Ten Years of Blogging…What I Learned

Over the course of my career, I have invested (personally,through my hedge fund and through Social Leverage) in over 100 startups and started a few companies myself. I’ve made good trades and bad trades, met mostly incredible people and had some great mentors.

I started this blog 10 years ago today to journal and keep myself honest and accountable for my decisions. And while ten years of archives inevitably includes some cringe-worthy nuggets, on the whole, I’m proud of what this blog has turned into. It definitely served (and continues to serve) its purpose.

Ten years is a long time, and it’s fun to look back. Steve Jobs once said, you can’t connect the dots of your life and career looking forward, but looking back you can see the pattern. And that’s definitely true.

One of my dots was a Google search I made in 2005 for ‘term sheet’, which led me to Brad Feld, and through his blog to Fred Wilson. Their writing inspired me to write on my own. So thank you Brad, Fred, Google, and WordPress (and before that Google Blogger), for enabling one of the biggest leaps forward in my business life.

Another dot was Youtube, which inspired me to create WallStrip (2006) and eventually led me an acquisition by CBS. A third dot was Twitter, which inspired me (though you wouldn’t have guessed it from my very first ‘tweet’ ) to leave CBS and start StockTwits. And most recently, Robinhood added a dot that’s inspired me to keep pushing the envelope of personal investing and get another company off the ground called Spark.

Those dots connect a path that’s led to place I couldn’t have predicted, but is one of which I’m immensely proud and grateful. When I take an early morning run on the Coronado beach, I don’t ever take it for granted. So most of all, thanks to all of you, for reading and commenting and being a part of my journey.

On any journey, you come to learn some things (sometimes in spite of yourself). So in celebration of my 10th anniversary of blogging, here are TEN I’ve come to believe:

1. Everyone should be an investor. Trillion dollar companies can’t exist without the public market. The public market can’t exist without the private market of startups, venture capitalists, and angel investors. We need capital and PEOPLE to invest.

2. Anyone can learn to speak the language of the markets. Obviously reading is the key, but writing remains undervalued.

3. The game is rigged, but it doesn’t matter. It may be rigged in general, but it’s not rigged against you specifically. So stop hating the players and learn to play the game. I love this historical look at why ‘the market is rigged’ by Josh Brown.

4. Your greatest asset is your network (social and face to face). Invest in yourself and your network. One of the oldest races is the ‘Tour De France’. The ‘peloton’ is a french word originally meaning ‘platoon’. A well developed peloton helps reduce ‘drag’ or as I like to say, speeds you up by as much as 40 percent.

5. Investing does not have to be a career…it can be a lifestyle. You should invest for profit but there is joy to be had. I started Stocktoberfest in 2011 to push this idea of ‘Investing for Profit and Joy’ forward. This year over 400 people attended on Coronado.

6. Ignore the news. ‘Markets in Turmoil‘ are opportunities. If it bleeds, it leads. The rest of the world talks about failure and pain endlessly. I focus on what is working. Everything’s amazing and nobody’s happy (so funny and true).

7. Investing is as much behavioral as financial. The numbers make for pretty charts, but fear and greed are what drive the markets. If you understand people, you have an advantage.

8. Always have a system. I don’t care if your system is investing in the $SPY (S&P 500). I started this blog as part of my system to keep myself honest and then starting StockTwits to find my peloton. Figure out your system and hold yourself to it.

9. Trust in people. As an angel investor my success has not come from discovering the best idea and the biggest markets, but by backing the right people. I have no problem following my gut into an investment on a person I’ve met and taken the measure of.

10. ‘Too Small to Fail‘. In October 2008, I blogged about the idea and I live by it today. I won’t be the wealthiest person on the planet but it has made investing and my life much more profitable and joyous. I love how Seth Godin picked up on the idea and furthered it.

Have a great New Year everyone and please say remember to say hello in the comments anytime.


  1. Edward Graham says:

    I have to make this comment because i think its funny that howie hasnt made a dime off his investments in the markrt but made a coin selling a business that talks about stocks. And once again he is doing so with stocktwits which is pointless. Twitter has more information than some shit site with a bunch of pointless daytradrr tweets. I told howard many times to put a filter so that we dont have to see these incompetent degenerate s tweets everyday. But as expected he and his shit handlers of stocktwits banned me. This guy is fuckn incompetent and clearly CBS too was when they boughg his shit wallstrip business. Bunch of fuckin morons associate with this guy. Like allstarcharts and ivanhoff. Both backed by howies money and both keep losing money actively trading. no wonder why this guy and anyone he Associate s with loses money in the market

      • cousin_vinny says:

        Reading these comments have me in stitches. It’s funny how the very people calling everyone else a moron come across as exactly that.

        • Edward Graham says:

          just as long as your wife doesn’t have you in stitches I guess your actually winning. Better than being in stitches over the market like the nerd howie

      • Edward Graham says:

        thats how dumb you are. You only hear what you want to hear. Sorry brother, I actually invest in real companies. Not fairytale penny stocks

  2. Edward Graham says:

    And to prove how shit wallstrip was, where is it now. Oh ya the same place where every hopeful business goes when bought by a bigger company. To the shit and defunct

  3. William Mougayar says:

    Too much wisdom in that post, Howard. Did you write it?
    (Just kidding)

    Good knowing you for 7 of those 10 years, and thanks to you for introducing me to the world of AVC.

  4. lisa hickey says:

    It seems to me your dot-connecting ability is fueled by optimism—but optimism based on thoughtful analysis of both large systems and individual behavior. Love your learnings, love your insights and examples. Thanks for sharing liberally and graciously, and Happy New Year!

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