When it comes to entrepreneurship, there’s no better source of information than those who have lived it themselves. That’s why we feel so lucky to welcome entrepreneurs Kyle Racki and Kevin Springer to talk about partnership, startups and the challenges of building a business.

If those names ring a bell, it might be because we featured the duo’s latest venture, Proposify, in a blog piece last week. In that piece, we talked about how Proposify can help you create beautiful business proposals and also help you save time by providing a cloud-based solution that streamlines the process. We also mentioned that Proposify wasn’t the first business that Racki and Springer started. What else have they done together before this? And why, in a world where successful partnerships can be so difficult to forge, does their alliance work so well?

Let’s find out…


Blake J. Harris: Have you guys always had an entrepreneurial streak? Or was that passion and skill set something that surfaced later in life?

Kyle Racki: That’s an interesting question. I actually wrote a blog post on that recently, all about nurturing entrepreneurship (Why Kids Should Be Taught Entrepreneurship Early On). Because actually, in my case, I didn’t come from an entrepreneurial background at all. My mother was a nurse and my father worked at a nursing home doing maintenance repairs. So neither of them were really keen on the idea of starting a business. It was always this really scary thing. “Don’t start businesses. They’re likely to fail!”

Blake Harris: [laughing] Well, I think we can all relate. That’s a fear–whether it comes from our parents or from that risk-averse voice in our head–that can be hard to ignore. So given your background, Kyle, can you tell me what later gave you the confidence to go for it?

Kyle Racki: A lot of the credit should go to Kevin.

Kevin Springer: Thank you!

Kyle Racki: We’ve been business partners for about ten years now. By the way, Kevin–because I know he loves it when I tell people this–he’s 20 years my senior. And Kevin had run businesses before so, as I started to become frustrated about working for others, he played a key role in coaching me–and giving me the confidence–to go out on my own. First as a freelancer and then, ultimately, to start a business together.

Blake J. Harris: So, Kevin, as Kyle just mentioned, you were no stranger to entrepreneurship. And, by extension, I’d imagine you’re no stranger to the difficulties that often crop up in a business partnership. What is it about the relationship between you two guys that works so well?

Kevin Springer: Yeah, I’ve had quite a few partnerships in the past. In different variations of different businesses. From food and beverage to promotions. With Kyle, I think it’s the old cliché that sometimes opposites attract. We both have different skill sets. There’s a little overlapping, but our strengths really complement each other. And also we have a lot of respect for each [other]. I think we listen to each other. I mean, this is our second business together. And, as you know, a lot of partnerships split up after the first business.

Blake J. Harris: To that point, I think a major reason why partnerships do split up is because it can be tough–as a team–to work through the tough times. And every business has tough times. So how do you guys manage to make it through those bumps?

Kevin Springer: We’ve been through a lot together and this may sound kind of sappy but we hold each other up when we need to be held up. And also, regardless of how things are going, we always listen to each other and respect each other. And I admire Kyle a lot, outside of the office as well. He’s a great parent and I think that shows a lot about a person.

Blake J. Harris: That’s a very interesting point, about how outside-the-office attributes can help inform a person’s character. So we now have a little bit of a sense of why you guys work well together, but tell me a bit about how. With Proposify, specifically, can you talk about how the idea came about and how the two of you executed on that vision?

Kevin Springer: Sure. It started years ago, back when we were building our first business: a digital ad agency called Headspace Design. It began, really, as just kind of an idea floating around the agency. I think, maybe, the first time there was a glimmer of hope that this might go somewhere was when we hired someone in-house to work on this project.

Kyle Racki: That person we hired was Jonathan Down, our current CTO.

Kevin Springer: Yeah, having Jonathan work full-time on the project was a major milestone (even if we might not have fully realized it at the time). Because, at the time, what was really holding us back was trying to fit this proposal-software-project into our regular production schedule. So that was definitely a big turning point. And I’d say the next one was when we sold the agency and got funding from a provincial venture capital agency, Innovacorp. The sale [of Headspace] and the seed from Innovacorp, that gave us the freedom to really go for it. That was like a new chapter opening.

Blake J. Harris: What were some of the initial challenges?

Kevin Springer: Well, we realized quite quickly why our competitors did not design a powerful customer editor…because it’s frickin’ hard!

Kyle Racki: [laughing] Yeah, so I would say the biggest challenge at first was the product itself. It took about a year and a half to build the minimal viable product, get it out there, get feedback. Figure out what the bugs were and what features it needed. And, from there, it was just a matter of honing it and refining it to the point where it was actually solving problems.

Blake J. Harris: Going back a little bit–before solving problems with the product itself–can you tell me about how the problem was created. You mentioned it was “just kind of an idea floating around,” but I’d like to hear more about the idea. What was that kernel of an idea?

Kevin Springer: Well, to step back to Headspace. We were such a new and young agency, but we were actually winning some pretty big business and, when probing about why, our clients often said it was because of our proposals. Kyle’s the designer between the two of us, so he was designing these beautiful templates that clearly had a value in and of themselves.

Kyle Racki: Just to add to that point, I think the best products come from someone’s personal pain. In this case, we were basically scratching our own itch and, from that, it helped create a product that we realized others could benefit from using.


Kyle Springer: From a high level, I think one thing we did right was to focus on just one vertical. We wanted to become the basecamp of proposal writing in a sense. A lot of startups make the mistake of going after everybody, but we were pretty refined about our initial objective and our messaging.

Kyle Racki: I think focusing on a niche was important. As opposed to thinking about every type of business document out there, we decided to focus exclusively on proposals. And from a client standpoint, we decided to focus only on agencies at first. That was important. Because we could have gone after every industry. And, to be honest, when we met with potential investors, that was always a big question of theirs: Why only agencies? Go after every industry, they’d say! But we preferred the concept of beginning with a small fire and keeping it really hot before starting to throw logs on it and grow it. We use that analogy a lot.

Blake J. Harris: That’s a great analogy. And a wise business decision, not trying to be the all-everything-to-everyone company. In that respect, the name “Proposify” is perfect. How did you go from the original name, Pitch Perfect, to Proposify?

Kyle Racki: [laughing] Well, originally the two names I came up with were “Pitch Perfect” and “Big Deal.” They both weren’t great. I asked some people around the office and they liked Pitch Perfect better. So we went with that, for a little while, until we started meeting with investors and potential clients. They were like, “Oh, so it’s for investment pitches?”

Kevin Springer: Or people thought it was a musical app.

Kyle Racki: Yeah, and then the last straw was when the popular movie Pitch Perfect came out.

Kyle Springer: By the way, ours was called Pitch Perfect a year before the movie!

Kyle Racki: So we realized we needed a name that people would immediately associate with proposals. Hmmm…what says proposals? And then Kevin suggested “Proposalify.” And I was like, “How about just Proposify?” And that’s how Proposify was born.


Blake J. Harris: Collaboration, as always! Which is a good segue to my final question. Having now worked together for several years, what are some of the things that you two have learned from one another?

Kevin Springer: So much. As Kyle mentioned earlier, I’m 20 years his senior. I’m the last year of the baby boomer generation. And as someone in his 50s (especially with the average age of our team members being somewhere in their twenties), sometimes it’s overwhelming. But Kyle’s very patient and understands that I didn’t even grow up with computers. Not only that, but he makes an effort to help me learn. Kyle’s a sponge for knowledge and he’s always sending me articles and blog posts that help keep me up to date or see things from a different angle. It’s an ever-evolving industry and Kyle really stays on top of that. So I’ve learned a lot from Kyle and I’ll continue to do so every day.

Kyle Racki: There’s a lot of things that I learned from Kevin. I talked about early on how he kind of gave me the confidence to go out and actually sell my services; to help me differentiate myself from others and play to my strengths. Kevin’s also very good at getting systems in place to help automate the business. Like, in the past, I’d say that my mentality was that in addition to trying to cook the meal, I was also running out to serve it to people, and taking orders while i was out there. I was trying to do everything because, maybe, I didn’t trust other people. So Kevin helps find the bottlenecks, and is great at strategizing ways around that. I think every business can benefit from the concept of trying to work yourself out of a job. I think that’s a healthy thing for a business owner. It just makes you a better entrepreneur to know how to do that. To know how to get the fire going and then step back and let everyone else work on it while you guys go onto the next thing.