Something powerful happens when a person who’s not a family member — and therefore someone you perceive as more objective — tells you, with their actions or their words, that he believes in you: You begin to believe in yourself.

I’ve known Brad and Amy Feld for a decade. Technology has made it easier to stay lightly in touch with a lot of people, but it hasn’t changed what’s required to maintain close relationships over a long period of time, which is good old-fashioned face to face time. And face time can be hard to come by. People get married, have kids, get divorced, change jobs, move around, move on. People get busy. I’m busy. I’m delighted it’s worked out that I’ve known them so well for so long.

A couple weeks ago, I spent a weekend at their place, which has become a cherished yearly tradition. It’s actually pretty simple. One weekend a year, I go to wherever they are, and we talk. Recently, I arrived at their home in Colorado late Friday night after they were already asleep. We got up at 8:30am the next morning and had breakfast. We talked from 8:30am until 4:30pm. I took a nap and Brad went for a run. Then we had dinner and talked from 6:30pm – 9pm. On Sunday I slept in, and we talked from about 10am to noon. What’d we talk about for more than a dozen hours? Everything. Yes, everything.

Each year when I drive back to the airport from their house, head full of ideas and heart full of energy, I think, “I’m going to write a blog post about the visit.” This time I am.

When I got started in Silicon Valley as a student, I knew exactly one person in the tech industry: Mike. He was a neighbor and family friend. Mike worked at PwC for years. He served as my all-in-one-MBA. He taught me that everything flows through networks — information, deals, opportunities. So he made some crucial early introductions for me. One of those introductions was to a partner at the venture capital firm Mobius named Greg. That partner (Greg), in 2002, introduced me in turn to one of his other partners — Brad.

The first time I met Brad, in 2003, my business partner Dave Richmond and I were pitching Comcate. It wasn’t right for his firm, but he made some intros to friends in the Bay Area. With him living in Colorado, and without a shared project, there wasn’t a natural reason for us to stay in good touch.

That changed in May, 2004, when Brad started blogging. I took a look at his site when he launched it and knew immediately that I had to do the same. The next month I started my own blog. These were the magical bygone days when you only had 30-40 feeds in your RSS reader and could read every post – we subscribed to each other’s feeds and found a new way to stay in touch. At one point, we both started sharing bookmarks in Delicious – a way to understand the “first derivative of someone’s thinking,” as he once put it. Eventually, with the virtual connection forged, we found time to see each other in person, and I got to know his wife Amy, and the annual visit tradition began.

They mentioned, last time I saw them, that it’s been cool seeing my own transformation over the decade. Indeed, when I think about inflection points in my life, they’ve been there for many of them. For example: (1) When I was building out my first company, Brad helped me think through various questions—he introduced me to Michael Porter’s work, for example. (2) When I took some time off after high school and wrote my first book, Brad wrote a guest essay in the book on mentorship. (3) Shortly before the book’s publication, I worked on some projects for he and his partners in Boulder for a few months in 2007. There, I had the opportunity to help David Cohen as he got TechStars off the ground. (4) When I brainstormed new venues for acquiring an education, I visited them in Alaska, and they—along with Chris Yeh—were the only friends of mine who supported my unconventional plan. (5) Shortly after my first girlfriend dumped me, I remember finding myself in Keystone, CO. Brad told me the story of his first failed marriage. (6) When I began talking to Reid about doing a book with him, Brad and Reid were on the Zynga board together, and Brad was helpful in greasing the wheels. When I published my second and third books, Brad — who’s been publishing several books as well — offered important perspective and advice.

I could go on. Point is, at moments of consequence, both good and bad, they’ve been a stream of encouragement and advice. At key decision points in my life, they’ve believed in me.

Brad and Amy themselves have transformed over the last decade as well, of course. In the time I’ve known him, Brad co-founded Foundry Group, which has emerged as one of the leading venture firms in the world, and TechStars, a leading tech accelerator. Amy joined the board of Wellesley and co-authored a book with Brad about how to be in a relationship with an entrepreneur (the best book on the topic). Together, they’ve entered mid-life, confronted looming signs of mortality, and grappled with meaning-of-life questions. You can find many inspiring, honest blog posts on these topics on Brad’s blog.

Equally striking about Brad and Amy, though, is what has not changed over the past decade. Their values. Their personalities. Their intensity. Their playfulness. Amy once told me your romantic partner is going to have certain idiosyncrasies and they won’t change. You’ll love them at first, and maybe forever. But if and when they begin to annoy rather than amuse you—you know you’ve got a problem. It’s safe to say they are still eminently amused by each other’s idiosyncrasies. And they’re still committed to their deeply held beliefs.

I’m incredibly grateful that I have them in my life. I’m also grateful to have befriended some of the people in their ever generous network, such as my good friends Stan James, Wendy Lea, Dave Jilk, and Heidi Roizen. It’s their multiplier effect.

I dedicated my first book My Start-up Life, which was about my first entrepreneurial adventure, to Mike the PwC neighbor, and to my parents, who supported me mightily in the process. For my second book The Start-up of You, about how to transform your career with entrepreneurial principles, I dedicated my portion to my 6th grade teacher who inspired me to memorize Apple’s Think Different ad, which helped kickstart my entrepreneurial verve. For my third book The Alliance, my portion of the dedication reads as follows: “To Brad and Amy Feld, for believing in me.”

Justin Wehr, a research assistant in behavioral health economics, blogs about posts-he-would-write-if-he-had-time. It's a smattering of interestingness:

A good question to ask anyone: "What don't you know, but wish you did?" [BC: Another good question to ask: What have you learned in the last year?]

Since discovering how to play audio faster (I am typically playing podcasts at 1.7x speed), it seems my comprehension has actually improved. Why might this be, and how can I test it?

Music is deeply personal and important to people, but at the same time it is incredibly boring to hear about other people's music preferences. Why is that?

Why don't retail stores (particularly Wal-Mart) generate revenue by allowing companies to put advertisements around the store?

Near death experiences. They have a fascinating history and are surprisingly common: 8 million people in the U.S. report having had one. Testable evidence for existence of the soul? There are many interesting studies on near death experiences and Duke even has a journal devoted to the subject.

Laughter, religion, and sleep: The three most puzzling things to psychologists.

Is productivity spiritually important as Marty Nemko suggests or just another form of hedonistic pleasure?

People should be paid for their attention on the internet. How can that be arranged? 

From this post alone it's pretty easy to tell that Justin would be a fun guy to have dinner with. Blogs are excellent filters in this respect. It's near impossible to write an interesting blog and be an uninteresting person.

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Speaking of interesting people, here's Stan James on how the complexity of a user interface evolves to meet a user's expectations. Compare the iPod of 2000 to the iPod of today. Here's Clay Shirky on the business model for local bookstores and the role they play in the community.

When I mourned the death of a hero last year, my friend Eliezer Yudkowsky left a comment:

Don't overlook that being able to be awed in someone else's presence is one of life's joys. Some people never get to experience that.

It got me thinking. Who else leaves me awed? Who are my icons? To shamelessly copy my friend Colin Marshall, I made a black-and-white portrait of nine people whose ideas or life-paths loom large in my own life, even if I don't know them personally or they are no longer alive. Click to enlarge the portrait.

 

"The people who are crazy enough to think they can change the world are the ones who do."

        – Steve Jobs

"The really important kind of freedom involves attention and awareness and discipline, and being able truly to care about other people and to sacrifice for them over and over in myriad petty, unsexy ways every day. That is real freedom. That is being educated, and understanding how to think. The alternative is unconsciousness, the default setting, the rat race, the constant gnawing sense of having had, and lost, some infinite thing…It is unimaginably hard to do this, to stay conscious and alive in the adult world day in and day out."

        – David Foster Wallace

"It's the ride that counts."

        – Brad Feld

"Precisely because the tyranny of opinion is such as to make eccentricity a reproach, it is desirable, in order to break through that tyranny, that people should be eccentric. Eccentricity has always abounded when and where strength of character has abounded; and the amount of eccentricity in a society has generally been proportional to the amount of genius, mental vigor, and moral courage which it contained. That so few now dare to be eccentric, marks the chief danger of the time."

        – John Stuart Mill

***

"Men want the same thing from their underwear that they want from women: a little bit of support, and a little bit of freedom."

        – Jerry Seinfeld

"Neuroscience is showing that all aspects of mental life — every emotion, every thought pattern, every memory — can be tied to the physiological activity or structure of the brain. Cognitive science has shown that feats that were formerly thought to be doable by mental stuff alone can be duplicated by machines, that motives and goals can be understood in terms of feedback and cybernetic mechanisms, and that thinking can be understood as a kind of computation."

        – Steven Pinker

"I suppose the basic intuition that I have about it is very simply, this is a world in which there is a possibility of things going extraordinarily well or extraordinarily badly, where both the good things and the bad things are bigger than people think."

        – Peter Thiel

"When we look up into the stars, we can choose among different feelings. On the sadder side, we can see emptiness and feel destruction and loss. But when I look up at the sky and gaze at the stars, I am joyful. I see a happy ending. I see interiority."

        – Tyler Cowen

"If you would not be forgotten
As soon as you are dead and rotten,
Either write things worthy reading,
Or do things worth the writing." 

        – Benjamin Franklin

My friend Penelope Trunk is the most influential careers blogger on the web, author of the hit book Brazen Careerist, and sought-after public speaker. She also runs a company called Brazen Careerist.

While I don't always agree with her, she is provocative, perceptive, honest, and kind, so it's a pleasure. She also regularly surprises me, which I really value. I recently chatted with her on instant messenger and the transcript is below and continues below the fold. We cover all sorts of topics.

First some words from Penelope about her new product, a "LinkedIn for Gen Y":

Gen Y needs a place to be found online by employers. Facebook is not appropriate for employers.  For obvious reasons. And LinkedIn is great for employers. It's very professional. But the average age there is 40…. I think young professionals want to be known for their ideas. And there is not a way to be known for your ideas on LinkedIn. On LinkedIn you are known for what you have done in the past. On Brazen Careerist you can be known for your ideas. Brazen Careerist is a bunch of conversations about professional-related topics.

Ben: You blog about sex a lot. Why?

Penelope: I think about it all the time. So it comes into my head a lot when I'm writing blog posts. I sort of wonder why it doesn't come into more peoples' heads when they are writing blog posts.

Ben: People censor themselves.

Penelope: Yeah. Well. I censor myself too. I guess it's just we each have different types of self-censoring.

Ben: What do you censor? Like, what kinds of topics?

Penelope: I knew you were gonna ask that. And then I thought to myself: Be careful. Because this is not going to be a good post for my company if I write really a topic that I censor.

Ben: If you write about having abortions, being sexually abused, etc, it's hard to think of topics that you would NOT write about.

Penelope: I never say bad stuff about my ex-husband. I think it's trashy.

Ben: What are your theories on writing? What makes good writing?

Penelope: Being interesting. I know people think I write about sex, bulimia etc because it'll always be interesting. But you can find ten million blog posts about those topics that are painfully boring. Interesting isn't really about the topic. Any topic can be good or bad.

Ben: So being an interesting PERSON makes your writing more interesting.

Penelope: I think interesting sentences makes writing interesting. I think all people are interesting if you talk with them about the right stuff.

Ben: It doesn't mean they can write about things interestingly. All people are interesting to an extent; not all people are good writers

Penelope: Yes. Right. I think good writing takes tons and tons of practice. Also, I throw out a ton of blog posts. People think they just roll off my keyboard. They don't. Do you feel the same? that a good post takes tons of work?

Ben: Absolutely. For the quality that I aspire to, I am slow, and I often still don't meet that quality level.

Penelope: Sometimes I like reading your blog just because you make me feel good about craft. Because I can tell how much you care about craft and then I don't care so much that I spent two hours on the links to a post.

Ben: This is what I'm interested in. Craft. Having an interesting life is one thing. Being able to tell it interestingly requires some craftsmanship, or something.

Penelope: Oh. That's an important point. At some point in my life, I realized I could support myself just sitting at my kitchen table writing every day. But I worried that my life would not be complicated enough to be written about.

Ben: So your entrepreneurship gives you material?

Penelope: Yeah. I think that is true. Well, struggling to figure out how to do my life — in many aspects of life — gives me material. I couldn't be Dooce. At home with my family writing about being at home with my family. I need more drama….not that she doesn't have drama.

Ben: Alain de Botton has an interesting point on this. He says the professionalization of writing — novelists who write fiction full time — has made it so much fiction is disconnected from life as it's experienced by most people.

Penelope: Totally agree. And the French have this problem more than any other culture.

Ben: The "novelist on the side" — someone who's also holding down a day job, or did for most of his life — has more valuable insight.

Penelope: Yeah. I love Raymond Carver for this. His life was so hard, and he had no time to write. And he still did.

Ben: Does being a good writer help you in your entrepreneurship? Most people in business, I've found, are terrible writers. And they still do fine. Chris Yeh, of course, is an exception. Great writer. Great entrepreneur.

Penelope: I think I make more connections through being a good writer. Chris is a good example — I connect well with him, and often, through writing.

Ben: Yeah, in your case, your blog is so tied up in your business that I'm sure there are tons of benefits. Can I make an observation about what I think your favorite phrase is in blog posts?

Penelope: Yes.

Ben: "And you know what?" That rhetorical question.

Penelope: I love that. I love feeling like I'm talking with someone. You make me laugh. You are smart.

Ben: It makes your posts more conversational. "Conversation" gets thrown around a lot. You do it when talking about Brazen Careerist. “People are going to have conversations” etc etc. But it's not easy to have a good conversation in-person, let alone in writing.

Penelope: Yeah. That's true. I think you know from our lunches and dinners that I'm awkward to talk to. Which I think makes me really really want to connect through conversation online. And I think you can tell when someone really really wants to connect, and when it's BS conversation.

The conversation continues to cover therapy culture, elitism, blogging, obtaining advice, and dating.

Continue reading “A Chat with Penelope Trunk: IM Transcript”

My friend Colin, in a wonderfully honest blog post, writes: “I'm going back to AA. Jesus. Somebody kill me.”

In March I spent a couple weeks in Colombia. Colin (last name omitted by request), who lives in Bogota, saw my tweet about heading down there and reached out asking if I wanted to meet up. His bio on Twitter reads: "Sexually-frustrated, alcoholic gringo in latin america." I was intrigued. I sent him an email asking for more info on his background. It only took a few emails for me to figure out that he was smart and thoughtful and interesting. He said he had been a long-time reader of my blog. We agreed to meet-up on my last night in Bogota.

For me it was an exercise in randomness. His online presence suggested he was unlike me. One of his blogs, Expat Chronicles, contains stories (which probably will offend many readers) about his exploits on the Latin America nightlife scene. In his own words: "This is a blog for Lonely Planet types and chronic travelers, those curious about the world, people who drink too much, guys with Latina fetishes, and filthy degenerates. People like me." Here's a post about going to a brothel. Here's a post titled "Peruanas' Gringo Desire Reaffirmed." His personal blog contains more general musings on the world.

I drink but not a ton, I don't do drugs, I've never been in jail nor have I patronized brothels. Meanwhile, Colin talks about all these things freely on his blog. I saw meeting him as an opportunity to understand the perspective of someone who has accumulated life experiences different from my own. We met over dinner, about which Colin posted a detailed blow-by-blow.

What impressed me most about Colin was his perseverance. He's had a tough life. It started with a grab bag of childhood traumas, followed by unfortunate run-ins with the law and school problems. Chronic alcohol and drug use compounded all of the above. At some point he decided to move to Latin America, leaving friends and family behind, and create a new life for himself. With his recent post on taking control of his alcohol problem, Colin is not just talking the talk when it comes to improving his life — he's taking concrete steps in the right direction

The other striking thing about him is his self-awareness. At dinner he displayed a tremendous ability to analyze himself and his actions, even if his own conclusions proved devastating to his character. Brutal honesty over charitable narratives or excuses: I like this.

People who have overcome real adversity in their life are not only more interesting than their silver-spooned counterparts, but they also seem to be the ones who become the most powerful and inspirational leaders. I expect Colin will be a future star of some kind.

He lives in Bogota and is available for freelance writing and web development. Email me and I’ll connect you with him if you’re interested.

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Here's Colin's post on how Latin Americans perceive love and romance more intensely than Americans. Speaking of honesty, my friend Penelope just blogged about being physically and sexually abused as a child. Wow.