A lot of the world’s great entrepreneurs focus their careers on one specific domain, dedicating themselves to building the world’s best [INSERT SECTOR HERE: insurance claims processing software, oatmeal stout, sliding bevel] company.
Not me. I find most businesses fascinating. To me, the process is the product. The act of creating the company gives me the juice. Just being around great people and making it all work. (You can tell because I’ve done software AND software.)
So when my original idea for my current company didn’t stir up interest from potential customers (and hires), I tried not to get my panties in a bunch. My cofounder Erik and I went back to the trough for more ideas. The most important thing was to find a place where we could be the best. Getting too attached to one idea would be a problem.
Being deep in mobile development software, Erik brought a new idea around the large-scale development of mobile apps that was a perfect fit for him given his background. We followed the breadcrumbs on the idea and got a lot of positive responses from folks in the know. Just one catch: unlike my original idea which I understood well, I was a bit out of my league on this technology.
I would have to dig in and learn a new space.
How I Approach It
I’ve always been a business leader, not a technologist. My strengths are strategy, leadership, sales, marketing, product positioning, blah, blah, blah. My weak point is engineering depth.
A CEO doesn’t need to be an engineer–and sometimes too much depth can be a problem–but too little understanding will be a train wreck. You need to be very willing to learn and eat your own dogfood, but you also need to hit the right level of knowledge. Think about it like the earth’s makeup:
Crust (the “what”): At this level (common to many salespeople), you get the main concepts, but not why they were created or how they work together. You can speak about the topic but usually need someone else to jump in and help with questions.
Mantle (the “why”): You can speak intelligently about the concepts and design decisions. You understand the entire architecture, but you don’t go deep on the constituent parts. Like owning a house, you should know why you have a roof and how it is constructed to fit with the rest of the house and when it needs replacing, but you don’t need to know what type of flashing was used or the shingling technique.
Core (the “how”): You get how the whole enchilada works together at every level (what, why and how) and can go wherever the conversation goes. People who build the product exist at this level and can answer any question, but there’s a risk of getting too deep (which can hinder decision-making).
As a CEO, I strive to live at the mantle. I like to know how everything fits together and to be able to speak the language, but going too deep in one area will take away from my big picture perspective, thus making it hard to make the best decisions. And it’s probably an indication I’m spending time on the wrong stuff.
How It’s Going So Far
There’s a scene from a classic Simpsons episode where Homer is trying to help get business for a friend’s bowling alley. He does some research. First you see him reading “Advanced Marketing.” Then “Beginning Marketing.” Then he’s looking up “Marketing” in the dictionary. That’s how I felt at first.
But I’ve kept on it. I’ve started coding for iOS and Android, learning Swift (Apple’s new dev language), researching complex computing concepts, taking online classes in data management and structures. And pitching people over and over. It’s like an immersion program for a foreign language – study hard and try it out on real people. You have to risk having egg on your face to make progress.
It can be frustrating. My partner’s knowledge flowed like wine while I was like a bottle of Heinz 57.
But gradually things start to change. It actually starts to become fun. And it starts working. Before you know it, you can chew the fat with the best of them.
So, my advice for CEO’s like me: dig in deeper than your comfort zone. But not so deep you lose perspective. And use middle school geology and food metaphors whenever you need to make a point and/or are on a calorie restriction diet.
I recently tried to recruit a few engineers to my (at-the-time-not-even-incorporated) stealth startup. They had unexpectedly become available, and I was scrambling to make a case for them to come on board during the short window of opportunity. But despite my best hand-waving attempts at painting a picture of what could be, I couldn’t convince them. They needed structure and we were a gelatinous blob of ideas, the primordial ooze of entrepreneurship. They rejected us.
It’s hard not to take rejection personally. Like dating, you start building the rejection into your personal narrative that something is inherently wrong. In this case, it would be easy to go to the “you don’t have what it takes anymore” place. But I caught myself. I wanted a different story.
The theory of Narrative Identity and field of Narrative Psychology describe how we absorb information by using it to weave a story for our life. Plots, characters, themes and meaning tell us who we are in the moment and who we can become. It can serve our happiness – or it can be the cause of our downfall.
When my high school basketball coach told me I wasn’t good enough to shoot the ball (“just pass it … quickly!”), I began to believe the story that I was not a coordinated individual, that I was just a rebounder and defensive thug. Later in college, when playing with people I liked in a relaxed atmosphere, I could hit two-thirds of my 3-pointers. It was then that I first realized we have a lot more control over situations than I had understood. And that thug life wasn’t my destiny.
Some of the most successful entrepreneurs are master storytellers. Think of the founding mythology (aka “the creation myth”), the near-death encounters, the fundraising pitches and the recruiting and on-boarding vision. We’re often more dramatic than the 60’s Batman show in our delusional yarns, but good storytelling is how we pull in employees, investors, partners and customers. It’s gas in the company tank.
Adam West at his Best
That said, we rarely take time to step back and consider the story we’re telling about ourselves, and how much it may be holding us back.
At Jive, we used to do an annual ski trip to Mt. Hood from Portland. The first time we did it, everyone could squeeze onto one bus for the hour-long drive. On the way back, that bus became a debauchery bell curve – the tee-totalers in the front, people enjoying themselves lightheartedly in the middle, and a whiskey-soaked wrestling match in the back. And I naturally gravitated to the hard-core revelers. Hell, I was leading the drinking games. Just too much fun to miss.
The next year we had two buses. Just like before, I settled in on the vice-side of one of the buses, cracking jokes and preparing to get the festivities going. Then I saw a sidewise glance from one of the front-of-the-bussers. In a moment of clarity, I realized this character I was living out wasn’t going to work anymore. I had to step it up and be the leader they could all look up to. I moved to the middle.
By the time the third annual trip rolled around, we had three buses. And my story needed to change yet again. This time I would work the aisles, making sure everyone was doing well, enjoying themselves, foregoing my own pleasure for the sake of the team. I would make sure people didn’t get out of control, that we weren’t going to lose our insurance (we did anyway), and that people were bonding with each other. It was time to be at the front lines, taking the bullets.
The better I got at understanding and owning my story, the sooner I was able to get out of my own way and be what the company needed. The world was giving me the raw materials. My job was to spin it into an inspiring tale that I would follow, and that could be used to make better decisions. More Atticus Finch than Ignatious J. Reilly.
Getting rejected by the engineers was not a bad thing ultimately – it was part of the conflict that makes the story interesting. In this case, rejection pushed us in the right direction – to recognize that our thinking was too early for those recruits, that we need to be patient, and that whomever we bring on this early must do it for the people (and must dig the ooze).
People often refer to “a new chapter” in their lives. I prefer a book of short stories – there’s more room for change and growth, while not losing your core. This time around, owning the story is key to enjoying the ride….and succeeding.
Will the patience wear thin? Will the whole thing fall apart? Will Batman really marry the Queen of Diamonds? Tune in next week.
Impatience is the gas that fuels entrepreneurs to get stuff done. It drives us to fix bugs, solve customer issues, fire people quickly and keep projects on track. An entrepreneur without impatience is just weird. Like a longshoreman without facial hair.
Unfortunately, though, when it comes to achieving big, hairy growth goals, an entrepreneur’s impatience can lead to disastrous results.
As I embark on my next company, I have the urge to jump to the conclusion quickly instead of “living in the moment.” People like me who are on our second-plus startups are especially prone to wanting everything to be complete and perfect out of the gate. As a result, I started writing down my ideas on patience to help keep me grounded.
Dangers of Impatient Scaling
Premature Scaling happens when startups so anxious for growth build up big operations around larval business models that weren’t meant to see the light of day. Founders often think they’ve “cracked the code,” but have really only cracked the seal on a few random data points. It’s like they picked a steering wheel up off the ground and started trying to drive with it. The Startup Genome Project has called premature scaling the number one cause of failure.
Even worse than scaling too fast and early is what I call Flailing Scaling. This is what happens when entrepreneurs who are stressed about growth and making numbers frantically apply whatever business model sounds good that week. They have the attention span of a black lab puppy at a tennis match, and it costs them. Every switch brings a new round of hiring, firing, investing and blowing through all their cash. It’s like buying a new car every time you get a flat tire.
Benefits of Patient Scaling
The good kind of scaling requires lots of patience… and a bit of pain, too. It’s no accident that the Latin root of “patience” means suffering. It sucks to wait.
You need to collect much more information than you think before making big investments in growth. The author Jim Collins calls this “fire bullets first, then cannonballs.” Or, for those still close to your college days, “beer before vodka.”
At Jive, we were fortunate to have ideal conditions for patience. We bootstrapped the company for five years, and had no investors breathing down our neck for growth. We had the freedom to experiment. We aggressively went after two different markets that we thought would be huge. Both ultimately fell flat, and we had to go back to the drawing board. But we did the whole thing on cash flow and without hiring anyone new. If we had raised money earlier and/or from the wrong people, we would have been forced to grow into one of those false directions–hiring salespeople, building partners, building our support group–and would have killed any value in the company.
But we had our share of problems with impatience too. After we finally found our market and raised funding, we hired our first field sales rep (read: expensive hire). That person immediately sold a seven-figure contract. After removing my lips from the champagne bottle, I decreed: “we gotta hire a bunch of these guys.” We did. And none of them did a seven figure deal, including that original guy. Or even close. We had to replace almost all of them, and it cost a mint. Clearly a failure of patience. And clearly a “false-positive” on the one data point I had.
Evolutionary psychology says patience is the ability to choose between smaller short-term rewards versus larger long-term ones. (Like the kids who can wait for two marshmallows instead of shoving one in their mouth right away.) From an evolution standpoint, how animals get their food may determine where we fall on the patience spectrum. Humans were both hunters (short-term) and farmers (long-term), so we are capable of waiting an entire season for beans, but also inhaling a box of Milk Duds in less than a minute.
If patience is so unnatural for entrepreneurs, how can we develop it?
1. Intentional practice: Recognize that patience is (probably) not a natural inclination of yours. Build into your plan a longer timeframe for making growth decisions. Notice your tendency to react quickly, and make sure it’s only for the small stuff–not things that are hard to unwind later.
2. Reframe the story: Instead of getting all keyed up around growth, channel your energy towards experimentation and data collection. Let that become the big metric on your whiteboard in the early days, not sales numbers. When you start saying things like “we need to hire a head of sales to grow” or “we found a repeatable formula,” put yourself on trial to prove it.
3. Relieve Pressure from the Outside: You may have impatient investors who are adding to the stress. Many of them think they’re being helpful by pushing you unnaturally for growth. If you do a good job reframing the story (see #2), your job is to communicate that effectively and get investors on board with the journey. You don’t need a football coach at this stage. You need another scientist looking at the data.
4. Relieve Pressure from the Inside: You might be bringing your own baggage to the equation. Your insecurities and desire to look good to others can drive unnatural behavior. It’s a much deeper topic, but my point here is to recognize where your motivation is coming from and not let it get in the way of the right decisions.
5. Find a Model: Talk to companies that did it the right way. Occasionally companies drunkenly stumble on a perfect model early, but usually there’s tons of experimentation and mistakes. Ask and learn, ideally from companies that are similar to yours.
Hopefully at some point, we get to the point of aggressive scaling where the infrastructure and market are in place to hit the gas. In the meantime, I need to practice the mantra from Ben Franklin, himself a pretty bad-ass entrepreneur: “He who can have patience can have what he will.” And that counts for she too, btw. (But not the longshoreman comment.)
Now that I’m doing it again, I am remembering how cooking up a good idea for a company is harder than finding a pro athlete at Comic-Con. So I find it helps to follow a recipe. This one was adapted over time from conversations, experience and observations cobbled together from other entrepreneurs.
Experience can help the process — “pattern recognition” helps the experienced folks understand what works and what doesn’t. On the other hand, some veterans (for example, me) have seen so much that they’re jaded and knock down their own ideas before they try them.
After a long slog, I’m learning the right formula: part process, part mindset, part art, part science. Enjoy!
1 cup youthful idealism (keep on hand; I run out a lot)
1 good network of relevant people
3 handfuls creativity / ability to connect disparate ideas
1 premium partner (note: can substitute meditation and/or therapy)
1 helping of presentation skills
3 fistfuls fire in the belly
1 pinch compartmentalization of life / focus
1-3 ideas (half-baked)
3 crates patience and self-appreciation (note: don’t substitute alcohol here)
1 set of blinders (to protect you from worrying too much about competitors; can substitute more youthful idealism if you run out)
1 blog to use as therapy
Take out all your motivations, and set them on the table. List your goals and motivations for starting a business. What do you need (e.g. short commute, less travel, caffeine drip) and what do you NOT need (e.g. small number of customers, overbearing board, haters).
Then take out all your assets, and put them next to your motivations. Who could you pull together on a team? Advisors? What are the big gaps? Do you have seed capital? Or access to capital? What are your strengths and experiences? In what area could you be the best in the world?
Assemble your current ideas. Make a list of 30 (it’s possible).
Start working through the ideas with your partner. If you don’t have a partner, set up brainstorming meetings with good people. Too much solo time and you’ll end up with a lopsided mess. Consider a personal board of directors. Turn your 30 ideas into five.
Shape them. Connect the dots between new technology and business model trends to your area of choice. See what happens. Then add in the seasoning of your experience and background.
Sift through your ideas. Use a good sieve to filter out the excess (but nothing so tight that prevents everything from getting through). Consider the strength of the idea, your passion/purpose and your ability to execute on it. Once you start adding things like your personal brand, your existing network and potential competitors, you’re over-sifting. Ideally, one idea will naturally rise to the top, but you can take two if needed.
Step back. Instead of forcing everything through a rigid process, occasionally remove yourself to look at where people (you, your partner and anybody else you have involved) seem to be heading on their own. Is there a natural gravitational pull that you’re missing? I recently had the head-slapping V-8 moment when I realized how I was forcing ideas onto a likely team who wouldn’t love them.
Research other businesses in the space. But avoid getting overwhelmed. Too much reading about competitors makes the idea lose its flavor. Inspirational reading preserves the taste.
Form the raw materials into a functional presentation. Turn the idea into a practice pitch. This doesn’t have to be TED-worthy. Just good enough to get the feedback you need.
Do a taste test. Find good people who understand the space and present the ideas while asking as many questions as possible.
Keep an open mind. If the conversation starts going in another direction, consider running with it. This kind of intuition is what you need to make a great idea.
Capture pain points. As they come up, latch on to them like a lamprey giving a hickey. Keep asking questions to dig in on that pain point. Note: without this step, the whole recipe could fail. Ideally you want to start matching up pain points from various potential customers.
Stay on the lookout for something small but solvable. If you find those small pain points that affect everyone, but haven’t been solved, you’re on the right path. At least in Silicon Valley, too many people look for the billion dollar idea. But the path to a billion always starts with a million-dollar idea.
Be open to serendipity. Once you start moving with purpose in a direction, you leave yourself open to luck. The week I started looking at hospitality software as an option, I came across a mid-sized hospitality software company 10 minutes from my house that was willing to sell itself. It didn’t go through, but these things happen surprisingly often when you’re on the right path.
Run the idea through the Stop / Start / Continue machine. Is the idea on the right track? You can either stop and move on to the next idea, start building this idea or continue on the process of validating this one.
Bake. Congrats. You’ve now gotten your idea to the point where you’re ready to start cooking. It won’t be perfect (it never is). It will likely change many times along the way. But it’s good enough to put in the oven.
Now go eat.
Over uncharacteristically cheap beers in San Francisco with my Dad the other day, we got to talking about a common problem for leaders. That is, after some success, many people start believing their own BS. Instead of having a carefully constructed work persona that can be removed as needed, they start to become the image of themselves, and it sows the seeds of cultural destruction for their organizations.
I’m very familiar with this problem. It stumped me as a leader, and I notice it quite frequently in others and even in public figures (see Donald Trump). Here’s how I see it.
First, a Big Premise
We are all very complicated.
Modern culture forces quick classifications (aggressive entrepreneur, artistic dreamer, salty mailman, etc.), and as a result we start to believe those words about ourselves and others. It’s how we differentiate in a mass society.
The truth is that our inner lives are incredibly deep and intricate. We’ve got the Marianas Trench inside of us, but we spend most of our time wading around the shore like a TV commercial for retirees.
Just look at your dreams as a testament to how deep it goes: as you sleep, you’re riding a talking bull over Tokyo while escaping Russian cosmonauts and your grade school teacher. And then you wake up and eat cereal.
As the philosopher Heraclitus said:
“You could not discover the limits of the soul (psyche) even if you traveled every road to do so; such is the depth of its meaning.”
Understand your Deeper Waters
So how do we understand this complexity? There are many ways, but I’ve found Jungian archetypes to be helpful.
In case you slept through Psych 101 or skipped the “what’s the matter with me” phase of adult life exploration, Carl Jung believed we are born with a common set of images that determine our perspectives of the world and our moods. They include figures like warrior, mother, trickster, child and wise elder as well as archetypal motifs (like the deluge) and life events (like birth and marriage). We each associate with these archetypes based on our circumstances and personality. They act like Gods who push our attitudes and behavior.
The upshot is that we have a whole soccer stadium full of energies inside of us. Like Mary Poppins’ carpetbag, it’s an infinite chasm we draw from, and our ego chooses the energy we need based on the situation.
Your Organization is a Reflection of You
It turns out, businesses are just as complex as the people who comprise them (someone should do a blog on what a business dreams about). And when you as a leader start to associate with one image above others, it takes over your sense of self, and your organization, like a disease. As the psychologist James Hillman said in Revisioning Psychology:
“Absolutely essential to the notion of archetypes [is] their emotional possessive affect, their bedazzlement of consciousness so that it becomes blind to its own stance.”
In other words, getting stuck in the image of an archetype is a form of possession. And short of calling up Max von Sydow’s character from The Exorcist, it’s hard to escape.
You probably know people who get stuck in patterns like this: Tricksters are those who can’t obey the rules, puers can’t grow up (Peter Pan syndrome), martyrs live to serve only others, heroes have to save the day for everyone, mentors guide others but rarely act.
The Seduction of the Warrior
One archetype that a lot of business leaders (including me) lean towards is the warrior. This is the driven, linear, goal-oriented, do-whatever-it-takes, decisive, aggressive attitude of winning. It’s the reason we survive and achieve goals. It’s how we win deals. It’s why we use battle and sports metaphors and build a spirit of solidarity by being in the trenches together (see! a war metaphor). It’s an intoxicating blend of characteristics. A business without warrior energy will likely fizzle quickly.
I wouldn’t be who I am today without my warrior energy. From winning football games to surviving bar fights to thriving in business, it’s a part of who I am. It’s gotten me through the difficult times, and I love it.
But like many others, I have lost myself in this role, and I see it happen with entrepreneurs a lot. He or she has achieved some success, but in doing so, can no longer separate their identity from the organization and have a hard time seeing their weaknesses.
The mask won’t come off. That’s the real danger. Perhaps it is the only place they have ever felt at home. They are a winner and people treat them as one. But they are also stuck in an infinite loop of an assumed identity.
And you end up building a culture that is unsustainable. For example, you might over-focus on making money as opposed to innovating, which could win the battle but lose the war. You might create a competitive culture where a narrow set of attributes determine success and lose great people who don’t fit the mold. You might build power structures that are impenetrable and lose track of how people are doing.
Stay Unique and Complicated
Jung called our social roles our “persona.” This is the Latin word for the (often creepy) smile and frown masks Romans wore to the the theater. It literally means “to sound through” because the actors spoke through the masks. For Jung, the persona is the part of the person turned toward the public. But it’s just that – a mask, not your self.
If you feel in danger of melding permanently with the mask, look in the mirror and ask yourself: Are you playing the role the business needs, or are your selfish needs getting in the way? Can you adapt to the situation, or are you viewing everything through the same lens? Have you fallen in love with a single persona? Can you remove your work persona easily when you’re not there, or is it interfering with the rest of life?
Granted, these are especially complex questions at a time when leaders are increasingly encouraged to be “authentic” and approachable while managing twenty people, juggling 743 tasks and getting sued. Not to mention the fact that the lines between work and the rest of life have blurred beyond recognition.
But I believe we can do it. It takes strength to draw from archetypal energies and do the hard work that is required of us. But it actually takes more strength to break out of those molds and be truly authentic. That to me is one of the most important challenges of any leader. As the philosopher Hegel said:
“For man is this: not only to carry the contradiction of multiplicity within himself, but to endure it and to remain equal and true to himself therein.”
So, you know, keep it real.
Face-to-face collaboration is a must for me.
Readers of this blog know that I’ve started working on my next company. I have a number of ideas, but I need people to work through them with me. When I’m working with people I respect in front of a whiteboard, the results of the effort are tight, well formed business ideas. If I’m by myself in front of the same board, I’m like a gorilla with a can of spraypaint.
To avoid the crippling insanity of solo work, I’ve been scheduling as many conversations as humanly possible – essentially hopping from stone to stone across Rio del Loco. These past months have been a pride-swallowing endeavor to reach out to anyone and everyone for feedback.
So when a couple of close friends suggested I assemble a “personal board of directors,” it got me thinking.
The concept is to have a group of people who know you well, and who will help you steer your life in the right directions. Unlike a company’s board of directors, your personal board is accountable to you – not your investors or shareholders. They help you stay true to your values and purpose, and make sure you avoid bad decisions.
Want to rebalance your life? Talk to the board. Considering writing a book? Board. Thinking about becoming a goat herder in Bhutan? Board, dude.
The idea – attributed to Jim Collins – is a good one. For one thing, we all need honest input. Close friends and family will love you no matter what, but they’re generally overly supportive and lacking context. You need tough love from people who know you well, will hold you to high standards and can help you connect the dots between your values and complicated career decisions.
When I started thinking about how to set up my personal board, I looked for examples. But it turned out I know as many people with personal boards as I know people into noodling. So I came up with my own structure:
Who are my board members?
I’m recruiting people with different perspectives who understand me at a deeper level. I’ll protect identities, but here is a description of the six people I have enlisted so far:
A former CEO like me who is 17 years older; he can laugh at my mid-life rantings.
A colleague I have worked with for years who understands my humor, style and ideal culture.
A good friend whose life and values are similar.
A fellow tech investor, life explorer and running friend who helped come up with the idea.
My first business mentor and good friend who brings a strategic, non-Silicon Valley mindset.
My uncle’s life-partner, a former CEO who knew me before I could walk, and one of my favorite people.
I’ll probably add one or two more, but more than that seems excessive.
How will they help?
Complex career thinking: As I age, life questions become a richer composite of desires and character traits (just in case you couldn’t tell from this blog). I need sound advice.
Big questions: My team will help with transitions, freakouts, life planning and general brainstorming.
Raw inspiration: An additional source of motivation when I need it most.
Accountability: People to hold me to big goals when no one else is there to do it.
What I wouldn’t use them for is feedback that’s too specific to the business. My fear would be that they start acting as company advisors, and not personal advisors. Or worse, they’d get emotionally invested in the success of the business. Feedback on business ideas at a high level (and in relation to me) is good, but there needs to be a line in the sand.
How will my personal board work?
Interactions: Most of the input will come in one-on-one sessions. And I’ll be sending out status updates just to keep me on track with my own goals.
Group meetings are an option, but I find most of them to be a goat rodeo. Occasionally, a dinner with folks could be a good way to get focused feedback, especially if there’s a presentation to share. But I would try to make it interesting (like wine tasting or perhaps an actual goat rodeo).
Compensation: Free meals, good karma and a lifetime of favors from me.
I’m just starting the process, but the people I’ve asked have been overwhelmingly supportive. We’ll see if it turns out to be a short-term need or a long-term lifeline. Either way, great meals with great people are not a bad thing.
Loneliness can be a tough thing for entrepreneurs, even after the company becomes an 800lb gorilla (with or without spraypaint). Having people there for you seems like the best way to end up on the right side of the river.
The 90 Days are up. Today is my deadline for choosing the next big thing, so here’s a quick update since I’ve received so many cards and letters about how I’m doing (read: 3 emails and a concerned looking cat). As per my last post, I haven’t found an existing company I want to join full-time. So I am officially starting my own.
Feels good to say.
I write this as I’m baking a chocolate cake for my daughter, so in person it doesn’t have the same gravity, but yes, in the next week I’ll be setting up shop in San Francisco and slowly rebuilding my love / hate / overdose relationship with caffeine.
Those who know me could have seen this coming months ago. I’m slow on the uptake.
But I am fired up. I want to win again. As these posts have ruminated on, the motivations are less about competence (proving myself) and more about significance (mattering), but it’s there. Now I just need great people.
Thanks for all your support.
It’s been a long search for a new gig. And at this point, after a metric ton of coffee and 472 opportunities to perfect my pitch on what I’ve been up to, I have found very little that has fired me up enough to want to join. Saying I’m “frustrated” barely scratches the surface. So I’ve been mulling the option of starting a company from scratch.
You wouldn’t think it would be a big deal. I’ve done it before, and I’ve had success, as have lots of my friends and colleagues. It’s not like I’m aiming for a drug-free Tour de France victory. But the demons keep yelling at me: You’ll lose track of your family. You’re too old. It’s too much work. It’s not interesting. You’ve done it already.
Anyone who has struggled to pursue challenge because they know it’s the right thing, even if they don’t have to, will recognize the dilemma. It’s like wanting to write a novel, and just staring at a piece of paper in front of you.
Lately my life has been a 12-round cage match with those demons. As my self-imposed deadline for a new gig inches closer every day, I thought I’d save others some trouble and share what I’m learning about taking big leaps.
1. Know why the fear is there
The biggest risk we all face, and the biggest tragedy, is a life unlived – one that fails to reach its potential. Joseph Campbell describes this in The Hero with a Thousand Faces as the tragedy of a hero refusing the “call to adventure” and staying home instead:
“Often … we encounter the dull case of the call unanswered; for it is always possible to turn the ear to other interests. Refusal of the summons converts the adventure into its negative. Walled in boredom, hard work, or ‘culture,’ the subject loses the power of significant affirmative action and becomes a victim.”
Or as Westley from The Princess Bride says, “Life is pain, Highness. Anyone who says differently is selling something.”
Humans weren’t meant for a life of comfort. It’s the worst plague on our first-world society – the reason we’re a depressed, overweight, over-medicated culture. We’ve lost our purpose. We’re built for walking 10 miles a day to track a small amount of food, and we use that body and mind to get drive-thru on our way home to binge-view Game of Thrones.
Fear should be one of the meters on our dashboard that we’re heading in the right direction in life. If it’s below a certain level, we aren’t living fully. Too high, and life will overwhelm you. But in the right amounts, fear guides us towards what we need. That’s why Eleanor Roosevelt’s “Do something every day that scares you” has become such a rallying cry for modern society. Some part of us wants to be in Game of Thrones. But all the base needs are taken care of, so we must manufacture situations to freak ourselves out.
2. Understand your fears
There are two types of fears that emerge when leaving one path to do something entrepreneurial: fear of doing it, and fear of not doing it.
The fear of doing it is a fear of failure, loss of money, damage to your reputation or image, and a general concern that the process will suck.
The fear of not doing it is potentially much worse, though we may not recognize it at first. Here’s a snapshot of what I see as the entrepreneurial “Fear Spectrum” (sounds like a canceled Fox reality show), ranked from least evolved to most.
Understanding where you fall on this spectrum can help you get a grip on your motivations, and how to harness them. For me, financial success and reputation were my main motivators early in my career. Later, my deepest fear became a life gone by where I wasn’t true to myself, one that didn’t match up to my potential or leave the legacy I had envisioned.
It’s possible to over-invest in a specific, fixed narrative for our lives, which are by nature in constant flux. When the story plays out differently than expected, it can create stress, unhappiness and an inability to be “in the moment” (the deep desire of choice for all of us over-stimulated wannabe spiritual types). That’s why being true to yourself (and not just your legacy) is the final stage of the model.
3. Draw courage from the people you love
If your decision lies within you and you alone, it can fester and result in paralysis. But share it with other people who matter to you, and suddenly you’ve replaced your 89-octane Camry-gas with liquid hydrogen.
In a previous post I mentioned Plato’s Symposium, an ancient philosophical text on the nature of love and desire. One of the characters, Phaedrus, says love is the greatest guide to virtue and courage. By way of example, he describes how soldiers in battle aren’t lacking fear, but rather they do not want to be shamed in front of the comrades they love. The more love, the stronger their ability to get past their fear.
Plato’s idea is succinctly rephrased in the 1943 US Army Officers Guide:
“Physical courage is little more than the ability to control the physical fear which all normal men have, and cowardice does not consist in being afraid but in giving way to fear. What, then, keeps the soldier from giving way to fear? The answer is simply– his desire to retain the good opinion of his friends and associates…his pride smothers his fear.”
Marcus Luttrell, the real-life Navy SEAL protagonist from the movie Lone Survivor, says the same thing: he wasn’t afraid of dying, he was afraid of letting down his “brothers.”
Like most challenges in life, finding the courage to make big moves in our lives relies on purpose and love.
As for me, it’s become clear my biggest barrier is that I haven’t brought anyone “into the boat” with me yet. My fear is 95 percent due to a lack of the right people. When there’s no one to be ashamed in front of in battle, we create our own characters in our minds and turn the shame on ourselves. (Watch too much Game of Thrones, and those characters might do some pretty twisted things to you.)
So this next phase is about doing an honest day’s work while finding the right people to join me in the journey. Maybe then I can have fun storming the castle.
Tis the season for come-back stories: It’s a Wonderful Life, A Christmas Carol, some new Sylvester Stallone vehicle. So as per holiday tradition, here’s my rumination on how to do better as a CEO/colleague/human the second time around.
Along my journey to find meaningful work, I struggled a lot with whether to work on a nonprofit. It seemed like the right thing to do, and I wanted to make a difference. I spent a chunk of time in the sector as a board member and volunteer, and worked diligently on learning about different causes.
But something didn’t feel right. Philanthropic work was meaningful, but felt a bit like playing a different sport than what I was used to in the for-profit world. And I wasn’t ready to give up on my game just yet, nor did I feel compelled to work on one specific cause above all else.
Still, I wanted to do some good in the world and create some kind of legacy that mattered. Would working on another company mean I was selfish? That I was failing to achieve my legacy? Was I a lesser person? Was there a way to make it all work in harmony?
So with the clock ticking on my continuing search, I made a decision: no matter which gig emerges on top, the money I make will be subject to tithing. My pledge:
51% of what I make from this venture will go towards a foundation to support children’s education.
Having been inspired by colleagues at Andreessen Horowitz, who pledged 50 percent of their earnings to charity, and Warren Buffett’s Giving Pledge (for people in the wealth stratosphere), this felt like the right path: I get to keep playing my favorite sport, and also get to help others if the company does well. My pledge became 51 percent because it’s in the majority. And my one-upper personality wanted to at least win on percentage, since they’ll destroy me on the actual amount.
51% of who-knows-what may be a small contribution in the scheme of things, but it feels right and hopefully has some ripple effect. As one of the characters says in Hot Tub Time Machine (a more recent second-chance movie): “One little change has a ripple effect, and it affects everything else. Like a butterfly floats its wings, and Tokyo explodes, or there’s a tsunami, in like, you know, somewhere.”
My mother taught me something about ripple effects. She was a long-time special education teacher whose passion, dedication and optimism were a huge source of inspiration. Often, she was the only one who didn’t give up on her students, and instead created the environment for them to become their best possible selves. One of my closest friends from high school who worked with her as a teacher said: “She would work with the toughest and roughest kids and give them a soft place to fall with no judgment. She would even feed the ones that didn’t get breakfast. She was worth 10 regular teachers.”
If any other second-time, venture-backed founders want to join me with the same pledge, regardless of the cause you support, I’ve already bought the domain 51Club.org. Raise your hand, and we’ll get our own handshake and hats. And maybe give those fancy-pants Giving Pledge people a run for their billions in softball.
The purpose of this blog is not to brag or fish for compliments from readers (but you know, if you really want to say something…) I am merely sharing the details of my own journey because your engagement helps me hold myself accountable – and perhaps the ramblings can be helpful to others along the way.
I’m thankful that we live in a time when giving is becoming a bigger and more common part of the conversation and financial equation. The greedy and self-preserving tone set by early American entrepreneurs like J. Paul Getty who said, “If you can actually count your money, then you’re not a rich man,” seems to be drawing to a close.
I’m more drawn to Churchill who said, “We make a living by what we get, but we make a life by what we give.” Here’s hoping this second chance is a lot more givey than Getty.
Have you ever watched a friend or former colleague lose their mojo in their work? Their fire and brimstone replaced with dull malaise. Their struggle to summon the energy just to talk about their company. It’s like a deflated clown balloon – there’s still a smile, but it’s sad and misshapen.
After witnessing this condition a lot lately, and having fallen victim to malaise in my own life, I started thinking about how to protect against it. Whatever I do next I want to create a culture of meaning, where people can stay challenged, alive and on their game – avoiding the death march of working with people they don’t trust or like, on a problem they can’t stand.
And I think you can do it without burning people out. I’m no longer in my selfish 20’s with nothing but time on my hands, so the challenge is to create a place where people are on fire, but can still maintain close relationships with friends and families and achieve equal or better financial success (except for any employees in their 20’s – they should be pulling all-nighters).
While many people will dismiss this thinking as the ramblings of a sun-burned ex-CEO too long out of the chair, I’m convinced there is a path that is both authentic and practical for achieving the proverbial “marathon, not a sprint.” Something between naive, feel-good HR sound bites and salty business advice with no magic.
The underlying question: Is great work culture solely a by-product of unbridled success, or does success come from great culture? Is it possible to see a return on investment (ROI) from investing in collective meaning that pays dividends throughout the life of the organization?
In pursuit of this work culture nirvana, I came up with the following personal tenets for my next gig. Taken individually, most of these points are about as original as an NBC sitcom plot, but together, they serve an important role in defining my next organization.
Start with Purpose. Even if you’re not curing cancer, find a way to connect day-to-day activities to improving lives and helping people. Ensure colleagues understand the larger, human story behind what they’re doing. Great companies not only help the world, but provide a context in which the employees can become great in the process.
Win. Pizza Fridays and foosball tables are useless if you’re not beating goals and winning. Too many companies are busy looking inwardly to understand their “culture” instead of focusing on the biggest contributor to that culture: success.
Money Follows, Never Leads. Stay away from people driven primarily by money. I don’t want colleagues looking for “a job,” nor does anyone want to be part of a company run by bloated egomaniacs looking to buy their third Ferrari.
Openness. As you can probably tell from this blog, I don’t just “open the kimono.” I burn it and run naked and screaming through town. While there is a small percentage of information you just can’t share, being open and honest about the rest of it builds trust and forms a tight culture.
Teamyness. Ensure people feel connected and fired up, and that they’re supporting each other. Monitor. Hire diverse people, but ensure their values match up with the company’s, and be quick to kick out those who don’t further these goals (something like Willy Wonka’s golden egg machine for employees).
Make ‘em Feel Wanted. At their core, people want to be accepted and valued for who they are. Celebrate the uniqueness of each person, even if that uniqueness includes stuffing their office with Charles in Charge posters.
Celebrate Success: Some of my best memories are from victory celebrations. It’s rare in life to have those home-run moments after high school. Find ways to give people the chills because of what they’ve pulled off.
Give Back. Connect work life back to the community as a whole (stay tuned for an upcoming blog on this one).
This pledge is easier to pull off in the early days when you still have a small, collaborative team. It gets much harder as a company is successful and scales. All the more reason it needs to be part of the fabric (values, mission, goals, tools, conversations) of the business from day one.
Ironically, in thinking through this problem, it dawned on me that helping those superstars who have lost their mojo is a source of meaning for me. Like Holden Caulfield’s eponymous metaphor where he wants to be a “catcher in the rye” to save children from the pain of adulthood, I find myself wanting to help people avoid a meaningless existence in the workplace and create the context for them to come alive again. I guess that’s the air in my clown balloon.