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 Chris Buttenham.
Chris started his first business at the age of 15 and founded Obie when he was 22. He was also the youngest founder accepted into Batch 20 at 500 Startups. Appearing larger and more experienced than you are, has been a skill he honed over the years in order to build and scale a successful business. Chris now is the General Manager of Knowledge at Lessonly by Seismic.
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?
Looking back, it would seem that I accidentally made a career in the historically stodgy, niche category of Knowledge Management. I have always considered myself an entrepreneur, but never got “married” to any particular idea or industry. In between a company I had started in University and “my next thing,” I was working for a company where I fell in love with the problem of knowledge management. I felt the pain of not having access to the answers and tribal knowledge needed to do my job first hand. This led me to start a company in this category called Obie that ultimately was acquired by Lessonly in 2021.
Can you share the most interesting story that happened to you since you began leading your company?
There are too many interesting moments to recount, but one theme that stands out in my mind was fundraising. As a first time CEO, I wasn’t exactly seasoned at asking investors for money. Back in 2017, off the back of a successful “demo day” at 500 Startups (a San Francisco based accelerator) I proceeded to have roughly 100 meetings with investors over the course of the next 6 months. After roughly 100 meetings, I received exactly the same number of “no’s”. Ultimately, we were running out of money and running out of stamina. I recount this time because, while it was amongst the hardest moments of leading the company, it was also the most rewarding from what I learned during that time. In the end, we bootstrapped the finances until 2019 when we turned things around and raised a successful round of financing.
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 probably wasn’t funny at the time, but I mistakenly charged a customer $100,000 on their credit card through our payment processor. While we rectified the issue as soon as we were made aware, I must say I had never seen such an incredible credit limit!
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 am extremely grateful for many people who have helped me along the way — most of whom I’ve spoken about publicly. Though, one person who stands out is my dad. Being an entrepreneur himself, he was always one of a very small list of people who didn’t judge my crazy endeavors. A funny anecdote about my dad was that he used to give me Air Miles so I could fly from Canada to San Francisco when I had meetings because we were so broke and were running out of money early on.
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?
I believe it is important to have people on your team who share different perspectives and experiences. Diversity of thought is an important component of innovation.
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’m not going to pretend that I was a CEO of a Fortune 500 company, because that is very different from being a CEO of a venture-backed startup. That said, in general, I believe a leader is someone who knows how to get out of the way most of the time and knows when to roll up their sleeves and get shit done. CEOs are generally responsible for setting and maintaining the company culture or “pulse” of an organization. They generally ensure that the company has what it needs to stay alive (or thrive) and meet business objectives. In my opinion, a good CEO hires as many people that are smarter than them as possible — assembling a team of people that compliment each other’s strengths and weaknesses.
What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?
I suppose, a common myth is that a CEO should “have it all figured out” or hold all of the magical answers necessary to be successful. Really, CEOs are just the coach on the team who are really effective at leading a group of amazing people in the right direction.
What is the most striking difference between your actual job and how you thought the job would be?
Something I didn’t realize about being CEO before I was one is that most of the job is about people management. Hiring, firing, coaching, motivating, and managing people is basically what it’s all about. It’s a very challenging, but rewarding job.
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?
No. Not everyone is cut out to be an executive. And guess what? That’s okay. I don’t look at it as some prestigious thing, either. To me, being CEO or rather CEO of a venture-backed startup is almost not a choice. Some people just have the leadership or entrepreneurial “gene” so-to-speak. And most people don’t. It’s often a grueling, lonely and terrifying job. It’s about self-awareness and really knowing what your strengths are and where your passion lies. Figure that out, and go all-in on it.
What advice would you give to other business leaders to help create a fantastic work culture? Can you share a story or an example?
The most incredible work culture I have ever witnessed was not my own. I owe this perspective to my friend, Max Yoder, who was the CEO of Lessonly. The culture Max and his team created at Lessonly is utterly palpable to anyone who has the pleasure of crossing paths with these fine people. A culture is really created by looking around at the room of people that make up your organization, discovering what collectively makes you great, and doubling down on those things. What I’ve learned from Max is you really need to “be it” to “see it”. Meaning, if you want to see a positive change in your culture and have that manifested within each new hire that joins your company, you need to embody the qualities and core values that represent your culture. It’s more than just pretty vinyl words on a conference room wall.
How have you used your success to make the world a better place?
I don’t know about making the world a better place, but I certainly try to “pay it forward.” I really enjoy talking to other entrepreneurs and founders/CEOs early in their journey and share with them all the things I did wrong in hopes they make fewer mistakes than I did.
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.)
- It’s not what it’s all cracked up to be — it’s not the glamorous position that it’s purported to be.
- CEO means you raise the money — no matter how you cut it, you’re in charge of ensuring the company’s balance sheet can stay in the black.
- No one is going to teach you anything — it’s lonely at the top, and most duties and skills that a good CEO has are things that are simply learned through trial and error.
- Oh, right. You also must be the #1 sales person in the entire company — if you’re not already a natural-born seller, you better learn quickly. A CEO is constantly selling: the product, the vision, and the culture.
- You can’t surround yourself with people who act and think just like you— the job of CEO is almost entirely about people and while it might intuitively make sense to surround yourself with like-minded people, I found it really important to surround myself with people who compliment my strengths and weaknesses.
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.
I worry a lot about the future of our society and the impact that technology has on us. Technology has and will continue to bring about incredible positive changes within our lives, but if we are not careful, it can also destroy us. I would love to encourage people, especially younger people, to limit the amount of exposure they have to social media and educate themselves on the threat that these things have on our well being in the long run.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
“Life’s a garden. Dig it.” — Joe Dirt.
No, but seriously. Life is what you make of it, so go out there and do something about all the amazing things you say you want to accomplish.
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 would be keen to have lunch with Jim Balsillie, the former co-CEO of Research In Motion (BlackBerry). I’ve always been fascinated by the meteoric rise and fall of the smartphone pioneer and think it would be a really fascinating conversation.
