The Hive Five Podcast

5 Key Takeaways from Tom Sylvester

1. Success starts with you. (Analogy: In the case of an airplane emergency, you have to put on your own oxygen mask before helping those around you.)

2. Clarity is a major productivity hack. Be clear about what you want.

3. Make sure you select a business that supports your life goals.

4. Don’t fall in love with your product or service, but instead fall in love with your customer.

5. Be proactive in creating an environment that will help you succeed.


In this episode, Keagan sits down with Tom Sylvester from Lifestyle Builders. They focus on the importance of work-life balance, creating a company that can help you accomplish your life’s goals, and Tom’s passion for helping other entrepreneurs.

Tom Sylvester has a wide background in many business ventures since graduating college. He met his wife, Ariana, in college and when they graduated he decided that he didn’t want to work in a cubicle for someone else for the rest of his life. So, he set himself a goal, that by 35 he would be retired. After Tom graduated, he tried many different things. He started a real estate investment business, but while he was doing these side ventures, he was doing corporate work in software development. Tom and his wife also opened a retail liquor and wine store. Through all of these different business ventures and more, he and Ariana were able to both leave their full-time jobs by 33 in order to focus solely on their personal businesses.

Tom and Ariana have made it their mission to build a movement of “family entrepreneurs”. Entrepreneurs that are building a business in order to provide for their family and provide the necessary level of freedom and independence that owning a business provides. However, they also help entrepreneurs who may have strayed from the initial reason of “building a business for my family” and are focusing so much on their work that they are neglecting their family, and they help redirect the entrepreneur’s expectations and focus.

If you are interested in work-life balance, building a business in order to benefit you and your family, or in nailing down your goals for you and your family, this is an episode for you.


Click Here for Details (Computer Generated – May Contain Errors) ▼

When the going gets rough, you know how the saying goes. Sometimes things happen, life happens, and it’s not always our fault. In this podcast, we’ll feature real life testimonials from people like you from good times to bad, funny memories and heart lessons learned. Everyone has a story and everyone has been there for business owners to parents to young adults. The high five aims to tell stories about overcoming the struggles of adulting while celebrating the little victories of life in each podcast. Our guests will give insight to five key takeaways from someone who’s been there and done that, leaving you better than when you started. Thank you so much for listening today. My name is Kagan Henson with bright B, and we are here and have the honor to speak with Thomas. Oh Sylvester with lifestyle builders. How are you, Tom?
Well, doing well. How are you doing? Hey, doing good. Thank you so much for being on today. Yeah, absolutely. It’s a pleasure. I’m looking forward to it. Oh, fantastic. Well, I know we just met a few weeks ago and really appreciate you reaching out to me on linkedin. Usually I don’t respond to people on Linkedin, but for some reason I responded to, you know, I get that from a lot of people and I don’t know, I must just have some aura that I sent through the computer. It must be, I don’t know, maybe it’s, maybe it’s a that you’re, you have a picture of you and your wife on there. Maybe it’s just a little bit more welcoming than, than most at. Well, I must be doing something right then I guess. Well, Hey, I want to start out and I, we just want to really get to the nitty gritty and, and talk about, uh, you, uh, when you first started.
So I have read and my team has read a little bit about you and it’s very interesting that you seem very comedic and also looks like you and your wife have a phenomenal relationship and we just want to talk a little bit about where you started. Like let’s just dive into where you began on this journey that you guys are on. Yeah. It’s uh, it’s interesting. So essentially my wife and I met the very first day of college and we had four years of college together. That was great. And then as we were getting ready to graduate, basically I started looking ahead and I had a um, software development degree. She has a degree and I just started looking ahead at our life and I was like, you know, I don’t want to be working in a cubicle for somebody else for 45 years. She was having trouble finding jobs was to allergy.
So I just basically set a goal before we left college, just said by 35 I want it to be for us to be retired. And Yeah, the time, I had no idea how that was going to happen. But I said, well, if I set that goal, that’s going to give me enough time to figure it out. Right. And so basically after we graduated I started trying everything I could to make this work. A whole bunch of things didn’t work out, but we started finding some things that did and just started opening different businesses that did work out, which eventually led us both. Leave our jobs, um, by the time we turned 33.
Okay, so you got to tell me a little bit more about all these jobs because I do see multiple different things that you’ve done. So just give us an idea of what you’ve done recently.
Absolutely. So, uh, on my, we’ll call it my professional career track, I started out as a software developer and that got into real running projects, running new products for this company and then really getting into just um, productivity and how teams and people and businesses can be more productive. And then that eventually led me to go into consulting where I was working with other really large, like fortune 500 companies I was brought in to help them launch new products and improve their team productivity. But what I ended up figuring out was that a lot of times I had actually worked with the leaders of these companies to change their style of leadership and to really shift their business strategy to take advantage of the improve productivity. That was.
And on the side when I was doing, I ended up starting a real estate investment business. We’ve had that for about 10 years along the way, as most entrepreneurs do. I saw another opportunity, so I ended up opening a retail wine and liquor store and then, uh, the two kinds of worlds came together as we started having a lot of entrepreneurs reach out to us, asking us basically for business guidance and advice, not just business, but also how we were able to have my corporate career, my businesses. Um, we have two kids. I’m married and they were like, how do you get all of that done while also not letting it take over your life? So that was basically when my wife and I said, you know, there’s a big opportunity to help other people like us and that was really shifted into working with entrepreneurs and small business owners to help them not only build a business but build a business that ultimately supports their life.
So let’s talk about this because one of the things that you say on your website, a tom and [inaudible] dot com, correct? Correct.
You call it family entrepreneurs. And I find that very interesting now from looking at your website. I mean, you are definitely very family oriented. It looks like you included your, your kids even in your business. Just a, one of the pictures we resolve I think was at the liquor store potentially that, uh, that your kid was watching something on maybe an ipad or something, I’m assuming probably while you were working. Yup. Yup. That is, that is hilarious. Well, uh, and, you know, with my kids as well, I really tried to involve them as well and in my business so they can experience experience it and mb with me at the same time, but talk to, talk to me about this family entrepreneur lifestyle. What does that look like?
Yeah. So kind of the way we got into this. My wife wasn’t originally in the businesses, she had a job and she was just Kinda, this is your thing. And then eventually as we started kind of talking about what it was we want our lives to look like we were getting ready to have our first child. Um, she’s like, you know, it’d be great if I could stay home. And I’m like, absolutely, that’s what I want for you. And so, you know, we started kind of planning things to make that work and as we were looking around for different strategies of how to do that, well we ended up finding was that a lot of entrepreneurs didn’t talk about, you know, their family or how they kind of manage everything. And then what we found was a lot of the entrepreneurs were actually single, um, or they were maybe in a relationship but they didn’t have kids.
And so we were facing a lot of challenges that we didn’t really see people talking about. So we realized that there was a gap in the market that we could actually help other people like us. And so we definitely weren’t perfect as we started. We’re still not perfect, but a lot of the people that we talked to, when we asked why they were building a business, they said, well, I’m building a business to create a better life for my family. Yet when we actually looked at what they were doing, their business was actually taking over their life sometimes leading to things like divorce. When it was very ironic that most people wanted to build a business to support their family, yet their family was kind of like falling apart while they were trying to make that happen. So what we really said was, you know, we’re kind of figuring out how to do this and we want to help other people to do that because we don’t want to see families because this entrepreneur wants to help their family but doesn’t know how to manage the two while they’re doing that.
How many times to use do you hear that? Where an entrepreneur comes in and he’s like, I’m doing this all for my family and it looks like it’s in champagne.
It’s, it’s far too often. It’s way more often than I’d like. And um, you know, I don’t think a lot of people realize that there are ways to do that and you know, just naturally, most entreprenuers we kind of have this like go all in attitude. So like I know for me personally, when I started a new venture, I’m like, here’s the idea, I’m going to go in and I’m a start making a work. Whereas my wife, for example, is more of the, alright, well let’s sit down and let’s kind of plan things out. And so oftentimes what ends up happening is that the entrepreneur doesn’t take enough time to articulate why they want to do things and you know, how it’s all gonna fit together and that’s a lot of what ends up pausing the issues, you know, between their spouse and with their family because they’re just kind of off to the races all in and not really involving their family in, in part of that and how it can all fit together.
Yeah, definitely. And I mean, you’re really speaking to me as well because it seems like my wife and I are continually trying to communicate what’s going on in the business world and what’s going on in the family and trying to tie that all together and you know, with bright B and, and starting starting this company, uh, the, the challenges are, it’s amazing. It’s just overwhelming. You know, it’s, it’s one of those things where you feel as if sometimes you can’t get out of it, uh, you feel like you’re stuck and you know, that’s definitely not where we want to be. But I think that’s where we end up a lot of the times. And why, why do you think that is?
You know, a lot of it I think comes down to it. It really comes down to two things. One is expectations and alliance. I’m far too often whether it’s, you know, in a relationship, like a personal relationship or even in a business relationship, we don’t do a good job of communicating our expectations and then talking to the other people and say, what are your expectations and getting aligned on those teeth ends up happening. When we don’t do that is that different people have different visions. Especially for a lot of entrepreneurs. Like we have a vision in our head and sometimes we have trouble articulating that to the people around us. And then as a result, as we think we’re moving forward potentially on the same page, what often happens is that we’re actually moving in different directions or at b, don’t realize it until it’s far too late and you see these big issues coming up. So a big thing that we do with a lot of people as we have them define expectations, other right them is and backing that up and basically figure out where things aren’t aligned at the beginning. And then we put a process in place that basically lets continuously check in on this and when we see it start to get off, let’s figure out ahead of time how we’re going to get it back to back way. We never run into these major issues or major problems and we can basically detect them ahead of time.
So do you find that both spouses or whoever’s in the relationship is uh, willing to, to sit down? Or do you feel like there’s some, some tug on, on one side or the other or unwillingness perhaps?
Yeah. You know, we see, we see all different things. Unwillingness comes up. It’s usually because there’s some sort of fear and oftentimes entrepreneurs are overwhelming, you know, we have a lot of ideas and we’re thinking differently than, you know, most of the world. So when we’re bringing these things up, it can easily overwhelm a spouse, especially if they’re not an entrepreneur. I’m so one of the things that we found is that entrepreneurs have to actually listen. They have to ask some of these questions and it might not all come out right at once, but by asking the questions and listening, you can start to get a little bit of light into your partners, kind of where their head’s at with some of those fears are, and then work through that. Um, the other thing that I really found to be beneficial is talk about why you want to do things, not just what to do.
So often times as an entrepreneur, like I know I did this wanting to start a business and all she saw was, okay, well this business is going to cost us time. It’s going to cost us money. That all sounds like a negative. Like what are we getting out of it? And once I shifted away from talking about starting a business and move towards, Hey, this is the life that I want us to have, what are your thoughts on it? And once we get aligned there, then it was so much easier us to have the conversation,
okay, how are we going to make that happen? But Tom, I haven’t heard you speak once about money. So tell me a little bit about that. I mean really, do you guys believe it’s all about the money or is there something more to that?
So money is always a piece of it. And when we talk to people, whether it’s personal or miss component, and that’s not a bad. So
enjoy the things you want to have the experiences that you want to. But that in itself isn’t going to make people happy. And if that’s the goal focused, you’re gonna have other issues. So what we always guide people on is, you know, there’s really kind of four major things. The things that you want the experience as you want the thing don’t want to do. And then the biggest thing a lot of people forget about is the impact that you have, and when I work with entrepreneurs that have an idea or product, and then they try to build a business out of it, they’re usually the ones that struggle. The ones who really have success are the ones that really fall in love with splitting a prob or helping a specific set of customers because that’s bigger than the person or the entrepreneur. So because they’re doing it for a reason, not only do they tend to have more success, but they tend to have a stronger motivator or internal drive, which is, I was a, the gift.
A lot of those challenges that come up. But, uh, the one thing that I’ll also say with that is there’s two modes that people are in. There’s the survival mode, which is a lot of people were in initially. And then ultimately there’s the thrive mode. And most entrepreneurs when they get started, they’re usually in this survival mode. They’re potentially not making enough money, make more money because they want to pay off debt or live a certain lifestyle. And there’s a certain way of thinking and usually that’s very focused at that point, but once you kind of get to a certain point, you realize that you have everything you need. That’s when a lot of entrepreneurs shift to this thrive mode and basically say, alright, how can I do more? How can I have an impact? How can I leave a legacy and help more people beyond just me and my family?
So Tom, solve all my problems in this podcast. Are you ready? So here’s, here’s my, here’s my problem for you. So, you know, just yesterday I said I’ve got to take a break. I’ve got to spend a little bit of time with my family. And then I’ve got to go back to the grind, uh, later that night. And, you know, one of the things that’s so difficult is I said, okay, we got to get out of the house. I got to get somewhere else that I can focus my attention. And so we went and got ice cream. And, you know, the hard thing is, is that coming back, you know, most of all that I could think about was work and what I had to do next. And you know, right now in this stage of business and life, you know, it’s thinking about burn rate, it’s thinking about investors, it’s thinking about employees, it’s, it’s thinking about growth. And what would your suggestion be there, uh, to how to deal with that when you know you’ve got to spend time with your kids, you’ve got to spend time with your wife, but at the same time you’re thinking, but if I don’t do this, if I don’t do this over in the business, I don’t know if we’re going to be able to survive. So how, how do you find that balance? What’s your words of wisdom? And a few seconds.
Absolutely. So the first thing is this comes back to setting those expectations because before you start the business, if you set the expectations that this is going to take a lot more time initially because we’re in that startup phase, then it makes a lot of this easier. Well, the second thing is whenever we’re struggling, the first question to ask is why, why is this? Some is stressing me out and once you figure out why, then you can start solving them, putting systems in place to help you manage that. And um, for a lot of people like what we ended up doing, when they’re overwhelmed or when that’s all they can think about, we haven’t do a brain dump, get everything, had an aunt to the table, and then let’s start prioritizing and figuring out what fits within the time we have allocated for this and then what doesn’t. And for the stuff that doesn’t fit, what has to happen, does it not matter? Can it wait til later? Does it have to be delegated? And then we can start actually solving problems. But until we know that is, it’s, it’s tough to come up with a solution.
But Tom, everything has to be done now. You know, that everything has to be done now or two days ago. Right?
That’s, that’s what we all think. And um, this is what gets a lot of entrepreneurs and actually a lot of people in general is that they end up creating an environment where everything is urgent or they think it’s urgent and then they’re always reacting to things. So a lot of what we like to do is we like to start like there’s a great steven. No, he always talks about the habits of highly six, the seven habits of highly successful people. He talks about, you know, starting with the end in mind. So we do that with our lives. We start with what does the future look like and let’s work backwards to figure out what we have to win to get there. And we do the same thing with business. So when you’re starting a business, looking at, you know, what’s the longterm vision? And then what’s the long, mid and short term goals. We can then take let’s say 90 day goals and work that backwards and ultimately say what are the key actions and the key routines that we have to do to achieve that goal. And then it makes it a lot easier to filter and strip everything else away. What most entrepreneurs do, his stuff comes onto their plate and they don’t have a system or a process to really figure out what they should be doing and what they shouldn’t be doing. And then they ended up getting overwhelmed and they’re always reacting instead of being proactive.
What would you say about the team? How as a CEO, how do you lead your team? Because in startup world like this, it seems like everyone is kind of struggling with that same thing, right? I mean there’s that, there’s that struggle of what do I do next? I should have done this two days ago, you know, we’re behind a week and it, it seems not, that’s not only just for me, but also for my team. So how would you recommend for someone leading a team that’s going through some of that to help their team cope with, with the same things they’re dealing with?
Absolutely. So one of the biggest things that you talked about earlier is really a communication. So what we like, the way I can best describe this to people is it’s Kinda like a gps, so gps has a destination, which is where we’re going. It has a starting point, which is where we’re currently at today, and then with that it can draw a roadmap. Now that’s pretty cool, but as we all know, things change along the way, especially when we’re in a startup so well. A GPS does really well is it constantly checks in and it says, all right, where are we at? We need to be. And then when we get off track, the GPS says, hey
thing. So what we need to do is with our processes model the same thing as the. As the CEO, as the founder, as the leader, you need to be setting that destination and sharing that vision of where we’re going with the entire team. But then you also need to establish this cadence of communication to stay on track with them and this arts ugly. Every day you’re going to puddle or a stand up with your team. This is going to allow you and the team to get together and kind of figure out what’s going on, what needs to be done, what’s getting way, and then everyone can be off doing their thing. This then ties into like a weekly session where we do a review like what went well once we challenged,
so give me more successful next week and then let’s kind of plan that out. This then leads into kind of a monthly session where we say, all right, we’re now a third of the way through the quarter. How are we, what’s our goals? Do we need to make any major shifts? And then every 90 days we can say, all right, now we’re a quarter of the way through the year. What are we doing towards our overall goals and have to make any bigger shifts. So by putting a process like this in place, it really allows you to get clear on where you’re going and make sure the entire team is clear, but then also a long way you can adjust and move forward based on that.
Definitely. So one. One question I have for you is how have you done this and your life? If you can just give us an example of of what that looks like maybe in just your daily life?
Yeah, absolutely. So all those meetings that I just described to you, my wife and I do, you know, with our life and our business, we have a daily meeting, a daily huddle. We call a sync up and drink up. We sync up on kind of what’s going on for that day, what we have completed yesterday and then what’s in the way and then we drink our caffeine. So that’s kind of our daily meeting. Once a week we do a review and for us, because we’re running multiple businesses and usually we do these meetings just with us. We hit on personal stuff and all of our business stuff. So for us this really works well to combine those together to make sure that we’re not lovingly business takeover the life. And then actually next week we’ve got two days set aside for our annual planning to be able to reflect on everything, personal life and businesses, and then really set our next year’s goals and start to break down the next 90 days.
Well, you guys seem like a fantastic team and would love to hear from her and hear her side as well sometime. So really the last question we have for you is we need five key takeaways from you. What would you recommend to our listeners when they’re considering about starting a business or running a business that’s already been in startup mode? What would you recommend to them? And just life in general?
Five key takeaways. All right. So first one is success starts with you. And uh, if you’ve ever been on an airplane, the advice that they give you, like at the beginning is, you know, in the event of, you know, uh, an accident, put your mask on first before helping other people. That comes down intrepreneurs as well. You got to take care of yourself mentally, physically, and you’ve got to really be in a good spot before you can help your family, before you can help your team grow. So first success starts with you. Second, clarity is one of the biggest productivity hacks that is out there, but most people miss it. So if you get clear on what you want out of your life, if you get clear on where you want your business to go, then you can start figuring out what the key things are that will get you there and that’s gonna.
Make everything so much easier. Three part of making sure that you can integrate your life in business is to make sure that you’re selecting of business that actually is going to support your life goals. So a lot of times what we’ll find when people are disconnected is they’ve picked a business that ultimately isn’t going to get them to what they want their life to look like. And then that causes a lot of issues. So once we can get those things in alignment now instead of having a life and business fight each other, they actually integrate and support each other for I would say, don’t fall in love with your product or service, but instead fall in love with your customer because as we talked about before, if you’re constantly thinking about how can I serve this customer and how can I make their life better, that’s going to lead to a successful business. And that’s not even just in business, that’s also in life. So if you’re thinking about how can I serve all the relationships I have, how can I serve my spouse? How can I serve my kids? You’re ultimately going to have more fulfillment and more success. And then finally, I would say, especially as an entrepreneur, you want to be creating an environment that’s going to allow you to succeed. So we typically have more stress, more challenges than the normal person. So you really want to make sure that whatever environment you create is going to
allow you to have the momentum to go forward and the support you need when things get tough. Fantastic. And I sure hope that this has been encouraging to our listeners as much as it has been to me and I know our team once they listened to this as well. So tell us, Tom, what’s the best way if we want to learn more about you and Arieanna and how do we get involved with you and your support and you know, I call them counseling sessions because I feel like that’s what I’ve been doing. I just now is as having a counseling session of all my problems here. Where do we find you and how do we, how do we find more about you? Absolutely. Um, so we’re all over the place, but the easiest way to find us as they go to our there you can find the podcast blog post.
We put a lot of information up all around the topics that we talked about here. And what I’ll actually do, I’ll make a special page for this episode. So if people want to go to [inaudible] dot com slash h F, we’ll put some specific links that talk about some of the topics that we talked about here. All right, that is fantastic. Well, we sure appreciate your time and your effort to put this together for us and those five key takeaways and definitely look forward to talking to you further. Again, just want to remind all of our listeners that if you ever looking for insurance quotes, bright is the place to go where insurance quotes don’t sting. We hope you guys have a wonderful day and we will see you next time. Thanks.

Find Tom at:

Listen to Tom & Ariana’s podcast:

Check out Tom & Ariana’s blog:

Visit BriteBee online or follow our Blog, Facebook, LinkedIn, Twitter, Instagram or YouTube!