From Accountant to Island Designer Brand

Summary

Episode Overview

Podcast: Living Your Legacy
Host: Rudy Mawer (with guest host Ray Gutierrez)
Guest: Erica Pruss, Founder of Olakala Bags
Episode Title: From Accountant to Island Designer Brand
Date: May 7, 2026

Theme/Purpose:
This episode explores Erica Pruss’s transformative journey from corporate accountant in a family cabinetry business to founder of Olakala Bags, an island-inspired designer brand. Through candid conversation, Erica shares her insights on reinvention, creativity, and the power of trusting one’s instincts. The episode unpacks the value of embracing change, the challenges of entrepreneurship, and what it means to be a woman in power.

---

Key Discussion Points and Insights

1. Beginnings and Roots in Craftsmanship ([03:05–05:15])

• Erica recounts her childhood and career:
  • Grew up in the family’s high-end cabinetry business in Colorado, serving residences in Vail, Aspen, and major hotels (e.g., One South Beach).
  • Spent 30 years in the business, shifting to the role of company accountant after a mishap on the shop floor.
  • Though successful and comfortable, it was never her dream:
    “I always wanted something of my own and something different.” ([03:56], A)

2. The Breaking Point and Awakening ([05:31–07:18])

• The COVID pandemic catalyzed self-reflection across the globe.
• A transformative sailing trip to the Virgin Islands helped Erica rediscover her true self:
  • Notable moment:
    “The captain goes, ‘Well, there’s our smiling bundle of positive energy.’...And I thought, where the hell has that girl been? Thank God she’s not dead.” ([05:54–06:37], A)
  • The captain later becomes her life partner, who “made [her] believe in [herself] again.” ([07:18], A)

3. From Numbers to Nautical: Launching Olakala Bags ([08:04–10:30])

• After moving to the Virgin Islands, Erica noticed the absence of luxury handbag stores post-hurricane.
• Inspired by her partner:
  “My boyfriend was like, why don’t you start designing them? And I thought, what the hell, why not?” ([08:45], A)
• The creative journey began with designing bags in Excel:
  “You just move the cells around… coloring in the lines. Then I had to figure out how to put pencil and paper and color outside the lines.” ([09:28–09:41], A)
• With the help of a friend from grad school and a connection to a Miami fashion school, Erica launched Olakala Bags in April 2024.

4. The Art and Philosophy Behind Olakala Bags ([10:56–12:09])

• Each bag tells a story, reflecting Erica’s journey from Colorado to the Virgin Islands:
  • Combines elements from her mountain upbringing (leather, wood) with island life (raffia, nautical themes).
  • Notable design detail:
    “The inside of the bags have a nautical map… as a reminder for people to kind of look within. And… have the confidence and courage to change that course if you’re not on the one you want.” ([11:38], A)
• Design process and inspiration:
  • Balances technical, “numbers” side with newfound creativity.
  • Many ideas come to her while snorkeling:
    “That’s where I find my ideas. And it’s where I do my best thinking.” ([13:15], A)

5. Overcoming Fear of the Unknown ([10:17–10:30], [12:56])

• Erica discusses the challenges of entrepreneurship:
  • “You don’t know what you don’t know. And I really knew nothing.” ([10:17], A)
  • She stresses the importance of seeking help and learning what’s needed, even when it’s daunting.

6. Defining Success and a Woman’s Power ([00:58], [15:55])

• On what it means to be a woman in power:
  “To be a woman in power is to inspire women to really just realize that it’s never too late to start over at any age. And there’s really nothing you can’t do. You can learn anything. Especially today. It's all about who you know, and whether you are willing to put the work and the time into figuring it out. It's a marathon, not a sprint." ([15:55–16:20], A)
• Encouraging reinvention, risk-taking, and resilience regardless of age or circumstance.

---

Notable Quotes & Memorable Moments

• “Numbers don’t lie.” ([05:00], A)
• “He made me believe in myself again.” ([07:18], A)
• “I always get ideas when I’m snorkeling. That’s where I do my best thinking.” ([13:15], A)
• “My competition is really, there aren’t a lot of companies in the United States who have handbags made in Spain and they’re all European companies and they don’t sell in the US, you know.” ([15:23], A)
• Host Ray Gutierrez:
  “Literally a blue ocean strategy. See what I did there? I connected the dots.” ([15:43], B)
• On reinvention:
  “It’s never too late to start over at any age.” ([00:58 & 15:55], A)

---

Important Segments & Timestamps

• [03:05] – Erica’s early years in the family business
• [05:31] – COVID as catalyst and transformative sailing trip
• [06:37] – Key realization and meeting her life partner
• [08:15] – Introduction to Olakala Bags and the spark to start the business
• [09:17] – Designing bags in Excel and transitioning to more creative mediums
• [11:37] – Story, materials, and symbolic design choices in her bags
• [13:15] – Creativity through snorkeling and island inspiration
• [15:55] – Defining “a woman in power” and closing wisdom

---

Where to Find Olakala Bags

• Website: olakalabags.com
• Instagram: @olakalabags
• Sold in select high-end boutiques across the country and on St. John, USVI
• Handmade in Spain, emphasizing quality and artistry over mass production ([14:43–14:48], A)

---

Final Thoughts

Erica Pruss’s journey is a testament to the power of personal reinvention, creative risk-taking, and drawing inspiration from both one’s roots and new adventures. The episode is a motivational resource for aspiring entrepreneurs, creatives, and anyone who needs permission to start over—no matter where they are in life. Her closing message rings clear: It’s never too late to change your course.

Transcript

[A]

When you stop all the noise and you just like, are present in, you know, kind of serenity and you start to find yourself again.

[B]

Erica Pruss is a creative visionary and detail driven entrepreneur and the founder of Olakala Bags. Drawing from her background in luxury design and a transformative journey into island living, she blends craftsmanship and coastal inspiration to create pieces that reflect freedom, artistry, and a life lived on her own terms. I love the fact that it's. Each piece of the bag comes from a different part of your story, your adventures, your travel, or, you know, the poetry of the day.

[A]

All of my bags kind of combine my journeys. The inside of the bags have an interior. They have a nautical map as a reminder for people to kind of look within. Right. And take note of the course you're on and have the confidence and courage to change that course if you're not on the one you want.

[B]

What does it mean to be a woman in power?

[A]

To be a woman in power is to inspire women to really just realize that it's never too late to start over at any age. And there's really nothing you can't do.

[B]

It spans the globe like a super high cold Internet. Elvis Presley for free. Today, Apple is going to reinvent the phone. It's not over until I win the Living youg Legacy podcast cast for those who live to leave a legacy. Oh, that is sensational. Jordan, open Chicago with the lead. You said Paul is the fastest man on the planet. You can live your dream. Welcome to another episode of the Living your Legacy podcast, the Women in Power edition. For Inside Success, I am Ray Gutierrez. Joining me today is a unique, powerful woman. I like to call her a mermaid, if you will. A mermaid. That is the founder of Olakala Bags, Kala, meaning all as well, correct?

[A]

Yep. Olakala is Greek and means all is well.

[B]

I was paying attention.

[A]

Good job.

[B]

Welcome to the show. Who are you? What brings you here?

[A]

My name is Erica and I'm the founder and designer of Olakala Bags. Right on. I started it. April of 2024 is when I launched the company.

[B]

Right on. How's the last year been?

[A]

It's been good. It's been a big learning curve, but it's going well. Yeah.

[B]

We just literally finished filming your episode. Give us a small preview. What are we gonna learn about you?

[A]

My episode is really an inspiring story that it's never too late to reinvent yourself at any age.

[B]

I'm kind of curious. Where should we begin? Your adventures and your story begin kind of like in a traditional way with your family. Let's start there. Where did you begin? Let's start with your entrepreneur journey. Your first nail to hammer.

[A]

All right, so I grew up in a family business in Colorado. We did high end custom cabinetry, millwork and doors.

[B]

Right.

[A]

On four high end residences in Vail and Aspen and high end hotels. We actually did the one south beach down here.

[B]

Oh, wow.

[A]

Yeah, but that's where I grew up. It was where I spent my 30 year career working in the business. Well, I started as a young kid in the shop and then I actually got fired from the shop floor. Cause I drilled a bunch of doors as lefts instead of rights or rights in front of whatever. Anyway, that got me an office job. I became an accountant after that, took over my mom's role and worked there 30 years.

[B]

30 years.

[A]

And was just, I guess, doing the comfortable route. But that was never my dream and I always wanted something of my own and something different. I went on a. Do you want me to go into that now?

[B]

Go ahead, Sure. I was just going to say, I'm just picturing you in a very loud factory in a tiny office, like tinkering away for 30 years.

[A]

30 years doing the same thing.

[B]

That's like a lifetime. An entrepreneur. That's like a life and death. Life and death.

[A]

I had a work, you know, in a government job. I'd have been retired by now. Right?

[B]

For sure. But I mean like, wow, good for you for just kind of like staying on the wagon, man.

[A]

Yeah, right on. I mean, I. I plugged away, but yeah, it was probably never my ultimate job. What I wanted to do, I guess

[B]

was with my life in 30 years. Did the numbers change? What changed around you? I almost feel like there's like a time warp happening. You're like. And like reality's changing behind you and things are moving and presidents are changing, but the numbers stay the same. Math.

[A]

Numbers don't lie.

[B]

Death and taxes.

[A]

Yep. Numbers don't lie. You know, I think I was just checking off boxes, like just plugging away, like boom, boom, boom, boom, boom. And then before you know it, it's like, dang.

[B]

Yeah. But I'm sure you were comfortable making good money.

[A]

I mean, I had a great career, my family, you know, that's a great business. I have a great family. I've always like been that adventure girl at heart. And I just buried her. Wow. Yeah.

[B]

What was it? Was it an ayahuasca trip? What's his name? Like, what changed you? What was the breaking point?

[A]

I. I think Covid practically broke everybody Right, Sure.

[B]

It definitely tested everyone.

[A]

Yeah, it definitely tested everybody. And after that, I. On a sailing trip to the Virgin Islands with a bunch of women from my tennis team.

[B]

Right on.

[A]

And a potluck captain. Whatever. And so anyway, we were down there a week, and I think it was like, on the second or third day, I came up from my cabin, and the captain was in the kitchen, and I'm coming up the stairs, and he goes, well, there's our smiling bundle of positive energy. And I thought, like, it stopped me in my tracks. I'll never forget it. And it was because I was like, whoa. Like, how does this guy who never met me have me figured out in no time? And then two, like, where the hell has that girl been? And then three, thank God she's not dead.

[B]

Wow.

[A]

Right? So that's amazing. That was kind of the turning point of. Yeah, dude, what are you doing? Like, life's a great big world out there.

[B]

It's quite ironic that a captain found your lighthouse and your, like, it's inside of you, and that was the turning point. This is something we didn't actually speak about in your episode that we're going to talk about in your podcast, so insert edit here. This captain happens to be your husband today.

[A]

Well, he's my boyfriend.

[B]

Boyfriend. I keep confusing that. Your life partner. These binary titles that humans use is so boring. I know, but you met this person that reignited a fire that's always been inside you, and that's always fire.

[A]

He made. He made me believe in myself again.

[B]

Oh, yeah, yeah, yeah. And it doesn't take anything away from being a woman. Like, I. I. My partner reinvigorated my. My passion that I laid dormant for quite a while. I'm like, I'm done with that noise. I'm done with the. The jibber jabber on camera.

[A]

Right.

[B]

And then I'm like. But no, I'm clearly doing it again. I'm having a lot of fun. And it's coming from a place of. Of. Of healing, not from torment.

[A]

Yeah, it is. It's healing. And it's. It's, like, reinvigorating and inspiring because when you stop all the noise and you just are present in kind of serenity and whatever, you start to find yourself again.

[B]

Yeah. Talk about finding yourself and how you turned your energy into these amazing pieces of artwork. What do we have here that's just been hanging out like a droid?

[A]

This is one of the Olakala bags. So this is supposed to represent kind of a wave, obviously, but yeah, so this is One of my first collection. This is just a new color that's come out. But when I moved to the Virgin Islands, I had no idea what I was going to do. I was ending my career with the family business, and one day I was walking around and looking for handbags because I've always loved handbags, but there was no handbag stores.

[B]

Wow.

[A]

And I guess prior to the hurricane in 2017, they had, you know, Louis Vuitton and all these high end shops, and now there are no high end handbag stores. And so, you know, my boyfriend was like, well, why don't you start designing them? And I thought, what the hell, why not?

[B]

Yeah, why not? I'm like, huh?

[A]

I'm like, yeah, maybe I should. So he kind of like gave me the idea and then I started designing them in Excel.

[B]

That's the part I wanted. You land on, like. So homegirl over here, accounting over here, grabs Excel. I'm going to design a handbag.

[A]

Yeah.

[B]

Oh, boy. How does. How does one design a handbag in Excel?

[A]

You know, you just move the cells

[B]

around so you're kind of like pixel mapping. You're moving these pixels and creating, like

[A]

coloring in the lines. So then I had to figure out how to put pencil and paper and color outside the lines.

[B]

Gotcha. Gotcha. So what was the next step? Who would you call? Who did you call next? And when they stopped laughing at you, what happened next?

[A]

Yeah, that was like beating your head against the wall for a long time. And then one of my friends from grad school actually had a neighbor who works at a fashion school here in Miami.

[B]

Oh, right on.

[A]

And knew somebody that I worked with her in kind of launching my brand. And she really helped me tremendously on finding a fact and just mapping things out. Because you don't know what you don't know. And I really knew nothing.

[B]

Yeah. The unknown is what petrifies me. Making these giant entrepreneurial moves. I'm like, that sounds like impulsive moves that Ray on a good day would do on a dopamine high when there was really no thought and reason to that decision.

[A]

Yeah.

[B]

So that terrifies me. So when Rey's in a really good mood, maybe he's in too much of a good mood. There's gotta be some thought to the. You know what I mean? And I learned that, unfortunately from Rudy, where he's just like, always, like, floating. Like, I've never seen that, man. Negative. Talk about your journey today. Like, how many of these bags have you created? And I love the fact that each piece of the bag comes from a different part of your story, your adventures, your travel, or, you know, the poetry of the day.

[A]

Yeah.

[B]

Talk about how this is literally your book, your journals.

[A]

So all of my bags, you know, kind of combine my journey starting in Colorado and kind of combining the mountain. Great place to start, you know, Western girl with the, you know, girl gone island. Right on. So I combine leather and raffia, which I guess, typically people don't do that much, so I don't know. But I usually have some sort of wood in there. You know, with my background in my family business, there's usually some sort of wood element, and then there's always some sort of story, whether it's inspired by, you know, the ocean waves.

[B]

Yeah.

[A]

Or just different stitches that remind me of something or a shape, that balance or anything. The inside of the bags have an interior. They have a nautical map that is of the Virgin Islands. And I did that on purpose, basically, as a reminder for people to kind of look within. Right. And take note of the course you're on and have the confidence and courage to change that course if you're not on the one you want.

[B]

Right on. I was just going to say, for someone that's been doing. Seeing numbers for 30 years, and I'm sure you recognize patterns, do you think mathematically the chances of what's happened to you and are possible? What's. What's the math on that? Like, that pivot? Like, is it just. Were you mathematically proven to do this? Like.

[A]

I don't know. I mean, after 30 years.

[B]

Oh, I was gonna say, do the numbers tell?

[A]

I. You know, I. I've always loved numbers and grew up a numbers girl. But I also. When I went to grad school, I learned that I had a creative, you know, imaginary piece that I think I just squashed.

[B]

Right, right.

[A]

But it was just been dormant. It's been buried, and so it's time to let it out.

[B]

But you're the person that literally created pixel art using Excel. So you use your nerdy side to create art. Talk about that journey and kind of showing, you know, turning that into that physical object and kind of giggling at yourself.

[A]

I don't even think I had any, like, a drawing book.

[B]

Yeah.

[A]

You're just like, I was just, you know, doing what I do, and then it just evolved into different stuff. I mean, and I. I always get ideas when I'm snorkeling. That's how I. I love it. The mermaid part. It's the mermaid. That's where I find my ideas. And it's where I do my best thinking and then I, you know, I'm

[B]

curious to see what your antagonist looks like. So you're clearly in your protagonist form. What does your antagonist look like? If you're on an angry day, what would your purses look like? What do you think? Like just triangles and red and.

[A]

I don't know. I don't want to know.

[B]

I was just gonna say I don't think you want to know. Huh.

[A]

I don't want to know that girl.

[B]

Of course I would ask. Is it just like a bowling ball with spikes? Yeah.

[A]

I'm not sure.

[B]

Well, how can folks find you today and and, and buy a piece of art?

[A]

So you can find us on olakalabags.com where our social is at Olakalabags. And basically we are in some. We're on a high end jewelry store on St. John and then some other high end boutiques around the country and hotels is where we're at right now.

[B]

But yeah, for folks that are watching this literally in your store at the moment, can you tell them what to buy? Say, look over there. Look at that handbag.

[A]

Well, so most bags are.

[B]

Hi, customers. This is a kiosk video.

[A]

You don't. So Olakala bags are handmade in Spain.

[B]

Beautiful.

[A]

And so they are not mass produced in China and you know, other places. And so they are more of a work of art.

[B]

Yeah. So you're seeking out patronage like you're seeking out folks that understand.

[A]

Yeah, I mean, people who have an affinity to quality and craftsmanship and kind of that hands on approach.

[B]

We mentioned that in the interview where it was like the respect for the production pipeline, where it's like this handle was found here. I was feeling this when I did that. There's a story behind every bag.

[A]

There's a story behind every bag. And I hand pick everything that goes in them. My competition is really, there aren't a lot of companies in the United States who have handbags made in Spain and they're all European companies and they don't sell in the US you know.

[B]

Well, there you go. Literally a blue ocean strategy. See what I did there? I connected the debts. All right, my love, thank you so much. Let's close off with why do you what does it mean to be a woman in power?

[A]

To be a woman in power is to inspire women to really just realize that it's never too late to start over at any age. And there's really nothing you can't do. You can learn anything. Especially today. It's all about who you know, and. And whether you are willing to put the work and the time into figuring it out. It's a marathon, not a sprint, so.

[B]

Right on. Or sometimes a triathlon, really.

[A]

Right. Yeah.

[B]

Well, I guess I will run into you next time I'm out snorkeling.

[A]

Thank you for. Down to the Virgin Islands.

[B]

Right on.

[A]

Thank you for.

[B]

Right on. Thank you for the invite. Yeah. Thank you so much for your time and energy. I hope you had a lovely time. We're about to wrap up your sess. And. Yeah. That concludes another episode of the Living youg Legacy podcast, the Women in Power edition. For Inside Success, I am Regal Tierras.