The Many Sides of Friendship

Each quarter Chris Yeh and I convene about 20 of our friends on the peninsula and 20 of our friends in San Francisco for a conversation over lunch. Each lunch, called the Junto, has a theme. So far we've discussed and debated happiness, love, belief systems, humor, storytelling, death, Americanism, and this quarter: friendship.

My friendships are important to me and an area of my life to which I devote a lot of energy. My thinking about the topic generates questions that I felt grateful to be able to discuss at the Junto: What are the types of friendship? Should all friendships be bi-directional / fully reciprocal? Can you be close friends with people you hire or fire? How do you develop emotional intimacy with professional friends and intellectual energy with childhood emotional friends? Can you have a composite best friend instead of a single best friend?

Below are some of the key nuggets from our conversations. Full notes are here. (I missed some notes due to my laughter control issues in the very amusing San Francisco conversation.)

  • The measure of depth is trust. Trust is engendered by the things you share, since that makes their actions predictable. The more shared experiences you have, the more predictable they become.
  • The more settings in which you see a friend, the more you can trust that person. The person you only see in one setting can't be relied upon in other settings. That's how fraternity initiations work. That's why off-sites work.
  • Emotional connection is what switches someone from an acquaintance to a friend.
  • How can you add an emotional dimension to professional/intellectual relationships? How can you add an intellectual dimension to childhood relationships?
  • A lot of CEOs believe that they can't have a friendship with a subordinate or co-worker. But they also know that they need to be able to motivate people. So they share stories to establish an emotional connection.
  • A regular friend helps you move; a true friend helps you move a body. Use this to determine how many close friends you have – for how many people would you help move a body?
  • How do you break up with a friend? We don't have a script for doing this like we have for romantic breakups.
  • Friendships can by asymmetrical. Sometimes the "value" that flows back and forth takes different forms. Socialists worry about asymmetry. Capitalists only care if the two parties enter into a willing exchange. Is it wrong to think about "providing value" to a friend?
  • The best friendships are reciprocal but you don't keep score.
  • Do you have a best friend or a composite best friend? It's hard to find a single friend who fulfills all the different friendship needs you might have. Plus, a composite best friend eliminates the single point of failure ("The Voltron model of friendship.") Is the concept of "best friend" an antiquated notion?
  • In a good friendship, the whole is better than the sum of the parts.
  • U.S. is more transactional than other countries. Other countries see friends more immediately as "family."
  • Is it harder now to form deep friendships than it was in the past? If we're more mobile, perhaps yes. Simple math: You can know more people these days, which dramatically divides your attention across more relationships.
  • You want your friends to be able to criticize you but not judge you.
  • The quality of your relationship with others depends on your relationship with yourself. Do you love yourself?
  • It's impossible for someone to be your friend if you're not having fun with him. Having fun with the person is a universal value of friendship, despite in general it being a very personal and individual thing.
  • In California, after one meeting you're friends with the person, after two meetings you're good friends, after three meetings you're best friends.
  • Technology has expanded our capacity to maintain connections in the outer circles but doesn't affect how many relationships we can maintain in our inner circles.

Here's David Brooks' definition of friendship. Here are my favorite lines from Montaigne's book on the topic.

Failing Forward: Dealing with and Learning from Failure

Every quarter Chris Yeh and I convene some friends in the Bay Area to talk about topics that are not usually talked about. We've had conversations about humor, happiness, Americanism, storytelling, death, love, belief systems, and advice. This time the Silicon Valley Junto met to discuss Failing Forward: Dealing with and Learning from Personal and Professional Failure.

In entrepreneurial circles failure is absolutely part of the game. If you haven't failed, you haven't lived, as they say. Probably the most inspiring aspect of Silicon Valley is how many failed entrepreneurs there are who get back on the saddle. Here are some general notes that I took from the Junto conversations:

  • People whose identity is wrapped up in being “successful” tend to take on projects / tasks that are easier to lower their chances of failure.
  • Introspection produces wisdom. Success doesn’t produce introspection.
  • If you’ve "failed" by conventional standards, but you’re happy, it doesn’t matter.
  • People we see as happy usually have a way to measure failure.
  • Repeated failure can be a lifestyle. The importance of lots of little “oops" as opposed to one big "oops."
  • Failure is the intrusion of reality into our perception of ourselves.
  • Successful failure helps you realize personal competencies.
  • Some baseball players go 4 for 10 at bat and they’re still considered some of the greatest hitters of all time. Success is relative. In Latin America, for example, a "successful" company can mean not selling it but rather keeping it and passing it onto your kids for them to run.
  • Be terrified of failure and avoid failure until the moment it arrives, then be able to let go (and ignore sunk costs) and embrace it / learn from it. This is tough: you don't want failure, but you do want to see the silver lining when it happens.
  • What's harder – personal or professional failure? Consensus: personal.
  • One approach is to not believe in failure. If you fail, just change the rules of the game. If you fail, just continue pursuing the larger vision in a different way.
  • A very hard question: when to quit? When to accept failure versus to keep going and keep being persistent?
  • It's possible for something to "fail" but not be a "failure."
  • Book recommendations: Mindset: The New Psychology of Success and Code Named Ginger.

Here are Jackie Danicki's notes from the meeting.

If I Were You…The Giving and Receiving of Advice

The Silicon Valley Junto, a discussion society Chris Yeh and I run where we bring together friends over lunch about once a quarter, convened today in Menlo Park for the topic:
If I Were You…Advice Giving, Advice Receiving, and the Best/Worst Advice You Ever Got. We were inspired by this Fortune magazine feature where various CEOs answered this question.

Our lively and stimulating discussion covered several bases on the topic of advice. Here are some notes:

  • When you give advice, give the person options, and let them choose the best path. People hate to be told what to do — need to make them feel empowered to make the decision for themselves.
  • The quality of the advice — that is, whether the advice could be considered good or bad — is not necessarily connected to the ultimate consequences of following the advice. For example, if you advise someone to invest their money prudently in the stock market, and instead they liquidate all savings and buy lottery tickets, and win the lottery, did you offer bad advice? Can the quality of advice be judged based on the results that ensue from following it?
  • When giving advice, include the word "because" — it increases eventual absorption, regardless of what you say after the word "because."
  • Are advice givers’ primarily concerned about the advice-receiver following through on the advice? Usually. Usually the you want to frame your advice in a way that will best inspire action and a change in behavior. But sometimes the advice giver doesn’t have this objective; sometimes he just wants to feel superior, etc.
  • Remember four things when giving advice:
    • The role and responsibilities of the person on the other side of the table. See the situation from their perspective.
    • Your intentions — keep them pure
    • The delivery itself — focus on tone and spirit in which advice is delivered. This is crucial.
    • Summary — close off the interaction, make sure everyone is on the same page. Whether it’s a one minute conversation or four hour meeting, get some closure and action items.
  • Much of advice giving and receiving is just good communication tactics and good sales techniques.
  • When you seek advice, should you consult the domain expert or someone who knows you best? Your mother may know you best but she may not know the industry you’re considering going in to. Domain expert knows the market but doesn’t know your individual differences.
    • Get advice first from the domain expert to get a model and assess your choices. Then consult the person who really knows you to understand which choice makes most sense for you.
  • When you give advice, it’s easy to fan the embers but hard to strike a new fire. So listen carefully to their situation and find some aspect of it that you can build upon and emphasize. This will result in best outcome, rather than trying to instill an entirely new idea or some concept that’s not already part of their framework. [BC: This is very insightful.]
  • Actionable advice is best advice. Saying "speak up more" to someone who doesn’t talk in meetings is not actionable; saying "say at least three things in the meeting" is more clearly actionable.
  • The advice giver can be changed when he gives advice. That is, even though he’s doling out suggestions to someone else, that process can change the person usually for the better.
  • People who are "unconsciously competent" are not the best people to ask for advice. True experts often can’t explain what they’re doing and why.
  • Good advice givers have self-knowledge. They know their own biases and discount them before giving advice.

Related Posts:

– We overvalue advice when the situation is hard, undervalue advice when situation / problem is easy
– You can’t give advice until you’ve thoroughly acknowledged you understand how busy the other person is
– More general thoughts on the topic of advice, including "sometimes people ask for advice but what they really want is your attention."
– Even when someone discloses their bias before giving advice, we still don’t discount the advice enough. Say our mechanic tells us we need to buy some repairs. Clearly he’s biased but we tend to forget about the bias.
How to be a good mentee — be good at asking for and taking advice.

“How Happy Are You?” Is Unreliable

At the Silicon Valley Junto last week, where we discussed belief systems, I said I believed that the pursuit of happiness is the most important pursuit. That happiness should be the fundamental benchmark in our life. Eliezer Yudkowsky took issue with this and asked me, "Is there anything you do that isn’t for the sake of your short-term OR long-term happiness?" I couldn’t think of anything, but it’s an interesting question.

Today, Arnold Kling blogs about happiness research, and says:

I still think that the question "How happy are you?" is going to deliver unreliable answers.

Arnold is skeptical about research which tracks individuals over time and attempts to draw conclusions about what types of behavior will lead to someone being more happy. He says:

Suppose that research shows in some reliable way that most people are happy doing X. Is it not possible for people to have different tastes? If research shows that people who eat tuna fish are happy, does that mean I should eat tuna fish?

No, but it means you ought to consider tuna fish. Try it and see how you like it. If research shows that large numbers of people report higher happiness levels when they are with other people, and you’re a hermit, it means you should try to be more social, if you care about happiness. No guarantees though. Stay a hermit if it makes YOU more happy.

Happiness research told me that people tend to be happy when they drive, because they like the sense of control. I had never minded driving, but after reading that, I drove with this idea in mind. I like driving. I like the sense of control and listening to music or audiobooks. Or getting to talk on the phone. I now consciously associate driving with my happiness.

But I do have sympathy for Arnold’s larger point. Over the past year I have become much less trusting of someone’s own introspections. I appreciate much more the role of signaling. And basically think that a lot of people just don’t know how they feel, or what they want, or what actually makes them happy. In business, this is why focus groups ("What kind of product do you want"?) are notoriously unreliable. In life, this is probably why relationships fall apart or communications break down.

Your Last Three Minutes: What Would You Say?

The speechmaker is given no more than three minutes and is instructed to imagine that, as soon as the talk concludes, he or she dies. My friend said that the speeches were uniformly riveting, but, more notably, they were surprising. The men and women charged with the honor of giving these speeches clearly thought hard about what was most essential for them to say, and often it wasn’t at all what you might expect from a senator, a world-renowned physicist, or a CFO. – Eugene O’Kelly

That was the exercise (pdf) that opened up this past quarter’s Silicon Valley Junto discussion on death and mortality. The SV Junto is an "intellectual salon" modeled on Ben Franklin’s Junto. Chris and I started it a year and a half ago.

We had some intense and wonderfully honest / emotional conversations. One point that came up which has been rattling around in my mind is whether it’s possible to achieve the clarity and "life changing experience" that many people have during a grieving process without actually having a grieving process. It seems like the pain threshold needs to be high enough to truly jolt you out of your default system and appreciate the preciousness of each day, the importance of relationships you take for granted. Dealing with a death meets that threshold; what other things?

Like most people at the Junto, I find benefit from pondering my own mortality. At a practical level, of course, there are various loose ends that if not tied up have the potential to wreck families and relationships. Equally important are the "spiritual" and emotional issues around how you choose to live a life of finite time (if you don’t believe in an afterlife).

Much more to write about on this topic, but for now I’ll simply point you to the 3 minute drill PDF used for the Junto; the text of Tim Taylor’s speech; here is Gayle’s; here is Eliezer Yudowksy’s email to friends after his brother’s tragic death.

Once Upon a Business…The Role of Storytelling in Leadership, Management, and Entrepreneurship

The Silicon Valley Junto — an intellectual discussion society that Chris and I run — met a few weeks ago around the topic Once Upon a Business…The Role of Storytelling in Leadership, Management, and Entrepreneurship.

David Cowan kicked it off with an oral telling of a story he recounted on his blog: How do you get to Europe on an expired passport?" It’s an awesome story (most disastrous travel adventures are!) and David did a masterful job telling it. Since that meeting I’ve been thinking about how I can improve my own storytelling techniques. In my speeches this past month I always started with a story and it seemed effective. But I know I can improve.


So I recently re-read this e-book / PDF on storytelling techniques in the workplace. Below are a few of the tips.

To be a good story it should:

• Be brief and simple

• Be told from the perspective of a single character

• Describe a dilemma that is familiar to the audience

• Have a degree of strangeness or peculiarity to capture the audience’s interest and stimulate the imagination

• Be at the same time plausible and oddly familiar

• Be true (or have an element of truth)

• Have a happy ending (or give hope)

• Be told with a bit of flair and passion.

How to tell a good story:

• Pretend that you are confident – don’t make apologies as you start, either with your body language or your words.

• Relax, breathe and play – this is meant to be fun!

• Don’t memorize it. Tell it with your own words and your own images.

• If you get stuck, keep going. There are no mistakes, because no one knows what you were going to say, so they can’t tell if you’ve messed up. Think on your feet and improvise – sometimes you will stumble on real gems.

• Keep your stories short (10 minutes or less).

• Pay attention to pacing. Use moments of silence.

• Take time to finish well. Don’t rush through the punch line.

Is Love the Killer App? Do Nice Guys Win?

The Silicon Valley Junto, the Bay Area’s preeminent intellectual discussion society for business and technology executives, convened this quarter to discuss: Love is the Killer App: The Soft Heart in Business. Do nice guys finish first?

Chris Yeh and I started the Junto to continue the tradition of Ben Franklin, a remarkable guy, who in 1727 hosted 12 of his friends on a weekly basis to discuss the issues of the day. The Silicon Valley version attempts to bring our smartest friends into a room over pizza once a quarter to talk about something other than web 2.0. Past topics have included Americanism, humor, and happiness.

"Love is the Killer App" is the name of Tim Sanders book, which I just read, and enjoyed quite a bit. You can find my rough summary here.

After participating in both the Palo Alto and San Francisco discussions, I can safely say that I think compassion and love in the workplace — if defined as a genuine sense of caring and a proactive drive to help others out selflessly — is a killer app. Here are some of my notes:

  • Remember the Buddhist loop — to be selfless can be selfish.
  • Compassion will be beneficial in the long run, just remember the long run may be 20 years.
  • Yes, assholes sometimes win in business. Life’s not fair. But most highly effective CEOs lead with warmth.
  • With an increase in transparency thanks to the internet, nice guys should win more.
  • To show love in the workplace means you will share your knowledge and network.
  • How can you be more compassionate in the workplace?
    • Actually listen to people, and care about what they say. Everyone yearns for respect.
    • Understand people’s responsibilities — what are they trying to get done everyday
    • Look to help others — "Let me know how I can help you"
    • Care about their life outside work
    • Look for the best parts of someone and compliment it. Reinforce someone’s strengths.
    • Most important: be genuine. It’s gotta come from the heart.
  • It takes 100 positive interactions / actions to make up for one negative interaction.

What’s your experience been? Are the successful people you know (by traditional definitions) compassionate and "nice"? Or does the hard ass win more often? How do you express compassion?

Here are Susan Etlinger of the Horn Group’s thoughts on the Junto.


Funny Business: Using Humor to Thrive in the Professional World

Each quarter the Silicon Valley Junto, a discussion forum for business and technology executives that Chris Yeh and I run, gathers to discuss an intellectual topic that’s not directly related to business or technology. It’s an invitation-only lunch held on the peninsula and in San Francisco.

Our topic this quarter was: Funny Business: Using Humor to Thrive in the Professional World.

At the Trinity Ventures office in Menlo Park about a dozen super interesting people gathered to analyze this very serious issue. In San Francisco, at the North American headquarters of Comcate, Inc., a dozen people from slightly different backgrounds (more women, more non-profit heads) tackled the same topic.

Check out the notes from the meeting for the insights we collectively gathered. If you want them in more organized fashion you’ll have to wait for the e-book on humor Chris and I are writing. Here’s Tim Taylor’s useful post about the meeting, and Jackie Danicki’s post.

Here are photos from the two meetings on Flickr.

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Be Funny: Humor for the Businessperson

Some day, Chris Yeh and I will start a secular church and a political party (economically conservative and socially liberal). But for now, we’re sticking to the Silicon Valley Junto and …e-books.

We have two e-book ideas. The first is on humor and business. We think humor is really important. People who can integrate belly-laugh quality humor in their daily business lives are in a class of their own, I think. So Chris and I want to publish a low-cost, PDF-style e-book that can make funny people funnier and dull people manageable. Hell, we’re even throwing in a situational matrix. It will probably be several months until this is done — since both of us really don’t even have time to do this — but so long as Chris’ kids require tuition money, we all have to chip in somehow.

Go add your ideas, thoughts, and examples on this public wiki so we can make it good. Password: humor

Incidentally, I just heard this NPR piece on humor in politics, in which former senator Alan Simpson says:

"You show me a humorless person and I’ll show you a guy I can always whip in a debate."

"My mother always taught me humor was the universal solvent against the abrasive elements of life."

Conversation: The Greatest, Most Lasting, Most Innocent, Most Useful Pleasure of Life

I practically drooled over Russell Baker’s piece (free, print-length) in the New York Review of Books on the new book Conversation: A History of a Declining Art. An excellent conversation can often be elusive when everyone seems so short on time, so full of one-liners from talk radio. We must keep searching…For a good conversation is among the greatest pleasures in life.


Both participants listen attentively to each other; neither tries to promote himself by pleasing the other; both are obviously enjoying an intellectual workout; neither spoils the evening’s peaceable air by making a speech or letting disagreement flare into anger; they do not make tedious attempts to be witty….

Typically, Michael Oakeshott, the late British philosopher, thought conversation should have a distinctive lack of purpose. Conversation "has no determined course, we do not ask what it is ‘for,’" he said. It is "an unrehearsed intellectual adventure." As with gambling, "its significance lies neither in winning nor in losing, but in wagering."

…Montaigne finds a sharp conversational exchange physically and mentally exhilarating. Conversation, says Swift, is the "greatest, the most lasting, and the most innocent, as well as useful Pleasure of Life." Dr. Johnson thinks "there is in this world no real delight (excepting those of sensuality), but exchange of ideas in conversation."Montaigne speaks like a man for whom conversation is an exhilarating workout at the intellectual gym. Conversation, he said, was "the most fruitful and natural exercise of our mind" and "the most delightful activity in our lives."