Awaken* newsletter

August 1, 2024

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If you have followed the news in any capacity over the last few years, you have undoubtedly heard about LLMs, and the companies building these models. Though the consumer-facing models from companies such as Open AI have captured the hearts and minds of the public, enterprises have different concerns–things such as data privacy, and model reliability.

Enter Cohere, a company developing LLMs to address these issues. Started in 2019, Cohere partners with companies such as McKinsey, Oracle, and all the hyperscalers, and boasts a valuation of $5.5 billion. I sat down with one of the co-founders, Ivan Zhang, to talk about his journey.

TLDR; Key Takeaways

If you only have a few minutes, here are a few golden nuggets from my conversation with Ivan:

  • Sales should be customer-centric. This seems obvious, but have you ever started a sales conversation by talking about your product? Instead, try starting the conversation by asking your customer about their pain points, and then addressing them.
  • Data will be a bottleneck for AI development. Not in the sense that we will run out of internet to train on, but rather that there are types of data which we don’t have a lot of published datasets for. 
  • Your startup doesn’t have to be in the Bay to succeed. Cohere is headquartered in Toronto. This works for them because VCs are more open to remote work after the pandemic and Toronto has a lot of budding technical talent.
  • A key signal to look for when hiring is mastery in any domain. Learning how to master something is fairly transferable. Masters in one domain can likely become masters in another.
  • Being the lone Asian in a leadership room takes some time to adjust to. Getting more reps in has helped Ivan get used to his position.

Tell me about your upbringing, what pushed you to become a hacker?

I was born in Shenzhen, China, and moved to Toronto when I was eight. As a kid, I was always on the computer, even in China, playing the most random arcade games. I don’t want to paint Asians with a broad stroke, but if you’re a male Asian person who has been to high school in the past decade, more likely than not, you’ve played a ton of video games. I did that a lot, and I feel like it built a digital tolerance and stamina for sitting in front of a screen for long hours. Gaming was a big part of why I’m so drawn to building things, working really hard, and doing crazy hours in front of a screen. 

When I got to university, I discovered the hackathon community. Every weekend, we would just meet up at random Ontario universities and sometimes U.S. universities. We would build for the whole weekend. Gaming addiction primed me to get really good at software engineering. I spent my entire first year going to hackathons, building stuff on the side. I had this realization that I could be spending 18 hours playing League of Legends, or I could use the same energy to build stuff, which is also very fun and not as frustrating as a solo queue. It felt like a natural progression.

How has your role within Cohere changed as the company has grown?

When you’re in a startup, your role tends to evolve a lot. That’s been especially true for my time at Cohere. When we started, I was hands-on coding every day, building some of our early systems and pipelines. Eventually, the company grew, and we hired people. Some of our founders had to step up and do some people management.

Eventually, we hired people managers as well, so I have to do less of that. Nowadays, I’m much more settled. I’d say I spend probably 50% of my time still doing technical stuff like machine learning and data processing. For the other 50%, I spend time with customers, either building new relationships, fostering existing ones, or really bringing in business. I think that’s a big part of a founder’s job, like founder-led sales.

How was the transition to doing sales? Did that come naturally to you?

As someone who spent most of my time as the most backend of backend developers, it was definitely uncomfortable at first. When you think about sales, you might think of a business guy with a suit trying to convince someone to give you money for stuff. But when I started doing it more and more, it ended up being about genuinely trying to learn more about your customers, asking them good questions, and figuring out what issues they have. It’s honestly the most important thing you could do. Why are you building anything if you don’t know what your customers want? 

Sales has been super fun because it informs my technical work. I’m starting to see patterns across these conversations, which help inform what we should focus on. Another aspect is that as a founder, when you’re doing sales, you’re meeting executives and other founders as well–so you’re building good professional relationships. For anyone who’s new to it, you should expect some discomfort. But, like anything, you just learn to do it.

Why did you guys decide to focus on enterprise?

The enterprise market is often seen as boring, but actually, most of the world’s efficiency will come from automating a lot of these back-end use cases that don’t necessarily need human potential. A lot of these tasks we’re automating don’t need a well-educated human being sitting at a computer for eight hours a day. We’re much more interested in unlocking that human time for something else. Enterprise is where a lot of this kind of work is done. For example, Oracle is one of our customers, and they’ve deployed our models into their NetSuite features. So, a ton of HR and ERP use cases are now powered by our models. Our mission is scaling intelligence to serve humanity, and what better way to do it than to target the people doing this kind of back-end work at scale? 

We also liked the idea of not having to suck up all of our customers’ data to train these models. In enterprise, we actually ship our models on-prem and we air gap them, so we don’t see any of our customers’ data. In those kinds of scenarios, we have to build our models slightly differently. We have to teach our models to use the enterprise’s internal knowledge bases, use the information returned from these knowledge bases, and then write an answer and cite it. This is all RAG (retrieval augmented generation), which is what we’re focused on because we deploy these models in this air-gapped environment where we can’t continuously suck up people’s usage data. We still have an API and a demo, but the majority of our deployments are on-premise.

What are some areas of AI, whether infrastructure or application, that you think more people should be building in?

I think there will be a bottleneck in terms of training data, but not in the way it’s currently been communicated to the public. Some people paint a picture that we’ll run out of the internet to scrape. I think that’s a naive understanding of how these models work and how to train them. In terms of capturing digital signals—thoughts, demonstrations, audio, video, images, sensory data—there’s going to be a big bottleneck in capturing data from the world that’s not already represented on the internet. The internet does a good job of capturing data and it grows exponentially every year, but there’s information about the world that we experience on a daily basis.

Do you mean information that isn’t easily digitally representable, such as smell?

Yeah, so smell for example–we’d have to build this hypersensitive chemical detector. So if we want autonomous interactive robots in the real world that can smell, there is an information problem we have to solve for the robots, right? They don’t have a nose; we don’t have a great digital nose for them. And I’m sure there’s other stuff.

Why have you decided to keep Cohere headquartered in Toronto instead of the Bay Area?

The three of us co-founders just really like living in Toronto. We grew up here, we have roots here. We also realized that it is actually a pretty great city for A.I. At some point in time, most of the people leading A.I. in the Valley came from Toronto. They came from Jeff Hinton’s lab at the University of Toronto. So there’s a ton of great early talent here. And I think because of how the VC attitude has shifted since the pandemic, investors are investing everywhere. They aren’t restricting investments to the Valley. Remote work is a thing now. And so luckily for us, we’ve been able to raise successfully. We’ve been able to build good models. 

I’ve heard that you don’t pursue brand-name resumes when hiring. What are some signals that you look at instead of pedigree that indicate someone could be a great hire?

I’ve thought about this a lot. I try to think about my own trajectory and places that have rejected me and what signals they didn’t see. What it comes down to is that I look for folks who are extremely skilled at something. Once you’re skilled at something, you can take that anywhere else. Sometimes we want to hire more experienced folks, for sure. But especially in a field like ours where disciplines such as pre-training haven’t been around long enough for anyone to have much experience, you want high-energy, high-autonomy individuals who are excited to learn, experiment, and fail fast.

I try to ask a few questions that probe at stuff related to this. Like, “What’s the coolest thing you’ve worked on?” Then I get to see if they’re going into a lot of detail and are really excited about this random thing. “What’s the hardest you’ve worked on anything?” I want to see if they can go the equivalent of 16 hours a day, seven days a week when they’ve actually gone to bat for something. And then obviously, experience in the field is definitely a big plus, but honestly, the best hires we’ve made have just been high-energy, hardworking, genuinely curious people who are also skilled at software engineering.

How has being Asian impacted your founder’s journey?

I’m not ignorant of it. I definitely know it’s a thing. For example, on my board, I’m the only Asian guy on it. But I’ve been fortunate in that, growing up in Toronto and starting this company in Toronto, it’s not that weird to be an Asian guy in tech. So on the technical front, I don’t see it as a hindrance whatsoever. But it’s definitely been a factor for my own comfort in leadership situations–being the only person that looks like me in certain situations. But honestly, once I got the reps in, being in those situations, it was totally fine. And I think there are a few things that, depending on how you were raised, could affect you in doing business at the leadership level here. But generally, once you get the reps in, it doesn’t even matter.

Is there anything you’d like to shout out?

I’d like to shoutout my wife, she’s a big inspiration for me. Shoutouts to my mom, my dad, my sister. I think my parents taught me what it means to work really hard. I think this is true for many of us immigrants, watching our parents and grandparents work the most menial labor jobs just so we can be fed and go to school. It’s super inspiring. It makes me think: Why am I not working harder? Why am I not thinking about how I can level up and help them retire? My family has been a big inspiration to me. Lastly, shoutouts to Cohere and my co-founders. It’s been super fun, and I’m privileged to be working on this tech. I think it’s genuinely the most interesting thing I could be doing right now.

If you are high-energy, hardworking, and highly curious about AI, please consider applying to work with Ivan at Cohere! You can check out available positions at this link.

Thank you for joining us, Ivan!

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Born in Thailand and raised in South Korea, Thai Lee was shaped by constant cultural shifts from a young age. Although her family practiced Christianity, her early education in a Buddhist primary school introduced her to ideas that would quietly guide her life and leadership.

There, she learned that life is marked by suffering, impermanence, and uncertainty. Rather than seeing these as obstacles, she absorbed them as realities to work with—an outlook that later became central to her approach to business and power.

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Embracing Suffering as a Path to Growth

A core Buddhist teaching Lee internalized early was that suffering is not a failure, but a condition of growth. This belief trained her to stay calm under pressure and to see difficulty as something to be managed, not avoided.

That mental discipline carried her through an intense academic path, including a double major in biology and economics. It also shaped her resilience at Harvard Business School, where she became the first Korean woman to graduate by staying focused on long-term purpose rather than short-term comfort.

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Practicing Utility Over Ego in Business

When Lee purchased a failing IT reseller in 1989 for $1 million and renamed it Software House International, she rejected the idea of growth for growth’s sake. Guided by the Buddhist value of utility, she asked one simple question: does this technology truly help people?

Instead of chasing trends or flashy innovations, she prioritized practical solutions that made work more efficient and reliable. This steady, service-driven approach allowed SHI to earn trust over time, scaling quietly into a $16 billion global company serving major institutions like Boeing and AT&T.

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Right Livelihood as the Measure of Success

As her wealth grew, Lee leaned more deeply into the Buddhist principle of Right Livelihood—earning success through ethical means and responsibility to others. She believes leadership should reduce harm, not amplify ego or excess.

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The Healing Power of the 27-Foot Buddha over New York City by Vietnamese Artist Tuan Andrew Nguyen

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Titled ‘The Light That Shines Through the Universe’, the piece acts as a medium for healing and ancestral memory. More than just a statue, it represents an architectural prayer offered to a city that never stops moving.

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Historical Acupuncture: Healing Global Wounds

Tuan Andrew Nguyen describes his creative process as “historical acupuncture,” a method of using art to target and release the pressure of buried traumas. 

By placing this massive Buddha in one of the most active public spaces in the world, Nguyen addresses the deep-seated wounds of war, displacement, and erased histories. 

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Weapons into Wisdom: The Alchemy of Brass

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A Global Refugee: Resilience in Sandstone

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Those experiences now shape how Anthony runs ZILIO, a fashion tech company building AI-powered sizing solutions for brands and uniform providers. What looks like a startup on the surface is really the result of years spent learning how pressure exposes real problems, and how frustration often points to what needs fixing most.

At ZILIO, Anthony brings that mindset to one of fashion’s most overlooked challenges: the perfect fit. Not just as a sizing issue, but as a confidence issue that affects how people show up, move through their day, and feel in their own skin.

The Lessons That Carried Him Through

Before stepping into the tech world, Anthony spent his years as a professional fighter competing on FoxSports. Growing up Asian in a predominantly white environment, he felt he had to work twice as hard to be seen. This drive eventually led him to the ISKA Victorian Title. However, his toughest fight came outside the ring when he suffered two strokes the same year he founded ZILIO.

Walking away would have been understandable. Instead, Anthony leaned into the discipline he learned as a fighter. As he puts it, “Being a professional fighter taught me one non-negotiable principle: Never quit. No matter what. That philosophy carried me through recovery and continues to guide how I build today.”

Solving the “Booty Short” Problem

The idea for ZILIO was born from personal frustration. As an athlete with a specific build, Anthony found online shopping to be a constant gamble. He still remembers ordering gym shorts that arrived fitting like “booty shorts,” an experience that made him wonder why we can dress video game avatars perfectly but struggle to do the same in real life.

ZILIO solves this by replacing confusing size charts with accurate AI recommendations. The company started with corporate uniforms, where poor fit creates massive operational headaches for brands like Coles and Australian Unity. The impact was immediate. ZILIO has helped partners cut returns by 40% and significantly boosted customer engagement by giving them a fit they can trust.

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Helping People Stop Second-Guessing Their Bodies

For Anthony, this mission is personal. He knows that standard size charts often fail people with diverse backgrounds and body types, including many in the Asian community. His goal is to make sizing “invisible” so that people can focus on their style instead of their anxiety.

“Fashion is deeply emotional, and a bad sizing experience can stop someone from exploring style altogether,” Anthony explains. “ZILIO exists to navigate that complexity and give people clarity and confidence, regardless of body type or background.”

With $500,000 in funding and awards like the B&T 30 Under 30, Anthony is proving that a kid with a big imagination can change a global industry. Whether it’s through his upcoming 3D virtual fitting rooms or his work with major brands like Rebel Sport, he is making sure that the next time you shop online, you’re buying a piece of clothing that actually fits your life.

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From War Survivor to Literary Leader: The Remarkable Rise of Amy M. Le, CEO of Quill Hawk Publishing

Amy M. Le, CEO of Quill Hawk Publishing, has built her life around stories that matter. Not the polished kind that skip the hard parts, but the honest ones shaped by loss, survival, and growth. Her journey reflects how personal history can quietly become a source of strength.

Every stage of Amy’s life pushed her to adapt and redefine what success looked like. She learned early that resilience is not loud or dramatic, but steady and intentional. Over time, those lessons shaped the way she approaches both writing and leadership.

Today, Amy’s work centers on creating space for voices that are often overlooked. Through publishing and community-building, she helps others turn lived experience into stories that resonate far beyond the page.

 

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Born in War, Saved by Courage

Amy M. Le was born during the final months of the Vietnam War, a period defined by intense fear and systemic instability. As an infant, she faced a life-threatening heart condition that put her future in jeopardy before it had truly begun. Because medical resources were scarce in a war zone, her survival was never a guarantee.

Driven by a mother’s fierce love, her family made the harrowing choice to flee Vietnam in search of safety and essential medical care. This escape carried enormous risks, yet it was fueled by an unwavering hope for a life free from conflict. That courageous decision ultimately changed the trajectory of Amy’s life, setting her on a path toward a new world.

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A New Life and a Turning Point

Their journey eventually led them to Seattle, where Amy underwent the life-saving heart surgery she so desperately needed. This successful procedure gave her much more than physical health; it provided a second chance and a profound sense of purpose. With this renewed vitality, she grew up determined to make the most of every opportunity her new home provided.

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Turning Story into a Mission

That personal healing became The Snow Trilogy, a powerful book series telling the true story of her family’s escape from Vietnam and their new life in America. The books resonated deeply with readers who saw their own stories reflected in its pages. What began as personal healing became a collective connection.

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