Alex Poon of NorthShore.ai: “Love your customers”

Love your customers. Particularly in B2B software, when you think beyond your product offerings and focus on solving your customers’ issues, you gain supporters. These supporters become your best marketing and sales engine. Startups have such a glamorous reputation. Companies like Facebook, Instagram, Youtube, Uber, and Airbnb once started as scrappy startups with huge dreams and […]

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Love your customers. Particularly in B2B software, when you think beyond your product offerings and focus on solving your customers’ issues, you gain supporters. These supporters become your best marketing and sales engine.


Startups have such a glamorous reputation. Companies like Facebook, Instagram, Youtube, Uber, and Airbnb once started as scrappy startups with huge dreams and huge obstacles.

Yet we of course know that most startups don’t end up as success stories. What does a founder or a founding team need to know to create a highly successful startup?

In this series, called “Five Things You Need To Create A Highly Successful Startup” we are talking to experienced and successful founders and business leaders who can share stories from their experience about what it takes to create a highly successful startup.

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! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

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. My family moved to the US and I studied electrical engineering at Boston University. I entered school with the plan of obtaining a Ph.D. in EE. My part-time job at the time was as a research assistant in a graduate lab where they grew new semiconductor materials atom by atom. As I spent time with Ph.Ds in the lab, I quickly realized that slaving for years in a research lab and pursuing scientific breakthroughs was not what excited me. So I gathered all the extra credits, graduated from my undergraduate program in 3 years, and found a job writing software for military drones instead. After years of working as a developer and management consultant and 2 graduate degrees later, I started my first company in 2010.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

We were working on an adjacent concept to let teams manage decision-making in a more structured way. As we showed our prototype to early users, it was clear to us that the concept was too narrowed and wouldn’t significantly impact the lives of our users. Yet, these conversations unearthed a much larger pain point — key knowledge our users needed to do their job was stuck inside of various collaboration tools, poorly organized, and sometimes, hard to know that it existed in the first place. Employees ended up taking action on outdated information. Experts were burdened with answering repeated questions. Onboarding and offboarding were unnecessarily painful because the team had limited visibility into what knowledge needed to be transferred and who owned which piece. We built NorthShore.ai to address these issues.

Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?

My father was a small business owner all his life before he retired. 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. He loves telling me stories about his leather deals and that all of his biggest transactions were done with a handshake and no formal contract in place. To him, trust and relationship trump everything in his line of work. I also learned to lead by example and the importance of grit to an entrepreneur by watching him day in and day out.

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.

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.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

  1. Willingness to make unpopular decisions. Part of my first company’s product offering was the ability to process a massive amount of data for some of the largest online media properties. As we scaled, our homegrown data processing pipeline started to buckle under pressure and failed periodically. The default path was to maintain course and improve the homegrown solution incrementally. Instead, I made the unpopular decision to migrate our pipeline to a battle-tested open-source framework. It was a huge undertaking that temporarily doubled our infrastructure cost, sucked up engineering resources for months, and forced our team to learn a new programming language. Though the end result was a stable system that handled 6x our original traffic when we were acquired later.
  2. Discipline. I believe that the most effective way to impact lasting personal change is through habits. I build habits for all important things around me from meditating, workouts, team metrics reviews, to feedback sessions with my reports. I run my life on my calendars.
  3. Calm under pressure. I am often the person to lead during crisis situations. In our early days of x.ai, one day our team noticed that our application was failing at random times. Upon further analysis, we realized that our company no longer owned the domain x.ai and our system was slowly failing due to missing permissions. I led our backend and infrastructure teams to methodologically run through each potential cause from getting hacked to configuration errors. 8 hours later I finally found the root cause after getting off the phone with our representative at the Anguilla domain registrar (the owner of all .ai domains). It turned out, someone fat-fingered the entries into the spreadsheet that held all domain ownership records in Anguilla. Yes, you read it right. In 2015, the fate of thousands of startups and websites was dependent on a spreadsheet that was being updated by hand.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

Fake it ‘til you make it. As leaders, it is important to project confidence in our vision and decisions. Though, when we put up this confident front in all situations and at all costs, people see through it. We end up losing credibility. One time, we lost a key employee. I put up a brave face and tried telling the team that it was no big deal and we didn’t need the person anyway. It was obvious that no one bought it and I just looked either deceitful or incompetent for saying it. I’ve learned to be transparent to my team both in good and bad times. There have been some really uncomfortable situations but the trust we built along the way was worth it.

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, our 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 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? What strategies or techniques did you use to help overcome those challenges?

Celebrate small wins. The startup journey is long and sometimes people only focus on what shows up in the press: funding rounds and exits. Instead, we do our best to treasure all the little moments of success. Get excited about your 8th customers, the most number of users to date, hiring a junior analyst with multiple offers, your first customer referral, etc.

The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. 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 it was yesterday.

Let’s imagine that a young founder comes to you and asks your advice about whether venture capital or bootstrapping is best for them? What would you advise them? Can you kindly share a few things a founder should look at to determine if fundraising or bootstrapping is the right choice?

Venture capital is one of the most expensive ways to fund your business. It also comes with sky-high expectations. There’s a small percentage of businesses that make sense to take VC money. If you share the same expectation and ambition and have a product/business that can back it up, consider venture capital. On the other hand, many amazing businesses have been built bootstrapped and with revenue. It is basic math. 100% of a 5M dollars business is more valuable than 1% of a 100M dollars business.

Ok super. Here is the main question of our interview. Many startups are not successful, and some are very successful. From your experience or perspective, what are the main factors that distinguish successful startups from unsuccessful ones? What are your “Five Things You Need To Create A Highly Successful Startup”? If you can, please share a story or an example for each.

  1. Don’t give up. It was so tough 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, learned from our users, and hired ambitious people willing to fight this battle with us. Before long, we were serving some of the largest publications in the world and ended up getting acquired.
  2. Love your customers. Particularly in B2B software, when you think beyond your product offerings and focus on solving your customers’ issues, you gain supporters. These supporters become your best marketing and sales engine.
  3. Be data-informed. Startups are often run and joined by people with strong personalities. When you push everyone to bring data and evidence to back up their points of view, you give the best answer a better chance of winning out instead of who has the loudest voice.
  4. Your early team defines your culture. In my last startup, we promoted many capable young people from within. As we grew, they became the extension of the founders in how the team should act or make decisions. They had the credibility to answer the question — what would the founders do in this situation?
  5. Trust trumps everything. One of my biggest mistakes was hiring a leader who dazzled me with his management philosophy only to see the whole team revolt because of his inability to build trust with them. Every initiative was viewed as a trick or scheme, rendering him completely ineffective.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

I have seen mistakes from both sides of the spectrum. I’ve seen business founders who don’t pay nearly enough attention to the product and engineering side of the business. Focusing only on deals, they end up overpromising and under-delivering to customer expectations because they simply didn’t understand their own product and its limitations. On the other hand, I’ve seen tech founders who believed that if they built it, the customers would come. Only much later to find out the hard truth that people don’t care about your product. Distribution needs to be thought through. Starting companies is a multidisciplinary game. Founders and their founding teams need to bring together the complete view on how their products are designed, built, marketed, and sold.

Startup founders often work extremely long hours and it’s easy to burn the candle at both ends. What would you recommend to founders about how to best take care of their physical and mental wellness when starting a company?

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.

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.

We are blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them.

Reed Hastings has been my idol for a long time. It is incredible to see the clarity of strategy and execution of Netflix over the years. I also appreciate the thoughtfulness in culture he has since the very beginning of the company. I particularly love the story about how Reed excluded his DVDs executives and brought in only the streaming executives to his management meetings although DVDs were generating all of Netflix’s revenue at the time. Through actions, he clearly demonstrated to the team the vision and strategy of the company. It took guts!

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 the time you spent with this. We wish you continued success and good health!

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