Episode Overview

On today’s episode of the Serial Startups Podcast, we introduce ourselves to you guys.  We are serial entrepreneurs (meaning that we have started and run multiple businesses).  We are also married, have two kids and constantly work to make it all work.

Episode Key Points

  • We introduce ourselves and share who we are
  • A brief overview of our multiple businesses
  • Our big goal that Tom set when we graduated from college
  • We talk about our failure of investing in the stock market
  • How Tom spent $7,500 on a credit card for real estate “training”
  • How we started our first business and continued with many more
  • Why we believe multiple streams of income is the way to go
  • Why we started this podcast and what to expect from future episodes

Episode Transcript


Prefer to read the transcript instead? Click the plus icon --->


Tom: This is the Serial Startups Podcast, Show 1. In this episode, we’re going to introduce ourselves, give you guys our background, and explain what this podcast is all about.

Ariana: Welcome everyone. I’m Ariana Sylvester and I’m here with the hubby Tom. We are here to introduce ourselves in our very first podcast.

Tom: Thank you guys for being here and listening. This has been something that we have been wanting to do for a long time, and by “we” I mean I have been wanting to do this for a long time.

Ariana: And he finally convinced me.

Tom: And it has taken about a year to get Ariana on board. This is our first podcast, so we are going to give you guys a quick background on us and we are obviously going to go a lot deeper as we get into the show more. But once again thank you guys for being here and we are so excited to be having this podcast going.

Ariana: Yes, so first off, to define ourselves. We are serial entrepreneurs. We are a husband and wife and most importantly we are parents.

Tom: And when we said serial entrepreneurs, that means that Tom is the serial entrepreneur that wants to just start a million businesses, and Ariana has given herself the title of…


Ariana: Reality checker.

Tom: Reality checker. So I think every couple that wants to start a business probably has one person that falls into each of those roles and we definitely do.

Ariana: Yes.

Tom: Alright, so what do we do? We own multiple businesses. They’ve taken several years to build them up and a lot of this podcast is going to be talking about how do we recommend people go about starting their first business and get to the point where we are where we actually have multiple income streams.

So our businesses are around a bunch of different industries. Our first one is in real estate investing. We’ve been doing that for quite a while.

Ariana: That started everything off in 2007-2008, right after we got married.

Tom: We’ll get into a funny story later on about that. From there we progressed into opening a wine and liquor store.


Ariana: Yeah, actually it was kind of a weird connection because our real estate business bought the building and we put a wine and liquor store in the building. So that is our second business. Our baby. Still growing.

Tom: And a funny fact about that… Ariana is probably the most knowledgeable person about wine, who doesn’t actually drink wine.

Ariana: Yes, I don’t actually like wine. I have like 2 wines that I will drink, but that is about it. But I can tell you a lot about all different types of wines and where they came from.

Tom: Absolutely.

Ariana: And then we started a third business that we didn’t really know what it was going to be when we started it, but Tom really wanted to get into blogging. He wanted me to get into blogging, so we started Entreprenewlyweds. It was the beginning of our online business and we’ve had various other websites with that.


Tom: Yeah, and a lot of that actually came from the first two businesses. So as we got those businesses going, people would come to us all the time and ask “how have your started your business” and “how do you operate that together”, especially once we started having kids. That is where Entreprenewlyweds came from. It was just our way to start sharing that information with people.

Ariana: Yeah, a lot of people have liked our interesting blogs. We have had some interesting viewpoints.

Tom: Yeah, and as that grew (we’ve had it for almost two years), what we really noticed was that we were answering a lot of the same questions and as more and more people found out what we were doing, we realized that we could no longer help everyone one-on-one with business questions and relationship questions. This is where this podcast came from. As people started asking we questions, we realized that: first off, Ariana hates blogging. So everytime that we would try to get a blog out, I would have to push her to do it, and half the time I would have to ghost-write it for her.

Ariana: It was my homework.


Tom: So as we started talking, we were like “how can we start sharing this information and really helping people out in a way that we like?” So I listen to podcasts all the time. Ariana barely ever listens to podcasts.

Ariana: I don’t have much time to listen to podcasts.

Tom: But we figured this is a good medium where we can answer questions and help people out. Plus it is much easier than trying to push Ariana to blog.

Ariana: Yeah, way more fun.

Tom: So with that, Ariana, do you want to give the background on how we met and how this whole crazy thing got started?

Ariana: Sure. So funny story, I got accepted to Michigan State out of high school. I was supposed to go there, I was all set until my parents and I realized how much money that was all going to cost and how far away it was. My parents were also very involved in my high school career and they realized that they would not be able to come and visit as much as they would like. So I decided to go to Oswego. SUNY Oswego, it has Zoology, which was my major. It was also a little bit cheaper. So I went to Oswego and who knew that I was going to meet the love of my life who lived three doors down from me.


Tom: Absolutely. So I applied to one school, Oswego. I got accepted and said “great, that is where I am going”. And so before I went to college, my cousin gave me a tip. He said, “I’m going to tell you one thing… stay single”. So when I got to school Ariana was actually the very first girl that I saw, and I snatched her up right away.

Ariana: Yep, one week in and we were dating. We played soccer and it was pre-season, so it was only people from the soccer team and some of the other teams, so the dorms were pretty empty. Tom lived right down the hall, so I was wandering and looking for people to talk to and came to their room door. So in the couple days that followed, Tom seemed to be drinking a lot of water. Come to find out, it was because the water fountain was right past my door.


Tom: So actually I think it was because we were playing soccer, and we had a lot of practices and I had to said hydrated.

Ariana: Uh huh, yeah sure it was. So we started dating a week in and the soccer teams used to call us “the married couple” because we hit it off right away. It was like we were met to be and they thought it was hilarious that we went everywhere with each other and did every together. We also had the hatching of our five year plan. We were going to get married after college, which we did. We got an apartment together, and them Tom really didn’t like paying rent, so we decided that we were going to look for a house.

Tom: Yeah, and to take a step back, we got together in college and had a great time. We played soccer and had a lot of very fun times, but as we approached the end of our senior year, one thing that hit me was that we were both finishing school. Ariana actually went to school for a zoology degree. We will get more into that later, but probably not the best choice living in NY.


Ariana: Had a minor freak-out my senior year, “what am I gonna do?”

Tom: Yeah, and we both kind of had that. I had a friend give me a book called “The Automatic Millionaire”. I wasn’t a big reader at the time. I’m a huge reader now, but in reading that book, there was a basic concept that stuck was me. Most people follow the traditional route, which is you go to school, you get a job and you work for forty to forty-five years. Hopefully at the end of that time you can retire, and if you are not dead then you can enjoy your life. So that wasn’t what I wanted us to do when we got out of college, and this book basically said that if you put some money away starting young, and you do that consistently and follow a couple other habits, by the time you are sixty-five you can be a millionaire or multi-millionaire. That sounded awesome, but the one problem that I had was that I didn’t want to wait until sixty-five. I didn’t want us to miss out on all of the life experiences by having to wait that long.

Ariana: Yes, so he set the goal to be retired by thirty-five.


Tom: Fifteen years. Yep, so I set this goal before we left college and said “by thirty-five, I want us both to be retired”. And let me clarify what that means. That means, we have options. Most people in their lives are not happy because they don’t have options. They work a job and they don’t like a job, but they can’t do anything else. So what retirement meant for me when I set that goal was allowing Ariana and I to live the lives that we want to without having to have someone else tell us what that means. So we are not actually going to be retired like we are not working, but what that means is that we have the income coming in and we can decide when we want to work, how we want to work and what we want to do in the meantime when we are not working.


Tom: Alright, so jumping back to what Ariana said, when we were moving out of our apartment, prior to that, I was like, “how am I going to make this goal of retiring by 35 work?”  So first off, we had a little bit of money and I said, “well, stocks sound good”.  Everyone seems to be investing in stocks and you hear these stories of people making millions of dollars day trading, so I started to read a ton of books about that.  After reading, I learned very quickly that either I’m not smart enough, or… no that’s probably it, I’m not smart enough to actually make money in the stock market.  In addition, to make money in the stock market and many other investments, you need a lot of money.

Ariana: Yeah, we did not have that.  We were broke college kids.

Tom: Exactly.  Just out of college.

So let’s say you buy a stock and did all of the research right, you put $1,000 into that stock and it goes up 100%.  If you only have $1,o00 in that stock, then you only make $1,000.  Now if someone has $10,000,000 and they put it into the same stock, they have made $10,000,000.  So we realized that young and broke, that strategy is not going to work for us.  So I got a little frustrated.


Ariana: He tried to get us into real estate and wanted us to buy our first house. He wanted us to buy a duplex and live on one side and rent out the other side. And I was not a fan of that idea.

Tom: Alright, so let’s talk about why that made sense and then what we actually did. So that makes sense because the whole point of being able to have options is to reduce your expenses and increase your income. And you want to have money left at the end of the month of every month. So, if you’re renting or if you’re buying a house, that means you’re increasing your expenses every month. But if you’re renting, if you’re renting a duplex that you own, and someone lives on the other side, what that means is that their rent is going to cover most, if not all of your expenses so now you’ve essentially cut out a mortgage payment or rent and then you can take that money and invest it into another business.

Ariana: So the problem with that is that Tom didn’t really explain that to me when he first put that idea out about buying a duplex. We didn’t have very good communication about.


Ariana: We were just out of college. We were supposed to be getting married. For me, it was really tough to think about doing something crazy like becoming a landlord. I wasn’t ready for it.

Tom: It probably was a little scary right?

Ariana: It was a little scary. It was a little scary and I know it’s a little scary for a lot of people to think about that sort of thing. So yeah that was a road block that we hit and…

Tom: So at the end of the day, did we buy the duplex?

Ariana: No, we did not.

Tom: We did not buy the duplex.

Ariana: We bought a one floor ranch.

Tom: Yep – which, it has turned out great. But once again, I felt like a failure at that point. So I couldn’t figure out the stock market. I thought I had everything with real estate.

Ariana: The greatest idea ever.

Tom: Yep. And then that didn’t work and I really just felt defeated and I’m like, alright, if we can’t do those two things, how are we actually going to get to this goal? And it actually hit me driving home from work one day. I was down and out and I heard this ad on the radio that said, live your dreams. Invest in real estate. Make all this money. Free two-day training.


Tom: And I’m like, that’s it. I just need some training for real estate and then I’ll be able to convince Ariana and we’ll do all of this stuff. So I came back, told her we’re going to this training, actually invited my cousin along with me, and we went to the two hour session. And from the two hour session, they sell you’re the dreams. And from that, they actually gave you a three-day training that you can do for only $500. And I’m like yeah, $500. We don’t have a lot of money but that’s a good investment. And then it was even better because you could invite somebody else for free so I invited my cousin so it only was $250. So hopefully what you’re starting to see already is that, these training sessions, they’re very good at sales and they’re very good at convincing people like me to go and spend money with them, because they always give you just enough to get you interested but not enough to actually run with it. So we have a couple blogs that we’ll link to and if you guys want the show notes for this show, it’s SerialStartups.co/show1.


Tom: So we went to the three day training and at the end of the third day, it was their upsell to their next course. So at that point my cousin and I were like yeah, we’re not going to spend money even though we don’t have what we need now, we’ll leave. And it just kept coming back to me. If I don’t make this happen, how are we going to get to that goal? And they listed the prices of the courses and they were like $10000, $15000, $30000 and somehow my cousin and I convinced ourselves that we buy this $15000 training pack of four additional trainings. The problem was, we didn’t have $15000. And what we ended up doing was putting it on a credit card.

Ariana: On multiple credit cards.

Tom: Yeah, multiple credit cards because we actually didn’t even have a credit card that would allow that much money on it. And by the way, I didn’t tell Ariana any of this after I had already done it.


Ariana: Yeah, big no-no.

Tom: Yeah, so that was an interesting conversation afterwards. I was so excited and then I was like, oh crap. We just spent a whole bunch of money on my credit card that we don’t have, Ariana was referencing our five-year plan from the previous year. I had just proposed to you I believe.

Ariana: Yeah, we were supposed to be getting married.

Tom: Yep. And that just added more onto our debt.

Ariana: Not to mention, we had just bought a house.

Tom: Not to mention, we had just bought a house.

Ariana: So yeah, things not to do – all those things we just mentioned.

Tom: Yeah. So this is a key point though. And I really want to drive this home. As an entrepreneur, as just people in life, we’re going to make mistakes and mistakes are only mistakes if you don’t learn or do something from them.

Ariana: Yes.

Tom: So this could have been a point where we stopped. We could have had arguments. We could really made this a big contention point but what we did instead was actually sit down and said, what’s done is done. Where do we go from here?

Ariana: Let’s make the most of it.


Tom: Yep, and out of that training course, I think there were 40 people in there, only one or two people actually went and took action, all the rest of the people spent all that money and then never did anything with it. And if we had been one of those people, we wouldn’t be here with this podcast now, with our multiple businesses at this point in our life. We’d be back, probably not happy, working our jobs.

Ariana: Yep, so a big question that we want to answer for everyone is why do we push multiple streams of income?

Tom: Yep, and the first one is really reducing your risk. So, we’re going probably have some deeper shows on this in the future, but if you only have one income stream and let me just clarify, I talk about everything as an income stream because whether it’s your job or a business or an investment, if it’s bringing you in money, it’s an income stream. So I like to generalize things that way. But let’s say you just have a job. If you lose that job, now all of your money is cut off.


Tom: So by having multiple income streams, if one of them goes down, like if a business goes south or if you lose your job, the other ones are there to hopefully support you. And I look at this like I look at the stock market. You don’t just buy one stock and hope that goes up. You diversify by buying a couple different stocks or making sure that your income or your wealth is going to grow through that. So multiple businesses give you that flexibility.

Ariana: Another reason is just more income. A big problem that most people have is that their income is less than their expenses. Every month you’re spending more than you’re making.  Multiple streams of income means that you literally are creating more income for yourself every month. So you know, any business that you have, once your business is successful, if you still are working your job, now you’re adding the side business on, you’ve got your income from your job, you have you income from your side business, you start another one – you have more income from that business.


Ariana: And you can continue to grow and grow and grow and then if you’re investing that income or if you’re putting it back into your businesses, you’re just creating more income on top of that. So you know, who doesn’t want more and more money?

Tom: And from that, if that income gets high enough from your other income streams, that gives a lot of people the flexibility to leave their job if that’s what they want to do.

Ariana: If that’s the end goal.

Tom: If they don’t want to leave their job, now they have cushion. Now they have actual money to buy nicer things or go on vacation or whatever.

Ariana: Or save it up for something big.

Tom: Yeah. Alright, and third point here for why we like multiple income streams is you don’t have to hit home runs. And what I mean by that is, if you are only working a job, typically the only way to make more money is be the best at that job and move up. If you’re trying to start a business and you only have that one business, you have to make that the best business and you have to keep growing it likely to bring in more revenue.


Tom: But with multiple income streams, you can start to find smaller niches or smaller areas where other people maybe aren’t in there because a big company looks at that and says there’s not enough money there. So it may not be enough money for a big company, but it could be good enough for you. So a great example of that is a liquor store. So our liquor store is in a small town and the only reason we’re able to operate there is because these large discount liquor stores don’t look at that town because it’s not big enough for them.

Ariana: And they’re further away as well. They’re in bigger cities.

Tom: Exactly. So when you’re looking at multiple income streams, you don’t have to have the biggest store or the best business or be the best employee. You just have to find where that niche is, put the right amount of effort into getting that to a good point and you can go and find another one and duplicate that.

Ariana: Knowing the market.


Tom: Absolutely. So, from there, why did we start this podcast? And one of the big drivers for us and me specifically was I think there are far too many people out there that are selling the dream of how to start a business, how to quit your job, live on a beach, and never work again. And although that probably can happen for some people, the reality is it’s not going to happen for most and that may not even be what most people want. What I think most people want from talking and coaching a variety of people is that they want real information and they really need support from someone who’s actually done it, not someone who’s making all their money from telling people how to make all their money. And with that, like I said, when I spent all that money on that credit card, I mean I feel for their trap. I feel for their sales pitch. And I know other people too, that that’s actually ruined their relationships and you know, like I said – those guys are very good at selling and what we want to make sure we’re giving you is real information about what business actually looks, and not only what business looks like but everything else that goes along with that.


Ariana: Yeah, too many people are worried about building the businesses and they forget about having that relationship whether it’s with a spouse or family members or friends. A lot of people get caught up with how much money they’re spending, how much money they need, they get caught up with the time consuming part of building the business and it can really throw off the rest of the aspects in your life. And then another part of that is actual couples that are entrepreneurs together. There are not a lot of people out there talking about that and talking about how to do that without driving each other crazy. Another reason we started this podcast is to really help a lot of people out there that are building their business, also help them build their relationships. It’s easy to get caught up with doing all the work for your business and forget about the people around you; your spouse, your family, your friends. So we want to give as much information as we have from ourselves dealing with all of that, telling people that you’re starting a business and them looking at you like you’re crazy.


Tom: It’s not going to work.

Ariana: Having the time issues, not being able to go to the parties or to family gatherings because you’re busy and you’re doing work, having to explain that to people and to get them to understand why you have to do that. And then also to help people continue to have a thriving relationship with their own spouse whether you’re working together on the business or if one of you is doing the business and the other is working or staying home with the kids or whatever you happen to have your situation be, we want to make sure that whatever mistakes we’ve made, experiences that we’ve had with doing, we want to share that with everyone and try to help them get along.

Tom: And to be honest, this is tough. And this is what we wish we would have had when we started.

Ariana: Yes.

Tom: There’s a ton of information out there to start a business and there’s a lot of good information out there too, but the challenge is everyone focuses on the business stuff and I’ll say from my experience, I’ve always been more into the business stuff.


Tom: And I have struggled over the years of how do I balance the family stuff and the life stuff? And Ariana has probably been a little bit on the other side.

Ariana: Which is why I’m the reality checker.

Tom: Absolutely. And we’re going to share real stories and real experiences and the struggles that we go through to show you guys that people always see the positives. People always see when people are successful but what we don’t often see and what we like to do is kind of pull back the curtain and say, what do our real lives look like? What challenges do we face? What failures have we had? Because we’ve had so many failures.

Ariana: Yep.

Tom: And we’ll get into a lot of those on the show, but really just give you guys real information. That’s what we want to do here.

Ariana: Yeah, so what you can expect from us with all that great information, we’re going to try to have a lot of content for you and funny stories as well. And basically to help you start your first business or if you already have one, help you start your additional businesses.


Tom: Yeah, so like we said earlier, we’re married. Actually, now that I’m saying this…

Ariana: Our anniversary is tomorrow!

Tom: It is tomorrow.

Ariana: Wait, what year are we on?

Tom: Seven?

Ariana: I think so. 2008…yeah seven!

Tom: Yeah so this is what happens when you’re running a business, trying to get your podcast going, you forget about your anniversary.

Ariana: Happy anniversary!

Tom: I love you.

Ariana: I love you.

Tom: So, we’re married. We’re parents. We have a three and a half year old daughter Alaina and we have two half month old son Ty. And you’re going to hear the stories and the ups and downs of not only being an entrepreneur but how you be a parent as well.

Ariana: You may also hear some noise in the background because they live here.

Tom: Because they’re upstairs right now. And really just sharing what early retirement means for us and how we’ve progressed there. Your path doesn’t have to be the same as us. But we can give you hopefully some experiences and some guidance along the way to avoid and learn from some of our mistakes.


Ariana: Yep, I was lucky enough to leave my fulltime job when we got pregnant with Alaina and then when we had her, I was able to stay home fulltime and raise her and have all the fun times at home and also work from on the businesses which was very helpful for Tom because he’s still working fulltime. So me being home has really helped us grow the businesses because we have that freedom to add different tasks on and for me to go and actually physically be at the retail wine and liquor store when needed. It’s helped us a lot.

Tom: Yeah and what we’ll get into later on to is we are big on goal planning, to be able to get to some of these things. So we’ve laid out our goals. One of our goals was to have Ariana leave her job and she was able to do that. Obviously to get to being retired by 35, that means me eventually leaving my job and we’ve been taking steps to transition me away from a fulltime job.


Tom: Now I’m into doing a lot more consulting which not only helps with our businesses but is a step towards being able to leave a job and then we’re on that path to be able to have our retirement by 35 which I think is pretty cool.

Ariana: Yeah. Another thing you’ll hear on our podcast – we’re going to bring some other entrepreneurs on for interviews, live interviews. We want to talk to as many people as we can at various stages of building their business whether it’s from the ground up and they haven’t started yet or if they’re already successful business owner or a multiple business owner. We want to bring their experiences to you as well as ours. Talk about the ups and downs, the failures, the successes, funny stories that they may have and then also we want to bring the aspect of a variety of businesses. Because you know, we have a couple different types of businesses but then there’s so many other people out there that do so many different things, we think that it will be a unique experience to have them come and talk about their own personal business.


Tom: Yeah, and with this, a lot of times when podcasts like this and people come on for interviews, it’s a lot of the same people and you hear a lot of the same stories. And so we’ll probably have some of those kinds of people on but a big focus for us is going to be really different entrepreneurs that are probably closer to your level and stories and experiences and industries you might not have heard before. And then from there, we’re also going to probably do some of our coaching live on this podcast. So we really enjoy helping entrepreneurs get started. We actually have a free community for other entrepreneurs to help support each other. So you guys can check that out at sscommunity.co. That’s .co. And that will get you over to our free Facebook community that we have for entrepreneurs. But we really enjoy helping other entrepreneurs out and being able to pull them on and actually do that coaching on the podcast, will then leverage the information not just between us and them but for all of you guys as well.


Ariana: We might even at some point do live questions and answers or have questions off of the Facebook page to answer on the podcast.

Tom: Yeah so let us know what you guys want to hear out of this. What experiences you want to pull from us or what experiences you want from other people and we’ll adopt and adapt as we go.

Ariana: Okay so now for our tip of the week.

Tom: Yeah so we’re going to end every show with a tip. It may be a tool, it may be a lesson we’ve learned and our tip for this week is really based on a quote. So there’s a quote that hopefully you guys have heard that, you are the sum of the five people that you surround yourself with. And that was said by Jim Rohn. And we really believe that. So as you get into business, and even if you look at your life now – if you look at the five people that are around you, you’re probably very similar to them. So if they’re very successful, you’re probably very successful. If they work out a lot, you probably work out a lot.


Tom: So what we want to help you guys out with here is making sure that if you don’t have those five people around you right now, we’re building that community to help you. So as I mentioned, jump over to sscommunity.co and we’ll give you access to our private Facebook page which is a community of other entrepreneurs, other couples, and we’re going to be in there really helping answer questions, start topics, and figure out, how do we do this entrepreneurial thing together as a community.

Ariana: Yep, so I think that’s our show for this week. Thank you guys so much for listening. And we will talk to you again next week.

Tom: Alright, thanks guys.