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Meet Evelyn Rupp of Evelyn Grace in Ventura

Today we’d like to introduce you to Evelyn Rupp.

So, before we jump into specific questions about the business, why don’t you give us some details about you and your story.
I honestly never really anticipated becoming an entrepreneur if I’m being honest. In hindsight, I’m not sure why. Both of my parents and all of my siblings are very entrepreneurial. Maybe it was the rebel in me that wanted to be different. But, regardless, I fully planned to become a politician. (It’s so funny to me to look back on that.) I began to train for politics at 15 years old. Public speaking classes, debate club, legislative camps, law training, leadership organizations… all of it. Through that season, I also picked up a camera and fell in love with the art of photography. I didn’t think it’d turn into anything beyond a fun hobby. Maybe, years down the road, I’d turn it into a side business when I had kids and wanted to step away from the political arena a bit more. But I never saw it turning into what it is today.

But, at age 19, everything just changed. My passion for politics seemed to vanish overnight. I left an internship and a college education opportunity behind and just began to pursue photography. With no degree, formal training, or honestly any clue where I wanted to go, I turned that hobby into a 6 figure worldwide photography business within a little over a year.

From there, things just began to explode. I realized a lot of photographers didn’t have the tools necessary to see that kind of growth in their own businesses, and a passion ignited in my heart to see other business owners thrive. With that passion fueling me, I started The Heart University: a business education company for creative entrepreneurs. With my best friend Lindsey Roman as my business partner, we created in-person workshops for photographers and then expanded into business coaching, podcasts, online courses, resources, and more.

It’s been a wild ride in so many ways, but I wouldn’t change any of it. I honestly think so much of that prior training seriously accelerated my growth. Critical thinking, public speaking, communications, and confidence were all a steep learning curve that gave me such a knee up when I started my business.

Great, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Definitely not. Starting multiple large companies before 22 was a huge learning curve. I had to learn how to manage the finances well, hire a team, communicate with employees, and handle large responsibility and pressure.

A funny story along those lines: I had to hire a full-time payroll employee awhile back. I was having my bookkeeper help me set up most of the payroll, systems, etc… but one day I got a call. It was a worker’s compensation agent asking me all sorts of questions on which policy I wanted. I had NO idea what he was talking about half the time, but I either asked questions or googled terms while he was talking, and by the end of the call couldn’t stop laughing. I called my dad (who’s owned his own business for 35 years) and we cried laughing so hard while I asked, “can you help me make sure I understand workers’ comp?? Is it____??” That agent on the phone probably had no idea I was clueless to half of what he was saying, but I figured it out as I went, hahaha.

I feel like that represents a lot of my journey. I’ve had to figure out most of this stuff by myself and because of that, I’ve messed up MANY times. But that’s been part of the adventure – figuring it out as I go. 😉

Alright – so let’s talk business. Tell us about Evelyn Grace – what should we know?
I actually own several different companies, but I’ll talk to you about my main two at the moment: Evelyn Grace LLC and The Heart University LLC.

Evelyn Grace is my personal company. I specialize in destination wedding and elopement photography, business coaching, and a lifestyle brand. That’s where I got started initially, and I think it’ll always be my baby. I love traveling the world to photograph couples in love, and sharing my life and journey along the way is such a joy. I think what sets my work apart from others is that connection is non-negotiable for me. I don’t shoot weddings and elopements just to earn money or travel to beautiful, exotic places. That’s a perk, don’t get me wrong, but that’s not my goal. My passion is to serve my couples with everything in me and see their life enhanced because I was a part of it in some small way. I work hard to connect with my couples as friends, not as clients. And I truly think that makes all the difference in the moments and emotions I’m able to capture.

The Heart University is my business education company. That’s the business I started with my business partner, Lindsey Roman. We teach entrepreneurs how to start, manage, and scale a wildly successful business with passion, purpose, and legacy. We have thousands of students between our online course, workshops, and free education (podcast, etc.) Lindsey and I are both so passionate about seeing small business owners given the tools to thrive, so that’s what we do. I think what sets us apart the most is that we focus on ALL the vital aspects of running a successful business: Strategies and implementation (marketing, branding, logistics, etc.), mindsets, AND artistry (crafting and mastering your product or service, meeting a need, etc.). In order to create successful and sustainable business, you have to focus on ALL of those aspects. You can know all the business strategies in the world, but if your mindsets are out of balance, you can only go so far. On the flip side, your mindsets can be healthy beyond words, but if you don’t understand the strategies… again, you’ll crash and burn sooner or later.

Something we noticed as Lindsey and I were building our businesses was that a lot if not most of the education in the business world was one of the three elements: strategies, mindset, or craft. Nothing is wrong with that necessarily… but we felt really passionate about focusing on ALL of them with excellence. I think that’s one of the top things that sets us apart.

Is there a characteristic or quality that you feel is essential to success?
I’d say boldness. Not even necessarily in personality half as much in mindset and goals. My parents always laugh that from the time I was a baby, I always believed I couldn’t fail. I’d try new things, chase after ideas, and take risks as if I’d never lose. I honestly think that’s a huge reason I’ve grown my companies to where they are today. I never really had a fear of failure holding me back or controlling my decisions. Not to say that I wasn’t sometimes afraid or nervous… but I never let that control me.


  • Photography: Couples adventure session starting at $1,200
  • Photography: Elopements starting at $3,000
  • Photography: Weddings starting at $5,500
  • One-on-One Business Coaching starting at $1,200
  • Online Business Course starting at $2,600

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