You Make Money With Wins, You Make Friends With Losses

Brad Feld has a great post about the emotional toll of the collapse of the internet bubble.

Near the end, he writes:

When I reflect on my relationship with Seth, Jason, and Ryan much of the intense loyalty between us was forged in the period during and after the debacle that was the collapse of the Internet bubble. Some of my lifelong friendships, with people like Len Fassler, Dave Jilk, Jenny Lawton, Will Herman, Ilana Katz, and Warren Katz were solidified by the intensity of this time frame.

There really isn’t anything like going through a painful process with someone or a group of people to forge the bonds of friendship, loyalty, and trust that make for great professional and personal relationships.

When I look for partners in a business deal, I always start with the folks who I’ve been through tough times with. Because I know that they will hang with me again, just like they did the last time.

#VC & Technology

Comments (Archived):

  1. awaldstein

    Timely.I met with the founding team of Moai last week in SF.My favorite startup that went south in the bubble.Most painful loss as I personally brought a $350M acquisition offer from Siebel to the table and the board rejected it, bubble popped and well…..This group of people are honestly as close as friends who lived through this together as can be. A long time ago, we are all as a group deeply connected.

    1. JamesHRH

      Depending on then time frame, $350M would have looked like chump change.Nice Rolodex pull.

  2. William Mougayar

    So true, and true it was for me too, as a dotcom survivor with scars.

  3. kenberger

    From Brad’s post: “emotional diversification”.That’s a key reward for the investments in having a family. I’m thankful to have a phrase now to encapsulate that.

  4. jason wright

    crashes, losses,… plague (which we do have in the ICO space at the moment)?it all seems very dark. is there nothing to lift the spirits?EDIT 12:35 GMT:…at least Hillary Rodham Clinton and her network are not on the throne. that lifts my spirits every time i contemplate it.

  5. Nidhi Mevada

    True for all kind of relationships.

  6. Mike Cautillo

    Misery loves company…..just make sure they’re around for the good times too!!

  7. Tom Labus

    “Courage is grace under pressure” Hemingway.

    1. awaldstein

      This is about failure nor pressure.Different to me.

      1. Tom Labus

        In my experience when there is extreme pressure failure is just a few steps away. It’s a fine line.

        1. awaldstein

          I find startup life, bootstrapping especially to be all about pressure.Failing and making the decision when to call it quits something else.Posted on it awhile back.

  8. falicon

    ah…so *that’s* why I have so many friends (and very little money)!!! 🙂

    1. Twain Twain


  9. JamesHRH

    Tough times seem to be on your mind……KoC ( King of Crypto ).. Nice of you to send up a flare for folks.Just as importantly, losses tell you who you are not down with.

  10. Semil Shah

    I remember you saying a few times that it’s critical to find a few investment partners to “split” deals with. This is a good addition to that tip.

  11. creative group

    CONTRIBUTORS:Well the perfect storm for creating friendships and stories will be crypto-currency. Friend up folks.

  12. PhilipSugar

    When you lose money you know who your true friends really are.When you make money, you make friends. Everybody wants to be your friend. You are smarter, prettier, funnier, and even thinner than you were before you made a ton of money.When you lose money you also lose all of those with those people.It is only your true friends that still love you.

    1. LE

      When you lose money you also lose all of those with those people.Well for sure you would lose some people. But because of the halo effect you would not lose everyone that became your friend for what you consider to be the wrong reason.The fact is there are a host of factors that make someone want to be a friend or associate with another person. Generally it’s because there is some benefit to the ‘friend’. That benefit could be that they find the other person funny, entertaining, attractive, smart, interesting etc. or because they have toys or things that someone can enjoy. Maybe they have an attractive sister or brother or famous sibling. Also the halo of possibilities that associating with someone provides. [1] Many people are impressed with educational status, what schools someone went to, family status and so on. What I call ‘secondary meaning’. [2] Taking a step further most people would probably be friends with a celebrity just so they can tell others they are friends with a celebrity. Name drop. That’s a ‘benefit’. More so now with social media is my guess. Geez my stepdaughter is impressed that I do work for SNAP because she uses it!So while it sounds all good and pure to like someone for ‘who they are’ there are many degrees of that and I am not sure that one is necessarily better than the other. Or that the other reasons are not valid either.I think the halo effect is a built in survival skill that serves an important purpose.[1] There was a movie about rich kids years ago (by Jamie Johnson) and they interviewed a young Ivanka Trump. She said she didn’t understand why people were nice to her. After all it was her father with the money not her. It’s obvious though why they might have been (other than she is nice but that’s not the entire reason).[2] This varies and is not consistent for all people. Things that are universal aren’t secondary meaning because they are present in everyone. (My theory, not some academic concept).

  13. Pointsandfigures

    When the dings come you find out the true character of people

  14. JLM

    .Tough times don’t prevail, tough people do.It takes adversity to provide the friction to expose our character.In the end the most significant learning is what we learn about ourselves. We are all way tougher than we give ourselves credit for being.JLMwww.themusingsofthebigredca…

    1. Mark Essel

      I’m a 100x fiercer when I believe in what I’m doing, heck the multiplier is not a number.The reverse is also true.

  15. bfeld

    Well said. This is one of the reasons I’d follow you to the end of the world and back – any time, for anything.

    1. fredwilson


  16. creative group

    CONTRIBUTORS:Lose money you have the opportunity not to lose by selling now or hold and await the bubble and make friends.Which do you choose?

  17. Ed Street

    Fred, how do you reconcile the need for organizational HR diversity with the choice of new partners from shared adversity? I asked Brad the same question.

    1. fredwilson

      it is a dillemma

  18. brittblaser

    My first real job was flying C-130s in Vietnam. Was shot down delivering a spare tire to a buddy. Formative stuff.Post bubble for sure, we all knew it was unwinnable, as we’d been taught at OTS in 1965. Like John McCain, we were all losers.

    1. JLM

      .Can’t resist: “C-130 going down the strip, Airborne Ranger on a one way trip.”You get it, right?Airborne, all the way!JLM (Abn Rgr, combat engineer)www.themusingsofthebigredca…

  19. Pete Griffiths

    You can’t buy character.”A reputation takes a lifetime to earn but can be lost in a week.” Buffett

      1. george


    1. JLM

      .A week? Ten seconds.JLMwww.themusingsofthebigredca…

      1. Pete Griffiths

        You’re right. The bad choice was always fast, but these days it doesn’t take long to get out there, does it?

  20. Kirsten Lambertsen

    There’s nothing like hard times to bring out people’s true nature. And it can be really surprising who shines and who doesn’t.The surprising lesson I’ve learned is that people tend to respond with more respect and admiration when I share my hard-times anecdotes than when I share my amazing tales of success. Turns out people know, intuitively, that success can be mostly luck but how you get through the hard times is a real measure of character.

  21. Steven Kane

    Old cliche but true: You don’t really know someone until you’re in a foxhole with them.

  22. sigmaalgebra

    Now, now, if losses create friends, do wins create enemies? At times I’ve suspected so! I’ve had some wins that did create enemies, but I needed a comparison, say, some losses, and I’ve tried to avoid those! 🙂

    1. Mark Essel

      Our lateral thinking champion. If the devil had an advocate, he’d be fired to make way for you sir.

  23. Mark Essel

    Perfectly timed – as I wrestle free of a wildly successful enterprise that wasn’t headed where I wanted to be.Met some fantastic friends along the journey, that’s the BIG win – options I don’t have to pay uncle Sam for.

  24. Vinish Garg

    Ultimately, the sequence steers the bigger game! Friends (loss) first can help you in Money (wins) but cannot say the same other way around!



  26. fredwilson

    Listening now

  27. JLM

    .Stronger than an acre of garlic. Well played!Everybody on AVC should be required to compose and sing a song.JLMwww.themusingsofthebigredca…

  28. LE

    Didn’t listen yet.(So does a true friend tell you what you want to hear or what they really think?)

  29. PhilipSugar

    I really, really like. You know one thing we always say in our family when we lose somebody is “well done brother” and give them a light touch on the hand as they go to another place. Understand this has nothing to do with gender, I did it for my wife’s 98 year old grandmother.

  30. Rob Larson

    Is that your voice?

  31. Mark Essel

    Loved the song man, great stuff.

  32. Girish Mehta

    A true friend really thinks about what you want to hear.

  33. LE

    But that seems to indicate that someone is operating in their own best interest rather than the friends.Let’s say people listen to Charlie’s song. And they high five him and tell him they think it’s great. But it’s not. And they don’t think it is. But they tell him otherwise. So he gets all distracted and stops doing his day job. Thinks he can still be a star again. [1]A true friend gives him a true response. ‘Charlie’ doesn’t like it but I think that’s better for ‘Charlie’. No need at this point to perseverate over what could have been. [2][1] Next thing you know he becomes an alcoholic or drug addicted. Business goes down the drain. Marriage breaks up. Dog isn’t fed. Lawn isn’t mowed. Trash builds up. And so on.[2] And besides even if someone does have some talent it’s still an impossible climb that takes a great deal more, mainly luck.

  34. Girish Mehta

    1. You can tell the truth without thinking about what the other person wanted to hear.2. You can tell the truth after really thinking about what the other person wanted to hear.The latter can modify the delivery of your message to where it can be more helpful. Sometimes. (some other times, nothing you say will make a difference…sometimes, people listen to what they want to hear).Thinking about what the other person wants to hear can be about caring enough to make your message more effective and ultimately actionable, not necessarily changing your message.Finally, I agree with what you say that it can also mean the exact opposite.Life is about these nuances.

  35. JLM

    .There is no place in Hell for being kind. Try it.JLMwww.themusingsofthebigredca…

  36. Mark Essel

    Any heartfelt celebration with song is moving. The quality of his tenor or Melody has nothing to do with it, but they were pretty damn impressive too ;)I’m not cheering the compression waves – I’m cheering Charlie’s memory of a meaningful win.

  37. LE

    can be about caring enoughCaring. Another example of this is when someone invites you to a party, event, date and you don’t tell them you have no interest in their party etc. or that you have a better way to spend your time. You don’t say ‘well I’d go but Charlie’s party is usually more fun’ or ‘I like Charlie better’ or ‘would rather just be by myself’.What you do is you care about them enough to essentially lie to them. You make something up that sounds plausible and that is either believable or allows them to retain their pride.So in other words someone lying to you in that case isn’t entirely bad. It shows that they care enough about you to not tell you the truth.I never forget way back when I asked a girl out on a date that worked at a vendor. I thought she liked me because she was nice and flirty. So finally I got up the guts to ask her out. She not only replied ‘no’ (said she had a boyfriend) but then added ‘but even if I didn’t I wouldn’t go out with you’. I think she had aspergers. Wow thanks for being honest.

  38. Rob Larson

    Impressive, nicely done.You have the singing voice of a young man.Sounds great. And heartfelt.

  39. Twain Twain

    I wrote this poem the other day to complement F. Scott https://uploads.disquscdn.c… :He never showed up,Spot upon spot,She checked,In spaces known and clear,Where he was supposed to be,But their paths never crossed.The dandelions flew fast on the breeze.Before she knew it,The expanse of the Universe,Filled his void of non-existence,And in the embrace of Enlightenment,Her mind made peace with her heart.He never showed up.So she looked and stepped towards the future.

  40. Pointsandfigures

    If I actually sing and the world hears it, we will have crossed the rubicon into the seventh circle of hell.

  41. sigmaalgebra

    I’ll have to get out my violin, order a new set of strings Pirastro Eudoxa, have the bridge and sound post adjusted, have new hair in the bow, practice for a few weeks, write some music, and then I’ll contribute!Ah, sounds like an interruption in my work!

  42. JLM

    .Was that Zelda or one of his lovers?I just finished reading a book about F Scott’s wife, Zelda. They were a pair.Tonight, I go to my writers group to have one of my writings savaged. I may steal your poem.Not really. I have more than enough material to be savaged.JLMwww.themusingsofthebigredca…

  43. Lawrence Brass

    Whenever he doesn’t show up, remember you have your friends here in the ole’ bar.. Twain. 🙂

  44. sigmaalgebra

    Ah, Twain, it appears that that time F. Scott was sober! He finally started to figure it out about women! That smiling stuff, that’s a big part of the whole, good story.E.g., for that girlfriend I had when I was 14-15, those were the happiest hours of my life. Finally I figured out why: Those hours when we were together, she was smiling at me from being happy to be with me.So, right: Men, to be as happy as possible, work to make her happy so that when the two of you are together she will smile at you from being happy to be with you. That’s the happiest you can be!

  45. Mark Essel

    His loss 🙂

  46. Lawrence Brass

    I want to read some.. can’t say more because of an NDA. 🙂

  47. Twain Twain

    LOL. ‘The Beautiful and the Damned’ was indeed a fictional account of F Scott’s marriage to Zelda.My little ditty is about how there are no Prince Charmings on white horses so women just have to get on with their lives.

  48. JLM

    .Explain yourself, Lawrence.JLMwww.themusingsofthebigredca…

  49. Lawrence Brass

    I would love to read one of your stories, if you are willing to give me access to some of “the materials”, Sir.

  50. JLM

    .You will be sorry you ever said that.JLMwww.themusingsofthebigredca…

  51. JLM

    .OK, we may put you in the chorus. In the back, cause you’re tall.JLMwww.themusingsofthebigredca…

  52. Pointsandfigures

    No. No one wants it, not even in the shower. I believe God missed me when he was handing out tonal talent.

  53. cavepainting

    There are two categories of lies in life:a) To avoid hurting people.b) To take advantage of someone or to deliberately mislead with an agenda in mind.The former is more common than people care to admit. The latter is wrong, plain and simple.If someone is confused about the two, ask a simple question. Who is the lie supposed to help and who are you looking out for? If it is primarily yourself, it is more likely the latter than the former.

  54. sigmaalgebra

    > My little ditty is about how there are no Prince Charmings on white horses so women just have to get on with their lives.Better solution: Settle for a good man, less than a Prince Charming, and have a much better life than getting on with your life.You don’t want “your OWN life.” The last women I knew who wanted that tried for it all alone and got so badly hurt she killed herself. This is just what it sounded like:…Instead, you want to be one of two people who come together as a couple as in the standard start of marriage vowsWe gather together to join this man and this women with the bonds of Holy matrimony.There is…with 2.1M views — so some people get the message!Wagner’s not the only such composer. So, Felix, right, Mendelssohn, has…7.2M views so that still more people get the message. “Old as time”. Uh, @JLM, “Our generation didn’t invent love or marriage” or some such.Ah, nothing is more traditional than hundreds of years ago (the pictures will get you even if the music doesn’t)…6.5M views for some more people who get it.A long time ago Deanna Durbin got it across…Don’t mess it up. If you do it will be like Samuel Barber, Adagio for Strings, op.11…especially near the end.IMHO, Betty Friedan was a fantastically effective Communist saboteur of the US family. As the above music shows, she was not always successful. There was Mao, Stalin, and Hitler, and then for a much more destructive person Long Island housewife Betty Friedan. E.g., when she wrote her screed, the US baby business was booming, and now we’ve having so few babies we are quite literally going extinct. We’re talking 100 million or so dead babies.How do well with less than Prince Charming? Sure, smile at him. Then do well on the E. Fromm, The Art of Loving, I call the four point secret scorecard:(1) Knowledge. Give him knowledge of yourself. That’s, say, intimacy from between the ears and, net, better than the physical kinds.(2) Caring. Really care about him. Don’t engage in destructive competition with him. Where you can, help him.(3) Respect. Right, give him respect. So, he’s not Prince Charming, but he’s still yours and likely deserving of respect. If he does his part on these four, then he definitely deserves respect.(4) Responsiveness. Right, respond to him. The first, standard way is to smile at him. If he looks at you, smile back! If he says something to you, then give a nice, meaningful response.Only a tiny fraction of couples get a good average grade on all four. Being one of the best in the class doesn’t have to be really complicated.E.g., watch Herman Wouk, The Winds of War and see how the character Rhoda Henry violates all four! Then see how the character Pamela Tudsbury does really well on all four. So, Rhoda loses Pug Henry and Pamela wins him. Notice the scene with all the big collection of family pictures of Rhoda and Pug while Rhoda is ignoring those and cheating with her affair.I’m not sure that Wouk ever read Fromm, but likely there is more than one path to the four things Rhoda did wrong and Pamela did right!There’s more, but I’ll save that for Girls 101 for Dummies — Boys.

  55. Mark Essel

    Doing great!Older, more nerdy with node.js, data stores, real time data scaling and transitioning to a slower paced and more meaningful work life mix.This summer I was pretty strung out by work and accepted that I needed to switch up what I was doing. My curiosity and enthusiasm are already driving me to delayed interests. Picking up Elixir & deeper AI / algorithmic chops which have been zero priority as a lead backend operator.

  56. Twain Twain


  57. sigmaalgebra

    One of the best piano performances I ever heard. Definitely the best of that piece I ever heard. Amazing: Just a machine of wire, iron, and wood with some black marks on white paper and, then Arrau uses dynamics, continuity via the pedals, and timing, all exquisitely carefully and together, to create music, art.At Barenboim plays Beethoven Sonata No. 8 Op. 13 (Pathetique)IMHO, for a long time, Barenboim really understands music. It’s fun to see a good conductor play some good piano music because then get to hear how well he understands the music without having to get 100 musicians to perform it the way he wants!Yup, this music is famous, and with 2.6M views it and this performance are well liked!Likely the second movement is the world favorite from this piece and in this performance starts at about 9:40.That’s the music used near the beginning of Jurassic Park: The Lost World suggesting that it’s just the right stuff for any Upper East Side townhouse!Arrau and the Pathétique? Yup, at…with the second movement starting at about 9:10.A piano is so, call it, mechanical.A violin can be better in some respects and the human voice better, still.For violin, an example is at…with the Heifetz performance of the Bruch Scottish Fantasy. I have the CD. Supposedly it was one of the pieces of music where Heifetz showed “magic” and one of his favorites. Some of the passages are among my favorites in all of music.For a human voice, there’s, e.g., at…Grieg’s Solveig’s Song.

  58. Twain Twain

    There are artists/musicians/scientists/founders who are technically brilliant and then there are artists/musicians/scientists/founders who are that AND HAVE HEART.And we can FEEL THAT HEART when they play and in everything they do.That’s when we know we’re in the presence of human genius — as is the case with Arrau, :*).