How Jess Guevara Manages Her Fitness Business from Anywhere in the World (with Tailwind!)

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Jess Guevara lives a life that – let’s be honest – we’re more than a little jealous of. The Pilates instructor slash fitness coach slash traveler slash content creator is currently splitting her time between Las Vegas and  Santa Teresa, a beach town in Costa Rica. In fact, that’s where she dialed in for her interview with us after a five-hour power outage nearly rescheduled our sit-down!

When she’s not enjoying the sounds of toucans calling and monkeys climbing in the trees around her home, Jess runs a full-time business teaching Pilates and coaching clients on diet, fitness, and health. 

She got her start in 2011 when she suffered a knee injury from running and kickboxing. Her roommate got tired of hearing Jess complain about not being able to work out, and suggested she try out the new Pilates studio that opened around the corner in Miami Beach for the low-impact training benefits.

“I took one class and I was like, whoa, this is the most invigorating workout I’ve ever taken where I don’t feel like I’m crawling out of the class. I feel really good about myself!”

Jess was officially on the Pilates train and the rest is history. She pursued her certification in becoming a Pilates instructor, an adventure that took her around the world. Jess taught Pilates in Miami, Los Angeles, New York City, Sydney, and even Dubai!

Getting Started on Instagram

“I moved to Beverly Hills in 2016, and I kind of started seeing all these other girls post workout videos online. And I just started feeling, this was gonna be like a thing. I kind of want to join that.”

Her first adventures on Instagram were, in her words, a little awkward.

“I wouldn’t even speak, I don’t think I even added music… I was so awkward. My sister’s like, can you please say something on camera? I was just so shy, you know? So that’s how it first started. Yeah, it was pretty bad.”

But Jess soon moved beyond her initial shyness and got more comfortable showing off her knowledge and expertise on Instagram. And a possibility began to take shape in her mind!

“I was researching marketing and starting to figure out, how can I really make money online and how can I turn this into a career?”

“Because I always wanted what I have now, like financial freedom and physical freedom that I can work and do what I want anywhere.” 

Jess Guevara

By 2020, Jess was ready to take the leap. 

“I said, you know what, I’m doing it. I’m just gonna move back home to Vegas and I’m going to go all-in on this online stuff. 

I went all the way in, you know. There was the point of no return.” Goes Live

Jess hit the ground running by training clients virtually, and expanding her offering. Soon, she was offering a 12-week postpartum mommy program and helping clients with low back issues. Her blog soon followed. Little by little, she kept diving in deeper and deeper!

Thumbnails of Pilates and workout courses offered by Jess Guevara (
Jess offers Pilates and specialty targeting exercise courses on her website.

Did it all go perfectly? Of course not. But overall the biggest difficulty in her business was similar to one we hear all the time from our members – investing in yourself and believing you can do it.

Jess had to reach a decision point to invest in herself and create a budget for investing in marketing courses, software, and filming equipment, which raised an important question to wrestle with.

“I was like ‘is this a hobby? Or this is a business?’ I was like… ‘I think it’s a business, not a hobby.’ 

That was the scary part, is looking at it like this is an investment, this is my business. And this is what I want to do.”


Priceless Advice for Conquering Limiting Beliefs

Finding the confidence to battle limiting beliefs and simply believe was one of the hardest things for Jess to overcome, and she still battles it to this day.

“It was really hard to get past my own mental blocks, you know? Because entrepreneurship is all about your head space.

Waking up in the morning, being tired or having a long day and having to be like ‘nope, you gotta do this. Let’s go. Just get the pep in the step, drink your coffee, work, do what you gotta do.’ Doing that day in and day out can be exhausting and lead to burnout.”

So Jess started journaling and really looking at all the things that were coming up and causing her anxiety.

‘Okay, is this 911? Are you just freaking yourself out? What’s in your control?’ It’s never gonna be perfect. 

“So I’ve learned how to manage all those different emotions and juggle everything.”

Finding Success on Pinterest

Pinterest always made sense for JG Pilates as a platform from the start, because in working with mostly women, busy moms, and career women in the studios, Pinterest is where they would go to get ideas.

“Pinterest is a place of inspiration. So, if you want to put together a really pretty Pin or a creative blog, it feeds that fire as a creator because Pinterest rewards you more for being unique and creative.”

The other element that made Pinterest perfect for Jess was the visual search engine aspect and the longevity of content on the platform.

“If you post a video on Tiktok or Instagram, you better pray to the viral gods that it goes viral. Or it’s like you just wasted all that time on one video. But the cool part about Pinterest is that I was looking at my analytics and I’m still getting engagement from a Pin I Pinned 18 months ago. I looked at it and I was like, ‘what?!’ I even forgot I created that video.

So that’s the best part as a creator and business owner is that it’s a search engine. Your hard work is constantly rewarded.”

Managing Social Media Marketing with Tailwind

“I initially signed up for Tailwind because I was using Pinterest. At that time I think I was manually doing everything. I don’t know how I came across Tailwind, but I remember I bought it on a Black Friday or Cyber Monday. I was like score, saved money!”

Was it love at first sight? Not exactly.

“I didn’t use it for like two months of course. Standard.” #Relatable, though, right? We’ve all done it where we buy software or a product that we think will change our life – and then we just forget to get started!

But Jess recommitted to her goal to use Tailwind. “I’m like, no, you need to log in. You need to use it. And I’m really happy I did! I love Tailwind.”

Jess quickly realized that Tailwind could save her so much time, especially because she had been manually uploading all her Pins. Now, she could upload and schedule all her Pins and videos in a flash, batch scheduling her content.

“I would say it’s not even just a scheduler. It does so much! You have analytics – and they’re solid analytics with your Google and Pinterest. If there’s one thing you gotta know, it’s your analytics in your business.”

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With Tailwind, Jess also found a solution to help her content have a longer life.

“All the work you go into creating a piece of content… Tailwind helps me repurpose it across different social media platforms.”

“You spend all this time and energy writing the perfect caption, researching all the hashtags, creating the creative. And it could be an hour on that one little video… so all your hard work doesn’t go down the toilet.
You’re like, oh this is a great piece of content and it could keep living.”

What’s Next for JG Pilates?

Now that business is booming for Jess, and content creation is easier than ever, the Pilates instructor has big goals for the future.

“I felt as though I always had to pick between my Pilates side and my content creator side. For work, I have private clients that I teach, and online workouts and all that great stuff. But at the same time, I’ve worked with a lot of companies and brands where I create content.

“Something I’d really like to do is combine the two and I would love to help other future content creators. I’ve hit the wall so many times, and cried and been frustrated. I’ve been like, ‘I’m just going to go get a job, this sucks!’

I’ve been there so many times and I would love to help other future content creators with creating workflows, organizing themselves, and things like that.

“I could still be the Pilates girl, but I could also be the content creator girl, too!”

Want to keep up with Jess? Check out her shop, blog, and program offerings at! You can also follow her on Facebook, Instagram, Pinterest, and Tiktok!

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Jess Guevara manages a thriving Pilates business from some truly exotic locations. Find out how she uses Tailwind to keep track of her marketing while she lives her dream!

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