Kevin Collins of Charli AI

    We Spoke to Kevin Collins of Charli AI

    As a part of our series called ‘Five Things I Wish Someone Told Me Before I Became A CEO’ we had the pleasure of interviewing Kevin Collins, CEO and Founder of Charli.AI.

    Kevin is the CEO and Founder of Charli AI, a unified workspace for your digital content and cloud apps. A serial entrepreneur who has experienced serious highs and lows throughout his career, Kevin is passionate about helping workplace professionals put more life back into their work-life balance.

    Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

    Earlier in my career I worked in various senior management and executive positions across a number of sectors, including telecommunications, professional and financial services, and consulting. From 2008 to 2016, I was the CEO of Bit Stew Systems, where we developed a platform to solve the data-integration challenge in the Industrial Internet of Things. In 2016, General Electric acquired Bit Stew in a US$153 million deal — one of the biggest tech acquisitions to take place in Western Canada in a decade.

    As a result of that acquisition, I lost my executive assistant — and that’s when I understood how much work and stress my EA had shielded me from by keeping me organized and on top of things. Having to take on tasks like scheduling and accounting myself left me feeling exhausted and burnt out. I realized that I, and other working professionals like me, needed an effective way to take those sorts of tasks off of our plates so we could focus on the critical areas of our business — and also free up time for the things that really matter. That’s when I came up with the concept for my latest business venture, Charli AI.

    Can you share the most interesting story that happened to you since you began leading your company?

    One of the more interesting aspects of my role at Charli versus other leadership positions — including as CEO at an industrial-focused company — is the intersection between my private life and business life. Charli is more consumer-focused than any of the projects in my past and this means surfacing more of my private life in the form of experiences and lessons learned. One of those is linking the lessons learned in Overlanding and how they help with startup life. Something will inevitably go wrong at some point when you’re Overlanding. You have to expect it. In fact, it’s kinda the name of the game when you’re off-roading in the backcountry; you need to be prepared for every scenario and you need to think on your feet. I’m sure you can see the parallels here but, what I’ve taken away is that the key to long-term survival is to be prepared for a bumpy ride and have contingency plans for when things don’t go your way.

    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?

    It doesn’t fit into the category of the “funniest mistake”, but it’s certainly a head-scratcher — a “what were you thinking?” moment.

    Not long ago we were trying to figure out the best user experience for everyone using Charli. We didn’t have much to go on but did have some experience with early mobile users and had some ideas. Although these ideas were great in our heads, they didn’t translate well to the reality of what we developed. Our goal was to create an experience that was super simple and easy to use. What we ended up with was a far cry from that and would eventually go on to be called the “Curated Experience”.

    At some point we’ll put this UI in the museum and laugh at ourselves. And we have to learn to laugh at ourselves as we’re innovating and making mistakes from time to time. Even though we’ll make these mistakes, they are fantastic learning opportunities and this “head-scratcher” was no exception. We learned about the real value in the product and how to surface the interactive abilities of Charli in a much better way than we ever had beforehand. We also developed new capabilities that allowed us to experiment with features in real time while not impacting our existing users. We would likely not have the “assisted UI” or “command line” features in the product if it wasn’t for this experience. Moreover, we may not have the “content canvas” in our product or even a content focus if it wasn’t for this fortuitous mistake. Innovation requires experiments, mistakes, and learnings.

    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 about that?

    I’ve been fortunate enough to have a lot of great people in my life who have helped me along the way. These people have been instrumental in my life and business learnings, especially when I’ve made mistakes and have needed some help. One person who really helped me in my early days and passed along some life lessons that I carry to this day is a former boss, now friend. Mike became my new boss while I was at my first real job, only three years into my career. He noticed that I had some bad habits around execution, focus, and self-discipline. We butted heads a lot in those days but he must have recognized some potential, so he persevered. After a few heated exchanges, I did smarten up, and Mike ended up becoming one of the best mentors I’ve had in my career. I give him full credit for helping me develop the ability to stay focused, work effectively with a team, establish achievable goals, and execute on plans. He even taught me the value of diversity in the team and how important that is to making better decisions. I worked with Mike as my boss for another five years before moving on in my career. He is now a good friend and someone that has impacted how I operate to this day.

    As you know, the United States is currently facing a very important self-reckoning about race, diversity, equality and inclusion. This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?

    People from different backgrounds bring a wealth of lived experiences that can give them perspectives that you might never be exposed to otherwise. This is hugely valuable in a business sense, but I would argue that it is equally important on a person-to-person level. Having a diverse team in the executive suite can help cultivate the sort of outside-the-box thinking that business leaders are always striving for.

    On the business level, diversity lends itself well to remaining competitive and being innovative. New ideas come from the seeds that are planted through experiences, discussions, debates and deliberations. Business leaders often talk about innovation and for companies in traditional businesses, getting left behind is not an option. Diversity is an essential ingredient.

    As a business leader, can you please share a few steps we must take to truly create an inclusive, representative, and equitable society? Kindly share a story or example for each.

    A leader has to recognize that their success is not just tied to, but completely dependent upon, the success of the team that surrounds them. This may seem obvious, or even trivial, but in reality I’ve rarely seen it practiced. A leader must focus not on their own success, or even just the success of their team as a whole, but on the success of each individual member of the team. As a leader, you can’t be in it for your own gratification; if you end up shining and the rest of the team doesn’t, that’s not a win.

    Even the most effective team is made up of different personalities, and with that comes the very real potential for conflict. So a leader needs to pay close attention to personal interactions and must establish ground rules for communication. A good example of this is establishing an understanding that everyone’s ideas will be heard, but not all of them will stick. By all means, keep the ideas flowing, but with the understanding that leadership has the deciding vote in which ones get executed. Decisiveness is also a key trait of leadership. We can’t continue to analyze ad infinitum and go through endless what-if scenarios. Make decisions with confidence in the knowledge that if you make a mistake, you and the team will figure it out.

    Diversity of viewpoints is the key to any team’s success. Like-kind thinking doesn’t lead to innovation or give you the tools you need to resolve problems as they arise. There are people that I know will push my buttons or get under my skin from time to time — and those are the ones I want on my team. If the intent is good and the respect is there, these types of colleagues can force you to push beyond your current way of thinking.

    Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

    I can really only speak for myself, but my over two decades’ experience in the technology industry has allowed me to excel in creating capital efficiency, through scaling, fundraising and selling businesses. In fact, in my current role as CEO, I like to describe myself as being the “Cash Extraction Officer”. Being CEO is also not as glamorous as many may think, as CEO I have worn many hats and no job is too small. I sometimes act as the sales engineer and do demos, other times I’m writing for my newsletter, I even get into the code.

    One of the hard lessons that I’ve learned over the past many years is that as CEO, I must have a very acute sense of financial responsibility. Balancing demand with the ability to execute is not an easy task and can be somewhat of a high-wire act. It’s not just about balancing the budget/actuals — managers can do that. It’s about being very strategic and making maneuvers that set up the company for long term success. In the startup world, I’ve always heard the term “cash is king and execution is golden”; as a CEO this takes on a whole new meaning. The executive not only has to innovate, promote innovation and make sure what is needed can get built. This all has to be done with the constraints of the cash runway with a mindful eye to the next fund raising effort or execution to cash-flow positive.

    What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?

    I think people are often drawn to the entrepreneurial world with some warped ideas of what it really means, and what they need to be doing in order to be successful. As a result, people may leave traditional 9-to-5 jobs, lured by the promise that, when you’re the CEO, you get to “be your own boss”. The idea is that when you run the show, you’ll have the flexibility to create a work schedule that gives you the sort of work-life balance that will let you thrive.

    The reality is that it’s all too easy to let that balance tip way too far onto the work side. In the corporate world, we too often celebrate the idea of a “hustle culture” or “culture of busyness”. Given my experience as a workaholic — and a self-described burnout aficionado — I know firsthand that this is seriously dangerous. Our current concepts of productivity and work-life balance are broken, and we need to reassess them.

    Another harsh reality for would-be CEOs is that you might need to re-evaluate what it means to “love what you do”. The truth is that work will always be work. As an entrepreneur, you will be working every day of your life, and it won’t always be enjoyable. It may be fulfilling and rewarding in many ways, but that doesn’t mean it will always be fun.

    What is the most striking difference between your actual job and how you thought the job would be?

    If you are starting a new company or taking an existing one in a new direction, the stress and pressure will be far more than you ever anticipated. It’s one thing to talk about it and a completely different thing to live through it. It will consume every waking moment of every single day — and that’s only a slight exaggeration. You will develop an acute sense of how the company is executing. You’ll also become very clear on how much the company’s finances really matter. (Spoiler alert: they matter a lot.)

    Even though you might have a team to rely on and bat around ideas with, the real ownership and accountability lies with you and you alone. No one else. I’ve had a lot of people ask me if it’s “lonely at the top”, and they have no idea whatsoever about the pressure that mounts and the personal accountability that can consume every minute of the day.

    The fact is, you will soon realize that you are not at the top at all; you’re really at the bottom when decisions have to be made — mostly tough decisions. If everything is going well and the team is executing, you’re likely not too involved. As a CEO you need to get involved in the hard stuff — all the time. You need to think six months, a year, or even two years ahead and figure out how to maneuver around the obstacles down the road, as well as the ones already staring you right in the face.

    There’s no ivory tower, at least not for those leaders who take their roles seriously. I’ve seen so many leaders try to work from an ivory tower that I can certainly see where the impression comes from. The reality of true leadership, though, is very different and you have to sweat the details. You will get your hands dirty. There’s a reason Elon Musk slept at the factory. “Executives” might not get hands-on when the need arises — but leaders will.

    Do you think everyone is cut out to be an executive? In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?

    One of the best traits that any budding executive can bring to the table — especially at a startup — is the ability to move quickly; with confidence and conviction. After all, startups have a short runway, so the ability to make decisions quickly and pivot on the fly means you’ll be more nimble and able to arrive at your destination faster. In a traditionally bureaucratic business environment, decisions move slowly. If you’re coming to the startup world from that sort of background, it can all be a bit of a shock. But if you learn to embrace speed and accept that not every decision will be made with complete information, you’ll come to enjoy the extremely rough ride.

    If you’re afraid to fail or have a tendency to cling to ideas that clearly aren’t working, maybe you’re not cut out for the executive life. You’ve probably heard the phrase “fail fast, break things.” I think a better motto is “fail fast, learn things.” If something’s not working, why stay attached to it? Better to accept that it failed and let it go. Learn from it, and take that lesson with you as you move on to the next idea. Sure, this process means sometimes admitting that you were wrong or tossing away an idea that was precious to you. That can hurt, no question about it. However, the sooner you can put aside your ego, and stay humble and curious, the better off you — and the company — will be in the long run.

    The flip side of this is that the executive must have a strong vision and have very clear goals on what future success looks like. This vision is key to maintaining some level of continuity and morale throughout the twists and turns that a business takes. It’s the difference between having determination to reach a goal and flailing when things fail. Failing is normal; it’s natural; it’s necessary — but learn and adapt quickly to succeed on the vision.

    What advice would you give to other business leaders to help create a fantastic work culture? Can you share a story or an example?

    I think one of the most important leadership skills — one that builds and strengthens the bonds that hold a team together — is the ability to foster resilience. Start by creating an understanding of the larger vision and the role that every individual plays in driving product-led growth. To help your team maintain sight of the goal even when there’s turbulence, pick a north-star metric or develop a powerful vision statement that everyone can buy into. Resilience is about learning to ride the waves, weathering the storm, and maintaining an even keel. If you can help your team do those things, you’ll have a better chance of sailing out the other side.

    But setting the north star and mapping out the mission aren’t enough. Many of us are guilty of assuming that everyone reaches the same conclusions at the same speed. The fact is that it may take some longer than others to internalize an idea, so plan on reinforcing the vision regularly and consistently.

    Frequent, constant communication is necessary to work with a team to help understand, reinforce the message and generate ideas when turbulence does hit. I’ve never been a fan of the annual review process that a lot of corporations go through. Your communication and feedback needs to be continuous and on-demand.

    How have you used your success to make the world a better place?

    Charli’s very existence was sparked by my need to make life better for myself and other working professionals. I want to help people re-examine their definition of productivity and what work-life balance really looks like, without the dramatic shock to the system and period of burnout that I had to endure to get to where I am now. Are you spending your waking hours doing things that really matter, or is your time consumed by “work about work”, at the expense of growing your business or spending time with your family? If it’s the latter, you probably need to step back and take a hard look at what isn’t working for you. In our new hybrid-work paradigm, with so much of our professional lives spilling into our personal lives, it’s never been more important to hit the reset button on how we approach the way we work.

    Fantastic. Here is the primary question of our interview. What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

    1. Don’t define yourself by how much work you can get done in a day. We live in a productivity-obsessed world that encourages us to define our worth by the volume of work we’re able to accomplish in any given day. I have fallen into that trap myself, but I now believe that the true value we get out of life is in direct proportion to how well we’re able to prioritize the aspects of our lives that we enjoy most, whether they’re professional or personal.

    2. You can’t multitask, so stop trying. Your PC can’t even multitask; it’s just really good at switching back and forth between different tasks really quickly. You’re not a computer, and the sooner you realize that and stop trying to act like one, the better off you’ll be. I wish someone had told me this before I burnt myself out trying to do everything all at once, but if I hadn’t gone through that experience, Charli wouldn’t exist. Sometimes you’ve got to take the bad to get the good.

    3. Customers want a steering wheel, not a black box. When we were first designing Charli, we envisioned it as a “fire-and-forget” product. We were asking people to hand their data over and let the AI worry about where to put it. It was a nice idea, but we soon realized that this sort black-box approach doesn’t sit well with a lot of people. It turns out that they are often afraid to give control of their content to a machine, and understandably so. We have since figured out that if you want your customers to trust you with their data, the smartest thing you can do is give them a steering wheel and put them in the driver’s seat. In Charli’s case, that meant telling our AI that it couldn’t do anything with a user’s content without first storing it in Google Drive. That gives the user ultimate control over their stuff, since they always know where it is — and they can take control whenever they want.

    4. Your first idea isn’t always your best idea. Neither is the second one, or even the third. Here’s my definition of a successful startup: it’s one that develops an innovative product or service, brings it to market, and has customers adopt it because it’s solving a real problem in a new way. This is easier said than done, because it often means you’re forging your own path without a roadmap — or even a road. It can mean wrestling with different theories and testing ideas until you find the one that clicks. The right idea will almost never be your first idea, or even your second, third, or ninth. Everyone will want to give you conflicting feedback, and that feedback will be all over the map. Your challenge lies in balancing that feedback to make changes, to adapt, and to continue moving forward, always onto the next idea.

    5. Even the worst disruptions can have their upsides. The truth is that the COVID-19 pandemic has been a terrible thing in just about every way imaginable, from a public-health point of view and from a business perspective. In spite of all that, it does illustrate something that every business leader should understand right from the start: No matter how dire a situation may seem, something positive can almost always come from it. I learned this firsthand when my own personal work-life imbalance led me to the idea for Charli.

    In the case of COVID, consider how readily the world embraced and adopted remote work, and how widespread the hybrid model will likely be long after the pandemic is over. That alone could have some lasting positive impacts as it continues to shape conversations about productivity, and what a healthy work-life balance could look like as we move into the next normal.

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

    As you have probably gathered by now, I am already engaged in something of a crusade against multitasking. It’s bad for us as individuals, and I think it can be disastrous for society as a whole. The fact is, excessive multitasking can be a productivity killer, and it can be a one-way ticket to Burnout City. (Take it from someone who used to live there.) If you really want to excel and create high-quality work, you need to eliminate distractions and disruptions, and focus. In other words, you need to single-task.

    Part of the problem is information overload — busy professionals are bogged down in an endless stream of digital “stuff”, and throwing more and more shiny new productivity apps at the issue isn’t helping. What we need is a solution that organizes, tracks and stays on top of the information that’s needed, working seamlessly throughout the day to support single-tasking.

    Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

    “If you always do what you’ve always done, you’ll always get what you’ve always got.”

    We are very 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 with, and why? He or she might just see this if we tag them.

    I have a newfound respect for the trials, tribulations, and toils of starting and running a company. Certainly not at the level of some of the folks I’ve been fascinated about. One person that comes to mind is Bill Gates because of all the twists, turns, and challenges that face us throughout our career. It would be very interesting to understand some of the behind-the-scenes activities and maneuvers that Bill Gates had to undertake as a founder and CEO. Navigating the waters must have had significant stress points and even the personal interactions and personalities that he had to deal with over the decades would be intriguing to hear about.