When I was a little Karl, I knew I wanted to be a professional football player. In fact, before I had even turned four years old, I declared to my parents, “I want to play football at Stanford!” (Stanford is my dad’s alma mater.)
The great irony of that dream is I never actually played organized football. Sure, I played two-hand touch and whatnot. But by the time I was actually old enough to play real football, I wanted absolutely nothing to do with it.
History repeats itself, though. My son just turned nine, and wouldn’t you know it? He also wants to be a football player. We’ll have to see how it plays out, but I digress.
Aside from my aspirations of football glory, I was also interested in technology and computers from a young age. I was definitely that kid in your neighborhood who was always taking stuff apart when it was broken, and trying to figure out how I could fix it and put it back together.
Soon after, I was helping out on the tech side with the various businesses my parents and my sister were involved in. And friends of the family were also seeking me out to help fix their computers and VCRs.
But this isn’t the story of how I grew to love IT and chose it as a career. In fact, it was this time period that taught me I didn’t want to go into IT when I grew up. I did, however, love playing and fiddling with technology.
I also had a mother who had studied computer programming in college – back when programming was accomplished by punching holes in cards. She tried to explain it to me a number of times and it never quite stuck. What did stick was this notion that I could develop programs and software of my own someday.
By the time I hit middle school, I (like many others across the country) used America Online to explore that initial era of the internet. Again, I was struck by this expanding horizon of what was possible for me to explore as I grew older.
I followed in my dad’s footsteps and went to Stanford.
I think there was an assumption, however, that I would study computer science, given my history. I definitely wanted to learn more about it, but it also wasn’t my primary focus. For instance, in high school, I also had discovered my aptitude and passion for advanced math courses like calculus.
Being in possession of a wide range of interests – programming, technology, math, and even a little business – empowered me to not box myself in and be open to different opportunities as I went into my college years. Sure, I had friends around me who were entering pre-med programs, and that was the absolute right move for them. (It’s also the path my dad walked, who later went on to become a doctor.)
But for me, that was such a huge decision to be making as a freshman who was still learning about myself and the world around me.
I opted to commit myself to an engineering degree, and my engineering degree was as interdisciplinary as I could get – it mixed in a lot of math and science, as well as advanced classes in completely different fields – and I loved that.
For those who were enamored with technology and had dreams of breaking into the industry, graduating from college in 2003 was a strange, somewhat depressing experience.
At the start of my college years, everyone who had a brilliant idea went online to buy a domain and make millions. For a time, everything the “.com” industry touched turned to gold. The windfall was short-lived, though. A few years later, the bottom fell out of that entire industry, and everywhere you turned, someone was going out of business.
To top it all off, I had actually turned down Google when they tried to recruit me in 2001. One small reflexive of me regrets that. But truthfully, I don’t really regret saying no. What I regret was not taking it seriously.
So, by the time I was graduating, I had two choices in front of me – I could go into consulting or investment banking.
I chose the latter, but I did so at a startup that was only about a year old. The partners were all former founders and CEOs who had become disenchanted with the status quo of the investment banking industry. That was something I found incredibly interesting because I had interviewed at some of those more established firms and it was such a drag.
So, I said yes to this very different opportunity, this reimagined approach to investment banking, and I’m very glad I did.
This provided me with the next chapter in my business education. Every day I was learning something new and saying to myself, “Wow, this is what companies out there are doing and this is what they can look like?”
I also spent a lot of time learning how new companies across a wide range of niches and industries fit into their ecosystems, established their differentiators, got acquired, and so on.
Most of all, it was a crash course in learning what’s out there – something that I still really love. What are companies doing? And as I dug into specific organizations, what is this company about? What space are they in? What are they trying to do? How might they make money if that's not obvious?
I discovered those were the exact types of questions and problems I loved digging into.
But at some point, I realized that while I loved the partners who founded the company, I didn’t want to be one of them. They were all incredible with sales and making pitches, whereas I was enjoying the “grunt work” of getting my hands dirty once our companies were signed on to work with us.
I took a small break and went to business school.
I knew Amit Kapur – with whom I later co-founded WhoCo – from my time at Stanford, and we were fast friends. So, when he let me know he was leaving MySpace to start his own company called Gravity (which was tackling the exciting challenge of personalized experiences online), I was on board.
It was an exciting time being on the ground floor of a startup, truly building something different, and solving new problems that were evolving in real-time as technology continued to rapidly advance.
Still, it was messy. A lot of people say they know what they’re getting into with founding a startup, but the reality can be somewhat jarring for people.
If being one of the leaders of a startup is right for you the way it was for me, that kind of “mess” of wearing multiple hats and “building the boat while you’re sailing it” needs to be something you think of as fun and interesting. You have to have that appetite, that curiosity, that insatiable urge to build something bigger.
Then we were acquired by AOL, and AOL was acquired by Verizon. The first year after we were acquired by AOL, the experience was still very grounded in what I was used to with the startup culture of Gravity. But after that, things changed, as is the nature of being acquired. I started mostly working with people I didn’t know, my goals shifted away from things that truly interested me, and the culture had matured in a different direction.
A new chapter was about to begin, however. One I’m now writing here at WhoCo.
On the one hand, I’ve always treasured my ability to be open to what’s possible throughout my education and career, being mindful not to artificially close a door based on invalidated assumptions or gut feelings.
On the other hand, I still maintained control over my destiny by asking myself at every decision point, “What am I expecting or hoping to learn here? What will I get out of this?” Even though I would often be trying very new things in the early stages of my career, challenging myself to answer those questions kept me on a path of growth and true discovery of what I really wanted to be doing.
I cannot stress enough how important networking is. But not in the traditional sense that I see others suggest of reaching out blindly to people you’ve never spoken to, for conversations that don’t really have a true goal or outcome. Those types of networking strategies often turn out to be demoralizing dead-ends.
When I talk to younger folks who are struggling, I encourage them to look at their networks closest to home; those are the networking opportunities most overlooked. Who do your parents or siblings know? Are there family friends whom you admire or look up to? Have you had any bosses or peers who are just crushing it?
Talk to as many people as you know in your circle, and continue that as you progress throughout your career journey.
I know this sounds cheesy, but you have to be excited about what you’re doing every day. That doesn’t mean you won’t get stressed or that won’t ever feel like work, of course. And yes, there will be moments where you make bad decisions.
But how you encourage yourself is going to be rooted in the natural energy and passion you have for the work you’re doing. This is something I learned the hard way. I certainly made mistakes, especially with internships where I was not excited in any way about what I was doing. Because of that, it was virtually impossible for me to get anything out of what I’m doing.
If you find yourself in a situation where you’re not excited about anything you’re doing, that’s a sign that you may want to consider looking toward a different opportunity.
You are choosing an interesting and wildly challenging path; one that I’m still navigating myself in this new chapter.
As a founder, your greatest challenge is finding a way to walk along two parallel paths simultaneously. The first path is working on the thing you’re actually building and the business itself. The second path is empowering the people you bring along with you in your journey (particularly on the front lines) to catch the vision of what you’re doing and, most of all, feel safety and security every step of the way.
It’s very rarely easy, and you’ll fail countless times. What matters, however, is that you prioritize your people and how you lead them, in addition to growing your company.