Stressed to Impress: Don’t Get Derailed by Insecurity

Originally posted on FounderDating


I couldn’t sleep a wink. I was pissed. It was ten years ago. I was the Founding CEO of my last company (Jive Software) and was attending one of the many navel-gazing, Insertbuzzword 2.0 industry conferences.

That day, I talked to a “friend” who was the CEO of a company in a related space. With all the subtlety of a Sicilian stuck in traffic, he let on that his company was going to do in sales that year. And it was twice what we were going to do. I couldn’t believe it. I had worked so hard to crank out our revenue engine. And now we were getting passed. I couldn’t let it go. I decided to get hyper-focused on tripling our sales number for the next year and surpassing that Tool and his company.

Problem was, the whole idea of comparing myself to some adjacent company was ridiculous. Never mind that we had just moved the company from New York to Portland, hired a brand new team and bootstrapped the whole thing. I felt like I was losing a race in my mind, and I obsessed about it. Which was ridiculous. I might as well have been losing sleep over the Bennifer breakup (this was 2004 mind you).

Looking back on that period, it seems obvious: There’s nothing wrong at all with being passionate and focused on the next mountain to climb. The problem for me (and I suspect many first-timers) is that underneath that obsessive focus is intense insecurity that clouds judgment.

dog with frisbee quote


In the early days the misguided motivation was wanting to hire superstars. Then it was big sales numbers. Then it was raising capital from a top firm. More growth, board members, positioning for an acquisition, IPO, blah, blah. Anything impressive.

By themselves, these big goals are not really a problem. But if the outcomes you seek come from an insecure place of wanting to seen and be impressive, you either a) focus on the wrong goals, or b) neglect the work that best supports those desired results for those outcomes themselves.

Some examples of how the insecurity derailed me along the way:

  1. I took shortcuts to the goals. For instance, hiring people to do big deals but who, in my gut, I knew weren’t a cultural fit (and who ultimately blew up).
  2. I made it difficult for employees to confide in me because I had a hard time hearing anything but progress.
  3. I had a hard time enjoying the ride. You always feel like a better life is right around the corner, after you hit your goal, which is never the case. If you don’t hit it, you get deflated and feel like you’ve lost. And if you do, you realize it hasn’t changed things much and you sit in a vacuum while you find something else to take its place.

I see this insecurity in a lot of first-time entrepreneurs who want to prove themselves. Not only in their bragging about investors and customers, but even the way they think about the business. Like putting an “Exit Strategy” slide on a pitch deck. Seems innocuous, but what it often says is that the entrepreneur is unnaturally focusing on the outcome, likely because they equate it with their own worth as an entrepreneur. The reality of “exits” is that opportunities will abound if you build a great company, but focusing on the exit is the tail wagging the elephant. And it’s only going to cause you and your company pain along the way.


This time around as a startup CEO, I’m trying to save myself the pain. Knowing where you’re going and having Big Hairy Audacious Goals is important, but checking your ego and building out systems and processes form the basis for greatness. Focusing on things like:

  1. Doing amazing work every day. “Leaving it on the field”.
  2. Building out the infrastructure to keep your customers thrilled and your employees thriving.
  3. Becoming a true servant leader who is “cloaked” in the needs of the business.
  4. Thinking about process and system goals more than your big company goals, and celebrating those successes along the way.

Thanks to a little help from friends and colleagues back in 2004, I ultimately realized that trying to triple sales to one-up another company was not the move of a stable leader. Over the next few years, we built out a pretty rugged framework for business planning that put the needs of the business and the process goals up front. If we got all the that stuff right, sales would follow.

Usually people who preach to me about being “in the present” and “the journey not the destination” make me want to punch them. Especially non-entrepreneurs. But I’m chilling out in my “over 40” years, and now realize there’s some truth in that overused maxim: fully immersing yourself in the work itself, separating your ego from the equation and focusing on systems and process goals ultimately leads to better outcomes…and a healthier relationship with your company. You know, more like Ben and Jen.

Hot Tub Tithe Machine: Pledging Half of What I Make

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.

He picked up the ball and ran

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 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.

Happy holidays.

Catcher in the ROI: Bringing Back Workplace Mojo

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.

prison yard - Version 2

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.

  1. 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.

  2. 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.

  3. 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.

  4. 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.

  5. 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).

  6. 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.

  7. 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.

  8. 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.

From Paralysis to Purpose in 90 Days

Recently, I challenged myself to commit to a gig by February 1 (see timer courtesy of Crushpath). My readers sent a lot of great feedback, questions…and a few very concerned head shakes. Some wanted to understand how I’m narrowing and filtering the options so that I’d be sure my next step was the right one. So with full-warning that this post is a bit of a selfie, here’s a snapshot of my process.

Getting to Know the Older Guy

Prior to starting the 90-day timer, I spent some time on what gets me up in the morning. Earlier in life, motivations were pretty straightforward (beer, money, opposite sex, beer), but with age, they’ve become more complicated. After seeing a pattern of ex-execs jump at the next “shiny metal object” job that came their way, I decided to dig deeper in the hopes of avoiding the wrong thing.

In a society infatuated with the self, there’s no shortage of tools designed to help people understand what makes them tick: Enneagram (I’m a 3), Myers-Briggs (ENTP), What Color is Your Parachute (mauve). I was even given a set of purpose cards (worst poker game ever). You could get caught up running self-diagnostics for months, but I think it’s best to pick one or two frameworks that fit your personality. Ultimately I found the most insights by asking myself: 1) When do you feel the most alive and why? 2) What do you want your legacy to be? 3) Who do you “want in the boat” with you?

I’ll spare you the navel-gazing details, but what I learned was this: I’m at my best when leading a team of creative GNAKs (good-natured ass kickers) on an entrepreneurial mission where new technology can make a huge difference in people’s lives.

Clarifying and Learning

Once I had a sense of the goal, the process for attaining it seemed less Herculean. I listed out my “Must Haves” (e.g. creative control, dinner w/ family 4 out of 5 weekdays, intellectual interest) and “Can’t Haves” (e.g. long commute, board members who think they know best, overly crowded market).

I interviewed people with similar early careers, but different paths afterwards. People who had been founding CEOs, but had gone on to become venture capitalists, exec coaches, serial entrepreneurs, social entrepreneurs, nonprofit founders, whiskey-shillers, ranchers and confidence men (last one made up). I looked for people who shared my values and passions, and learned everything I could. Then I listed the most appealing options.

Extreme Narrowing

With list in hand, I jumped into a professional dating period that rivaled Warren Beatty in the 70’s. Lots of good people and ideas, but in Silicon Valley everyone wants to be CEO of their own thing. Also, it’s hard to commit to people you haven’t worked with before – and difficult to get two strangers excited about pursuing the same goals.

Realizing the process was taking too long and going in weird directions, I set the timer and committed to focus. Since then, I have become shark-like in my priorities. No meetings that don’t advance the goal. Always aware of my daily tasks. I even set up a war room in my office for managing priorities and scheduling.

War Room from Dr. Strangelove

War Room from Dr. Strangelove

Since then, I’ve only focused on options that get me excited. These could include starting something from scratch (company, social venture, nonprofit, fund), becoming “Founding CEO” for an early-stage start up, and even taking a shorter term executive role to help companies get to the next level (selling the company, raising a round, etc.).

I’m giving each opportunity a rank of 1-5 in three categories: Gut (do I just want to go do it?), Heart (am I emotionally drawn to it?) and Head (does it make sense to do it?).





Next Action


Sample Gig 1




Conversation with Phil K.

In-person working session

Sample Gig 2




Talk to EIRs

Sample Gig 3




Dinner with Veronica and Tom

Facilitating a meeting would be good path

Sample Gig 4




Need feedback from Steve

Option for shorter term work?

Crab Fishing




Rent boat. Sit in it.

For each line item, I drive hard to a decision. If the opportunity remains interesting to me, I’ll take whatever next steps are required to learn more to bring me closer to a decision.

The best filter I’ve found is to work directly with the team involved. There’s no better way to get to know the opportunity than rolling up your sleeves on something together. This is especially true for new careers – if you’re a mailman and want to be a hand model, best to try it out first.

Final Thoughts

I found it helpful to take time away from all the voices. Too much advice can cloud judgment, and often the advice is what those people would do in your situation, not thoughtful insights into your unique path. (But please keep your comments coming – I’m totally listening.) As a culture, we get so wrapped up in what other people think, it can be hard to find purposeful work. We put too much emphasis on personal brand and image over happiness. It’s a shame. Most people are too busy taking their own selfies to care anyway.

You can be as structured about this process as you want, but my experience is that the gut knows best. The more closely I listen to it, the better the options become.

Forcing Function: 90 Days to a Decision

As mentioned previously, it has taken a long time to settle on my next full-time role. Following a period of professional experimentation that turned into full-blown commitment phobia, I have finally given myself a firm deadline: 90 days.

While these past nearly four (!) years since I left my last CEO position have brought the kind of freedom I once dreamed about, I’ve also learned that the risk of paralysis between projects is real and dangerous. With no forcing function to choose a next step, I was guilty of over-analyzing all options and comparing each of them to previous gigs.

No longer the broke, hungry young entrepreneur, I now live in beautiful Marin county, surrounded by soccer games and middle-aged triathletes. I’ve had a whole football team of people to support the navel-gazing lifestyle: therapist, trainer, yoga instructor, life coach, chef (trust me, it goes on in even more embarrassing directions). I had become one of the lotus-eaters from Homer’s Odyssey.

Now whosoever of them did eat the honey-sweet fruit of the lotus, had no more wish to bring tidings nor to come back, but there he chose to abide with the lotus-eating men, ever feeding on the lotus and forgetful of his homeward way.

While some of my guy friends tell me I’m suffering from a severe case of “affluenza,” I’d argue that my problem is not about money, but too much comfort. I had the same issue when I had a “comfortable” job early in my career. The underlying question is: how do you break out of crippling patterns of ease and security. Where does the catalyst come from? I could go on forever in the beautiful ether with no grounding, but would end up medicated in one way or another, possibly becoming the Hunter S. Thompson of greater Marin.

I thought I had checked the box on success and was on to other bucket list items (“Invent next turducken” still not complete), but slowly became miserable. I was at home more often, but less happy when I was there. Outside of family, purpose was fuzzy (no “homeward way”) and I was trapped in the American Dream, filling in life’s gaps with empty-calorie activities.

2013-10-26 11.49.35

And I wasn’t paying enough attention to life’s bank statement to see the shrinking balance. As Seneca said:

“It is not that we have so little time but that we lose so much. … The life we receive is not short but we make it so; we are not ill provided but use what we have wastefully.”

Pity is the last thing I expect. I’m not that self-absorbed. Instead, I’m hoping you’ll help hold me accountable to my time frame and my goals.

I’ve only been “on the clock” for a week, but so far, so good. (“Bought whiteboard: check, Publish blog: check, Have second thoughts about arbitrary timeline idea: check.”)

Reservations aside, I’m awake, purposeful and have numerous interesting conversations going. Instead of considering all options, I am forcing myself to whittle down the list aggressively – make choices, stick with them and figure out what matters most.

I want to get back at it. I miss the fight, the blood and sweat. Climbing a mountain with a tribe. The burning desire to build something is still in me at 41, and I can’t meditate my way past it. And frankly, I don’t want to.

Taverns over Yapshops: How Good Conversation = Business Lubrication

When I first entered the workforce as a young management consultant in 1994, I was a terrible listener. The whole point of being a consultant is to be a good listener. Ergo, I was not good. I gave it a valiant effort, but spent so much energy trying to find ways to appear smart with what I said (and the fancy glasses I wore), that many times I would miss the point of what people were telling me.

Years later, after I became CEO, my listening skills improved dramatically. (Although I would focus so intently while listening that I freaked people out with my stare. “It feels like he’s trying to stare into my soul” read one 360-degree review.) But much of my energy went into “must have all the answers” with a heaping side of “must accomplish my goals.” I was open and honest, and would listen politely, but eventually I would steamroll my own agenda after the requisite polite waiting period.

The way I see it, good conversation is the WD-40 of successful businesses – the lubrication that leads to growth, culture and success. (I figure using “lubrication” a few times will help my site traffic.) Nothing happens without good conversation. And by conversation, I don’t mean light-hearted chat; I mean, the important debate, dialogue and exchanges that drive things forward.

Being so agenda-driven, I missed a lot of good ideas because I either didn’t respect people, didn’t take time to truly listen, or because my conversational counterparts were less forceful with their messages. People might have appreciated the quick decisions I was making, but those should come after vigorous debate, not squashing ideas along the way.

Whatever I do next, I’m looking forward to learning from past mistakes and don’t want the same habits to follow me. As part of this growth, I’ve been drawn again to an essay I last read in my 20s. Michel de Montaigne was a thinker and statesman during the French Renaissance who is credited with inventing the modern essay. (You can thank him for those late nights in college.) He came from an era when people had time to consider these things without having their attention machine-gunned by status updates. When he turned 38, he locked himself away in a library and wrote about life lessons and insights using a short-form, personal, subjective style that no one had used before. It was eventually called the essay. He was basically the original blogger. That’s him on the cover below looking like a driftwood sculptor from Santa Cruz.

Montaigne’s essay is translated to English as the “art of conversation,” but it’s much more than that. What this guy from the Renaissance knew that most modern leaders are clueless about is how to handle the exchange of ideas effectively and gracefully. Read the whole thing to bulk up on your conversational abilities, not to mention reacquainting yourself with terms like “seedbed” and “fishwife.” Or, if you’re short on time, below are a list of nuggets I found worth posting on the wall:

1. No proposition astounds me, no belief offends me, however much opposed it may be to my own.

Montaigne instructs us to move toward those who contradict us, as that is what leads to learning and truth. We don’t want to surround ourselves with a bunch of sycophants (“a bland and harmful pleasure to have people who admire and defer to us,” he says), but people who will constantly challenge our opinions. This sounds like obvious advice, but founders often suffer from the need to be the smartest in the room and, at least subconsciously, get misguided pleasure from having people kowtow to their ideas. As Montaigne points out, the enlightened leader finds more pleasure in having his or her mind changed by a strong conversational opponent rather than by winning a battle over a doormat.

2. I can go on peacefully arguing all day if the debate is conducted with due order.

Having a good process for debate makes it a thoroughly satisfying and productive activity, and allows the best outcome to emerge. When done well, it does not matter where ideas come from, but that the right outcome is achieved. If done poorly, defensiveness spins out of control, and people will cling to their ideas like a life raft.

Most entrepreneurs are skeptical of authority and ruggedly pursue our own path in the world. As a kid, I was kicked out of classrooms, baseball games and camps. I even got kicked out of tennis matches when I was a ballboy. I couldn’t accept that there were people who could control my fate. This gave me drive, but also gave me a ton of baggage in the boardroom when it came to pushing my ideas through.

To combat these issues, I had to set up core values for the company like “seek first to understand, then be understood,” and repeat mantras in my head to control my defensiveness and avoid imagining people disintegrating a la Star Trek. Mantras like: “Don’t take it personally,” “Repeat back what they said so they know you understand,” and “Don’t imagine people disintegrating.”

3. Better to learn to talk in a tavern than our university yapshops.

In this passage, Montaigne takes on academics who wax on at length using flowery language, but have no life experience to back it up. They can repeat Aristotle verbatim, but don’t have true understanding and hide behind their big, flowery words. The takeaway here is to shed buzzwords, speak truthfully and admit when you don’t know something.

I was not immune to the allure of jargon. It sneaks up on you, and before you know it you’re a “disruptive, gamified cloud-marketiled (made up) destination for mobile users.” Keep language simple, but real. Truth wins out, and builds more respect from your colleagues.

And how awesome is “yapshop”?

4. The gravity, academic robes and rank of the one who is speaking often lend credence to arguments which are vain and silly.

 I recently advised a CEO who had spent nine months working with a Sales VP recommended by the company’s lead investor. The CEO—awed by the lead investor’s status—failed to act on initial concerns that the VP was a bad fit. The result was disastrous for the company. The VP ran with a playbook that wasn’t right for the category and caused the startup to lose early customers and not gain new ones. Just because someone was successful in their prior career doesn’t mean they necessarily know what’s best for your business. Listen, consider and take the best path forward.

Side note from my consulting days: also beware of English accents. My smooth-talking English colleagues could persuade a pharma company to enter the sock-darning business before they realized what was going on.

5. Most people are rich with other’s abilities.

Or, as Stewie on Family Guy once said: “(My Myspace page has) my favorite songs and movies and things that other people have created but that I use to express my individualism.”

The business world is full of people who regurgitate what they’ve read online or hear at conferences, but don’t have the experience to back up. You may have heard these gems: “You must give away something for free to get customers.” “Retail is completely dead.” “No one would rent out their own house for a night to someone they didn’t know.”  Following these platitudes can lead to a lemming-like approach to business-building and often incorrect assumptions about markets and business models.

Challenge those who speak blindly in universals and avoid the tendency when you see it in yourself. Question why, and dig deeper.

To recap, Montaigne reminds me of a few things I need to be reminded of constantly:

Work with smart, engaging people.

Make it easy for them to question you.

Manage your ego.

Don’t get offended.

Seek truth, not status.

Question everything.

Also, he pushes us to have a good time – laugh when others make fun of your shortcomings, and encourage your team to poke fun at each other during the process. We don’t give enough thanks to the Renaissance for birthing smack-talking. Almost makes up for the invention of the essay.

Wine, Women and Why We (Should) Start Companies

It’s been 3 years, 8 months and 3 days since I stepped down as CEO of Jive to decompress, fix the mess at home and figure out my next move. I’ve kept myself respectably “40 hours” busy on many projects, but have had an annoyingly tough time deciding on my next full-time pursuit. In countless conversations about potential opportunities, most of the ideas have been as exciting to me as working on my taxes while standing in line at the DMV.

I keep getting wrapped around the axle on my real desire for doing it: is that really how I want to spend my life?

During my time at Jive, I spent more time considering which brand of conditioner to use than delving into my deeper motivations and desires. Like a lot of first-timers, I wanted to “build something great,” “change the world” and “lead an awesome team,” but the reality was that it was exciting, new and (at least half the time) working. That was more than enough.

And let’s be honest: as much as I talked about how money wasn’t the motivation, it certainly wasn’t absent from the equation. My Mom recently sent me a story I wrote when I was nine in which the main plot was how I was paid $20 million a week to live on Mars for a month. Not much happened other than me living on the planet and then getting paid. Clearly money was an early obsession of mine, along with including my name as many times as possible (below). But I knew intellectually it shouldn’t be.

Screen Shot 2013-10-16 at 6.21.55 AM

Cover to My Mars Story

For something that takes up half to two-thirds of our waking lives, shouldn’t we be crystal clear about why we’re doing it? And more importantly, why should we be doing it?

Enter an unexpected source of guidance: Plato. (It should be noted that I got a C- in my freshman philosophy class. But my Dad is a retired philosophy professor who spent much of my childhood using Hegel and Kant to help me think through issues like football and college, so something stuck.)

Around 385 B.C., Plato created what many call his masterwork: The Symposium. A “symposium” was a wine-fueled party where participants each give speeches on the same topic. At the end of the evening, one less slurry and more brilliant speaker is declared the winner (it pays to get the early speaking slot).

Plato was not at this particular party, which took place in Athens many years prior, but that didn’t stop him from presenting the arguments in dialogue form to make his case on the ultimate purpose of desire. Each historic figure presents appealing arguments and adds to the book’s overall theory–even the guy who can’t stop hiccupping (really).

At the end of the evening, Socrates emerges as the winner. But in his speech, Socrates actually recounts a conversation with a priestess named Diotima, who gave him the essence of his argument. So while women aren’t even invited to the event, it’s still a woman who manages to make the most thoughtful case on the purpose of desire.

Diotima tells Socrates how the God named Eros (Desire) is the son of Resource and Poverty. This is a God who is always hungry but also tough and resourceful in making things happen; he’s always seeking, never truly finding. (Sound familiar?)

Diotima’s main point (spoiler alert) is that the purpose of desire, and what all humans seek at our deepest level, is to “be impregnated by ideas and give birth out of the pregnancy of the soul.” In other words, the same drive behind physical love (procreation and extension of the species, which are the closest we get to immortality) is even more powerful when applied to our intellectual lives.

Yes, this is a bizarre metaphor to bring up in a business blog, but stick with me. The idea here is that the purpose of our human endeavors should be to take in (be impregnated by) outside ideas, and then to give something beautiful back to the world through our own unique lens. To live a balanced intellectual life, we need to be both receivers and senders of ideas.

Unfortunately most entrepreneurs are much better at sending, not receiving. We want to be the smartest in the room. We have trouble listening. Left unchecked, this tendency will lead to an innovation-less company taking the path of least resistance. These people may make money, if that’s the goal, but they do not represent an authentic or original voice in the world. As the philosopher said, “Where is the Love?”

Steve Jobs (un-original alert) famously brought together technology and the humanities. He was remarkably open to being impregnated by outside ideas like calligraphy and furniture design, and using them to create beautiful products. He didn’t make “sugared water”.

I’m not proposing to be Steve Jobs (reality alert). But I found Plato’s thesis to be the “first ice cold beer on a hot day” of my confused life planning. If you step back and consider the purpose of entrepreneurial desire as being impregnated by ideas and giving birth to something good and beautiful out of your (and your colleagues’/company’s collective) soul, then it might open you up to a more satisfying experience and actually make the world a bit more interesting.

Re-reading this section of Plato empowered me to stop striving for perfection, but find inspiration instead from a broad range of perspectives, surround myself with like-minded people and give birth to new ideas (big, small and everything in between).

And it made me realize that hunger / poverty comes from many places. Being open to inspiration from unexpected sources leads to discovering hungers I didn’t know existed.

Think about all that the next time you refer to your company as your “baby.”

Where have you found motivation and inspiration for your biggest entrepreneurial moves? Do you feel like you have a good grip on why you’re doing what you do?

Would love to hear. Keep the great comments coming here, and through the social links below – thanks!

The Background: One Flew Over the Startup Nest

Ask any former startup founder about their darkest moment, and they’ll have it queued up faster than their elevator pitch. Mine was the summer of 2009.

The company I had helped start and build as CEO was on fire. We had gotten through the deep 2008 recession and were on track for a record year while being cash-flow positive. We had emerged as the leader of our category and were starting to talk IPO.

But my personal life was dying faster than a carnival goldfish. I was so engaged in surviving the recession and building a great company that I completely lost track of my then eight-year-old marriage. We were always the couple that people admired for being great communicators, but over that period, we had become more like building contractors who happened to be working on the same site.

As things began to unravel at home, I started to lose my grip at work as well. Friends and colleagues watched me transform from the “good-crazy” of an entrepreneur on a mission to “crazy-crazy”—the kind who refers to himself in the third person and stockpiles nickels in an underground bunker. I was lashing out at people for no reason and would leave meetings with no idea what we talked about. I was insane and stumped. Unsure who I was supposed to be and what my family or the company needed from me. And there was no roadmap out of it.

ImageWWI Bunker, Slovenia

While this was clearly one of the larger issues I faced as an entrepreneur, it was just one in a long list of “WTF am I supposed to do now?” moments. Things like “when should I analyze a problem versus go with my gut?” and “how do I show confidence while admitting I don’t know the answer?” Few friends or advisors were able to understand or help me get back on track. As I reflected on that time later, there were three areas where I needed help and couldn’t find it:

  1. How was I (and my role) supposed to evolve as the company grew?
  2. How do I deal with all the up and down feelings without losing confidence?
  3. What would a great entrepreneur do in this situation? What does greatness even mean?

Eventually, I figured out that some big thinkers have been tackling the core of these questions for thousands of years, and that answers could be found by focusing on being a good person, not just a good entrepreneur. But it’s hard to spend a day at the library reading Aristotle when you’re working seven days a week to build a business while also balancing / repairing personal relationships. I needed wisdom in a digestible form. Unfortunately there wasn’t much that was useful in the gaping space between Shakespeare and “10 Ways to Clean up your Inbox.”

Since that time, I have seen some amazing blogs emerge for startups and early-stage CEOs. These include Ben Horowitz and the rest of the partners I’ve had the pleasure of working with at Andreessen Horowitz, who have done an outstanding job providing insightful guidance, along with folks like Steve Blank and Fred Wilson. There is a much richer conversation now.

Still, a lot of the best bloggers for entrepreneurs offer strictly business advice or technical advice. Or, they are written by VC’s for VC-backed companies, which represent less than 1% of American startups (insert your own “we are the 99%” joke).

In short, there are a lot of lonely CEO’s out there, struggling with weighty issues and no context. There’s a pretty rich inner life flowing under the surface that most of us ignore more than the Homeland Security Color System in airports. But if we take time to dig into it a bit, we can set ourselves and our companies on a much more satisfying and successful path.

So this blog—and possibly a book at some point—is my shot at helping entrepreneurs, whether they run a coffee shop (I’ve owned one), a nonprofit (I hope to start one), a company that sells double-decker backyard grills (I want to know you) or a multinational software company (I’ve done that). I understand what you’re going through, and my goal is to share insights from big thinkers and real-life entrepreneurs on how to build a great company by being an authentic person–to kick ass by being good.

After that crappy summer of 2009 (worst Bryan Adams song), I moved our family to California from Portland, Oregon, to build out the company’s Palo Alto office and settle my family in a long-term location. The company was doing great, but keeping the life and work plates spinning was becoming increasingly hard. So in early 2010, I signaled to the board members that being a public company CEO was not in the cards. Having no one around who understood or could help, it was one of the hardest issues I faced, but the right outcome. Thankfully, my life got back on track, and my marriage is stronger than ever. And I’ve been able to work on interesting new stuff with folks at Crushpath, WildAid and Andreessen Horowitz.

Had I better understood the changes that I was (and should have been) going through as an entrepreneur, I might have avoided a lot of pain, and things may have turned out differently. But, as I once read, life can be like a vase that gets broken and then glued back together–the cracks are still there, but you’re stronger in the end.

More to come soon. All feedback welcome and appreciated.