Reflections from Flytographer’s Founder on our 8th Birthday

Do you have a side hustle idea or startup idea rolling around in your brain? 💡 Taunting and teasing you, daring you to crack it open and explore it further? 

I was sitting on a bridge in Paris in 2011 in the warm autumn sunshine when the idea for Flytographer first rolled around in my head. 

As we now celebrate our 8th year in business, I took some time to reflect on a few things I’ve learned as I first went from the idea in 2011, to the decision to launch in 2013, to finally building and growing Flytographer. I hope that by sharing my story, it will help those of you about to embark on a similar path of launching something amazing. 🚀

With gratitude,

Nicole Smith, Founder & CEO

The day Flytographer took over my brain - Paris, October 2011

1. There will probably never be a perfect time to start, so just go for it — but take small steps!

What are the stories you tell yourself on why now is NOT the best time to start that side gig or business you’ve been daydreaming about? Not enough money? Time? Experience? Too old/young? Just the wrong time in your life?

I got the idea from Flytographer while on a business trip to Paris, but I felt like I checked all the wrong boxes (and it kept me from taking my idea seriously for a full 9 months). 

  • No experience: I had never built my own startup before. I was not a professional photographer. 
  • No time: I was a single mom with two young kids and a full-time corporate job. 🏃‍♀️
  • No money: 👀 Looks for coins in couch.
  • Too old: Stares down 40 in the mirror. 
  • Wrong timing: My life was finally calm after a hard divorce a few years earlier. Why rock the boat again? 😬

But I remember sitting in my car one day in the summer of 2012, thinking, “What is the worst that could happen if I just tested a few things?” 🤔

Photo from the very first test shoot in Paris - September 2012

So I found a trustworthy photographer on Craigslist in Paris and asked a friend travelling there to try out a test shoot. I’d only be out 200 Euros if he flaked or if my friend hated the experience. It was a calculated risk, a small first step. 👣

Then I took another small step.

And another.

And another.

Pretty soon, I was a bonafide sidepreneur, testing and learning how to develop Flytographer in my non-work, non-parenting spare hours, which were few. 😅 It grew slowly — but it was a start!  

Do you have an idea you can’t shake? Take small, low-risk, micro-steps towards your goal; the hardest part is sometimes just getting started.

2. Knowing when it’s okay to transition from “side hustle” to “going all-in.”

Keeping your 9-5 and being a sidepreneur as you start out reduces your risk and allows you to test, learn, and iterate on your product. It can also eliminate the debilitating financial stress of not having a steady income. Couch surfing and living on ramen 🍜 is just not an option for many of us, especially as a parent.

But when do you make the big move from sidepreneur to going full force? It may be never 🤷‍♀️ — maybe the side gig is the best path for you. However, if your dream is to work full-time on your business, a good barometer is when you nail “product market fit.” It’s when your customers truly love what you have built 💖, come back for more, and tell all their friends. The positive feedback of our early Flytographer customers and photographers is what gave me the confidence to “go all-in” and quit my corporate job one year into starting Flytographer.

Michelle, our Creative Director, and me in front of a projection of our logo in our first real office space - February 2015

The other test I gave myself was to imagine how 80-year-old me would feel if I never took this risk.

Would wondering “what if” be worse than any potential failure or loss? What’s the worst-case scenario? Embarrassment? Financial loss? I could always go back to work and get another job. But abandoning it and then wondering “what if I had given that crazy idea I had at 39 a shot” might have haunted me more.

Lastly, trust your gut. It always knows. 💪

3. Most of us are just figuring it out as we go.

There is a lot of “winging it” when you are an entrepreneur. They often say you are building the plane in the air as you fly. It really does feel like that a lot, even years later. You can plan and prepare like a Navy Seal, but you will still make mistakes, mess up, and bad things will happen that are out of your control. 

I vividly remember when PayPal arbitrarily shut us down in 2017 with no notice and just froze our funds. 😱 We suddenly had no way to pay our global roster of Flytographers and had to scramble to figure out a better system. I remember writing to our community of photographers to tell them the bad news, terrified they would all abandon us (side note: they didn’t, they are all rockstars 🌟). 

After a couple of weeks with zero progress with PayPal, our whole team worked overtime to roll out a new payments platform globally. It ended up being over a month of stress, fear and “omg, my business is over” panic attacks. 

But … the scar tissue that builds up makes you stronger and more confident that you can surf the wild waves still to come. Because guess what — they will keep coming! Perfect case in point: 2020. 🌊  (Read more on how we surfed the pandemic tsunami here.)   

Expect the hiccups — it’s just the cost of doing business. And as you navigate through, remember the saying “this too shall pass.”  Simply focus on what you can vs. can’t control, and keep on building based on the lessons you’ve learned. 😎 And just figure it out as you go.

4. It’s easy to put yourself last. Spoiler: this is a terrible idea.

The firehose of work never stops. It never stops. If you love your business, it can be hard not to think about it 24/7 — for me, it’s like my third child. 🧒 If you are a parent (or a single parent like me) or caregiver to a family member, there are many of things competing for your time and it’s very easy to dismiss your own needs while juggling the balls of taking care of others, your business and household chores.

Remember that without a strong mental and physical foundation, the world of YOU can break down, and that has a lot of cascading effects. Repeat after me: it’s not selfish to invest in things that make you feel your best. It’s imperative. 💓

Things that have been working for me lately (but it’s still a constant struggle to manage, tbh):

  • Time blocking my days in my calendar 📆 (work, workouts, family/friends things, and most importantly, ME TIME all go in there).
  • Preserving Mondays, Wednesdays and Fridays for deep work — no meetings! 
  • My hype crew.  🎉 It’s key to connect with friends who are building similar stage businesses and can relate to your journey, share insights and cheer you on in the highs and sit with you in the lows. 
  • Regular counselling sessions, not just when I have a big issue. Consistent mental hygiene is one of the best investments I’ve made in myself.
  • Morning walks by the ocean with my favourite music or podcast. 🚶‍♀️(I’m very lucky to live on an island!)

5. ABL: Always Be Learning!

I cannot emphasize it enough: always be learning. 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 (and a Masters in YouTubing) now. Twitter is also a great place to learn from experts in your space.

You can learn soooo much online, there’s never an excuse for not knowing.

I also invested in a few formal programs and courses over the years. 📚 Two that I found super valuable are: Shine Bootcamp (public speaking) and GrowClass (growth marketing). I also joined a few startup programs and accelerators (Lazaridis, The Forum, Viatec, C100) to grow my community of startup founders and access resources, mentors and support. Everything I learned helped so much.

6. Surround yourself with good people. 

As you begin to hire your first employees, make sure you hire based on shared values — not the resume. One TedTalk I recommend is this one by Adam Grant. I love how he frames the importance of hiring givers and matchers. 

When your startup is small and trying to get lift-off, you need people who are brilliant at wearing multiple hats and comfortable navigating a lot of ambiguity, have a bias towards action, are curious and take initiative. Things are moving so fast — remember, you are ALL building the plane together in the air at this stage. 🛫

As your business scales, inevitably some employees will move on to other jobs and opportunities. I have a favourite story with Caitlin. Caitlin joined our customer experience team in 2016, left in 2018 to try something new, travelled a bit and went back to school to become a developer — and then happily rejoined Flytographer in January 2020. It’s a real highlight to see team members develop and thrive over the years, and especially gratifying when they return to the family. 🐣

This is just one story, but we have an amazing team of 10 women at Flytographer who not only kick ass at their jobs but are caring, kind, inclusive and so much fun to work with every day. 👯‍♀️

Caitlin holds one of her favourite Flytographer photos in the office - January 2016

We extend this philosophy of hiring for shared values to our photographer community as well. 📷 Mentally answering the question “Would you want to spend one precious hour of your vacation with this photographer” is one of our vetting criteria when we interview — they have to really love people and their city in order to join our roster.

Our photographers are like family; many have been with us since the very early days, and over the years we’ve seen them get married, have babies and buy their first homes. Having true friends around the world is truly one of the biggest blessings of my job. 🌍

7. It’s important to define your own version of success.

You may not know exactly what success looks like to you in your first years, but don’t worry, you will in time.

I was often told that growing a huge business should be the North Star — the definition of success. You hear VCs talk about targeting $100M in sales all the time. 💰 Growth at all costs. 

A lot of us have reexamined what makes us happy in the last year and what success means. For me, it’s simple and mostly comes down to this: having control over how I spend my time.

A few other things that define success for me:

  • Mainly working from home (hello fellow introverts!) 👋
  • A small team of really good humans where I can really know everyone 
  • Bringing a product to life that customers really, really love 💖
  • Running a profitable business that may grow a bit more slowly, but has a happy, thriving team and community of photographers who feel valued
  • Not compromising my values and having control over our vision for the future 🕹️

Success is picking my kids up from school as often as I want — and being able to bake them fresh muffins between calls.

Success is starting my mornings with either a walk along the ocean or a having workout (and laugh) with my girlfriends. 🏋️

Success is rarely travelling for work — unless it’s to one of our legendary Flytographer Global Meetups!  ✈️ 

Success is different for everyone, and it will look different for you at different stages in your life. But what’s important is for YOU to define your terms — no one else.

8. Life is unpredictable, so spend as much time as you can with the people you care about.

If 2020 taught us anything, it’s that life can change in a blink of an eye. Not being able to hug my parents for months on end or to visit my best friend in another city or to explore new places with my kids was hard. It was a huge wake-up call to stop taking life so seriously and to make sure you are having more fun with the people you love as often as you possibly can. 🎊

Finding snippets of micro-joy every day and spending time making memories with the people you love is more important than ever. Tell the people that matter how you feel about them ❤️ and tell them frequently. When you look back on the times of your life, those are the moments you’ll cherish the most. 

And that’s it, the 8 lessons that I wanted to share, earned through a lot of trial and error, tears and joy. I am now off to share some celebratory birthday cake with the team 🎂 … and to tell future 80-year-old me, “Don’t worry, we don’t have to wonder ‘what if’ anymore.”

We are celebrating a pandemic birthday, after all! 😜

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