Maria: Did you always think your career path would lean more towards entrepreneurial endeavours?
Kristina: Yes, to a large extent I did. I come from a family of entrepreneurs and it’s always been an assumption that my brothers and I would work for ourselves some day. I had a passion for being able to take an idea and turn it into something that drove me to start a couple of businesses, probably long before I ever should have. Those early trials and tribulations helped me learn a lot about myself in terms of my physical limits as well as the gaps in my knowledge.
My early experiences with entrepreneurship gave me a well-rounded perspective of what it’s like to start a business, hire your first few employees, do sales and marketing, knock door-to-door, advertise on the radio, and other grassroots entrepreneurial activities. By the time I graduated from UVic and went into the business world and joined a successful company like Crystal Decisions, I saw how a company like that ran at scale. It was really impressive.
As I progressed through my career, that passion and that “roll up your sleeves and just get it done” never left me. By the time I moved into venture and was looking at companies to invest in, one of the things that always stood out to me were entrepreneurs who weren’t afraid to roll up their sleeves and just get on with it, because those are the ones that really ended up being successful. That’s the fun part of being an entrepreneur, but it’s also the really hard part. Now, it’s the area where I think I can help other entrepreneurs figure out how they can take their ideas and turn them into something real.
Maria: When you worked at Crystal and Microsoft, you chose the product marketing and product management paths. How important are those sorts of disciplines within companies and how are they different?
Kristina: I think product management is fascinating because you end up touching every aspect of the company, and to me that’s really fun. You’re the hub in the middle of all the different spokes – sales, marketing, partnerships, product development, and customer success. You get to touch it all, and that was the part that I just loved about it. It’s a great position to be in if you want to learn and grow, and see how the mechanics of an organization work.
I think for anybody who’s got any kind of an entrepreneurial bent to them, or any kind of interest in really getting a handle on how companies grow, that’s a really good discipline to be in because you get exposed to it all, you touch it all, and you get to learn it all.
Maria: What are some other key learnings from working at those large organizations?
Kristina: I didn’t realize I was learning at the time, but then I realized what I had learned when I left to start Integris, it was pretty funny to see how much of what those organizations are is the culture and the people and the operations that make it what it is. When you jump to start a smaller company, you don’t have any of that infrastructure in place that provides just a ton of buoyancy for bringing any new ideas to market.
Another incredibly valuable lesson was how much a business can be amplified through a partner network, and it’s something we definitely leveraged at Integris as well.
Maria: So you’ve been at big companies, started your own and been an investor, all three sides, what are the key differences, the pros and cons, and what has brought you back to investing?
Kristina: I realised that the thing that gives me the most energy is working with entrepreneurs. Even when I was doing it myself, I found that I spent a lot of time working with other founders, particularly female founders, to bat around ideas, be a sounding board, and providing advice. When I was an entrepreneur, I found that the founder community provided a safe space to work through things and problem solve that was really valuable and energizing.
To me, that’s what being a good investor is: being a good business partner, sounding board and co-conspirator to solve hard problems. I like it. It just feels natural.
Maria: What do you think are the significant barriers for women in leadership roles these days?
Kristina: I think the biggest barrier to female leadership is unconscious bias, and I would say that’s true of any minority group. People don’t think of themselves as biased. And yet we all have biases. It takes a lot of emotional strength, self-awareness and accountability to acknowledge and hold yourself accountable to the biases you hold. It’s pretty hard as an investor to do that, because it’s ultimately a judgment call. You can collect all the data in the world, you can build all the financial models you want, but at the end of the day, you’re making a gut decision to put your own money and other people’s money behind that judgement call.
My advice for any entrepreneur, but particularly minority entrepreneurs, is to get to know your investors well in advance of ever taking money from them. You’ll want to make sure that they’ll be great board members, great advisors, and that they’re going to be the kind of investor that will be in your corner during tough times, hold you accountable, and work with you through problems versus become more of a problem on top of whatever it is that you’re facing. And when you’re a in the minority group, getting to know the investor well in advance is the best way to overcome unconscious bias. People find it really difficult to be biased once they know you as an individual, an entrepreneur, and as a person. So, my hack is to get to know investors well before you ever need money. Because if you’re only meeting your investor when you actually need money you’re way too late, and there is too little time for you to figure out if you actually want them on your board. It’s easier to get divorced than it is getting rid of a board member, so you need to make really, really sure that this is the person you want to do business with for the next five to 10 years.
Maria: For our listeners to know how you would describe yourself, so if you were to choose only one word, or what would it be?
Kristina: I guess I would say tenacious. For example, I see something that I’m passionate about or have develop conviction about, nothing stands in my way. I will push through mountains and make it happen. That’s been a constant theme throughout everything, whether it’s just deciding at the ripe old age of 19, “I’m going to a start a company.” Or, say, “Hey, I’m going to leave my cushy job in venture, go live the life of a starving entrepreneur and roll my dice and see what happens.” I just do it and get on with it, and I think that’s one of the things that I look for when I’m looking to invest – tenaciousness.
I’m looking for someone who’s going to go and plough through a mountain to make things happen because being an entrepreneur is incredibly tough. It pushes you in ways that you never expected it would. When you start a company, it’s like you’re holding a mirror up to yourself and you’re seeing the worst and best of yourself every day, but you focus on the worst. You constantly ask yourself, “Why is that going wrong? What’s happening?” It’s very, very humbling and extremely hard. In order to be able to deal with the ups and downs and everything that happens, you’ve got to have real tenacity to you and a desire to succeed that goes beyond any other emotion you have. So, it’s that tenaciousness that I look for, and that’s what helps me develop conviction about an entrepreneur.