Bobby Pinero, Co-founder of Equals

Bobby was one of the first folks at Intercom, helping it grow from $1M to the juggernaut today. He’s now working on Equals which is the only spreadsheet with built-in connections to database, versioning, and collaboration.

How does early stage startup life affect your mental health?

Two sides here.

On one side, I love working at this stage. Some of my best work memories were from when Intercom was tiny. And now in founding Equals, even with the demands and relentlessness of the work, it's a huge benefit to my mental health. I feel like I'm doing exactly what I'm supposed to be doing. I get to work in creative ways every day. I get to put a part of myself into the world. Equals is an expression of me and the rest of the team. And when our customers get value from Equals, that's especially magical. I get a lot of joy and fulfilment from building Equals.

On the other side, frankly it's terrifying. Building a company is a vulnerable act. It's scary and hard to put yourself out there. As a founder you have an idea for how the world should work and you dedicate a lot of time to bringing that into existence. You're either going to be very right or very wrong. That is scary. It's easy to doubt yourself. It's easy to look around at everyone else and think you're doing it wrong. It's easy to question whether all the sacrifices you're making in your life are worth it. At least that's what comes up for me.

But these are the things I question about myself in general. I tend to doubt myself. I tend to think I'm doing things wrong. I tend to look around and think everyone else has it figured out. Starting a company, or any other challenge in life, tends to apply a magnifying glass on your innate patterns. Any cracks get exposed. And so I view this as an opportunity for me to confront these patterns. To confront my doubt and fear. To learn why I feel them. To welcome and integrate them into how I work every day.

Does any specific anecdote come to mind? How did you navigate that?

I think a lot about uncertainty. I think it's probably one of the most difficult things that we as founders have to navigate and manage every day. Uncertainty about your idea. Uncertainty about the future. Uncertainty about having a job. As a founder you're inherently sacrificing stability in a huge part of your life - work. That can be really unsettling. That was probably the most uncomfortable feeling for me when I first started Equals.

I try to ask myself, "what is this uncertainty trying to teach me?" There's a great parallel to life there. None of us know what's going to happen to us tomorrow, in the next year, or in the next decade. Yet we try and try and try our hardest to assert control. We make plans. We tell ourselves certain things will happen in the future if we do things now. We fight for control. But in reality we don't have any control. You could've spent 10 years building a kick ass business only to have COVID wipe it out. And so, for me I try to see the uncertainty of my startup as practice for life. And life as a practice for being a founder. The biggest shift for me came when I realized that it just is uncertain, and that's ok. Because life is that way too. And so rather than trying to fight that uncertainty, I welcome it into my life. I try to find comfort with it. I laugh at how much effort we all put into trying to control the future. Isn't it cool and brave that we as founders work so hard and put ourselves out there, without knowing what the outcome might be? I've found that to take the edge off.

Now that doesn't mean I'm not trying. You better believe that at every point along this journey I'm doing all that I can, I'm making the best decisions that I can at any moment, to make Equals (and my life) a success (however you want to define that). Giving up control doesn't mean not trying. But I find a lot more peace in doing the best work that I can, trusting, and then detaching that from the outcome.

What helps you manage your mental health?

Therapy has been huge for me. I've been in therapy for the last 5 years, every week. I've learned that many of our patterns at work, whether we like it or not, have nothing to do with work. They have to do with who you are, what you were taught, how you were raised, etc. Bringing those patterns and behaviors to your awareness is insanely powerful. It’s probably the highest leverage thing that you can do for yourself. I think I’d have saved myself a lot of heartache, anxiety, doubt, etc. had I learned much of the lessons I’ve learned in therapy, earlier. And I'm confident it's made me 100x more effective in my work. I'll caveat this by saying that there are lots of different types of therapy. It took me trying many different types to land on one that worked for me.

Sleep. It's a non negotiable for me. I need to sleep 8 hours every night. Everything gets way harder when I don't sleep the full amount. I know I do my best work fully rested. I know I do my most creative work fully rested. Everything is harder when I haven't slept enough.

Breathwork. I tried meditation for a while. I just couldn't stick with it. I might someday revisit it. But I really love breath work. There's a great app called Othership that I'd highly recommend for anyone curious to try. I do some sort of breathwork practice every single day.

Caroline Clark, Co-founder of Arcade

Caroline has gone from marketing at Atlassian to investing at Sequoia to building Arcade. Arcade lets you add interactive snippets of your product to your website, blog, or social media, so customers can try before they buy.

How does early stage startup life affect your mental health?

In some ways building a company is a Herculean task that isn't fully absorbed until you are in the motions of doing it — not only are you building a plane while flying it, you are usually a first time pilot and praying that you won't crash. And when mistakes happen, as they inevitably will, as the plane begins to tilt downward, you are on the phone with an experienced pilot who is telling you which controls to push while beginning a rapid descent. Then your phone starts ringing on the other line and the airline (in this case, a customer or an investor) is asking why your plane is not going at the speed that they expected to. But you press the right button, explain to the customer that the speed will return to normal, and you can go back on autopilot for a while. But talk about a stressful job! So the impact on your mental health is pretty harsh. It is a constant game of overcoming doubt and finding out ways to be resourceful. In this vein, I do think some founders do better than others — in particular, ones that are comfortable with constant chaos, and being resourceful to a point of knowing which fires are important fires.

Does any specific anecdote come to mind? How did you navigate that?

I went through a particularly rough period with my first fundraise in spring of 2021. I was a solo female founder, and recently went through a personal and cofounder breakup (which I don't recommend to do both at once at the same time). It was also in the middle of the pandemic during a time when things were particularly locked down so I had minimal personal stimulation. It was awful, as I was being rejected all day and then had dinner alone, and then had to figure out in the evenings after that how to get more meetings with a VC that would take a chance on me. I actually powered through that by going into survival mode by only focusing on the things that I needed to do for the next day. I didn't even know how tough that period was until after the fact. Luckily things worked out — I found a great partner in Aditi at Upfront, recruited a great team, and have a wonderful personal partner who is very supportive of my journey. Ironically, my second fundraise was way easier during the market crash because I had more positive data about the business. It goes to show how everyone's highs and lows are very personal.

What helps you manage your mental health?

The formula isn't complicated — I make sure I get enough sleep, work out every day, and I don't drink. I do say no to a lot of things to preserve my sanity (I probably won't be that person at the bar on a weekend, or at every wedding or trip). The challenge is being disciplined enough to say no and ensure that I carve out time for sleep and workouts. I tried meditation but it doesn't work as well for me. Again this is all super personal. I happen to really need sleep and I am pretty sensitive to adverse effects of alcohol, but I know plenty of super social founders — some of us get energy from being around others.

Steve Klein, Product at LaunchNotes

Steve has multiple acquisitions under his belt, including StatusPage which was acquired by Atlassian. He’s now doing product/growth stuff at LaunchNotes, an app that modernizes the product development cycle with continuous change comms, shareable roadmaps, and actionable feedback.

How does early stage startup life affect your mental health?

The hardest thing about working at an early stage startup is the work is never done. You could work all day every day and still there would be more to do. At times when you're feeling particularly energized about work you can fall into a pattern of just working all day. This is especially true for people who work at home. The boundary between work and home is blurred, so you can find yourself picking up right where you left off after dinner.

Does any specific anecdote come to mind? How did you navigate that?

A recurring anecdote for me is that I know I'm not in a good spot when I start saying "fuck you" to inanimate objects. Drawer that the trash can is in gets stuck? Fuck you. Almost knock something over? Fuck you. For me it's a tell that I'm redlined to the point that I have 0 time or energy for everything else in life to not go perfectly.

What helps you manage your mental health?

For me it's a constant battle of just doing the basics. You have to prioritize taking a step back and going for a walk. You have to find the time to exercise. You have to just close the laptop at a reasonable time and unwind. The siren song of "but if I just finish this one thing I'll finally feel caught up" is always there. You have to choose to ignore it and listen to your body.

Rudy Lai, Co-founder of Tactic

Rudy went from automating customer engagement and pricing in banking to building Tactic, a data vendor that you can customise. Off the back of their first few customers in sales and marketing, they have just raised their first VC round from Index Ventures.

How does early stage startup life affect your mental health?

The purpose and control is really the bright side for me. There is no comparison to waking up every morning being excited to build on your ideas, frequently coming from a bad night's sleep because you can't wait to start the next day. On the flip side, your feelings can change from minute to minute. One minute you are about to change the world, and the other minute all looks lost. I would quote my dear friend (a luxury fashion founder) here – "startups are the only place where, at the lowest points, you can look forward to a high point later". It's not for the faint hearted, but the upsides outweigh the downsides.

What helps you manage your mental health?

Lots and lots of exercise. Having a great co-founder. Speaking to lots of customers and understanding what makes them excited, focus on that excitement. Using the variety of work that a startup presents to break up the routine a bit – for example, if you are tired of coding, you can always go make some cold calls, vice versa. Try to do one thing a day that is a 'sure win': a founder's job is to constantly solve the hardest problem in the business. But when you are tired of it, you can always go do a very small task to bring yourself back in control – like tidying up the product roadmap, or updating Salesforce – small things that bring you a sense of achievement!

Kostadin Kolev, Co-founder of Calliper

Kosta’s had a bunch of product and operator roles over the years, and to top it off, has organised the first hackathon on a plane. He’s now working on Calliper to make data accessible and actionable for every team, and they’ve recently gone through Sequoia Arc.

How does early stage startup life affect your mental health?

It forces you to be more resilient. Due to the sheer amount of shit that can happen in a company on a day to day basis, you can yo-yo from win to failure so quickly. That can be really challenging and you need to create a sense of balance and equanimity to deal with this turbulence.

You can also end up being cold and disconnected as a founder from your day-to-day life. If you imagine the classic 9-5 work life, most people’s day-to-day existence is fairly consistent and similar. Early-stage startups are relentless, and sometimes it’s really difficult to maintain friendships and relationships. A few founders I’ve talked to mention how you can be disconnected from others and need to make sure you make time to reconnect and solidify your valued relationships because, over time, you might end up quite isolated.

Does any specific anecdote come to mind? How did you navigate that?

Ah, there’s so many. One of the worst ones I’ve had recently was parting ways with my old co-founder. You’re in a commercial and professional - and yet deeply personal relationship with your co-founder. When that’s unsteady, it can be stressful. Work can become even more all-consuming, especially as you likely spend your more time with your co-founder than your romantic partner. So, if things are rocky, you can be really unsettled and lose a lot of stability in life.

You have to really focus on self-care to navigate that. There’s the whole aspect of your “rings of influence”. At the very edge are all the things you can’t control and you have to let go, then there are the things you can influence, and then there are the things you can actually control. Spend your energy on the things you can control. Maybe dedicate some time to the things you can influence - but if they don’t go the right way, try not to let that get to you.

What helps you manage your mental health?

I need to have consistency and routine. I need to make sure I meditate every day, exercise every day, and have at least 1 break to go outside and go for a walk. Those would be the top 3 things. Aside from that, I find healthy eating and not drinking during the week to help because that has a big impact on your sleep and rest.

Once in a while, it’s nice to disconnect and party too. It’s just about being sensible and mature most of the time because many founders have intense and addictive personalities, so you can easily fall into bad habits around blowing off some steam.

David Newell, Co-founder of Unflow

David has gone from stints at Basecamp and Intercom to taking Unflow through YCombinator. Unflow helps you build mobile app experiences, without code.

How does early stage startup life affect your mental health?

In every way possible. One of the most immediate and consuming differences I first noticed was the stress of knowing that everything depended on me. If I wasn’t working code wasn’t written, I had to be the one to make the final hiring call, there was no one else around responsible for your first major security vulnerability or scaling challenge. If I couldn’t do it, it wasn’t going to be done. As someone who hadn’t had that level of responsibility before it was a real shock.

The knock on effect of all that can be overwhelming. You end up putting so much time into work that you start to sacrifice all the other aspects in life that kept your mental health in check - your relationships, hobbies, exercise.

Over time you learn to deal with these things. Every new challenge seems insurmountable in the beginning, but once you’ve solved enough “impossible” problems you learn to become more comfortable with the idea that everything will eventually come to a conclusion and that just have to continue on with everything else in spite of the “impossible” problem du jour.

Once you start to internalize that it becomes a whole lot easier to step away from work when you need to. It’s ok to close the laptop sometimes and make space for all the other important elements in life.

Does any specific anecdote come to mind? How did you navigate that?

Probably one of the toughest points in my journey was stopping work on our second product. Things weren’t growing as we’d expected them to but switching tact also seemed like a terrible idea given we were running out of funding and probably wouldn’t have long enough to kickstart something else to the point that it was investable. It felt like an inevitability that there was no way we would succeed.

Quite honestly I handled it terribly for over a month. I spent all my time questioning if the whole experience ended right then whether I’d have considered it worthwhile. I went around in circles trying to weigh up all the good and bad, at what time in the past would have been best to call it quits, what little else could I get out of the time left, etc.

Eventually I changed my refrain to something more along the lines of “well it isn’t over yet, so you might as well try something different”. That led to a change in approach - things became less about succeeding and more about learning. Which in turn led to much more interesting avenues, conversations and eventually products. It turns out that was a much better mindset to be in during the early days, and we just needed to make sure we kept going long enough to reach it.

What helps you manage your mental health?

People often suggest separating yourself from your company but I find that almost so hard to do that it’s not worth the effort. One of the most positive practices I’ve put in place is to focus on the progress I’ve made in the areas I’ve committed to.

It is inevitable that things are constantly going wrong at your company - someone left the team, a customer didn’t sign, there was a big security issue. So much bad happens that it’s too easy to forget that some good things are happening too.

You need to separate what you want from what is happening and focus exclusively on the former. What do you care if Notion raised $100 million, if all you want is 5 paying customers. Should you really get upset if Superhuman’s waitlist is 10,000 users long if you just hired a much needed engineer.

I’ve started to set goals about what stage I can reasonably expect the company to be at given our size and trajectory, as well as my own personal ambitions. I spend much more time appreciating at our size we cannot take on everything and will inevitably fall short in some areas. That just means I’m choosing to spend my time on my other commitments and only evaluate my efforts in those areas. I have a much better appreciation that whatever I do commit to turns out reasonably well, and usually when things are going badly within the company it’s a symptom of not having enough resources to focus on it. I find that I’m much happier and feel more accomplished when I’m not comparing myself to the world as a whole or even the company as a whole, and instead look at how the things I actually did turned out.

Elliot Gibb, Co-founder of Mercu

Elliot was a designer at Grab (the Uber of South East Asia) for a while before venturing into Mercu. They’ve raised from Sequoia Capital India.

How does early stage startup life affect your mental health?

Massively. I assume that most founders, like me, start out having a big ego. After all, we’re the ones that need to believe that we are uniquely positioned to solve a hard problem.

However, my ego was in part built on the foundations of previously working at a large, successful tech company. There I benefited from established product-market fit, exceptional colleagues, and regular pats on the back to feel the sense of fulfillment that is necessary for my positive mental health.

In the early days of your own startup, as you search for the mythical product-market fit, you are starved of all this, and your mental health takes a battering as you realise you aren’t the hot shit you imagined. Until you recalibrate what gives you fulfillment, the impact on your mental health adds up.

Does any specific anecdote come to mind? How did you navigate that?

In my old life working in a tech company, if a product launch didn’t go the way we as a team expected it to, we’d run a retrospective, go for team drinks, and collectively share in the pain and repercussions. Perhaps you’d even kid yourself that if marketing had just spent a few more dollars, or if engineering didn’t descope that key feature, it wouldn’t have failed.

But at your own startup, the only person to blame is rightfully yourself. You had the original insight, you descoped the features, you didn’t put the marketing dollars behind it. When we launched the v1 of Sample and realised within 48 hours we’d built the wrong thing entirely, there was nowhere to hide, it was my fault and it hurt badly.

In retrospect, it hurt because I hate being wrong and I knew that I’d skipped corners in the process. Going forward, I’ve had to learn how to be comfortable with being wrong, but only if I know in the process that I’ve done absolutely everything in my power to get it right.

What helps you manage your mental health?

Having a co-founder!

Honestly, I would’ve given up long ago without Jascha. Nobody on your startup journey, including your closest friends and family, understands what you’re going through like your co-founder.

Popular knowledge tells you to find a co-founder that compliments your skills and fills in your weak spots. Equally important to me is to find a co-founder that you can go for a long walk with or shed a few tears on when things don’t work out how you expected them to.

Wrapping up

I'm incredibly grateful that friends took us up on talking about their experiences, and I can't thank them enough for taking the time to reflect and be vulnerable. It's so important we take steps as a community to openly share our experiences, and I hope you found this as rewarding to read as I did.

Note: The cover image was made by iterating on a generated Wombo Art