FIRESIDE CHAT WITH MERIT FOUNDERS: PART I: 5/20/2020

Stephanie Del Paggio
Merit
Published in
14 min readJun 16, 2020

Randy and Kirk are the kind of people who simply are good people. In a city like New York where you meet people of all types from all places, they stand out because they are 1) entirely driven to help (their whole company is built on the idea of helping) and 2) are extremely lighthearted and silly but understand the world’s pain. The idea behind the company they’ve created is one that encourages you to grow by learning from those who care and from understanding that you’re not alone and never will be alone.

A principle that I hold true in life is that there are few things in life that you can’t overcome if you have good people by your side and through Merit, many have found good people. It’s a shortcut through the bullsh*t to the real and that is what I’d like to touch on in this Fireside chat with them. Over the course of the next few months, I’ll have quick catch-ups and conversations with these two on Merit, growth, life, and career. After all, Merit is founded on the idea that growth and progress are achievable for everyone and it starts with the founders growing themselves.

IN PRESENT TIME

STEPH: The year is 2020. The world is experiencing a global pandemic. In this uncertain, crazy, unconventional time, what has been going on with you guys?

RANDY: I told you about how we had all those new user signups, right? Someone posted about us in a large Facebook group with around 30,000 people and people shared that post in another Facebook group which then got shared in more Facebook groups. That one post ended up having a life of its own and just kept getting re-shared…we didn’t anticipate this much usage, so we’re trying to fix everything and make sure nothing breaks.

STEPH: That’s great, yet also terrifying like a roller coaster. How does that make you guys feel right now?

RANDY: Honestly, it’s like building a startup while trying to build a fighter jet while falling down the cliff…that’s what it feels like right now.

KIRK: It’s a good problem. It’s all solvable, just kind of overwhelming. It’s like I planned a small gathering for friends and a hundred people showed up. [Note: Kirk & Randy meet with every single person who signs up for Merit and does an intro call with that person before they start coaching.]

STEPH: And what are the trends you’re seeing? What do the new users want to talk about? Are the topics similar to the ones you saw before, but just at scale or are they new ones entirely?

RANDY: A lot of the things people are focused on now have to do with what we talked about earlier, where COVID has pushed people to start thinking about their next moves a lot sooner. It’s not just layoffs, which have increased, but also career transitions. People who have been questioning things in their lives more have become more thoughtful as well. COVID has forced people to start thinking about things sooner rather than later. Their two-year plan just became a two-month plan instead.

KIRK: A lot of time spent at home just with your own thoughts leads to more people making changes in their lives.

STEPH: So today, I wanted to spend some time with you both to celebrate the one year seven-month anniversary of Merit, which honestly feels too young.

RANDY: I feel like Merit has been around for a lot longer for some days.

STEPH: Yeah. I feel like some things in life…once they enter your life, you forget what life was like before they entered it. That is how I feel about Merit — that it’s always been in my life.

Something that interests me a lot is your dynamic — the way you guys work together. You both had other jobs and other opportunities to pursue and you chose not to do those things and instead chose to work together on Merit. And throughout the past few months, both of you have said things that have really resonated with me in terms of your passion and your mission, like when Kirk said that he wanted Merit to be a school for children to grow into their powers.

ON THE BEGINNING & GROWTH

Going back to when you first started, how have you changed since you first started working together on Merit?

RANDY: I feel like if I think about myself back in 2018, I felt defeated. I had a sense of what problem I wanted to solve, but I didn’t necessarily know what the answer was. I felt like I tried a bunch of sh*t, but it wasn’t necessarily working.

RANDY: I think this is true for both of us. It’s been really fun to work on something with someone else who cares and who has the same long-term vision. Kirk has a similar desire for impact. I think my confidence has grown in many ways. When we first started Merit, I wasn’t as confident, but now I feel super confident. Signups are crazy; we have lots of stuff to fix and we’ll fix it.

KIRK: I would agree with what Randy said, cause I feel like Randy has always been smart, but through Merit he has gotten a lot more confident. I think he’s always been ambitious, but I think there’s a confidence around using your skills for the right things that is understated. I think it’s been really cool to see Randy go through it. From when I first met him to now…he’s always been smart, but now he’s smart and confident, which is amazing. When I met Randy, I was kind of lost. I was plowing along and I wasn’t making a lot of progress with my own ideas.

I feel the biggest kind of growth within me was partnership. Prior to Merit, I had never really had a partnership with anyone, and it coincidentally happened around the same time as when I got married. However, I think marriage is more forgiving than a cofounder partnership in the sense that our economic futures are much more tied together in the latter. Our reputations are much more tied together, right? It’s a higher stakes thing.

Being a partner was something I hadn’t done before. Even at work, I had been a leader and an employee, or various combinations of those things, but not a true partner. Randy has this creativity around approaching problems that I really appreciate. The fact that smart people like him choose to work on this problem we’re trying to solve is very motivating. Smart people could work on a lot of other things. To me, our partnership is clarifying and it gives me more confidence. It reduces doubt in my mind, like if Randy’s working on this, then that is a good signal. In that respect, it makes me doubt things less than I would if I were to work with somebody who was not as smart or was not in it for the right reasons.

RANDY: It reduces anxiety for me too. I’m not married, but Kirk is, so he can speak to that. I’m glad that I spend time getting to know each other and really working through sh*t because it’s a relationship first. It starts with two people who genuinely like each other and learn how to work together over and over and over and over again.

KIRK: Even when you don’t feel like working and you’re disappointed or you’re frustrated or you feel insecure, there’s still that partnership and that’s something that I think is a truly unique experience that I had not done before.

RANDY: It’s actually ideal in terms of what I want out of a partnership, which is an integrated curriculum that has worked out so far for us. It matters being aligned on what the long term goals are.

KIRK: Long-term direction. You can’t necessarily say exactly what you want something 10 years from now, but you can agree on the fact that you want to work for 10 years on something and the fact that you want to commit.

RANDY: One of our first exercises together was that we wrote out all the ways we could fail and talked through all the ways we were willing to succeed or fail.

KIRK: And it was really scary, but worth it to get everything out. It was an intense first date where we talked for six hours.

ON FIRST IMPRESSIONS

RANDY: Long story short, I thought Kirk was super fashionable. He was wearing this nice varsity jacket. The reason why I thought that was confusing was because I didn’t know if he was trying to impress me or something. When you’re an engineer, you’re wary of those cases where the founder wants you to work on their app idea, but isn’t necessarily trying to have an equal partnership. Obviously, that didn’t turn out to be the dynamic, but that was in the back of my mind for sure and genuinely is a concern for most engineers.

KIRK: Yeah, there’s a lot of situations where business people are looking for someone to build their “genius” idea. That’s 100% true. My first impression of Randy was that he was a genuine person. When I first met him, I felt like he was 13 years old because he looked very youthful. He has a pure, youthful face! No blemishes. Disclaimer: He looks a bit older now.

Overall, I could tell he was very smart and very thoughtful. Excited and eager — those are my big first impressions. I didn’t really think much beyond that.

ON DIFFERENCES

KIRK: One of the most frequent questions we get asked is what we disagree on and I would say fundamentally it’s mostly small kinds of operational problems or tactical stuff. And then at the highest level, I think I’m just a lot more focused on iteration, quality, cycle [T1] [T2] and really nailing something. And I think Randy is a lot more ambitious about the growth and the scaling and the distribution.

There is less debate about what to do with the company or how to hire folks. There are more small disagreements about the small sh*t. I think for the most part, we agree with each other.

ON KEEPING IT LIGHTHEARTED

If you ever meet Kirk and Randy in person, you’ll find that they are extremely lighthearted and laugh frequently. Any aura of tension that might exist is quickly broken. They immediately make you feel at ease, which is an important topic when you’re trying to make people comfortable to receive or ask for coaching.

KIRK: The topics on Merit are kind of serious. The things that people go through are serious and the context is that the assumptions within Merit are serious assumptions. Discrimination does happen and people do get left out of things. We’re humorous and light because the work is so serious. The hardest things that you think you are facing today are going to be things you laugh about in five years. But it’s so hard to know that when you’re in the moment, because you think the world’s literally going to end.

RANDY: Things are funny because you can look at them from a different angle, right? That’s a big part of coaching. Being there for people is about giving them perspective.

ON HONESTY COMING FROM WITHIN

RANDY: We’re actually pretty transparent about pretty much everything to each of our different audiences. In our investor updates, we’ll say explicitly ‘here’s how much cash we have in the bank, here’s what we’re working on and here’s how we’re making progress.

I feel like the fact that we’re so transparent makes it a lot easier to be candid because, I mean, we’re working on something we think can help people. We’ve done that enough times where it’s pretty clear that that’s the goal and the impact [T3] we want to have.

KIRK: It’s the advice you give Merit coaches, which is that the goal is to help people and not sound smart and sometimes the simplest thing you can do is not that impressive, but it’s still impactful.

ON BEING A ‘FOUNDER’

KIRK: Sometimes ‘founders’ can fall into the trap of over-complicating things or making our work sound more impressive than it is when the reality is that just starting a company is hard enough.

It is very hard to be a founder and it’s very hard to be a small business owner. All those things are hard. I don’t feel the need to convince anyone of that. Most people understand that. It’s hard.

STEPH: I think sometimes the best businesses can be the simplest things that provide value.

KIRK: For us, changing behaviors, perceptions and reducing systems of discrimination is incredibly hard. Multiple generations of people have tried to do that, and people have literally died trying to tackle it.

STEPH: That’s a good point. You are, by standard definition, a tech company in the sense that Merit is virtual and it is on a website. But at the end of the day, it’s more about systems and relationships in the workplace. And I think that affects every single person.

ON MERIT’S SURPRISES

KIRK: What’s been surprising to me, from just a journey perspective, is how many people have offered to help. It’s huge both in terms of our investors and users. You’ve helped so much, along with other people we met through the process. I didn’t think I would meet so many people building the company. I’ve just met so many f*cking people that are really, really cool and that was super surprising and incredibly positive.

In terms of the product stuff, you have one good idea a year and you’re just milking that idea to pure existence. We had one idea around connecting people in different companies about a shared interest over video and that’s become the core of everything else.

We built a bunch of features to make it better and simpler and true from there, but the core nucleus of the idea has always been that. As a product person, you think you have to keep coming up with more ideas and new sh*t and new features and more things, but it’s really just an act of making that first idea stronger, cause that first idea was probably the best idea. That’s the humbling thing; it’s about the simplicity of the idea that’s the most important and making it high quality and true for everyone.

RANDY: The complexity is that it’s very simple to use, but very hard to build or scale.

KIRK: It’s training people to ask for help and it’s coaching people to get that help. I think that’s all it is. It’s just a means to an end of increasing more coaches in the world and creating more requests. There’s just so much work to get people to the point where they admit they need help.

RANDY: And I think we’re at 1% of that honestly. There’s so many more people that could use our platform for all kinds of reasons. I think that the video aspect of being online across different companies, those are all implementation details that allow the experience to be really unique.

STEPH: Anyone at any company could be your coach and rooting for you. You’re exponentially expanding and broadening your horizons.

RANDY: Every day I get a lot of LinkedIn requests from people who want to connect with me, but that platform isn’t conducive towards connecting to people because you don’t know what you can help them with and you just don’t have the capacity to find out. But with Merit, you’re saying “Hey, here are the things that I can help with and here’s what I’m available to do.” You know what you want help with and you can easily see if there’s a match.

I think if you can solve it well, then you can help a lot of people. We try to mitigate that awkward shitty feeling about misconnections which sounds crazy because it’s just people asking for help and people who can give help and connect them.

STEPH: I think what Merit is doing is replicating the feeling of having a mutual friend introduce two other friends together. Bringing strangers into a room with trust. You and Kirk vet out every single new user on Merit so by the time they’ve reached out to the coach, they already know you’ve met them.

One other thing Merit is great at is encouraging people to let go of their ego and look at growth and mentorship as a way to improve your life instead of looking at coaching as a sign that you’ve failed.

That was very interesting to me when I was trying to get some of my friends to join Merit who had been telling me about their issues one-on-one. But then, a lot of them could not get over that innate voice stemming from their ego saying “I’m asking for help and making it valid that I have failed”, which was very hard for me to understand at the time. As Merit continues to grow and as more people become used to the idea of asking for help, it’ll become less stigmatized, like therapy.

RANDY: Basically, the fancy prep school that I got a scholarship to go to had this [situation] set up where they had office hours with teachers between classes. During those office hours, you asked teachers for help. And what was so common was that people who didn’t go to fancy prep schools before thought that if you went to office hours, it meant you were basically remedial. But the people who did all knew that office hours were the time when you basically got the extra help so you could perform the best.

It was consistent that the kids who showed up during the extra office hours were always the kids who got straight A’s because they knew that the time for one-on-one attention gave them the extra help to do better. It’s actually the kids you give the extra help to that perform the best consistently. And I saw it for myself and it made a huge difference in my life.

The people who show up on Merit are super motivated cause they’re like, “Fuck it, I’m going to figure out what I need to do in order to get to the next step. And I feel that there needs to be a re-education to make that clear. And what’s also interesting was that when we talked to the coaches, they all knew that was the reason why they got to where they are and wanted to coach others, cause they knew that the people who ask for help do better. Like, “If I can give my 2 cents that will help someone, that’s sick. I want to be able to pass it on.”

STEPH: You bring up an excellent point. I wonder if it almost relates to your upbringing or socio-economic background. It’s the mentality that there’s unlimited resources versus the mentality that there’s scarcity.

KIRK: Yes. Scarcity and on top of that the feeling of being entitled or feeling like you’re worthy to be able to actually do the things you want to do, or feeling you can do so without a sense of shame or feeling like you’re taking from a financial resource?

We need to figure out that education part better. We try to be cognizant of design decisions. That’s why we use the words “learning” or “coaching” and we don’t use “mentor” or “mentee” or “executive coaching”. We want these things to be socially acceptable.

Then the other half is just making it easier to get coaching. To Randy’s point, I think we’ve done a bit of both and there’s a lot more to accomplish on the educational part. I think that’s the cool part about Merit and the fact that we can create more coaches and more learners.

It’s just as hard to get people to ask for help as it is to tell them they’re an expert, which is super wild, right? All those things are weirdly equally hard and just cause you solve it for one group doesn’t mean you’ll solve it for another group.

RANDY: It seems like there’s a missed opportunity if there’re so many people who want to help and there’s so many people that need help and we don’t connect those people. We can create this culture with a J point of growth and intersection.

KIRK: It’s pretty programmed in corporate America to value performance around your work. I think to your point about the ego — that’s going to take a while to unravel, but the tech people and the under-represented people usually happen to be more crafty because they get less resources and less funding and have to be a bit more experimental. With Merit, we’re reproducing what women have always done in history, which is ask other women at other companies. This is the stuff that’s been going on for a long time behind the scenes and we’re just kind of building infrastructure for it and doing it at scale so it’s not bound by one person or one group.

CLOSING NOTE

Merit continues to be a place where you can ask all the hard questions and not have anything held against you. From guidance on how to tackle your first job as a PM to dealing with discrimination in the workplace, Merit brings together different perspectives and gives you more perspective, which can bring you clarity in your career. Check it out here and feel free to reach out to anyone who is a Merit Ambassador to find out more. Better yet, just sign up at this link and chat with Kirk & Randy yourself.

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Stephanie Del Paggio
Merit
Editor for

Born in Houston, raised in Shanghai, now in New York. Visit my website www.52storiesNYC.com where I interview New Yorkers about their passions.