are at your desired income to support your lifestyle, spend less time working and more time enjoying life.

We don’t have all of the answers, but we have had success in starting and running multiple businesses using this basic process.  We believe having multiple businesses, and thus multiple streams of income, is a great way to build wealth, stability and the lifestyle that you want, but we have also worked with many people that one one business, but have created multiple income streams within that business. With that said, through our own experience and coaching a variety of entrepreneurs, we’ve found patterns and strategies that work and don’t work for building multiple income streams. So with Serial Startups, we want to share our knowledge and experience to help you become a successful entrepreneur.  We’ve established a community of like-minded entrepreneurs and invite you to join us on this journey as we continue to not only build our businesses and lifestyle, but help everyone is our community do the same. Along the way, we will always be sharing the latest on what is and isn’t working in business today. We know that you sharing this knowledge, along with the knowledge of our great community, we can all achieve the success that we are looking for.

How Can You Get Started?


Step 1 - Request Access to Our FREE Private Facebook Community

“You are the average of the five people you spend the most time with.” - Jim Rohn

The constant fear and failure while becoming successful entrepreneurs has been one of the most difficult, albeit rewarding, experiences of our lives.  One of our "secrets to success" has been to seek out and surround ourselves with other successful and like-minded entrepreneurs.


Join the private Serial Startups Community on Facebook for FREE >>



Serial Startups Community
Serial Startups Podcast

Step 2 - Listen to the Podcast

Listening to podcasts have changed our lives.  We have met so many amazing people through them, learned so much useful information that has allowed major breakthroughs in our businesses.  Best of all, these podcasts are all FREE, and you can listen to them anytime/anywhere.

This is why you need to be listening to podcasts, as well as why we launched our podcast.  In the Serial Startups Podcast, we share tons of information and experience to help you start, grow and expand your businesses.


<< Click here to listen to our podcast






Step 3 -  Find out how you can Work With Us 


The fastest way to success is to follow and model successful people.  Our goal is to help entrepreneurs of all levels, so we offer different packages based on your needs. How can we Help you grow?



Learn how to work with Tom & Ariana > >

Work with us