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Alex Poon of NorthShore.ai: “Build a team of mentors”

Build a team of mentors. For all the things you need to start a startup, there’s too much for a person to know. Mentors sometimes can be a friend or peer as well. It is about the knowledge and experience they have. We saved tens of thousands of dollars and months of time going through […]

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Build a team of mentors. For all the things you need to start a startup, there’s too much for a person to know. Mentors sometimes can be a friend or peer as well. It is about the knowledge and experience they have. We saved tens of thousands of dollars and months of time going through a security audit in my last startup by having the advice of a fellow founder who went through the same process just months ago.


As part of our interview series called “5 Things I Wish Someone Told Me Before I Became A Founder”, I had the pleasure of interviewing Alex Poon.

Alex co-founded 2 VC-backed startups in NYC (Visual Revenue & x.ai) with 1 exit, having raised over 45M dollars of capital. He is currently CEO & co-founder of NorthShore.ai, a knowledge network that brings intelligence to information buried within collaboration tools across organizations. One product he built was used by some of the largest newsrooms around the globe while the other was known to be one of the first commercial applications to apply modern NLP and AI at scale.


Thank you so much for joining us in this interview series! Can you tell us a story about what brought you to this specific career path?

My father was a small business owner all his life. In his 20s, he started a leather import and export company and ran it his whole career. I grew up doing homework after school at his office. We talked often about running a business and the life of an entrepreneur. Starting my own business has always been my dream. I earned my first pocket money by modifying and selling the gear system of these toy track cars that were really popular with Hong Kong kids in the ’80s. Kids competed in public tracks in the malls and they were constantly looking for an edge against their competitors. In 2010, I was a management consultant advising clients on applying big data to their operations. I sensed that big data and machine learning would be a huge trend and decided to start my first startup with a few co-founders. It was a B2B SaaS that provided machine learning-based recommendations to the editorial teams at major online publishers.

Can you tell us a story about the hard times that you faced when you first started your journey?

A year into my first startup, my co-founder and CTO left to pursue a different opportunity. He had a ton of domain knowledge and we were a small team with limited redundancies. It took us months to recruit replacements, learn the system and reorganize the team. At that time, it was the beginning of rising engineering demands in NYC. We had no chance of competing with big tech companies or banks. Instead, we took risks on people as they took risks on us. We hired ambitious engineers without proven track records but who were willing to fight this battle with us. It was one of the hardest things I’ve done.

Where did you get the drive to continue even though things were so hard?

Years ago I took 3 months off to travel through Asia and live in Hawaii for 2 months. I loved every moment of it but it also gave me the evidence that retiring to paradise is not what is going to bring me happiness. Instead, I love working on things that excite me. I look for journeys that are adventurous that I can take on with awesome people. It doesn’t mean that there are no tough times. Though whenever times get rough, I remind myself of the boredom I felt watching the perfect waves hitting the perfect sandy beach for the 80th time.

So, how are things going today? How did grit and resilience lead to your eventual success?

I am onto my 3rd startup now with NorthShore.ai. When I was starting my first startup, we had a very limited amount of capital. My co-founders and I worked 6 and a half days a week out of this windowless room for the first year. It took months to get our first customer and many months before landing a few more. Our competition was well-capitalized and had a beautiful interface. Yet, we kept at it. We iterated on our product and learned from our users. Before long, we were serving some of the largest publications in the world and eventually got acquired.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I was running an engineering team whose main product depended on our ability to process a large amount of data. In order to scale and gain efficiency, we decided to migrate our data processing pipeline from one programming language to another. We tested each component extensively but when we put all the components together and ran real data through them, everything fell apart. My team was all hands on deck. We examined individual components and their associated tests. We traced the data from one to another. Nothing made sense. It took us a day to figure out the issue — one programming language used “seconds” as its default time unit while the other used “milliseconds”. No one caught the math error. Even with the best plans, something always goes wrong. Expect it.

What do you think makes your company stand out? Can you share a story?

A big differentiator between other knowledge management solutions and NorthShore.ai is that instead of expecting our users to migrate their information into our system, we work alongside collaboration tools that are already in place. One of our customers is a customer success team that’s scaling quickly. They needed a way to automate the process of keeping hundreds of external-facing support articles and shortcut macros used by their agents organized and maintained. All this information is kept in Zendesk, their customer success tool of choice. Leveraging NorthShore.ai, they were able to accomplish their business objectives without moving away from Zendesk.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Get the basics right. Eat well, sleep well and exercise. Regularly take time to reflect. Step back to see the forest for the trees. Working hard is inevitable for most successful entrepreneurs. Though if you don’t take care of the above, you risk working extremely hard doing the wrong things. Personally, I haven’t used an alarm clock in years. I wake up naturally every morning and don’t sleep in on weekends. I meditate on weekdays and lift weights 3 times a week. Once in a while, I challenge my kids to a soccer match in the backyard.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

For the past 15 years, a small group of friends from business school and I would get together for dinner every couple of months. Conflicts would come up though we generally kept to our schedule. During Covid, we replaced the dinners with remote hangouts. Over the years, we celebrated our business journeys and new additions to families but also supported each other during difficult times at work and gave each other candid feedback when needed. It was incredible to have friends like that there for me.

How have you used your success to bring goodness to the world?

I believe that when managed properly, technology innovation brings prosperity to the world. Entrepreneurs are the driving force behind these innovations. Whenever possible, I do my best to pay it forward and help the next generation of entrepreneurs. Over the years, I mentored startups in accelerators like ERA and Techstars and I am currently an advisor to a couple of AI-powered startups.

What are your “5 things I wish someone told me before I started leading my company” and why. Please share a story or example for each.

  1. Nobody cares about your startup. I used to worry a lot about how minor changes to our website or product features would impact the world’s view of us. Nothing is more humbling than when your product goes down for hours and no one notices.
  2. Get buy-ins from your co-founders’ significant others. I’ve learned that building a company without the support of your significant other is a recipe for failure for your startup, relationship, or both. Before shaking hands with your would-be co-founders, spend time with their significant others before joining forces. Go overboard to describe the pain and suffering of starting a company to ensure that they know what they are signing up for. Starting a company is a couple/family decision whether you like it or not.
  3. Build a team of mentors. For all the things you need to start a startup, there’s too much for a person to know. Mentors sometimes can be a friend or peer as well. It is about the knowledge and experience they have. We saved tens of thousands of dollars and months of time going through a security audit in my last startup by having the advice of a fellow founder who went through the same process just months ago.
  4. It is ok to wear flip-flops to work. I used to be overly worried about being proper and professional at work. As a founder, you get to choose to build a truly performance-based culture. It doesn’t matter what you wear for shoes. This point might not apply if you or your team are in a customer-facing role.
  5. If you are struggling with whether you should let someone go, the answer is yes and you should have done it 3 months ago. Letting someone go is never easy but for every instance when I faced this difficult situation, I’ve always wished I had done it sooner after the fact.

Can you share a few ideas or stories from your experience about how to successfully ride the emotional highs & lows of being a founder”?

As founders, the highs are high and the lows are low. It is hard not to take the ups and downs of your startups personally. I try to live by Churchill’s quote “Success is never final and failure is never fatal. It’s courage that counts.” Having gone through everything from successful fundraising, acquisition, hiring amazing talents, signing key customers, losing deals, to key people leaving, I developed a damping function against the day-to-day emotional rollercoaster. I learned that every day is a new day and it is likely not as dramatic as I felt yesterday.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

The world faces many massive challenges. I have a particular love for our ocean. Recently, I watched the Netflix documentary Seaspiracy which deeply saddened me. If I am not spending all my time and energy on my current startup, I would start a movement to reform the world’s commercial fishing industry and protect our ocean.

How can our readers further follow your work online?

I post regularly on LinkedIn and also on our company blog.

This was very inspiring. Thank you so much for joining us!

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