We caught up with the brilliant and insightful Lola Oliver a few weeks ago and have shared our conversation below.

Lola, thanks for joining us, excited to have you contributing your stories and insights. The first dollar your business earns is always special and we’d love to hear how your brand made its first dollar of revenue.

The first real dollar I made from photography didn’t come from a friend, or a family member, or even a friend-of-a-friend, and that’s what made it so special.

When I first started out, I wasn’t planning on turning photography into a business. I was just shooting for the blogs I was writing at the time, finding models on Craigslist to build a portfolio and get some creative content. It was a scrappy, passion-driven beginning. But then something shifted.

One of the models I had worked with on a few creative shoots reached out to me (not as a collaborator this time, but as a client). She wanted to book a session with me for she and her husband. She already knew my work, had experienced several shoots with me, and still wanted to pay for my time. That moment felt like a turning point.

Getting paid for that session felt surreal. It was validation, excitement, and a bit of disbelief all wrapped into one. I hadn’t planned on becoming a professional photographer, but after that, everything changed. I started doing shoots for family, then launched Groupon deals, and slowly stepped into the wider world of working with the public.

But that first dollar, that first real client, made it all feel possible.

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For my event business, that first dollar came from a place I already trusted (Groupon) but the feeling was completely new.

I remember setting up that first paid picnic in the park like it was yesterday. I’d seen those styled pop-up picnics trending during COVID, but I never imagined I’d be creating them as part of my own business. Events had always been something I did for fun, styling birthdays, planning little get-togethers, and obsessing over the details. Friends started telling me, “You should do this professionally,” and eventually, I listened.

I listed my first offer on Groupon and waited. When the first booking came through, I was equal parts thrilled and nervous. It was a couple on their honeymoon, and I wanted everything to be perfect. From the cushions to the charcuterie board, I poured myself into every detail. When I saw their faces light up, I knew I had something special.

They were so kind, so grateful, and so full of praise. That one experience gave me a wave of encouragement I didn’t even know I needed. It confirmed that I wasn’t just good at this, I was meant to do it. And from that moment on, I’ve treated every event with the same care and excitement as that very first one.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’m a portrait photographer based on the beautiful island of Oahu, Hawaii, where I specialize in capturing life’s most meaningful moments through relaxed and heartfelt photography sessions.

My journey into photography started out as a creative side project and hobby. Today, through my photography business, I offer portrait sessions for people of all ages, with a special focus on families visiting Oahu on vacation. Many of my clients are here celebrating something special such as a milestone birthday, a vow renewal, a family reunion, or simply the joy of spending time together in paradise. I also photograph high school seniors, professionals needing headshots, surprise proposals, couples on their honeymoons, and more. If it can be done outdoors (or even at your home), I’m there.

What really sets my sessions apart is the experience I create for my clients. I know that being in front of the camera can feel intimidating, especially for people who aren’t used to it. That’s why I focus on creating a comfortable, laid-back environment where my clients can relax and be themselves. I play island music during the sessions, provide thoughtful accessories and touch-up supplies, and take the time to learn about any special accommodations that might make the shoot more enjoyable for everyone involved.

My style is warm, colorful, and full of life. I aim to capture not just how you look, but how the moment feels. And the feedback I get most often is that people feel surprisingly at ease during their shoot. For me, that’s one of the biggest compliments I can receive.

I’m proud of how far I’ve come and grateful for every client who has trusted me with their memories. What I want potential clients to know is this: my goal is to make you feel seen, celebrated, and comfortable, and to provide you with timeless images you’ll treasure forever.

Whether you’re marking a major life moment or just want to remember your trip to Hawaii with your favorite people, I’d be honored to help you tell your story through photos.

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In addition to photography, I also run a creative event business that brings luxury, fun, and unforgettable experiences to life without the luxury price tag. My brand is all about making special moments extra special, whether it’s a romantic proposal, a themed group gathering, or a community event meant to spark connection and joy.

The heart of my business is luxury picnics, and they’ve been a hit with couples and groups alike. For couples, I offer intimate, beautifully styled options like the Royal Romantic Picnic or the Proposal Picnic, complete with elegant decor and thoughtful touches that make the experience feel one-of-a-kind. For larger gatherings, I have a growing menu of themed picnics that range from tropical to whimsical to wildly unexpected, like the Aloha Picnic with vibrant island decor, a Barbie Picnic full of playful pink glam, a Goth Picnic for the darker aesthete, a charming Cottagecore Picnic, a classic Tea Party Picnic, and even a Circus Murder Mystery Picnic for those who like a little intrigue with their hors d’oeuvres.

But my events go beyond picnics. I also offer a Wedding Week Beach Party experience, perfect for destination weddings, that includes beach umbrellas and games. I make house calls too, with setup options like custom canopies, backyard games, and event styling to match any vibe. I’ve also hosted community gatherings such as sip-and-paints, crafting tea parties, speed dating events, and more, all designed to bring people together in a fun, accessible way.

What sets my business apart is my ability to combine creativity with accessibility. Many people want a taste of luxury but don’t want to break the bank to get it. My mission is to offer elevated, imaginative experiences that are also affordable. I truly believe everyone deserves to enjoy the finer things in life, whether it’s a beautifully styled date night or a joyful group celebration.

What I’m most proud of is the creativity I get to pour into every event. From dreaming up new themes to curating the perfect setup, I absolutely love turning a vision into a real-life experience. It’s incredibly rewarding to see clients light up when they arrive at one of my setups and feel like they’re stepping into a moment designed just for them.

Can you share a story from your journey that illustrates your resilience?

One of the most challenging and eye-opening moments in my journey came when I rebranded my photography business in 2023. I was excited for a fresh start and a clearer brand identity, but what I didn’t anticipate was the impact it would have on my visibility. Practically overnight, my bookings slowed, and sales plummeted.

It was discouraging, to say the least. I wasn’t starting completely from scratch, I had experience, a body of work, and satisfied clients. But the rebrand had shifted how I showed up online. Suddenly, the momentum I’d built under my previous brand wasn’t carrying over the way I’d hoped.

Instead of giving up, I took a step back and looked at what had worked for me in the past. I remembered how instrumental client reviews had been in growing my original business. So I got strategic.  I created a system to actively encourage clients to leave feedback after their sessions, this time focusing on Google rather than Yelp, where I had previously concentrated my efforts.

It wasn’t an instant fix, but slowly, things began to turn around. With each new review, my visibility increased, and the bookings started picking up again. That experience taught me that resilience isn’t just about pushing through hard times, it’s about staying flexible, learning from the past, and being willing to pivot when something no longer works.

Looking back, that dip reminded me that success isn’t linear and that sometimes, what feels like a setback is really just a redirection.

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?

One of the biggest lessons I’ve had to unlearn through running my event business is the idea that everything has to be perfect. As someone with a Type A personality, I’ve always held myself to incredibly high standards, often to the point where I’d sacrifice sleep, time, or even my own peace of mind just to add one more little detail to a setup.

But through experience (and a few stressful event days), I’ve learned that done really is better than perfect.

What helped shift my mindset was realizing that my clients don’t see the version of the event that exists in my head. Clients only see the finished experience in front of them. If I run out of time to add a small extra detail, they’ll never know it was missing. They show up, see something beautiful and thoughtfully styled, and they’re thrilled.

A good friend once told me, “What you offer is already more than enough.” That stuck with me. It reminded me that my “good enough” is often someone else’s wow. I still catch myself falling into perfectionist habits, but now, when a client arrives and their face lights up, I take a breath and remind myself: the goal isn’t flawless execution, it’s creating joy. And that, I can do.

Contact Info:

• Website: www.isleofphotos.com | www.isleofevents.com
• Instagram: @isleofphotosoahu | @isleofevents
• Facebook: www.facebook.com/isleofphotos | www.facebook.com/isleofevents

Image Credits
Isle of Photos Isle of Events