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On approaching the founder journey with our whole selves with Kirk Fernandes
Meet Kirk Fernandes, Founder of Merit—where tech workers find mentors, get career advice, and connect with the best companies to grow their careers for free.
Meet Kirk Fernandes, Founder of Merit—where tech workers find mentors, get career advice, and connect with the best companies to grow their careers for free. Kirk shares his journey and inspiration for starting Merit and how he incorporates his whole self into his role as a founder. We deep dive into Kirk’s interpretation of work-life balance, which he defines as spanning over a long period of time through investments in relationships and rejuvenation. He also offers a simple framework of how he keeps himself and others close to him accountable for the overall health of his company, physical self, and relationships with others. Ultimately, he offers not advice but his own experience to inspire you to make informed decisions for yourself, whether or not you're a founder.
Interviewed in June 2023
Heads up, the interview contains some explicit language that may not be suitable for all audiences. This conversation has been edited for clarity and brevity.
Tell us about you and what you'd like the audience to know. I'm Kirk. I'm the Founder of Merit, a mentorship to sponsorship platform for the under-networked tech worker. I'm a Canadian who spent his life working in America in big tech like Microsoft and startups like Hightower and VTS.
The thing I'm most passionate about building is great products and great teams. And now, at Merit, I'm focused on building great brands and understanding the marketing side. Merit is a thesis on my view of a tech career. Merit's been the final stage, or the Ph.D. of my career, if you think of it that way.
Let's rewind a bit—what led you to want to pursue creating Merit? I went to the University of Waterloo, which has a co-op program. They have all these relationships with companies, and you do internships every three or four months. That program in Waterloo got me my first job at Microsoft. Microsoft set me up to come to New York and work at Hightower. Hightower got me into VTS, and many people I worked with in VTS became early users and investors in Merit. So, I had this initial kernel of a network bootstrapped by Waterloo. And I realized that my whole career can be traced back to all these people, and this network keeps expanding.
To me, Merit would be this mentorship platform that essentially hacks a network for the tech worker. Going deeper into the industry, I've learned that the vast majority of people entering tech are under-networked. They don't live in a major tech hub in this remote world. A lot of them are coming from boot camps and state colleges. They're not coming from [University of] Waterloo, and a huge chunk of them are from an underrepresented group, like being a woman or person of color. The vast majority of tech actually experiences this problem. So, Merit is the solution to the hypothesis that networks grow careers, but most people are under-networked.
While Merit is at its current state, it's not the end state. Were there any particular moments leading up to Merit where you found the flip side of not having a network was like? Yes, when I was managing a team at VTS, it was a big product management team with six very diverse people—ethnically, gender, and background-wise. Often, they would have very particular questions like "How do I negotiate this raise?" and I would give my advice from my perspective as a man, but I'm also like, "You should talk to women. There are nuances of how you ask for raises as a woman." So I would be like, "There's someone I know who is more senior; you should talk to them."
And then I realized if I wasn't there to facilitate that connection, like, what would happen? Are we just going to depend on a random chance network of your manager if your manager is willing to do it? I saw how much I was not just the enabler but also the blocker of some of my team's growth. So I was like, "Why leave it up to chance and the manager?"
When I started Merit, it was actually like, I wish I could have given this tool to me as a manager because a lot of times, my reports had questions that I didn't have the answers to or network to get to. Even my own network came up kind of limited. From the very personal point of view where I was managing under-networked people, it was a very limiting function. Merit is similar to my network but at scale. Why depend on just me? Why not depend on 8,000+ people?
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Were there any moments you found you needed somebody, like a mentor, as you navigated your role as a manager to now actively building Merit? Every day. I use Merit to build Merit. It's about making it more socially acceptable for people to ask for help. That's the hard problem on the mentee side. So practically, not only are Randy [Brown] (Merit founder) and our team mentors on the platform, but they are also mentees. When we have an issue, we go through the index and find people to talk to.
We use the platform every day, and I would say people don't use it enough. But, the more senior you get, it's a little bit harder to ask for help because the questions become so specific, and fewer people can theoretically help you. But there are always people that can help you.
So, for me, I've been using Merit to build Merit. And, the way we've capitalized our company, we have a community of investors. We have tons of people that we tap into every month to ask for help. It takes a village to build a company, and we literally have a village of people.
As a founder, what are some of the hardest things you've had to ask for help? You mentioned that it's tough, especially as you get more senior. I think of being a founder as almost niché. Investors are very specific because you can ask for intros for feedback and give advice on very tactical things.
The really hard problems and scary stuff as a founder is when things aren't working, and you don't know what to do since you've never done it before. Some investors usually have been founders before, like Gary Chou or Donald DeSantis, who we talk to. They understand, and there's a level of empathy.
Ultimately, I have a peer group of founders who are just friends. And we hang out more casually or in the group chat. And that's something where you can be a little more honest about how chaotic, scary, weird, and how made up all of it is. Because you can't really be that honest to your team and investors because you want to project a level of confidence to show that you know what you're doing. But sometimes, you don't know what you're doing and make it up as you go along. You just have to be right, eventually.
I always tell other founders that I learn the most by talking to other founders at my stage or the stage ahead in terms of actually debugging your company and being better as a founder. An investor has a very specific relationship where you're trying to make them money, and employees work for you. You're in between them and their paycheck. So you're not always going to get that level of honesty versus someone who is just a founder who would let you know when something you should do or not do more honestly. The founder peer group is where I found the most learning, and I've just been lucky to have a lot of founders in my orbit.
What is the day-to-day like as a founder? Day-to-day, it's very different. For example, today, I have an interview with you, a team retro, two pitches, and a coffee catch-up. It's going to be a ton of emails. Today's not a super interesting day. laughing
But some days, it's like planning an event, or it's going deep on the product. Some days, it's focus on teammates who might not be doing so well and need to do active coaching. So it really depends.
But the high-level job of the founder is to essentially define a mission with a high-level goal and metrics.
And, essentially, don't run out of money. So, like selling to investors and customers and then hiring and managing the team. Those are three of the responsibilities that'll always be true.
I kind of view it a little bit more like the metaphor of a firefighter. When there's not a fire, you're in the firehouse cleaning, making things better, and working on the next version of the company. But, when there's a fire, you have to go put out the fire. Right now, my number one thing is fundraising. So, until fundraising is done, I can't go back and work on the next version of the company. The metaphor [of being a firefighter] is a little bit better than another metaphor that some people talk about the CEO as a salesperson.
Right, I hope you're currently in the firehouse, and that's why you're having this conversation with me with no fires burning outside! Yes! Maybe right now, it's like a low simmer. But today, there are no fires right now.
Also, being a founder is so subjective. It depends on the company, the stage, and your personality. And we have co-founders. Like Randy, my co-founder has responsibilities that are more on research and development to keep building the product. My responsibility is more on marketing and money, including understanding sales and capitalization. So you divide and conquer—it's rarely just one person. It's a very unique situation, and it's what you make of it. The key responsibilities are true from start to end game—it just changes.
Could you share some of the highs of being a founder and maybe some of the lows? The highs are like, "Oh, this is working!" It's when it's obviously working, and people are getting a lot of value out of the platform. Or, we closed the sale we got from four customers to 10. Or that we recently crossed over 7,000+ users. Or that we have really cool designs, and we're going to ship it. And there's a new teammate that just joined, and they're doing a great job. Or unsolicited feedback that goes viral on Linkedin. So those are the high highs.
The lows are just as numerous. It could be that the website goes down or someone has a really bad experience on the platform. The lows could be you pitch 10 people, and they all say no. The lows could be that a teammate's not working out. A low could be you just forgot to do something. The lows could be that a competitor launches something slightly better than what you were building, and you have to rejigger your plans, right? The lows can be numerous.
What I've learned is that as you go deeper, you can't make the lows any lower. You actually care more the deeper you go into it. So all you can do is make the highs higher. laughing Like you can't avoid disappointment. It's like a roller coaster—you can't be upset when it goes up because it'll also go down, right? It's the same concept, so you must embrace that. [Being a founder] is not a steady journey.
What I've learned is that as you go deeper, you can't make the lows any lower. You actually care more the deeper you go into it. So all you can do is make the highs higher.
One of my assumptions about being a founder and hearing from peers embarking on the founder's journey is that there's a lot of work. Is that true or is that a misconception? It's a lot of work, no matter which way you cut it. I actually have a take that whether you bootstrap it, angel invest it, or VC back it—it's the same amount of work to start from zero to one. The time you spend is like just building a small business is just as hard as building a big business. This is why I always tell people that you might as well build a big business.
It's a lot of work. It's a lot of hours. The best metaphor is like an athlete. You have to train and perform. There's just a raw amount of hours, and you can't cheat that process. But you shouldn't make it an excuse not to care for yourself. That's the line. You have to sleep, and you have to eat, I assume. laughing Yes, you have to!
The best metaphor is like an athlete. You have to train and perform. There's just a raw amount of hours, and you can't cheat that process. But you shouldn't make it an excuse not to care for yourself. That's the line.
You have to take care of yourself mentally. And you have to invest in some level of relationships or rejuvenation—whatever that is for you. So, I think you have to treat yourself like an athlete, which is like, take yourself seriously, don't sacrifice or punish yourself. Being a founder is not martyrdom. Like, no one told you to start a company! laughing Even for those who did get told to start a company, this is still great advice! I genuinely mean that! You chose to be a founder, so don't punish yourself for it. Enjoy it.
It's a lot of work for the founders and the team. The team works a lot, too. So, at the start, even good companies, they pushed until the very end. Some companies like Apple are still cranking even though they are a 40+ year-old company. It's a sacrifice and hard work, but you have to treat yourself like an athlete and understand what performance is like. It's all about increasing the company's performance and not just slaving away and stuff.
Was there any series of instances or a pivotal moment for you in your founder journey where you realized this insight? When I was fundraising, I got Covid and had to take two days off. And I came back the next week, and all my pitches were 20% better. It was because I slept for two days. I was like, "I'm a fucking idiot!" Like, I should have just slept. You just have to be self-aware, and sometimes, what you need to do better is to take time away.
Totally, and this brings us to the theme or term "work-life balance." I'd love your thoughts on that—especially how you apply that to what you do? I think work-life balance is kind of a weird term or misappropriated. Ultimately, you want to feel like your time was well spent. That's what you want to do. You want to maximize no regret.
So, I do think you want balance, but over a 20-30 year period. There will be certain periods where you'll work more and certain periods where you work less. For example, my family was sick, or my wife needed my help, and being there for them was the most important thing, and work had to suffer. Something had to suffer. There are all these tradeoffs, and you can't have everything all at once. But over a long enough period of time, you can as long as you're strategic around it.
I do think it's a little bit different as a founder or business owner versus an employee. The leverage you have as an employee is that you can quit; there are always jobs. Right now, there may be a tightness in the job market, but in general, you can leave, and that's your superpower. [As an employee], you're not tied to a company. As a founder, it's a bit different. You can quit and shut down the company or leave—but your superpower is that you don't. So you kind of change the reality around you to fit your lifestyle.
Founders integrate more of their lives into their work. You can see it in companies where many founder personalities end up becoming the company's culture. Whereas, as an employee, boundaries and structure are good for carving out your life. Ultimately, it's just about time spent and how you want to spend your time.
That does come down to meaningful time spent with other people. So, this is a hyper-subjective question. The big thing I don't like is when people project their own value system on others because everyone has different value systems. So it's not my place to tell you what to value, but I can give you advice on how to get there.
Do you have an example of how you're applying this to your life? How are you integrating your life into Merit as a founder and as Kirk, the human? So, I spent a lot more time going to events and meeting people in the community because I get energy off of that. I'm slightly more extroverted, so I integrate more of that. I take that workload from other people in the company. For me, it's less about integration and more about energy and rejuvenation. So if I'm doing stuff that's draining me, I try to design a world where, the next day, I have something that's rejuvenating me, so then the day after, I have more energy.
For me, it's less about integration and more about energy and rejuvenation. So if I'm doing stuff that's draining me, I try to design a world where, the next day, I have something that's rejuvenating me, so then the day after, I have more energy.
I am a little bit older. As I started a company, I had a whole life going into it. It's less about integrating it and more about keeping my energy high with activities that keep it high. So, in a day, if it's all fundraising, that's actually very rejuvenating. But sometimes, I get more juice from product work, going through product stuff, analyzing data, mentoring, or coaching people. So, I design my calendar in a way that there's always rejuvenation.
And how do you keep yourself accountable? It's easy to lose sight of everything when so much is happening. Are there ways you check in with yourself or others doing it with you? This is hard, and it's something I've been doing more recently with Randy, my cofounder, and my wife. Randy and I have been doing it every month or so.
We have this scale that we copied from one of our investors—my old boss, Donald. You can rate your life on a scale of 1 to 5 in three areas: recreation (like play), meaningful personal relationships, and meaningful work. So, for example, I might rate it a 3 at work—so then how do we get you to a 4? Or maybe it will be a 3 for the month, and you want to ramp up recreation to power through it. There's also, like, maybe personal relationships are at a 2, so how do we get you to a 3.
But it's also acknowledging that it's never going to be 5 out of 5 and seeing what's the most important thing to move and how we can help you do that. The thing you want to avoid is stasis—if nothing moves. That's when I think people get upset, sad, or demotivated versus feeling progress. And it's just good to call out when things are going well and when things are going bad.
I love that. And it's an interesting and straightforward framework to try and apply for ourselves. Yeah, and it's just saying it out loud. A lot of people don't say it out loud. It's more about embracing the "okay, I have to grind this out in the next two, three, or four weeks. What can I do in the meantime to keep my energy up?
For example, if my energy is at a 4, I may need to do a little bit more recreation because then I'm a little bit tired. It's like the athlete approach, right? They have time off and rest days and train hard for performance. There's stress. It's just about valuing your time and your body. It's like taking yourself seriously, and you're being affected by all these things and stuff that's happening.
What were your decisions when you realized, "Wait, I should take the framework more seriously?" What helps you actually commit to using it more? Right when I met Randy, Randy had a lot of really good health and fitness practices like meditation and not checking your computer on certain days of the week. Whereas I came in much unhealthier than I thought. I had really high blood pressure and a high resting heart rate. I didn't realize how unhealthy I was because I was young and didn't feel it. So, over time, I changed aspects of very obvious things—I slept a bit more and drank a bit less. I was just slowly getting myself into a good, steady state so that when stress and stuff happens, my body can absorb it in a way that doesn't break my body down.
I realized that these habits of drinking less, sleeping more, drinking less coffee, and exercising are all very basic things that I was not doing. That gets your body in a healthy default state. But all these activities' goals are usually to do more, not fewer things. So it's to do more stuff in your personal life to do more work and side projects. It's not about reducing yourself down to nothing. It's about giving yourself the capacity to do what you want. If I didn't do that, I don't think I could do as much as I'm doing now.
It's not about reducing yourself down to nothing. It's about giving yourself the capacity to do what you want. If I didn't do that, I don't think I could do as much as I'm doing now.
It's wild you answered this question in less than a minute, and it took me at least a year to understand what you shared. In particular, the word "capacity" encompasses time and energy. Personally, my health was in a poor state, yet I wanted to work super hard, and my mental health coach had to reel me back in by reminding me that I needed basic things like sleep and rest! And when I realized that, at the core of being a human being is health, sleep, and good food initially for somebody who might be going through it, it's tough to see that. But, it becomes so simple when you understand what it really means and apply it.
I figured it out when I was 31 or something, right? laughing It took me a long time and a doctor's intervention. The doctor said, "your blood pressure is really high for a young man with no medical issues, and this isn't good. It took a lot of intervention and habit-forming to get my stuff to normal. It took over a year of behavioral changes, so it's not easy.
But you also mentioned "energy" and "time," which I'm thinking about a lot. I realized being a founder is like an energy game, not a time game. It's not that you need more time but more focus and energy. And when you have high energy, there's enough time to do everything. With low energy, there's never enough time to do anything. That's why I talk about rejuvenation through recreation, relationships, or fitness—whatever you need to do to put more back into your tank. And sometimes, that's work. Sometimes, you work more to feel better about work, but you have to understand what it is at the moment.
I realized being a founder is like an energy game, not a time game. It's not that you need more time but more focus and energy. And when you have high energy, there's enough time to do everything. With low energy, there's never enough time to do anything.
Why is the work you do important to you? I like being a founder because I think it's the best version of myself. It's forced me to grow really fast in very uncomfortable ways, face insecurities, and embrace what could be world-class. That's when people say it's the growth and growth of the company. It's personal growth, too. So I do really enjoy it. It's really hard, but it's also incredibly fun. That's the big meaning I'm getting out of it now.
In terms of Merit, it's my life's work, and every day it's only more reaffirmed. But it just makes me realize how big the problem is. If I can solve this, I can feel happy about my time on Earth. I realized this is still a very personal thing to me.
Are there any common misconceptions you want to dispel about being in tech or a founder? We can talk about tech. Most people are not happy in tech right now for various reasons—even though they're paid relatively well. Most people are employed, and a lot of people got laid off, but they'll eventually get their jobs back. I think people have this view of the world like it's good versus bad people. And I think there are heroes and villains, which is a good narrative device, but it's not that clear-cut.
It's important to understand what everyone's incentive is. For example, when you talk to a VC, you need to know what their incentive is and who their boss is. Because it's not you, the founder. [VCs] answer to the people they take money from. To you, as a founder, it's a company, a mission, and a dream. But for them, it's an investment. And you have to think about how you would view an investment. And for your team, [as founders], we have to understand that this is a job to people. And while it can be some of the best work or the best time of their life and creating a social network...it's still a job.
Once you [understand everyone's incentives], then you'll have a more honest dialogue with people versus thinking like, there are good and bad people, which there are definitely bad people in the world but less than you think.
So I do think that when people talk about tech, like, especially in tech Twitter, it's just like a very naive view of the world where I feel like people understood the incentives of the people in the system; I don't think any of this behavior would be strange. It makes perfect sense how everyone's acting for the most part.
It's also incentives in context. A lot of people outside of tech Twitter might not have the context of what's actually going on. So, while it's not a justification for what's happening, we recognize some things are less out of the blue than one would assume without context. Yes, and there's different empathy to which, like, Elon [Musk] is a weird guy, you don't have to agree with everything he says or does, but I also get it. I'm obviously not at that scale, but I get the pressure, and that tension [as a founder] can cause you to be very weird. Whether he's a good or bad person—that's a different conversation. Right, and honestly, I think that's less of an interesting conversation, personally. Judgment doesn't move people like you think it does. You actually have to change the incentives to get the change.
Switching gears, what advice would you give to your past self—the one who just started what you're doing today? It's kind of dumb because we designed a whole mentorship platform but like "ask for help more." laughing
Going back in time, when I started my career, university, and high school, I would tell myself to ask for help more. That's the big thing. Smart people like to ask a lot of questions and ask for help. So ask for help more. Lots of people want to help you. That's tough advice to take. I would give myself that same advice but don't think I would have listened!
Give us a list of three things you'd recommend. You choose the topic.
Here are three DJ mixes that I listen to help me to do things:
#1 For running:
#2 For working:
#3 For chilling on a Sunday afternoon:
What's a favorite song or song you currently have on repeat?
Phoenix by Daft Punk. It's cool to listen to old music and be like, this could sound modern. I've been listening to Daft Punk, and it's very French Electro, Chicago House influenced. It doesn't sound outdated or stale. You could go to a club now and listen to that song, and it wouldn't sound old. It's from 1997. That stuff always impresses me.
Enjoyed the Conversation with Kirk Fernandes? Learn more about Merit at get-merit.com. You can book a mentoring session directly with Kirk at https://www.get-merit.com/p/kirk-fernandes or follow Kirk on Twitter @k3fernan.
Kirk is also passionate about giving back to The Bowery Mission.
The Bowery Mission exists to promote the flourishing of New Yorkers overcoming homelessness and marginalization by providing compassionate services and a transformative community. A donation was made to The Bowery Project as part of this Conversation.
You can support The Bowery Project by donating directly.
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