We Didn't Know What We Had

I sat next to Jim Cramer last night at a dinner put on by some mutual friends. I hadn't seen Jim in a while so it was a great opportunity to take a trip down memory lane. In 1996 or early 1997, my prior firm Flatiron Partners led the first round of outside financing for TheStreet.com. I joined the board and eventually became Chairman before stepping down a decade ago.

When I first met Jim, he was running a hedge fund and blasting posts from his trading desk. This was 1996 and what he was doing was unprecedented. He was publishing in real time his thoughts on what was going on in the markets. On some days, Jim would post three or four dozen times.

As Jim and I reminisced about those days last night, I said to him "you were tweeting and blogging a decade before anyone else was doing that." He nodded, "yeah, that is what I was doing".

But we didn't know that. The money our firm invested went to hiring a team of journalists and we saw ourselves as the Wall Street Journal of the web. That was a mistake. The Wall Street Journal is the Wall Street Journal of the web. What Jim was doing was something way more native, way more powerful, and way more important. But we missed it.

TheStreet.com has gone on to build a niche financial publishing business that is a solid and profitable company. But it could have been the Twitter and Blogger of Wall Street. That's what it was at the start. But we didn't know what we had.


Comments (Archived):

  1. jason wright

    but back then was the infrastructure, the environment, ready for a Twitter?

    1. laurie kalmanson

      icq was there, barely the original vision of twitter, as i understand it, was to display as a feed the “away” msgs of all your friends on aol chat; they didn’t think of it eitherhttp://en.wikipedia.org/wik…http://en.wikipedia.org/wik

      1. jason wright

        text messaging is celebrating its twentieth birthday, but is falling away to the popularity of imessage and whatapp and the like.1996 is seventeen years ago. i didn’t have my first mobile phone until 2003. twitter as a proto incarnation was 1999. one would have needed a huge third eye to ‘see’ the opportunity in 1996.

        1. pointsnfigures

          I always thought Twitter as cannibalizing the Facebook wall. It was the status update.

          1. William Mougayar

            Until we were able to link our tweets to the Facebook wall to auto-replicate tweets (or vice versa). I hardly post anything original on FB. They are auto-duplicated tweets for my huge FB audience of 123. But that’s just me. I do see a lot of my friends have a ball on FB, posting about their wedding anniversaries, weddings, graduations, baby births, dogs or cats, family dinners, humor, cartoons, snow shots, etc. They entertain me & I thank them.

          2. falicon


        2. laurie kalmanson

          time flies like an arrowfruit flies like an apple

          1. jason wright

            i have my banana boomerang ready to fly at the drones

          2. laurie kalmanson

            all ur drones r belong 2 us

  2. reece

    always hard to identify what could bealways easier to connect the dots in retrospect

    1. JamesHRH

      Been reading Taleb? ;-)Hopefully not, he is a horrible writer(iinteresting thinker).

      1. reece

        eh.. not really. read some of his stuff years ago, but really just speaking from my own experience

  3. maxniederhofer

    Is Twitter the Twitter of Wall Street?

    1. William Mougayar

      I think StockTwits is.

      1. John Revay

        I think Howard is the new Jim Cramer

        1. pointsnfigures

          let’s hope not.

      2. pointsnfigures

        Barry Ritholz did a blog post about Twitter being the new tape. Stocktwits is that +1.

  4. laurie kalmanson

    there’s been a whole lot of disintermediation since then …

  5. Dormat Hidatsa

    I’ve made the same mistake, can look back on lots of early stuff that I didn’t recognize the value in. Learned to trust my intuition more. πŸ™‚

    1. fredwilson

      yup. in the same tools and technology space.

      1. Henry Yates

        There have been quite a few comments about intuition recently (which does resonate with me). However, is it likely we are falling for a cognitive bias and we are remembering the times we ignored our gut and missed big opportunities but not recalling the many times when the reverse was true?

    2. William Mougayar

      I was a very early user of Radio & Userland. My old sites still show up in search results. I think they were permanently etched into the index fabric of Google.

    3. William Mougayar

      Dave, I meant to say despite of that, you did inspire thousands, maybe millions of us, both with your work with RSS and Userland/Radio.

      1. dave

        Thanks it’s nice to know when one’s work is appreciated! πŸ™‚

    4. robertdesideri

      What happens all too often is the startup gets itself into an intellectual rut, it can’t see the bigger opportunity. Stuck on the wrong saddle. And if they see a better opportunity they perceive it’s too reputationally risky for them to go back to their VCs based on ‘mere intuition’. And sometimes the CEO is just too close to the matter to see the bigger opportunity. I’m fairly certain we’re going to see a good number of repeats of this ‘didn’t know what we had’ post when the dust settles re several of the big deals in the pipeline. There’s so much potential in a few of these companies, but they’re not going to realize it while in the rut. The true shame of it is greater returns for LPs could be achieved, the funding model is part of the problem. And the startup leaders are happy hitting singles when the going gets tough. Should fight the urge and go for it bigger. Would like to see more aggressive leadership in some of these startups, particularly the ones that have matured in years some. Intuition? Yes, it gets one out of the rut. More intuition, combined with more aggressive pursuit.

  6. andyswan

    Yes but Jim Cramer is the Jim Cramer of the world now….which is more powerful than TheStreet.com and possibly “the twitter of Wall Street”.Maybe there were technology implications that you guys missed… but in terms of creating value, that innovative and instinctive spirit paid off in spades.

    1. fredwilson

      i don’t think a personal brand is worth more than a global platform. to Jim, maybe. to the world, no way.

      1. andyswan

        Agree… Was just finding the positive on this Tuesday of derby week

        1. pointsnfigures

          Cramer is more interested in using things like The Street and CNBC to make himself famous and a star rather than building a company. Great CEOs accept the fame that accrues to them by building something great-they don’t seek it out. Cramer seeks it out. I think he wants someone to make a movie about him.

          1. andyswan

            I don’t pretend to know (or care about) his motivations but I do admire his work.

          2. pointsnfigures

            I used to like him, but he has become a caricature of himself.

          3. howardlindzon

            the early work was inspiring for sure

          4. btrautsc

            I will play Jim Cramer in that movie if I can yell with my sleeves rolled past my elbow and chop off tiny rubber bulls’ heads.In 1996-1997 I was 11, Jim Cramer taught me to love finance – reason I was a finance major. I remember reading posts from the street, but still checking stocks in the back of the business section.

          5. LE

            “Great CEOs accept the fame that accrues to them by building something great”Probably a happy compromise between being nobody and being recognizable by everybody (and always being bothered) is to have some degree of fame such that you have certain people that know, admire and recognize you but you can still walk around and be anonymous. So you can turn the smoke on and off like a switch and dose it accordingly.Even at that level though it can be annoying. Remembering Fred’s post about Gotham Gal getting bothered when they were at dinner and someone would come up to say hi or pitch Fred when they saw him.

          6. pointsnfigures

            I don’t think Fred brings a pen to dinner to sign autographs, Cramer has 8×10 glossies in his jacket.

          7. Timothy Meade

            Fred has more important things to sign at dinner parties.

        2. PhilipSugar

          Take the horse from where I live Vyjack πŸ™‚

      2. William Mougayar

        Also, the scale of online users wasn’t there at the time. He appealed to a fairly small segment initially.

        1. Donna Brewington White

          The scale of online users seems like it would be a huge factor. I wonder if something launched to a segment would be perceived as belonging to that segment and disregarded by the larger audience — or how long it would take for the association.with that segment to diminish.

          1. William Mougayar

            I think it would be depend on that segment’s dynamics, i.e. if it’s a growing segment, then if you are a player in it, you grow with it.

      3. howardlindzon

        agreed. amen.

      4. LE

        Everybody is different.Some people thrive on getting smoke blown up their you know what by everyone and anyone.Others would rather be behind the scenes. Personally I can’t stand even when the barristas at Starbucks recognize me on a daily basis. I’d rather be ignored (treated nicely but ignored.) Others really like the fake attention you get at a Casino when you are losing your money there.

  7. William Mougayar

    And he was doing online chat sessions, way before Reddit’s AMA. I participated in a couple of them. They were unmoderated & he typed & responded fast & furiously to the participants.

  8. JimHirshfield

    “But we didn’t know what we had.”We never do. Do we?

    1. fredwilson

      you gotta try to

      1. JimHirshfield

        For sure. Didn’t mean to sound defeatist.

    2. panterosa,

      Isn’t this why teaching pattern recognition and how to see and think is so vital.

      1. JimHirshfield

        Indeed. The hard part is that not all opportunities look the same…or have the same pattern. The world changes. The rules change. The tech changes. etc.

        1. panterosa,

          We need to teach how to think, not what to think.

  9. Richard

    Fred, what year did you adopt the investment vision of “large groups of highly engaged users” ?

    1. fredwilson

      Can’t recall. Maybe 2007

  10. Brad Lindenberg

    Fred, in January 2009 I ran a sale at the eCommerce company I founded back then (lindgolf.com).We ran 24% off for 24 hours. It was the single biggest day in sales we’d ever had, by a factor of 400%.Then Groupon arrived and did it every day. We didn’t know what we had.

    1. fredwilson

      Knowing what you know would you have done anything differently?

      1. Brad Lindenberg

        Do you mean with respect to Groupons current state of affairs?All i can say is that we all try our best to make the best decisions we can at the time, and it was obviously more clear to Andrew Mason that this was an opportunity than it was to me.Having said that, Groupon doesn’t excite me. It’s a quick win business. I like long term businesses.

  11. Elisabeth DeMarse

    Hey, Fred, it’s never too late. We have $60 million in cash, we have great voices in our newsroom, and once we ditch our legacy tech stack, watch out.

    1. fredwilson

      I love the attitude!

    2. William Mougayar

      I just realized you are the Chairman & CEO of TheStreet.com.

    3. ShanaC

      πŸ™‚ thanks for stopping by – why are you still using your legacy stack in the first place

      1. Elisabeth DeMarse

        Hahaha. I wish we weren’t. We moved from Equinix to Amazon Cloud in ’12, saving $1m plus. Now we are working on WordPress CMS authoring, which will let us be more Stocktwits like in scaling contributors. Then we have to dump Oracle for mongoDB. The n we can put cool elastic rendering on the front end. More like Stocktwits, more like Forbes, more like Seeking Alpha. Gruesome process, but well worth the long game.

        1. fredwilson


        2. howardlindzon

          makes sense.

          1. Guest

            this is why avc is incredible…

          2. howardlindzon

            in that there is no argument.

          3. markslater


    4. takingpitches

      i love these drop-bys — good luck to the Street!

  12. William Mougayar

    Since we are going down memory lane, in 2001 I started a (Joomla) blog called PeerIntelligence, where we chronicled everything about peer-to-peer technologies & applications. It could have turned into a TechCrunch, maybe. Maybe not.Timing & large availability of users are key factors.

    1. awaldstein

      Don’t underestimate luck.Honestly, we make decisions as a leap then what happens happens.We tried to be the first company to commercialize consumer connectivity with Racal and Hayes kicked our butt.We tried to be the first company to commercialize prosumer editing tools with Digitial F/X and Avid kicked our butt.We tried to be the first company to own the audio space in computer games and had a giant mail sack of 5000 BRCs of developers who wanted our SDK. We kicked the markets butt.We tried to own the 3D space in movies and we won.Many in-between, many half wins and turnarounds.I believe in trying to be perfect but I just believe in timing and and no matter how you nudge it, timing is basically luck.

      1. Carl Rahn Griffith

        Absolutely, Arnold.We don’t like to think parts of our life (both personal/business) are down to matters out of our control but I suspect it is more often the case than we will every know…

        1. awaldstein

          You get smarter about choosing the elements. You get better at your job and better at knowing what you need to be successful. Smarter about financing, partners, blah blah.Here’s the rub though that is interesting. Sure success happens somewhere at the intersection of your skills and intuitions and happenstance and luck.But some win more. Many don’t win at all.You follow, support, fund, listen to those that win more obviously.What’s the X factor?

          1. Carl Rahn Griffith

            Aye.Search me – that’s the $64m question!

          2. John

            To go huge takes luck. To be successful doesn’t require luck, but it doesn’t hurt if you have it there too.

          3. awaldstein

            The market is 95% of the challenge and 100% of the opportunity (Marketing matters… http://awe.sm/iEjaA).So whether you are going big and need a huge slice of market awareness to win, or going local and need the people to who turn right on Chambers Street to walk on the South side of the Street to find your shop, it matters not.if it didn’t you could have perfect execution (which you won’t), a perfect idea (which you won’t) and everything will be all clear skies (dream on). You are then a sure bet–which no one is.I’ll punt to Mike Tyson that ‘Everyone has a plan till they get punched in the face.” And no business doesn’t get bruised and battered on the way to the pay window.Luck is real. You can make it your own but it still is just that, the uncontrollable.

      2. William Mougayar

        Yup, luck and timing are intertwined.

      3. LE

        “Don’t underestimate luck.”Just like all those people who bought real estate in NYC in the 70’s and 80’s.My dad passed up an opportunity to do that (we were in Philly but there were opportunities presented). He bought elsewhere and did ok but nothing compared to what would have happened if he had done the same in NYC.

      4. ShanaC

        luck is a huge problem – you don’t know if you had it until afterwards

        1. awaldstein

          I’m super positive lately and thinking that I’ve earned some forward looking luck based;)

  13. Dave DeStefano

    When I think of thestreet.com, Cramer is the sole picture in my head. If they created a platform to allow others engage him rather than defining the infrastructure’s potential by having only 1 superstar content creator. Nothing against what they did, but if they had more fund managers & PMs they could’ve made an online saloon where people could see who was thinking what and engage.Jim Cramer is a brilliant guy and if anyone looks for a good albeit quick read, his autobiography “Confessions of a Street Addict” is recommended.

    1. howardlindzon


    2. LE

      “but if they had more fund managers & PMs”Agree. But most importantly to somehow make those others stars as well.All this can be manufactured quite easily.I think this is important for any company to do. To not have everything in one celebrity basket. Apple did this with Jony Ives but what they really need (what any company needs) is a bunch of people, a dream team, that people can buy into.

      1. Dave DeStefano

        I wouldn’t even worry about celebrities- it’s about the talent. In this situation, they’re practically interchangeable.Apple is where it is because of Job’s magnetism and personality. Was he easy to work with? Not from what I heard, but he brought the best out of people all in name of creating the brand.It’s similar to AIG’s current predicament- they just look 4 major employees to Buffet’s Berkshire. They say they have the bench to back it up after having the head of a very profitable unit wiped out, but only time will tell.

    3. Bhargav Shivarthy

      Howard and the Stocktwits crew are building the ‘online saloon’ you talk about. Plus, they are making it easier and easier for you to identify and follow the thoughts and ideas of great investment talent.At covestor, we have this – http://investing.covestor.com/ and while it may not exactly be the ‘online saloon’ experience you are looking for, it might offer you a view into what a variety of PMs are thinking and how they are positioning their real-money portfolios using a host of different investment strategies.Also, as most of our PMs are on stocktwits already you can engage with them there.

      1. Dave DeStefano

        Looks very interesting! I’d would try it out, but compliance and designated brokers would beg to differ.Real-time tracking of PMs and strategies along with emulating their trades? Very intriguing. Fees seem manageable too.

  14. Kirsten Lambertsen

    In the early 2000’s I worked at a company that was YouTube before YouTube. We didn’t know what we had either.Except, we didn’t really have it. Because the market wasn’t there yet. The bandwidth wasn’t there.The founders didn’t have the patience or funding to wait for the market to catch up. So they pivoted… to micro-payments. i++.

    1. fredwilson

      There were a lot of youtubes before YouTube. Lots of lessons there

  15. Elisabeth DeMarse

    Hey Fred, never say never. We have great voices in our newsroom, and a terrific, smart, engaged set of readers. As soon as we ditch our legacy technology stack, watch out.

    1. howardlindzon

      Stocktwits can help…hello

      1. Elisabeth DeMarse

        Howard, thanks for reaching out. Lets coordinate calendars.

        1. howardlindzon

          howard at lindzon dot com anytime

  16. Dave Goldberg

    Yes, but isn’t there also the question of: “Even if we knew, would we have been too early?” Sometimes you can be too far ahead of the curve.

    1. fredwilson


  17. ObjectMethodology.com

    Hmm… Nice post. Maybe everyone that they should take some time today to be sure they know what they have. Or more importantly to make sure they are taking advantage of the best that they have..Which leads to the question “How to Know What’s the Best of What You Have?”

    1. Mac

      Well said. Nice reminder.

    2. William Mougayar

      Good point.

  18. pointsnfigures

    and now there is stocktwits.com. The Street could have still started something except as you cite, they didn’t see themselves that way.

  19. Tom Labus

    But no one did including Jim et al.

  20. Seenator

    In your opinion: Is there an existing service (StockTwits, Seeking Alpha etc…) that is most likely to end up being like the Twitter/Blogger of Wall Street?

    1. fredwilson

      I am rooting for Howard. He’s awesome

      1. howardlindzon

        thanks bud

    2. kidmercury

      the game is over and seekingalpha has won

      1. howardlindzon

        complete nonsense. describe winning

        1. kidmercury

          hard to know the score for sure with private companies since numbers are not readily available. profits is one measure. market cap is another. we could look at revenue per user, or something like that, but those numbers aren’t clear with private companies either.but i think SA has the most fully developed, integrated platform, which strategically i think is the name of the game. they also have in my opinion the best user-generated content, which i think is also the name of the game for the media plays.there’s plenty of room for niche players. in fact i only participate using highly focused, niche services like casey research. but to the extent that there is broad general market for US stock research, i think SA has the defensible network.oh, honorable mentions go to business insider and zerohedge for the broad dominance they display, though they are not really social media plays.

          1. howardlindzon

            the winning thing is rhetorical.if you like seeking alpha you like it. I cant use the site and dont trust the info. users are locked into their platform and I have never heard of a happy long term contributor in my sphere until youas an investor in biz insider i agree there. zerohedge proves that being wrong is good for page views so cant argue on that one.will think more about the term ‘defensible’. I prefer offense around innovation not defense around things.

          2. kidmercury

            hahhaahaha i think you have biz insider and ZH reversed — biz insider is the one proving being wrong is great for page views! weisenthal and blodget are my morning chuckle, and my contrarian indicator. i will give weisenthal credit for being a good writer, if perpetually wrong.i didn’t say i was a happy long-term contributor to SA; i don’t really contribute there anymore. that they share the most revenue with contributors out of any other platform speaks volumes though. the platform that creates and shares the most economic value is the one that will invariably win in my opinion. actually now that i said that i would regard that as probably the defining metric of winning.

          3. howardlindzon

            Oy…you are a lost soul.

          4. kidmercury

            hahahaha! well we’ll see…..weisenthal is perpetually bearish on gold and bullish on the yen which suggests those are his long-term outlooks. i just hope for the sake of my portfolio he’s bearish on uranium…..

          5. howardlindzon

            wiesenthal is an old school journo hound and good man. if you use him as any market indicator i am so glad i dont take your investment advice πŸ™‚

          6. kidmercury

            i wasn’t sure if i should buy more gold on the dip last week, or if there was much more room to go down. there were some technical signs of exhaustion on gold stocks but i wanted more evidence. then weisenthal and the whole BI crew started running their mouthes and that was all i needed to add to my position! πŸ™‚

          7. mickwe

            When BI first launched we thought it would be directly competitive to us at SA, but it didn’t turn out that way. They went more in the general topics/BuzzFeed/HuffPo direction and with more editorially produced posts/rehashes than we did. We stayed more focused on the market/individual positions, content produced by our contributors, and a custom CMS/edit team that focused on that. In the end, both models worked.Bottom line: you have to find where the talent and passion are and build around that. For BI, it’s a super hard working core team that knows how to do its brand of scalable, engaging online journalism well. For StockTwits, it’s enabling a passionate group of serious traders/investors who want realtime engagement. And for SA, it’s been enabling a large group of serious individual investors and some institutional to discuss their process in longer form. It was clear to us in 2004/5 that TheStreet and MarketWatch weren’t moving on this opportunity, so we did. They didn’t move away from the traditional journalism model and toward the new center of talent/passion/quality (bloggers) fast enough.The big question now, as I see it, is what mobile will do to upset the existing players – just as blogs/Twitter did to TheStreet and Marketwatch.

      2. Elisabeth DeMarse

        We like the contributors and front end of Seeking Alpha for sure. But they can’t indemnify. We will aim for thoughtful curation, not promiscuous amplification.

    3. howardlindzon

      there is no such thing as winning…there are different styles and strategies and focus. we are focused on the trust and education and reputaion and even fun of the business of stocks and markets. we are a journal for those that want to chronicle and a platform for those that want a voice.

  21. Devrin

    Great post Fred but I would challenge that in this situation a great idea just came at the wrong time. There’s so many terrific examples of great ideas that came along but didn’t have either the market awareness for traction to take hold. Microsoft Tablet PC for one, Apples Newton for another, Or DNA sampling from another era.The reality of it is that the perfect storm of consumer awareness, technological advancements and overall timing need to align. My feeling is that true advancements take one or two iterations before they get it right. The first often times is just a feeler in the marketplace to expand the balloon of what’s possible before it legitimately takes hold, usually in the second or third iteration. Jim truly was on to something in 1996 with his real-time updates. But it took almost 2 decades later for the concept of real-time messaging and micro updates to come to life. It’s great to acknowledge what we have, but also the other planets need to align to breathe fire and life

    1. fredwilson


      1. Jose Paul Martin

        Fred, maybe you should start an Anti-Portfolio like Bessemer Venture Partners – http://www.bvp.com/portfoli

        1. fredwilson

          i have one. but its in my mind.

          1. Jose Paul Martin

            (was reading your post on DD, should have posted it there…)Look forward to it! Will bring some insight into the mind of VCs πŸ™‚

  22. JamesHRH

    The posts are tying together.About a decade ago, I went to work with someone I knew pretty well. He had a video jukebox platform. I worked through the potential product market fits (not what we called them) and told him we should focus on retail PoS or PoP application for digital video.He wanted to ‘fix’ the music business.Sometimes, what is there is not what we want.Now, I can’t go buy anything anywhere – WalMart uses digital video as an aisle capper in their superstore layouts.Jeez.

  23. awaldstein

    Do we ever?

    1. Carl Rahn Griffith

      We certainly do – when it’s gone! πŸ˜‰

    2. fredwilson

      You are going zen on me Arnold πŸ˜‰

    3. Mark Essel

      once in a lifetime.

  24. Elliott

    As Jim has acknowledged in his book, as a hedgefund trader, he would feed CNBC reporters false info to further his short positions. It is difficult for regulation to stay in front of technology or evil intent.

    1. Max Yoder

      Ouch, that ain’t kosher.

      1. pointsnfigures

        he wasn’t the only one doing it. I don’t like that he did it, but gets points for being honest about it.

        1. Max Yoder

          If I have to choose, I prefer an honest con-man to a phony.

        2. LE

          He gets points for carefully weighing the pros and cons of “being honest” about it. If that were not the case, being honest about it would be stupid not smart.Does Obama get credit for being honest about his drug usage (apparently even cocaine?) or is it simply a move designed to head off at the pass a story that if others revealed first would be more powerful and harmful?If you reveal something negative it becomes much less of a story than if others do so. Lawyers do this in court for unsavory clients all the time getting the bad out first before others can do so. Tends to dampen things a bit.

          1. pointsnfigures

            Uff, Obama not being honest about a lot of things. Politicians never are. Cramer divulged it after he made money about it-but at least he divulged it. If you knew the way the sausage was made on Wall St you’d trust it even less than you do now. At least Stocktwits and other bloggers are starting to pull the curtain back.

    2. kidmercury


  25. howardlindzon

    Yes Jim invented this stuff as you said and the financial community at Wallstrip and now Stocktwits always talks about. What they missed, other entrepreneurs have grabbed onto.Here is our Wallstrip’s great homage which we took so much time intricately thinking through to honor, not smash the persona:woops it wont paste… (go to youtube, than search ‘wallstrip and Jim Cramer’)There is no grass is greener model, just timing, the right investors, right cap table and of course visionary execution.I remember taking Wallstrip to the Street.com team in 2006 and saying buy Wallstrip and let me help build a great video channel …I remember taking TheStreet the ‘idea’of Stocktwits after CBS and offering them to invest in the very first round with Andy Swan, Eric Bolling, Jim Altucher and many other friends from the industry…nope!!They have passed many times on this new type of model as Twitter and Stocktwits and video (hangouts are cool now) Blogging have evolved and pushed the boundaries.In the beginning, they knew what they had, but the bankers and investors and momentum of the day steered this company to the at the time finish line (get an IPO) Jim was there to watch it and yes its too bad because that should be the beginning, not the end. Check the stock price, that was pretty much the end.. Jim inspired a lot of great financial writers and with their traffic have had the chance to get back to their roots many times.Jim in many ways pushed the idea of beg for forgiveenss, not ask for permission that is the only way to change things with walls as high as wall street has.The industry needs more of that old entreprenuer Jim, all the time, from people like Jim to help move the industry forward. No IPO’s are attached to that these days or likely money, just arrows in the back.

    1. William Mougayar

      True. I was part of that era of early admirers and followers. He was the idol and the bad boy at the same time, maybe like Justin Bieber a bit.

      1. JamesHRH

        I find that people end up getting what they want in life.That would suggest that Jim likes being famous and listened to (over rich and influential).

    2. fredwilson


  26. Max Yoder

    I know you don’t need the encouragement, but you’re on a roll with these posts, Fred.

    1. fredwilson

      Four hours sleep last night. I watched KD try to win it all by himself. He could not.

  27. Fraser

    Reading this shortly after reading your tale of Donors Choose / Kickstarter puts it in an interesting perspective. You didn’t know what you had the first time around, but you didn’t get fooled the second.

  28. Nik Souris

    Either way… you knew you had a good thing πŸ™‚ #GoodFeeling

  29. jim miller

    The Street.com is anything but a profitable company. It has an accumulated deficit of about $180 mililon and lost $12 million alone last year.

    1. Elisabeth DeMarse

      Beg to differ. You KNOW sub businesses are WAY profitable, and you KNOW the difference between opex, AEBITDA, restructuring and d&a.

      1. jim miller

        Cash flow from operations have been negative for the last 4 quarters……not “solidly profitable” in my book or most people’s books. Maybe EBITDA positive or something else. Or maybe the ship has been turned and Q1 will be better. But “solidly profitable” is not accurate.

        1. kidmercury

          siding with jim in this beef. EBITDA is #cheaptalk. free cash flow is #realtalk.

          1. Elisabeth DeMarse

            Accumulated Deficit not on my watch. We could suck it in and hurt ourselves. I’m a graham and Dodd person, but we need to grow, too.

  30. TamiMForman

    It’s funny, I’ve had this same thought about iVillage, where I was an editor from 1999 to 2002ish. Community was a huge part of it and we knew some people met IRL (“in real life”). But it never occurred to any of us that people who *already* knew each other IRL would want to interact via computer. That is, until Facebook. Oh, what we could have been! (Though I will always stand by iVillage as revolutionary in its own way — 1995 the idea that women would spend any time on the internet seemed nutty. Now it seems nutty that anyone thought that was nutty!)

  31. Jacob Slevin

    Haven’t read all of the comments yet, so this is possibly addressed already, but would “knowing what they had” have been meaningful in 1996-7? They may have wound up “knowing what they had” and been too early to market at that time. I’m not convinced that the world was ready for the Twitter/Blogger of Wall Street, and I wonder if they’d pursued that track, would they still be a solid and profitable company today?

    1. mickwe

      Their opportunity was around 2004-5 with the explosion of blogs and distributed expertise (we got that at Seeking Alpha), and then a few years later with the growth of Twitter (Stocktwits got that). In both cases, though, you needed to think differently from traditional journalism about where the source of value lies and how to build a business around that.

  32. LaVonne Reimer

    I love this post. It highlights the oh so human element of innovating and seeing it not quite achieve the vision you had or in hindsight “should” have had. Timely in a strange way. PandoDaily has been running a series on online education. This morning I woke up thinking it has helped me move on. Recap–I founded and ran a VC-backed e-learning startup in the first wave. When second wave emerged I would have nothing to do with it, not even read any of the news. Then I cycled through ticked. How dare they act like they came up with something new? I knew I hit the next stage when I was watching a show on the subject, maybe 60 Minutes, and found myself blurting out loud, “oh those darling young entrepreneurs. They are so earnest!” This led to paying attention again and even commenting on your posts and others on the subject. I felt like the wise old hand though at times I did think longingly that I wish I knew what I had back then. It has run its course now. I have new things to focus on so I will just cheer for this new crop of startups and wish for them to know what they have!

  33. laurie kalmanson

    had a meeting to day with an entrepreneur who had a heavy regulation bell system rotary phone on his desk, which he let me pick up and dial. it was a strangely anachronistic experience — completely natural, yet wholly antique.

  34. Guest

    The banks in Web 1.0 already had their own Twitter. It was called “Chat” and was an in-house incubation at the bank where I worked that was spun out. The technology later got acquired by MS.I’ll share more if we ever meet in the future!

  35. Jonathan Sandlund

    Fred β€” I love your stuff. But you need called out on this.Do you realize how much working class wealth Jim Cramer destroys on a daily basis? Hard-working, everyday people who actually believe in his ability to make well-researched calls on thousands of stocks a year? I don’t care what he puts in his risk disclosures, when he screams “buy buy buy” or “sell sell sell” people listen. And act.Jim Cramerβ€”and TheStreet, and Motley Foolβ€” enriches itself by selling an investing culture that is empirically proven to destroy wealth.Investing isn’t a game. And people’s retirements, and lives, are destroyed by the pop investing culture that Jim Cramer more than anyone has helped build and perpetuate.He’s a charlatan. You didn’t miss anything…

    1. fltron

      Glad someone said it.Hard to give any credit to someone that blows a horn to offer financial advise, but this is more a commentary on the morons that listen to Cramer’s financial advice. Granted, beyond the sh*t show that The Street and Cramer’s rise to fame has always been, not sure if there’s actually a difference between that and most of the talking-heads on financial shows.CNBC did a pretty good job for stock traders before Cramer started becoming a regular, at any rate. But hey, clearly Cramer got the viewers.

  36. JLM

    .I passed on buying the Corona beer franchise in Austin, TX in 1989 — thought it was a “fad”. Could have picked it up for $1MM for entire going concern. About 2 x TTM.Fuck me.Never piss into your own beer. Suck it up and move on. The next deal is right around the corner.Still, fuck me.JLM.

    1. John Revay

      #CouldhaveWouldhaveNeat story

  37. Keenan

    You would have been too early!

  38. george

    Connection – JC as an innovator? He was just the loudest one making noise that captured an audience.

  39. John Revay

    TheStreet.com / Jim CramerI think Oak Investment Partners / Ed Glassmeyer invested in TheStreet as well, it was after my time at Oak.

  40. Lloyd Fassett

    This story is also more important than it looks on the surface. I have a pdf of Marketing Myopia by Theodore Levitt if you like to read more. Its considered a HBR Classic about interpreting markets. I wonder how much doesn’t happen, more than what does. For example, why did it rage so long to get wheels on luggage?

  41. Philip Brown

    Hi Fred, do you have any more examples of companies that moved away from a experimental business model that only later proved to be a huge success by someone else?

  42. LE

    Intent and execution.Location counts also. Let’s say you weren’t in Lancaster at the time? Let’s say you hooked up with some different people in the right place?(Am I totally off here? Where were you?)

  43. falicon


  44. ShanaC

    yes. you might execute, but not based on your intent

  45. PhilipSugar

    Great comment. You have to intend to do something and then actually execute on that intent.Anything other than that is just hope and fantasy.I cringe when I hear people say: “I had that idea and could have been…” Why even waste one CPU cycle of your mind on that.If you weren’t acting on the idea, it was just a passing thought.You got out fund raised, you were doing it and were too early, I hear that.

  46. awaldstein

    Actually we all do. Except of course is that we are most often wrong.

  47. awaldstein

    I’m about to build a spread sheet for Lianna that figures out how to express margins over 40 different ingredients, measured in five different integers, for 20 SKUs and spits out a purchasing and delivering sheet.Just saying….Ice Cream (especially raw) sounds way better.

  48. awaldstein

    Yum….but the worksheet I built is honestly, pretty cool.