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 Will.i.am 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!

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13 thoughts on “Wine, Women and Why We (Should) Start Companies

  1. You ask a good question about where entrepreneurial inspiration comes from and how to realize it. Too often the answer to these questions miss their mark because it is too hard to answer effectively without precision and the answer becomes mired in emotion, which is hardly replicable for another person let alone a guide path for the entrepreneur themselves.

    Despite this limitation I will attempt an honest and concise response. While I work for the Federal government my current position has a huge range of freedom to try to figure out the future of news in international markets. Part of my guide on where to direct my team is based on the hard empiricism of research…their is an unfolding of evolution of media and technology, though oftentimes following a particular path in a different culture. There are also the requests of our own journalists (e.g. Voice of America) and how they would like to tell stories in the future.

    However, there is enough room between these guide posts to pursue more self-directed interest. And in that area there are three motivations that I have observed about myself that push me forward, usually in good directions: 1) would this idea or project be fun? Would it make the team excited about solving? Would it challenge us, but we can articulate what we think a good end state, no matter how fuzzy? (Intangible!) 2) Would people I/we admire be impressed by our (or any) solution? Would we attract the smartest people in the room to be interested in our work? (Crowd-based, but again intangible!) And 3) would it be something that contributes value – for me mainly social in a career of nonprofit/public service – to someone or group that would appreciate the opportunity to accelerate the improvement of their community. (Intangible again!)

    So an honest assessment for me is that what drives me is more just a feeling – the itch or tingle of this is going to be awesome – than a rational thought…and to be honest that is the way I think it works best. (Cross posted from FB)

    1. Very thoughtful response, Rob. Love it. This was a tricky one for me to write because I, like you, gravitate towards motivation in the traditional sense, but the symposium is about Platonic Love / Desire. I may be drawn to something for the same reasons as you (mostly intangible), but what is the purpose of my being drawn to it? If I am as enlightened as possible, what’s the ultimate reason why I should do it? We are drawn to procreate because it’s baked into our DNA (different “itch or tingle”). But it’s different to think about having children with someone you love as the most fulfilling purpose behind it.

  2. I don’t think there is a single answer for this. Entrepreneurs, like the rest of us, are driven by different things: their parents, their surroundings, their experience, money, power, etc. I don’t think there is a single motivation to do it.

    Your question about why you should do something leads me to think of something I’ve called the death-bed calculation. Regardless of what you think happens when you die, I believe (unless you are hit by a bus unexpectedly) you will self-reflect in a manner deeper than you ever have. You will ask yourself a question – every person may have a different one. It may be “Was I a good person?” or “Did I leave the world in a better place?” or “Did I live life to the fullest?” Regardless of what it is, I find that when I ask people after a couple of drinks what they will ask themselves at this moment, I tap into their true motivations. Just a thought….

  3. first of all, you can’t tease us with a mars adventure notably “illustrated” by Dave Hersh, and not post the illustrations! And you’ve given me a new understanding of Platonic love. I also appreciate the parenthetical reality alerts. I might want to work a few of those into my daily discourse (verbosity alert).

    1. i, too, eagerly await publication of dave’s illustrated mars adventure! imagination meets desire meets artistic expression (curiosity alert).

  4. Hi David, we are mutual friends with Angie, who sent me a link to your post.

    Thank you for your very thoughtful response to being Entrepreneur. I am an Entrepreneur and am with you on surrounding oneself with like minded people (which I am doing at the moment), but I also have this strange need to be with those who are opposite (normal, mainstream, conservative) and make me feel uncomfortable. This is partially because I wear my “weird” on my shoulder and demand that more people in mainstream find a place in their heart for different, but also because I want my thinking challenged. Either way, it is ultimately selfish; I am fulfilling a need I have.

    To your point, I think Entrepreneurs start things for the same reason that we want to have babies: Selfishness. Lately, I have been challenging people wanting to “have kids” by simply asking “why?” Answers are always (thus far) about them and not about the other (child).

    “I want a junior. Wouldn’t that be cool?”

    “I am lonely and feel unfulfilled.”

    “I want to further life and my legacy.”

    “My kids will change the world.”

    I, I, Me, Me…

    So my response normally is: “It is the most selfish thing that Humans do, isn’t it?”

    Answers vary and sometimes I get get kicked out of parties, but no one argues with “How do you know it is what Junior wants?” They don’t and can’t.

    So to me Entrepreneurs do their thing because they cannot help themselves, really. They are selfish with their idea and absolutely must birth it to the world against all odds (most fail). Much damage normally occurs in the process, both personally and on others, and it very much resembles giving birth (there is a lot of blood spilled).

    That said, we have to be selfish to move the world forward; We could use a LOT more Entrepreneurs.

    The most wonderful thing about being Entrepreneur is that one has an unwritten obligation to reach back and help another inspired, change the world, self-centered, risk taker fail forward and keep getting up. Whether the Entrepreneur succeeds or fails, their redemption for selfishness is to share wisdom and be a Mensch for others going down a path of uncertainty.

    PS – Went along for the ride of being selfish… I have three wonderful kiddos. I love them far more than any thing I started on the biz/org side. Delighted to think that one or all of them might also be Entrepreneur (again about me). I most certainly will challenge them either way on “why” they want to have kids (if any of them do).

  5. Great post, Dave. It’s complex but I imagine an entrepreneur’s motivations can be an insightful indicator into their actions (and vice versa).

    It’s really interesting to talk to entrepreneurs and hear what motivates them. There are product people, engineering people, money people, marketing people, opportunity people, personal freedom people…

    I find myself aligned with the product side most often, just following my desire to create something. Providing a product or service and seeing it used to enrich peoples’ lives. But now you’ve got me thinking it could be far more complicated than that.

    My entire family are entrepreneurs, it could be that I just seek the lifestyle I was raised around.

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