7 Questions With Kyle Racki

by Darrah Richardson January 26, 2018

7 Questions With Kyle Racki

When it comes to learning about business, designer turned freelancer, turned agency owner, turned SaaS startup founder Kyle Racki has climbed the ladder, fallen a few rungs, started the climb again, and has never stopped looking up. In his previous life as an agency owner, Kyle lived in full HD the struggles of trying to manage and grow a small business, lead a team, and thrive in a saturated and economically challenging market. (Oh, and squeeze in a personal life somewhere along the way, too). Now, as co-founder and CEO of Proposify, Kyle is focused on building beautiful online proposal software that helps businesses improve their sales, and on growing an innovative, thriving, company where good people want to work.

He’s also the host of the podcast, Proposify Biz Chat, where he interviews entrepreneurs, business adventurers, and creative thinkers. This week on the blog, we've turned the tables on Kyle and interviewed him for the latest installment in our "7 Questions With..." series. Thanks for your contribution, Kyle! 

1. How did you get started in business?

I never thought I’d be an entrepreneur growing up. It wasn’t until I was in my early twenties that I got interested in being my own boss, so I hustled to build my freelance business for about a year while I worked as a designer at an agency. Eventually I made the leap of faith and haven’t looked back. Now I run a 30 person SaaS business. Freelancing is a gateway drug to entrepreneurship, it’s the perfect first business because there’s no barrier to entry.

2. What is your morning routine?

I’d love to say that I get up at 5 am and practice yoga and meditate, but the reality is I’m not a morning person. I get up around 8 am, drive my kids to school, get coffee at my neighbourhood barista and then head to the gym to lift. While at the gym I listen to music or podcasts and that with the exercise gets me inspired. I head to the office around 10:30 am with a lot of energy and ideas.

3. What is your worst quality?

I’m impulsive and make decisions really quickly. Decisiveness is actually a pretty useful quality in a CEO because moving and doing something is better than staying still and doing nothing. But in my personal life, my impulsiveness has made my life harder than it probably needs to be.

4. What's a goal you're working towards right now?

I have a lot of business goals, but personally I’m working on learning my guitar scales. I’ve been a player for a long time and am pretty good, but I can’t solo for shit. Practicing scales is a bit boring to the people around me but it’s therapeutic for me, haha.

5. Who inspires you and why?

I find listening to Gary Vee gets me pumped up - I love his bravado and energy. I’ve been reading a book by Simon Sinek and he is pretty inspiring, he clearly loves creating content that helps founders and employees build companies they’re happy to come work at every day. I’m inspired by my business coach Dan Martell who had a rough time as a teenager, came out of it and thrived. Lastly, I'm inspired by several of my employees who moved to Canada from very different, very far away countries where they aren’t speaking their native language and don’t have family connections here. That takes a lot of guts and bravery, I don’t know if I could do it.

6. When was the last time you failed at something?

Just a week ago. I made some tough decisions about my company but didn’t communicate it in a timely way, and that allowed enough of a time gap that some of my employees became worried for their jobs.

7. How do you define "success”?

You’re putting something out into the world that connects with people. It could be a business, or art, or music, or anything, as long as it’s output and as long as other people find value in it. I don’t think you can just consume without any output and still be successful. And creating something no one else likes is ultimately not fulfilling. 





Darrah Richardson
Darrah Richardson

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