Leading a Startup While Navigating Personal Strife

Kirk Fernandes, Co-Founder, Merit

Being a leader, especially one of a startup can be more than a full time job. What happens when stressful things happen in your personal life? I talked with Kirk Fernandes, Co-Founder of Merit about how he handled this when three members of his family got sick. Our conversation covered why he started Merit, what he learned about asking for help, the importance of self-talk and why he recommends therapy to everyone.

It’s so great to see you today. (laughs) We've actually never met. It sounded like, "Oh, we know each other." We do have someone in common, Sam DeBrule, who's also been on the series. So that's how we connected. Can you introduce yourself?

Yeah. I'm the founder of Merit, a career mentorship for the under-networked tech worker. We focus on women, people of color, immigrants, folks breaking into tech, and those in that first year in the industry. We connect them to senior leaders to grow your craft and career. My background is in product management and engineering, I studied computer science at the University of Waterloo in Canada. I've worked in big tech, early stage, and have been a consultant. So I've kind of worked all the roles and all the stages of technology. Merit is my thesis statement on my career — the idea that your network dictates the quality of your career. We fundamentally believe that high-quality mentorship is the best way to grow your career. So that's the genesis behind Merit.

I love that. I think it's true. I have a strong network. I think that part of it is luck, and part of it is hard work. It's so valuable, a career accelerator in ways that other things are not.

Totally. I mean, I've been fortunate enough... in Waterloo we had a co-op program which The university forced us to essentially work in these four-month internships, and they had huge relationships with big companies like Microsoft. And going to Waterloo was that key decision of that key network that essentially unlocked my, 10-year-plus career in tech in the United States, And if I didn't unlock that network I don't know where I would be. So I think a lot of people in tech, especially people who didn't go to the University of Waterloo don't have that swing or that shot. So that's why we called it Merit, Like what if the tech industry was actually a meritocracy? It's kind of like a joke,...

With under-represented folks often, that network is something that eludes them but can be a big career lever.

Yeah. In my last job, I was one of the Product Leads at VTS and a big kind of diverse team. And no one tells that managing a diverse team is harder than managing a homogenous team because you just need to know more things to teach people and grow them. And what I often did was connect my team to people outside of my company to help kind of grow their career, either people to meet, people that are like them, people that are also teachers,. And I was doing this with the connecting folks, and oftentimes these people outside of our company. And I was like, if I'm struggling with this as a manager I bet tons of managers are struggling with this. So that was the idea behind Merit , I made it so I could have been a better manager, right?

I think a lot of people, when they sign up to be mentors on Merit the first thing they say is, "I wish I had this when I joined the tech industry like I really wish I had this." So we're building it for our past selves and our future selves.

I love you're building for your past self. Where is the company now?

We're kind of a pre-seed startup. Merit is built and funded by tech workers, so our cap table is people who can use the product. We have about 5,000 members and mentors live on the platform. We have a small core team of people, including myself and my co-founder Randy.

So the leadership team is you and your co-founder Randy?

Yes.. Randy was the CTO of Jopwell, which was a DEI recruiting platform. So it would connect first-year people to big tech or big banks jobs. His takeaway was, that placing all these people in their jobs is not enough, they need a network to grow, and that was the main reason why they would churn. So we saw two sides: he was placing thousands of people, and I was managing lots of people. We both saw the same problem. This lack of network leads to like a lack of career growth, so we connected those two dots and that's how we met. In terms of our division of labor, I think we're kind of unique.

We don't say CEO or CTO, we're both co-founders and we're going to keep that title. But it's super simple, I sell Merit to investors, to customers, to employees. Randy builds Merit, theproduct, engineering, design, culture, support all that stuff. You can think of it as like the builder-in-chief, the salesperson-in-chief, or more creatively as my wife puts it, you need a scientist and you need a storyteller, those are the two roles. You're running experiments to essentially figure out this product, and you need to tell stories to convince people to come to the door. So that's like the super high-level division of labor, but it's a pre-seed startup so it’s an everyone does everything kind of thing.

Where are you all at in terms of your next step around the company?

We raised a little chunk of money at the start of the year to bring on design and a content help, which we did. So right now we're just building and growing, we have all the people we need.

That's fantastic. I'm not someone who says you have to build huge and scale fast. I think we're seeing a little bit of that now. Maybe they grew a little too fast and they need to cut back a bit now.

Yeah. I think a lot of that too is the startup hiring as we all noticed, the American economy is a just-in-time economy, it's not a just-in-case economy, right? The capital markets and interest rates drove a lot of that funding, which drives a lot of the hiring. It's not necessarily tied to market demand, right? You want to scale ahead of the market, not ahead of the investors, because they come and go, unfortunately. You're creating a market.

So this was your first time as a founder. Was starting a company something you planned to do? Was it a goal?

I wanted to start something from scratch. I was a lead product manager and didn't want to become a CPO, I didn't want to necessarily climb that ladder. It was more, I didn't want to do that so I kind of went the other way. I had a chaotic and expensive journey to becoming a founder, so I would not recommend that for most people. When I quit my job, I didn't really have an idea or a problem, I didn't have a co-founder. Once you have those two things — a sense of the problem or the market and someone to work with, then progress happens quickly.

If you don't have those two things it's kind of hard to make progress. I spent a year wandering the desert trying out different ideas. Most of them were relatively unsuccessful, and I burned a lot of money. We had a wedding at that time, so we burnt through like all our cash savings with a big Indian wedding. So we burnt through everything that we had, then I ran out of money, and I had to do freelancing and consulting. And honestly, through experimentation and random luck, I kind of coalesced on this product idea, and I met Randy. That's the journey of Merit, that's kind of where it starts more formally. But there was a year of wandering the desert.

I think a lot of folks who want to have an impact have wandered that desert trying to figure out how to do that.

Yeah, I think to your point, that's very common. I think people just don't talk about it. But it was a great year. I learned a lot about myself, you learn a lot about cash flow, sales, money, and healthcare in America. Lots of stuff you learn about.

I believe this was the best use of me, the best version of myself. The problem of Merit solves, essentially democratizing the professional network is a thing that's close and near and dear to my heart, so I'm very happy where I landed.

I love that. How is founding a company different than you expected?

Oh, it's way different. I think there are pros and cons.

There’s an inversion. The cool thing about being an employee to me, I think people don't use this privilege enough is that you can quit your job. As a founder, the inversion is you can't quit. Either you make this company successful or you shut it down. So once you lean into those two things, you enjoy both parts better. If you kind of have a more free agent-style approach to work in careers, I think you can be a great employee, you can reap the most of these kinds of tours of duty. But if you invert it as a founder of like, "Okay, I can't quit. Then how do I make this reality work and make it something I enjoy?"

I think you have to embrace the different levels of responsibility. It's also a shit ton of control and responsibility. We made Merit. It's a thing we made up together, and people use it now. It's relatively big, it's not huge but it's relatively big. It's like a work of fiction, essentially, that's reality. So that's really powerful, and that motivates me. So that's the biggest difference to me.

That makes sense. Had you been in leadership roles before?

Yes, yes. So as a CS undergrad I did a bunch of engineering internships. I didn't like engineering. But I like front-end development and became a product manager at Microsoft. I worked on SaaS and productivity products. Then I transitioned to early-stage startups like Hightower and VTS. I became a product lead. I was managing a team of five or six PMs. I think what's interesting when you quit and start your company it's you and your co-founder. In those early days, you're not managing anyone, it's a partnership. So you kind of lose the thing you're good at, which for me is managing people, so you have to reinvent some skills. It was kind of hard in that transition.

Now we have a team and I'm like, "Oh yeah, I think I'm a decent manager, this is fun.” I forgot what it was like. But (as an early founder) you have to go back to the hard skills. My background is in computer science, engineering, design, product management, they're mostly maker skills, they're not like sales skills and storytelling skills, and marketing skills. I'm essentially the marketing co-founder, so there was a huge learning curve on that skill set. So I had to start back at zero as a founder. So I had to learn how to do just pure output, and then I learned how to do marketing as well. And you know, like marketing, fundraising, sales, hiring, to me they're all very similar skill sets. I lost what I was good at and I had to develop new skills. Now I’m using them all again, which is dope. But that first year and a half was very steep.

I bet. Thank you for that, it was so good to hear these distinctions and pull them out.

I understand that you've had sort of multiple family members with health challenges in the past year. I wonder if you could talk a little bit about that and what it's like leading a startup facing these personal challenges.

This year was probably the hardest year of my life personally. My wife and my brother experienced health issues and my dad just recently passed away after many years of a chronic illness. For context, I'm based in New York, I've been living in New York since 2015, and I've been living in America since 2011. But my family and my wife's family are both home in Canada and Toronto. So this year I've been flying back a lot to do caregiving for my dad up until he passed, flying back every month. In the previous two years with COVID in Canada, they had pretty restrictive entry requirements even for citizens.

So the last two years were hard. Seeing my family and doing caregiving. But then the last six months were incredibly hard. In terms of the challenges of leading, I think I've just been super lucky to have a team that tags in for you and helps. It was humbling to feel like I'm not just one person working on Merit, multiple people are working at Merit. I felt a lot of relief in delegating and not doing things, giving work away, and saying I can't do something. I don't think it was true like a year ago. If all this happened a year ago I think I would have burnt out.

What changed your mindset?

I think you're familiar with this. When horrible stuff happens to you, you find some fifth or sixth gear you didn't know you had, or you just break down. I found some gear of clarity, and it allowed me to focus on the most important things. As a founder, there's just so much inbound and noise, you have to triage a lot of stuff. On any given day there's only a handful of things that really matter, it's just hard to know what they are so you try to do it all, that's what most founders do. And that works for the first bit for sure, and you should. I think it forced me to be clear. Randy, my co-founder, went through Y Combinator with the previous startup.

He said that during a recession, the advice that he got was you're just supposed to do what you normally do. Focus on a customer, grow revenue, and be cheap, these are all things you're supposed to do, you just have to do them now.

During a crisis, as a leader, you just do all the things you should have done. Be super clear, manage your energy, focus on the most important stuff, and be honest with your team. That's just stuff you should always be doing, right? It forced me to be more clear, to be more honest, to be more focused, and ask for help.

I think for many leaders, it's hard to ask for help. How were you asking for help before this?

I was honestly not that good at it. With Merit, we built a whole platform around asking for help. I was one of the founders of that. So it’s kind of funny, right?

I'm chuckling because I get that.

Yeah, you get it. It's kind of comical, right? This time I learned to ask for help, and flag problems. To be like, "This isn't going well." You build that muscle because it's the only way you can survive. If you don't do that, those startups usually fail. Because things always go wrong. So I think the reality of Merit forced me to develop that skill. I also have a good team. They all stepped up. I was just also more honest with myself about my energy levels. Like, the week of my dad's funeral, I'm just not going to be that productive.

There's a handful of things that need to get done. You do those things, and then be okay with coming back to everything else the week after. There was the decision I made to not do anything on that Friday to see my dad, and I didn't know he was going to die the following Wednesday. I was about to go into that Friday like a normal day of work, but I'm so glad I didn't because that was the last cognizant day I had with him. But then I also decided on the Monday to be there for my team and organize stuff, because I knew that that mattered for that week, there was a bunch of stuff we were doing that really mattered.

Then I acknowledged that my energy is going to get worse during the week as we get closer to the funeral. So you have to make all these decisions, there are no easy ways around it. I got into an argument with my family during this period because they’re like, "You work so much." And I was like, "Yeah, I have to. It's like my own company, it doesn't happen if we don't do it." It's not like a 20 person company where I can delegate all of the stuff to others. I'm acknowledging that yeah, I can't have everything in these moments.

There's no convenient time for your dad to die. Or your wife gets sick, it just happens. You just hope you make the right decisions and don't regret them later. That's all you can really hope for.

I work for myself and I have a chronic illness. When hard life things happen you have to find your way. You have to make choices. It’s not always easy.

There isn't some reality where everyone's happy, right? What I've learned about being married, having a family, and having a team, there are hard trade-offs. Especially being self-employed or having a founder, there are pretty hard trade-offs you have to make and sacrifices. I think not acknowledging them is a little delusional in my opinion.

How open and vulnerable were you with your team when all of these things started to happen? As a leader it's interesting. Should I say something, or should I not? How do be a human and a leader?

During my wife's health condition, she was hospitalized for a week. During that time I was actively fundraising. I was doing pitch meetings, and then going to the hospital afterward to make sure she was getting better. That was probably the most stressed out I've been. I was just holding on for dear life. You're also fundraising, you're pitching, and you're super insecure. "Will they like me?" I'm very open with my team and my co-founder, on what's happening. I told them, "My wife had this, this is what happened, she was in the hospital."

Everyone was really nice, they asked how I'm doing. I try to be as honest with the information and how I felt. Like, "I'm well, all things considered." Or, "I'm tired." I'm very transparent with that stuff. The beauty of Slack and a distributed team, is being able to type things out versus like saying them. So I think there's something nice about, "My wife got out of the hospital today, I'm going to go pick her up," that kind of stuff right? So you have an audit log, a record of this. 

During fundraising, I delegated less, because I couldn't delegate a lot of that stuff. As the founder, that's my job. But in building mode, you can delegate more and reprioritize stuff. Fundraising is very much a time box, so you just need to get stuff done. But that was also way more stressful because it was less conclusive, the outcome with my wife as she got better. It wasn't clear that she was going to get better, but she did.

That's good.

Yeah, both my wife and my brother are doing a lot better than they were. Those were moments of crisis versus grief with my dad. I'm pretty relatively honest with the team. I try to be honest with my investors too. I bring it up at our monthly board meeting with key investors. Something I'm trying to do going forward is to acknowledge what happened in the last little bit to the larger set of investors. That's going to be a stretch because I don't really talk about personal stuff at that level.

So talking to the team was ok but talking to investors feels different?

To investors is different because you want to project that things are going well. And they should be going well, right? But the reality is that it’s chaotic. And the investors have been most inside of... Inside knowledge, right? So it's a bit rawer. So, you try to find that balance.

I've learned the more honest you can be the faster everything goes. Not to say that you disclose everything, but you should be honest about the material things that happen in your company. And if something has happened materially to you that's an important detail to share. What you realize is that everyone helps.

Unless you have bad actors, everyone will help or offer support, so you shouldn't be scared of that. If they don't help it's not because you shared information. It’s because the relationship wasn't. It's a different reason, right? So you have to get over that fear.

It takes vulnerability and trusting everything is going to work out.

Yeah. Vulnerability is a great term. I think it’s also a self-talk thing. I don't like the words confidence or imposter syndrome, because they feel very vague. The way I think about it, and this matters a lot with mental health stuff too is that everyone has an internal dialogue.

Everyone talks to themselves. It's important to acknowledge what you say to yourself. There’s something you're saying to yourself that's convincing you to do something or not do something. Debugging that unravels why you're vulnerable or insecure. That took a lot of time — like three years — to really understand.

When we think about health issues, we often think about the person. But you were supporting three members of your family. While running a business and being responsible for a team. How was that for you? What kind of support did you get?

My team was supportive. My friends were supportive. There are merits of a network-based product. I have my own network, a New York network, the Merit network of people, and all the investors as well too. I just ask for help, and people have helped.

I've learned to take the help. Don't try to pretend to be brave. If someone says, "I'm going to cook you a meal," just like, "Yeah, I'll take the meal." Or someone's like, "I can do this for you," just take it, that kind of thing. You don't need to fake being brave all the time, sometimes you can be like, "Oh, this is like a lot, I'm a little bit scared."

I'm lucky, fortunate to have that. But there’s this idea that you have all these jobs — I have a job of being a founder, I'm a husband and a friend and it matters, but doesn't matter as much as being a founder. And the inverse is true where my wife knows I'm a founder but I am her husband first.

She's proud of me and she wants me to do my work but I need to be a husband, right? You need to be a son. Those are the important things to those people. It's clarifying when you think of it that way because it doesn't matter if Merit's successful if I'm not there for my dad. I also have a responsibility to the company.

How do I be a founder, leader, and human at the same time?

For sure. For Randy, I need to be a co-founder to him. I need to be a boss to my team right? So I need to be those things. I can't abdicate those duties.

There's a balancing act. It sounds like you have such a great network of people too. Did you get a coach or a therapist or anything else for more specialized support as you were going through all of these things?

I actively talk with the people in my life about these things. The thing that I've learned is just to talk about it. They're not trained professionals, but just saying it out loud a couple of times helps you process it. I do have a therapist, and I saw a therapist because of the first traumatic event. I was thinking about therapy, I was like, "You know, the last year was kind of stressful, I had to reorganize my habits a little bit." When the health condition happened I went to therapy instantly. Then things got worse. Therapy is very useful. I would recommend it. It’s so worth spending money on having a trained person. 

Oh yeah. I've had a therapist for a long time. I think therapy is great for everyone, especially those in leadership roles.

I think it's good for everyone.

There's no stigma attached to therapy for me. It helps us understand what’s going on inside our head and process what's happening. As a leader people are depending on you so that kind of support is important.

Oh totally. (As a leader) you have to present clarity, strength, and focus, but the vulnerability stuff is hard, especially when you're someone's boss You have to have a lot of self-confidence to be like, "I don't know what I'm doing.” But then you realize, especially in a startup, you can say that and people will respect you, as long as you figure it out. People know when you're lying.

Therapy can help you process faster, and give you tools.

Definitely tools. I view it as debugging my brain a little bit. There's a very specific role that cognitive behavioral therapy addresses in terms of trauma, specific mental health issues or disorders, or understanding triggers and behaviors, which is important in almost everyone. You can't depend on your family or your spouse or your close friends to do that work. It’s mostly on you, but you need a trained person to do it. So you don't want to try to have your wife do therapy on you, I don't think that's a good idea.

I've learned that the value of a network is diversification. So you're not dependent on a single person to get you through this. A therapist is another node in the network, it's another tool in the tool belt. You can't depend on your spouse or your girlfriend or just your family to help you get meaning out of life, you have to derive it yourself.

I have tears in my eyes — the therapist as another node in the network is a great way to think about it.

My wife and I are both employed. We have two salaries so we have a certain financial advantage. My wife has healthcare, and the therapy is covered by her healthcare. If she didn't have that healthcare plan I don't know if I would have done therapy, because it's expensive. We pay ourselves reasonably well but not that well, so I don't know if I would have prioritized it if it wasn't available essentially for free. So there are all these built-in advantages that not everyone gets to take advantage of, which is also why we started Merit 

The cost was a big reason I didn't do therapy for a long time. Only once I realized my wife's healthcare plan covered it, and something traumatic happened I realized it's probably worth spending some money on. But that's also probably a big reason why people don't do therapy, is the cost.

Especially in the United States. Our healthcare is just notoriously expensive.

Complicated at best, horrible at worst, yeah. Seeing my dad go through chronic health conditions too made me so much more grateful for the Canadian system.

That adds a different layer of stress right? Someone is not doing well, and now we have to worry about cost, or can we afford this kind of support?

This is an interesting thing about self-talk, I don't know if this is useful to the audience. But a lot of times when I think of therapy, or I'm going to a therapy session where I'm like, "I don't know if I want to talk about this," I do tell myself like, "Someone would kill to have this session, you have it for free. So take advantage of it or don't do it. Like pick something, pick a side." There's a self-talk about framing relative distance I found very useful, at least for me personally, motivating me to do hard things. Like, "Someone would kill to have this session, but you're getting it essentially for free."

Self-talk is so important for our well-being. Was managing your inner dialogue something you’d been doing before all these happened?

It’s something I've been thinking about for the last year or so because founding a company is stressful, and I think in general everyone has gone through a lot of stress with COVID, and politically in America. The stress generally has gone up a lot. One of the few things you can control is what you say to yourself, especially in a world where a lot of things are kind of outside of your control.

I don't like the words confidence or imposter syndrome, because it's not super actionable. But everyone understands how to give feedback. Self-talk is just giving yourself feedback.

As a manager, as a leader, one of the most important things you do every single day is give feedback. You have to get good at giving feedback, that's concise and actionable, that’s useful. How are you going to increase your performance if you can't give yourself good feedback? Some people self-talk with stuff they would never say to other people, which tells you that there's like a huge misalignment, right? I've had periods where I'm like, "You're stupid," or like, "This is dumb.” This is stuff you would never tell others. At least I wouldn't, other people do. I personally wouldn't tell other people to their face that you're dumb because it's not that actionable. You can be more specific. If you don't like something about them you can be a little bit more useful or constructive, as fun as it is sometimes to call people dumb or ideas dumb, right? It doesn't change anything in the world to do that.

I’m building products for the first time. I have no idea what I'm doing. A while back I noticed my self-talk was saying things like, “I don't know what I'm doing, I can't do this." I changed what I said to myself. “I don’t know what I’m doing yet. Or, I need to find support in this particular area.” Talking to myself in a different way unblocked me. I started moving forward pretty dramatically after I changed that feedback loop.

That's fantastic, it's like, "I don't know what I'm doing," which is like, "I'm learning product for the first time. How can I get better at it?" It's different, right? That's great.

What advice do you have for other leaders who are facing a personal challenge while leading a company?

The stuff that I've gone through, there are no ways around, it's just hard. It's really hard. Embracing that it's hard and it sucks is the healthier way to do it, than pretending that everything is okay. When people ask how I’m doing it’s like, “Well, in the sense that I'm back to what I was before this all..."

I've found value in sharing it with other people in a way that feels authentic or reasonable to yourself. People can only help with what they know, they can only help you solve problems they know about. So, you have to tell your family about work, you have to tell work about your family. Everyone needs to have a shared context. So sharing is really important.

In terms of personal tragedy and grief, you can't make yourself process things faster. All you can do is focus on daily habits or things you can do today, that's what you have control over. And in terms of super practical stuff, I would recommend everyone to do therapy.

Yeah, grief and loss take time. It has its own timetable and its own rhythms. We have to be gentle with ourselves and understand that we can't just force it through. We can't ignore it, but we also can't force it through on a timetable like we might a project plan.

Yeah. I think there's a lot of overlap with having moments of inspiration and having moments of sadness in terms of how you process them. I think they are very similar in mechanics, where great ideas just kind of come to you, kind of in the same way that sad thoughts come to you. Like, they both just kind of happen. You can't force a genius idea, but you can build discipline and habits so that it's inevitable right? You can't get over someone dying, but you can control the daily habits that eventually will help you get over someone dying. That's what you can do, that's all you can do. So over a long enough period of time, you will process it. But being like, "I need to be over it by this day," is not going to work usually.

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