Video Of The Week: Jerry Colonna on ThisWeekIn

Back in 1996, at the very start of Flatiron Partners, Jerry Colonna, who started Flatiron with me, introduced me to Jason Calacanis. We hired Jason to do some due diligence for us on a potential investment in Geocities. That's how I met Jason. We went on to buy the first ad in Jason's magazine, Silicon Alley Reporter. Jason and Jerry tell that story at the start of this interview.

The really good stuff happens later on when Jerry gets talking about the emotional side of startups and entrepreneurship. This is another long one, 90mins, but if you can find the time to watch it, I think you'll get a lot out of it.

I recommend fast forwarding to 4:40 so you can avoid all the sponsorship stuff. If you can't watch the whole thing, I would suggest the part between 55mins and 1:05mins. You'll see Jerry in action.

#VC & Technology

Comments (Archived):

  1. Rohan

    Shameless plug πŸ˜€ – For those who’d like a shorter Jerry interview with lots of awesomeness – do check out…@kidmercury – Hopefully you don’t think of a 25 minute interview as ‘doing a parker’ as well.

    1. awaldstein

      Nice one Rohan.Keep on plugging…

      1. Rohan

        Hehe. A touch of marketing doesn’t quite hurt, does it Arnold? πŸ˜€

        1. awaldstein

          Marketing is the connector. Without it I wouldn’t have know about the piece.As I’ve said a few time before–> Marketing matters…

    2. takingpitches

      Awesomeness Rohan!thanks for the transcript – well played

      1. Rohan

        Glad Ketan!

    3. kidmercury

      Lol a 25 minute video is totally pulling a parker! πŸ™‚ But sometimes pulling a parker is warranted, I must admit. I mean, not when you want to write a 9500 word essay on your lord of the rings themed wedding, but when you do a quality, educational video, sure. πŸ™‚

      1. Rohan

        Haha. Yeah, we tried doing shorter interviews but it never go to the ‘good stuff’ till about 15 mins. :-)And above 30 minutes really feels loooooong. πŸ˜€

    4. LE

      I’m going to go back and watch that.I like the fact that there is a transcript. I was able to read some of it and it piqued my interest in the rest.

      1. Rohan

        Glad! πŸ™‚ There’s other interesting ones too. Hehe

  2. jason wright

    i watched this yesterday. it’s not light viewing.

  3. awaldstein

    I need to come to grips with this ever popular long format. Tough for me.The first 90 minute piece I’m certain I”m watching today is the Israeli film, Fill the Void. Gonna Citi Bike it over to the Sunshine later.

    1. fredwilson

      Citibike to the SunshineTwo of my favorite things about NYCNice plan!

    2. ShanaC

      tell me what you think – looking for a date night movie

      1. awaldstein

        Plans changed, saw Man of Steel. Today’s plan may be tomorrows reality though.

  4. btrautsc

    love these interviews with jason… great for listening while getting stuff done

    1. jason wright

      yep. if you haven’t already seen it i recommend his interview with David Heinemeier Hansson (the first one from a couple of years ago – he came back recently for the sequel). great just for the entertainment value.David is a European.

      1. btrautsc

        he has a number of great ones. Sacca 2 part is great. Phil Libin,…he does a great job keeping a ridiculous high standard of quality.

        1. andyidsinga

          Sacca was great! … Salinger Group FTW!

  5. William Mougayar

    Jerry is amazing. He articulates the psychology of business so clearly. It’s that sixth sense that’s often neglected but will give you an edge.The last 20 mins are very powerful. No wonder Jason gave him a pass on the swear tinbox.

    1. jerrycolonna

      I was swearing? I hadn’t noticed. πŸ˜‰

      1. pointsnfigures

        If you are like me, sometimes it’s just a part of the vernacular. You probably come by it honestly. (for me, West side of Chicago, trading floor. F*&^ and its derivative becomes a noun, verb, preposition, simile, proper noun, term of affection, subject, predicate, modifier and emotion) And thanks, I got a blogpost out of your comments.

        1. jerrycolonna

          πŸ™‚ I’m like you. And when I’m with someone else from Brooklyn, it comes out even stronger.

          1. pointsnfigures

            nice reflection on your father. the stories I could tell.

      2. William Mougayar

        Jason didn’t even notice either.He typically has his guests put $10 in the jar each time they swear. Your being exempt was very telling. You had him hypnotized.

      3. Charlie Crystle

        really interesting format–the public session worked very well in this case…

  6. pointsnfigures

    I think it’s bullshit that people think 1995 was a long time ago : ). When people are “real” and you are interested in the topic, it’s compelling. A lot of cool stuff is in here. I am reminded of the person that said to randomly open the phone book and call someone and ask them their story.I love the fact Jerry said after Maslow’s first level of needs, people want to be connected. Seems like an investment thesis!

  7. Charlie Crystle

    “just take a breath…I’m gonna get all coachy on you…I just want to honor that”Thanks to both Jason and Jerry–so very generous to do a public session. It’s taking me back to November 2008…

    1. fredwilson

      That’s what it was

  8. Thomas Ilk

    These sponsorships you recommend to avoid make it possible for us all to watch this great interview and the countless of other great episodes on Jason’s show.Some marketing people will read your recommendation and use it as “evidence” that people skip these ads anyway. It won’t affect Jason’s show, since it’s so immensely popular, but it might make it harder for smaller shows to get to where Jason’s show is now.If everybody would link to podcasts with instructions on how to avoid the sponsorships, there would be no shows to link to.

    1. fredwilson

      There is a better way to promote the sponsors than to make we wait for almost five minutes before i get to the content. In fact he is doing a disservice to his sponsors by doing that. It makes me hate Scott Walker and I have never met him. Really bad marketing/branding

      1. pointsnfigures

        I like better for attorney help.

      2. Thomas Ilk

        Edit: It seems I’ve misunderstood your comment. I agree that it’s not a good idea to do the sponsorships at the beginning of the show.My old comment (I thought you meant changing the whole form of advertising on the show):I agree, but that doesn’t change the fact that this form of advertising pays the bills for shows like this.Jason without a doubt could change the form of advertising on the show, but most smaller shows don’t have the influence to get advertisers to try forms that aren’t “standard”.I know this personally, since I am starting a online magazine right now and decided to not do banners & co which still finance most online publications. Especially in the beginning this is an enormous obstacle despite us offering alternatives that are far superior. Agencies & clients are very resistant to change and different forms of advertising since they often involve more work on their side and have no proven track record. It takes a long time and bigger scale to convince them.One example is Buzzfeed which has “invented” some new forms of advertising. (I personally hate them, but marketers love them now) Now with scale they can make them work, but in the beginning sure as hell they could have made more money with banners. They decided not to and had enough VC capital to get to scale before running out of money. Most small publications & podcasts don’t and need to make as much money as soon as possible.I personally play the long game and bet on new forms that I am convinced of, but I’ll never judge people who do classic banners & sponsorships because I know how expensive media is and how hard it is to get money from clients without offering standard banners & sponsorships.

      3. Dale Allyn

        I agree, Fred. Much better to start right in. There are lots of ways to bring sponsors into the “conversation” in a way which really presents the sponsor in a meaningful, and even regal way. User Experience is everything and this is no exception.I get Thomas’ concerns, but better to reconfigure to best ensure the desired outcome.

        1. fredwilson

          exactlyi like the way Howard Stern did it when he was on terrestrial radio

        2. Thomas Ilk

          As I’ve written in my first response to Fred’s comment most small media companies can’t afford to optimize for user experience when it comes to advertising.You have to play the long game and have lots of financial standing power to get to the scale where you can get advertisers to do “non standard” forms of advertising.Especially in the early stages of a media product you leave lots of money on the table if you decide to not do f.e. banner ads.I personally play the long game, but I would never judge people who can’t do it and have no other choice than doing “standard” advertising in order to finance their company.Jason of course could find other ways, but even at his scale it probably wouldn’t be a wise financial decision.I agree that putting the sponsorship read upfront is a bad idea and that Jason could do the sponsorship reads in a better way.

          1. Dale Allyn

            Thomas, I certainly am not suggesting the sponsorship or advertising has no place. It’s a valid monetization model, but there are many ways to execute it. I appreciate your points of view, but I’ll stick by my assertion that user experience is everything. One can and should look to the details of the entire presentation to achieve the desired outcome. Boring or even angering visitors is not a great model for getting “glue”.Your last sentence does clarify that we agree that sponsorship shouldn’t be bulked up front. Today, we see many programs go straight to the program to ensure hooking the visitor, then bringing the sponsor into the “conversation”, which can be done in many ways if one thinks a bit outside the box. And visual signaling can be provided without interrupting as well. There’s “costly” and there’s “lazy” – both can and should be avoided. :)(edit: typos)

          2. Thomas Ilk

            Agreed.Don’t get me wrong, I am a perfectionist when it comes to user experience. I am just saying some people have to make trade-offs when it comes to advertising in order to finance their media project.It’s the same problem Tumblr, Facebook, Foursquare & co are having on a big scale. Inventing ad forms, that add to the user experience, do work for advertisers and produce enough revenue, is one of the hardest problems.

          3. Dale Allyn

            Agreed, Thomas. I think most here would agree, but still suggest that taking care to balance such things, using non-intrucive sponsorship whenever possible, choosing timing so that the visitor stays for the ad content and sticks around for the continuing content, etc. are essential. It’s “blunt” vs. “sophisticated” regardless of budget.

      4. jason wright

        Scott Walker has been sponsoring for quite some time. it must be working for him. he’s servicing the scrappers.i think the production values of the show probably attract scrappers. not too slick is sometimes a good thing. it’s an empathy thing

      5. jasoncalacanis

        Maybe I should load them back a little…

        1. fredwilson

          Do it like Howard Stern. Do on air promotion

          1. pointsnfigures

            Or the old Paul Harvey or how Rush Limbaugh does it. Seamlessly into the show. Listeners don’t even know they are being pitched

          2. fredwilson


          3. LE

            It’s interesting how people never get a chance to give criticism to people when they know them in person (everyone wants to have smoke blow up their ass and told how perfect what they did was or they get insulted if you don’t like what they did and don’t give it kudos).But in a forum such as this all the critique will allow Jason to greatly improve his show and provide better value to his advertisers. What a favor you’ve done him with one simple comment.What’s also good is that you are so open to criticism and learning from it.On hacker news Paul Graham is totally detached from reality you can’t (easily) say anything against him or he gets defensive (and besides you get crapped on by the fawnees and sycophants) who just blindly follow anything he says.

          4. Dale Allyn

            This is the way. Weave it in tastefully, add some occasional visuals, respect the sponsor and the viewer/listener.

          5. jasoncalacanis

            That is actually the format of the ads, just not the remote show because we don’t know when they air, and the advertising is all scheduled and ads change based on the week by sponsor.Which goes back to the cost of doing all this…. The cogent business really doesn’t scale very well most of the time. πŸ™‚

          6. James Ferguson @kWIQly

            I have little patience for ads, but for this quality of content I am happy to suffer a little.I think you and Jerry just enriched the life of many an entrepreneur a little – well played.

          7. jerrycolonna

            Wait. What’s everyone talking about? There were ads?;)

          8. jason wright

            what doesn’t work is your clothing. popping up in the ads slots in different clothing just kills the continuity vibe stone dead. you need an on-screen wardrobe carefully selected by Albert Einstein.

          9. LE

            To this day I remember some of those advertisers when Stern rolled out in Philly in the 80’s. Those were great ads. And you didn’t mind them either. I remember one time when he interspersed an advertiser over 30 minutes.I remember when he called Domenick Barbera a shiester. Turned out to be true.

        2. Guest

          Preroll ads are a total #fail.The reason?They suck, there’s zero value for the viewer.That’s discrespect.Why be disrespectful?Jason, what about innovating?Just a thought.Need an innovation?The answer is right under our collective noses, email me if you don’t see it. It’s a freebie for you, a small thanks for the years of your fun reportage.

    2. William Mougayar

      The way that Jason pushes his sponsors is frankly nauseating and un-conventional. As a regular listener to his episodes, it’s the thing I despise. There are better ways to acknowledge/promote sponsors that are less in your face. I’m not sure why he doesn’t tone it down a bit. I find it hard to believe that he uses all the services that he promotes when he says they do. It doesn’t come across as genuine.

  9. Dave Pinsen

    I watched that ten minute stretch you highlighted, plus a bit more. Compelling stuff. I remember the day my father list his job too. Felt a pit in my stomach then and I was about the same age as Jason when it happened.

  10. James Ferguson @kWIQly

    Thanks Fred,I used to think “coaching – not needed here”. How wrong I was – this struck many cords… The section regards fathers at 0:55 literally brought tears to my eyes.And so respect for Jason and JerryMy father also “Never Recovered” – My mum took his wristwatch off his body and handed it to me saying “its yours now – he doesn’t need to worry anymore – and now its ticking” or something similar.I founded my first company two weeks later. We have seen ups and downs – and fear of losing it remains and must not hold you back.When I hit rock bottom I lost that watch – but we kept going – we never went under, we paid our debts and now we are growing. So I hope I will always be cautious about taking someone’s money without knowing how to pay it back. Playing for keeps is a tough game.

    1. William Mougayar

      Touching story. Jerry has a way to bring that out.

      1. James Ferguson @kWIQly

        Thanks – and clearly he has!The caution I mentioned was a part of my private answer to you about how long its taking – I think a well rooted business where founders have the right intents (and preparedness to delegate to young blood) is key to any successful story. In the sense that a great teacher is surpassed by his pupils – companies should ideally be handed off in the same way.The other differentiator is that sons/daughters of tried (and failed ) entrepreneurs tend to reject nepotism and believe in meritocracy because even their parents as “guiding lights” have been seen to make mistakes.

        1. jerrycolonna


    2. jerrycolonna

      James…thanks for that. The image is powerful. And as complicated as my relationship to my father was/is, I just remembered I still have his watch.

  11. Charlie Crystle

    I usually don’t double-post, but this was really enjoyable and fulfilling to watch.Founders, go forth and watch.And don’t skip the sponsor messages–that’s what pays the bills.

    1. fredwilson

      i appreciate the sentiment about not skipping the ads.but in this case, exactly what are the bills?jerry’s not getting paid for his appearance.i did one of these with Jason. it’s shot on one camera.there are really no costs here.what you are paying is Jason

      1. Charlie Crystle

        Well yes, ok, valid grass-fed free-range beef. I’m feeling sentimental about the spot.The format is wrong and unnecessary, which I’m guessing he knows. I was just so touched by the piece I wanted to tip.Maybe Jason could skip the long intro, replace with occasional 15 sec live spots during interviews, and supplementing with signs, or a wrapped screen with non-moving type? Or screw the $ and just do the show? @jasoncalacanis

        1. LE

          “Or screw the $ and just do the show?”Oh come on Charlie, that’s easy for you to say.Your other suggestions are good though. This can be fixed by Spicolli’s father’s tool box.

          1. Charlie Crystle

            Just about everything is easy for me to say πŸ™‚

      2. Thomas Ilk

        Edit: Jason just answered and I’ve overestimated the full time employees a little bit. There are three people working on it full time.Fred you massively underestimate the cost of producing a high quality podcast. As far as I know there are at least 5-6 people working on This Week in startups. Audio engineering, producers, sales people,…

        1. fredwilson

          I doubt it

          1. Thomas Ilk

            I don’t know if you have any experience in the media space, but it’s typical for tech people to underestimate the costs massively. Content is incredibly expensive if done well.

          2. fredwilson

            I have lost tens of millions of dollars I’m the content space. I will never ever invest in content again

          3. Thomas Ilk

            I completely understand. From a financial point of view there is almost no reason to do a content company. It’s harder, more expensive, takes longer to scale and produces less returns (although they arguably produce returns with a higher probability than almost any other sector if equipped with the right team and enough financial power).I love the space. It’s not a winner takes all market and if done well there’s almost no way it won’t be at least a medium success. There’s far less luck involved and only the best get to the top.Furthermore, it’s ripe for disruption. No one has figured the business model of the future yet. Buzzfeed thinks it has, but I completely disagree.The infrastructure age of the internet is over and the application layer has been built. As history has shown content will be next and will produce the biggest returns in the long term.I’ll prove it to you πŸ˜‰

          4. Thomas Ilk

            Lerer Venture, Chris Sacca & co who’ve started investing in content will hugely succeed in the next decade.

          5. fredwilson

            I wish them well. But I will not join them professionally. Maybe personally through my wife’s activities

          6. timrpeterson

            whats twitter, tumblr, disqus, soundcloud, etc.?

          7. Thomas Ilk

            User generated media is from a business point of view not comparable to real content companies.

          8. timrpeterson

            soundcloud, zynga, etc.

          9. Thomas Ilk

            Sorry I don’t get the point you are trying to make. Care to expand? πŸ™‚

          10. timrpeterson

            soundcloud, zynga and others are content companies,user-generated vs. company-generated content/media is a fake divide, both serve ads up to the point where users balk

          11. Charlie Crystle

            soundcloud is a platform company, not a content company. Zynga missed an opportunity to be a platform company.

          12. timrpeterson

            platform and content are just word choice,by your definition nobody is a content company

          13. Charlie Crystle

            that’s not true at all, and I didn’t give a definition.Soundcloud is a platform companyhttp://developers.soundclou…Twitter is a platform it looks like Zynga’s trying too…

          14. timrpeterson

            cmon name a content company…exactly you can’t because your+Fred’s+disciples’ (implicit) definition of platform covers the entire internet which brings back to original point that this is a fake distinction not worth discussing

          15. Charlie Crystle

            CNN is a content company.You’re making vacuous (and inaccurate) arguments. Explicitly: a platform gives developers access to both data and functions for the purpose of building new things (or old, whatever).Content: this comment is content. It’s not a platform. It doesn’t give any developer any functions they can use to build new things.(waiting for dismissive response in 3…2…1…)

          16. ShanaC

            no you get local moderator going *eyeroll*@timrpeterson:disqusstill I think what is content and who produces it is a really interesting question

          17. Charlie Crystle

            and what’s your answer?

          18. timrpeterson

            why eyeroll, it doesn’t make sense to say you don’t invest in content and then in fact invest in content,next there is some distinction about who produces the content and then when its pointed out Fred invests in content produced by anyone, users (twitter)/non-users (soundcloud), I get some soliloquy about “I know what works and makes people lots of money” which is totally irrelevant and the real eyeroll scenario

          19. timrpeterson

            companies like CNN don’t happen anymore precisely because of the internet so yeah again talking about content companies is pointlessregardless even lame-ass CNN would prefer to be called a platform company, its just their platform sucks:,…again this is all just fake taxonomy bs

          20. Charlie Crystle

            So your argument is that everything on the internet is the internet, and there’s no distinction in functionality? Twilio is Gawker is Node is Pandora is Stripe?Where’s Oscar Wilde when needed…

          21. timrpeterson

            wtf are you talking about functionality

          22. Charlie Crystle

            thanks for this–now I completely understand.

          23. fredwilson

            Vox Media is a content company

          24. Vineeth Kariappa

            huffpo, techcrunch, gigaom,bbcworld, yahoo, msn…

          25. fredwilson

            Platforms for content but not content businesses themselves

          26. timrpeterson

            fake distinction

          27. fredwilson

            Maybe in your book but certainly not in mine. I have invested in companies that create content and lost tens of millions of my investor’s money. I have invested in platforms for content creators and have made hundreds of millions, probably several billion, for my investors when it is all said and done. I know what works for me and what doesn’t

          28. timrpeterson

            irrelevant,point is “content businesses” dont exist anymore only because now people call it “platform for content”,

          29. fredwilson

            They do. A content business is when you pay to produce content as Jason does with these videos. A platform is a when others put their content on your service and you don’t have to pay them to do that

          30. timrpeterson

            overly literal, the vast majority is the latter,maybe in 2003 if you would have said “I won’t invest in bricks and mortar company X, e.g., Blockbuster” but its 2013 so this line of thinking and the examples you point out (Jason, Voxmedia) are pretty self-evident/marginalized nowbtw thanks for posting this video, hadn’t heard of Jerry Colonna, watched whole thing, seems like really cool/thoughtful guy,

          31. jerrycolonna

            πŸ™‚ Thanks.

          32. David Semeria

            Fred’s last reply worked for me.Perhaps it was the word “billions” that swung it.

          33. timrpeterson

            Its fine to say “I know what works for me”, but its kinda dumb to say “I know what works for me and its X and not Y” when its just as much Y as it is X.Its better to just keep it abstract and say “I know what I like when I see it.”

          34. Steven Kane

            popping up again to ask again — dont the returns from zynga (not to mention yoyodyne and gamesville and star media and others) make your portfolio of “content deals” an overall positive return? even a huge positive return? not sure why you have an axe to grind re content deals — unless i’m mistaken (always a possibility) overall they have been very good to you and your LPs?

          35. fredwilson

            i think its the exception that proves the rule

          36. Charlie Crystle

            not at all. there’s a huge difference between content and the tools and platforms that produce and distribute them.

          37. jason wright

            they’re enabling. the content is generated by the users, as you know. cost transfer, and yet users often still typically don’t own their content. the utter bare faced cheek of it!.

          38. Steven Kane

            given the returns from zynga alone, overall haven’t you made money in the content space?

          39. fredwilson

            Zynga is the only content company we have invested in at USV and I was somewhat uncomfortable with that investment because of that. It’s a hits business and they have had a dry spell for several years now and look where the stock isWe invested when Mark took a flash based Texas Holdem poker game and put it onto Facebook. That seemed like a smart move that was likely to create a lot of value. And it did. I was hoping they would turn that into a games platform for social media. But instead they built a games studio. That’s fine and we did well with it but it was not something that USV feels comfortable doing

          40. Steven Kane

            thats extremely interesting stuff – would make a great blog post in and of itself! to wit, what is the difference between a “games platform for social media” and a “games studio”? did you and other investors and directors and advisors advise zynga and pincus that he was veering off in the wrong direction (despite the amazing success of mafia wars, farmville, cityville et al)? if not, why not? what was zynga’s/pincus’s response? do you believe the current low share price is reflective of the company being a “games studio”? why is zynga getting beat up for that when other content companies like CBS and TimeWarner are not? etc.but, ahem. you dodged my wrote “I have lost tens of millions of dollars I’m the content space. I will never ever invest in content again.”i don’t think thats true. so I asked: given the returns from zynga alone, overall haven’t you made money in the content space?i daresay the answer is a resounding, humungous-dollar-value “yes.” (as you know i have some visibility into what IRR and absolute dollars early investors in zynga have received, even at $2/share today.)so… in several decades of VC investing, across all your content investments, have you “lost tens of millions of dollars”? or perhaps made hundreds of millions?sorry, cant help myself — i am a film school brat and content creation addict!

          41. ShanaC

            probably overdue – what should content companies look like,in light that content producers need to pay their bills, is super interesting

          42. ShanaC


          43. fredwilson

            No to retailingYes to marketplaces

          44. LE

            When you are an artist and you want something to come out right you spend much time thinking and planning to make things “perfect” because there is a sense of pride to what you do.Perhaps parent comment is off by the amount of people involved but doesn’t detract from the point that if you are trying to make something good and professional and are covering various contingencies there is much to plan for and do.If you are willing to take your chances and produce content that isn’t professional of course there are many many things you can cut back on.

        2. Vineeth Kariappa

          Buy a mac.

      3. jasoncalacanis

        Actually Fred, There are three full time folks working on the show. And we have a studio, and I don’t personally take any money from the show. 100% goes back into the show/staff.We do 100+ episodes a year, so we need a ft producer, tech and sales exec. Getting a guest like jerry might represent a week of work, flying a tech across the country, etc.But, you can skip the ads at the start.. You’ll eventually love the program so much you’ll tweet the sponsors name and say thanks.

        1. LE

          “Getting a guest like jerry”Interesting that as the level of professionalism goes up the amount of time spent goes up, say, exponentially.(Rohan inteviewed Jerry as well I’m sure he didn’t spend that kind of time, right?)This doesn’t mean I don’t agree I actually agree with what you are saying.As someone who just spent my time to edit down some wedding videos that I shot of a relatives wedding and post to a (paid) vimeo account everything takes time. How long should the music fade in be? How much time to spend on the titles? Where to put the titles and credits (my “ad” was my name and a Β© symbol). Not to mention having to watch the same clips numerous times. Not to mention the camera time. Not to mention having backup batteries and equipment and…Now if I just wanted to show up, shoot, (take my chances) and give them the raw footage it would have been a breeze.

          1. Thomas Ilk

            I completely agree. People completely underestimate the level of work needed to get every detail right and produce content professionally.

          2. LE

            Back when I used to do photography for my dad’s wholesale catalog he knew how much time I spent in the darkroom as well as developing the film and shooting because I did most of it in the basement. Hours and hours.His partner (my uncle) had no clue and thought I was charging to much for the photos I’m sure (even though they used to use a professional photographer to do the same).

        2. fredwilson

          I love the show but really hate the way you throw the sponsors in my face. In all my years of posting video to AVC I don’t think I have ever said “skip the ads”I had to this morning because they are so god damn offensive. I now have a terrible opinion of Scott Walker and I’ve never met him.You need to find a more elegant and sophisticated way of doing this

          1. LE

            Wow. I’m now going to watch just to see the ads and see what you found so annoying.

          2. LE

            Ok I watched the preroll (or whatever it’s called). 3 ads?Totally appropriate and not annoying at all.Annoying is when you want to watch a video on and it’s about some tragedy and there is a A&P commercial with happy music that last 30 seconds.These were quick and to the point.Just timed them 22 seconds for all three. Seemed like much shorter because of the tempo of the announcer and the fact that there were three.Only change I would make is put the walker law logo higher because it’s blocked by the control bar at the bottom if your mouse is in the frame.Jason should also have something so if you forget the sponsors you can find out the sponsors.

          3. fredwilson

            Did you notice that after those three prerolls, he talks for about 30seconds and then you have to watch another minute or two of ads?

          4. LE

            Ooops!I just saw another of your comments and went back and scrolled forward.Reminds me of a PBS “beg a thon”.Sorry I don’t normally go off half cocked like that. I was wrong.

          5. LE

            Just also skipped to the same for sharefile.Big failure also is Jason looking down at notes while he is talking and “ticking” off points. Could use a teleprompter for that. [1]All said there is a way to fix this situation and achieve what Jason needs in sponsorships without being annoying. (Even a logo at the bottom would be less intrusive.)[1] Here is an ipad teleprompter:

          6. Charlie Crystle

            there are iPad teleprompter apps btw…

          7. jasoncalacanis

            Fred is right, we should start with content then do an ad read later… This is a little too front loaded. Will reoptimize it.Fred Is wrong that you’re paying me and there is no cost. There is a ton of cost to doing this consistently.

          8. LE

            What do sponsorships cost?I’m not seeing anything here:http://twistartups.wpengine…And the wpengine site seems to be stalling. So I can’t find out more info.

          9. Dale Allyn

            Even better than “reading an ad” would be weaving appreciation for the sponsorship into the conversation. A bit less jarring, especially considering that you’ll not be working with “Pepsi’s budget” – and it can come off as sincere if done with natural comfort.I enjoy the interviews and look forward to the format mods.(edit: left out “not”)

          10. fredwilson

            Yes. That’s how I try to pimp our portfolio companies. By turning them into case studies. As was pointed out in the top comment the other day to my valuation vs ownership post, this blog carries a lot of advertising

          11. Dale Allyn

            Right, Fred. I find it apparent, yet not off-putting. And there are usually some good discussions which strike off from it. Business is business, but it needn’t hurt. πŸ˜‰ Done right, it can make customers (i.e. sponsors or entrepreneurs) flock to you.

          12. Donna Brewington White

            I would be disappointed if he didn’t pimp his portfolio — disappointed for them but also because USV happens to have some fascinating companies.. Plus, they tend to invest at the cusp so their investments often point to what’s coming down the pike.

          13. Dale Allyn

            I completely agree, Donna. I respect and admire @fredwilson:disqus for how much he supports his portfolio companies. And I very often learn something new about these and other brands from his style of “marketing”. I like it.

          14. btrautsc

            this is what I was thinking. I watch all the time. I skip every ad (no offense Jason)…It would be incredibly easy to weave in the New Relic spot, some of the others could prove a little more tricky though.

          15. fredwilson

            Thanks for clarifying that Jason. I am still not sure why you need all those people. The one we did at USV was you, me, and a single camera

          16. jasoncalacanis

            We do 2-4 episodes a week. That’s 2-5 hours of content a week, and 3-6 guests. That means a never ending research and invitation process, preproduction, post production and sponsor support. Booking guests is almost a full time job… It took me 2 years of emailing you to setup the show–you just don’t remember all of the back and forth! πŸ™‚

          17. fredwilson

            OK. I get it

          18. Donna Brewington White

            You should have a talk show. You would be great at this.Maybe you can work the word “brevity” into the title. Or maybe something along the lines of “straight to the point” or “cut the crap” etc.

          19. Vineeth Kariappa

            You get paid by youtube!

          20. andyidsinga

            Jason, would love to see TWiST jacked …ala…rock on, your shows and staff are awesome

          21. William Mougayar

            FlipBoard is doing native advertising elegantly. As you flip, you see a simple Delta ad about their new large seats that are more comfortable for sleeping, then if you click on the ad, it points to some credibile articles from reputable publications about the benefits of sleep. That’s a smart linkage.

          22. Vineeth Kariappa

            This is not native adverts. This is “in your face” adverts.

          23. William Mougayar

            But it’s native to the platform and in a format that espouses the content itself. It’s rather cute I thought. I prefer to get delayed by 2 secs here and there, and not have to pay FlipBoard a subscription fee. It’s really minimally obtrusive. I don’t think you can go lower than that.

          24. Vineeth Kariappa

            Native for this format would have been an advert in the background n “no special mention”. It sounds like an advert for “save kids dying in africa, please donate”

          25. jason wright

            what did Ogilvy say?

          26. William Mougayar


          27. Scott Edward Walker

            Sorry to hear this, Fred. I’m a big fan of yours, and I try to support shows like This Week in Startups and Mixergy because I think the interviews add extraordinary value to the startup community. Indeed, I love what Jason Calacanis and Andrew Warner are doing, and I am proud tosponsor their shows. To say that you β€œnow have a terrible opinion of [me]” is disappointing, at best.I worked for nearly eight years at two major law firms in New York City, and I saw that for many entrepreneurs and startups the big-firm template just doesn’t work. Not only are the fees through the roof, but also startups often getassigned to young associates with little or no experience. Accordingly, in 2005 I moved to California to launch my own law firm with a new business model geared specifically to entrepreneurs and startups.I would love it if guys like you would support guys like me trying to disrupt the β€œold boys club” legal profession and helpentrepreneurs and startups. Thank you.

          28. Thomas Ilk

            I am an avid viewer of This Week In Startups and have seen Jason read your ad many times. Before them I didn’t know about you, but now if I ever move to the Valley you’d be the first lawyer I’d think of.I love your support of the show and the concept of fixed fees, since I’ve had my share of surprisingly high invoices by lawyers in my first startup.

          29. Scott Edward Walker

            Thanks Thomas – much appreciated. As I always say, “billable hours reward inefficiency.” Please note, moreover, that we represent startups all over the country – everything is done via email and phone. Cheers, Scott

          30. Thomas Ilk

            I live and work in Austria, but I’ll contact you as soon as my current startup expands to the US. If all goes well, we’ll have an office in the US in 2 years.

          31. Scott Edward Walker

            Sounds good. Btw, we just helped a guy in Austria set-up his Delaware C corp. We have a fixed-fee “Startup Package” that takes care of everything (including vesting, IP issues, etc.).

          32. Thomas Ilk

            Yep, lots of Austrian founders set up a C Corp or UK Ltd as a holding company for a local “Gmbh”. Unfortunately “GmbH” and other Austrian corporations are not well suited for international investors and concepts like vesting.

          33. James Ferguson @kWIQly

            OK – your response to Fred made me think – so I should give this ad of yours fair run. So I looked at your ad just now.Its clear Jason “must say” N-things to cover the fee – imagine the impact if when you kissed a girl at highschool you took out a “base-checking list” and said Ok – Now second base – “I think your eyes …) – That’s how you are making jason look ! He is a natural – let him beTL;DR Dont waste everyone’s life – you are probably doing a great job but less is more (like energy savings)30 seconds might get better response ratesEdited (removed comment which offended)

          34. Thomas Ilk

            You maybe should think about your last sentence again and consider editing it. Suicide is nothing to joke about and you never know if you adress someone who had a friend or family member commit suicide.

          35. James Ferguson @kWIQly

            Thanks Thomas – Actually I am in that situation , (and make light of it sometimes – black humour can be a defense) but I do take your point and have edited – Thanks again

          36. Scott Edward Walker

            Thanks for the input, James. I love the term Nietzsche uses: “perspectivism.” Of course the ad is over the top – that’s what it’s designed to be. Cheers!

          37. James Ferguson @kWIQly

            Ah OK – I think irony is great when I get it (when I don’t I feel like an ass) – Do you think most people get it ? It seems Fred didn`t and there is a mixed reaction

          38. Scott Edward Walker

            Agreed – seems to have struck a raw chord with Fred and others. I’m checking out now. I wanted to relax today after a long week of negotiating a couple of difficult deals. Thanks

          39. James Ferguson @kWIQly

            Cool – We are a European Startup with some possible US interest down the line – will bear you in mind when it happens

          40. Charlie Crystle

            go relax. fix the ads on monday (apparently you haven’t watched the interview!)

          41. Donna Brewington White


          42. awaldstein

            In your face is always bad marketing in my opinion.The fact that you are doing something interesting has nothing to do with the tolerance you should expect from viewers in how you advertise it.People don’t embrace need, they embrace value. There’s a better way to present it.

          43. Scott Edward Walker

            Thank you for your input. I’ve been supporting Jason’s shows for more than two years now, and most of the responses have been very positive. Perhaps I’m detecting a bit of an East Coast vs. West Coast thing here.

          44. awaldstein

            Don’t know about the coastal thing but great attorneys that can adopt their practices to the needs of the startup community are worth knowing about.My point is just that old school methods to market innovation feels discordant.

          45. Scott Edward Walker

            Thanks, but I don’t view integrated marketing as old school.

          46. awaldstein

            Each to their own.Whenever you provide content out of whack with when the customer is open to receive it, is not optimal, integrated or not.

          47. fredwilson

            East coast vs West coast?????????That’s ridiculous

          48. Scott Edward Walker

            Wow – this is getting like the comments on Hacker News :)… Maybe NYC vs LA is more accurate — I lived in Manhattan for 10 years and Los Angeles for 7 years. (Have you ever lived outside the NYC area?)

          49. fredwilson

            Yup. I have lived all over the world. I moved fifteen times before I was 16

          50. Scott Edward Walker

            Cool – thanks again for your feedback, Fred. Maybe we can grab a cup of coffee sometime – I live in SF now. Take care, Scott

          51. btrautsc

            what a BA response. I felt like I was reading a Jack Reacher novel for a second.

          52. jason wright

            tethereddoes that count?

          53. pointsnfigures

            how did that help you as an investor?

          54. andyidsinga

            that is ridiculous. what isn’t ridiculous is that seattle can go straight to hades!! #rctid #baon:):):)

          55. Donna Brewington White

            It may be more of an AVC thing. Iron sharpening iron and all that.

          56. fredwilson

            Please don’t take it personally. I was just making a point about how Jason is hurting your reputation with me by running the advertising the way he does. I like that you stopped by to participate in this convo so all the negativity from the ads is now erased and then some!

          57. Scott Edward Walker

            Thanks Fred – not taking it personally at all. This is obviously your perspective, and I respect you. I will definitely discuss this issue with Jason. Cheers, Scott

          58. Tereza

            This is such a valuable discussion and one I think about a lot these days. These forums are critical to the ecosystem — and they cost money. It’s so broken. No sponsor wants to know the audience is rolling their eyes. Thing is, we’re stepping into a phase where sponsorship ROI is getting scrutinized. “Branding to support the ecosystem” is noble but when we’re literally held in contempt, there is a fundamental problem. There is so much logo and event fatigue. I promise you if logos dropped off a bunch of mastheads, no one would notice.I feel like it would be more honest if it said, “This video was made possible by the $5-figure support of Scott Walker.” People need to know who’s buttering the bread.Or, make a QUICK (<1 min) vid where jasoncalacanis intros @scott on-camera and Scott says — “I work with 100s of entrepreneurs in my legal work. I see them suffer. And I’ve seen great benefit through working with great coaches like Jerry Colonna. We’re committed to helping you to win and living a good life — and so it’s our pleasure to bring Jerry to you.” Audience gets to know Scott Edward Walker and his pro-entrepreneur vibe.But — that’s only a quick fix. This ecosystem sponsorship thingy is broken + we need more win/win options.

          59. Matt A. Myers

            Perfect! Quick, short, engaging (see a face and hear a person), personal message that’s specifically relevant to the context and content the viewer is about to watch – or is in middle of watching – or has finished watching.@scottedwardwalker:disqus and @jasoncalacanis:disqus should see about making this happen in future. I think @fredwilson:disqus would agree this format is much more appealing, and attractive even.

          60. Robert Holtz

            Fred, I’m a big fan of Jason’s and he’ll forgive me for pointing this out here but don’t let up on your assertions about the ads so quickly.The delivery IS heavy-handed.Clearly there is a way to do this ad placement without sounding like a televangelist, used car salesman, and a rodeo auctioneer all rolled into one. I quote: “Let’s just take a pause for the cause, spread some honey to make the money!” That has all the subtlety of a barreling freight train.The public understands ad-supported content but the delivery here really detracts from the overall perceived quality of not only the content but also of the source. And that is for me who is already a fan of Jason, of Launch, of you Fred, and of Jerry Colonna.Jason, in all candor and support of your ongoing success, Fred is absolutely right and you really should consider his advise. A more understated delivery really will improve on the entire package. And consider that if the ad spots AREN’T over the top, no one needs to advise others to “skip the ads” — everyone would see every ad impression and those impressions will be positive.

          61. Vineeth Kariappa

            You really have to work on your sales pitch. It came off like, “My services are cheaper”

          62. Donna Brewington White

            I saw the ad roll after reading some of the comments so was expecting it to be worse than it is. Although I agree it could be done with more brevity and that would perhaps also give it more punch.I appreciate your approach. I left a retained executive search firm a few years back for similar reasons. We were priced outside of the community I had a passion for (startups) and our approach was too cumbersome and not nimble enough — with no desire or intention to change that. Otherwise a great firm.Breaking into working with startups is hard, though. Clearly, it requires creating a model that really works for their needs while also allows you to earn a living. I am constantly tweaking that balance.I respect that you have been able to do that. Some day I’d love to take you to lunch and hear more about your approach — and some of the companies I help may benefit from knowing about you. Thanks to Jason I know where to find you. πŸ˜‰

          63. jason wright

            Scott, go read of a copy of The Anatomy of Buzz by Emanuel Rosen. i feel sure Fred and Jason have. Ask if you can borrow the copy they share.please come back in a couple of months to report the spike in interest in your services.native advertising works.

          64. Andrew Warner

            @scottedwardwalker:disqus, thank you for supporting my interviews. I don’t just mean the sponsorship, but the help you’ve given me over the years.

          65. Scott Edward Walker

            Thanks Andrew – and keep up the great work

          66. Rob Sobers

            I’ve to say, as a viewer the show’s target demographic, I disagree.If I compare Jason’s ad reads to, say, a radio host (like Mike & Mike on ESPN), Jason’s endorsements sound more real, like he *actually* uses the products or services (whether he does or not). Not just reading a script. I really like it and rarely skip them.

          67. C Vo

            I actually appreciate @fredwilson honest opinion here. If Anything, he does @jasoncalacanis and @walker a favor. It was pretty tacky the way @jason promotes Walker firm. Take it constructively and you will have a home run. You will be the cool guys again. Tkx for stopping by to address it @walker

          68. matthewmclean

            It appears that Jason, Fred, and Scott all have a different problem. I intend to go out into this beautiful morning and fix all three. Thanks Jerry.

        3. ShanaC

          you should not go through the sponsors at the beginning at the end. intersperse them

        4. Richard

          You mentioned that almost went into film production. Why not do a Rolling Credits at the end of the clip?

        5. Charlie Crystle

          how about a different ad format?

        6. Matt A. Myers

          I’d like to support what you’re doing further – and looked to see if you were on – though it says you’re unavailable? πŸ™‚

      4. ShanaC

        equipment, editing.

    2. awaldstein

      To push on you my friend.Not on the value of the video, but on somehow our responsibility to support advertising by watching it.It is not the users/viewers job to listen to the sponsors messages. It’s the sponsor’s job to make them palatable and useful.I really don’t like advertising/infomercial based content. My personal opinion. I’d much rather subscribe.

      1. Charlie Crystle

        I agreed elsewhere. At the time of my post I was just really happy with the discussion that I wanted to be supportive. Now I want a better model and some ibuprofen.

        1. awaldstein

          ;)I jumped in in the early morning and now for a sec so didn’t see your other posts. . Don’t have a lot of time lately.

          1. Charlie Crystle

            what, you don’t read my every word? πŸ™‚

          2. awaldstein

            Sorry oh Yoda!

  12. Donna Brewington White

    If there is anyone on this planet I will listen to for 90 minutes it’s Jerry Colonna.On my weekend list. Can’t wait.

  13. Merten Wulfert

    My favorite quote from Jerry talking about successful entrepreneurs:”As smart as they are – and they’re wicked smart – and as hard-working as they are – and they work their tail off – there’s also a bit of luck. And the randomness of luck is really unsettling, because it implies a kind of uncertainty that scares the crap out of people. […] And that is life.”

    1. ShanaC

      maybe it is because of all the stories I’ve heard, but luck is everpresent.

    2. jerrycolonna

      Thanks. BTW, I think the randomness of life is both unsettling and hugely interesting–maybe even entertaining.

      1. Anne Libby

        Or playful…

      2. Steven Kane

        randomness? of life? πŸ˜‰

  14. Khalid Halim

    Thank you Fred for highlighting this interview. It is so valuable to so many startup founders who feel alone in their feelings of fear and doubt, as if they are the only ones feeling it. Thank you Jerry for demonstrating what great coaching looks like and how it can serve a deeper purpose than just giving advice or strategy (a misconception many have about what coaching is). Coaching can connect you deeply to your purpose, which is in the end why a founder started this crazy journey in the first place. Deep gratitude and thanks.

    1. jerrycolonna

      You’re welcome Khalid.

      1. pointsnfigures

        If it’s a good coach. I have run into “coaches” and all they tried to do was upsell me on services….. Jerry doesn’t strike me as that kind of guy.

      2. Donna Brewington White

        Thank you for all that you are doing Jerry to help entrepreneurs feel “less alone.”

  15. Matt A. Myers

    55m-1:05; Better, more inspired. Almost started bawling a few times watching – unfortunately stopped myself because I’m in a cafe. For me, it’s a bit more complicated than a single event of someone losing a job – though birthdays, and Christmas, were never the same after 5 years of age, and things at age 8 things even more dramatically changed. Tie that in with unknown-at-the-time health issues (food-related) which cascaded into more problems, and feeling secure and safe in my environment (and understanding how everyone in an ecosystem affects that) is a challenge, though I know if I can solve the dis-ease of the micro and then be able to work on holistic systems that need societal attention, then I will feel safer and more secure.TL;DR – Fucking childhood experiences that mould and drive your future path of growth – hopefully finding everything you need when you need it.

  16. Semil Shah

    As you posted this video this morning, I was driving down to EWR to pick up family and Jason’s podcast appeared in Swell. This was an amazing talk, it was so real and honest. Listening to this 2x is better than reading 99.9% of blog posts about startups on the web today.

    1. William Mougayar

      What is Swell?

        1. William Mougayar

          I just downloaded it. The UI is very sleek. I like that App! Thanks!(this reminds me I need to comment on your strategy post)

          1. Semil Shah

            Thank you, William. I’d love to have your feedback on Swell, hope you like it!

          2. John Fazzolari

            Really excited about Swell. Key for me is will it be able to pull video content that is publicly available and make it available via podcast (such as the Charlie Rose show). Would I be able to listen to Jason’s podcast on demand via Swell or do you have to just skip through until you get to something you like? The unlimited free listening and skips are awesome too (if they can continue).

          3. William Mougayar

            I like it. But if they could do video grab too, it would be a killer app.- Discovery choices can be improved (need more), and give me a list to pick from instead of loading them straight into the player- Need a Settings for turning off the auto-playOther than that, it’s very well done.

    2. Peter karceski

      Thanks to your combined efforts (Semil and Fred) via email and twitter I had no chance of missing this video. It was everywhere I looked. Thank you!

    3. jerrycolonna

      Thanks Semil. I think part of what the conversation so vivid an experience was the long history between us. It might be surprising to know, though, that that was the first time we’d seen each other IRL in more than 10 years.

      1. Semil Shah

        Wow, 10 years? Yes, these kind of deeper conversations product better content and more serendipitous moments, and can only happen when folks have a shared history. I’m thinking about writing some of the lessons from this conversation on my blog b/c I think it’s so important and not much of this stuff is out there. Thanks again!

      2. Richard

        Thanks for the refreshing honesty about facing the demons. Henry V and all of Shakespear is full of teachable moments, and could offer a literally dramatic approach for your upcoming bootcamps.

  17. Trish Fontanilla

    I started watching with a few windows open while cleaning my house… I quickly realized… nope. Full screen, notebook in hand. Thank you, thank you for sharing, Fred.

  18. Victor Olex

    What a different kind of interview: part confession, part reminiscence, part advice. In Sept. 2001 I was in my first year in New York but I still miss the old skyline. Personal costs do add up and I feel it is better to err on over communicating with significant people in your life vs. shielding them. For me the drive is to be independent and the end goal is to become a gray eminence philanthropist. I wonder what daemons I may be chasing.

  19. Christopher Mance II

    I think the sponsored ads that Jason reads are fine. I never have a problem with them at all. I listen to most of the shows, and this content is so unique there is nothing like it. Listening to Jason read ads is well worth it as the price for admission.The Scott Walker ads come off fine to me as well. I would call Scott Walker without hesitation because of learning about him from Jason.Finally, this interview with Jerry Colonna was the best TWIST episode ever. Kudos to Jason and Jerry for their authenticity.

  20. takingpitches

    “Randomness of life is really unsettling.”So true. it’s magical once you can embrace it some too.Happiness comes from the places you do not expect sometimes.Thanks Jerry – this is amazing stuff. Hope to meet you sometime.

  21. Kirsten Lambertsen

    Wow. 6 1/2 mins in and my head swiveled around to stare at the screen after he said, “God love him, Chris Kitze.” Chris gave me my first Internet job in 1996. I stuck with him through a lot of years. Chris has always understood gamification and what motivates humans.

  22. Nick Terzo

    Fred thanks so much for posting this. Incredibly powerful and beautiful. I have to admit ignorance to Jerry’s history and contributions. I am in a total transition in life and this chat was a remarkable gift. Grateful.

  23. Tereza

    Ahhhhh…..been a long time since I’ve had my Jerry fix. So nice to see you here!Jerry’s guidance was invaluable to me, when I deeply needed it.And — Jerry — as much as I adore you — I guess successful coaching means eventually leaving the nest.So, here I am happily standing on the perimeter — and not IN — the fire. πŸ™‚

  24. The Mail Chimp

    Jason C,All I have to say is “ee – ee – ee-ee”.The criticism of the advertising of the show is ridiculous. As far as I am concerned, you pretty much present the advertising in the most beneficial way to your audience. I listen to TWIST every week, and appreciate the sponsors you have on the show. I have even used some in my business because of the ads you have on the show. The sponsors are directly related to the types of needs your audience has. Keep up the great work.I think this discussion of ads should be a warning to all content generators not to trust tech companies. Content costs money to create. First the tech mavens say they should not have to pay for content directly and everything should be ad supported. Then they complain about the ads. Are companies only allowed to make money by selling their users’s private data?Artists are continually getting screwed by tech companies with poor business models who are hyped and dumped on the public market.

  25. LaVonne Reimer

    Wow! I already did the exercise walk and it’s super hot. Otherwise, I’d go and walk now to internalize what I just heard. The exchange that is sticking in my mind is the therapist’s quick rejoinder about hospital food sucking. Feels like there is a deeper wisdom there than just the note of levity in a horrible time. Maybe that when we feel overwhelmed by trying to do something sort of super-sized it’s good to be reminded of the basics in life and how they can bring their own pleasure. Or maybe the therapist just blurted it out and it was the perfect thing to say.

  26. David Semeria

    Jerry is the dude.Pity he’s not a VC any more.

  27. David Semeria

    Saw the whole thing. This is an amazing discourse.Massive insights both from Jerry (expected) and Jason (less so).So much honesty.Refreshing.Inspiring.Thought-provoking.

  28. ArthurGermain

    Fred, Thank you for sharing this.Jerry & Jason, Thank you for your honesty and integrity in your discussion.

  29. laurie kalmanson

    … more inspired … because you’re real#becauseawesome

  30. Steve Rayner

    This was a great interview. The many things that Jason and Jerry discussed were so critical but also very casual. This added a tremendous amount of humanization to the conversation that drew me in. I’ve watched the video 3 times and really attached to the part where they were sharing stories of their dads and how that sharing, of things that they did not know about each other, brought them closer together in that moment. Jerry, great advice about managing time and family!