Original posted on Medium.

I’ve always wanted to be an entrepreneur. I don’t think I can label myself as one as it feels like I still have so much to learn, but I practice everyday.

1st time entrepreneur

My first real kick at the can was in 2014 when I started a company in Toronto called Flashstock. Prior to starting Flashstock, I was running the product team for a local company building content and analytics solutions for enterprise marketers within large organizations. Through that work, I saw the opportunity to found Flashstock. The biggest pain point of our customers at that time wasn’t content management or analytics, but rather, creating the content they needed for all their ads and digital properties. Most were using traditional creative agencies with full production shoots to create what they needed, regardless of where that content was going. The process was slow and expensive with lots of overhead. Most marketers didn’t have enough content for everything they needed and there was no extra budget to create more. There was also a lot happening in the market at that time; social media was changing how consumers were interacting with brands and forcing them to rethink how they did things. High resolution cameras were becoming cheaper and easier to use and in the pockets of pretty much everyone. I thought if we could connect the brands directly to the photographers, you could probably do it much cheaper and faster — and that’s exactly what Flashstock did.

It was pretty tough going for the first year as we were not really sure of our positioning and the brands who we were targeting didn’t really get it. Instagram was starting to pick up steam after being bought by Facebook and by 2015 every consumer-facing organization on the planet was starting to wake up to it. We had built an amazing founding team by that time (where all the credit for Flashstock’s success needs to go). We changed our positioning from ‘an alternative to stock photos’ to ‘visual storytelling’ and it felt like things really started to work. Most brands now had an Instagram profile and wanted cheap content that was unique to them. Given what we were doing and our price point, this had a very positive impact on our business and in early 2015 we started to grow quickly. We were still growing in 2017, at around 100 people, and hadn’t raised much money — funding the business through customer revenues. We thought it would be prudent to think about raising money. That’s when Shutterstock, the stock photo provider, came in with an unsolicited offer to buy us. Shutterstock had a similar vision to us and since we hadn’t raised much money, it was a great outcome so we decided to go that route and sold the business. I spent a few years with Shutterstock then left at the beginning of 2020.

Demystifying founding stories

One of the things I realized through that experience was how much I enjoyed the early stages of starting and growing a business — seeing a problem in the market and doing something about it. While I was running Flashstock, lots of people would ask me about starting a business and would mention they were interested in doing it themselves, but had yet to take the plunge. They would look at Flashstock in its current state with customers, employees, etc and it would seem like magic and I was the chosen one capable of conjuring up the spirits to make it happen — which of course, couldn’t be further from the truth. They could not see the path we took to get to where we were. When I would tell them the story and the steps taken by the team to get to where we were you could see their wheels turning and faces light up. They could see how all these small steps got us to where we were, and there was nothing overly complex or overwhelming in any of those steps.

After leaving Shutterstock, Jeremy Vo, who I was lucky enough to work with for a number of years at Flashstock and Shutterstock, were chatting about this. We both saw how helpful it was to hear founding stories. Listening to the people in the trenches — the doers — tell their story, hearing all their doubts, the tradeoffs, their first steps, the lumps they took, the lessons learned, etc was hugely inspiring, motivating and made us feel like anything was possible. We wanted to hear more of them. The challenge was they were just really hard to find. Most of what you read was ‘all up and to the right’ and positive positive positive… ‘we had a vision, we launched a product and now we’ve changed the world.’ It was not giving us the creative, inspirational or practical jolt we were looking for. So, we figured that if we couldn’t find this content, we would create it ourselves.

New passion project

We kicked off a side project where we would interview a series of people who started businesses, get their story, and share it with the community to see if we could inspire a few people to take the plunge and learn a few things ourselves. The experience was phenomenal. We met a ton of people who were eager to share their incredible stories. We learned a ton and enjoyed it so much we’re going to keep doing it!

Here’s a link to the first one. We interviewed 25 B2B SaaS founders focusing on where the idea came from, what steps they took and the challenges they faced along the way.

We hope you enjoy it and find it valuable! If you do, please share it with anyone else that may be interested. Thanks for reading :)