Sandi Gilbert – Fintech leader & community builder, shares why women should consider angel investing

Jennifer Stewart: Sandi, let’s start with your backstory. You’ve been working in angel investing and FinTech for years now, and you know, frankly, it’s not a very common industry for women. How and why did you get involved?

Sandi Gilbert: I grew up in an entrepreneurial family. I always say I was born on a farm in Manitoba, not much more entrepreneurial than a farmer! But I always knew that I would foster my own path. I knew entrepreneurship was where I was, but I started by raising capital in the investment banking space in Calgary many, many years ago, and I’ve always been involved in the private markets, always helping entrepreneurs access that capital. Now, in Calgary, of course, that was oil and gas early on, but as the years went on, it was really any type of business, and what I knew was that it was really hard to raise private capital. Number one, whether you are a man, woman, old, young, black, or white, it didn’t matter.. it was hard to raise private capital because it’s a complicated space. There are a lot of regulations regarding raising money. 

After doing an entrepreneurial venture, my partner and I decided that we would try to put technology to work to make it easier to raise capital. Our mindset was that if we could put a deal online, and investors could come and see that private deal and all the paperwork could be done online, it would be efficient and give maybe some democratization to the private capital markets, where people always didn’t have access to that deal flow. So, fast forward 10 years, and we were an entirely different company than we set out to be. DealPoint is a SaaS product licensed to the industry, and it’s just a workflow that helps those entrepreneurs access capital and efficiently close a private placement. 

In the middle of all of that, I had a colleague run up the stairs at my office. Her name was Michelle Scarborough, and she said to me, ‘You guys are doing some really cool stuff here. I think that you should join NACO, the angel capital organization.’ I didn’t really know what angel investing was, although we Angel invest here all the time in Alberta, always, some individual is writing a cheque to a promising entrepreneur to help them start a business. But we didn’t really define it like that so much back then. So that’s how I got involved in NACO, and that’s how I started to understand the impact that individuals who are writing those personal cheques can have to help that entrepreneur grow and build that business. Secondly, as you ladies know, small businesses are the foundation of economic output in this country, and I just haven’t looked back.

Catherine Clark: Jen and I want to follow up on pretty much everything that you’ve just said! One of the things that I found really inspiring when I was reading a little bit more about you before this conversation, Sandi, was that you kind of glossed over the fact that you worked really, really hard to get your first job in this industry. My understanding is you went and, quite literally, knocked on doors and just said, I want to work for you. Can you talk to us about that grit and determination?

Sandi Gilbert: Yeah, I mean, I was young, naive and confident. I would say those are the three things that led me to the door knocking. I learned, just in a roundabout way, about this thing called investment banking and how the stock market worked, and commodities. And I said, ‘This is what I want to do.’ I came to Calgary, which was pretty young at that time. I had an older brother here that was in the oil business as an engineer, and I just went to every brokerage house, and I knocked on their door and said, ‘Listen, I know a little bit about this, because I’ve had this little, tiny experience, but I can learn, and I want to learn, and you just need to hire me.’ And, of course, every door was closed along the way. 

And then along came this firm, Nesbitt Burns, which is the brokerage firm that I went to work for. I got a great mentor within Nesbitt, Stuart Dunn, who I’m forever grateful to for really introducing me to the world of finance. And he really took me under his wing. We started a business together with a few other people, and I really just learned a lot from Stuart, and that’s really what it takes. You need to A, try, B, have confidence and C, look for somebody within the organization that can help you and take their help.

Jennifer Stewart: How did he know when he had found that person? 

Sandi Gilbert: That’s another good question. Stuart was from Montreal and was in the West for the first time. He was funny. He used to go for lunch every day and come home with a joke that he put in his joke book every day. And we just really hit it off from that kind of humour standpoint. And he was from a world that I didn’t know. You know, he had been kind of, let’s call it, old money Montreal, and he very much intrigued me and was willing to share and help me learn. So it was, it was a great early relationship for me.

Catherine Clark: The mentorship question is really interesting because many of the women we talk to describe having mentors who made a big difference in their lives. There’s also some sense that women should be looking for women mentors. Can you talk to us about that? Because it seems like you may have had women mentors, but you certainly had two very strong male mentors. What do you recommend?

Sandi Gilbert: So I grew up with three really strong women: my mother, aunt, and music teacher. All of them were trailblazers in that era, all university-educated. They are just really, really, really strong women, running their homes and running businesses and volunteering immensely within the community. So, I had very strong women who led me down my path. But from a business standpoint, entering into the private capital markets, there weren’t many women for me to be mentored by. So hence the Stuart story. 

I don’t think it really matters, in all honesty, whether it’s a man or a woman. Still, you just need to find the right person that can support you, you can be vulnerable with and, you know, share your stories with. But today, fortunately, there’s many, many more women in business that are willing to support the next generation of women. 

Jennifer Stewart: Sandi, what are some of the biggest challenges you faced along the way in your career, and how did you overcome them?

Sandi Gilbert: I never really felt like I was being held back because I was a woman. It never really crossed my mind that that was a challenge for me. But I have to say, in the last 10 or 12 years, kind of entering this venture capital space is when it kind of hit me like, ‘Hey, there aren’t many women here, for sure, and I have a lot of doubters.’ When I came into the opportunity at InterGen to run the InterGen fund, I had a lot of doubts. 

And that was the first time that somebody actually said, ‘You’re a woman, maybe you can’t do it.’ But I just didn’t let that stop me. I knew I was going to be able to do it, and I went forward. But really, I think you have to lead with confidence. Everybody has things and obstacles in their life that are going to be a challenge and little minefields along the way. So don’t say, ‘Oh, I can’t do that, or that happened to me because I’m a woman,’ you just have to do it. And, confidence is a word that I overuse, I think, but you have to have a lot of confidence, or at least fake it till you can make it. 

Catherine Clark: If you were talking to women founders, what do you think they need to be thinking about if they’re planning to launch a business or try to put a new product out on the market. What advice do you have for them?

Sandi Gilbert: A couple of things early on in a business are important. Number one is, if finance isn’t your gig, attach yourself to a good finance person, bookkeeper, accountant, CFO, somebody that can help you organize the business as you are growing. And I think that’s really, really important.

The second is that you can surround yourself with advisors that want to help you, and you can get advisors from different aspects of life. If you’re not technically savvy and you think you need a younger person to help you on that front, surround yourself with that so your advisor network isn’t all of your friends or all of the peers that you went to school with or the people you ski with or the people that you golf with. You need to find different people that can support you along the way, and then those people can help you put all of the pieces together to ensure that you can have success at that business.

Jennifer Stewart: Sandi, what would you say to a woman who has had a successful career and now wants to look at Angel investing herself?

Sandi Gilbert: Yeah, we’ve got a big turn coming here by 2030, some of the predictions say that most of the money is going to be in the hands of women. And you know, women aren’t big investors. So I look at that and I go, ‘Oh my gosh. Who’s going to fund our entrepreneurs if we don’t have any men writing those cheques?’ So I think we’re at a critical time to ensure that women understand that they can, and have the opportunity to, invest in early-stage companies and young founders. 

It’s a really important time for women to really take a look, step up and say, ‘I’m going to support these entrepreneurs,’ and they’ll learn so much. I mean, that’s the fantastic thing about angel investing. All the time, we’re going, ‘Oh my god, I had no idea somebody was doing this,’ whether it’s in health care or finance or sports. It’s just amazing what entrepreneurs are doing out there today.

Catherine Clark: To go back to Jen’s initial question, you’ve identified that we’re not communicating to women to help them understand that this is a field where they can make a critical difference with the money that they may have to invest. How do we get that message across to them?

Sandi Gilbert: We need to invite them to these events. People say to me, ‘How do I get started?’ or, ‘How do I become an entrepreneur? How do I become an investor? How do I go to work with an early-stage company?’ You have to get out into that network. 

So we, as the people who are throwing the events or doing the educational sessions, need to ensure that we are including and making it comfortable for women to be at those events. I do not think it should all be women at these events, because I think men can share much of their history of investing with women. So to get them there, to get them to understand the types of companies that are making a big difference, that they can get behind and back, that’s the important side. 

Jennifer Stewart: We’ve talked about hurdles and challenges on the horizon, but also opportunities. Why should women founders take the leap? What have you seen in your career that convinces you that this is all worth the risk?

Sandi Gilbert: Well, not everybody should do it. I would start with that. You have to have the mindset that can handle the ups and downs of what is going to happen on your entrepreneurial journey. But the reality is, there’s lots of women out there now that have taken the leap. So there’s lots more people for us to look to. 

So, first of all, you have to believe you can do it. Those are important things for women to consider. And the reality is, entrepreneurship can give you more freedom than a regular nine-to-five, so it might mean that you’re working more hours, but you have the time to take an hour in the middle of the day if that’s what you need to do. So, work-life balance can also work for entrepreneurs; although I would say that entrepreneurs tend to work a little bit longer, they don’t have to work in the structured world that you would if you had a job that you had to go from nine to five every day.