Creative Prompts

The Gotham Gal and I listened to the recent Howard Stern interview of Paul McCartney yesterday on a drive from long island to NYC.

It’s a great interview, about 1 1/2 hours long, with incredible stories and lots of music.

Howard picks out songs, plays them, and Paul talks about how each one came about.

If you are a SiriusXM subscriber, you can listen on the web or SiriusXM mobile app.

I highly recommend it.

Near the end (1 hour 17 mins into the interview), Paul tells a story about being challenged by Dustin Hoffman at a dinner party to write a song “about anything.”

Paul accepts the challenge and so Dustin and the other guests decide Pablo Picasso’s last words should be the thing to write a song about.

Those words, as Picasso was heading to bed, were “drink to me, drink to my health, you know I can’t drink anymore.”

And so Paul wrote this song to those words.

And as he was telling this story to Howard, Paul says “I kind of like it, it puts you outside your comfort zone for an hour.”

I can totally relate to that.

This blog is that way.

I wake up every morning not knowing what I am going to write and before heading off to the gym or work, or both, I have written something and posted it.

Most frequently I wake up with something on my mind that leads to the post of the day.

Which, coming back to Paul McCartney, is how many of Paul’s songs happened. He would wake up with a song in his head and then he’d get out the guitar or sit at the piano and play it.

The creative process is hard to comprehend, but working with what is on your mind, challenging yourself, and getting outside of your comfort zone are three tricks that have worked for me and apparently also Paul McCartney, arguably the greatest songwriter of our time.

#life lessons

Comments (Archived):

  1. Lawrence Brass

    Paul McCartney is on a roll since his remarkable carpool karaoke with James Corden.I think you’re also on a roll here at the blog since summer began, been enjoying the posts.Staying creative is so good for the soul. 🙂

    1. Alex Iskold

      Staying creative is so good for the soul ==> Ain’t that the truth!

    2. fredwilson


    3. Pointsandfigures

      That carpool Karaoke was hilarious. If you haven’t seen it watch it.

    4. Mac

      That was “remarkable”. Thanks.

      1. Lawrence Brass

        Those people at the pub did get a surprise! Watching them made me so happy.

  2. kidmercury

    All good until the last sentence. Paul Simon > Paul mccartney

      1. Tom Labus

        “I have my books And my poetry to protect me; I am shielded in my armor, Hiding in my room, safe within my womb. I touch no one and no one touches me. I am a rock, I am an island.”— Paul Simon

        1. Girish Mehta

          “In the clearing stands a boxer and a fighter by his trade,and he carries the reminders of every glove that laid him downor cut him ’till he cried out, in his anger and his shame:’I am leaving! I am leaving!’, but the fighter still remains.”- Paul Simon

    1. CJ

      I prefer Babyface to them both.

    2. Girish Mehta

      I don’t know if you know Hindi, but there’s this guy, Gulzar…All my favorite songwriters are in Hindi 🙂

      1. kidmercury

        i’m gujarati, so i know some hindi, but not enough to understand the lyrics to most songs, unfortunately 🙁 also in my home growing up my parents only listened to religious music so that was all i got exposed to 😀

        1. Girish Mehta

          Ah, ok.Gulzar is peerless. Hindi/Urdu along with other North Indian dialects.

  3. LIAD

    Watched the highlights on YouTube.Loved the bit about where the song names and lyrics came from.I liked the name Elanor. And Rigby just went well with it.When I was upset my aunt used to say, just let it be.Billionaire, global superstar and totally down to earth. Self deprecating. Honest. I like .

  4. Alex Iskold

    This reminds me a bit of early surrealism. Remember Guillaume Apollinaire, and other early surrealists, challenged each other to write down their stream of consciousness. They believed in importance of subconscious and creativity. There is little doubt we have layered brain, and that subconscious has massive power of pattern perception and creativity.Between the years of 1996 and 2001 I composed hundreds of songs and poems. I never edited them, just wrote them down as they came to me. The more I practiced the better (as told by others) I got.Similarly these days with blog posts. It is a creative process, the idea just comes and then you ride it, go along with it and let it develop.What you are doing is effectively a form of art, but mixed with a lot of discipline. You know you have to write daily, but you let go and allow for creativity to kick in. I am sure that like Paul M wrote this sound, you could write about any topic.Basically your brain is trained to do creative writing on demand.

    1. awaldstein

      I certainly remember reading Guillaume Apollinaire and all the Surrealists. Been some time so this is a welcome memory.

  5. awaldstein

    Your ability to blog every day and from the heart has been a source of inspiration and amazement to me.I’ve thanked you over the years.Thanks again Fred as it is not often that others accomplishments make my life better. This one does!

    1. fredwilson

      Thanks Arnold

  6. JimHirshfield

    There is a lot going on in the brain as we fall asleep and just as we wake, or roll over in the middle of the night. Remembering these thoughts and tapping into them is a secret to creativity. Thanks for sleeping all these years, it shows.

  7. Vendita Auto

    “getting outside of your comfort zone” “challenging yourself`” I guess we could try a week on the streets or work in A&E …………Night Arnold, Night Fred

  8. Tom Labus

    What a great start to the day. Thanks.

  9. Mac

    Your last paragraph is quotable…..and frameable. Wonderfully written.

  10. jason wright

    “The creative process is hard to comprehend”Is it desirable to try to comprehend the process? some creative people are haunted by the possibility that their creativity might desert them if they contemplate it too closely.p.s. McCartney is not particularly popular in the UK. He’s seen as being conceited.

    1. LE

      Well I mean he definitely has a basis to be conceited given all the smoke that is blown at him for so many years.The other things about celebrities is that I am pretty sure they think close to everyone loves them or thinks they are great. Because anyone and everyone that comes in contact with them fawns over them and smiles even if they are not a fan. Part of the reason for this is that interaction with a celebrity, especially in the day and age of social media (but was true prior to that as well) is social currency. People will attempt to use it to get a positive reaction out of someone else that they know or come in contact with. And pretty much everyone does this even if they don’t personally care about the celebrity. So the celebrity thinks people like them (and for sure some do and are super fans) but most others are just feeding or and trading in the aura to enhance who they are. (Party in the brain territory).Anyway back to the point ‘everyone loves them’. I mean you are, say, Billy Joel giving a concert at the old Met’s stadium and it’s packed to the gills and everyone is screaming. But of course there are hundreds of millions of people that don’t listen to your music or don’t care about you or your songs and are not fans. But you don’t see them. And if you do (say you stop off at some airport) those people (that don’t care for you) are nice to you and act like they are into you simply because they can then tell others (who might care) that they met you. And then everyone is happy and excited.

  11. Guy Lepage

    This is a well-known concept amongst creative directors and art directors. We are taught to constantly “change your environment. Go for a walk, work from a new place, etc.” When working on “tomorrow’s garbage” you’re constantly creating something new for such a short time frame. In doing so, it’s a high pressure environment to always be coming up with new ideas and concepts. Forcing yourself to think outside the box is very difficult, it becomes a little easier to do so when having others do the initial thinking for you. suggestions from conversations and changing your environment, assist withnew discoveries.

    1. LE

      Go for a walk, work from a new place, etc.”I’ve know that for a long time actually. And add ‘new people’.I’ve told the story here on AVC about being at a breakfast place in Beverly Hills and sitting at the table next to David Spade. I found at upon leaving from the hostess that he came in every day and sat at that table. I wanted to go back the next morning and strike up a conversation with him. My wife refused to do it she was to embarrassed. I said no it’s the opposite. He will like it because I will say things to him that he will think are bizarre and it will give him something to think about that will give him material. (I will add that he was sitting at the table and just scribbling notes and observing things happening in the restaurant). My point was that it was the opposite. The interaction, for a comedian, was good. Not bad.I think a definite issue with certain celebrities that need to be creative is that they have a hard time doing normal things with normal people once they become successful. So there less chance for inspiration that will lead to great lyrics or melody because there is less emotion.

      1. Richard

        Larry King in his radio says was as good as anyone at sitting down with a celebrity for a win win conversation.

        1. Andrew Cashion

          Larry is from Brooklyn, nobody can mess with blood from Brooklyn. My son has the some of the greatest blood from Brooklyn.

  12. Kirsten Lambertsen

    I accept your prompt.A fellow named Fred thought it rightto dub Sir McCartney The HeightBut despite Paul’s sick chopsmost don’t think he topsMaster Bowie, who declined to be Knight

    1. Girish Mehta

      Nicely done !

      1. Kirsten Lambertsen

        Thanks 😉

    2. Richard

      Let’s hope Andrew Dice Clay doesn’t post today 🙂

      1. Salt Shaker

        Hickory dickory dock, as Sir Paul turns back the clock. His voice was once on top, though by now it’s clearly not. A legend to all, though it’s starting to fall, hickory dickory dock.(Love the man and his work to death….but he frankly can no longer sing).

      2. Kirsten Lambertsen

        I pretty much hope that every day 😛

    1. Kirsten Lambertsen

      I hadn’t seen this. Delightful 🙂

  13. LE

    The creative process is hard to comprehend, but working with what is on your mind, challenging yourself, and getting outside of your comfort zone are three tricks that have worked for me and apparently also Paul McCartney, arguably the greatest songwriter of our time.Agree it works for you but it’s not still working for McCartney. He has 23 top 10 hits and the majority were before the readers of this blog were born. So apparently the process is more than that. You also need to be hungry and have adversity (and problems) for song writing. Maybe also drugs. And tragedy helps. Clapton (way overrated btw) writes “Tears in Heaven”. Textbook example. Clapton writes it after ‘Clapton’s four-year-old son, Conor, who fell from a New York apartment building in 1991’. That you see is the secret sauce. Elton John “Goodbye Norma Jean” (about Marilyn Monroe) then rebranded for Princess Diana (might have been the first time naming rights were extended in that way but I am no Jan Wenner to say that).…There is a huge difference between what you are doing and McCartney who by the way hasn’t really done many hits (that I know of) since way way way back. Has he? And the popularity pales in comparison to what the Beatles as a group did (which you could call a first mover advantage). And synergy.You on the other hand (and most people who get paid to be creative and earn their living that way), have to be creative constantly. Paul (sorry for the offense Paul), Billy Joel, Elton John and an endless list of musical types just live off of music they did in the past. And that past is when they were hungry, had adversity, and were climbing the ladder of fame. Even Ringo Starr is actually providing more entertainment value for many years with his concept of ‘The All Starr Band’ than McCartney is. Honestly. He brings in other artists and has a collective show and provides a ton of entertainment. But he is not writing any new songs or hits. So he is ‘creative’ in a much different way.…In what you do as a VC you are still a) Hungry b) Overcoming adversity c) Feel a need to continue to evolve and find the next big thing. That is more like what the rest of us feel everyday and deal with.Edit: d) Take Risks

    1. Richard

      Fred certainly has research skills and a lot of luck and good fortune, but I don’t see any evidence of this lead by creativity. Writing a few hundred words a day is certainly a discipline. But with the exposure Fred has to input throughout the year, it’s more about being a reporter (and a good one at that) than a creator.

    2. Salt Shaker

      McCartney is uber talented, but like many of today’s leading box office artists he’s living off his catalog. Interesting dynamic in that very few artists today, other than of the legacy variety, are killing it w/ tour revenue.Must take exception w/ your Clapton comment. He’s an extraordinary musician (and he still holds up live, unlike Sir Paul. Not in Paul’s class as a writer, though.)Once had the pleasure of playing billiards w/ Clapton (and his Producer) for an hour or two. A random encounter on the UWS. Couldn’t have been nicer.

      1. LE

        Couldn’t have been nicer.Ironically I just addressed this in a comment to Phil Sugar elsewhere:And if he is nice it could be because he is actually nice (I mean say to hotel staff) or because when you are a celebrity you have to be nice or word gets out really fast. (Leona Helmsley).My Mom once ran into Jay Leno. She talked for hours (I am exaggerating of course) about how nice he was. Like how could he not be ‘nice’?We have run into celebrities on hotel elevators. Always super nice. You also think more because you aren’t expecting it.Not trying to be cynical (it’s built in I don’t have to try) but next time ask him for his phone number. If you asked me (or anyone else on AVC) they’d probably say ‘sure’. Ask Clapton? Deer in headlights probably. Like huh?

        1. Salt Shaker

          It’s all about respect, and knowing when and where it’s okay to approach. A private setting, during a meal, with family, etc., 100% inappropriate. I’ve met a ton of well known athletes. Most nice, some 1st class dickheads. I was once having a breakfast meeting w/ Kareem Abdul Jabbar. People kept coming up to him during our breakfast and interrupting. Totally inappropriate, not because it was a meeting, but cause while someone is dining they should respect his/our privacy. You can see why celebs/athletes get tired of the bs. Their private lives isn’t (or shouldn’t be) in the public domain.

  14. Richard

    Those who were lucky enough to be born in the 40’s (it’s sad that democratic/government lead polices against the black population did not make it universally so) and successful had the best of all worlds, a magical mix of freedom, innnovation, large families, open spaces, great music.No birth starting point will ever experience this again on this planet.

  15. Sean Saulsbury

    “Creative prompts” are really just constraints, and the great irony is that constraints fuel creativity.

    1. Kirsten Lambertsen


  16. LE

    Near the end (1 hour 17 mins into the interview), Paul tells a story about being challenged by Dustin Hoffman at a dinner party to write a song “about anything.”I knew a guy who knew a guy who was kept up on the phone all night by Hoffman. As the story was being told to me it was ‘Dustin’ as in ‘we are on a first name basis’ you see.The topic was some project that Dustin wanted to do.The person who he was speaking to (a friend of an older friend of mine) was a writer. Dustin talked all night and this guy is trying to keep awake because he doesn’t want to tell Dustin that he needs to go to bed. Was some epic 8 hour phone call until ‘Dustin’ finally ended it.Sure that happens with dating. But in that case both parties typically are in agreement to keep talking.It’s interesting hearing what would be typically considered ‘name dropping’ (what my friend did or some may argue what I am doing) when Paul McCartney does it and it’s not ‘name’ dropping at all.Name dropping (at least my theory goes) has it’s roots back in the old country. In the olden days it was who you knew. To get anything done took connections to the right people to pull strings for you.Interesting video of when Paul McCartney came to the US for Billy Joel’s last concert at Mets Stadium. McCartney was late on the plane and they were able to get the plane landing priority at JFK and also a police escort to the stadium. At the stadium McCartney was driven by the same driver that drove him when he first came with the Beetles. So he meets that driver. And honestly could give two shits. The PR and marketing people loved it though ‘wow same guy wow’. Here is the video, worth a watch. Good thing there was no bad events as a result of the giving McCartneys plane priority landing. I can just see the headlines on that one.

    1. PhilipSugar

      I’ll humble brag. Yes I was on his floor at the Loews and went to his concert in MN.…No, he is not humble.

      1. LE

        I actually have coined a phrase with respect to people like that.It is:They care about everybody but yet they care about no oneTo break it down it means (if not apparent and obvious) they need the group but not the individual.McCartney, let’s say, hit it big when he was 22. (He was born in 1942 and came to the US in 1964). So basically from that point he he was living in another universe from everyday people. With the attention, adulation, fame, money, and everything that goes with that. He has no idea of anything else that would ground him with all of that action since that point. So he is not in any way going to be like anyone we know or associate with. And if he is nice it could be because he is actually nice (I mean say to hotel staff) or because when you are a celebrity you have to be nice or word gets out really fast. (Leona Helmsley).Look I remember when I sold my first small company at a young age. I wasn’t even super successful in any way. But I remember distinctly how I was treated on the day after the sale by 50% of the employees and pretty much 100% of the sales people. It was as if I didn’t matter anymore. Ironically Trump had a similar experience when he went through bankruptcy. I think in one of his books he related how a large percentage of people that he thought actually liked him all the sudden wanted nothing to do with him or didn’t fawn over him anymore because they didn’t stand to gain anything. But the people who actually liked him stuck around and still were friendly (or something like that).

        1. PhilipSugar

          If you look at that Loews the former Graves hotel, it had a lobby on the fourth floor. I go there enough, they had it roped off, he had a black curtain shutting off the bar. I didn’t care. They know me well enough they said I could come in…..don’t care.

  17. someone

    Just got back from Macca’s tour kickoff in Quebec City .You can remove “arguably” from your statement about him being the greatest living songwriter .And an amazing performer at 76!