How She Creates an Affordable AI Coach — in Your Hand
Q&A with Dessy Levinson, Founder and CEO of CRATE.COM
Originally published on Medium, this is the first piece of the Entrepreneurship of Life series, a collection of interviews with immigrant startup founders, venture capitalists, and tech business leaders.
As a psychology major, seasoned technologist and venture investor, Dessy is exploring a drastically different approach to personal coaching, powered by technology and data. She also, with refreshing candor and vivid storytelling, reflects upon the challenges and growth she went through decades ago, as a young immigrant new to the Big Apple.
Dessy Levinson is the founder and CEO of crate.com, creator of the CRATE Mind Framework, a narrative awareness coach, and an early-stage investor and advisor. Previously, Dessy served as Managing Director at 645 Ventures, where she invested in early-stage consumer startups and frontier technologies. Her mind lives at the intersection of psychology, design, and early-stage startups, while her body resides just outside NYC with one husband, two children, and three cats.
D: Dessy Levinson (Guest)
K: Keyi Wang (Interviewer)
Building A Mental Health Startup During the Pandemic
K: What is CRATE exactly? How did this idea come into being?
D: One simple way to think about it: CRATE is a personalized digital vitamin for your psychological wellbeing. It caters to people who are overall mentally stable and want to be proactive about maintaining and improving their mental health. It does so by first understanding who you are and then providing customized coaching.
As a venture investor, I was fascinated by a number of direct-to-consumer brands that emphasize personalization, such as Care/of — a personalized vitamins brand catering to each consumer’s lifestyle and needs, Prose, which offers custom hair products, and M.M.LaFleur, which serves as women’s personalized stylist. Deep personalization has permeated various consumer product segments but so far remains scarce among mental health and wellness services.
I also noticed that while many mental health startups address people’s reactive needs such as coping with anxiety, those of us who want to proactively care for our mental wellbeing generally lack on-demand access to personalized resources. Even those with a therapist can’t call him or her out of the blue just to share their baseline emotions. Conversely, without a clear view of their clients’ baseline, therapists and coaches have to work so much harder to guide them toward a sense of well-being.
So I started envisioning an app that would help people practice “mindfulness” in a customized way and show users a snapshot of their mental state in the past, present and even future. CRATE was that brainchild.
K: Why does CRATE emphasize proactive mental care and make this its focus?
D: It is much easier to work on improving mental wellness when things are going relatively well, just as physical fitness tends to work better when we’re not sick. For apps that deal with anxiety, depression, addictions etc., user attrition tends to be high, as mindfulness becomes harder to build and maintain once people are already in a crisis mode. Going that extra mile on good days to immunize against future mental traps works better than digging ourselves out of holes on bad days.
K: CRATE is more of a mental nutritionist than a doctor.
D: Exactly. We designed the app to meet you wherever you may be at this moment, but we know you’ll have an easier time building habits if you’re proactive, rather than reactive.
K: We have seen a variety of tech-enabled business models in the mental wellness space, such as online therapy platforms (e.g. TalkSpace), prescription digital therapeutics (e.g. Pear), and mindfulness tools (e.g. Calm).
What do you think is still missing from the landscape, and how would CRATE help fill that void? I know you talked about personalization and proactivity, anything else?
D: Most existing offerings belong to one of two camps: emergency self-help, and tools for emptying one’s mind — such as meditation or sleep aids.
Focusing on the second bucket, I distinguish between mind-emptiness and mindfulness (or “mind-full-ness”). The former refers to calming one’s “monkey mind” and detaching from thoughts, which can be achieved through practices like yoga and meditation. Mindfulness on the other hand involves introspection and a different way of engaging with the world.
Mind-emptiness can be a path towards mindfulness, but it is not the only one. Alternatives may include, for example, reflective reading or writing, creativity, and deep conversations with people. CRATE is one such alternative, a more cognitively-engaged path toward mindfulness.
K: How would your technology set out to understand subtle and fickle human psychology and drive your personalization efforts?
D: We humans are complex, but not infinitely so. As a starter, there are limited variations of personality traits, and we have found personalization based on measured traits to be effective.
Unlike traditional personality tests such as the well-known Myers-Briggs Type Indicator (MBTI) framework, we do not measure people with static labels; instead, we see individual personality as dynamic: influenced by genetics and circumstances, but also able to evolve.
We also recognize that personality should be measured on a spectrum rather than in binaries, such as extrovert vs. introvert. Furthermore, many personality traits are interrelated in “cluster” patterns — when one trait moves, others might move with it. We have started tracking a large number of traits and mapping out how they relate to one another.
We use an onboarding system to generate a decent snapshot of who you are (at the moment), but that is just the start. We grow and augment that knowledge of you as we interact, the same way another human would get to know you over time. We then customize our content and interactions with you based on a comprehensive and real-time picture of your personality, moods, and internal narratives.
K: Could you describe the customized service you offer to users?
D: CRATE is our wellness framework. We know that when individuals align internal Clarity, Regulation, Agency, Trust, and Energy, they report lasting states of wellbeing or flow.
We’ve found ways to measure and correlate your in-the-moment states (how you feel now) with longer-term traits (how you’re likely to behave later), and we deliver content and behavior design that can nudge you toward becoming the person you aspire to be. What’s more, we know that people’s relationship with technology is becoming ever more strained. So we’ve created a beautiful app that will reduce stress rather than increase it, help you understand your psychology rather than exploit it, and be that one moment of screen time you won’t regret.
K: You have also started CRATE Coaching, a sister platform of CRATE for one-on-one therapy and coaching. How do you expect CRATE to balance technology with human service? Would you put more weight on one versus the other?
D: My original vision for CRATE was a technology-only platform, but the pandemic has made me realize how crucial real human connection is to people, especially during emotional turmoil.
After the onset of COVID, people who had heard about CRATE started reaching out to us for help, but our app was far from ready back then. As a result, I decided to take on personal coaching to both help those in need and prove the efficacy of the CRATE framework.
This experience revealed to me the critical importance of the human-to-human component. While I spend a lot of time strategizing with my coaching clients, I tend to notice the greatest changes in them during interactions that are less objective-driven and more about presence and connection.
As a result, we’ve begun working on incorporating the “human” piece into our tech platform. Even the best 3D-animated AI cannot deliver the same energy and warmth that humans can just by looking into each other’s eyes.
I still think of CRATE as a “technology-first” platform, but no longer “technology-only”. Human service will evolve to be a key supplement to our tech-driven core offerings.
K: What has your experience been like jump-starting CRATE during the pandemic? What challenges and opportunities did you encounter?
D: If anyone were to start a business during the pandemic (which I don’t really recommend), building a mental wellness tool is probably one of the most serendipitous options.
In my case, developing the CRATE framework and using myself as a guinea pig enabled me to better cope with the stress of building a pre-seed startup, as well as help my friends and family. The opportunity to support others via CRATE Coaching has also been a gift. Seeing the tangible and immediate impact we could generate on those in need charges me with energy and keeps front of my mind why I set out to build CRATE in the first place.
I have been extremely lucky to have some phenomenal advisors, such as David Pezenik (a tremendously respected psychotherapist who implemented Google’s psychologist-in-residence program) and Rachel Rider (one of the best somatic executive coaches out there). Without their invaluable support, I could not have got CRATE off the ground at any time, let alone during this strange year.
The pandemic has also had a focusing effect in that it eliminated a lot of noise and made our priorities clear. When building a startup, it is easy to get wrapped up in the outward affirmations of success. But as the pandemic hit and the regular bustle came to a screeching halt, the one priority that remained was to help people in the best and the fastest way possible.
K: From a business perspective, how do you plan to capture value? How willing and able do you think people are to pay for services like CRATE?
D: The pandemic has significantly raised people’s awareness to the importance of mental health, of controlling what happens between an external stimulus and our response. The digital mental health market is huge and growing exponentially, and we are iterating to develop an optimal pricing structure that balances profitability with inclusion and accessibility. We are well aware that economic and racial disadvantages carry with them a disproportionate amount of psychological challenges, so we want to ensure that we build a platform that is accessible to all.
The Venture Investor Perspective
K: What have you learnt from your past experience as a VC veteran that you are now applying to your own business?
D: My VC perspectives have been a bit of a double-edged sword, to be honest. I try to embrace my passion and creativity in building the product, but I also occasionally put my critical VC hat on to think through how investors would view the business, what KPIs we need to hit, and so on. The two sides can sometimes get in each other’s way and require a balancing act. But my network from the VC days has certainly proven an invaluable asset, especially when it comes to advice and support.
K: VR/AR/XR was a key area of your focus when you were a full-time venture investor. Do you see applications of such technologies in digital mental health?
D: Absolutely. There have already been novel use cases, notably in meditation and anxiety treatment (e.g. Healium); VR is a great way to help people become immersed through beautiful visuals and experiences.
As for CRATE, we decided to build a mobile-first platform for maximal accessibility. Once we have proved effectiveness, VR/AR and wearables technology will be a great future addition to our toolkit. I’m a total geek at heart, so machine learning and spatial computing are in our DNA; we are already experimenting with wearables integration and looking forward to AR glasses. But technology can and should first meet users where they are, then lead them to even better experiences.
K: Can you share with us one venture investment you have made that is especially memorable to you?
D: While I’m genuinely proud of every one of 645 Ventures’ portfolio companies, MM.LaFleur is particularly close to my heart and relevant for CRATE. It’s a direct-to-consumer clothing brand that’s also so much more. I remember a conversation with Sarah LaFleur, the founder, back in 2014; she said that the most important thing about a woman should never be her clothes. I found it especially profound coming from the founder of a fashion brand; indeed, the core message from MM.LaFleur to its customers is: “you’re so much more than what you choose to wear. We’ll take care of your outfit, so that you can go and conquer the world.”
Partnering with MM.LaFleur has taught me a great deal about the relational trust between a brand and its customers, as well as about personalization. MM.LaFleur inspired some gems in CRATE’s onboarding process, and Sarah herself is a tremendous inspiration when it comes to both dedication and authenticity.
The Immigrant Story
K: As a first-generation immigrant with Bulgarian and Canadian roots,what took you to New York, and how did you lay down roots here?
D: I was born in Sofia, Bulgaria and moved to Canada with my parents at a young age. When I was 14, I visited NYC for the first time and was immediately obsessed. Standing on top of the Empire State Building, I felt a deep sense of belonging and promised myself that I would call it “home” one day.
Fast forward to 2000, when I managed to land a job as an information architect in NYC fresh out of university. I quickly became the digital creative director at the ad agency where I worked, and led the team to build the first ever website for Colgate Total, the second iteration of Gerber Baby, the Century 21 website, and even that big billboard for the Madame Tussauds in Times Square, which was just opening at the time.
NYC is a strange place — it can at once be spellbinding to immigrants yet also deeply lonely for those still trying to find their spot. I spent pretty much my first decade here feeling weird and adrift.
That said, I was used to it. Leaving Bulgaria and switching from one province to another in Canada meant I had left multiple sets of friends behind in my childhood. As an only child, I was used to finding company in books, writing, and art. So the loneliness I felt upon moving to NYC was familiar and less unnerving than it might be for people who uproot their entire lives to starting anew in another country.
I moved here with a deep love for the East Village artists, whose work I had read and listened to for years. I spent the first few years here hoping to run into Eileen Myles or David Bowie. Even though most of them were gone by the time I arrived, their “ghosts” kept me company. I would walk down a street thinking “this artist used to live in that building”, and it was comforting to know that other outliers before me had found their place and created amazing work here.
So was meeting other outliers over time, who became colleagues, friends, and (one of them) my husband. When you have someone to walk the world with, it becomes a far less scary place.
Now, decades later, I still fondly think of the Empire State Building as my building, an old friend that I greet every morning (at least before this quarantine).
Two years ago, I gave a talk on Thinking in Story, which I started by sharing how I had fallen in love with NYC while on top of the Empire State Building. Coincidentally, that talk was on the 41st floor of the building itself. As I walked there that morning, I had to call my dad because I was getting a bit choked up by the full-circle-ness of it all. Right then, a small shadow moved over my head, and I felt a wet blob in my hair. I got pooped on by a pigeon, which took care of any sentimentality and felt very New York.
K: When you moved here for your first job, how did you establish a professional network from ground zero?
D: Back then, “networking” wasn’t something I consciously thought about. Throughout my first jobs, creating things mattered a lot more than networking. I built a reputation based on output, and some of my colleagues at the ad agency became both my earliest local friends and initial network — I never really distinguish between the two.
I learned much later that networking is seen as growing one’s professional connections, so it gets tempting to pile up LinkedIn contacts and business cards. But to me, connections remain non-transactional. Acquaintances, however impressive their titles, can’t impact our path as much as true friends do. People who become close to you because they value what you do or resonate with what you have to say are also most likely to stick around regardless of your status or identity.
At the end of the day, networking should stand for building real connections, helping people, and being engaged, present, and real. You can do so regardless of your country of origin, skin color, accent, and so on.
K: What career challenges and/or opportunities has your immigrant identity presented?
D: As we talked about earlier, being an immigrant means being an outsider, at least initially, which is a double-edged sword. On one hand, we all have insecurities, which can be amplifed by looking and sounding different from everyone else. I have always been self-conscious about my accent, but you learn to get on with it and eventually embrace your differences.
On the other hand, the immigrant experience makes you bolder. While some have fled a past of hardship, many others come here as a gamble, leaving family and loved ones behind. This requires courage and a bit of bull-headedness, taking on odds and unknowns. Having survived this leap of faith, you are likely to find the next challenge a bit less scary, and your courage snowballs from there.
K: Do you carry with you any cultural heritage that makes you proud, an object, tradition, ancient wisdom etc.?
D: Bulgarian Feta cheese and Canadian courtesy are my two major cultural inheritances. I occasionally joke that being out of Bulgarian feta cheese during COVID has been a secondary crisis for me. There’s simply no better cheese, and it reminds me of both my late grandmas, for whom food was a form of love.
As for my Canadian heritage, I still say “sorry” a lot. My family and friends poke gentle fun at me for it, but I’m OK with keeping the polite Canadian in me.
While I’m now an American citizen, I also identify as Canadian and Bulgarian. I didn’t trade one identity for another over the years; I added new ones to the mix. It is like putting feta cheese and maple syrup on New York pizza.
K: What advice would you give to young immigrants who want to break into VC or start their own business in the US?
D: When I got here, I believed that this country — and in particular New York City — was the epicenter of dream-building. I would love to think this can still be true, but the reality is that America (and in many ways the world) is at a crossroads right now. I hope we can choose wisely: from a place of love, not fear.
I think the things most worth doing are ones you would do even after you’ve won the lottery. So I’ll offer the same advice I used to give founders and now hold onto myself: build that which you most need to find. The truer you are to yourself, the more likely it will resonate with others.
Keyi (Author): If you enjoyed this story, check out my other interviews in the Entrepreneurship of Life series (catalog with links at the end) and subscribe (for free) to get new stories delivered to your inbox. You can also find me on Twitter and LinkedIn.