The 10x Founder: Jack of All Trades
The 10x Founder: Jack of All Trades
Why being a generalist and lateral thinker will help you become a better founder.
Back in July of 2019, a meme was born from a Twitter thread from Accel India general partner Shekhar Kirani. It was widely mocked and ridiculed by those who thought that the concept of a 10x engineer was rooted in unhealthy and unrealistic expectations of engineers. Kirani was attempting to call out what would make an ideal engineer, one who is focused, efficient, productive, full-stack, quick to learn and extremely knowledgeable about their code. But he also stereotyped them as unable to work with people (hate meetings, poor team players, bad mentors). While he probably was well-intentioned with his thread, it came across very poorly and the Twitterverse had a field day with it.
While there is no such a thing as a perfect or ideal founder, there are traits and habits that can make a founder more productive and effective. This essay is not meant to be prescriptive but instead inspire self-reflection on how being more of a generalist or partnering with one might benefit you and your business as you build it.
Jack of All Trades, Master of None
The political scientist and author Philip Tetlock has suggested that being a jack of all trades and master of none might not be a bad thing. The old Greek saying goes that “The fox knows many things, but the hedgehog knows just one thing.” A fox may come up with a hundred ways to attack the hedgehog, but the hedgehog can just curl up in a ball and wait for the fox to get bored and give up. In his books, Superforecasting: The Art and Science of Prediction and Expert Political Judgment: How Good Is It? How Can We Know?, Tetlock suggests that leaders who are broad thinkers and generalists (foxes) make better predictions and more sound decisions than do rigid and specialized thinkers (hedgehogs). Because foxes are able to live with uncertainty and adapt, they can see the future more clearly than hedgehogs who are more likely to be fanatical and dig their heels in.
Personality Tests and Polymaths
I recently took the Enneagram personality test during a leadership coaching session. My results were #7 The Enthusiast. From the Enneagram Institute:
Sevens are extroverted, optimistic, versatile, and spontaneous. Playful, high-spirited, and practical, they can also misapply their many talents, becoming over-extended, scattered, and undisciplined. They constantly seek new and exciting experiences, but can become distracted and exhausted by staying on the go. They typically have problems with impatience and impulsiveness. At their Best: they focus their talents on worthwhile goals, becoming appreciative, joyous, and satisfied.
Basic Fear: Of being deprived and in pain
Basic Desire: To be satisfied and content — to have their needs fulfilled
Key Motivations: Want to maintain their freedom and happiness, to avoid missing out on worthwhile experiences, to keep themselves excited and occupied, to avoid and discharge pain.
When I read through the profile description, it was eerily accurate. It was as if the Enneagram Institute had been monitoring my whole life and peering into my soul this entire time. To be honest, it was a bit deflating to know that I was so predictable and fit into a box. At the same time, it was liberating and eye-opening to see my personality type analyzed so explicitly. It explained why I am the way I am, and why I behave the way I do. Enthusiasts are one of two personality types that are most likely to become entrepreneurs because they are future oriented (Challengers being the other, coincidentally my cofounder is a Challenger). From another Enneagram profile of Enthusiasts:
“They are practical people who have multiple skills. They know how to network and to promote themselves and their interests. They often have an entrepreneurial spirit and are able to convey their enthusiasm to those with whom they come in contact. When they are able to focus their talents, they are often highly successful.”
My enneagram personality test result reinforced why I have so many interests and value variety and versatility.
I had always assumed that depth of knowledge was more powerful than breadth of knowledge. We are raised to believe that someone who is an expert at something is superior to someone who is an expert at nothing. A professional cellist is better than someone who can play five instruments really well. You will never be really good at anything if you don’t hyper-specialize and spend 10,000 focused hours practicing it. But then I realized that there’s a need for both specialists but also for generalists who can integrate and think about the bigger picture. It’s the composer or conductor who has played multiple instruments who is able to orchestrate and coordinate the cellist with other musicians to make a masterpiece. A professional musician can play music beautifully but they may not be able to compose or create music. This is the biggest challenge when musicians attempt to play jazz music which often requires improvisation.
The people I enjoy talking to most are those who are able to engage across a wide range of topics and interests: polymaths. My friend Eugene Wei is a well-respected thought leader in Silicon Valley. His epic essays (occasionally tomes) are masterpieces, fluidly integrating and weaving ideas from various domains from technology to entertainment to philosophy and more. Eugene has been blessed with the powerful gift of being a good writer which allows him to elegantly articulate his ideas. For example, in a single blog post he talks about a recent translation of The Odyssey, the explosion of podcasts, how the rising supply of content is impacting the entertainment industry and the democratization of sports content. I doubt you will ever find another blog that mentions Homer, Adam Sandler, Logan Paul and Kyle Schwarber in the same post. Eugene majored in both English and Industrial Engineering (Both fuzzy and techie) at Stanford and after being a product manager at Amazon he went back to get his MFA in film from UCLA. He went on to run the early product, design, editorial, AND marketing teams at Hulu. More recently he was Head of Video at Oculus (Facebook). Eugene is basically a walking New York Times, informative about every topic from business, sports, food, technology, entertainment, politics and more. Needless to say, Eugene has been able to leverage his lateral knowledge and thinking to build some world-changing products.
The book Range: Why Generalists Triumph in a Specialized World by David Epstein talks about how people can benefit from broad knowledge of different topics when trying to solve problems. When a person spends their life focused on one domain expertise, it limits their ability to think outside of the box and come up with creative solutions because they default to pattern matching. Bringing in knowledge outside of a domain expands the universe of possible ideas and patterns for a better solution. This book made me feel validated. It was okay not to be an expert or specialist. Having broad general knowledge and experience gave me special powers and insight to integrate ideas and come up with better solutions. As an entrepreneur, this is an ideal trait to have because when you see a problem, you can iterate through any number of ideas to solve it from various domains and analogous solutions.
“Whether the task is mental or physical, interleaving improves the ability to match the right strategy to a problem. That happens to be a hallmark of expert problem solving…
Analogical thinking takes the new and makes it familiar, or takes the familiar and puts it in a new light, and allows humans to reason through problems they have never seen in unfamiliar contexts. It also allows us to understand that which we cannot see at all.”
Robin Hogarth, a prominent professor of decision science, writes about kind and wicked learning environments in his paper “The Two Settings of Kind and Wicked Learning Environments”. In kind environments, there are patterns and rules with rapid feedback that make things somewhat safe and predictable. In wicked environments, patterns are not repeated or obvious, there are no clear or complete rules, and feedback is delayed and inaccurate. Experts fare very well in kind environments, but not so well in wicked environments. When starting a company to solve a problem that hasn’t been solved before, you are likely working in a wicked and unpredictable environment. Most breakthroughs and innovations come not from experts, but from newcomers, because they don’t have all of the baggage and tunnel vision that experts have.
“Beneath complexity, hedgehogs tend to see simple, deterministic rules of cause and effect framed by their area of expertise, like repeating patterns on a chessboard. Foxes see complexity in what others mistake for simple cause and effect. They understand that most cause-and-effect relationships are probabilistic, not deterministic. There are unknowns, and luck, and even when history apparently repeats, it does not do so precisely. They recognize that they are operating in the very definition of a wicked learning environment, where it can be very hard to learn, from either wins or losses.”
Prisoners of Our Prototypes
In his paper, Reconsidering the Trade-off Between Expertise and Flexibility: a Cognitive Entrenchment Perspective, Rice MBA professor Eric Dane’s research shows that the more domain expertise and experience someone gains, the less likely they are to adapt, solve problems and come up with new ideas. The more ingrained certain ideologies are, the more difficult they are to let go.
Psychologist and Wharton professor Adam Grant does a fantastic job of breaking down why experts struggle with creativity and originality in his book Originals: How Non-Conformists Move the World:
“Although child prodigies are often rich in both talent and ambition, what holds them back from moving the world forward is that they don’t learn to be original…Practice makes perfect, but it doesn’t make new…The gifted learn to play magnificent Mozart melodies and beautiful Beethoven symphonies, but never compose their own original scores. They focus their energy on consuming existing scientific knowledge, not producing new insights. They conform to the codified rules of established games, rather than inventing their own rules or their own games.
…The least favorite students were the non-conformists who made up their own rules. Teachers tend to discriminate against highly creative students, labeling them as troublemakers. In response, many children quickly learn to get with the program, keeping their original ideas to themselves. In the language of author William Deresiewicz, they become the world’s most excellent sheep.”
Most cultures, if not all, promote and reward achievement above failure. Focus on achievement leads to a desire for guaranteed success because the path is clear and predictable. The downside is that not encouraging taking risks and acceptance of failure results in less originality and fewer unique accomplishments in the world.
Grant points out that it’s when people have moderate expertise in a certain domain that they’re the most open to radically creative ideas. Creativity comes from the unique combination of both broad and deep experience. He talks about a recent study of Nobel Prize-winning scientists from 1901 to 2005 with typical scientists across the same period and found that while both groups had deep expertise in their respective fields of study, the winners were far more likely to have been involved in the arts. Another study of thousands of American inventors and entrepreneurs showed similar results. People who started businesses and contributed to patent applications were more likely to have hobbies that involved creative thinking such as painting, architecture, literature, sculpture and drawing. Though I don’t get to draw as much as I used to in my youth, I’ve found my creative outlet in photography.
“Interest in the arts among entrepreneurs, inventors, and eminent scientists obviously reflects their curiosity and aptitude. People who are open to new ways of looking at science and business also tend to be fascinated by the expression of ideas and emotions through images, sounds, and words. (The personality trait most associated with an interest in the arts is called openness, the tendency to seek out novelty and variety in intellectual, aesthetic and emotional pursuits.) But it’s not just that a certain kind of original person seeks out exposure to the arts. The arts also serve in turn as a powerful source of creative insight.”
Professor Grant goes on to show that immersing oneself in different cultures and values also promotes originality and creativity. Highly creative adults tended to move to new cities far more frequently than their peers in childhood, which encouraged flexibility and adaptability. The more different that foreign culture was from their native land, the more impact it had on their creativity. Another factor was the length of time spent abroad in those cultures, just traveling and visiting for vacation isn’t the same as living there for several years.
Accepting failure, having open and creative outlets and immersing yourself in distinctly different cultures from your own will help you to be more innovative and ultimately a better founder.
Wearing All Hats
I’ve now started two different companies. When you start a company, you are forced from day one to be a generalist wearing different hats regardless of personality type or proclivity. I have coded websites. I have closed sales deals and business development partnerships. I have designed logos and wireframes. I have managed performance marketing campaigns and e-mail drips. I have written hundreds of PRDs (product requirements documents). I have answered customer support phone calls and e-mails. Did I know how to do all of these things before I did them? No way. But as a founder, you have to because no one else will. You also should do them, because this is the only way you will really know what your company needs. Rolling up your sleeves and understanding each and every part of your business will make you a better founder and leader. People respect a leader who can empathize with their challenges and frustrations. When you wear different hats, you’re wearing the hats that your future team members and employees will be wearing. More importantly you are learning first-hand what your customers want which is critical for a founder to be successful.
A 10x founder has no fear about taking on these different roles because they know how important it is to the company (and they actually enjoy wearing different hats). They will learn how check in code to GitHub or design collateral in Sketch or respond to tickets in Zendesk or manage campaigns in Google Ads, because that’s their job as the founder…to care about all of these things. A team or organization is ultimately functioning as one coordinated entity or body that is responding to and serving the needs of the end customer. When the founder has experienced what the right foot and the left foot are feeling, they can better anticipate what needs to happen to make the body move forward. By closing sales and responding to support calls, the founder understands their customers wants and needs. That understanding translates to better product and design decisions and more relevant marketing campaigns. A founder who understands all the areas of their company is more responsive and agile than one who does not.
Another benefit of having exposure to different areas of the business gives a founder insight into who they should be hiring to lead in those departments. They will have insider knowledge on what kind of person it takes to do the job and do it well. This ideally leads to fewer erroneous hires and friction for the team. It also allows the company to grow faster with the right leadership in place. A head of sales who has experience selling to enterprises is very different than one who has sold to SMBs (small-to-medium businesses). A VP of Marketing from a retail or consumer brand will have little idea how to market enterprise software to executives of corporations. As the founder, once you have closed multiple sales or run marketing campaigns, you will have more insight into who you need to hire.
Many people reading this may dismiss it because it’s not efficient for a leader to do everything. They think it isn’t the best use of time for a founder to learn how to code or use design software. The goal isn’t to become the lead engineer or head designer. The purpose of learning these tools and understanding these domains is to make you a better problem solver. Your role as the founder is the Chief Problem Solver of the company. I’ve met many founders who were deeply knowledgeable about one specific domain expertise. They ranged from scientists with a PhD to seasoned sales veterans to professional athletes. Each of them had a great idea, but were unable to execute because they only ever knew how to do one thing really well their whole lives. This is not to say that there aren’t many examples of experts who were able to build great companies, they just had to become generalists or partner with one. You could be the greatest chef or fashion designer in the world, but if you don’t know how to run a restaurant or promote your clothing designs, no one will ever know. To become successful you need to either broaden your skillset and domain knowledge or tap into your network to find others who can help.
“Lateral thinking is a term coined in the 1960s for the reimagining of information in new contexts, including the drawing together of seemingly disparate concepts or domains that can give old ideas new uses.”
— David Epstein, Range
Lateral thinkers are able to leverage their knowledge base of myriad topics and apply learnings across domains. In the past several years, I’ve fallen in love with the game of golf. Golf was something that I scoffed at in my youth. But once I took lessons with my wife, I was hooked. It is a game of skill and strategy. It is both frustrating and exhilarating. Most importantly, I’ve taken my learnings from golf and translated them to my career. The same could be said for my love of basketball and how I’ve applied what my favorite NBA team has done to building a winning company culture. When you understand how different things work and how to succeed, you start to translate and apply those learnings to everything else.
Be More Foxy
I believe that while it’s possible to start a company as a specialist with deep knowledge and expertise, the road will be more difficult. I’ve met many a hedgehog founder who had a brilliant idea but was unable to productize it or come up with a go-to-market plan. These were top-of-their-class PhDs from the best schools or veterans of industry. It would benefit these types of founders greatly to partner with a generalist and could help come up with ideas and execute.
You may not be a generalist, fox, polymath or enthusiast, but that does not mean that you can’t learn from them. If you are a specialist or focused on one area of expertise, take time to learn a new hobby or read about other topics. Open your mind to ideas and new domains. It’s like writing a term paper. You spend weeks writing and staring at the same sentences over and over again until it all becomes a blur. It will only get worse if you keep toiling away on it. When that happens, you need to step away and take a break from looking at it. After you revisit it again with fresh, rested eyes, you will begin to see how you can make improvements. Just like the paper, the more you bang your head trying to do the same thing or repeating the same patterns, the more you will drive yourself mad going nowhere. Instead, spend time thinking about other things and learning fresh perspectives, and you are bound to inspire bigger and better ideas. You never know when you’re stuck in a rut what will snap you out of it.
Ask friends to recommend new content for you. Read books about topics you’re curious about or would not normally read. Listen to podcasts that aren’t in your regular rotation. You’re here on Medium, go explore essays in different topics. Visit a new country outside of your comfort zone. Meet someone outside of your social circles. The more you expand your reality, the more likely you are to be inspired to think differently than your typical routine allows for. If you are talking to the same people or reading the same content all of the time, why would you expect to come up with anything unique or new. Variety and expansion of ideas and experiences leads to innovation whether you need inspiration for a new business idea or a catalyst for a breakthrough in your current business.
Conclusion
Gunpei Yokoi was a machine maintenance man turned game designer for Nintendo in Japan. He was credited for taking cheap LCD calculator technology and adapting it to successful game watches and handheld games that were the precursor to his invention of the Game Boy. “I don’t have any particular specialist skills,” he once said. “I have a sort of vague knowledge of everything.” Yokoi brought together existing technology and parts to create something entirely new and groundbreaking. He advised young employees not just to play with technology for its own sake, but to play with ideas. Do not be an engineer, he said, be a producer.”
There are countless examples of founders and entrepreneurs who have started successful businesses they had no business starting in the first place. They were outsiders who didn’t carry the baggage of being industry experts and effectively translated their experiences into a different domain. Being able to laterally think across systems and having a breadth of experience (including creative outlets and hobbies) allowed those founders to come up with ideas that those entrenched in the same ideas and culture for decades were incapable of seeing. The more you expose yourself to different cultures, different industries, even different parts of even your own startup, the more clearly you will be able to connect and formulate great ideas to succeed as a founder.
“If you’re gonna make connections which are innovative, you have to not have the same bag of experience as everyone else does.”
- Steve Jobs