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“You also need to believe in yourself, be genuine, and continue to pay it forward so your success is interwoven with a bigger mission and the success of those around you”, with Mitch Russo & Kyle Campbell

Be passionate about what you’re building. Success won’t happen overnight. Trust your instincts, and find what really motivates you and inspires you to be great. You also need to believe in yourself, be genuine, and continue to pay it forward so your success is interwoven with a bigger mission and the success of those around […]

Be passionate about what you’re building. Success won’t happen overnight. Trust your instincts, and find what really motivates you and inspires you to be great. You also need to believe in yourself, be genuine, and continue to pay it forward so your success is interwoven with a bigger mission and the success of those around you. Lastly, never give up. Almost every successful person has had to struggle through difficult times. You have to be bold, daring, and accept a certain amount of risk to realize your dreams.


Kyle Campbell is the founder and CEO of CTO.ai, a platform for rapidly scaling DevOps teams. Founded in 2017, CTO.ai is a Slack-backed start-up that provides an open registry of shortcuts to help technical leads at startups quickly scale developer teams and streamline developer productivity 10x. Kyle has successfully guided the company to a team to 60 full-time staff, profitably, with 400% revenue increase over the last 18 months. Previous to CTO.ai, Kyle founded ‘Retsly,’ a company that helped developers access real-estate data from multiple listing services. Retsly was acquired in 2014 by leading real estate technology company Zillow, where Kyle continued to lead the execution of Retsly’s original vision by creating a safe and reliable platform upon which to build innovative real estate software. Based in Vancouver, British Columbia, Kyle is a self-taught developer, and has been programming since the age of 8. As an investor and advisor to a wide range of technology startups, Kyle’s mission is to democratize DevOps to help the next generation of workers reach their full potential.


Thank you so much for joining us Kyle! Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Igrew up in a very small town in Nova Scotia, where there wasn’t much going on. My mother was a nurse and my father was an engineer at a tire plant. I always had an entrepreneurial drive and the need for independence, as a result, I started exploring business ideas at an early age. My curiosity eventually lead me to the internet where there was a natural synergy because I could combine my interest in engineering with my drive as an entrepreneur. At 16 I started building online communities, mostly related to music that combined online marketing with offline concert events for big name rock bands.

After that, I forgot about entrepreneurship for a while and became completely obsessed with software development from 18–27. I worked at an early shared hosting company called Hostopia that went public and then alternated between startups and agency life for another few years. I eventually landed in Vancouver, BC at a great company called Blast Radius (acquired by Wunderman). This is where I learned the importance of culture in growing an organization.

I left there to work with Chris Neumann and as an early engineering hire I helped him start DataHero. I enjoyed that experience so much that after a year, I came to Chris and told him that I wanted to pursue this problem I learned about in the real estate industry but I wasn’t sure. He told me that if I didn’t do it, he would fire me. A week later Retsly was born and about 8 months into that company Zillow bought us.

This did a lot to give me the confidence I needed as an entrepreneur and with much left to accomplish, I left Zillow in 2016 and founded CTO.ai 3 days before my beautiful son Aiden came into the world.

What was the “Aha Moment” that led you to think of the idea for your current company? Can you share that story with us?

After I left Zillow, I wanted to pay it forward. So the logical next step was to take my proceeds of the Restly acquisition and invest in founders trying to bring their ideas to the world. I felt it that if I were to be a father that my son could be proud of, I would need to become a platform for other entrepreneurs’ success so I started off by trying to invest in local startups. As I did this, they would try to hire me as their CTO and it became apparent that they were struggling with something more costly than money. As I dug into it, I realized that there is a massive shortage of technical talent for early stage startups and the current DevOps market feels like a snake swallowing an elephant, costing them a great deal of time and money as they scale. Sometimes even preventing scale and preventing great ideas that addressed real needs from succeeding.

So I reflected on my experiences at Hostopia, Retsly and in general as an engineer who cares a lot about user experience and I thought: I think I can solve this by building the world’s best developer experience.

So I proceeded to bootstrap CTO.ai — mostly because I wasn’t entirely sure I wanted to jump back into venture.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

I don’t like to glorify the struggle but of course it has been hard. I think it has to be hard. If was easy, everyone would do it and it wouldn’t be so rewarding. When everyone else looks at something frightening and says, “nah, I don’t think I can do that” — I look at it and say “I have to”. I really believe that the only way a person can grow is through struggle so I appreciate the struggle but am careful not to glorify it.

Giving up has never entered my mind. That said, I would be lying if I said I didn’t in private moments, during some of the hardest moments, questioned my capability. You have to ask yourself those hard questions, that’s a part of the journey. But, no, I have never considered giving up. It’s just not an option.

It felt like giving up when we sold Retsly, and that dichotomy was pretty hard. People would high five me and be like congrats! I would be like, for what? I sold my company. It sucks.

The hardest time I’ve ever had was definitely bootstrapping CTO.ai however. The company was only 3 days old when my son Aiden was born and I was in such a complicated spot in my life as a result.

In hindsight, I probably should have taken a year off to relax but his birth gave me an insane focus and motivation. At the same time, it also felt like the clock was ticking. I knew that I had to pursue this business and grow it quickly and sustainably in order to create the future for him that he deserves before he was old enough to truly need me entirely. I decided I would invest 2 years and finite $ from our personal savings. I made a promise to myself that if I could bootstrap it to venture viability, I would dedicate 10 years to it but if I could not do this, I would keep it profitable or shut it down if it wasn’t. The hardest part about all of this is the clock ticking down because every second I’ve borrowed from my family, must be paid in full 10x. Time is my most precious resource.

If it weren’t for my family and everyone else who have supported me, I wouldn’t be where I am today. I’m fortunate.

As an entrepreneur you have to be obsessively passionate and driven to pursue your mission but you also need to know why you are doing what you are doing and who for. My priorities are very clear. I have no problem working hard because I owe this to the people who are counting on me.

So, how are things going today?

Today things are going really great. We maintained profitability, grew the business 10x more than my initial business plan assumed we would by year 2 and have completed a $7.5M seed round led by Slack and Tiger Global to scale The Ops Platform. We’re impressed by how quickly a community is forming around our mission to build the world’s best developer experiences for the next 60 million developers. We’re excited for the next 10 years and to see all the momentum we’ve had thus far has been incredibly rewarding.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?

There have been so many mistakes over the last 20 years but I can’t think of a funny one because I’m generally pretty hard on myself when I mess up, so I don’t think it’s funny!

A funny thing that happened by mistake when I was on my way home to Vancouver from the Bay Area, after 4 days turned into 4 weeks of run away VC meetings during our seed raise; I was tired and decided to spoil myself with a business class ticket so I could get a bit of rest before I arrived home to my family.

Just before the plane took off, a man came aboard and sat down next to me. At first I didn’t think much of it, but then I realized it was Stewart Butterfield, the CEO and founder of Slack. I introduced myself, congratulated him on everything he’d accomplished and told him about CTO.ai

At the end of the flight, I asked him to introduce me to the Slack fund and before I got to my car in the parking lot, I had an intro to Jason Spinell who is one of the most supportive, intelligent and well connected investors that I have ever worked with.

The lessons were two-fold;

  1. Sometimes you have to just enjoy the process and put yourself in a favourable position, even if you don’t know what the ROI will be. Have faith that if you put yourself out there consistently and responsibly, the mythical elevator pitch can and will happen eventually. It just might not be in an elevator but when it happens, be ready for it and speak up.
  2. Give back. None of us have gotten to where we are on our own. For Stewart to take 10 minutes to make that intro to Jason meant the world to me, It was late at night and I’m sure he had better things to do. As you find success, you have a moral obligation to pay it forward to those who come after you.

What do you think makes your company stand out? Can you share a story?

Our company is unique because we are laser-focused on building great developer experiences. Many companies in our space offer the equivalent to IRS tax forms to help developers do work but we believe that a big part of the $300B lost every year in developer productivity is due to this.

We believe that by enabling developers to streamline their own developer experiences on top of complex cloud native and SaaS tooling, we can help small, medium and large technology companies gain an edge while also helping developers to be successful in their career and simply enjoy their work every single day.

At Retsly and again at CTO.ai, when we started, I didn’t have the money to hire the most senior and experienced technology talent but I was able to find people who were graduating boot camp, who had a similar passion and drive that I do. By drawing on my 20 years of development experience, and giving them the tools to be successful, I was not only able to give us us a distinct hiring advantage in the market, but also an incredible culture where we root for and empower team members from the bottom up.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

If you need encouraging words, don’t do it — Elon Musk.

First of all, believe in your mission so passionately that you couldn’t see yourself doing anything else and have a clear reason for why you are doing it. If you don’t get this right, you’ll definitely give up. It’s far too hard to build a business if you don’t love what you do every single day. Second, make sure you have a clear reason and foundation for why this mission is important to you. For me, it’s my family, and the open source developer community whom I’ve been fortunate enough to learn my craft from. Lastly, spend time on yourself; learning, working out, even taking a vacation here and there. You are going to have to work harder than you ever did before, just accept that it will be hard but that doesn’t mean that you can’t build in time for yourself so that you can stay on top of your game. Know yourself, know your tendencies, work hard to hire people around you who are truth tellers and will enhance you, rather than tear you down. Invest in culture early and protect it at all cost. This is the number one thing that will ensure you don’t burn out. It takes a village.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful for who helped get you to where you are? Can you share a story?

As I’ve shared above, I’ve had a lot of help along the way and I appreciate and acknowledge this every single day because I know that I could not complete this on my own.

Based on your experience and success, what are the five most important things one should know before one wants to start an app or a SAAS company?

Be passionate about what you’re building. Success won’t happen overnight. Trust your instincts, and find what really motivates you and inspires you to be great. You also need to believe in yourself, be genuine, and continue to pay it forward so your success is interwoven with a bigger mission and the success of those around you. Lastly, never give up. Almost every successful person has had to struggle through difficult times. You have to be bold, daring, and accept a certain amount of risk to realize your dreams.

If you could start a movement that would bring the most amount of good to the most amount of people, what would that be?

Given my experience and what I’m good at, I’ve already started this movement with CTO.ai. Empowering 60M developers with the tools they need to be successful is not something I take lightly and growing our community goes well beyond upleveling people and helping them build successful careers. When I think about growing this community, I think about the type of future I want to build for my son and the kind of world that the next generation of people entering the workforce can be proud of. I can’t imagine doing anything else that would be as equally rewarding professionally or personally.

How can our readers follow you on social media?

https://www.linkedin.com/in/slajax/

https://www.linkedin.com/company/cto-ai/

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