CAN-AM Stories – Entrepreneurship Across the Border: Kristine Carey

In partnership with The U.S. Embassy in Canada, Startup Canada is celebrating and spotlighting women’s entrepreneurship across the border – speaking to leading founders to learn more about their journeys, and the vital role of cross-border collaboration on their entrepreneurial successes. Startup Canada was pleased to sit down with Kristine Carey, American founder and reinvention specialist, to learn more about their journey.  

Kristine is the Founder of a San Francisco based business and life coaching company,, which specializes in reinvention strategies for solo entrepreneurs, as well as small companies and their teams. She is also a seasoned professional speaker and community builder. 

SC: Tell us about you and your businesses! Who are you and why did you start your business?

I’m a reinvention expert. What I really do is help people figure out what’s important to them, what their strengths and superpowers are, and how those things show up in their business. I was originally trained as a life coach so a lot of my “come from” has a holistic approach to it. What I’ve discovered over the years is that I really have a knack for talking to people about their work, especially people who have what I think of as “entrepreneurial swirly brain”. Essentially if you don’t really think in a linear fashion and you want to do stuff on your own terms, I have a knack for having those conversations. I have been that person who was stuck in regular jobs and thought there was something wrong with me. It wasn’t until later that I realised that people like me don’t tend to have regular jobs. So I made up my own thing because I’d always wanted to.

I’m the first generation of coaches that didn’t invent the field of coaching. Everybody who has taught me were the people that literally created it – all of my mentors are the OG coaching people. Coaching is a whole different kind of world and profession at this point all these years later, but when I started there were no role models except for the couple of people I knew. The International Coaching Federation, which is our professional organisation, had barely gotten started. I didn’t even know coaching was a thing. A lot of coaches, all of them at that point, were self employed because corporations didn’t even know what coaching was. So at that point it all came together –  I wanted to do my own thing, I just discovered that I have a knack for this thing called coaching, and that most coaches are self employed. So I decided I was going to give it a try.

My employer and I had a little heart to heart and a mutually agreed upon “parting of the ways”. I had basically a two month runway to get out of that job and get my own thing going. It ended up taking me much longer than that just to get started but that’s how it all started. More than a little shove out of the nest by the employer just not agreeing on what we both wanted.

SC: What’s been your greatest success so far?

Sticking with it all these years. It’s really hard some days, especially in the beginning when you feel like you don’t know what you’re doing. I just attribute my longevity and success to being really really stubborn… and also really really not wanting to go back to work for anybody else. One of my mentor coaches used to tell this story that every six months or so after she started her thing, she would just put on a suit and polish up the resume and be like “this getting clients thing is too hard and I’m just going to go get a regular job” and then they would be like “okay, Carol, here’s your two weeks vacation, this is your desk, these will be your tasks” and she would just be like “oh, I don’t think so”. She did that at least three times over two years before she finally realised that she was never going back. So ultimately, I just took her at her word and didn’t even pretend like I was going to go back no matter how much I didn’t love the stress of starting and didn’t really feel like I knew what I was doing. It’s all about pure determination and sheer willpower and being really stubborn about it.

SC: What is the best part of Canada’s and America’s startup ecosystem and community?

I’m very pro Canada – I love doing business with Canadians. Some of my favourite coaches have been Canadians and two people spring to mind in particular that I met early on in my coaching journey. There’s just a different vibe about it. The US and Canada are both really supportive of entrepreneurialism in general and yet the way the two countries go about it is “same same” but also different. I like the Small Business Administration – that’s where a lot of our stuff comes from in the US, I used to teach there in the San Francisco office. I also know that Canada has a lot of support for entrepreneurs. The guy I referred to a second ago took advantage of that and got grants and stipends early on to get his venture off the ground. So I don’t know that one is better or worse, but I like them both and it would be kind of cool if they could all be combined into one really groovy thing.

SC: In one sentence, what does being a woman entrepreneur mean to you?

Being able to call my own shots.

SC: That answer has been echoed in every single profile interview so far. It’s neat to hear it echoed by women founders across the border. 

Well, as women in the workplace there’s a reasonable amount of sexism and disempowerment. I feel like I don’t have to put up with it if I’m doing my own thing. I choose who I work with and how I work with them. It has still happened, but it’s pretty rare.

SC: How has the pandemic impacted your business?

It was pretty stark. The repercussions are still being felt. The majority of my income up until prior to the pandemic came from individual coaching with solo entrepreneurs or small business owners. I have always done speaking – I’ve made presentations and team facilitations, but that was never the bulk of how I made my income. So when the pandemic started, half of my client load disappeared within a month… just like that. Not great for the bank account or cash flow. So I applied for an EIDL loan here in the US and I got it, which was awesome. I still have part of that money in the bank. Thank the gods, really, in case I need it. 

The second part of that story is actually a little bit more interesting. I feel like the first part I just discussed is shared by a lot of us that have gone through something like this. The second half is that I ended up hitting the road and doing a lot of travelling almost continuously for six months during that first pandemic year way out west with my boyfriend at the time and we just kind of went wherever we felt like going and just tried to stay away from people, which worked out great. In doing that, I ended up in rural Montana multiple times, the middle of nowhere in Oregon, same in Wyoming. The kinds of places where it’s not dense and there’s not a lot of opportunity to do much of anything except just sort of hanging out. Being in that type of stillness made me realise that there was a busyness – almost a frantic-ness – to the way I’d been doing business. I hadn’t really thought of it before, I always assumed that’s just how it was. But being in the middle of nowhere like that the idea came up all the time, because I couldn’t act that way. Number one I wasn’t in one place long enough to feel entrenched and get into that sort of normal “you’re at your desk level of busy work” that happens. Number two, because of that, I just flat out blew off all kinds of things that would have been on my normal to do list. I just didn’t have the bandwidth – it felt like the apocalypse was happening. So I was like “well I don’t really have much to lose and nothing seems like it’s on fire as a result of me not continuing to feed the machine in these ways I’ve done it in the past”. So I just stopped doing all of that – I only did what people paid me for. I didn’t do much beyond that except just ponder the nature of the universe. As a result, long story short, I ended up deciding that I was going to reinvent my business model. So I’ve flipped all that stuff on its head and I’ve declared myself a speaker and a writer who runs an online community to continue the conversations that drew those people to my presentations and workshops to begin with. I can use my coaching skills in the online community, but the rest of my time is going to be writing and speaking. I love that because it’s a different way of approaching what I have to offer. In the coaching world we often think of it as the therapy model – a dollar rate for a one-on-one hour. There’s other models as well, but that’s the stereotypical one. But during the pandemic I had the opportunity to do more team facilitation work – it literally fell in my lap while I was in the middle of nowhere in Montana. Sort of seems ironic, but just a little bit of a testimony to some of the seeds I had laid earlier in the year. So I was like “alright, if this way of working wants to come to me, I’m just going to follow it” and that has led me here. It has been this giant reorganising of my mindset into what’s possible, really doing what I feel like I’m best at, and how I can offer it in a way that’s best for me and the people I want to work with. Like most of us who work for ourselves, I am just leaning into whatever feels right and trusting that it will lead me to where I need to go.

SC: What has been your biggest struggle in navigating cross-border sales and operations?

You know, really, the main thing is just the money because the conversion rate is different. No matter what you’re charging, it’s never the amount you think it is on either side. So my old Canadian coach used to charge American dollars which was great because then I always knew what it was but my bookkeeper who is Canadian charges me in Canadian dollars. We just finally had to agree on “this is the number and whatever the conversion rate is, one of us is sucking it up”. 

SC: On the other hand, what are the biggest benefits you see in cross-border sales and operations?

In general I just love working with people who have different mindsets. I think that’s why I like the reinvention topic and entrepreneurs, specifically, even if they’re tiny businesses. When you’re doing business with somebody from another country, you’re automatically going to make different assumptions because you don’t grow up in the same conversation. I’ve had people from Canada, New Zealand, Germany, and other places hire me because I’m an American and they wanted to do American style business. Meanwhile, of course, I end up learning stuff about their culture and how they do business and their assumptions. 

The six months I spent working with a French lady and learning how that all worked was a real crash course and a realisation of “wow, things are not the same over there”. So as much as I think that Americans and Canadians have stuff in common, which we do, we also do have these differences that pop up. Those differences are for the better, a lot of times. They make you examine your assumptions that you didn’t even realise you were making.

SC: Has going global given you an advantage in bouncing back better and faster amid the pandemic?

I haven’t really done much with that at this point, to tell you the truth. Now that I’m starting this online community where there will be live interaction and an online portal where we can exchange ideas and have discussions, my hope is that I can attract more people from other countries, period. Canadians are very easy to work with so I would love it if I had more Canadians in my orbit. That feels like the main opportunity.

SC: Many women founders have cited mentorship as the biggest support in growing successful businesses. Have you found value in mentorship, either as a mentor or as a mentee?

Boy howdy, yes it’s been great. The coach I mentioned – she was my coach during coaching school – she mentored me for two and a half years or something like that when I first got started. I was the first graduating class from my coaching school and the lady who founded that kind of mentored all of us and took us under her wing in a way that I know wasn’t true for subsequent classes. Because we were the guinea pigs, she was just trying stuff out to see how it works. So there’s been several people along the way, one of whom has become a dear friend, that I really value for teaching me how business works and how to be in integrity when you do it.

I have mentored some folks as well because I love being able to do that. It’s actually one of my superpowers, and I don’t get a chance to do it often so it’s ice when it comes up.

SC: Have you ever experienced running into a problem where seeking mentorship or advisory support has helped guide or empower you to find a solution?

Yeah, if I feel stuck I have several people that I go straight to that are further down the road than me. I also have a mastermind group that I founded with another coach. We’ve been running for eight or nine years now. She and I, as it turns out, went to the same coaching school but a handful of years apart. I was on a coaching business panel and she was one of the students so that’s how we met. On top of that, we both live in the San Francisco Bay Area. We’ve been friends ever since. So through the local coaching community, we’ve met a bunch of people who have kind of come and gone from our group but now there’s a “core three”. We meet every month and while it’s not exactly mentorship, it’s very much sharing of resources, best practices, and an opportunity to share what happens when you’re trying to do your own thing. Some days it works better than others. We all have similar businesses but not the exact same thing, so it’s fun to explore the overlap and then see which direction other people are going to try and get/offer support. During this whole journey, groups like that make it feel richer and more effective. I know I have a team of people on my side, and I’m on theirs.

SC: What does being part of this partnership mean to you? What do you hope to achieve?

I have a real soft spot in my heart for Startup Canada. I’m really flattered and humbled that Startup Canada got in touch with me to do this – to participate in the cross border initiative and discover, if you will, how we can make trade and business easier. I’ve been participating in the #StartupChats off and on for years,  first under someone else’s banner and then under my own. I just really dig the people I meet. It means a lot to me because, again, the idea of integrity comes back because I know there’s a lot of people that show up specifically for the #StartupChats who are really good people. I’ve gotten the chance to get to know a few of them a little bit more personally. In general I like enhancing the business ecosystems that I’m a part of. The stuff that Startup Canada has created – any bits of it that I’ve had the chance to interact with – have been meaningful and helpful.

SC: How can we learn more about your journey and organisation?

My website is Coming soon there will be a web page on that website that leads to this new online community – I’m just putting the finishing touches on it, but it will be ready soon. You can also get on my newsletter as well. It comes out a couple times a month and is just musings about entrepreneurial type things and what it’s like to be a human trying to do business. I have a couple of monthly themes that I revisit regularly. So there’s always something going on. The easiest way to get a hold of my newsletter is – like every self respecting website – the giant “sign up here” box. I’m available for facilitations, speeches, and any of that stuff – just head over to the website.

SC: Do you have any recommendations on how women founders can expand and capitalize on their network to help them on their journey?

Don’t be afraid to ask. Women are generally under askers. Be real and genuine. Be supportive and helpful, but not in that weird manipulative “you really want something” kind of way. Just be you. 

I think one of the best examples that comes to mind is a client I had who has since become a friend. She’s a professional organiser and she wanted to add coaching into her tool bag because a lot of people have issues with why there’s so much stuff in their house, as you might well imagine, or why their stuff isn’t organised. In the early days she was afraid to be herself because she thought there was a way of being “business-y” and the idea that you have to personify business to get business. So I told her “I think it’s going to be better if you just let your freak flag fly. You’re slightly grumpy and a little bit cynical – I don’t think I’d be trying to hide that. Just let it show. People are gonna like you or they aren’t. Hiding behind the facade is just making more work for you and the client can tell that there’s something off even if they don’t know what it is”. So over the years she has allowed herself to drop that facade more and more and, go figure, the more she does that, the more freedom she feels and the better the business does. 

The more you can be yourself in a fully authentic way, the more clients you are going to attract and you’re going to feel more expansive. You know, there’s a reason I have a Star Wars lunchbox right here on my shelf – it’s part of my freak flag. I also have a ridiculous amount of coaching books and my boots because I’m from Texas, so why not? Those are the reasons why people want to do business with you. Otherwise they would just go do business with some generic other person.

SC: Thanks so much for talking with us today, Kristine! 

I appreciated being here!

This piece is part of Startup Canada’s wider campaign in part with the U.S. Embassy in Canada to celebrate and honour incredible women entrepreneurs from both sides of the border. If you are a woman-identifying founder in Canada or the United States looking for free one-on-one advisory support from expert mentors, private sector partners, or startup support organisations, head over to to learn more and get started today.