I Lost Five Million Dollars This Morning


I found an email this morning that cost me about somewhere between two and five million dollars. It was dated April, 2009.   I was one of two that were cc-ed on the email.The guys who wrote the email , like most people who need money, were desperate. I’m an email hoarder and like to extricate what I can from the archaeological dig that gmail provides me.

There were two emails. Here’s the first:

April 29, 2009:

Dr. Zhivago [name changed to preserve the innocent.]

I’m writing to introduce you to the team at Foursquare, Dennis and Naveen.  They’re a really interesting startup based here in NYC. It’s a location-based service for friend finding and venue finding, and is quickly becoming a competitive game amongst tech digerati in major cities around the country. Killer team, incredibly net-native approach, great game dynamics to increase engagement.

We (XYZ Ventures)  definitely want to continue to follow their progress, but given their current stage, we’d love to see these guys pick up some angel invesment in the near-term to see how their current success can scale over the next few months.  So, we thought of you as a good person for them to talk to. If you have any questions, please don’t hesitate to contact me. I’m sure a conversation with the team will be mutually beneficial.



One person on the cc-list wrote back to Dr. Zhivago and me:

George Washington wrote: [Again, name changed]

I saw them present at ny tech. I thought it was fun but geared mostly towards college kids, but XYZ thought it was a disaster. Pass.

So there you have it: Foursquare. That seed round valued the company at about $5 million. A few months later they turned down an offer from Yahoo to buy them for $100 million in cash.  More recently they raised money at about a $300 million valuation. The business is actually doing great. They are making money. Someone will buy them over the next two years for over a billion dollars. Probably Facebook will buy them.

Whatever I would’ve invested at that round would’ve been worth anywhere between one and three million at this point and much more by the time they get bought. So in my mind, I lost three to five million dollars this morning.

This morning I’m a witness to a disaster. I could’ve had that money.  I also could’ve been deeply invested in Google pre-IPO.  So now this goes on the list of things I regret. Someone might say, “it’s only money”. But money is a good thing. It’s a great thing even.  Every day I find new ways where I potentially sacrificed my future.

And I wrote THE seminal post on how to deal with regrets. It’s easy to give advice. Does Eckhart Tolle take his own advice. It’s easy to speak about regrets, but with one sitting here right in my hand, like a baby bird, will I let it go and let it fly? It’s like opening a window in a jail. It’s easy to climb through it. But will I?

But I will follow my advice:

  • –           First off, I’ll ask, “What am I doing Today?” Since this regret involves money, when I do the Daily Practice below and exercise the Idea Muscle I’ll focus on things that can make me money. I’ll also keep bringing myself back to the present, the only reality that exists for me right now.
  • –          Today I Will do the Daily Practice I outline. I’ll exercise. Exercise my idea muscle. Meditate. Etc.
  • –          I’ll laugh. There’s a new episode of The Office out. I’m excited to watch it.
  • –          Don’t judge people. I won’t judge anyone on this email. Everyone had a rationale for not doing the deal. And I could’ve done it anyway. Nobody was stopping me. In fact, they wanted me. So it’s my fault. I would never judge or blame.
  • –          Honesty. I’m not going to lie to myself. My life would’ve probably been a lot better if I had made that investment. I make a lot of mistakes. Some of them are life-changing mistakes. This was delivered to me in my hands. When you lie to yourself, you keep the regret bottled in, so it never escapes and it infects your brain. How would you like it if someone sawed your brain in half, severing all your connections into two different realities.
  • –          List the positives. It so happens the day I got that email was also the day I had my first date with Claudia. If I had to do due diligence on Foursquare maybe I never would’ve gone on that date. That’s a huge positive. Another positive: I’m happy people thought of me for this. I’m potentially in the flow for future deals.
  • –          Be passionate about your work. I’m about to officially release my latest book: “I Was Blind But Now I See”. I’m passionate about the ideas in this book. Much more passionate than I ever would’ve been about Foursquare. I only have about 40 or 50 years left on this planet. I want those moments to be filled with things I’m passionate about.

(Click image to see on Amazon )

  • –          Good will. Everyone I see today I’m going to wish them well. I’m going to continue to help my wife deal with her sickness. I’m going to do good today. Having extra possessions will never change me being a good human.

All of this sounds sappy. Like I’m trying to make up for something. I can’t betray myself.  I’m never going to be feel GREAT about this email. But so what?

Right behind me I have hanging this picture:



It’s Joe Harris’s initial sketches of “Underdog” before it became a cartoon hit in the 60s. I’m Underdog. And deep down, whether anyone believes it or not, I’m also a superhero.

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  • Great post yet again… disappointing you didnt respond to my text but I understand your busy

    • Bryan, send me an email with your text. I will respond.

  • Anonymous

    Here’s the good news. Also, being an e-mail archivist, I’ve found after an extensive meta-analysis that there are many opportunities to gain millions, many millions of dollars through the largesse of Nigerian Royalty.

    The lesson is to never throw out e-mails, nor the wonderful opportunities. Thanks to following that simple mantra I someday will have a very large penis, pendulous breasts and a Swiss banking account.

  • Even if you would have read that email carefully, would you be invest to have five million dollars this morning. <—  May be.

  • Anonymous

    Life IS a journey, and passion is now (and forever, until I’m broke) my driver. Thanks for the great morning read, James. Looking forward to your new book.

  • Bob Barker

    Get an assistant for Christ’s sake. Never reading any of your emails is straight up bad form. Or simply get rid of your email address.

  • James… hindsight, as they say, is 20/20 and you can’t judge history from the context of today. Do really feel that you lost $xMM this morning?  I think you’re quite a bright guy but am curious if you really feel you had the foresight to predict Foursquare’s potential.  I’m afraid, like “George Washington,” I would have passed.

    • I wrote an article on tech crunch once with my checklist. 4sq probably satisfied three or four of the items on the checklist but not the “light at the end of the tunnel” part.

      Also, I was probably too busy that day. Was my first date with Claudia and it was a mid-afternoon date. So I had important things on my mind!

      • Your date with Claudia was probably worth it considering how it ultimately worked out.  Not sure how to interpret your ‘three out of four’ assessment though.  Given the lack of ‘light at the end of the tunnel’ (among the many other things you were dealing with at the time), think you would have invested?

        Interesting dimension to the story though, your date with Claudia.  Missed investment opportunity versus finding your new life partner.  Life’s an adventure.

        • Yeah, it definitely is. And, for the most part, intended to be a fun adventure albeit painful during many many momemts

          • Believe me brother, I can relate.  

            (Have enjoyed your eBook.  Love your blog.  Thanks! Had planned to email you some thoughts prior to now.  Will do so sometime.)[insert hackneyed platitude here about not taking life too seriously]Enjoy your day. 

  • MrFancipants

    Maybe you should also dig up some emails that asked for money to invest in Flooz or WebVan or something no one has ever heard of because it failed miserably.  Are you going to watch the Roulette wheel land on red 32 and then whine that you didn’t put a bunch of money on it?

  • Fuck foursquare, create your own internet startup and just try to make it more useful than 4sq (not tough), fuck $ for that matter, focus on quality/beneficial products, not pixels for kids

  • Jerry Seinfeld, just yesterday on Anderson Cooper’s new show, said “Money finds those who just don’t care about it.” Most of us will never know the hypothetically life-changing sorts of dollars involved in your scenario. Just means that wasn’t meant to be *your* money. I could’ve gone on a date with NY Giant player. I was too shy and insecure to take the situation seriously. Maybe I’ll write a post about how I could be married to a NYGiant! Hypothetically… and then I’ll go get my mail, go to the farmer’s market, and call my current crush for fun talks.  ;  )  I love your blog, James, and I love the perspectives and writing and non-stop brain-challenges that come with it. Thank you, my dear good man.

    • Sooz

       “Money finds those who just don’t care about it.” (J.Seinfeld)
       The words of a very funny rich man.

      not that I’m funny  nor even close to extreme monitary wealth, but I’d have to agree with Jerry.

      • Sooz

        oopsa..on the monetary

  • jim

    All things considered, I think I’d be more upset if I lost the Underdog sketches than $5M I never had anyway.

    • Underdog was the best. I also have a Ralph Bakshi animation cel from Mighty Mouse.

      • Sooz

        Underdog sketch..priceless.

      • Lori

        this post makes my day just by reminding me about underdog.

  • Marco Bresba

    Another great post that manages to be both positive yet realistic. Thanks.I have been thinking of you and Claudia and her Lyme disease often the past few days. I wish her the speediest of recoveries.Question: why is your latest book not an ebook? Are you going old school on us?

    • It is an ebook. But AMZN takes about 3-4 weeks to convert to kindle.

      • Marco Bresba

        Love the casually use of a stock symbol as abbreviation. I do that unknowingly with SBUX and it confuses people.

  • You never mentioned WHY YOU did not invest !

    also remember, there might be some short term factors that might have driven you towards that – 


    • Anonymous

      James didn’t invest because he never checks his email.

  • Hume

    Is this some way of hyperbole?  You did not lose any money.  Zero.  All other things being equal you had the same amt of money in the bank before and after.
    Now, if you bought 18M worth of Netflix stock, and then sold it for 13M, THAT is losing 5 million dollars.

    • I totally understand though how it “feels” as though he lost five million dollars. And this is the reality of how we process life and so often times move forward it in- responding to what could have been or what we found out from the past. 

  • Five million this morning?  That was over two years ago.  Besides, you didn’t lose any money, you missed an opportunity to make money.  Looking through the lens of 20/20 hindsight is fine, but that’s all it is, you don’t have the same information when making a decision as you do when analyzing a decision afterwards.

    There’s tons of investments I could have made that would have left me richer today, but there’s no reason to say that I made the wrong decision when I passed them over given my information at the time.

    • Gil

      Not to mention such opportunities can only be grabbed by so many people at a time.  Hence you might get 10,000 people who missed a magical investment opportunity that could have only been seized by, say, ten investors.  

  • The really good news is due to the recent discovery of FTL neutrinos, messages can now be sent into the past, warning you to avoid similar mistakes.  This is one of them :)

  • Jay Biddy Trader

    Great article, but isn’t it like saying, “I looked at 50 stocks and one of them grew 10x over the next 2.5 yrs and I missed it.”  I bet you’ve looked at hundreds or even thousands of VC opportunities over the last 10 years.  It made for a great story though.  I love your blog, you’re very talented.  Personally, I bought PCX at $4 in 2009 and sold at $8 and then watched it go to $30 so this is my Foursquare.

  • Katch

    I don’t care about money…

    p.s. money – please find me. 

    • Sooz


  • James,
    Please forward all unread e-mails to me.

  • DanTheMan

    We’ve all read scores of stories about “The Next Big Thing” and could have invested in them (especially the smaller public companies, penny stocks, small NASDAQ companies). Even though we lament about those deals that made truckloads of money for their investors, we must also buffer those missed opportunities with our wisdom for not investing in the majority of those companies who lost money for their investors.

    So even though you may have made $2 – 5 mil on FourSquare, subtract all the money you would have lost had you invested in all those other hotshot opportunities that went into the toilet.

    Startup owners should keep 100% of the equity in their company whenever possible, and personally  invest their retirement savings in no-load low expense ratio index funds (stocks and bonds). Over the course of 10-30 years, it’s almost impossible not to make a modest-to-decent return on the funds, and you can still hit a home run if your business takes off. Owning a startup is plenty of risk. Hedge it with an index fund investment portfolio and you’ll sleep better.

  • Was thinking about Underdog today myself, bizarre.

  • You can invest in me to make up for both those losses.. Kidding, I think. I’ll be in NYC early November.. going to the AVC meetup + meeting with some others. :)

  • Chris

    All this stuff, James, is just part of the marathon of life.

    There’s gonna be plenty more internet start-ups to invest in. You’re 43. Hell, I’m 39 and I keep convincing myself that I missed easy street, but that, of course, is just plain fucking stupid. That’s the domain of anxious and paranoid little manic-depressive writers! :)

    And anyway, we’ve barely been introduced to what digital infrastructure will be needed for the next 5, 10, 20 years.

    Also, FourSquare!  Really? Are you that passionate about the location-based app industry?! Is this what you think your life is missing at this point? Yeah, right… fuck off, James! 

    I bet I can find someone that has invested in FourSquare that is willing to trade their current location with yours, ie sitting next to Claudia … even without the 5 mill.

    Personally, I think (based after reading your blog for the last few weeks) you made the right decision not to invest. Think of that India post you wrote. You’re a good writer, James. A far better one than I am but you know what, I know I belong in the writing game… deep down I think you know that you do too. 

    Forget FourSquare. Forget the 5 mill.

    My pointless advice: Write 5 million words. That’s gonna give you the best ROI of your life.

    Best of all, it costs fuck all to ante up. 


  • Thong

    They WILL get bought, but unfortunately, NOT for $1 B, unless there is major pivoting in the next 18 months. Daily deals is not a good way for 4square to monetize in the long run, since the margins in the industry are going nowhere but down. There is so much more it can do! However, the options are limited as they are potentially competing with Yelp!, Google Places, etc.

  • Jamal

    That’s really weird. Today I was just doing some research into Foursquare (and Tumblr). You say the business is doing great but I am a bit skeptical about that. It’s obviously really cool and popular but I don’t think there are any revenues to get excited about. I think you have to tread very carefully with these dot com startups. Especially in a time when Groupon went from being the darling of all internet startups to being labeled a ponzi scheme (with serious questions raised about its business) overnight. I’m bringing all of this up because I don’t think you should regret your decision. 

  • Jamal

    That’s really weird. Today I was just doing some research into Foursquare (and Tumblr). You say the business is doing great but I am a bit skeptical about that. It’s obviously really cool and popular but I don’t think there are any revenues to get excited about. I think you have to tread very carefully with these dot com startups. Especially in a time when Groupon went from being the darling of all internet startups to being labeled a ponzi scheme (with serious questions raised about its business) overnight. I’m bringing all of this up because I don’t think you should regret your decision. 

  • Funny you would randomly read an old email today. What drove you to read this old email?

    I deleted a few thousand emails today because I was tired of see that huge number next to my inbox.  I wasn’t ever going to read them anyway. So delete – gone.

  • Your Daily Practice post is one of the most useful things on the web, period.  Speaking of which, I’ve fallen behind in the daily practice, and it shows.  Thank you for the reminder, James.  Looking forward to the new book. 

  • Brent Hoag

    “When unhappy, one doubts everything; when happy, one doubts nothing.”a quote by Joseph Roux

    You can’t live in the past; regret simply brings the past back to haunt your present. 

  • Pat

    James, I have a similar problem with communications (procrastinating/ignoring). I’ve been inspired by your blog comments to get myself caught up.  For example: This evening I responded to a letter I received in December 2007. However, I couldn’t respond to the letter because I lost it and I can hazily recall it at best. Furthermore, I didn’t even know the first name of the person who sent it to me! All I found was a torn up envelope and still managed to piece together who to reply to even though half the address was torn off (credit goes to the person living in small town and the internet white pages).  I admitted my faults and apologized and thanked them for their letter. It’s sealed and stamped waiting to go out on Monday.  I feel so much better.  Now on to the next one, which will be easy because the envelope is intact and I still have the letter. Thank you James.

  • Mansal

    Instead of thinking that you lost $5million, maybe think of it as gaining a life partner. If that was your first date with Claudia and you are as nervous as you say, then investing as an angel investor may have thrown off your focus enough to make a different impression.

    Your focus on what was important to you helped you find one of the most important people in your life. That isn’t worth $5million to trade…or $10million, or even $100million…

    …but maybe a billion? ;-)

  • PositvePsych

    Reminds me exactly of what Howie Long said regaring the question whether Payton Manning should retiere given current career ending neck injury (sought stem cell tx in Eu).  Something along the lines of I hope he can accept THE REALITY of that… loose paraphrase… GO PACK! 

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  • Helpguy

    Less what happens than how we respond to what happens that determines our outcomes. You have developed into quite a role model, perhaps even more than you intended, ey?

    Thank you for being a consistently helpful mentor. Frankly, you do kick ass in the mentoring department.

  • Sussan

    I like your passion, James. Your convictions are worth more than 5 million. So is Claudia. Money alone is not good. Prosperity is good, it shares itself and can have a good influence. Sometimes there is more than one way to be fabulously rich. I think you are close to the mother lode because the regret of hindsight leads to foresight. BTW, don’t mystify the chicken, just fry it.

  • James, I don’t think you are being completely fair here.

    True, you missed an opportunity, but what if I emailed you a similar email today and replaced foursquare with hivebuzz (or some other arbitrary concatenation of words). Would you invest in me?

    Hindsight is 20/20. If you invested in every great idea you got pitched, I am willing to bet you would be out a lot more than $5M.

    Like you said, you met Claudia the same day, and maybe you could only pick one thing to invest in that day. You chose yourself. Why look back with regret?

    • Actually, now that I wrote it, I kind of like the name “hivebuzz”. Maybe I should make something with it.

  • Operafaust

    By the law of averages, wouldn’t there also be dozens of ‘missed opportunities’ that might have lost the author millions? It’s easy to beat yourself up for not jumping on Google or Foursquare. It’s tougher to congratulate yourself for avoiding other investments that may have been catastophic.

  • Jeff

    I had a friend that was buying and selling calls and puts on Yahoo during the internet bubble in the late 1990s. He was doing spreads. He was getting whipsawed because of the tremendous movement of Yahoo back then. When it was all said and done after a few years of this nonsense he basically made no money. I then did some figuring. Had he just bought Yahoo leap call options and held them, he would have made $3M. .. It gets worse. In early 1999, he called and said he saw a TV program where the CEO of a penny stock company called E-digital (EDIG) was talking about the great things they would do. He bought 400,000 shares at .10 cents per share. A short time later, he dumped the stock for .14 cents per share, a $16,000 profit. … Look up E-digital it eventually went to $17.00 on 1-21-2000.  Now that was the all time high and the stock eventually deflated and went back to .03 cents.  Had he held for 1 year and sold at the high it would have been $6.8M. 

  • As a tech-start up founder, this has inspired me so much. I will come back in a month to introduce to you, Whenpages. 

  • Guest

    You’re not missing out. Foursquare still makes no money.

  • very sad