When you think about your retirement, what does it look like? Where do you see yourself and your family living? How does your partner feel about your plans? Have you even discussed this before?

These are all tough questions and decisions that Tom Sylvester and his wife Ariana had to answer. He was absolutely sure he wanted to build a business, he wanted to leave his office job to spend more time with his family, and more than anything: he set a goal for himself to retire by his 35th birthday.

Today, they have built three different businesses: real estate investing, they own a wine and liquor store, and they also have a coaching and consulting business for entrepreneurs. It’s thanks to this that they were able to leave their jobs and to really design their own schedules.

But getting to that point wasn’t easy. 

Before anything happened, he had to get his wife on board with this idea. She just kept saying no, until Tom was desperate enough that (and he does not recommend doing this!) he spent $8,000 on a real estate investing course without even telling her. But once they talked about it and had all the tough conversations that needed to be had, it all worked out for the best. They got aligned on what they wanted the future to look like. After that, it was just a matter of finding out how they were going to make that happen.

Getting started…

If this is your first business, you need to realize that it won’t always be perfect or easy. 

We asked Tom what is the most common obstacle that new entrepreneurs face, and the answer was: lack of clarity.

And this goes for many different areas. 

Lack of clarity in what they want their life to look like. A lot of people will build a business and even if they have a successful business, it doesn’t mean it’ll make them happy.

Lack of clarity in what their customers need. Not understanding your customers deep enough will stop you from solving their problems.

Lack of clarity around what the next problem they need to solve is. Coming up with a name, getting business cards or a logo should not be a priority. The first thing you should be doing in your business is figuring out who am I going to serve with this business and what problems are they facing?

SOPs and systems are extremely important

At the beginning, you’re probably wearing all the hats, trying to keep your business afloat while wearing yourself out. The question is: how can you back out of the daily operations and keep your business growing at the same time?

The most effective way for people to do this is to do it small and consistent. We recommend having a weekly meeting that serves a couple of purposes:

To reflect on the last week and ask your team what went well, because we want to celebrate the wins and understand what’s working because we want to do more of that.

We also want to ask what challenges did we face. Pick the top challenge and the next week, work on solving it. 

This will help you to consistently improve your business in small steps so that every week you get more momentum. Eventually, it’ll allow you to automate or delegate things that you need to get off your plate.

Choose your focus

There are three things you really need to focus on in order to keep your business growing.


Eliminate activities that you don’t need and will give you time and money back. 


For activities that are essential, but are being done inefficiently, you can use tools to automate them.


Finally, you can bring someone in and get them to do tasks that can’t be easily eliminated or automated.

What is the best way to delegate?

Tom says that you can delegate a single project or even just a task when you’re just starting. Giving up control of everything is not easy for most people and it might seem like a big step. So just take one single thing and work on delegating that to someone. 

This way you’ll also be able to figure out if that person is a good fit for you and your team. If they are, you can delegate more tasks to them and keep adding responsibility. And if it doesn’t work out well, you can learn from it. Ask yourself what went wrong and how it can be improved with the next person.

He mentioned that when you’re delegating, it’s more important to find a person that you’re comfortable working with and likes the vision you have for your business, rather than just focus on skill sets.

A lot of people come up to Tom and share their fears of giving up control. They think they’re not gonna be able to run their business properly and customers might not get serviced the right way. The first step is to figure out what is the reason for this concern. Tom likes doing an activity called Five why’s, where you basically keep asking “why” to get to the bottom of the problem.

Coaching, Podcasting, and Books

Tom worked as a consultant with many Fortune 500 companies. He got to travel all around the country and meet amazing leaders. But once kids came into the picture, Ariana and he sat down and discussed the future. He realized he didn’t want to continue traveling 5 days a week and needed to stay with his family. 

But around the same time, people reached out to him and ask him questions about running a business. And this was an eye-opening moment: all these systems that they had put in place for their businesses, and planning their future, were actually valuable to other people. 

So they started a podcast to reach out as many people as possible, called Lifestyle Builders. They also have a book coming up, which will be a step by step guide of how to get clear on what you want out of your life; how to get your finances in order and start your business, put systems in place and scale it.

What Does Retirement Really Look Like?

When Tom set the goal to retire by 35, he didn’t really know what it looked like. He didn’t have a plan or an expectation. But he realized that retirement to Tom and Ariana is about having options and being able to do the things that make them happy. Because when you finally achieve success, it’s easy to get depressed or lost because you don’t have a driving factor. 

This isn’t the case for them, because they thrive on taking new projects. Books, podcasts, coaching: they want to make an impact on the people around them. Being able to see how much they can help other people change their lives and achieve success is their focus. 

His final word of advice is: don’t try to be like him. Be like yourself. And focus where you spend your resources, your time, your money and your energy. Because that’s what gets you to success.


To listen to the full interview with Tom go here