all posts tagged 'goals'

Coaching for Demo Day

🔗 a linked post to » — originally shared here on

So then I asked him: what kind of VC does he actually want on his cap table (that is, owning a portion of his company)? What would be true of the sort of investor who really gets him and resonates with what he’s building?

The same question applies here as on a first date, I pointed out: do you want them to fall in love with you, or with a fake version of you that you now either have to maintain—at the expense of the person you actually are and want to be—or else face irreconcilable conflict and disapproval when you finally drop the facade?

You want to reach the investors in the room who want to flame-spot audacious and idealistic young upstarts like you; who’ve staked their careers and reputations on the thesis that the world needs more of just the kind of company you’re building; who resonate so hard with your story and are so wowed by your talent that they’ll be willing to invest in, nurture, and protect your agency as a founder.

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Goals (Summer 2018 Edition)

originally shared here on

Back in 2011 when I started this blog, I wrote a post that outlined some short and long-term goals that I had for myself.

I came across that post while re-doing this blog, and I thought that establishing some new goals was a worthwhile task.

For the past few years, I've been using an analogy for setting goals that I like to call "the swimmer's approach", which I came up with while watching triathletes swim during a race.

When you're swimming a fairly long distance, there are times where you need to put your head down and swim hard, and there are times where you need to lift your head out of the water and make a plan to head in a certain direction.

The key here is to combine both as efficiently as possible. If you're just heads down swimming hard all the time, you'll likely start veering off course considerably. Conversely, if you are spending all your time looking off into the distance, you'll never get there.

So today, I'm focusing on getting some new goals. Here's what I've got:

Short Term Goals (by August 15)

  • Completely unplug for a week and enjoy time with my wife
  • Take Charlee to a place she's never been before (like a new splash pad or the science museum)
  • Come up with a sales strategy around our long-term support plan for JMG
  • Finish the Siri integration with my weight tracking app
  • Watch 3 movies on my Plex server
  • Walk around the block without crutches (0.5 miles)
  • Write another blog post for this site

Medium Term Goals (by December 31)

  • Set a budget for marketing at JMG and launch a campaign
  • Close a large sale
  • Merge Rob's project management app (Triangle) with my sales and marketing app (Gil) and give it an awful name (like Trian-Gil)
  • Get the average subscriber count for Constant Variables up to 100 per episode
  • Get version 1.1 of released
  • Watch 30 movies on my Plex server
  • Go for a 1 mile run
  • Brew my first batch of beer

Long Term Goals (by July 1, 2023)

  • Run another marathon
  • Build up a 6 month emergency fund for the JMG
  • Move to Wisconsin
  • Have an event with one of our businesses
  • Have another kid
  • Finish watching all the movies on my Plex server (currently, I'm at 600+)

Now, it's time to start swimming.


originally shared here on

It sounds obvious, but for me, the most difficult part of graduating from college is figuring out what to do next.

I feel like I've spent much of the last year wandering aimlessly, trying to figure out what it is I want to do with my life.

Right now, I have two projects going on simultaneously:

  • Trying to start my own video production company, producing videos for commercials, TV networks and bands

  • Trying to start an iOS development house, creating iOS apps for local governments

"Trying to start."

That phrase pretty much sums up what I mean by "wandering aimlessly." I feel like I've done some of the work needed to get these businesses going, but I don't feel like I've settled on exactly what I want to do.

After contemplating what it is I want to do now that I'm done with college, I decided I need to start making both long and short-term goals to get me to where I want to be.

Therefore, I'm making a few of my short-term and long-term goals public so that I can be scrutinized by friends and family throughout this holiday season, as well as motivate me towards a future that I can call "successful":


  • Learn Objective-C to a point where I can make a simple camera application that sends pictures to a specific server
  • Practice different Final Cut Studio tutorials to learn new tips and tricks


  • Build a solid business plan that outlines what I want to do for the next 20 years
  • Decide the camera workflow I want to use for the next 5 years and begin investing in it
  • Pick a name for the businesses and establish an LLC for one (or both) of the companies
  • Use this blog to post about things I care about, both professionally and personally

Lastly, my biggest goal for the next year is to have an answer to the question: "Where do you see yourself in 10 years?"

(I apologize if it seems like I just rambled in that post. It's been a while since I've blogged.)