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Nicole Smith knew she had a great idea for a business. What if she could link vacationers with professional photographers to document their trips?

She left a steady job at Microsoft and worked hard, even running through her life savings and selling her car. Today she is the founder and chief executive officer of Flytographer Enterprises Ltd., which she describes as an Airbnb for vacation photography. “We connect travellers with local photographers in hundreds of cities around the world for short, fun vacation photo shoots.”

Ms. Smith, who has lived in Spain and South Korea and travelled in Europe, runs her company out of Victoria, where she is also raising two sons. She mentors other female entrepreneurs and believes in work-life integration.

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Here she talks about how she made Flytographer into an international business and shares what she has learned about often being the only woman in the room. Ms. Smith was interviewed for I’ll Go First, a new podcast series about entrepreneurs produced by The Globe and Mail.

Flytographer founder Nicole Smith says her customers range from millennials to grandparents.

CHAD HIPOLITO/GM

How did you come up with the name Flytographer?

I wanted to create a name that would become a noun or a verb describing the space. Kind of like Rollerblade or Kleenex. I went through a litany of terrible names. I think one of them was Friend Follower.

But Flytographer offered the word “fly,” and you’re usually flying on your vacation, and also “fly on the wall,” because you’re having a photographer capturing those moments. I had this dream five years ago that someday someone would use it in a sentence, “I’m going to book my hotel and my flight and my Flytographer.” We started seeing our customers using it in sentences, and the first time I saw that I literally had goose bumps.

What is the biggest misconception people have about your company?

People think it’s just for millennials, or it’s just for people who are vain. That couldn’t be further from the truth. Our customers range from millennials to grandparents. In fact we recently posted a photo on our Instagram feed of this couple in their 80s. It lit our Instagram page on fire because the way they were standing there, head to head in this loving embrace, was just priceless. Flytographer is for people who prioritize experiences over things, and people for whom memories are the most important thing when they travel.

The camera on a cellphone today can rival that of a DSLR. How do you sell travellers on using your company?

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I would say you could have a Wolf stove and the fanciest pots, but you’re never going to cook the same meal that a professional chef would. It’s kind of the same thing with photography. Secondly, it’s hard to get a good photo of everybody unless you have an incredibly long arm.

Or a selfie stick.

By the way, a fun fact: More people died as a result of selfie sticks in 2015 than shark attacks.

The third thing is that one of the reasons we travel is to see how others live. Our photographers are excited to host you around their city. So as you’re walking the streets with, say, Roberta in Rome, she’s going to tell you about her favourite coffee shop, her favourite restaurant, or that there’s this great street fair for the kids happening on Saturday nearby.

Nicole Smith in her office in Victoria.

CHAD HIPOLITO/GM

How did you pull together photographers from all over the world?

I found my first photographer on Craigslist Paris, of all places. Initially I sourced people from online forums or contacted them directly. Because we had no credibility, and because no one had done this before, it was incredibly hard. When I launched the site I think we had 18 photographers, but then it got easier because we started getting exposure in the press, and some partnerships. Now we’ve had more than 12,000 photographers apply to our website, and we’ve hired about 500.

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Was entrepreneurship something you considered when you were young?

I did not see myself becoming an entrepreneur at all. I didn’t dream big enough, and when I look back it kind of makes me sad. The more that Flytographer grows, I get opportunities to chat with young women, and I really think it’s important that people be able to see it before they begin. I think I just didn’t see it enough as a young woman. That’s probably why I ended up at Microsoft for 12 years.

So you need to see it before you can be it. How do you get involved today?

In Victoria there is a community organization called VIATEC, which represents the tech sector locally. I’m on the board, and I have opportunities to meet with and connect with women. We usually go to all these events where there’s a lot of beer and the gender imbalance is like 80-20 for men-women, and I thought why don’t we create an event that looks a little bit different. So I started Rosé and Real Talk. We had 100 startup women in Victoria come to our inaugural event in the spring. We had copious amounts of rosé and we had five local women in their 20s, 30s and 40s talk about advice they’d give their younger selves.

What was the reaction from your family when you told them you were going to leave a stable job and create something from scratch?

Well, my dad said it was the worst idea ever. If you have a great job at Microsoft, why would you risk that? It all comes from a good place, though – they love you, they’re worried about you. But then later, a year and a half in, when I hadn’t paid myself at all, and it was draining my life savings, and I had to sell my car, he was like, “What are you doing?” But I said, “You know what, Dad, I know this seems crazy, but you gotta trust me. I would literally sell my house next, that’s how passionate I am about this. At the end of the day the worst thing that could happen is it all explodes, but I’ll get another job – I’ve got skills, so I’m going to go for it." And he said, “Okay.”

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Many entrepreneurs have a co-founder who can help shoulder the stress. What do you do?

I’ve realized it’s important to build a network of fellow founders, and I’ve got some people now who I can talk to. But my go-to person is my best friend. She lives in Copenhagen, and we talk over what’s up all the time. It could be 11 at night and I send her a message, and we’ll hop on Skype and talk it out. She’s an amazing sounding board.

Ms. Smith believes in work-life integration.

CHAD HIPOLITO/GM

How do you balance your professional life with your personal life?

Being a mom and being a startup founder are both full-time jobs, and there are days where I feel like I totally crushed it on the mom front and was “eh” on the founder front. And then vice versa the next day. You’re going to have to make trade-offs.

The biggest tip I have is work-life integration. This summer when I had a business trip to Europe I took my kids along and they were able to meet a lot of the photographers that we work with and understand my business on a deeper level, and therefore feel more connected and less competitive with it. The second thing was my 13-year-old actually interned at Flytographer for a week this summer. I can’t even tell you how fun that was. We got dressed for work together, and we went in, and then we’d have lunch together and he sat with our dev team. Over all, try to balance it as best you can and not judge yourself too harshly.

What is your greatest fear?

Not being an awesome mother.

How many hours do you sleep at night?

I’m a big sleeper – like, I’m a niner. It’s one thing I don’t negotiate.

What’s your favourite rosé?

Anything from Provence.

You speak three languages. Did you pick those up during your travels?

When I was in business school I focused on international business and marketing, and I loved learning about different cultures and how different people communicated. When I graduated, the last thing I wanted to do was get a boring 9-to-5 office job where I’d have to wear pantyhose. So I decided to travel. I spent the first six months living in Mexico City and I studied Spanish. Then when I ran out of money I came back home and I realized I wasn’t quite ready to settle in yet. I moved to South Korea and spent a year there teaching English and learning some Korean.

What piece of advice would you give your younger self?

Oh, that’s easy. I would absolutely tell myself to dream bigger. A lot of women especially have this sort of invisible ceiling that they put on themselves. For me that was definitely the case. And so I just want to beat that drum to every young woman that I can. You don’t have to have all the answers, you don’t have to be an expert, but you have to have that passion and that resilience and that steeliness to keep going, because you can really build amazing things.

This interview has been edited and condensed.

About Flytographer Enterprises Ltd.

Headquarters: Victoria

In business since: 2013

Employees: 18

Revenue: About $5-million

Sometimes selfies just aren’t good enough – like when you’re on a bucket-list trip, or in Florence to celebrate a wedding anniversary.

Flytographer gives travellers another capture-the-moment option: the services of a local professional photographer.

Through the company’s online platform, travellers click on their destination and choose from a lineup of photographers. They set a place and time for the photo shoot, pay online and meet their photographer on the scheduled date. A link to an online gallery of pictures is e-mailed to customers within five days of the shoot.

Nicole Smith, Flytographer’s founder and CEO, says she came up with the idea for her startup during a business trip to Paris. Her best friend, whom she hadn’t seen in years, flew in from Copenhagen for the weekend, and Ms. Smith knew she needed to capture the occasion in photos. They had only their smartphones, so they asked another friend to pinch-hit as photographer.

Today the company’s 450 photographers, who span 250 cities around the world, have done more than 20,000 Flytographer photo shoots since the company launched, she says.

Most Flytographer photographers specialize in weddings, says Ms. Smith, who worked previously as a marketing manager for Microsoft Corp. To be part of the Flytographer platform, photographers go through online interviews and critical reviews of their portfolios.

Ms. Smith says Flytographer customers get more than great travel pictures; they also get a chance to connect with professionals who are proud of their city and often act as local ambassadors during the shoot. At the same time, photographers who normally rely only on local gigs get access to global customers.

New podcast gives voice to entrepreneurs

I’ll Go First, a new podcast from The Globe and Mail, takes listeners into the minds of Canadian entrepreneurs in leading-edge fields such as artificial intelligence, cannabis and cryptocurrencies.

What makes these leaders tick, not just professionally but in their private lives?

Episodes are published on Thursdays. Here are recent interviewees:

  • Geordie Rose is co-founder of Sanctuary, which is building realistic robots designed to do what we do – but better.
  • As the CEO of Dot Health, a medical-records-access firm, Huda Idrees is dragging Canadian health care into the technological future.
  • Bruce Linton of Canopy Growth talks about hanging out with Snoop Dogg, being a father and sparking cannabis innovation.
  • Will Richman of GrowthGenius, a B2B company using artificial intelligence, takes boss-employee bonding to the next level.
  • Cole Diamond, CEO of Coinsquare, is a cryptocurrency pioneer giving Canadians a secure place to buy and sell digital currencies.
  • Solon Angel, chief strategy officer at the AI startup Mindbridge Analytics, thrives amid chaos; he even creates it sometimes.

Look for I’ll Go First wherever you find your favourite podcasts (including iTunes, Google Play Music) or on The Globe and Mail website at tgam.ca/illgofirst.

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