This Former Microsoft Consultant Started a Side Hustle After a Frustrating Vacation Experience — It Hit $250,000 Fast and Makes Millions Now When Nicole Smith met up with her best friend in Paris and struggled to get good photos of them together, she knew there had to be a better way.
By Amanda Breen Edited by Jessica Thomas
Key Takeaways
- More than one-third of U.S. adults have side hustles, averaging $891 a month, per Bankrate research.
- See how Nicole Smith turned a common travel frustration into a business opportunity and global brand.
It's the era of the side hustle, and if you've ever considered starting one to earn some extra cash outside of your 9-5, you're in good company. These days, more than one-third of U.S. adults have side hustles, and their supplemental gigs make an average of $891 a month, according to recent research from Bankrate. Of course, the most successful side hustlers see much higher earnings, especially when they start a business that brings in nearly as much as — or significantly more than — their full-time sources of income.
Image Credit: Courtesy of Flytographer. Nicole Smith.
Nicole Smith, 52, of Vancouver Island, Canada, is one of them. Smith was a marketing consultant for Microsoft when she started Flytographer, a global marketplace that connects travelers with local photographers in 350 cities worldwide, as a side hustle.
Want to read more stories like this? Subscribe to Money Makers, our free newsletter packed with creative side hustle ideas and successful strategies. Sign up here.
When did you start your side hustle, and where did you find the inspiration for it?
It was October 2011, and by some miracle, I was chosen to go to Paris for a work project. My best friend, Erika, flew down from Copenhagen to meet up with me for the weekend. We were having a marvelous time, strolling the cobblestones in Le Marais, savoring our coffees, laughing and catching up as we soaked up Paris together. Living on two separate continents means Erika and I don't see each other very often, and I didn't want to forget this precious day, ever. I wanted to capture this moment, this story of our perfect day together in Paris. Try as we might, we just couldn't get a decent selfie or stranger-taken photo to save our lives. I mean, we've all been there, right? The results displayed seven chins, heads cut off, weird angles, bad lighting, and it can be embarrassing to ask the kind stranger to re-take the photo.
Luckily, on that foggy October day in Paris, we had brunch with a local ex-pat friend of Erika's named Anita. Afterward, I passed her my iPhone and asked if she would snap a few shots from a wide-angled distance as Erika and I walked through the pretty streets. All I wanted was one decent photo of us with the gorgeous Parisian architecture in the backdrop so I would be able to relive the memory when I was back in Canada, far away from this moment. Twenty minutes later, when I got my phone back, I scrolled through the camera roll and shivered with goosebumps. It was there. Anita captured our story. The spirit of the trip. The beauty of Paris. In a photo. This led to me creating the world's first global vacation photographer platform in 2013.
What were some of the first steps you took to get your side hustle off the ground?
To test the concept, I would interview and recruit photographers in destinations where good friends were traveling. I would explain the concept, give the photographer instructions and then get feedback from both my friends and the photographers. I did this in multiple cities, learned more each time and continued to refine the process until I felt confident enough to build the website and launch.
Are there any free or paid resources that have been especially helpful for you in starting and running this business?
When you start a business, you have to quickly figure out accounting, legal, software systems, marketing, customer service, human resources and so on. It's exhausting but so important. I basically have a PhD in Googling (and a master's in YouTubing) now. Twitter is also a great place to learn from experts in your space. You can learn so much online; there's never an excuse for not knowing. As a CEO, your job description changes every year as your business scales, so it's important you invest in learning new skills for every stage. I've invested in formal programs, courses, books and startup accelerators over the years. One of my favorite resources for mindset growth is The Conscious Leadership Group, and I re-watch their snackable videos a few times a year.
If you could go back in your business journey and change one process or approach, what would it be, and how do you wish you'd done it differently?
Without a doubt, I would've focused on profitable growth from the start. There's a lot of pressure to scale your business aggressively after you raise an angel and then seed round. Knowing what I know now, and especially after the pandemic almost took us out, I would prioritize growing a bit slower but profitably versus growth at all costs in the early years of the business.
When it comes to this specific business, what is something you've found particularly challenging and/or surprising that people who get into this type of work should be prepared for but likely aren't?
People have a lot of feelings about being photographed. It stirs up a lot. We often see customers who have trouble convincing their partners to participate in the photo shoot. Yet they often share afterward that they had "so much fun chatting with the local photographer in Rome or Tokyo. And the beautiful memories that they captured become more priceless as years go by."
Can you recall a specific instance when something went very wrong — how did you fix it?
In the early scrappy days of the company, we paid all our photographers manually, one by one, using PayPal. Hundreds of micropayments every single week all around the world. It worked fine until the day PayPal unexpectedly shut us off without warning or a reason. Suddenly, I had no way to pay my community of photographers.
I had to move quickly in three areas. First, reach out to everyone who had any connection at PayPal to help us figure out what the blocker or issue was and try to resolve it. Second, write to our community of photographers, letting them know the situation and that we're working on a resolution and to trust us and hang in there while we work to solve it. Third, look for alternate payment processors that would allow us to scale for the future. We were not able to pay our photographers for four weeks while we integrated our new payment processing system with our backend. Because we had built up so much goodwill with our community over the years, they trusted us and knew we would get it resolved as soon as possible. It was incredibly stressful, but in the end, our team rallied and resolved it with an even better solution for the future.
How long did it take you to see consistent monthly revenue? What does growth and revenue look like now?
Two years! I raised an angel round and was able to invest in a small team and growth in 2015. The first year we made $30,000, the second year $250,000, then we started to scale into the millions. We are crossing eight figures in revenue and growing profitably.
What do you enjoy most about running this business?
So many things, but I'd say I truly love our mission of "helping people remember their favorite stories, forever." I love seeing the four-million-plus photographs and stories we have captured for people all over the world across so many destinations and special occasions. It's truly a privilege that our customers trust us to preserve these memories. Secondly, the relationships with the amazing photographers in our community. Some I've known for 12 years and seen them get married, have kids, buy homes — all while doing work they love.
Related: Dog-Lovers' Side Hustle 'Took Off Right Away' and Made More Than $30,000 a Month — Now It's About to Hit $2.3 Million
What is your best piece of specific, actionable business advice?
Identify a problem that you want to solve and just start doing it. Talk to people in that target audience and get feedback from them, and then start building, learning and iterating. There are so many free resources and courses out there, and you can Google so many things… software is cheaper than ever, especially with AI. You don't need a big budget, and you don't need to be an expert in that area. I knew nothing about photography when I started this business. Most things are figure-out-able. You just need to be curious, resilient and a learning machine.
