Friday, January 7, 2011

Headlong into A Wall

I love the NPR (National Public Radio) show, This American Life. Each week, they pick a theme and then provide three or four radio stories on that theme. Iris and I will often listen to podcasts of it when we're traveling.

The other day as we drove to Connecticut, we listened to an episode entitled: Last Man Standing in which the team presented "stories about people who feel compelled to keep going, especially when everyone else has given up" and then asked "why?" Why is it that some people persist when others quit? Is it genius or stupidity? Vision or delusion? Insight or blindness?

In one story, a man named Duke Fightmaster decided that he would be the one to replace Conan O'Brien when NBC announced that Conan would be taking the place of Jay Leno on the Tonight Show. Although Duke had never done anything like hosting a late night television show, he "knew" he was the guy. How would he get the gig? Simple, he'd start by producing his own television talk show, build a following and then be discovered by those who would invariably see what a great talent he was.

So, with a single home-video camera, a makeshift studio in his bedroom, a small audience of friends and family and a single guest, he began. The show was cute, it was quirky, it was funny and everyone loved it. He was on his way.

Over time, Duke expanded his show both in duration and scope. He brought on writers and film crew. He moved from his bedroom studio to a local vetrans' hall. He quit his job and began living on his wife's "extra" income from teaching Yoga, family savings and credit cards.

Over the course of a couple of years, people came and went, he maxed out his credit cards, lost his house and finally declared bankruptcy. He was in deep debt. He'd lost friends. But he was certain that if he just held on a bit longer, it'd all be worth it.

When he finally stopped producing the show, he viewed it as "just a temporary setback", still holding onto his dream that he could indeed replace Conan O'Brien. Through the losses of capital, possessions and friendships, through panic attacks and deep emotional challenges, he persisted, never giving up, running headlong into... into what? A brick wall or the illusion of one? Was he inspired or insane? Was his seeing what others do not see vision or was it delusion? How can you tell?

As Spinal Tap bandmate Nigel Tufnel commented to David St. Hubbins regarding his first glimpse of the all black cover of their long-awaited lasted album, "It's a fine line between stupid and clever." And you have to wonder: where exactly is that line? Is it fixed or is it variable? Does it change from person to person? How do you know on which side of it you stand? Can the sides suddenly change on you without warning or announcement? If they do, how do you know which side you're on afterwards?

When I decided to found an Internet security company and raise venture capital to fund it, I received all sorts of advice, much of which came from people who weren't always clear as to the side of that line on which they thought I stood. I had a really great job that paid quite well, kids in high school, equity in the company where I worked and a big mortgage. And yet, I decided to quit my job and, cash out early (rather than allowing the equity to mature), and start working full-time on my business plan and business.

By the time I finally did get funded, I'd burned through my savings and racked up tens of thousands of dollars in credit card debt to pay people and purchase equipment. I'd recruited a core team of marketing, product and technology people and had been rolling along as though getting funded were simply something that would happen at the appropriate time, kind of like planning for a vacation in June. It's not there yet, but that's because I planned it for June. The possibility that I might not get funded never even occurred to me.

Along the way, there were people who thought I was crazy to have left such a great position and others who were cheering me on. Surprisingly, my dad who had always been quite conservative in regard to jobs and money, and who'd spent his entire career working for one company, called me to tell me that he was really proud of me and that he'd always wished he'd done something like I was doing.

Nonetheless, even when I did secure angel-funding of $2.5 million, there were those who warned that I needed to be more picky in regard to the funding source. It wasn't enough to have money from a private investment fund; you needed to find so-called "smart" money from industry insiders.

When I decided to take the funding, several of my friends who'd been convinced that you needed the right kind of money, (friends who'd deeply desired to be part of what I was doing but hadn't actually invested any of their own money) backed out. When I recruited my buddies Jonathan and Dave (both of whom are strong-willed and confident), others on my would-be team decided they wouldn't be. Everyone had an opinion (at least one) about which they felt strongly.

There were people who "knew" how to structure a company and people who "knew" how to position and market a product and people who "knew" this and that. The only problem was that, for each expert who knew this, there was another who disagreed with her. After a day of meetings, I'd start to wonder if I knew anything at all. I learned quickly to listen, but not follow blindly, not matter what the credentials of the speaker were.

Delusional or visionary? Arrogant or confident? Stupid or brilliant? Smart or lucky? I have no idea. When I listened to the story about Duke Fightmaster, I could only think, "There but for the grace of Wall Street go I."

It's all easy to see in retrospect, but how fine the line. In the moment, how do you know?

Can you know?

Does it matter?

In the end, I'm glad that I took the chances that I did (and I bet that Duke is too). I'm glad that they worked out the way they did (and I'm sure Duke would have preferred another temporary ending), but even if they didn't, I would have wanted to do it anyway. I can't imagine a future where I sit on the front porch with my grandchildren gathered round and they ask me, "Grandpa, tell us again about the time you almost left your job and started a company. Please!"

OK, I can imagine it, but it kind of makes me cringe.

When I started typing, I thought I was writing about how you know whether you're running headlong into the future or into a brick wall. But now I think it doesn't really matter. Even if it is a brick wall that you hit, you learn so much when you throw off the shackles of convention and pursue whatever inspires you with all your strength, mind and heart. Perhaps you learn even more when you hit a wall.

John Chambers, the iconic CEO of Cisco Systems, completely crashed Wang Systems, before going on to his position at Cisco. Thomas Edison blew up lots of stuff on his way to creating the first light bulb. Maybe crashing and blowing up are just part of the process.

How do you know?

Does it matter?

Happy Friday!


  1. Tef, a few thoughts upon reading this post. I see a distinction between objective and subjective ways to evaluate one’s decisions and course of action as one proceeds. The objective way, say for this Duke guy or yourself, would be to look at the results – did Duke end up as Conan’s replacement or not, did you end up being profitable or not, etc, or how ever you define success in the venture. This is usually somewhat clearcut; BUT, the downside is that one only knows this at the ‘end’. And as many of these success stories have shown, the end is only when one stops (either by choice, or by death). It is possible (& probably advisable) to come up with intermediate milestones & progress checks to avoid backing a losing horse, so to speak, but that’s not always an exact science, given the large number of ventures that looked hopeless along the way. In your case, your eventual success bestows considerable credibility to your choices.

    But I think what most people struggle with when making decisions like these is the subjective ‘rightness’. Am I doing the ‘right’ thing? Or am I a fool? Your labels were great: delusional/visionary, arrogant/confident, stupid/brilliant, smart/lucky. All of these are subjective, relative; ways to obtain society-based approval to bolster our weak sense of security, ultimately so we can feel good about our decisions. I suppose a variety of yardsticks could be used to make this evaluation:

    - Good is what the greatest number of people think is good. Statistically, most people have an 8-5 job, a family, a home, most of the latest gadgets, take a vacation once in a while, indulge in modest hobbies on weekends, etc etc. So choices that show the best chances of ending up here are the ‘good’ ones.

    - Good is what one’s immediate peer group thinks is good. If the group in which you hang out tends to patronize bars, watch a lot of football, drink beer, etc, that’s what you do. If your peer group is a bunch of overachievers that do all the AP courses in school and intend to only apply to Ivy League schools, that’s what you prioritize. A variation on this theme is when you aspire to a particular group but don’t actually get to hang out with them – Wall Street tycoons, rock stars, etc.

    - Good is the opposite of what your standard group does. This is what defines rebels. You can rebel against authority, culture, religion, parents, discipline, poverty, riches, education, …whatever.

    - Another yardstick, independent of a reference group, would be: Good is what you make of it afterwards. So even if a particular decision ended in objective failure, you can make it subjectively good by extracting a useful lesson from it, or identifying an objectively good consequence.

    - The final yardstick – use no yardstick. Introduce enough time and distance to make it inconsequential. Hate to drive in the snow? Either move south or wait till summer, and it’s not a problem anymore. Not enough money in the bank? Consider the untold millions on this planet who share your fate, or worse. Lost a loved one, failed in business, stuck in jail, suffering from addiction/disease? Consider 6 billion people on this planet, orbiting what is merely one of a 100-400 billion suns in this galaxy, in turn one of many hundreds of billions of galaxies in this universe, which physicists now believe is only one of many universes…

    You say you can’t imagine your grandchildren being inspired by a record of preferring security to adventure. I thought of another cringe-worthy scenario - living in a cardboard box under the bridge, with no porch and no grandchildren. Granted, it’s a fear-provoked scenario, but compared to that, sitting on a porch with uninspired grandchildren doesn’t look too bad :-).

    Ok, that was more than just a few thoughts… Hmmm…

  2. Throughout my life I have stood on the ground of both vision and delusion, I guess that's just who I am. I'm a creative person and when I decided in my twenties that I would place money ahead of following my inner creativity I began building a life for myself that looked good on the outside but was built on a faulty foundation. There was always something deep down inside telling me that I was heading in the wrong direction even though the people around me thought I was fine.

    It wasn't a conscious thought but I now see that what I was doing was tearing down the house completely to begin a new foundation from scratch. An authentic one. My tenacity as a talk show host was also a commitment to never sell myself out again. Now I can honestly say that I am living my truth. I don't regret it one bit, but I also wouldn't recommend it either. I've been through hell, admittedly by my own choices. In a way though I was already in hell before my adventure. I look at my journey as a journey of walking out of hell.

    I am now focusing on stand up comedy, writing and yoga. I've finished a screenplay and my new goal is to make a movie. When we are successful we party, when we fail we learn. I've learned a lot.

  3. Wow Sree, Duke, Great food for thought.

    Sree, I like the idea of idea of interim benchmarks, but the problem I've found with using them is that they only work when you're walking down a path the second time. The problem with blazing new trails is that you there are no benchmarks or signposts along the way to tell you how you're doing.

    I find this all the time when working with traditional project managers while developing new technologies; they'll want to know what the milestones are along the way and meanwhile I don't even know if what we're attempting is possible.

    I believe that it was Napoleon who said that "no battle plan survives the first incursion", and I believe that there's something of that here. Not only do benchmarks not apply, but it's highly likely that you'll toss everything and try another approach several times along the way.

    Further, having recently spent time developing implantable medical devices, I'm not sure about notions of subjective versus objective when it comes measuring progress and the likelihood of success in new territory. One of the themes I've found among successful investors is that they don't look at the metrics; they look at the team (or the individual), betting on the jockey, not the horse. I buy it. There are some people who succeed no matter what, and others who don't, no matter what, and as I found out while working with a team of engineers in Edinburgh, some who would rather die trying than win.

    "Good" is a good starting place and ultimately, it comes down to question "What is good for me?" Even if you change "good" along the way, it's really useful to know how and why you define "good" as you do.

    However, I think the truly important word to get in touch with is "want". How much do you want it? If you pursue what you truly want, then it's all good, and it can be all good in the moment.

    I think this gets to the "hell" part that Duke refers to. There's losing everything and then there's how you handle losing everything. To oversimplify a bit, some of us make losing everything a trauma that we never overcome; some of us experience it traumatically in the moment, but find the good in it in retrospect; and a small number of us are able to make it "all good" in the moment. The difference ranges from "damned to hell" to "to hell and back" to "hell?"

    I think that if you're "living your truth" (as Duke puts it), then the only regrets that can arise come from doubts about whether or not it's your truth that you're living. So, I keep coming back to the primary question being, "What do you want to do?"

    Once you've answered that, you may establish goals and benchmarks along the way, but they're not what drives you to get up every day and do what you do.

    Sree, I'm completely un-phased by the bridge/cardboard-box scenario, primarily because I can't see it happening, but also because, if it did find myself living in a box under a bridge, I'd figure it out. To me, to be given this amazing gift of life and then to hoard it would be the only tragedy.

    OK, that might have been a little overly dramatic. It's just that, if a story merits telling over and over, might as well make it the one you really wanted to tell.

    Thanks guys!

  4. Food for thought indeed, Tef & Duke, with dessert being the most delicious course as always. I agree, when you get to the root of the matter, the ultimate compass to use is What You Want.

  5. Thanks for sharing this collection of thoughts and stories. Every great achievevment starts with a person that bends tradition....and is thus viewed as crazy. I love being type cast - it means I'm in the film, not watching it!

    Duke Fightmaster for President!


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