The Proof
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Harry Ritter, Founder at Alma

 
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Harry Ritter is the Founder & CEO at Alma, a co-practicing community of therapists, coaches, and wellness professionals. Alma is pioneering a new practice model for therapists to elevate the therapy experience and simplify access to care. Alma has raised over $12.5 million in funding from Tusk Venture Partners, First Round Capital, Sound Ventures, Primary Ventures, and Box Group.

Prior to founding Alma, Harry served as Medical Director & VP at Oscar Insurance, a pioneer in the modern health insurance space. Harry holds a BA from Harvard, a JD from NYU, and an MD from the University of Miami.

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On his morning routine. I’m an early to bed, early to rise kind of person. I’m usually up between 5 and 5:30 each morning and spend the first hour of my day reading, getting the day organized, and helping my kids wake up - I have two boys, 4 and 2. I spend the next hour with them and my wife, which is kind of our special time each morning. I don’t always get the opportunity to get home before they go to sleep, so having that dedicated time each morning with them is really awesome.

One thing I’ll do every morning is pray, which I’ve been doing since I was 13 and kind of acts as my mindfulness routine. I think it’s important to have a moment each morning to hit pause, contextualize, think about gratitude, and center myself to prioritize what matters from the beginning of the day. It really helps me set the right tone for how I interact with people and deal with challenges as they come up. Then I get out the door and get to it.

On combating pressure in tech. What attracts a lot of great talent, capital, and interest from the venture world is this feeling that great things can happen quickly - that you can transform industries and lives in an incredibly unique way. Josh Kopelman made this point a while back that First Round, as a venture fund, sells jet fuel. You’re trying to shoot for the stars, which invariably creates this enormous pressure to expand, grow, and experiment.

It’s a double-edged sword because what attracts us to this space is also what makes it so challenging to operate in. For me, there are three things I always consider that have been helpful. The first is having control over your time. There will be weeks that you’re just going to work 80 or 100 hours, but it helps to decide which hours you spend working so you can still make time for the things that matter outside of work, whether that’s spending an hour in the morning with my kids or taking a day off. Having the ability to block your calendar in a way that lets you control and structure your time is extremely powerful.

The second is clearly distinguishing between work and non-work time. In my case, that’s not bringing my phone into the bedroom or turning it off once a week. If you don’t create that barrier and are always on a little bit, you don’t have the opportunity to reset. Finally, a lot of folks aren’t transparent about navigating this difficulty. Often, folks end up working like crazy and just not acknowledging it. Calling it out and being transparent about your work can be pretty powerful.

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On building culture from the top. Many people in tech have this obsession with being perfect and sometimes just fail to forgive ourselves. By not forgiving ourselves, we create this really vicious cycle. As a company, it’s all about culture and how leaders set that culture. It’s critical for folks to be able to say, “Hey, this was a moment where I needed some extra time, or needed to call it early because I’m not performing.” It’s okay to call it for a day and come back refreshed. At the end of the day, the trains will still be running. It’s important to have that measure of transparency, self-forgiveness, and culture that sets that standard from the top: that perfect is not the goal. The goal is constant improvement.

We’ve really tried to develop a culture at Alma where we celebrate and care about the team as people and acknowledge that we’re stronger together, we’re here for each other, and there's always going to be ups and downs. You need to have the grit and resilience to say, “Today’s not going to perfect, tomorrow’s not going to be perfect, but we’re all pushing to build something we believe in.” 

On challenging stigma in mental health. The world has evolved. I’m optimistic about the trends we’re seeing in the broader cultural and social landscapes around talking more openly about mental health and addressing stigma head-on. You see so many more leaders in pop culture and business talking about their own stories and sharing them with humility and pride. I couldn't be happier about being in this space right now. Things are definitely trending in the right direction. 

At Alma, our strategy to combat stigma focuses on three things. The first is design. We try to design great experiences that make people feel proud that they are taking an important step in working on their mental well-being. This spans digital tools, photography, brand, and physical spaces. All of our design communicates that mental health is important and that we should be proud to work in this space. 

Second, we’ve always believed in the power of storytelling and will continue to double down on that as we scale. The ability to connect with providers and learn their stories — understanding the journey and narrative of the person you’re seeing — can make people feel more comfortable about seeking care. Lastly, we focus on education and community. We’ve hosted a ton of events here at Alma to create opportunities for consumers to interact with providers and for people to discuss these topics in a forum that is progressive, safe, and incredibly thoughtful.

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On his keystone habits. I break down my habits into daily habits, weekly habits, and special times throughout the year that allow me to recharge. For me, an important daily routine is creating space every morning to be mindful and use prayer as a way of reflecting on the gratitude that I have for the incredible things in my life. Carving out that time to be with my family and having that touchpoint every day with them is super important. At the end of the day, creating the same space to unwind, put the day away, and get ready for the next one is also key. 

On a weekly basis, I make sure to block out time for exercise. I try to get to the gym at least two mornings a week to give myself an opportunity to focus on my physical self. I also turn off my phone every Friday evening through Saturday night so I have a full day to disconnect from tech. On a yearly basis, one thing that I try to preserve is making time to get away, whether that’s a long weekend or a short trip with my family. Travel and separation are critical to reset mentally. I really try to encourage that for the team in order to identify moments of recuperation, not just in a day and week, but in the context of a quarter or a year.

On dealing with the pace of New York. I’m from California, so I grew up with more space and definitely had more of an outdoors experience where I could get away into nature. I think it’s important to find your sanctuaries in New York. The city is dense with all kinds of nooks and crannies to explore, and there’s something that works for everyone. Whether it’s a gym, your local bar, or coffee shop, that density creates opportunities to find your sanctuary. Personally, I love the park on the West Side Highway which is right on the water and is a bit quieter. It’s a beautiful spot ten minutes from my apartment where I can make space for myself. I also try to get out of the city on weekends when I can, especially in the summer. 

Depending on your commute, I find that is also a great time to engage with a podcast or audiobook. That can be a powerful break in the day, especially on my 20-minute subway ride to the office most mornings. I’ve tried to move away from being glued to my email and phone, and use that time to read or listen to something. For music, I’m old school - I listen to a ton of jazz. For podcasts, I used to be really into Serial and I’ve always enjoyed How I Built This

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On developing confidence. I think every phase is always the hardest because it’s the “new thing.” I just became an uncle last week and was reflecting on the experience of being a parent for the first time. As a parent, you can reflect back on your first child and think to yourself, it’s so easy with your first kid. The thing behind you looks easier because you’ve accomplished it already. But in the context of that moment, the thing is new and you’re constantly learning. At Alma right now, we’re growing quickly with a lot of new team members joining and thinking about how our culture scales. This is definitely a whole different type of stress than I’ve experienced before. 

The good thing about looking back as you move through these phases is that you start to develop a measure of confidence. You think to yourself, “I thought it was hard, I didn’t know how to do it, but I did it and got to the next stage.” You start to build this track record to look back on. When you build a business, you obviously want to put out a product that matters and is meaningful, but you also want to build a company where people are excited to work. People are really taking a leap of faith with you and I’m definitely feeling that right now. You really want to do right by the people that are signing up to be on this journey with you.

On his nightly ritual. When I was starting Alma, I got much more regimented about reading at night. I spend the last hour of my day in bed reading a book. We don’t have a TV or phones in our bedroom, only books. I also only read fiction at night, which is a great opportunity to engage with an alternate reality that transports you to a different place, time, and set of characters. 

Returning to this idea of creating space in your day for yourself, reading is a great way to make space and be 100% present. Fiction lets me become engrossed in a great story and every night I get to come back to it and detach from whatever happened that day. Right now I’m reading Steinbeck’s East of Eden, which is pretty incredible, and right before this I read Caine Mutiny by Herman Wouk, which has found its way into my all-time favorites list.

Harry Ritter, Founder & CEO at Alma