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Thrilled to announce we've raised $15M to continue our mission of protecting businesses by backing up their cloud data. Here's a quick thread on how I’ve helped build Canada’s latest “overnight success” over the past 10 years… https://betakit.com/ottawa-cloud-backup-startup-rewind-raises-19-million-cad-series-a/
Starts with my first startup - AddIn Social. I left a great job at Adobe to start that startup in late 2010. That's when I first meet @mattroberts, but AddIn Social never had any substantial revenue or got any traction. https://www.crunchbase.com/organization/arkli
That startup nearly ruined my life. I had to spend 3 months in Toronto while my wife was 4 - 7 months pregnant with two kids under 4 at home. I almost lost my family - nearly got divorced. I promised my wife I would never do that again.
After that failed experiment, I picked myself up and got a job at @Ackroo where I met @seashellski.
Unfortunately for my wife, I’m an entrepreneur at heart. So the promise I made only lasted a couple of years. I wanted to try again, and contacted @seashellski to start working on something. We launched our first product, http://edits.io in late 2014.
6 months in, we had no customers. No one was using it and we had no way to go to market. I recognized that we weren’t getting anywhere. It looked just like my first startup - so I knew what failure looked like. We needed a pivot or new idea.
So, with 2 failures under my belt, I suggest we work on backups for @Shopify. I knew backups were needed, Shopify was growing quickly, and I wanted to build an app and get a job there. That was the most successful outcome I could envision.
We put up an early access page, and have signups right away. We launch Rewind for Shopify in June, 2015 (just Rewind at the time). We have hundreds of customers in a few months. https://apps.shopify.com/backup
In December 2015, one of our customers loses all their data through a Shopify App integration. He calls me in a panic. We’re able to restore his store exactly the way it was. Now I know we have a business - how big tbd.
We start charging customers the next month - January 2016. We’re working full time jobs *and* doing Rewind at night. We recruit two other friends to join us. The 4 of us work day jobs and then at night on Rewind for months on end.
By September 2016 we’re making enough money for one of us to quit and go full time. That happens - 1 developer at a time. This is getting real.
February 2017 I quit my job and start full time. It’s been 18 months of working two jobs, days and nights, to get to this point. My wife, though reluctant, sees the progress we’re making and agrees this seems like a good idea.
This time is different.
This time is different.
June 2017 we make our first hire - a sales person. We hire another developer a month later, a support person 2 months after that, and our first marketing person the month after. We’re a team of 8.
We double in size in 2018 and end the year as a team of 16. We actively protect over 6k accounts. @mattroberts leads our seed round in October of that year - the only investor to believe in us, 8 years after we first met. Building relationships take time.
We slow our hiring in 2019 while we figure out how to grow, and end the year at 25 people. We actively protect over 10k accounts.
In 2020, we accelerate our y/y growth and now actively protect over 20k SaaS accounts. We’re now a team of 65 people, spread all over the world (mainly in Canada, but we do have international employees), and are on track to double again in 2021. We’ll end at 120 people.
Along the way there have been many struggles. Thankfully my marriage recovered, but tragically one of our employees took their own life after we let them go. We’ve let others go and dealt with various legal threats, but thankfully nothing like that has happened again.
Feeling of personal failure. Divorce. Cancers. Suicide. The constant rollercoaster of emotions - highs and lows combine into one day. Building software is easy. Building a company is fucking hard.
As a side note, mental health struggles are real - if you need help please reach out to someone and talk about it. And let's support #BellLetsTalk 
day next Thursday. https://letstalk.bell.ca/en/
day next Thursday. https://letstalk.bell.ca/en/
Also many highlights. 3 Rewind babies so far. 80,000 businesses have installed our apps. We’ve built an incredible team of 65 extremely talented people - the most talented people I’ve ever worked with. I’ve connected with amazing CEOs, entrepreneurs and investors from all over.
My startup story is not unique. Many people struggle for years working, tinkering, trying to figure out the path to success - embrace failures and learn from them. Use that knowledge to build something successful.
