Syama Bunten
Women don’t talk about money the way we should. Not honestly, not openly, and not with each other. But that’s changing. I’m Syama Bunten, founder of Wealth Catalyst. And Getting Rich Together is where the conversation lives. Every week, a different woman, a different path, and a conversation that will change how you think about your own financial power. This community is growing and you belong in it.

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I am here today with the brilliant Heather Kernahan. And Heather, what I think I love just the most about who you are in this moment of your life is you stand in the midst of incredible transformation. You are now the CEO of the Content Bureau, a company you’ve acquired, which is so cool. You’re a board chair, you’re the author of Unstuckable, you’re a global tech and marketing leader. And my love, you have advised some of the most innovative companies in the world, led global teams. And really, I feel like this is your new moment. This is the moment where Heather is coming out in version 10.0 to take over the world. And I’m so thrilled to be with you here today. Welcome to Getting Rich Together.

Heather Kernahan
My God, who the hell is that? Right? I’m ready. I’m ready to talk. I’m so excited to be here. You know I’m a huge fan. I’ve heard so many stories that you’ve shared and I’m excited to share mine.

Syama Bunten
You know, you sit in front of me wearing this beautiful shade of green with this beautiful pattern. Your hair is so pretty. I never do these things on video, but sometimes I wish people could see because the ladies, they bring mad style. I’m excited for this hour together. But before we jump into what you’re wearing and where you’re going after this, let’s start with a little girl, Heather.

Let’s start with a little girl somewhere between the ages of ten and twelve years old. Where were you in this beautiful world? Were you always wearing fabulous clothes? Was it pigtails, ponytails? Spill the tea, my love. What was life like?

Heather Kernahan
Oh my goodness. No, I was not always a good dresser. I will say that. And I’m gonna start with I’m Canadian, which I’m very proud of. I grew up in Canada, in eastern Canada, in a province called Nova Scotia, in a very small town. By the time I was 10, my mom had been remarried. She and my dad split when I was really little. I was one or two. And she was remarried and having two little girls who were my little sisters.

And so I was really learning responsibility as a big sister. I’m pretty sure when I was 10, I got my first job, which was a paper route. And I grew up in a family that was just busy with these two little kids. And I had a lot of responsibility in my family to help look after them and help my stepdad and my mom. I didn’t think too much about much. I just kind of helped out with my sisters and had fun with my friends.

Syama Bunten
I love that. Did the responsibility dawn on you at the time? Were your friends also highly responsible ten-year-olds? Or were you like, man, I gotta go do this thing, but I really wanna go to the park or hang out? What sort of responsibilities were you feeling into?

Heather Kernahan
Yeah. At that time I didn’t really know how much responsibility I had. It was just part of being the family. And it was my mom and I for a long time because she was divorced so young and it was a long time before she met my stepdad. So I remember being even smaller, four and five, going to help my mom clean offices. We really grew up with not very much in that period of time. My mom was re-establishing herself independently. It was the seventies. So there in Canada at least there was no requirement for a husband to pay child support. So no support at all.

From a very young age, I was always helping my mom. That was the job that I had in the family. And I loved it. She’s the hero of my story. And we just did everything together. So when my sisters came along, it was like, I need help now. It was only when I got to probably 17 or 18 that I was like, wait a second. I don’t wanna pick these little sisters up from school. I wanna go to the football game and do things that my other friends are doing. And at that point we had a conversation and she said, okay, I’ll figure out a different solution so you don’t have to look after your sisters all the time.

Syama Bunten
Wow, you know, I feel like at that age of ten and twelve years old, it’s like when little girls have the fake babies, and we’re obsessed. And so instead of the fake baby, you had the real babies. And you know what’s so funny is I myself and my sister are 12 years apart. And so it is also like there’s this point where you’re like, this is cool, and then there’s another point where you’re like, wait a second, I’m not the mom. Right. This is different.

Heather Kernahan
I would need to shed some of this responsibility. Yeah, they were my sidekicks. I took them everywhere for years. We did everything together until that point where I said, okay, I’m going to figure something else out here. I’m going to college soon. I need to get out of here and have my own life.

Syama Bunten
Yeah. So while you found yourself in high school, were you still able to work, make money on the side? Did you find yourself head deep into studying? What did you know of yourself in high school and who on earth did you think you would become?

Heather Kernahan
Oh my gosh. I did not like school at all. I was not a good student. I barely scraped by. I looked at some transcripts the other day from high school and there were lots of comments. “If she would only focus her attention, if she would only apply herself.” But I just didn’t like it because it didn’t feel real. But I always had jobs. Ever since cleaning with my mom and the paper route, I then went on to work at a restaurant, which I loved. I worked in retail, which I loved. So I really loved making money because that to me was a bit of freedom.

And at that point, I knew my dad. My dad lived about two hours away by plane. And my dad was very wealthy. So we’d have these very strange experiences in high school where my family, we were not poor, but money was always a concern. And then I’d go to my father’s home, which was huge and glamorous, and his life was glamorous, and I’d see something different. And then I’d come back to my home where I lived all the time. And so I had a sense early on that if I work, I can be safe, I can make money. And money could get me there someday, maybe where my father was. But I didn’t have a plan or know how to do it. I just knew to keep working, keep going to work, helping my family, and trying to progress and make more.

Syama Bunten
You know, it’s so interesting. It’s like you see this thing, you’re in proximity to it. And at that time, certainly the narrative I was told was you get a job and you keep it for 40 years. It’s like there’s this security of take the job, use the job, and retire at sixty-five. When you were in high school and you were working, where did you like to spend your money? Was it out with friends? Was it on food? Was it shopping? Were you a saver at all? How did you think about your money at that time?

Heather Kernahan
Yeah, I didn’t save anything. I spent it all. I would buy, I don’t know, it was the eighties. I remember buying nail polish in every neon color. And I remember buying whatever clothes I could afford because my stepdad and my mom couldn’t buy me the things I wanted. So I would just buy whatever I wanted. I’d go out with my friends. There was a fair bit of drinking in high school. I think I spent a lot on alcohol, and I do not recommend that, but there was a lot of that.

And just I spent it and I had a good time. And I’d save a lot of money to go to my dad’s because he lived in a big city. So I would go shopping in the city for things I couldn’t buy back in the small town I was growing up in. I just probably lived in the moment more than anything else. I didn’t know what a future could be. I was also so terrible at school that I just thought I don’t even know if I can get into college. So I knew at least I can keep working some kind of job. That was my thought during that period of time.

Syama Bunten
It was almost like working was the lifeline. If I can get a job, if I can show up, then I will be okay. I can take care of myself. That’s like a really young, independent streak, which I imagine served you very well.

Heather Kernahan
A lot of therapy. A lot of therapy.

Syama Bunten
Yeah, totally. These things serve us well until they don’t.

Heather Kernahan
Now I need to sit with this feeling I have all the time.

Syama Bunten
Oh my gosh. Okay. So you didn’t think that university was going to be possible for you. What were the dominoes that fell while you were getting ready to launch yourself, high school starting to wrap up? How did you start to put yourself out into the world?

Heather Kernahan
When I was in grade 11, which would be junior year in Canada, there was a program that was set up at my high school. It was an exchange program between an African country called the Gambia and Nova Scotia. It’s called the Nova Scotia Gambia Association. And this professor came and said, I’ve started this nonprofit, and what I’d like to do is take students from this high school to the Gambia and take Gambian students to this high school and do an exchange program and just open up the world to people living in Nova Scotia and the Gambia.

So I was immediately enthralled. And I went home to my mom and I said, I’ve met this guy, he’s doing a program, I want to do it. I just had this overwhelming feeling like I need to leave. I need to see the world. And I look back now and it was very detailed. There were months and months of fundraising. The families needed to get involved. My mom had to host the students from the Gambia to live with us for months. And so she made this all happen with me, including something quite incredible, because she couldn’t pay the fee that I needed to pay to be able to participate. So I worked at a restaurant and she said to the owners of the restaurant, can I come work there, open shifts, and I will clock in under Heather’s card so that she’ll get all the paycheck? And can I do that for the next six months so that we can boost her paycheck and she can afford to pay?

So she made it happen. So I tell you all this because I did the whole program. It was transformational. And I decided I want to go to college and I want to study international development and political science. I had been to Africa. I had done all kinds of programs there around education and sexual education training and just saw the world in a different way. I had been to London as part of the trip. So I felt if I just do a little bit better in my last year of high school, maybe I can scrape into some kind of college program around international relations. And that’s what I did. I was able to get in somewhere.

Syama Bunten
Hold up, wait a second. So you’re in a little town in Nova Scotia and you’re like, yeah, I’m gonna go to Gambia. So when you were there, and certainly London has a way of opening your eyes to lots of things, but while you were in Gambia and you had a chance to see the world maybe for the very first time outside of the infrastructure that you knew, what were some of the things that stuck with you all these years? What were some of the impressions you got?

Heather Kernahan
Well, we landed in London first. And I remember it was during, I think it was the Gulf War. So there were all these gigantic tanks outside of Heathrow Airport at that time. And I was just thinking, I am somewhere completely different. And how am I going to act? Do I retreat and stay in my hotel room, or do I go out? And I just went out. I was the youngest of the group too. So I felt a bit out of place. But I just said I’m just gonna go for it.

And then when we got to Gambia, I just wanted to be part of everything, participate in everything. And so I started to realize, gosh, I did all this work to get here. I saved this money. I made so many things happen. And that was a real awakening for me. I can make things happen. I can be here and I can meet lots of people and I can keep these people in my life for a long time. And this is just the start of something completely different. From a confidence perspective it really boosted me, as well as just my worldview. I don’t have to think about where I came from. I can think about the whole world as a place for me to be.

Syama Bunten
That is so incredible, Heather. Like, opening your eyes to a different world. You know, when I was younger, my mother is from the island of Mauritius. And I remember going to Mauritius and just seeing the world in such different ways, in ways that I don’t think I ever really fully could appreciate until I got older because of the differences of experience. And when you’re young and your mind is open, there’s just this absorption of life and of energy and of possibilities, which is such an incredible thing to experience. And what a gift to have your mother really stand by your side in such a rock solid way. So as you were getting yourself ready for university and preparing to enter, did you think you were gonna go the NGO route, go into humanities, become a political person and join an NGO? How did you think about university and what you would end up doing?

Heather Kernahan
Yes, I did think it would be the NGO route, because when I was in Gambia, they had all kinds of speakers come and meet with us. And I did meet a lot of women in particular who were part of aid organizations or rebuilding organizations or just all kinds of nonprofits who were living there and had lived all over the world. They were endlessly fascinating to me. They had these careers where they maybe moved every two years and they could just see things and it was their job to do that. So I thought I’ll study international development and then I will go into the field with an NGO. My dream job was being part of the United Nations, traveling around the world. That was the dream.

So I started down the path of doing that, and I spent a couple of years at college, and then I got an internship at an international peacekeeping center. Which gave me the chance to meet with people from all over the world who were working in the industry of peacekeeping, from governments to nonprofits to corporations. People would come to this peacekeeping center and train for peacekeeping missions. And it was at the end of my second year of college and I met a woman there who was really questioning me. She’s like, what’s your life like? What do you imagine it’s gonna be like? Do you wanna have kids? Do you wanna get married? And I had a boyfriend at that point. We’d been together for a while. And I said, I think I do. I want to get married. I want to have kids. And she said, then do not enter into this industry. You need to rethink everything right now.

But I still remember that conversation because it made me really think, probably at around 22, okay, what’s the next leg going to look like? And she just taught me so much about what you will likely have to give up if you go into this field and live this lifestyle. So it was a real reality check that I welcomed, even though I thought that was the path that I was on.

Syama Bunten
You know, it’s interesting because I could also have seen you say, well, this woman told me I’d have to give up all these things and I went, no way, I’m gonna have it all. I could have seen it going two ways, Heather.

Heather Kernahan
No, I didn’t. I’ve always done that. I’ve always looked at people that are doing things I am very interested in doing and deeply questioned them about what’s going on and really listened because they know a lot more than I do.

Syama Bunten
Okay, so this fabulous woman course corrects you, gets your head on straight. I wish all of us had someone like that in our lives. I wish when I was working in fashion, someone had told me, hey, do you want to make money? Don’t work in this industry. But not everyone tells you everything.

Heather Kernahan
I think she said that you will make no money. And I was thinking, gosh, I’m financing my whole education on student loans. How’s that gonna work?

Syama Bunten
Oh my God. I love that. Okay, so the wisdom came down to you. All of a sudden light bulbs went up. And then what happened? How did you start to navigate what was going to be next?

Heather Kernahan
I spent the next three years just messing around. I was, again, not a good student, even in college. I was working at the bar on campus, which was the best job in the whole world. And I just thought, I’ll just keep working at the bar and having fun. I’ll kind of go to class, but not really. I have no idea what any of this is gonna lead to. So again, like high school, I worked a lot and I made a half-hearted attempt with my education and really, really had no idea. And it was after senior year, well, I spent five years at college. I was having such a good time. And then I went back to London because I had loved it.

And when I was there, I just had no idea what to do. But I had seen this newspaper article about a new program being set up in my hometown that was a training program for public relations professionals. It said it’s a one-year certificate at the local community college, and you’ll be trained to be in public relations, which I had no idea what that was. So I read this whole article about every course and every description. And I just thought I loved the sound of all of it. Like every class sounded exactly like things I really loved. And I thought, I think I can do this. So I ended up applying for that program and was accepted while I was in London through the summer. And then I had been planning to stay in London for a while, but reverse course and came back to Canada to take that one-year diploma, which was the best idea ever.

Syama Bunten
Wow, that’s so wonderful. And you know, public relations is not easy. Everyone seems to think it’s easy, but it’s really not. I only did it for a year because I was like, this is too difficult. Most people don’t realize how hard it is. I think I realized it wasn’t for me when I was like, I have to go be friends with all these people I don’t want to be friends with.

Heather Kernahan
No thanks.

Syama Bunten
That is difficult. And it also takes a lot of chops. So after you received the certificate, was that really the jumping-off point? Did it set you on track to launching a career on the PR side?

Heather Kernahan
Exactly. And I’m a huge supporter and advocate for community colleges to this day. I spend a lot of energy and volunteer and I’m on some boards with community colleges because that community college experience gave me the technical skill and the capability to get a job. A job that would be a career. And that’s what I really needed help landing. That allowed me to take my first step into getting an actual salary, not an hourly rate, but my first salary. And it set me off on the whole career that I’ve developed since.

Syama Bunten
So incredible. That’s so incredible, Heather. So let’s start talking a little bit about career progression. In the beginning, PR like fashion, there’s not a lot of money. Luckily for you, you are smart in marketing and developed yourself in these strategic ways. But in the early part of a career, I feel like no one gets paid anything unless you’re in the legal route or the investment banking route or something to that degree. So as you were starting to build your young life, and you’re working and you’re figuring things out, did you have the wherewithal to negotiate for anything? Was it like, I’m just happy to have this job? Were there any sort of retirement things? How savvy were you in the early days?

Heather Kernahan
Not savvy at all. I was so grateful to have a salary. To me, I had made it. I think $30,000 a year was my first salary. And I just thought, I have made it. If I don’t make another dollar, this is amazing. I’ve got everything I need. But in the next two or three years, I serendipitously got a job in the tech industry. It was the late nineties. It was 98, 99. I landed in a tech company. And I remember when I signed the job offer, they gave me stock options. And I had literally no idea what this was at all. And then over time, people there explained it to me. And so I cut out a picture of a Porsche coupe and I put it on the fridge in my shitty little apartment that I could barely afford.

And I thought, I’m gonna get this someday. That’s when the hype was starting around the tech industry. Like you can cash out and you can sell an IPO. And I just thought I’m gonna make some real money here. Spoiler, I didn’t make any money at that place. But at least it got me into the language of what was going on in the technology industry. So I was making a decent salary with some potential upside, but I also was crushed by student loans at the same time because I had just been in college for five years. I’d taken student loans every year. Even though I’d worked a lot, I hadn’t saved anything. And so I was in a position where the student loan debt collector started calling me at my job. I was probably by that point two years into my career. And that really scared me. They said, if you do not make a payment, we are calling your employer and we’re gonna garnish your wages. It was terrifying. But it was the kick I needed to start focusing on getting my financial life together. Until that point I hadn’t even thought about it. I just knew I was in debt and I probably always would be.

Syama Bunten
That is so scary to feel sometimes. I think it’s like one thing when something happens to you and you feel like you can manage it, and then the moment it starts to impact other people, it’s like the other shoe drops. And it’s somewhat traumatic to be in this place where all these things are happening. And unfortunately, our financial systems for college students don’t actually tell anyone the implications of these loans. And so here you are, this young adult feeling this crisis of, you know, my whole life is gonna be over, I’m gonna lose my job, all because of some jerk face loan collector trying to intimidate you. It’s really awful.

Heather Kernahan
Oh my gosh, it definitely worked. But I called a friend who had a finance job in a bank and we were really good friends. And I cried my heart out to him about this call that had come in. And he said, okay, I’m gonna take you and we’re gonna set you up with a retirement account. In Canada it’s called an RRSP. It’s like a 401k. I said, did you not listen to me? I have no money. I owe so much money. Why would I ever open a retirement savings? And he said, we’re gonna put your financial future together.

And he took me to help me sign up for it. I think I put five dollars in every paycheck. And then he sat down with me and all my credit card bills and my student loan bills and taught me, okay, we’re gonna pay down the highest interest one first. And then you’re gonna take all the money you were paying on that bill, and you’re gonna double up and pay the next one. Core concepts I’d never learned before. So I’m very thankful to my friend Mark, who did that with me and started to help me get things together. That was the beginning of me figuring it out.

Syama Bunten
Amen to Mark. You know, also how brave and courageous of you to ask for help.

Heather Kernahan
Yeah, I was ugly crying.

Syama Bunten
But still, you know, I think the other layer of going through panic is isolation. And certainly back then it’s not like there were so many tools and resources available online. It’s like you’re only as good as the people who can counsel you and help you see things differently.

Heather Kernahan
Right. Yeah. And I didn’t grow up with any of that. So yes, I was very thankful. By that point I was living in Toronto, and I saw what was possible with people’s lives. I was looking ahead of me 10 years and seeing people with homes and families. And I had a feeling I can get there. But I have to do the work for it. And so I was willing to face it at that time. That did take a certain amount of courage to start figuring it out.

Syama Bunten
Okay, so let’s start talking about some professional inflection points. In the beginning, a lot of it is like, holy crap, life, how do I do this? And there’s a car payment, or this other thing, and it’s fast and furious and not always pleasant. And then there start to be some inflection points, whether that is career shifts or pivotal relationships in your life. What were some of these inflection points and were they correlated to working hard and getting paid more? Was it asking for a raise here? Did other things start to fall into place? What was the first pivotal inflection point?

Heather Kernahan
Well, the tech startup that I was with, the first one, they ended up selling to a much larger corporation. And the first few months that I was working there, I had a review at the end. And one inflection point was sitting down for that review with the two CEOs of the company. And they said to me in that meeting, we only want people here who want to be in the top 10% of their profession, and you’re not cutting it. You’re not operating in a top 10% way.

I said, can you give me examples? So they laid out six or seven aspects of my role where they felt I was failing. And one of them in particular said, I want you to go home and think about it over the weekend. A lot of people don’t want to operate at that level because it takes more than you’re giving. So if you don’t, just come back and let us know and we’ll help you exit the company. But if you do want to be at that top level, you’ve got to change pretty dramatically how you’re showing up. That was an inflection.

I didn’t know what any of this meant. I didn’t know what it meant to be a high performer. And so I just thought, I just need this job because I’ve just had this guy trying to collect my student loan from me. Now I’m not doing well, although I thought I was. And when I came back, I said, I really want to make this work. I want to be in the top 10%. So they gave me 30 days of Tony Robbins cassette tapes. And every day, one CEO said, listen to it every day, type me up some notes, and then come back and we’ll have a conversation about it.

And that 30 days of Tony Robbins helped me understand that I was fully responsible for my life. And it was that lesson that I needed to really charge my career up. Three months after that situation, they boosted my salary by $20,000. And I was not making a lot of money at the time. I completely changed how I showed up as a professional. And then when we sold the company to the next owners, it was a much larger organization and I was ready for that. So I just really worked hard from that moment forward. Come in early, stay late, do what it takes, work what you need to work to deliver in the way you need to deliver. That was a major inflection point.

Syama Bunten
How old were you when you were listening to these Tony Robbins tapes?

Heather Kernahan
It was twenty-six or twenty-seven.

Syama Bunten
You know, I think there’s something really unique when someone gets exposed to that type of thinking and language. And depending on how young you are, it can have like really exponential effects in positive and not positive ways. But I think there’s something interesting when you’re young and you have access to information in a way that other people don’t naturally. And I think like understanding that we are in control of our thoughts, of our realities, of how we do things, to me is the most important component. And the Tony Robbins messaging is very bold and big. It is very much the biggest version of that.

Heather Kernahan
Yes. And it was really shocking to me. It’s like if I am fully in charge of my life, I better do a good job of this. I can’t blame anybody else. It’s me. So that allowed me to leapfrog into a much bigger opportunity at another business that was a global technology company. And that job was an inflection point because I was able to travel. Somebody paid me to travel. I wasn’t working at an NGO. I was working in a corporation and they sent me all over the world. And it got me to California a lot, where I live now and ended up moving to.

Syama Bunten
That’s amazing. Okay, so obviously getting paid to travel is also a big deal when you’re young. I feel like everyone’s like, how do I see the world and not have to pay for it? So to have that early exposure to seeing the world was incredible. At what point did you start to feel things are materially changing for you? So a $20,000 bump is certainly like breathing, right? At that age, it’s like I can finally do something more significant than I thought I could. When did you start to realize I can go beyond breathing comfortably? What did you start to do with your resources?

Heather Kernahan
Well, when I got the $20,000 bump, my boyfriend, who I had met in my last year of high school, we were still together and we had been talking about getting married. So I thought for the first time, I’m gonna be able to pay my student loans on time and we can plan for a wedding now. I thought all my friends were getting married. We’d been together a long time. I really wanted to marry him. So that’s what we started to put money away for at that time.

And then it was simple things. In the beginning, we ate out more. We could go to a concert in Toronto. We could travel to the US and maybe do a holiday. So we started to spend a little more money on those kinds of luxuries, which felt really nice. And I just thought, I want more of this. And I know how to get more of this. I’ve got to work for this. So I’m going to work incredibly hard. I’ve got to invest in my professional development, which was the Tony effect in my life. I constantly developed myself and my thinking because I knew that I could just do bigger and bigger things if I could keep working on that.

Syama Bunten
I love that. What were some of the tools or resources that you were referencing at those times?

Heather Kernahan
Every kind of book that I could get on professional development and self development. Somebody gave me Jack Canfield’s book, How to Get From Where You Are to Where You Want to Be. Have you ever read that one? That was transformational. And then I did something kind of geeky. Every city and country I went to, I would try to find a copy of the book. I have so many copies in my house because everywhere I went, I would buy a copy. That book gave me the guide to how to get from where I am to where I want to be and helped me develop the vision about where I did want to be, because I had operated for so long without looking into the future too far because I didn’t feel equipped to do that.

But then I started to really write things down. I’d moved to this global technology company, still in Toronto. I was traveling to all these great cities and reading books like that. And I started to think, okay, I want to do my MBA. I was a terrible student, but if I want to really excel, I’ve got to do things like that in my life. So we started planning, writing down my goals, breaking down the goals, and just continuously working on myself.

Syama Bunten
Wow, it’s like this constant state of overcoming oneself.

Heather Kernahan
I still have to do that every morning.

Syama Bunten
Yeah, no joke. Okay, so you go and get your MBA. Love it, hate it. Was it good for you? What was the vibe?

Heather Kernahan
Yes, yes. Everything that I wanted. Well, I went from Toronto to San Francisco. And it was when I landed in San Francisco that I signed up to do my MBA because I was at a bigger global technology company. And seeing our CMO and how he operated, I just thought I want to be in the room where decisions are made with the CEO. And when I deconstructed what executives have in their background to get them where they are, it was an MBA. So I went to Dominican College in San Rafael, which is where I live now.

And started the process of doing the MBA, which took about six years. For me, it was worth it. I still use the tools from the MBA today. I didn’t love the process of it because I was working full-time and working overtime a lot and going to school on the weekends. And by this point, I had a little girl. I got pregnant with my son the first semester after I started my MBA. So there was a whole lot going on.

Syama Bunten
Oh my God, Heather.

Heather Kernahan
It was insanity. I look back now and think, what was I doing? But I will tell you, my husband and I made a foundational decision when we decided to have kids. Because we had moved to California shortly after we had our daughter. And he couldn’t work here. He didn’t have a visa. I had a work visa. And we decided he’s gonna stay home and be a stay-at-home dad, and that’s gonna be his career for the next two years plus.

And he was so happy about it and I was so happy about it because I could really then lean into work in a way that I would probably have been challenged to if he had a job that was similar to mine. And so that gave me extra time really to do the MBA and the job and the kids and all of it because he was at home looking after everything there.

Syama Bunten
I mean, you guys were having a really progressive conversation at a time when I’m sure you were one of few friends who were setting up their lives like that.

Heather Kernahan
Right. Yeah. And nobody understood it. Certainly neither of our families understood it. And lots of questions from them about why are you doing this? Why don’t you stay home? Why doesn’t he go to work? Wouldn’t you be happier if you did that? Lots of judgment around it. But from a values standpoint, together we knew that this is working for us and we’re just gonna keep going and doing it.

Syama Bunten
It’s really powerful. And there’s so much strength in that. I think that a big part of satisfaction of life is listening to what’s right for you and following that despite what other people might think or feel or say. And what was it like for him? As a woman who’s stepping into the forefront, into fuller expression of an identity that you’re also working so hard to define. For you, it was very much doors open, elevate, go. Also a lot of pressure, but go flourish. Did he communicate how he was experiencing all this flourishing in a way that was deeply different than what someone would typically expect?

Heather Kernahan
Yeah, it changed through the years. So when we first got to California, our daughter was just one. And he had to adjust because in Toronto we had friends and family around. And then being in California, we didn’t have anyone we knew. So he had to go out and establish himself and relationships. And he used to come home and say, once again, the only dad at the playground, or once again, the only dad at the playgroup. And I think he struggled a bit with loneliness during that period of time.

But he would always say as I left every morning, he’d say, you go get it out there. I got it in here. And I think he took a lot of pride in owning that role within the family and knowing that we were really co-pilots together. And he was always saying, what’s next for you? Or if I had my MBA all weekend, he’d say, what do you need me to get ready for you? What do you need for Monday? I know you get that tired after going to school all weekend. Laundry, dry cleaning, dinner, whatever it is, I’ll get things lined up for you to help make it easier. He felt like his role was facilitating where I was gonna go because he could see I was opening up and saying, okay, holy cow world, look out. I’m gonna get this master’s. I don’t know what’s next after that, but it’s gonna be good and I’m gonna go get it.

Syama Bunten
You know, it’s so beautiful and wonderful to hear how he was experiencing that with you because I think there’s something that’s a real gift when you have a couple in partnership who are so transparent with each other. It’s like a forced bond, but it’s also like a forced vision. Because if you’re financially very interdependent, then it really forces the conversations around what’s important, what do we want, how do we talk about these things at home. It’s so different than two different income producers who are like, I’ll handle these bills, you handle those bills, but no one knows what else is going on from a financial standpoint. When things are interdependent in that way, I think it forces important and necessary and valuable conversations, and also the ability to really be present for each other.

Heather Kernahan
And a lot of compromise too around money. I remember during that period of time, people would say to me, you’re so lucky, your husband will stay home. Now part of it was forced because he didn’t have a work visa. But also it was a decision we made that we were going to operate on one income. Come to California, operate on one income for a while. Let’s do it for two years and just see how things go. And then when we extended, it ended up being six or eight years before he could get a work visa.

And we had to keep making that choice over and over again. So we didn’t do fancy vacations. We didn’t own a home when we first moved here. We still had our place in Canada. But those were financial decisions that were a compromise and probably set us back from a retirement standpoint and some of the long-term investments that we could have been making during that period. But I look at it now and say it was worth it because it did allow me to build up my experience and my education. And so I was able to catapult a bit later in my career, once I got into my forties. Then I could really make leaps around things like equity and salary and things that could get us in the position we’re in today.

Syama Bunten
Also, what a wonderful gift for your children. Oh my god.

Heather Kernahan
Yes. I have to tell you, I feel like it is one of the gifts I gave myself, having chosen a partner who, because my dad wasn’t there for me, is a hundred and fifty percent there for our children and was the primary caregiver. The relationship that they have. Like that’s been a healing gift for me in my life. I feel very proud of him.

Syama Bunten
That is so beautiful. Okay. So you started talking about making big moves, getting into equity. Heather’s rising the ranks. Let’s talk about some of the bigger opportunities that would come your way and how you started to navigate what these larger roles were and what are some of the ways in which you went about securing your financial outcomes and ensuring that the time you spent going slow and steady now allows you to go fast and get the thing you want.

Heather Kernahan
Yes. Well, when we moved here, I talked about being with a global tech company. And that gave me experience with the employee stock purchase program, which I did participate in. I took advantage of everything. So anyone who’s in a corporation with those types of programs, take advantage of them because there is a return, even if you cash your employee stock purchase out right away. At the end of every quarter, I’d cash in my ESPP, make 15% on what I’d saved, immediately have it, and then be able to decide what to do next.

Syama Bunten
Thanks, Mark, again. You know, it’s like Mark keeps showing up. All right, keep going.

Heather Kernahan
Yeah, he sure did. He helped me with all those things. And then I had stock options and RSUs when I was at that big tech company. So I started to realize what incentive packages could look like being part of a public company. I never negotiated during my time there, and I don’t think it was on my radar that I could. I didn’t understand that I could. But then I left and I went to a pre-IPO startup. And then I was able to negotiate a package that had a much richer upside on the stock when we went IPO. And my salary was lower than it had been. So I had to sort of take a deep breath around a lower salary, but better compensation if the stock did well. And we did IPO, which was great.

There was so much I didn’t understand or questions I didn’t know to ask, going into a pre-IPO company, about what the equity looks like across the board and who all the investors are and what happens if we do a first stock split, and what does that mean? There are just so many things I didn’t think to ask, but I learned a lot. I really learned a lot. And to go through that process, I was a director of marketing inside a business, working with the executive team. I got board experience in that job. I got to go in and present to the board. I was elevating the language of business that I had. And I had almost done my MBA at that time.

And then after the IPO, I’d only stayed for about a year. And it was the last leg of my MBA. I was doing a finance class and the professor was saying something about, hey, when you’re CEO of a company, here are some things you should look at in the financials. And I was wanting to be a chief marketing officer. And I said, well, I’m gonna be the chief marketing officer, what should I do? And he said, Heather, you are not thinking big enough.

And I said, what do you mean? And he said, you are being trained to be a chief executive officer. You need to think about running a whole company, not a function of a company. And that was a lightning bolt for me. I left and I just thought, I could not only be the right hand of the person in charge. I could be the person in charge of it all. Then I was like, I can’t go back now to not think about that. I went home and I said, I have to be a CEO.

Syama Bunten
Yeah.

Heather Kernahan
My husband was like, what the hell happened at school today? I was like, I just learned I could run everything. And that’s what this is all about. And so then it was like, what am I going to run? How am I going to get that experience? And I ended up going and meeting with a woman who had a public relations and communications agency in tech. And she said to me, what do you want to do next? And I said, I want to be running a whole company. And she said, come work for me and I’ll teach you how to run a whole company. I’ll give you the experience. Come be by my side and I will teach you how to do it.

So that was my foray into okay, now I’m on a track. I’m in consulting in the technology industry still, and being able to really build into a CEO job. We ended up selling that company to Hotwire, where I worked for a long time. I worked for 10 years. So I was part of building that brand, meeting with potential acquirers, figuring out how do you do a deal, how do you sell a business, and how do you evaluate who’s going to buy you. And then we sold, and it was very successful financially for me. And then I could really breathe. Then I was like, I have the kids’ college paid for. And having suffered with student loans, my number one goal with the kids is I just want to have school paid for for them. And when I was able to do that, I was like, okay, now what next?

Syama Bunten
You know, it’s interesting to think about the moments that allow us to breathe. And it’s always part of this journey or this healing from our past, this thing that we no longer want to feel anymore, or this ability to create. And I am so certain that your children have had a very different life than you had growing up. They’ll never know probably what it was like for you. And unfortunately kids will have their own experiences, but it won’t be yours.

Heather Kernahan
Yes, they will have their own. That’s right. That’s probably a whole different conversation around whether that is the right thing to do. I was definitely providing a life for the kids I didn’t have. And I still want them to have grit. And I still want them to have ambition. I want all of them to have all those things too. Those are really good things.

Syama Bunten
Wow. And so when you had this incredible financial moment, what were some of the thoughts going through your mind? Was it, let me stock up the 529s and get this going? What were some of the other boxes that you felt you needed to check off in order to be a good steward of this event that happened to you?

Heather Kernahan
Financial advisor was first. I got serious about that and selected a financial advisor who could sit down with us and really look at the future 30, 40 years out and talk about what this is gonna look like and then be responsible with putting the money in all the right places. How much are we gonna put into investments? Even things like our home. Are we gonna invest in our home? How much money do we wanna put towards that? And just thinking about the lifestyle that we want to have. So the financial advisor helped us a lot, really plan that out. And then the kids’ education.

And then really pretty quickly, I turned to some fun money because something I really wanted to do for a long time was to start being a venture capital investor. And I had been studying different Silicon Valley firms and how do you become a venture investor? I had no idea in the beginning how much money you need to put in. And then I had enough to be able to invest some money there. So that was my fun time. I was like, I’m gonna be a VC now and I’m gonna become a limited partner in a fund. And I actually know what that means now. And I’m gonna go have that experience and kind of help put money into the next wave of innovation in the tech industry, which has been so important to me. So that was one of the early things I did.

Syama Bunten
I mean, some people are like, yeah, I’m gonna buy the sports car, and you’re like, I’m gonna be an LP. That’s not on everyone’s top of mind. How did you figure out the processes to become a venture capital investor, to become an LP? You know, these days there are so many funds, so many people are raising against so many incredible theses around what they want to create in this world. How did you narrow down becoming an LP and for whom? And what did it feel like to write that check? Cause I think it’s like a feeling.

Heather Kernahan
Yeah, it is a vibe for sure. Well, I had been working with a few startup founders as part of the consulting business I was with. And so I was always meeting their investors and asking questions and trying to dig into it. During that period, it was 2017-18, there were some firms that were coming up that were really focused on investing in female founders and minority founders. That was of deep interest to me.

So I looked more into those funds and I thought this is values aligned and this is where I want to be investing when I can do it. And I just did introduction calls with them. And one of the first questions was, how much is the minimum to come in as an LP? And so I got the real information. And I think that’s part of it sometimes in demystifying areas where you’re not sure what’s going on. Just ask a lot of questions. And I always felt, maybe because I was Canadian and coming to the States was a totally different environment for me, I leaned into that. I would say, well, I grew up in Canada, so I don’t understand the situation here. Can you explain to me what it’s like? And people would very willingly share information, which I love about the tech industry. They’ll share.

And then I understood, okay, I need this much money to get in as an LP, and here are the experiences and benefits of being part of that community. And I had two or three options that I had narrowed in on. And I was just waiting. I thought when I save enough, or I have enough, or this acquisition goes through, I know which one I’m gonna pick first.

Syama Bunten
That’s so fun, I think, to think about that moment where you start to think beyond yourself and about what the world is that you can actively create with your capital, with your time, with your energy. Like it’s a really powerful stance to have, which is, I’m now thinking bigger, broader, even beyond owning a company. Now you’re participating in like the actual development of economies and of industry when you choose to invest as a venture capitalist. So this year, you’ve had some incredible transitional changes. You’ve stepped into what I think is something that you’re going to love and keep doing over and over again, which is starting to build your own private equity firm, buying businesses, thinking about creating once again a step above. But certainly buying businesses and being the owner of a company is not as safe and secure as working for a big company. So talk to me a little bit about when you knew you were going to become an owner and when you knew you were going to be making this sort of transition.

Heather Kernahan
I had been watching people in my network for probably the past five or six years. People who had made the leap and had started their own companies or bought companies or were buying and selling companies. They were entrepreneurs and they were doing it, good and bad. And I was watching them, talking to them about it, reading stories endlessly about people who had made that leap. And I always thought, I don’t know if I have the confidence to do it. And then I thought about, well, what would it take for me to have the confidence to do it? And really it came down to money at the end of the day. I felt my skills were there. I’d been running businesses. I knew how to do that. But I had sort of avoided looking at, okay, what are the real financials about what it would take for me to do it? And then when I got comfortable with that, writing down, okay, how much money would we need to operate on as a family for a year if I started a business and we had no income? I was doing that work to understand it. And then I got to a place financially where I said, okay, I’ve hit the numbers that I felt like I needed to be able to make the leap.

I didn’t expect to buy a company. I thought I would go out and start something new. However, I had been a client of this company a long time ago. And when the owner called and said, I’m gonna move on to my next thing and I’m gonna sell the business, do you want to buy it? And I said, you want me to buy it? Which was so funny because during my tenures at the consulting firm, I had led three acquisitions of businesses. I had been part of selling a business. I really knew this space. But suddenly when it was my money, different situation. Like my real money? Buy what? With what? How?

So when my panic brain calmed down, I thought, I know all the mechanics of making this happen. I know the good stories and the bad stories around acquisitions. I just need to figure out the money piece. And that’s where the financial advisors came in very helpfully. I called and said, I have a wild idea of something I want to do. What do you think? And they said, well, there’s three different ways you can do it. And they took me through each option with the pros and cons. And I sat with that and then after looking at the options, one was very clear to me, which is putting our money into it, personally financing this whole thing, and really looking myself in the mirror and saying, Heather, do you believe in yourself enough to do this? Your money, your actual money is on the line. And I said, I do. I don’t know what it is, I do. I’m gonna go do it. So I bought the business, which is the first acquisition. And the dream is to go on and do many more acquisitions and really help other founders build their businesses as part of a community of companies.

Syama Bunten
I mean, it’s so amazing. You have this wonderful corporate success, you keep pushing yourself to see what’s bigger, and you keep growing into those spaces. It’s like every time you put something out there, things seem to deliver. Right? You just don’t know how.

Heather Kernahan
Don’t know which way it’s gonna show up, but it shows up. I’m in it now, a few months into it and really excited, happy that I made the change. And I wake up every morning and I don’t feel panicked or worried, even with everything going on in the world. I just have to say to myself every morning, I believe in my ability to do this and I’m gonna make this work. I’m gonna make it work. I can.

Syama Bunten
You know, I hope your close friends and loved ones tell you this, but girlfriend, I’m proud of you. I am proud of you. You’re doing it.

Heather Kernahan
Yes. Thought about it for a long time. Long, long time. And now I am doing it. Yes.

Syama Bunten
I love that so much. So I feel like if I talk to you in two years, it’s gonna be like, and then there’s like three more businesses and then this thing. And so I’m grateful to know you and to be your friend and to sort of see these evolutions of your incredible life. And speaking of evolutions, I do believe that we are all gonna be living to our early 100s and that’s gonna become the new norm. And it feels to me like your life has been full of possibility and expression and intentional design. But I’m curious to know, as you sit back and look at your life from this vantage point of 104, what is the legacy or the life body of work that you see, Heather, that you have created? What is the fingerprint or the stardust that will be left on this planet for you?

Heather Kernahan
Well, I hope I’m still working till then. When I left my corporate job, I had so many people email and say, are you retiring? Like, retiring? No, that sounds horrible. I’m just getting started. I really want to keep the possibilities open forever. And I think there’s always gonna be something interesting to do. So I really do hope that I have some varied career up until I’m a hundred and four.

And with the business I have today and what I wanna do in the future and all the people I’ve worked with in the past, I’ve always wanted to help others see that there’s something in them that they can unlock to that level for themselves. And so I really want people to say, she helped me see something I couldn’t see in myself, or she gave me an idea that led me to the next big thing in my life, she helped me see more than I could see myself. And if people say that about me, I’m so very grateful for a life well lived. I think that would be great.

Syama Bunten
I mean, Heather, it’s just the story of your life today. It’s shown so much possibility. And the power of speaking the things you want into the world. We talked a lot about money and earning it and different ways we can invest it and all of that. And certainly money is also really fun and enjoyable. And you demonstrated that when you were in high school and college. It was like, I’m gonna make this money and I’m gonna have a good time. I would love to know now, thinking about all the ways in which you spend your money, what has been one of your most favorite recent ways in which you’ve spent your money?

Heather Kernahan
I have bought, a few years in a row, a subscription to Inspirato, which is a travel service company. Do you know them?

Syama Bunten
No, what a pro tip. Spill the tea.

Heather Kernahan
Okay. Inspirato, you pay an annual membership fee and they have different memberships you can buy. But one of the memberships is you can have unlimited high-end hotel stays as part of your membership. They have, I don’t know, eight hundred thousand properties around the world. You book, you stay, you don’t pay anything when you’re at the hotel. It’s part of your subscription package. And then as soon as you check out, you can book your next stay at the next hotel. That has been a luxury beyond luxuries and a real gift that I gave myself and gave my family, to spend some of our hard-earned money on travel and experiences, which I think are the best way to spend money.

Syama Bunten
I am totally googling this after. Oh my God. This is so fabulous. Inspirato. Okay. Got it. And then my last question for you is, you know, everyone who’s on the show, the women who listen, and there are men as well, but what we are really known for is rallying around incredible, powerful women who are up to big things in the world. What is it you’re calling in right now? How can we support you? What do you need? More people to do business with? What is it that you are needing right now and how can we support you?

Heather Kernahan
I’ve got two. One is a business ask. So I’ve acquired this business, the Content Bureau. We are B2B content marketing, and I am looking for more clients who need a great content marketing agency partner as they go into 2026. So new clients in the B2B space. That’s what I’m looking for. My second one is more about my heart. I really would love to talk to anyone who’s looking to up-level their own thought leadership platform in 2026, executive women especially. I tend to speak about this topic a lot because what I get to do here, and what your other guests get to do, is tell our stories on big platforms. And many people limit their thinking about what’s possible in telling their stories. So anyone who wants a little kick in the butt around that, send me an email.

Syama Bunten
Oh my God, Heather, you got it. Done and done. Let’s get rich together. Let’s make tons of money. Have all the clients come in.

Heather Kernahan
Yep. Build our businesses. Help each other. Support each other. All of it.

Syama Bunten
Heather, it’s been an absolute gift and treasure to have you here today on the show. Thank you for your spirit, your kindness, your generosity, for living the biggest, fullest life that you can. You stand as an inspiration to so many. Thank you for being here.

Heather Kernahan
Thank you. Thank you.

Syama Bunten
Thank you for listening. This is the conversation we come back to every single week. Real women, real wealth, and what becomes possible when we stop being silent about money. If today’s episode moved you, don’t let it stop here. Wealth Catalyst is where women go to take it further. Our Freedom Tour salons are gathering women in 32 cities this year. Intimate evenings in homes and private spaces where women talk honestly about money, risk, and what they’re building.

And if you’re ready to go even bigger, join us at the Wealth Catalyst Summit, a full-day event in San Francisco this October. Find your city and claim your seat at wealthcatalyst.com. We’ll see you there.