There is no learning equal to headlong immersion.
From the first introductions, we knew this conversation would be exceptional. Caen’s passion and energy were palpable and of a fingerprint without match. He had a natural ability to decompose demanding subjects into meaningful and breathtaking stories. We had never experienced this before and left the conversation feeling like we had taken a sip from the fountain of wisdom.
Caen's story wouldn't fit in a single book. Brazilian-American, he grew up in the United States in modest circumstances, surrounded by a loving and supportive family. He demonstrated early on an unrivalled curiosity and persistence, which led him to earn a full-ride to Dartmouth College after finishing as Valedictorian of his private high school. During his time as a student, he studied Political Science and Computer Science while falling in love with eastern philosophy as well as medicine. Following this passion, he studied in China where he developed a translator-level Mandarin in 12 months.
Caen is a born entrepreneur and has helped build several companies from scratch, including Lime, where he was part of the founding team, growing the company from 5 to 700 people, 100 global operating markets, and a valuation of $2.4B. He is currently co-founder and Partner at Ozone X, a US and Europe-focused VC firm backing under-represented founders (women, people of color, LatinX, immigrants, etc.). Since Lime, he has also co-founded or co-led more than 4 businesses in the sustainability and healthcare sectors. Wow!
But that is only one part of the story.
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This interview has been edited and condensed for clarity.
How would you describe yourself?
I am an introverted creative and autodidact who taught himself how to be an extroverted entrepreneur and practical manifester. Most people don’t believe me, but whenever I am not in execution mode, I am quiet, pensive and fully connected with nature and art. I try hard to embrace the holism within which we all coexist, and not the humanism rampant in our society today.
How did your upbringing shape you?
I am a by-product of an immigrant mentality tied with a revolutionary heartbeat. My mum is Brasilian, from a town of 100s of people in the middle of the country’s farming “interior”. During her last year of high school, she moved to the US with very little and worked extremely hard cleaning houses and working in factories. She gave me my shoulders, my back and all the staying power I call on most weeks. And on my best days my heart touches her everyday. My dad is a self-taught intellectual, revolutionary, socialist, and unionist. He taught me the power of knowledge, dissent and responsibility.
I was born in Dorchester, close to Boston, then regarded as one of the poorest districts in the US. My parents worked around the clock to make ends meet, and sent us back to Brazil during summers to keep costs low while they worked. Despite that, they were very thankful for the intrinsically more important things in life. They taught me the importance of diligence, persistence and staying true to what you believe.
What were your passions as a kid?
My parents pushed me hard to be exceptional in school and 'extracurriculars'. In many ways, it is the stereotypical immigrant story: I needed to stand out to have my shot – and I was "not throwing away my shot" to quote the modern master, Lin-Manuel Miranda (yes, I often daydream that my middle name - Miranda - can be traced back to some relation of his).
As an example, I was really into fantasy baseball, and I remember particularly well the day I won my league amongst a number of seasoned players more than twice my age. My dad told me he had not raised his son to be the best in a fantasy world.
He was right; the metaphor struck and stuck. This is one of many small but significant moments that defined my character, formed my values, and ultimately focused me forward. It always came back to doing things that have a grander design for positive system impact, back to taking on pressing societal issues here and now.
How did it all change in college?
I thought I was going to work within the world of political science and government. I believed the highest level of change was in these spheres - confusing government for governance. I wanted to be part of the change, and not just influence but enact crucial decisions for society, so I pursued foreign service. I learned Mandarin and Arabic and was fortunate to aid in the Beijing Olympics as a translator. It all came back to interconnection and learning as much as possible between the cultural and disciplinary lines. These experiences provided me with a deep understanding and real-world simulations of how things work, instead of oversimplified textbook explanations. I started to see the world in systems.
What does it mean to see the world in systems?
In short, everything is an input and output of a system, including the system - which is why I prescribe to a holonic worldview, where systems within systems work together to create larger systems such as our health, culture, startups, and more. A holon is something that is simultaneously a whole in and of itself, as well as a part of a larger whole, and was a term coined by Arthur Koestler in The Ghost in the Machine. Apply this to how to influence any system and you can see why I consider being an entrepreneur as being a "systems builder" to quote Marc Ventresca, Professor at Oxford SaĂŻd Business School.
Now the question is, how do I impact the current system to enable a mutually symbiotic and sustainable improvement to the system… while considering the 1,000s of variables at play? Not easy. This is why I work backwards and focus on identifying “emergent properties” and nurturing appropriate conditions for them to organically manifest.
To make it more palatable, an example is the ripening of fruits, as some strawberries will never sweeten and achieve their fantasia floral finish. Governing elements balanced in harmony across time – such as water, fertility of the soil, sun exposure, ambient temperature, etc – all influence the end taste of the strawberry and are all part of the system of nurturing and ripening any fruit plant to harvest. The incredible reality is that the desired taste, what you want to maximize, is the very last thing to emerge - hence an "emergent property".
So, working backward, the key to being a system builder is finding points of impact where you can evolve a system to reach its ideal frequency and quality of symbiotic emergent properties. These are what I consider the leverage points. Leverage points are places in a system where, as systems theorist, Donella Meadows said, "a small shift in one thing can produce big changes in everything". Think of leverage points as acupuncture points — places where a finely-tuned, strategic intervention is capable of creating lasting change, creating positive ripple effects that spread far and wide.
Bringing this in a startup context, it is vital to understand the industry you’re working in from a systemic perspective; it is the basis for any lasting, disruptive change. You must understand the currents moving underneath what you can see.
Disruption is just another way to say alter the system and ideally in a way that evolves to improve harmony across all holons.
You lived in China, how was your experience there?
It was one of the most challenging and transformative experiences of my life. I was in a completely foreign environment, studying at a traditional Chinese University. I took classes entirely in Chinese that were supposed to be for Juniors in the United States. While I was a top student from the start - I take on all I do with full heart - I noticed that though my written traditional and simplified Chinese was fast improving, my conversational Mandarin remained elementary at best.
I noticed another international student improving his oral language skills much more quickly by actively socializing and joining group activities and realized that I was playing it safe by staying in my books. I forced myself through the pain and embarrassment of sounding like an infant and started to spend more time with my colleagues outside of class. As my dorm-mates were Chinese and we weren’t allowed to speak English, need bred evolution. It was a crazy but meaningful time!
There is no learning equal to headlong immersion.
Sustainability is a topic you have at heart. What’s your definition?
My definition. No pressure. Well, off the top of my head: 'Sustainability is nurturing cooperative systems to enable shared longevity and health'. It is important to repeat that we are never operating in an individual system. Instead, we exist in a system within a series of other systems co-existing in some form of time and space. This is why I love the study of system dynamics.
You also spent a lot of time studying nutrition. Where does that come from?
While always athletic, I was almost diabetic finishing high school, with my weight being around 240 pounds (approaching 110 kg) as a senior in high school. However, I lost 65 pounds (30 kg) the summer before college by bringing awareness and focused change to my health: largely exercise, diet, and sleep. After seeing I could indeed change from a “fat kid”, I realized it all came back to my poor nutritional education. After first losing the weight, I then wanted to keep it off, and so got into optimizing health through traditional medicines and later biohacking. It was one of the reasons I studied in China – to understand the holonic arts of Traditional Chinese Medicine, which alongside Ayurveda is one of mankind’s most ancient medical arts. They are both focused on preventative rather than curative care and are searching for sustainable ways to maintain peak health. Look at it another way: it’s another beautiful system my curiosity loves to get lost in ;)
How did you find your way into entrepreneurship?
I was very fortunate to have studied at Dartmouth, the experience of which included exposure to Silicon Valley. I could have pursued more traditional routes, taking a high-paying and prestigious banking job or a more distinguished position in the foreign service in pursuit of a Diplomatic career. However, early during my time at university, I realized that this would never fulfill me. Honestly, I knew even then that I was a "create my own blaze" type of person. I didn't want to win a game governed by static rules created by other people without full system dynamics considered. I wanted to succeed in my own way. Entrepreneurship was my way to accelerate learning and where my merit, abilities and clarity of vision were the only limits to the scale of my impact.
You were part of the founding team of Lime. How did you end up there?
An investor from one of my previous companies was monitoring the mobility revolution in China. After seeing the explosive growth of shared-bike solutions there, he started to build a team to launch a similar product in the United States and asked me if I wanted to join the cause.
Many in the United States thought us crazy: shared bikes and other multi-modal last vehicles? Might work in China but not here we’d hear. As someone who had lived, grown-up, and traveled around the world, I was fortunate to see things differently and agreed with my investor and then new Chairman on the potential of what we could build, but we had to localize it to a Western audience. Localization happens in many ways. A funny story we share is that the initial idea was to call it Lemon Bikes. However, if you know a thing or two about colloquial English (or economics) - you know that Lemons is a notation for something considered a piece of garbage vehicle. So we fell on Lime, for all the reasons it still rings true today. I had quite a journey at Lime and we scaled the company from just a couple of people to a truly global organization with hundreds of people and generating hundreds of millions of dollars a year.
Why did you leave Lime?
Every company has its lifecycle. I’m an early-stage person who most enjoys building the engine and establishing the vision and hopefully values of a company. I am not the person who reengineers it to make it 2% more efficient once the general physics have been established and the value is already being created at scale. I helped get the Lime engine running, but once you have a 700-person organization, it is suddenly a different game. I was no longer able to build at the system level anymore, that is the reason I moved on.
I’ve always enjoyed the earliest stages of company building the most.
You’re also on the VC side of the table. How’s that been?
I am an operator, and the reality is that building a fund is similar to starting a company. We are currently defining a new category in the venture capital world with our fund, OzoneX. Instead of having an in-house investment team like most firms, we have a network of thousands of vetted experts within our core focus industries (sustainability, health, education, and employment) who are evaluating the opportunities with us through a proprietary diligence process. The process is engineered to eliminate bias and increase the likelihood of predicting a company’s success.
As a venture capital investor, you see hundreds of companies coming to life and so start recognizing patterns. Being both an investor and operator, I can increasingly speak from both sides of the table and understand their push and pull perspectives. Having this twofold perspective provides me with an upper hand when helping companies as well as driving my own personal missions forward.
Pattern recognition is crucial. The more you see the system within, the better you will understand how things work - the governing dynamics. I believed the quickest way to learn was to build from both sides of the table.
Building companies seems to be in your lifeblood. Will you ever settle?
Settling down would be hard for me (laughs). My main strength and passion are in solving problems and manifesting an evolved vision from the ground up. I am not saying I won’t settle for years into the right opportunity, but I believe that the most impact is created when you go from zero to one and those are done in “tours of duty” over a trajectory that becomes a career, to paraphrase Reid Hoffman.
My mission is to help as many purpose-driven founders working on bold missions to go from crawling to running. That’s a legacy of which I’d be proud.
What was the time you felt the most vulnerable?
Being a founder feels like walking in the dark, and you’re always vulnerable… or you’re doing it wrong (laughs). It isn't any easier for me to cope with uncertainty than the next person. I just try to reframe any pain as surmountable and the path to new lessons and improvement. As a founder, you are the one who takes the extra calls, stays late in the office, and is responsible for the ups and downs in morale. Going through those difficult times while showing confidence to the rest of the team is not easy. Not to forget that the early stages of building a company are extremely punishing, any mistake can be fatal. Be ready to question everything all the time. Oh, and also, have strong self-belief. Do as I say, not as I do here! Hah.
What’s your take on depression?
I was diagnosed with bipolar disorder at age 17. I know what depression feels like. Like everyone, I also have moments when getting out of bed is the last thing I want to do. As a founder, you are responsible for lives, and people depend on you. And what’s worse: people will tell you it’s self-created. Most of your family and friends won’t understand why you “do it to yourself”. Depression is a real thing in the industry. To the people who are struggling with depression, please know you are not alone and you are not your thoughts. That always helps me. Depression is a mental state from which you can move in and out, so don't let your current emotion define you. Keep fighting!
Inspiring story Caen, thank you very much.
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