As a practicing Christian, I don’t believe in a big line between “sacred” and “secular” work. I believe that when I’m creating — whether a product or a business or a piece of art or a project with my kids — I feel God’s pleasure, too. To me, this is the simplest and purest form of goodness. But I also recognize that a lot of us don’t get to pursue our passions and gifts, so I really like helping people with that. For example, I got to see firsthand how access to technology can change the course of a person’s life. Because of this, I’ve become passionate about helping kids learn computer science so they can have an opportunity to participate in the new economy, broaden their skills and maybe even start a web business one day. I want to see people thrive — doing what they are made to do — and feeling God’s pleasure along the way. This is why I helped co-found Create A Loop, a nonprofit that teaches kids computer science with a one-for-one model. Every kid who can afford to join the club helps provide a scholarship for kids who might not have access to a computer science education. It’s a beautiful intersection of my vocation and my faith.
I had the pleasure to interview David Karandish. David is the Founder and Chief Executive Officer of Jane.ai, an enterprise artificial intelligence company focused on making all company intelligence accessible in the simplest possible way (think Siri for the workplace). Before founding Jane.ai, David was the CEO of Answers Corporation. David and Chris Sims started the parent company of Answers in 2006 and sold the company to a private equity firm in 2014 for north of $900m. Prior to Answers, David was the CEO of Expo Group, an online resource in the consumer financial services industry. David and Chris Sims’ investment entity Equity.com led the Series A round in Varsity Tutors (an on-demand, real-time learning platform in the ed tech space) and helped incubate Create a Loop (a computer science education non-profit founded to tackle the digital divide) and Prepare.ai (a non-profit founded to provide educational resources and strategic guidance about Artificial Intelligence to individuals, communities, and companies). David is on the Board of Directors of both organizations. While in college, David embarked on several personal projects, including the invention of AIM Talk, a text-to-voice program for AOL’s Instant Messenger. In addition, he was the youngest contestant on NBC’s The Apprentice: Martha Stewart television show. David holds a bachelor’s degree in computer science and a second major in entrepreneurship from Washington University in St. Louis, where he graduated cum laude. He is a member of the Gateway chapter of the Young Presidents’ Organization. David lives in St. Louis with his wife, Erin and four kids. When not working, he enjoys spending time with his family and playing ukulele.
Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?
Back in high school, my dad’s company was throwing away its old computers. He brought one home, gave it to me and I started to learn how to code. I met my best friend in physics class and we started a web design business together. It failed, but…
We leveraged the web skills we picked up to start a custom development company. That failed, too, but…
We leveraged our development business to create an instant messaging text-to-speech bot. That also failed, but…
We leveraged the online marketing of our bot to launch an e-commerce site. Another failure, but…
We leveraged our e-commerce background to create a content publishing company. Now, that failed as well, but…
We leveraged our content publishing to create a comparison shopping engine. And, yes, it failed. But…
We leveraged our shopping site to create a network of websites that ultimately grew to $250M in revenue and exited a few years ago.
We’re now leveraging all of our experience — the successes and the failures — to create a new product, Jane.ai, in a new category: enterprise artificial intelligence.
Can you share the most interesting story that happened to you since you began leading your company?
Maybe this is a silly example, but in our old office, we had a lock box for the spare key. It was the middle of winter and I was the last one out of the office. Just as the door locked behind me, I realized that I had left something inside. I was freezing and didn’t have my key to get back in, so I just asked Jane for the lockbox code. She gave me the answer and I went right in. In that moment I was more excited about lockboxes than Al Gore.
In all seriousness, I used Jane for a simple, trivial information retrieval task. But it just clicked with me that everything in a company should be this easy to access, straightforward and simple. It was then that I knew we were onto something.
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?
My best friend and I started a comparison shopping engine when we were in our early 20s. We were looking for the cheapest possible office space we could find. We ended up in a convent turned office building and we quickly found out that the nuns had given away all of the air conditioning units. So we spent a lot of time installing window units to keep humming along. But any time we turned on the AC in the summer or the heat in the winter, it would knock out the power in the building — and everyone would lose their work. Eventually, we just quit running the heat in the winter until one of our team members asked to go home, shivering in gloves and a parka.
In retrospect, it was a mistake to have an environment that was missing basic elements like workable temperatures (although it makes for a fun story). It’s good to be frugal with your office space, but not to the extent that it hampers your team’s ability to work.
What do you think makes your company stand out? Can you share a story?
I think we’ve discovered a secret. Our secret is that all of your company intelligence lives in three — and only three — places: your apps, your documents and the minds of your team. This secret is the bedrock of our artificial intelligence platform, and I’m excited to be the first company connecting to all three areas in a scalable way.
Are you working on any exciting new projects now? How do you think that will help people?
In the modern office, we waste up to a third of our day just looking for information. We are constantly switching tasks, switching contexts and getting interrupted. Nobody enjoys this. It drives everyone crazy!
We created Jane because we envision a world where all of your company’s intelligence is accessible, everywhere: your apps, your documents and the knowledge of your team. At first, Jane is here to help eliminate waste from our day-to-day lives. But over time, what Jane focuses on is freeing us up to use our talents and gifts to do our best work.
What advice would you give to other CEOs or founders to help their employees to thrive?
Give people clear goals and lots of autonomy.
How do you define “Leadership”?
Leadership is getting different people from different backgrounds and experiences to row the same boat or sing from the same hymnal.
You first need a destination (the race, the choir performance). Then, as a leader, you spend time making sure you have the right people in the right seats. In great teams, people perform very disparate tasks but do so in unison and toward a common objective.
Great leaders don’t just go for the destination — they inspire those around them throughout the journey. This inspiration can come in the form of a loud exuberance or a humble confidence, but the style is less important than the inspiration itself.
Leaders bring out the best in their teams and in doing so stretch what their teams believe about themselves.
Lastly, leaders are able to work with people from different backgrounds. If you can only lead people who look and believe and act as you do, then you are likely limiting yourself and your influence.
What advice would you give to other CEOs about the best way to manage a large team?
Someone once told me that every organization is perfectly designed to get the results it’s getting. I would advise other CEOs to spend a lot of time on organizational design.
Also, do your one-on-ones. Same bat time, same bat channel. You are busy, your team is busy — but it’s so important to communicate directly.
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?
In college, my business partner and I started a lead generation website. One of our mentors Ken Harrington, who at the time was Executive Director of the Skandalaris Center for Entrepreneurship at Washington University in St. Louis, gave us the advice that we were swimming upstream (relative to our market) and needed to change course. It was hard advice at the time because we had a bit of short-term success that was blinding us from the long-term need to pivot. Ken’s advice helped pave the way for us launching our next venture.
How have you used your success to bring goodness to the world?
There’s an old 80’s film called Chariots of Fire. It’s got all of the cheese you’d expect from films of that time (not to mention the classic synth theme). The movie is about the life of Eric Liddell, who competed as a runner in the 1924 Summer Olympics. Eric faces a crisis of faith when his “secular” running is pitted against his “sacred” missionary work. There’s a line in the movie where Eric says, “I believe that God made me for a purpose… — but he also made me fast. And when I run I feel His pleasure.”
I can relate to this. As a practicing Christian, I don’t believe in a big line between “sacred” and “secular” work. I believe that when I’m creating — whether a product or a business or a piece of art or a project with my kids — I feel God’s pleasure, too. To me, this is the simplest and purest form of goodness.
But I also recognize that a lot of us don’t get to pursue our passions and gifts, so I really like helping people with that.
For example, I got to see firsthand how access to technology can change the course of a person’s life. Because of this, I’ve become passionate about helping kids learn computer science so they can have an opportunity to participate in the new economy, broaden their skills and maybe even start a web business one day. I want to see people thrive — doing what they are made to do — and feeling God’s pleasure along the way. This is why I helped co-found Create A Loop, a nonprofit that teaches kids computer science with a one-for-one model. Every kid who can afford to join the club helps provide a scholarship for kids who might not have access to a computer science education. It’s a beautiful intersection of my vocation and my faith.
What are your “5 Things I Wish Someone Told Me Before I Became CEO” and why? 1. Over-communicate. It may seem like a lot to you, but people need extra communication.
We were recently eyeing a new market and potential use case for Jane, and we were trying to figure out the best plan of attack. I was under the impression that we were all on the same page — that our initial outreach would simply be a trial run to find a more permanent sales and marketing strategy in the future. That wasn’t the case.
In the game of “corporate telephone,” a lot can get lost in translation. Because of this lack of communication and miscommunication, there was some conflict between the sales leadership and the marketing leadership. Once we discovered and rooted out the misunderstanding, the conflict quickly dissolved.
2. You’re not alone. Being a CEO can feel like one of the loneliest jobs in the world at times. Get some peeps you can share your story with.
When you’re the CEO, the buck stops at you. The truly gut-wrenching decisions are yours to make and yours alone. For example, it’s relatively painless to take someone who is underperforming, put them on an improvement plan, and terminate them if the plan isn’t met. That’s an easy, straightforward course of action.
But what if you have a team member who generally puts out high quality work, yet for whatever reason, their heart’s not in it anymore? In my experience, toxic attitudes like these just can’t be tolerated in the workplace. They rot and fester, infecting the company as a whole. So, the team member has got to go, right? How do you handle this if the team member in question is a close friend?
It’s in the weighing of choices like these where it feels loneliest as a CEO. That’s why it’s crucial to have people you trust who will hear and support you.
3. Focus on your health. Eat more salads. Work out. It will balance out the junk you eat on the go, traveling, etc.
Being a CEO is stressful. Being in a startup is stressful. Being the CEO of a startup is doubly stressful. Like a lot of people, I carry much of my stress in my body. A while back, I started experiencing lower back pain. The back pain negatively impacted my quality of sleep. The less sleep I had, the more stressed out I got, the more my back hurt — a classic vicious cycle.
I went for a checkup and discovered that I had gained about 25 pounds over the course of a couple years. It was a wake-up call. So, I stopped eating after 8:00 PM and switched up my diet. After 6 months, all the weight had come off. Pretty soon, my back pain went away. Without back pain, I started sleeping better. A new virtuous cycle of health was set in motion.
You’ve got to find strategies to manage stress and take care of your health. If you don’t, the consequences will catch up with you sooner or later.
4. Email is the gateway drug of work. Take an email Sabbath. 24 hours of no email a week and you will be well on your way.
Because of the model of my previous company, we felt it necessary to configure a multitude of automated alerts and reports. Most these alerts and reports were essential, but they resulted in an endless stream of emails. My inbox was bursting at the seams and I would be getting pinged every couple of minutes, making it impossible to focus during work or relax outside of work.
So, I started practicing two things. First, in my new company I moved to inbox zero. Second, I implemented an “email Sabbath.” Once a week, usually from Saturday afternoon to Sunday afternoon, I don’t check my email (or Slack). I give myself 24 hours where I can unplug and be refreshed. It’s a wonderful time to connect with family, read a book, take a nap, get some fresh air — whatever, as long as it’s rejuvenating and will get me centered for the week ahead.
5. If you’re not enjoying what you are doing for long periods of time, then it’s time to make a change.
I was at my previous company for over 10 years. It was my entrepreneurial baby. Over the years, the capital structure had shifted, and the business model was such that external factors could cause intense instability at the drop of a hat. That creative, entrepreneurial spirit that had fueled me began to dwindle. I slowly came to the realization that I was no longer able to create in my role as CEO. I wasn’t able to give my best, and they weren’t able to get the best out of me.
Leaving my former company was very hard — but it was also one of the best decisions I’ve ever made. I’m now at the helm of an incredibly exciting AI startup. I’m back to my entrepreneurial roots. Don’t live in known anguish for fear of the unknown.
You are a person of great influence. If you could inspire 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. :-)
I don’t care what political party you belong to — I would hope that we can all agree that computer science education should be mandatory. The state of Missouri has mandated earth science, but no computer science! I love stalactites and stalagmites, but they’re not going to create employment for a significant percentage of the workforce 20 years from now. It’s crazy that we aren’t teaching our kids to code in a lot of schools today.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
“Running a startup is like eating glass. You just start to like the taste of your own blood.” — Sean Parker
I think so much of a startup is moving from surviving to thriving. In most startups, not enough time is spent assessing how to make this transition.
Some of the biggest 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’d grab lunch with Jeff Bezos. A lot of tech companies have thrived in high-margin markets (Apple, Google, Facebook, Microsoft, etc). Amazon has thrived in multiple low-margin markets and has figured out how to manage hypergrowth along the way.
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