Tom and Ariana are college sweethearts and now Business partners. This husband & wife team are owners of 3 very different businesses. While running their real estate business, wine & liquor store, and online coaching & training for entrepreneurs, they’ve also raised two energetic youngsters.
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Time Stamped Show Notes
(click the time stamp to jump directly to that point in the episode.)
- [00:52] – Tom runs a variety of businesses with his wife
- [00:58] – His wife was the very first girl he met in college
- [01:11] – As they got to the end of their college career, they both looked for jobs
- 01:23 – A friend gave Tom the book, The Automatic Millionaire, which became his key to entrepreneurship
- [01:33] – Tom found out he could be a millionaire himself
- [03:24] – His area of expertise is in integrating life and business
- [04:46] – Share something we don’t know about your area of expertise that as Entrepreneurs, we probably should: Get into the cycle of reflecting on what’s happened, planning for what you want to do next, and executing
- [06:30] – “How you spend your days is how you spend your life”
- [07:07] – Worst Entrepreneurial Moment: Tom set his goal to retire by the age of 35. After finishing school, he thought about how he could start taking action on his goal. He didn’t have much money for investing in the stock market and he didn’t have much experience in real estate either. He heard an ad on the radio about a free 2-hour training session. They would give you a 3-day training session for $500 and then up-sell you to $15,000, which Tom ended up doing. He took part in all of these sessions without telling his wife.
- [09:34] – His choice was between taking more training sessions or starting to use what he already knew – he went with the latter and bought his first duplex within a couple of months
- [09:57] – His choice helped them make enough money to pay back the cash he used for training
- [10:50] – When you invest in yourself, you won’t always get a lot of value at once. However, you may get insights that could open up the doors to creating something successful along the way
- [11:39] – No training or course alone is going to make you successful – it will become a part of your journey, but at the end of the day, it comes down to your mindset
- [13:28] – Entrepreneurial AH-HA Moment: When we don’t take action and risks, we won’t get to those ah-ha moments. Tom took a couple of years after his real estate leap before he finally opened his liquor store. He realized that he kept telling his wife WHAT he wanted to do, but he didn’t tell her the WHY. One day, he was able to tell her the reason he took all these risks: to build their life together. They talked about the life they wanted and started to work backwards
- [15:35] – Everything became clearer between them once they had this discussion
- [16:01] – Being an entrepreneur is a journey, BUT make sure it is YOUR journey
- [17:37] – What is the one thing you are most FIRED up about today? “My wife and I recently shifted and launched a new brand around family entrepreneurs”
- 18:54 – Find out more about FamilyEntrepreneurLife.com
- [21:38] – The Lightning Round
- What was holding you back from becoming an entrepreneur? – “It was really me not being able to articulate my why to her”
- What’s the best piece of advice you’ve ever received? – “Don’t get fouled”
- What’s a personal habit that contributes to your success? – “It goes back to planning. And it’s really that weekly sync that my wife and I do where we reflect on what happened, plan out what’s going to happen next, and we go ahead and do it”
- Share an internet resource, like Evernote, with Fire Nation – LeanKit
- If you could recommend one book to our listeners, what would it be and why? – For Better or For Work – “after reading that it helped me understand more about what Ariana was going through”
- [23:00] – There are a lot of failures along the entrepreneurial path, so surround yourself with successful people
- 23:28 – Connect with Tom on TomAndAriana.com/Fire and get a FREE download!
Tom Sylvester: Absolutely, John.
John: Yes, from computer programmer to serial entrepreneur, Tom owns and runs a real estate business, a wine and liquor store, and an online coaching and training company for entrepreneurs. Tom, take a minute, fill in some of those gaps from that intro and give us a little glimpse of your personal life.
Tom Sylvester: So, as you said, I run a variety of different businesses along with my wife. We have two young kids and we actually met – she was actually the very first girl that I met in college, and so from there we had a handful of really good years in college. As you said, I was a computer programmer and it was interesting that as we got towards the end of our college career we started thinking about kind of the next steps of what happens beyond college, and both of us were looking for our jobs and I wasn’t a big reader at that time, but I had a friend that gave me a book called The Automatic Millionaire.
I know you don’t read a lot, but just read this before you graduate. So, I did and what was interesting there was, you know, I came up, I really didn’t have a lot of money, my family worked hard, and what I found out was that I actually could be a millionaire and it actually wasn’t that hard. You just had to work 45 years and put money away consistently and use the power of compound interest. So, I was like that’s awesome, but I really don’t want to wait 45 years for that to happen. So, just on a whim I said, you know what, 15 years sounds good. So, if I can “retire” by 35, that would be good, and so that kind of started us on this path of really entrepreneurship, and a funny story, a couple of years ago, right after you launched your podcast, I started listening to it, and I said, you know, I want to be on that show some day –
John: Ooh –
Tom Sylvester: – but I don’t know if I’ll get to share the story. So, I’m so excited to be here today because a couple of more years under my belt and now I’m very excited to be able to share a lot of what I’ve learned on that journey.
John: Well, Tom, I am fired up that you are here as well, brother, and there’s actually a quote that I just posted a couple days ago on Instagram that I think is kind of relevant to what you just shared, and that is “Success is simple once you accept how hard it is.” Now, that’s good and bad, Fire Nation, to kind of absorb because that old school mindset of work hard, save five to ten percent every year, compound interest, and in 45 years you’ll be a millionaire, like that’s all well and good and that does work and that is tried and true, but we do live in a different world nowadays.
We live in a world where we can impact not just people within our town or region, but around the world, and not everybody around the world, but it can just be a special niche that you’re impacting in a really meaningful way that’s going to allow you to add enough value to the world so you can get to where you want to be financially and be financially successful and be location independent if that’s something that interests you, and there’s a lot of ways to go about that, but Tom, what I’m curious right now for you is what would you consider today your area of expertise?
Tom Sylvester: Yeah, it’s an interesting question because as we run a variety of businesses, we picked up a lot along the years, but the biggest thing that I think we figured out is really how to integrate your life and your business, and we use the term integrate very explicitly because for a long time people have talked about work life balance, and part of what that conjures up in your mind is really like a scale and you got work on one side, life on the other side, and if you put more into work, you’re going to take away from your life.
And what we figured out is even with running multiple businesses, we’ve actually been able to integrate the two of those so that we’re not taking away from our life, but we’re actually setting those up so that they’re supporting each other and allowing us to live the life we want even though we have a lot going on with our businesses.
John: What I like about your answer is that because you’ve been successful in multiple businesses, not just like one super specialized unique niche, but multiple businesses that frankly are completely different like running real estate, a wine and liquor store, online coaching and training. These are different areas. So, you’ve obviously developed traits that have allowed you to be really successful and it’s good that you can identify those things. So, maybe kind of just pull out one really specific tip, tool, or tactic that you can share with Fire Nation about ways that you’ve learned how to integrate your life and your business that we as entrepreneurs should probably know.
Tom Sylvester: You know, my background was in computer science and I started working on projects, and a lot of those projects were really big, and a lot of them tended to fail, and so what I started looking at was, well, what are some different ways to be able to actually run projects and really achieve what we want to, and what I kind of figured out was this lean, agile, scrum kind of methodology that was out there, and so what we started doing was actually integrating a lot of those concepts together as we ran our businesses and our lives.
So, the biggest tip I can give people is get into this cycle of reflecting on what’s happened, planning for what you want to do next, and then executing. So, a lot of people do goal planning on an annual basis, so, one time a year they plan their goals. They set a plan out and then when things go awry two weeks in, they give up on it. So, we’re big fans of doing that planning on different levels. So, yeah, you’re going to do your annual goal planning where you’re going to look out, but then you also want to do a 90 day goal planning, weekly goal planning, and then really daily, and what that allows you to do is each time you get together, you reflect back on what just happened.
Based on that you plan out what you’re going to do next, and then you actually go and do it, and so what this allows you to do is just continuously plan and react to what happened and make sure you’re still on the direction of where you want to go to achieve your goals.
John: What’s worked really well for me, Fire Nation, in this area is to meditate every morning. I spend seven minutes meditating. I’m trying to get that number up a little bit higher, to be honest, but I’m still there. I’m at seven minutes meditating every morning, and then directly after that, I journal, and that journaling allows me to do exactly what you just shared Tom, which is No. 1, kind of reflect on what’s been happening to make sure that I’m glad what I’ve been doing with my time, how I’ve been spending my days because as we know, Fire Nation, how you spend your days is how you spend your lives, but also to say, okay, what am I doing today, what’s my goal today, and what are my shorter terms goals, like week and month goals, and then what are those hundred day goals and then what are those potentially year goals, and to really kind of keep reflecting on that to keep your finger on the pulse.
Now, Tom, you haven’t always just hit home runs every time you swung the bat. I mean, you’re rocking right now with real estate, with your wine and liquor store, with online training and coaching, etcetera, but you’ve had some struggles as well, and that’s kind of what I want you to talk about right now is your individual worst entrepreneurial moment. Take us there, tell us that story.
Tom Sylvester: This is a tough. So, I talked about how excited I was getting out of college and I set that goal to retire by 35, and so I’m the type of guy that, you know, I’m quick start, I hit the ground running. So, right after we get out of school, start looking for, okay, well, how am I going to achieve that goal, and I said, well, the stock market, that’s how I learned in the automatic millionaire book. So, I started looking into that and I realized I’m not that smart, I don’t have that much money and Ariana wasn’t a big fan of that. So, I said, okay, I got to try to try something else. So, then I was like real estate. A lot of people make money in real estate, let me go and try to do that, and so I presented that idea to Ariana and she wasn’t a fan either.
She’s like well, I don’t want to be a landlord and she just kept shooting down every idea that I came up with, and I really got to a dark spot where it was like, okay, how am I ever going to achieve this goal if every time I try to do something, my wife tells me no, and so on a whim, I’m driving back home from work one day and I hear this ad on the radio, and it says free two day real estate training, change your life, and I’m like yes, this is it. So, if anyone’s ever been to one of these trainings, this is kind of how it works. You go to a two hour training that’s free, and then they sell you typically a three day training which is like $500.00, and then they do a really big upsell.
The one we ended up doing was $15,000.00, and so I had no intention of doing that, but they really kind of hit on everything that I was trying to do and they hit me in a vulnerable moment. So, I ended up spending $7500.00, half of that on two credit cards because I didn’t even have one credit card that had that much money, and I did all of this without talking to my wife, and at that point she wasn’t even my wife because we were set to get married the next year. So, we had just graduated college, saving up for a wedding. We just bought a house and then I had to come home and tell her that I just spent $7500.00 that we didn’t have on a high interest credit card for this real estate training that she was already against, and you can imagine how that worked out. She was not very happy, and we had to have a lot of conversations about why I did that, what was driving me, and then what that meant for really us being together and building our lives together if I was just going to go out and do something rash like that.
John: So, I’m kind of curious how this story plays out. So, I mean, you invest all this money. How does the training actually play out? Did you feel like you got a good return on that investment, just with the specific training itself?
Tom Sylvester: So, we ended up buying four trainings. I went to the first one and I really wasn’t getting a lot out of it, and at that point I thought, you know, I really got two paths here. I can spend a bunch of money to travel to other cities and go to the other trainings or I can just take what I know and take what’s available online and from reading and just go out and start buying and investing in real estate. So, quit learning about it and do it, and so that’s what I did. So, I ended up buying my first duplex a couple months later, and then we just continued from there, continued buying properties and repeating the process, and so what that allowed was we actually made money off of the real estate investing to pay back the training, which was great.
John: Now, did you get some valuable tips from that training that you were able to use, anything?
Tom Sylvester: Yeah, absolutely. There was a game they had because – it was called cash flow, and it was basically a game that kind of took you through how to – it was kind of like Monopoly, but on steroids.
Tom Sylvester: And what it allowed me to do is realize that, hey, if I lower my expenses and if I keep investing in assets, you know, really rich dad, poor dad type philosophy, I can make this work. So, what it really did, it wasn’t so much the real estate knowledge, but the opening up of the mindset and realizing that there’s a lot of opportunity out there if you just go out and put in the work and make it happen.
John: See, this is interesting, Fire Nation. I’m definitely not advocating dropping a lot of money on high interest credit cards at all, like I think you really need to be smart with the investments that you’re making, but what a lot of people don’t realize is that when you invest in yourself and when you invest in high cost premium training, you might not get a ton of value bombs dropped up on your head, but you might get one or two or three little insights that literally could just kind of be that wedge that cracks open this whole piece of the puzzle you never would have seen before that now you can put back together and create something successful.
So, don’t go into something thinking that you need to get this incredible revelation. Maybe realize that, hey, sometimes just that one little tweak, that mindset tweak in Tom’s case here, that opened up his mind, his eyes, and that’s kind of my big takeaway from your story, Tom, but what do you want to make sure our listeners get from your worst moment?
Tom Sylvester: Yeah, I would agree, it’s really that. There’s a lot of learning out there, and there’s a lot of people that get caught up in just buying course after course, and no course is going to allow you to be successful. They’re going to be parts of that. What it really comes down to, your mindset and if you have the right drive. You’re going to make some mistakes and some of them are going to be bigger than others, but if you just keep moving forward towards that goal and learning from the mistakes you made, you’ll eventually get there, but it might take some time.
John: I mean, I remember that I was just in this like super research mode when I was about to launch my podcast, like I would just watch interviews by Larry King and fill in the blank, and finally my mentor, Jamie, just said, tomorrow, 3 p.m., you and I are jumping on Skype and you’re interviewing me, and I was like, what, like what? I would have spent the next couple of months just watching people interview other people, and maybe picking up a little bit of this, a little bit of that, but once I just actually interviewed Jamie and I saw how bad I was and I saw how hard it was to actually do that, that was just like such a light bulb and I was like, oh my God, there’s only one way that I’m actually going to become a better interviewer and that’s to actually interview people.
And to me that was just, again, a little mindset shift that I recognized and said, screw all of this researching. I’m still going to do this, but I’m going to do it congruently with actually doing the thing, which is interviewing, and that’s what you did Tom. You said, hey, I can travel the country and spend more money and learn, learn, train, train, train, but I could actually do the thing and keep learning as I go as well, and so I’m actually learning by training, by seeing what’s on YouTube and other learnings that are available, but I’m also actually doing the thing that I need to become that expert in. So, Fire Nation, a lot of great takeaways there, but Tom, I do want to shift a little bit because we just talked about a lot of ah-hah moments, those little mini ah-hah moments you had along the way.
What’s one of the biggest ah-hah moments that you’ve had to date? What’s one of those great ideas that you’ve had that you’ve actually put into action? Tell us that story, take us on that journey.
Tom Sylvester: Yeah, so it really came out of really that big failure, and I think that’s the way it happens most often is when we’re not taking those great actions or great risks, we’re not gonna really get to those light bulb or ah-hah moments. So, I talked about some of the challenges and the conversations that we had after I did that, and it wasn’t until a couple of years later, until I actually opened a second business, which was the wine and liquor store, that it really came, and what I realized was that I kept telling Ariana what I wanted to do, but I didn’t tell her why I wanted to do it.
And every time she was resisting, she was resisting the actual idea, but she didn’t understand why it was important to me, and we were having one of our conversations where we’re trying to figure things out, and I remember she was crying, and I really just was completely honest, and I said, you know, the reason I’m doing all this is because we have this life that we want to build together and these are going to be the ways that get us there, and it was that moment that she’s like, okay, I get it.
John: Let me stop you there for a second, Tom. I’m just curious. Did she ever come back to you, and share what she thought your why was and why it was upsetting her?
Tom Sylvester: You know, she really didn’t think about the why. She was just thinking about all of the actual things I was trying to do, and she was thinking of all the bad things that could happen there, and it wasn’t until we shifted that she then realized that it was something bigger than just becoming a landlord, for example.
John: Got it. So, keep on going.
Tom Sylvester: So, from there we really started talking about, okay, well if the why is to build this life, how about we get aligned on what that life actually looks like, and it sounds easy, but most of us just kind of go through our day to day and we don’t think about that bigger picture. So, we spent some time getting aligned around that life we wanted, and then we started working backwards. We said, okay, well, that’s a lot to get to, but how can we start breaking that down into smaller chunks, smaller goals, to actually get there, and once we then got back there, it’s like, okay, well, here’s the path that we’re planning to take getting there.
Now what roles are we each going to play in that, and this was very important for us because we were married at that point, we had our first child, we had multiple businesses. So, we had all these different roles and all these things we had to get done, and it wasn’t until we really started having these conversations and getting completely clear on what we wanted, that then everything else started to fall in place, and you just got into the flow of being able to plan those things out. We’re each kind of taking our roles, we’re figuring out what’s working and what’s not, and then we’re continuing forward with that.
John: So, Tom, I kind of want to do the summation thing right here where you kind of share with us what is the biggest takeaway that you want to make sure our listeners get from that kind of mental breakthrough that you had.
Tom Sylvester: Being an entrepreneur and just going through life, it’s a journey, but I would say make sure that it’s your journey. So, we see all these influencers, we see a lot of people who have lives that we think we want, and I would say, stop following what everyone else is doing, and really remember why you want to do it, and focus everything you do on getting to that why.
John: I do love this, and Fire Nation, this is a huge takeaway for any of us that are in relationships, who have significant others, whether they be partners in business, partners in life, combinations, whatever it might be, is explaining the why to your loved one. Make sure that communication is there, and that’s going to help you as well, just like verbalizing it and getting it out there in the open. Again, that’s why I’m so big on journaling because I know that I’m in a way verbalizing to my journal exactly what my why is on a day to day basis, and there’s something that I was thinking about Tom, which is a little bit of a quote it might turn into on Instagram later.
We spend so much time deciding on what we want for things like dinner, but like how much time do we actually spend deciding what we want for our lives, and that’s kind of crazy to think, but we spend so much time on these little things, that of course are important because these little decisions make up our day to day and make up our lives, but how much time do we actually step back and say, okay, I’m really making this big decision on this cobb salad I’m going to make today for dinner, but let’s make this big decision about where I want my life to be a year from now. Now, Tom, you have a lot of businesses, you have a lot of things going on, a lot of things pulling you in different directions, two kids, multiple businesses. What’s the one thing, business wise, that has you most fired up today?
Tom Sylvester: Yeah, it’s actually a great lead in from that last quote. So, we’ve read the Four Hour Work week and there’s a whole bunch of books out there and there’s a lot of really good people doing really good things, but one of the things we continue running into was, as parents, as family entrepreneurs we were struggling because what we realized after the fact was a lot of people that were out doing great things maybe had a different path they were on. So, maybe they were single, maybe they didn’t have kids, so they had a little bit more freedom and flexibility around maybe following Tim Ferriss and going to another country that’s lower cost of living.
There were certain things that we couldn’t do as a result of being parents and being in a family, and so as we’ve been at conferences and had our podcast and were talking to people, we’ve had a lot of people really say the same thing, like you guys are very similar to us, we have a family, and you guys are where we want to be, so how do you do it? So, we took – after you hear that so many times, it’s like okay, well, there’s an opportunity here. So, my wife and I recently shifted and kind of launched a new brand around family entrepreneurs and helping entrepreneurs that are really focused on getting that life they want with their family and helping them navigate through there and build those businesses that support the life that they want.
John: And where can Fire Nation find out more?
Tom Sylvester: Yeah, they can find out more at FamilyEntrepreneurLife.com
John: FamilyEntrepreneurLife.com. Fire Nation, we’ve been dropping value bombs. We got more coming up in the lightning round when we get back from thanking our sponsors.
Tom, are you ready to rock the lightening round?
Tom Sylvester: Absolutely.
John: What was holding you back from becoming an entrepreneur?
Tom Sylvester: So, I used to say it was Ariana, but it was really me not being able to articulate my why to her.
John: What's the best advice you've ever received?
Tom Sylvester: So, this is a weird one. It was actually from a basketball coach, and he said, don’t get fouled and I didn’t understand what that meant for a long time, but basically what he was telling me was don’t put yourself in a place where other people can dictate what happens to you. Put yourself in a place where you decide that.
John: What's a personal habit that contributes to your success?
Tom Sylvester: So, it goes back to planning, and it’s really that weekly sync that my wife and I do where we reflect on what happened, plan on what’s going to happen next, and then we go ahead and do it.
John: Recommend one internet resource?
Tom Sylvester: So, we’re big fans of a tool called LeanKit. It’s basically a to do list that’s very visual, so you can put all your items on there and it helps you track where they are all at.
John: Recommend one book and share why?
Tom Sylvester: So, there’s a book called For Better or for Work, and it’s really about – the author is the non-entrepreneur in the relationship, and after reading that, it helped me understand a lot more about what Ariana was going through, and it helped me connect more when I was talking about what I wanted to do business wise.
John: Love it, and Tom, I want to end today on Fire with you giving us a parting piece of guidance, the best way that we can connect with you, and then we'll say goodbye.
Tom Sylvester: Absolutely, so there’s going to be a lot of failures on this path, and one of the best ways to be able to get past a failure is to surround yourself with great people. I’ve seen times where I’ve been down, and having a mentor, having other people that are like, look, this is just a blip on your journey, don’t let this blip stop you. So, making sure that you’re surrounding yourself with those entrepreneurs and those other successful people is critical, and if people are interested in a little bit more of how we’ve been able to integrate our life and business, they can find us at TomandAriana.com/fire, and we’ll actually have a free download with some of our favorite tips.
John: Love it all, and Fire Nation, you are the average of the five people you spend the most time with. You've been hanging out with TS and JLD today, so keep up the heat, and head over to eofire.com. Just type Tom in the search bar, his show notes page will pop up with everything that we've been talking about today, and these are the best show notes in the biz. Timestamps, links galore, and, of course, head directly to TomandAriana.com/fire for that great gift and FamilyEntrepreneurLife.com to learn more about that. Tom, thank you for sharing your journey with Fire Nation today. For that, we salute you, and we'll catch you on the flip side.
Tom Sylvester: Alright, thanks, John.
John: Hey, Fire Nation, hope you enjoyed our chat with Tom today, and from accomplishing goals to launching podcasts to creating funnels and webinars that actually convert, I have four free courses awaiting for you at eofire.com. I will catch you there or I’ll catch you on the flip side.
1) Free Podcast Course: Learn from JLD how to create and launch your podcast!
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