Nicole didn’t intend to be an entrepreneur. She was working day and night and took a break in Paris with her best friend of three years. They were on the cobblestones with no husbands, no kids, and wanting to take a photo because “this will never happen again.”

They did what everybody does. They took selfies, but the photos weren’t perfect to represent this magical moment. So they connected with a local friend of hers. She gave the friend her iPhone and said: “can you take some candid shots of us from a distance?”

She didn’t want a posing and cheesy photo in front of the Eiffel Tower. She wanted something that captured the spirit of the moment like walking down the cobblestones, drinking coffee.

Twenty minutes later, when she looked at her phone, she had goosebumps. The photographer had captured the spirit of her trip. It was the best souvenir. In this small moment, the idea for Flytographer was born.

When did you realize you could turn your idea into a business?

The first step in starting a company is finding an idea that won’t go away. Nicole had that idea. She just needed the courage to take the jump. That would start with one small test to prove out her idea.

“I thought ‘When I travel again, how do I do this?’ I went back to Canada after that trip to my job at Microsoft and could not stop thinking about this idea. I would think about it 20 times a day. But the thought of jumping into a startup was overwhelming. Still, the idea wouldn’t go away for nine months.

I realized I had to do something about this because I couldn’t get this idea out of my head. I’d regret it the for the rest of my life if I didn’t do something. So I was turning forty in September and I gave myself that artificial deadline.

The next step is I went on Craigslist Photographers and found one who seemed legit. I had a friend traveling to Paris and I said, ‘Hey, do you mind if I have photographer hang out with you for half an hour to take candid photos?’

‘Sure no problem.’

That was the first test.

Were there any obstacles when founding your company?

When Nicole stepped into entrepreneurship, there wasn’t a roadmap. She’d have to invent it along the way. To help, she kept her job which gave her time to prepare before she made the jump.

“One of the pieces that is important in our team values is what we call candor. It’s important to be honest and direct. If you don’t get straight to the point, then all the passive-aggressive craziness can distract everybody.

You socialize with people whether it’s your friends, your family, and co-workers. So you get a lot of mixed feedback like ‘yeah, that’s a great idea.’

Then there are people who think you’re crazy.

‘Why would you quit your safe, awesome job for something risky?’

The first struggle was just clearing all that conversation clutter to go with my gut. The second thing was I didn’t know what I was doing. I’m not a photographer. I don’t know a lot about photography either. I didn’t know how to build a website. I didn’t know how to do accounting. There are so many things that I needed to figure out.

It’s hard because you’re trying to figure out everything while you’re working full-time.”

How did you start getting traction for Flytographer?

Sometimes it takes pure hustle to get that first green light. For Nicole, that meant participating on relevant blogs for months. She did that until it earned her the credibility and traffic to turn her corporate office dream into a reality.

“For early marketing, I spent two hours a day dropping comments on relevant blog posts. Then one of my comments was read by a writer at NBC.

She wanted to interview me. The next day, I’m on the homepage of NBC. It was funny because I’m right next to the photos and articles of Prince Harry and Angelina Jolie.

This was only two months into my business.

That gave me a huge boost in confidence which led to social proof and photographers applying.

The problem – the business is seasonal. It was only after six months, did I start seeing customers come back and hearing from them either personally or through referrals.

‘Hey, I heard about it from my friend in Paris last month.’

At that moment, I had the sense that I had picked the right market.

The third thing was feedback from testimonial forms. That was something that I engineered from the start. Just the words they were saying – that’s when I knew we had product-market fit because people were overjoyed with the value that they got from the service.”

How did you build out your team?

For early-stage startups, you have many problems that need to be solved. Nicole realized this and it meant she needed people who could come in and wear multiple hats with an execution mindset.

“I am marketing and product person. Those are the areas that I am passionate about. I don’t have the technical chops. I knew I needed to bring on a director of engineering to drive the technical side.

I also don’t have the financial chops. I needed someone to help in that capacity. Those are the two key parts. We just started bringing on marketing talent because we realized that we want to scale the business.

I know I’m the product manager that drives the roadmap, but I need to step back and allow other people to drive forward marketing.

The biggest thing about hiring people is finding people who are doers and problem solvers. You don’t have a roadmap on how this works and how their role works. It drives me crazy when someone doesn’t have that as part of their DNA.

That’s why our first five hires were people who could wear many hats. Now that we’re 20 people, we’re focused on getting those seasoned experts on board.

One of the pieces that is most important in our team values is what we call candor. It’s important to be honest and direct. If you don’t get straight to the point, then all the passive-aggressive craziness can distract everybody.

I’m a big fan of being direct.

Everyone’s got each other’s back, but we need to get through the hard conversations.

When building out the team, the hardest step was the first year and a half of my business. I didn’t have a team. I had no developers. The business was on Squarespace. The site was hooked up to a CRM database and some webhooks.

I was this wizard behind the curtain. It helped me understand exactly what I needed to develop in order to service the market. Then I hired a developer and the business took off.”

What marketing strategies worked best?

For Nicole’s business, she found that the idea of finding one growth hack to build your business on wasn’t a realistic expectation. She needed to put in the time and sweat equity with the right mindset.

“There’s no a silver bullet. What I realized is that constant steady growth is testing different channels to see what works. For us, the biggest source of traffic has been organic search. We’ve had a lot of focus on content generation from the start and SEO optimizing content keywords and communicating with the right partners so that we get a lot of deep links to our content.

30% of our business comes every month through organic search. One of the things that a lot of companies don’t do is invest in content marketing early on because they’re short-sighted.

Evergreen content is a low-cost acquisition channel. You’re not interrupting people. They’re coming to you because you’re being helpful. We started creating content early on, making sure all the keywords were in there, and that our content connected to each other.

We’d ask these questions:

‘Do these rank well?’

‘How do we get links to these different content partners?’

Then constantly serve them up.

We have more than a million beautiful photos all over the world of travelers.

There’s nobody else that has anything close to what we have.

We’re across every continent, age, and race. It’s real people with their stories attached to it. Attaching that content to our customer has been a huge part of our growth strategy.

Our North Star metric is the number of shots per day. Every morning we look at traffic, repeat customers, but at the top of the pile is average shoots a month.”

Did you hit any inflection points in your business?

Even if your business has traction, it doesn’t mean it will survive. There are many thousands of problems that can arise. They almost always do when you least expect them. Great founders persevere through these moments.

“We had challenges with people because we were paying photographers via Paypal initially. Then at one point, PayPal shut our account down. We got flagged because we needed the birthday for the customers. It was a weird situation.

I wasn’t going to give them the birthday of our customers. Luckily, I built up enough trust with the photographers over prior years that it gave us time to find another payment provider. It took us three and a half weeks.

I thought this would end my business if I couldn’t figure it out.

I couldn’t contact a customer from a month ago and say,

Hey, I need your birthday.’

I was transparent with my community and said,

‘Hey guys, this is happening. It means you don’t get paid until we figure this out and I hope you’re with me.’

What’s your advice for entrepreneurs just getting started?

Nicole has some real, down-to-earth advice. There’s no sugarcoating here.

“No one knows exactly what they’re doing. Just try to test things, have conversations with your potential target audience, and start to understand the problem that you can solve for them.

The third thing is only doing it if you really love what you’re building because if you don’t really love what you’re building, then there are so many highs and lows of entrepreneurial journey that you won’t make. It’s hard. And I’ve had kids – that’s really hard. This is harder.”

What’s your favorite part about your business?

At the base of any great business is a community. Without community, there’s no momentum, true fans, or people who will have your back when your business takes a bad turn. That’s why Nicole made a community the centerpiece of her business.

Flytographer supports artists around the world. In December, we saw the top 25% of our photographers make over $1,500 a month shooting a couple times a week. Because of our service, they can pay their mortgage and live a better life.

It’s repeatable business for them, too. The community is big, so we’ve been investing in that from the start. We have annual meetups once a year, everyone flies in and hangs out for a week in Paris. We spend time together doing workshops, lecturers, photo ops, and drinking.

During these events, we get a lot of product feedback. It’s also incredible to foster these friendships in person. It’s created this place where we have a friend in every city all around the world. 

Today, we’re working with over 450 photographers. Fun fact, we’ve had over 10,000 apply. We only hire a photographer with a great portfolio and a fantastic personality.

Where’s the next take-off point?

As a bootstrapped entrepreneur, Nicole has put in the years of effort required to build something great from scratch. She’s put herself through countless learnings all because she found a problem worth solving.

She noted that they are trying a couple of innovative next steps to grow their business (soon-to-be-released). To help, she is hiring more of the right people for her team.

Keep in mind, the Flytographer team is still in their early stages.

You could say they haven’t even left the airport in terms of potential.

Stay tuned to see where they fly next.

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