Riding the Roller Coaster as an Early Stage Startup Founder

A conversation with Sam DeBrule, Co-founder, Heyday

This week I spoke with Sam DeBrule, co-founder of Heyday, a research tool that makes it easier for people to remember things. We talked about what it’s like being a first-time founder of a startup that’s trying to find product-market fit, the importance of getting support, and the conversations leaders have with themselves.

This interview has been lightly edited for length and clarity.

I love the idea of a tool that makes it easier for people to remember things. Why did you all start this company, what was the impetus?

Maybe the best way to start is comparing it to other productivity tools. If you've used something like Google Docs, Evernote, Roam, or Notion you know tools like that are great, but to get value out of them, requires tons of manual input and maintenance. As soon as you stop maintaining those tools, the value that you get from them starts to decay. So, my co-founder Samiur Rahman and I thought, "What would a tool look like that is updating itself for you, that is saving automatically all the research that you're doing, and then resurfacing that to you at a time that you need it without even you thinking about proactively looking for it?"

The story of why we started the company comes from my co-founder Samiur. Samiur was diagnosed with ADHD later in life when he was in his early 20s. He's working at a big tech company, and so many of the systems that were in place were these systems, these productivity tools that weren’t working for him.

I like organizing but I'm also scattered at the same time. I have a chronic illness, and so I have some memory problems that make it tricky sometimes to remember where to find all of my research. I use Notion and I enjoy Notion. But I'm losing things constantly. Roam was hard for me because, while I liked the idea, I worried about getting lost in my thoughts. So while I love the idea of Roam, I never ended up using it because it didn't quite work for my brain.

Exactly. And what we've heard from so many people who use tools like that is, first, you have to form a new habit of going to this tool as a destination. The way Heyday is built is it is a tool that, first and foremost, that enhances your Google search results with past research that you've done. The problem for people is you're reading something great and then maybe you save it in your bookmarks bar, maybe you emailed it to yourself or texted it to yourself, maybe you put it in Evernote or a Google Doc with like a link or all of those, and then a week later, two weeks later, a month later, you are now reading something and then that thought sparks in your brain of, "Oh, I read something great on this topic." And then you don't remember where is it, in which tool is it, right? And then the painful point of that is if you never find that thing, the idea that you're trying to develop always feels not as good as you knew it could be.

This is my life. I have these ideas, I read voraciously. Later I want to find it and have to think where I put it, "Was it a bookmark? Did I email it to myself? Did I save it in Pocket? Is it in Notion?"

Exactly. So, we're saying just use the internet like you normally would, search Google like you normally would. And Heyday just sits there on the side of the page where... It's currently white right now if you use Google and you don't have Heyday. Once you have Heyday, the overlay appears. And any time you search, we're just showing you relevant content from past research that you've done.

Where is Heyday in the business cycle, however you want to define that?

So, the definitions of the amount of money raised and what stage you're at change all the time. So, I always encourage people to think about how much money have you raised, right? We have raised under $6 million. By current classification, we would be considered a seed-stage company. So, we are still very actively in the process of marching towards product-market fit, as well as marching towards the scalable acquisition channels that will just continue to bring more people into the product for us.

How long has the company been around?

My co-founder Samiur and I have been working on different companies for close to five years. The company most recent before Heyday was a company called Journal that we worked on for three years. It ended up being an undifferentiated productivity app that created all this manual work that we're trying to automate away from people. It was just adding to the mix. So, after working on that for three, almost four years, Samuir and I were like, "We are pushing a boulder uphill. This is not going to work. We need to figure out what is it that's unique about us, unique about our skillsets, that will allow us to bring something differentiated into the world." A year ago, we made the pivot from Journal to Heyday. So, we have now been working on Heyday for about a year.

I think many startups go through that. You know you're in the space and you're like, "Well, what does it look like? What's the right expression?" How many folks are at Heyday now?

The team is five people. So, my co-founder Samiur and I, and then we have three teammates, all of whom are software engineers.

Brief interlude where we talk about Sam’s dog who has her own Instagram.

I hear a squeaky toy.

I'm sorry. My little French bulldog puppy is squeaking in the background.

What's your French Bulldog's name?

Her name is Ellie. She's the sweetest girl. She has an Instagram handle @baadgirlellie, because that's equal parts Rihanna and WWE content. She's a very, very strong personality, but she's very sweet. 

My dog was the original love of my life. I’m a huge animal lover so anytime one shows up in a meeting I have to meet them. Thank you for introducing us to Ellie.

Back to the conversation.

What is your role at the company?

I'm the only non-engineer on the team. So, my role primarily looks like figuring out: how do we people aware of that this product, Heyday exists, make it exciting to them, make them see themselves in it, and then figure out a repeatable, scalable way to get those sort of folks who would be excited about what we're building into the product so they can start using it. The more succinct way of putting that is marketing. It's a combination of marketing and customer success that I spend the majority of my time working on.

So you're the only non-engineer...

Exactly. "Technically challenged" is the way I like to put it. I’m skilled in figuring out: what is the narrative that we're trying to put forward that we can use to get people really excited? I think the aspect of marketing that is most important at an early-stage company is understanding the pain point of the people that you're trying to serve with the product.

The majority of my day is spent having conversations with people who are at some point of using Heyday, whether they're just getting into the product or they're sharing feedback after having become paying customers. But the goal of it is to just, again, understand: why did they sign up for this product in the first place? What were they hoping for it to help them do? And then really just listen to that feedback and then feed it back into our product development so that what we're building is truly something that addresses their pain points. My skill set is being able to understand issues people have and then translate that to teammates in a way that we can build a product that addresses it.

Shaping the narrative is an important leadership activity including for startups trying to find product-market fit.

Exactly. In my mind, a startup is just a story. They are a series of stories that you're telling.

Startups are made up of stories you tell. And there are different versions of the story that you tell to different people. You're trying to tell the story to people who've never heard of you.

"Hey, there's this thing out there that will help make your life better." You are then trying to tell a story to employees and teammates of, "Hey, we are making the progress that we need to make to continue to help those people." You're then telling the story to investors of, "Look at all the stuff that we've accomplished. And just imagine how much more we could accomplish with your backing."

Have you been in a leadership role before?

This is the first time that I've been a co-founder of a venture-backed company. And I would say the flavor of leadership is a lot different there than my past experience of managing a demand gen team at a startup.

Can you talk about that difference? Because leadership versus founder leaders are actually quite different.

Yeah. I'll struggle to explain it because I'm just so focused on the founder leadership point right now. But if I can go back into my time machine, I was a demand generation manager at a company called Mattermark that grew to about 60 or 70 people. So, I was about 24, 25 managing a large team that I think grew to eight to 10 people of SDRs, of sales development folks. And the challenge of leadership there was, I would say, one of motivation. The name of the game in that role was making a lot of phone calls to sell a product to people who hadn't heard of it. And so much of leadership there was... Again, it's motivation, but also habit-forming. For many people, this was their first job out of school, so you're just trying to help be a good conduit into the workforce.

Whereas, now, as a co-founder of Heyday, our team is compromised primarily of senior folks, senior people who have worked in tech companies for many years in their career, many people who've worked professionally for longer than I have. So, I think leadership in this case is... The hardest part of leadership for me, I would say, is actually one of self-management and energy maintenance, and then communicating and just effective communication to the team, keeping everyone aligned in terms of what the biggest goals are and what we need to do to continue to march towards them.

Did you ever imagine yourself founding a company? Was that a goal?

It was not a goal of mine. I grew up in Northern New Jersey, and success looked like becoming a doctor or a lawyer or going to work in finance. I was a bit crazier than all those people. And I went to college and was like, "I will be the President of the United States." And after a couple of years of majoring in political science, I was like, "This is not at all what I wanted. These classes are boring. I'm not having fun with this at all."

My lucky break was when I met a friend, another student who had gone through TechStars, the startup accelerator. He introduced me to this world of lean startup methodology and startups in general, and said, "You should check out this website called TechCrunch." None of these are things that I knew about. And I just became so obsessed with the idea of building a company of my own, right? And playing a huge role in it. So, up until that point, no, I didn't think it was a possibility for me, back to what we were saying. With the examples that I had at that time of what is possible, starting a company was not possible for me. And then, after meeting this person, I was like, "Oh, yeah. I'm moving to California. I know what I need to do to feel fulfilled." And now I'm very much on that journey still.

What's hard about being a founder?

I'm taking a deep inhale as you ask, Suzan. I'll talk to people all the time who've never worked in startups, who've only ever worked in large companies. They're like, "Oh, what is it like working at a startup as a founder?"

Being a founder is like being on a rollercoaster.

I think that is the best way to describe it. There are days when you're like, "I am building something that I know for a fact will be a $1 billion company," when you're five people sitting in a room because something great will happen, you have a new customer come in, feedback is pouring in that's really positive. And then not even the next day, maybe just a couple hours later or even minutes later, the opposite will happen. A customer will churn, you'll get negative feedback. Something will break, you will ship a product with a new bug. There's a series of things that will go wrong, and the energy maintenance, I think, is a function of what stories you're telling yourself when those things are happening.

If something goes wrong and you think, "This is evidence that what I'm doing is not going to work," then your energy is depleted. On the flip side, if you're able to say, when things go wrong, "This has nothing to do with who I am or what I'm capable of. Something happened, and now we get to fix it..." How your energy will react, whether it will be depleted or not when stuff is happening, will be hugely impacted by that.

As a founder, you have to think about what stories you tell yourself, how you manage your energy.

I love that you talk about managing your emotions, we don’t talk about that enough. Leaders and especially founder leaders have a ton of responsibility and pressure.

Yep. Completely. I would say that I do a decent job of dealing with it. I have a bunch of friends who are founders. My co-founder is a very, very close friend of mine, so these are conversations that I have with people frequently and openly, at least in our private forums. But I think, again, it comes down to what is the story that you're telling yourself of pressure, even in this case. I could be to myself, "This is a five-person company. This is completely dependent on me whether or not this succeeds. So much of my identity is tied up to the success of what I'm working on." All of that. I'm feeling my shoulders tense and my chest is getting tight as I'm saying this.

The other way that you can have that conversation with yourself, though, is, "What an awesome position that I'm in to have the opportunity to work on something that is truly different, that is helping people, that is bringing a new flavor of something into the world." It completely changes your outlook and that feeling of pressure. And I'm not able to do that every day. There are definitely days where I fail to do that. It's very hard. It takes a lot of practice.

The thing that I found to be most helpful for me recently is, a few months ago, I saw started working with a coach. So, the story is a friend of mine who is also a co-founder, we were having a conversation. This is at a time when things for us were very clearly not working with Journal and it was time to make a pivot. But it felt like the end of the world for me. It was something that I had spent an hour... Not hours, years of my life working on trying to build. And I knew that we needed to make big changes. And a friend of mine was like, "Hey, I just started working with a coach. It sounds like you could benefit from working with a person as well." His name is Ben Easter. So many of the tools he's helped equip me with are the stories that I'm able to tell myself. And that has been really helpful for me.

In a role like this, you absolutely need to have some sort of external support. It sounds like you have that.

Yes. It is a combination of all of those things. It's a coach, it is friends going through the same situation, it is, in my case, a fiancé, who's very supportive in all that I do and listens to me complain and whine and cry all the time and is there for me, family members who I can share things with. I look to many places to get that support and encourage other people to as well.

You tweeted that only 1% of venture-backed founders are Black and that you're one of them. What was your experience like?

The story of that thread was: a couple of years ago now when George Floyd was murdered, I was sitting in the car with my fiance, overwhelmed with emotion. And it dawned on me that, in this privileged position of being a venture-backed Black founder, I had done so little to help other people and had been just so focused on my own experience and getting my own company off the ground. The story that I say to myself is, "If I can get this company working, I will be an example for so many other people who look like me, that this is a possibility for them." But I wrote that tweet just as a way to start shining light on other folks who don't look like the people who you would normally expect to see working at or building startups, just shining light on them and giving visibility.

The thing that I think is such a challenge as someone building a company is confidence, right? When you're building a company and things are going wrong, again, it is easy to tell yourself a story of, "What I'm doing isn't going to happen. It's not possible." So, the biggest challenge for me as a black founder has been: is it possible for a black founder to build a multi-billion-dollar company? There's a small handful of amazing people out there who answer that question definitively, "Yes, it is possible." But there aren't that many people. So, for me, the challenge always comes down to: do I have what it takes to accomplish this journey that I've set out on? I'm super fortunate and I have that strong support system that we were talking about, but it doesn't make it feel any less lonely at times.

When you're 1% of something, that can feel lonely, on top of loneliness that founders already feel.

Right. And that's why I have to make this work. I believe the role that I can play in the ecosystem that would be most impactful is building a company that is well-known, well-respected. And then, when someone who didn't even realize that building a startup was a possibility for them, sees my face and they're like, "Oh, that's cool," whether it's explicit or not, it registers in the back of your mind, "This is a possibility for me." I want to be the reason that some people can have that thought. So, that's something that really drives me.

It sounds like you wear it not like heavy or like pressure, but light and being an inspiration and as a very positive thing.

Yes Absolutely. It's not something that weighs me down, nor is it something that I'm even explicitly aware of every moment of every day. But the times when you have to draw into your energy reserves and say, "Why am I doing this? I could go do something else that's a whole lot easier and less stressful." Again, I try to remind myself, "No, this is awesome that I get to do this. If I do this well, here is what I get to unlock for the world." That is absolutely something that brings me levity versus feeling like it crushes me down.

It also sounds like you're working on a vision of something that’s important to you too, what Heyday is trying to accomplish is actually also important to you.

Absolutely. It's the combination of those things. It's, "What does this company like do for the world?" And if that's important to you, as the founder, that is huge, right? And then, beyond that, I get the added benefit of, oh, if I get to bring this company that does something awesome into the world, and I have my experience, that is doubly awesome in my book.

What’s the biggest challenge you're facing as a founder right now?

The biggest challenge I'm facing as a founder right now is identifying and building a scalable acquisition channel. To this point, we recently celebrated on Twitter the other day because we just passed 100 paying customers for Heyday, which was awesome. In years of working on Journal, we never passed, I believe, the 10-to-15-paying-customer mark. And just in short order, in a couple of months, we've reached 100 paying customers for Heyday, which is awesome.

The challenge is many of those customers have been brought into the product through unscalable means, through PR. Fast Company wrote this incredible piece about us. That drove a lot of traffic. We are active on Twitter. Folks on Twitter will find out about us and then come into the product that way. We partner with awesome Substack writers who mention Heyday in their newsletters and drive their subscribers into our product. That has driven a lot of like signups for us. None of those things are scalable in the sense that they won't bring millions or tens of millions of people into our product. So, now we are going through the process of actively experimenting with channels that would work, given the nature of our business, the nature of our product, and other things like that.

We don't have one of those working yet. We're starting to see signs of things... An example of a channel like this would be Google Ads, let's say. Billions of people use Google. If we figure out a profitable way to turn Google Ads into an engine of growth for our product, this will put us in a really good position. We're not there yet. So, the challenge for me is just figuring out which of these channels can we get working for us to drive more users and customers into our product.

It's harder than people think. It's really an accomplishment. Even though this might sound small to some people, it’s huge, especially after the years with Journal only getting to 10 or 15 paying customers.

Thank you. Thank you. It was a grind. It was a grind, but we made it happen.

Are you looking to raise more money in the near future?

We have a strong, long runway right now, so we're not actively in the fundraising process. But our goal is to make ourselves a super attractive target for a Series A investment. And the North Star metric that we have for that is the number of paying customers. So, we are trying to get that scalable channel working so that we can get that number of paying customers into the product, which will make fundraising really straightforward for us.

I have friends who have raised money. Fundraising can be an all-encompassing, different kind of task.

Yes, completely. Fundraising is like a sales process, right? Where in the majority of conversations that you have will be nos. If you talk to 50 investors, 49 will say, "No, the timing isn't right." The way to turn more of those nos into yeses or make the process easier on your individual energy level is to enter those conversations with conviction in your track record, in your accomplishments, in the business's trajectory to that point. And that's what we're working towards right now, is just putting ourselves in a strong position for those conversations to be fruitful for us.

That's a great strategy. Is there anything that we haven't talked about in terms of leading and founding a business that’s important? 

I think we did touch on this, but just expanding on it, I think the importance of having a strong support system in the endeavor that you're working on is the thing that I would encourage people to be very intentional about, in part because I learned the hard way of what it's like if you're not intentional about it. I mentioned having a coach before and having conversations with other founders and actively leaning on family and partners and other things like that. That was not something that I did at the beginning of my startup journey. And then you end up in this very isolated, lonely place. So, my encouragement for people is to be intentional about... Your support system will look very different than mine, depending on what it is that you need. But my encouragement is to be intentional about where are gaps that you have as an individual that could be filled in confidence or actual skill levels, and then seek out the people to help you do that.

One of the cool things as a founder is people are excited to talk to you, more so than, I think, if you're doing anything else, because whether they've been in that position themselves or whether they have never even considered starting a company, you are looked at as someone who's doing something that is quote-unquote risky and that takes a lot of confidence to do. And because of that, I would say the default way that people interact with you is from a place of, "How do I help? How do I help this crazy person doing something crazy succeed in what they're trying to do?" So, just tap into that. Be intentional about how to build your support system, and then enjoy the luxury or the privilege of doing something that other people will just want to be helpful in.

What to read next

Managing your emotions

The changing nature of startups

Year two of the startup journey

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