Nicole Smith talks trusting intuition and knowing when to take a leap of faith

Nicole Smith is the founder and CEO of Flytographer, a platform that connects its customers to an international network of hand-picked, local photographers – making it easy to capture memorable moments from anywhere in the world. Nine years into business, Flytographer has provided thousands with invaluable photos and stories to share, but what’s now a global name grew out of a simple love for travel.  

Nicole studied international business in post-secondary, but when she graduated she wasn’t ready to get a nine-to-five job. So she packed up and traveled for almost two years, from teaching English in Mexico and South Korea to traveling Asia, Nicole found her passion in learning languages and seeing the world. 

When she felt like it was time to start settling down somewhere, she took a job at Microsoft and ended up working there for almost 13 years on their global marketing team. And she loved it – it combined her two passions, marketing and international travel. But on a trip to Paris with her best friend in 2011, Nicole wanted to bring home one good photo that captured their adventure and showcased the beauty of the city – the idea for Flytographer was born.

“There’s a book by Elizabeth Gilbert called Big Magic, and it describes these ideas that grab onto you. They knock a few times but if you don’t pay attention they go and find someone else.”

Nicole couldn’t stop thinking about her idea for Flytographer, but she was a mom with a stable job at Microsoft, and entrepreneurship is infamous for being hugely time-consuming and very uncertain. But the thought wouldn’t go away. And so, after nine months, Nicole started testing her concept then officially launched Flytographer in March 2013.

Over the last nine years, Flytographer has scaled across six continents, hired 600+ photographers globally, and captured 4 million memories. But that success is the result of years of dedication, long days, and facing challenges head-on. 

Flytographer started as a side hustle while Nicole continued to work full time at her corporate job and raise two young kids. She would work at Microsoft during the day and then focus on Flytographer at night. After a year, that lifestyle became overwhelming and she began to realize that splitting her focus and energy was holding her back.

“You can’t burn the candle at both ends forever, eventually you have to make a decision.”

Nicole chose Flytographer and stepped away from Microsoft. By that point, she had enough data to know she had a product-market fit and that it was time to go all-in to see what she could accomplish. Financially, the decision felt risky – Nicole launched Flytographer when she was 40, she had a mortgage to pay and kids to look after – but she believed in the business, and even sold her car to keep going. 

“I think it’s hard for entrepreneurs sometimes to know, how far should I push this? How far should I go? And to that I say, you’ve got to trust your intuition. 

I would also think to myself, what would 85-year-old me say if I never attempted Flytographer: would I feel more regret about having to restart financially or about never even trying. I knew it was the latter.”

A big challenge Nicole and many other entrepreneurs face is the uncertainty they feel starting a new company. A lot of founders, unless it’s their third or fourth time building a business, have no idea what they’re doing, but are figuring it out as they go along.

Backing up your intuition with data can make you feel more secure. Nicole trusted her instincts with Flytographer but she also spent a lot of time gathering feedback from both customers and photographers. Her advice: focus on the problem you’re solving. Are customers willing to pay for your solution and do they really love it? Asking those questions will help you determine whether your idea has a pulse.  

“You don’t necessarily have a roadmap, in my case, I was building something that didn’t exist yet. But you just have to get comfortable with being uncomfortable.”

Timing can play a huge role in the success of an entrepreneurial idea – Flytographer grew exponentially as Instagram gained popularity. Suddenly, travel photos were seen by thousands of people versus being shared on a slideshow in the family living room.

Initially, some people didn't understand the value of Flytographer, they dismissed hiring a professional photographer on vacation as "an act of vanity" (often older men, Nicole recalls). But the target audience understood the priceless value of a beautiful photo. Plus, the platform facilitates meaningful interactions between travelers and locals. Photographers might share where they get the best cappuccino every morning or a secret viewpoint for a landmark.

Nicole chased her passions of travel and international connection, and in doing so, created a wildly successful platform that has grown beyond just a business –  it’s a global community of memorable relationships.

“For myself and my team, it’s a joy to work on something where you can actually see the impact you're having on the world.”

Q&A Corner

Q: What do you enjoy most about being a leader?

A: I love creating a vision and something that has a positive impact on the world – and then inspiring others to follow along. At Flytographer, our team helps people celebrate their stories through beautiful photography and capture memories that really matter whether it's a surprise proposal, capturing that big moment, or a reunion for family members that haven't seen each other in years. We are capturing milestone moments in people's lives. Being able to build this from an idea in my brain into a global platform where we employ 600 photographers around the world, all capturing memories that will be heirlooms for life – that's what I love. 

Q: What's the best piece of professional advice you've received so far?

A: I'd say the best advice I got was from people that were doing what I was doing but were a little bit ahead of me. There's so much advice you receive when you’re a founder, but make sure you filter it accordingly. You’ll sometimes get feedback from others that is distracting or contradictory. While well-intentioned, they may not have relevant experience in your space or may have only thought about your business for two minutes – while you’re thinking about it 24/7. Filter and go with your gut.

The feedback I got consistently (but took me way too long to learn) was to build your culture on a shared set of values. Create your company values early, really early, and then hire/reward people around those values. I think this is one of the most important things when you're building a team, that you're all aligned in terms of how you see the world, and your “why” as a company. Because when you don't do that, it causes so much internal chaos. And it's really hard to let people go or have to rebuild when you make hiring mistakes.

Q: Do you attribute your success, thus far, to hard work or luck?

A: I think in the early days there was a lot of hard work. When you're trying to get liftoff with a company, you've got to put in the time and you don't have the resources to outsource – I didn't raise money in the first few years. So you're just grinding, grinding, grinding, and wearing all the hats – the good thing is you get to know all the roles and you know who to hire. 

But I also think that you can work your hardest and not get anywhere unless there is a little bit of luck. And so for me, I think the luck was around the timing. For a lot of startups, they have a great idea but it's not the right time for it. Flytographer started when the world was suddenly getting on Instagram, like 10 years ago, and visual storytelling was becoming more and more of a thing. 

Q: How do you find work-life balance?

A: I think for me, I like the word “integration” better. Especially now that we're a remote team, work-life integration is so much easier. I'm able to ebb and flow throughout the day between work and life. It’s about building my rhythm for the week. I just live and die by my calendar, so I put everything in there from my kid's basketball games to all my meetings and my to-dos. If one week I’m working on an HR plan or some other project, I’ll book time in my calendar to work on it. So I find work-life balance by managing my calendar and not feeling like between nine and five it's just work. 

Q: What's something you do to boost your productivity?

A: I have a couple things that I do to help boost my productivity. Number one, I only take meetings on Tuesdays and Thursdays. That allows me to do deep work on the other days. Number two, I’m a heavy user of the Notes app. I don't think that's, you know, anything mind-blowing, but I use it all the time. And I'm really specific about the way I take notes in there. I break it down from work to personal and edit it every single day. It's always just right there at my fingertips. And number three, our team uses Notion for documentation and staying organized as a team.

Q: What's a book or podcast you'd recommend to a colleague?

A: I listen to a wide variety of podcasts depending on the speaker, but I always listen to “How I Built This” by NPR. I think a lot of people know that one, but that’s one I just absolutely love. And then when I go on walks to decompress, because I do a lot of walks throughout the workweek to clear my head, I listen to “Smartless.” It just cheers me up, makes me laugh, and so I always recommend that one too.

Q: What words of wisdom do you have for an aspiring leader?

A: I had no idea when I started working on a startup how hard it would be, it's just way harder than I ever imagined. And you're not in it for the short-term – I'm going on year nine. And I think it's quite common for people to be doing this for 5,10, 15 years. So, know that it's a marathon and that there's going to be lots of peaks and valleys. And in order to survive the valleys or the pits, you need to feel gratitude and cherish the peaks. You've got to love what you're doing and love what you're building and have a clear “why” or mission that makes it all worthwhile. Because otherwise those dark times and those challenging times can feel insurmountable. Consider a daily gratitude practice and make time to regularly celebrate just how far you’ve come!