Ryan Allaire Interview

Ryan Allaire Interview

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This time we’re going to be doing a deep dive with a guy who is absolutely crushing it in direct marketing, but Ryan Allaire’s story starts out when he and his family were living in a cramped motel room so I think this is going to be a really fascinating and inspirational conversation. He’s also one of the most energetic guys you’re ever going to meet. Ryan, it’s a real pleasure to connect with you.

Ryan Allaire:

Thank you so much. Thanks for having me. It’s so great to be here and so awesome to be here.


Well, I’m really looking forward to chatting with you, Ryan, because your story couldn’t be more rags to riches. Is it true you got started in marketing at just the tender age of 13?

Ryan Allaire:

Yes, yes it is. You’re right, it’s kind of a cliché rags to riches story which I kind of struggle with because I’m like, “Oh, it’s just another story.” But to me it’s been a unique experience. It started at the age of 13, like you said in the intro, growing up in a motel room is a true story. I grew up, or I take it back, we lived out of a motel room for a while, grew up in Florida, and we were there for probably over a year, closer to two. And it was a humbling time. My parents always struggled with making money and I’ve always watched them struggle with that. Then I had a friend and his parents and it was like the complete opposite.

It’s like everywhere we went it’s like money was just running into them, they couldn’t repel it. It was so interesting how I would watch someone struggle, and someone make it so effortlessly and have multiple nice vehicles and multiple homes and vacation homes and had multiple estates.

Just this completely different life because here we are trying to make it in a motel room and then my parents rented homes, we got evicted, we’d have the electricity turned off, the water turned off, and it’s funny, some nights we would have candles and looking back, some of those were the best moments with my siblings and with my family and my parents are great people, I love them, they’re probably the hardest workers I know if I’m being truthful and transparent.

They are super hard workers, but the irony of all this and what it taught me at a young age is not really just how hard you work, it’s also how you work and how you apply the work you’re doing because I watched my mentor, and he worked hard but nowhere near, my mom would detail boats, she worked in a fruit field and they gathered oranges, and they’d get them ready and polish them to sell in farmers markets and fruit stands. My dad was in sales, so I kind of got that from him and he worked his long hours doing these moving sales jobs, and I’d watch them work all the time, but never get ahead.

There’s been times they would in the states that have an income tax where you get back a portion of your taxes, so for about a week or two we’d go all out. I was kind of looking back, the typical poor thing poor people do, you blow all your money the second you get some. But we’d go to the carnival. My parents did the best they could just to be fair and I love them to death, but the crazy part is is at 13 years old, the writing on the wall was very clear, meaning it’s not just how hard you work, it’s working hard and working smart at the same time, and this is how I got into direct mail.

I worked in a mail room, I would walk in and funny story, I was actually working at a golf course and also McDonald’s before this, and this was kind of a part-time thing I would do with my friend whenever I was with him, we’d go into his parents office, his dad’s office, and then we would do odd jobs for $20, $50.

And we’d help with something small, and to me that was exciting because I got to bring home some money and make some money while I was there.
And I ended up actually transitioning from working at McDonald’s at 14 and also this golf course, to working for them full-time because I realized I could work in a nice, cool office, the golf course was super hot, and a lot of hard work.

I’m weed whipping around lakes and divets and all these things on the golf course in Florida, so just imagine that.
And then McDonald’s, I don’t care where you are in the world, a greasy fast food restaurant is never fun, right?
In any climate.

So, I realized, hey, I can make more money than all my friends, I can sit in this really nice, cushy chair in this beautiful office, and I worked inside of a mail room, meaning I would help get direct mail piece mailings ready, send them out, then we would fulfill different products that they were selling through the mail, and this is when it came full circle.

Because I got to see exactly how it worked, because I knew it started out with them sending out four page letter, six page letter, sometimes a 10 page letter, but basically a bundle of paper, right?

They’d mail it out and then from there I would watch them sell products that would range from $20, $40, $50, $100 and then some products were even thousands, which I’ll talk more about that in a second, those are things they would sell on the back end.
But anyways, so I would watch this process and I’m like, wow, literally these people are making millions of dollars by sending out a couple pieces of paper and postage, the envelope, and selling these products.

In the time it was in personal development.
This was in the late ’90s going into the early 2000s and Mary Kay was very popular, and they actually had product packages and books and things that would help a lot of Mary Kay agents and people that were in the Mary Kay cosmetic business.

It was interesting because I got to see people from all walks of life.

What’s funny is you could always spot the Mary Kay ladies because their email addresses would be like…

And I don’t know if you know this, but in the Mary Kay business, when you achieve a certain level, they gift you a car, but you have to paint it pink, actually it was Cadillacs.

What’s funny, and get this, it’s crazy, I was actually driving one of my sports cars down the road and I’m like oh my gosh, that’s an interesting Cadillac, because it was like this magenta pink, it was a really interesting colour pink, and I got closer up to it and sure enough it said, “Mary Kay Specialist, and had her website below it.



Ryan Allaire:

So, today, in 2021, they are still giving out pink Cadillacs, which is pretty funny. But yeah.
So, it was crazy, it was just all walks of life, from younger people, these Mary Kay specialists, I would go ahead and I worked in the mail room and then finally I would hear my, so it was kind of a family business where my friend worked there.

His dad owned the business, his parents were working there was well, and they were retirement age, the one was an educator in a school, public school here in America, so he was working there and actually had like 20 staff members total.

So, I would go from the mail room to I would walk over when the phones would get busy and I would pick up the phone just to help basically take orders over the phone, because what happened is they would mail out a direct mail piece, and then people would get those.

The internet was still kind of new but they had the capability to go online and check out, but it was still a newer thing.
Most people either sent back the order form with a check, money order, cash, or they filled out a credit card on the order
form or they would call in the office and place an order that way.

Again, funny story, kind of like the Mary Kay story, right? Almost 20 years later, we still do the exact same process.


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