Independence Day & Quicksand

On this long weekend celebrating our country’s independence, I’ve had the opportunity to reflect on the past couple of months since I left oneforty to work on my own startup.  It’s been good to reconnect with a lot of people who I didn’t get to while being heads down at oneforty, recharge my batteries a bit, and have some success in the cofounder search. That being said, I’ve also realized I’ve walked into quicksand…


On the football field, it’s when one thing after another goes wrong despite trying to make plays. In startups, it’s when you let something paralyze you and sink your entrepreneurial efforts. It might be because you focus too much on the wrong thing or ignore the most important thing.

I have tried to plan so many parts of this startup I’m now working on. Whether it be meticulously noting the learnings of the past year at oneforty, saving money so I can go without a salary for a very long period of time, or mapping out all of my contacts and the best ways to leverage them to succeed, everything has been carefully calculated.  I even focused on finding a great tech cofounder before the idea, so I was sure I had good alignment with them before we started running on an idea. All of this though ignores a key element: the idea. It is in this search for the idea that I’ve found myself in quicksand.

Searching for Inspiration.

Being calculated and focused is great for planning to save money and preparing to launch a company, but it’s terrible for trying to generate an idea. You can’t force inspiration.  I know this not for lack of trying:

  • Tried using David Skok’s brainstorming process he blogged about (coincidentally posted my first day after leaving oneforty).  It just left me feeling like a VC; knowing what are good, interesting industries, but not actually feeling like there was a specific idea to go work on.
  • Brainstorming with friends. I hit the white board with friends trying to flesh out some ideas, but only managed to write off a few ideas and failed in trying to dig deeper on ideas identified by using David Skok’s aforementioned process.
  • Talking with friends about the industries of their startups. I talked with a lot of friends in the community about what they were working on to see if any industries caught my eye.  Nothing seemed to spark.
  • Helping friends with their startups.  I tried helping a couple friends with their startups to see if I liked what they were doing (and might join them) or if their industries seemed like it had any interesting problems to solve.  The first two attempts yielded nothing and the verdict is still out on the 3rd.
I’ve found the harder I’ve tried to come up with the idea, the more I’ve sunk.

The Paradox of Choice

I feel a tremendous amount of pressure to come up with an incredible idea. A friend of mine mentioned over coffee that he hopes I don’t become Jarrod Saltalamacchia and it fits how I feel; Jarrod was a hugely touted prospect that came up from the minors and everyone expected he’d be the next great major league catcher.  As it turned out, he’s ended up being more of a journeyman.

I feel like I have to get a big hit in my first at bat and it has crippled me; everything feels like a non-starter because no idea feels “good enough.”  It’s also hard because the closest focus I’ve found is that I know I want to build a B2B SAAS company (mainly because I feel there is the most support and related companies here and I understand B2B more than consumer web.)

Digging Out

Realizing this is happening and admitting it feels like the first step. More importantly is what happens next.

David Cancel gave me great advice at RubyRiot that I haven’t heeded well to this point. He said, “save someone an hour a day and build a business around that.”  It also harkens back to the most obvious solution that’s been standing right in front of me the entire time: Customer Development.  Somehow, in all of this, I’ve done very little customer development (other than when helping friends’ startups).

What Now?

As a recent blog post said, “A lot of people talk about Lean Startups and customer development, but very few people really do it.” I need to get outside the f@&%ing building.

Here’s how you can help:

1) What sucks in your day to day or someone you know?

What makes you complain or you’ve heard someone say is horribly inefficient, and totally not in Web 2.0 and should be? I want to talk to you and/or them! Seriously, even if we don’t know each other, drop me an email at evanish.j [at] gmail [dot] com and tell me about your problem.

Don’t worry if you think it’s a boring problem; I in fact prefer unsexy problems. I’m hoping to solve a problem that doesn’t have 25 Valley startups working on it.  One of my favorite startups a friend is doing (not in Boston) is working in a space where his direct competitors are…call centers. That’s a fun problem to solve.

2) Got an idea you wish existed but can’t work on?

I’ve already talked to a few of you that have shared ideas where you said, “If I wasn’t doing my startup, I would do this.”  If you find yourself saying that, I’d love to buy you a coffee or beer and see if it’s something I can help make a reality.  I’m very happy to make you a beta user ;- )

3) Hold me to this.

Whether you have a problem or know of one I can solve or not, please hold me to this.

Don’t ask me how I’m doing next time you see me. Ask me if I’ve gotten outside the building.

8 thoughts on “Independence Day & Quicksand

  1. I’m envious of your position to take on new opportunities; and enjoying living vicariously through hearing about it! Just make sure you can stand behind the idea through the incredible number of hurdles (no’s) you will inevitably face.

    • Thanks, Punit. I love watching Zazu develop too (can’t wait to use it on my iphone!).

      That being said…that’s been a lot of my challenge…finding the right idea that does make me want to run through walls.

      • I hear ya. When I left Boston BookWorks I felt like I had too much free time on my hand with nothing to do. Believe it or not, I went to StartupWeekend 09 thinking I could find established startups to join. Glad I was wrong, but surrounding myself with ideas as you have been doing felt like being a kid in a candy store.

        Don’t let it bug you, it’s a luxury few people have!

      • “One man’s treasure is another man’s…” comes to mind. I’m too action oriented not to be frustrated by the process. I want to get busy executing on the idea!

  2. Hey Jason,

    Stumbled upon this post a little late I guess. Regardless, I just wanted to remind you that Jarrod Saltalamacchia is only 26 and while he once a top prospect he’s now starting for a team that has a legit chance to reach the ultimate goal (Winning the World Series.) He’s got a long career ahead himself and still can be great.

    So, to move away from the baseball metaphors – I strongly believe (for myself or anyone else) if you focus on working hard and remember to keep things in perspective, you may not “get a hit in your first at bat” (sorry couldn’t resist one more), but you’ll ultimately end up in a place with results you are truly happy with.

    So here’s to long and succesful careers regardless the outcome of the first attempt!

    • Sam,

      I appreciate the sentiment and certainly intend to be around for awhile.

      That being said, I’m not, “just happy to be here” as many first time call ups to the majors may say. I always set a high bar for myself and I just won’t be satisfied as a mediocre pro.


      • As it should be, but I guess I was trying to say – success can be reached in many different forms and ways. I certainly wasn’t trying to suggest that you should temper expectations or avoid setting high bars.

        Keep thinking big and working hard.

  3. (You might have solved this problem by, but if not….)

    I suppose people could say I don’t have the success under my belt to back it up (at least not yet), but my philosophy differs substantially here. A couple thoughts:

    -Forget customer development for this stage (but pick it back up shortly). What do you care about? Even if I gave you the perfect idea, would it be worth investing 4+ hard years if you didn’t really care about it? Those are precious years you’re giving up. My guess is that the outcome wouldn’t be to your expectations either.

    -According to my interpretation of the post, it seems you’re really stuck on having the perfect idea, which leads to “don’t think about white elephants” syndrome. Remember ‘evolutionary design’. Start with *something* and evolve it quickly by just starting to execute. (Getting ‘something’ is easy). Most people end up doing something very different than when they started right?

    -Use what you already know.

    -from an old blog post of mine: “People focused on the same topics tend to be highly networked. When you have a group of incestuously networked people, social recommendation causes the same ideas and impressions to be passed around. ”
    Are you exposing yourself to people beyond Web/Mobile startupers that read TechCrunch? Innovators in different spaces can be a valuable bunch, and you’ll find them in a variety of places.

    this is a tough, multi-faceted problem. if you really want some help getting this solved, let me know. There’s other ways I can help directly. (for instance, this is the perfect example of a problem that the Performance League was created to help solve, and I’m guessing they’ll be very happy to help.)

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