She’s the DJ, He’s the Rapper. 🙂
Tom and Ariana Sylvester are the founders of Serial Startups, and host of the podcast of the same name. They are experienced real estate investors, as well owning other businesses. Together, they raise two adorable children.
Tom’s first entrepreneurial venture was as a child. He purchased candy in bulk from the local store, and set up his own shop in his room. Over the years, he had several businesses fail, until he started seeing success with his real estate investing. When he and Ariana purchased a commercial building, they used the empty space to open their own wine and liquor store.
People were asking the two of them how they managed being parents while running multiple businesses. They decided to shift their conversations online by starting a blog, which evolved into the podcast and courses related to Serial Startups.
Tom went to school for computer science and business management, while Ariana studied zoology. She worked a number of jobs, including at an animal hospital and in an office an administrative assistant, and credits these experiences as helping her learn the various skills she uses in their businesses today.
Tom believes communication is key in any business, as well as utilizing the different strengths that both of them have.
They originally met in college, living in the same dorm.
“It was a very comfortable, automatic friendship that very quickly turned into a relationship”
From early on, Tom wanted them to not be working for anyone else by age of 35. He started investing in the stock market, but realized it wasn’t the vehicle for him to reach this goal. He also started an IT consultancy business with a friend, which they sold after two years.
“The thing was figuring out what didn’t work with these businesses. Then we could apply that to all the things we did after that point, which helped us succeed”
Ariana says the hardest part about being an entrepreneur’s spouse was watching him go through various failures over the years. She played the role of the “voice of reason”, as well as “cheerleader” at various times.
Due to ignorance coming out of college, they accumulated a large amount of debt, but were able to pay this off. They did so by understanding their finances (how much money was coming in, versus how much going out) and by making sacrifices like not eating out and cancelling their cable.
It can be challenging working with a spouse, but they’ve learned to communicate so that arguments don’t become larger issues.
“We never go to bed early” (Ariana)
Tom – Batman
Ariana – wasn’t allowed to watch those type of shows as a kid
Tom – Teenage Mutant Ninja Turtles
Ariana – Carebears
Tom – driving around with his family looking at Christmas lights
Ariana – Thanksgiving Day with her family, eating and playing games together
Tom – thinking a flooded toilet in kindergarten was a result of ghosts (he was a big Ghostbusters fan)
Ariana – getting her hair cut too short before school photos and being mistaken for a boy
Proudest Moment as Parents:
Tom – seeing his daughter acting like him, and talking on a phone
Ariana – the little moments where she knows her kids are listening and learning from them
One Thing You Adore About Each Other:
Tom – the fact she puts up with him
Ariana – he’s the most motivated person she’s ever met and always wants the best for his family