Roadmaps…If Only…

Fred Wilson has a great post up that every entrepreneur needs to read and think about. It got me thinking for sure.

Wired has a piece up now about Jeff Bezos and $AMZN owning the web. Trust me, that was not in his first year roadmap. Whispernet and the ‘Fire’ were likely not his ideas.

I wish having vision, passion and domain experience were enough. Nobody foresaw this last 15 years of technology change, which this cartoon captures in the most classic way.

I think success is more about appetite, attitude and flexibility.

If you are intense and patient and crazy enough to have a BIG appetite, you better be thinking of investors, family, friends and VC’s that understand your passion, craziness and industry vision. You better be willing to change course and you better be able to be smacked in the head…a lot.

When I started Stocktwits the idea was to build a financial idea network. In total I raised $60,000 just to flesh things out. We would start out by tagging stock ticker messages with $ and organizing them. Along the way, we have plumbed the idea network (the Stocktwits streams) far and wide. The ideas come at people in real-time and offer context.

I was not thinking about the ‘Technical Architecture‘ that Soren, Chris and Dustin would build and scale. I was not thinking of Twitter outages.

I was not thinking about how the ‘Investor Relations‘ departments at public companies could use it to disseminate earnings and other financial reporting.

I was not thinking about FINRA, archiving, compliance, API’s, the iPad, the competition, Droid and moving to Coronado.

Today, all I think about is how did anyone come up with such a dumb term as ‘Investor Relations’ for such an important part of the American economy.

Today at Stocktwits we look our 90-120 days with a pretty detailed roadmap. David Putnam has been teaching us a lot about process and timelines. But, David Putnam was not someone I knew when I started Stocktwits. I met him while pitching Stocktwits to Yahoo Finance. I can’t imagine going out further than 120 days because of pesky issues like revenue, financing, personnel, technology, competition…

It is hard to imagine being stuck in a Company big enough that has to have a detailed 12-18 month roadmap.

Today I just want to build a Company that allows me to have 20 (in a row), 90 day roadmaps with the freedom and flexibility to dream about 3-5 year plans.

If you want to do this too, start a Company. If not, find an entrepreneur that does and make it so that they want and need you.


  1. EduardoF says:

    Love this post… I couldn’t agree more. 

    PS: we met during TechStars, you gave our startup a nickname: ImmigrationBox, it stuck ;)

  2. Steve De Long says:

    Hi Howard,  Always love your perspective.  I have a clear picture of the big vision, why it’s important, how it makes money, but I’m starting with building a small slice of that vision.  And for me milestones are still measured in firsts. For example: First pitch in front of a crowd at Startup Matchmaker last week at Co-Merge here in San Diego.  So I’m looking forward to my first 90 day road map!  Fortunately, while I’m passionate and committed to my vision, I understand flexibility.  Entrepreneurship is a journey of discovery as much as anything else.  Thanks for the great post.

  3. Jevon says:

    You start off with no clue what you are really building, so you fake it a bit and create a big plan.

    Then you start building and you really realize you had no f$#$ing clue.

    Then you look back and you realize that you came up with your best stuff when you were naive and hustling, so you call it a “vision” and a “roadmap” because you realize there is no way you could do better now. Too much gristle,. too many wrinkles. 

    The real stuff happens in those 60-90 day sprints. The rest is like backdating stock options: you make things fit as well as you can.

  4. Chris Waldron says:

    As a first time startup team we always wondered if we were doing something wrong. We could never see more than 90 days out. As we progressed we realized that the roadmap is changing and that what we are building needs to be curated and mature before we can see what is next.

    Are there any great public resources to see how Stocktwits does product development/decision making around your roadmap?

  5. Jonathan Hegranes says:

    I like the idea of 90-day road maps, but also like how Bezos (as well as Jack Ma, and others) have essentially limited competition by executing 7-year missions — whereas most companies are battling out the 3-year battles…

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