Over the weekend I saw two more blog posts on this meme.  The first – by Fred Wilson titled Freemium and Freeconomics – is clear and well written (and free).  It’s then followed by an excellent comment thread.  The second – by Marc Cuban titled When you succeed with Free, you are going to die by Free (also free) is a muddy as Fred’s is clear (and the comments are much less interesting).  Nevertheless, both are relevant and insightful.

Whenever I see this meme rise its head, I think of a line I use whenever I consider an investment or an acquisition of another company.  “Would You Want It If It Were Free?”  I learned this from Len Fassler, one of my early mentors who acquired my first company (fortunately he decided it was worth more than free).  Before I made an investment, or support an acquisition, I sit quietly and ask myself “would I want this if it were free?”  By this, I don’t mean as a customer, but rather “would I invest in this at a $0m pre-money valuation” or “would I want 100% ownership of this company if it cost me $0.” 

Over the past 15 years, I’ve found my answer to this question to be “no” more times than I can remember.  It often surprises me when I realize this, as up to that point in the conversation, investigation, or negotiation I’d been focusing on “the deal” rather than “whether or not I perceived any value in the company being discussed.”  When I reflect on some cases that I remember, I realize how my internal rationalization machine had kicked into high gear as I got excited about “a transaction”.  By taking the transaction out of my thought process, I could focus on the essence of value (or lack thereof).

Of course I’ve been wrong (both directions) plenty of times.  But I can think of a bunch of situations where asking myself this question saved my ass or that of the company I was involved with that was considering an acquisition.

I realize this is a different version of free than the one Anderson, Gladwell, Wilson, and Cuban are discussing.  But, if you step back and think hard about it from a customer perspective, it magically becomes relevant.  Certainly lots of people “would try it if it were free”, but do they actually want it?

Our anniversary was June 21st and neither of us managed to get the other one a gift.  So – on June 21st we went trolling around the web for a piece of art to buy.  We each bought one and then decided to buy two more for our life dinner gifts on July 1st.  The two that we bought on our anniversary were Rick Dula’s – the first is R.I.P. Rocky Mountain News Building.

My world is all about innovation.  In the mid 1990’s, as the commercial Internet started to emerge and the World Wide Web became something that people both knew about and used, it seemed like the traditional newspaper (and traditional newspaper business) wasn’t long for the world.  While it took fifteen or so years for the real end game to emerge, I’ll definitely hang this one in my office as a reminder of how creative destruction works.

The other Dula that we decided to buy was D.A.M. Building Progress. 

This one is a big one – 41.5” x 55” – so we aren’t yet sure where it’s going to go.  Since we love to support local living artists, we’ll definitely try to find a spot for this other than “storage.”

Last night, at Ignite Boulder 5, I had a permagrin on my face as I thought about the amazing job Andrew Hyde was doing.  I first met Andrew a few years ago when we started TechStars – he basically volunteered to hang out with a video camera for free all summer to film stuff and learn.  He was so hugely helpful that it was easy to bring him on board the TechStars team in year two as the community manager.

I attended Ignite Boulder 2 and had a great time.  But last night – #5 – just blew me away.  700-ish people in the Boulder Theater, enormous energy, endless laughter and brain stimulation, and just a very good time.  Andrew organized a phenomenal show and really shined as the organizer / MC.

But TechStars and Ignite Boulder are not the only things Andrew does.  He also created Startup Weekend (I was at the first one in Boulder) and he was one of the founders of Boulder.me. And – with Matt Emmi of One Button -created the hilariously creative VC Wear t-shirt line (my favorite: “I went down on Sand Hill Road”.)

But wait, there’s more.  Andrew is everywhere in the Boulder startup community while managing to travel all over the world sharing his brand of entrepreneurial passion.  I don’t ever think I’ve seen Andrew without a smile on his face, and he’s even gracious when he kicks my butt in ping poing.

It’s been awesome to see Andrew come of age as a key driver of our local entrepreneurial community.  Good job man!

• Senior Software Developer
• Senior System Adminstrator
• Senior Web Developer

If you are Boulder-based and fit the qualifications, email Jenny-Lynne Elledge.

But – today’s silly patent popped up somewhere and I just couldn’t resist poking fun at it. Go Daddy has filed a patent for a method of selling equity in domain names.  I can’t wait to see what the SEC has to say about this one.

I sure do hope the new regime in Washington D.C. has the balls to address the software patent issue this time around and end this madness.

As my app portfolio continues to radically expand and I endlessly fiddle with placement, I thought it might be useful to reflect (and memorialize) the apps that are currently on my first screen.  Here’s goes – left to right, from top row to bottom row.

1. Calendar
2. Messages
3. Maps
4. IMExchange: Finally, someone got Outlook Task syncing with an iPhone app.  Worth the money.
5. Camera: Much improved – actually good pictures!
6. Photo
7. Weather
8. Kindle: Yes, I can actually read books on this.
9. Brightkite: I use this to post pictures to Twitter.  And occasionally log where I’m at.
10. Clock
11. 100 Pushups: Damnit – I will get stronger.
12. FlightTrack: Indispensible when used with TripIt.
13. Vlingo: Apple Voice Control is good, but Vlingo is great.
14. iPod
15. App Store
16. Settings
17. Phone
18. Mail
19. Safari
20. Tweetie: I’ve tried them all and this one is the best.

Page Two are my “less regularly used, but at least once a week” apps (like Fandango).  Page Three are apps from our portfolio companies (have you played Mafia Wars on the iPhone yet?  or Vampires?  or used your Pogoplug?)  Page Four is a bunch of random other junk, although I’m pretty aggressive about deleting apps I never use.

I wonder what Page One is going to look like a year from now?  Any gotta-have-em apps that I’m missing that you guys out there in blogland would recommend?

This week’s episode includes guest appearances from some of my closest friends, including Seth Levine, Jason Mendelson, and my Gist t-shirt.

Ian’s post is dynamite.  If you struggle to keep the pounds off, run (don’t walk) over to FistFulaYen, toss your Coca-Cola down the drain, and read “…look at me I’m skinny…”

As I whittle away a little bit of weight each week, I just keep telling myself “eat less, exercise more.”  As my weekly running mileage continues to creep up (I’m now steadily adding 10%+ / week to my base) it gets a little easier, but all it takes is one double large dinner and an extra big bowl of ice cream to completely wipe out the progress.

Ah, that tuna burger and truffle fries at Larkburger sure was nice today.  I guess that’s it for the week.  Thanks Ian for sharing what works for you.

I had another reminder of this as I cruised through my Daily folder.  The Astronomy Picture of the Day has been delighting me every day since I started looking at it a few weeks ago.  Today’s is a movie of Japan’s Kaguya spacecraft’s last moments.

Kaguya crashed into the Moon last week as planned.  Amazing.  We are small.

One of my goals is to be accessible to anyone that reaches out to me.  Another goal is to minimize the amount of time I spend on things that I either (a) don’t have an investment in, (b) won’t have an investment in, or (c) don’t have an interest in.  Basically, I want to “optimize my accessibility”.  This ebbs and flows – when I’m in balance I’m very happy; when I’m out of balance I’m still very happy, but notice that I’m out of balance.

One of the keys to this is to “say no in less than 60 seconds.”  Given that my email address is easily discernable, I get a lot of random inbound “we are looking for money” and “do you want to have coffee” emails.  These are easy to say no to, but I also get a lot of not-random “we are looking for money” (e.g. sent from someone I know) and “do you want to have coffee” (e.g. sent from someone I know or recommended by someone I know) emails.  And it escalates in relevance from there (and morphs into all forms, including breakfast, lunch, dinner, meeting, run, …)

Somewhere between 1% and 10% of these fit my a/b/c criteria above.  I can figure this out from the first interaction at least 50% of the time and my first email response is (hopefully a polite) version of “no” that usually consumes a total of less than 30 seconds from beginning to end.  Another 25% of the time I need a little more information and request it via mail.  This has the side effect of eliminating another chunk of interactions since the person on the receiving end never bothers to respond.  For those that do respond, I can usually figure out from the response whether or not I want to spend more time or not; if not, I’m still probably under 60 seconds for saying “no”.

The rest usually end up in more email interactions, a phone call, or a meeting. I try to limit all first meetings to 30 minutes so I don’t waste either of our time if it’s not going to go anywhere, although I’m not always successful at this (the wasting time part).

Now, lest you think this is “overstructured”, remember my goal: minimize the amount of time I spend on things I don’t care about which allows me to maximize the amount of time I spend on things I care about, while still being very accessible.  While I don’t always get this right, I’ve gotten a lot better at it over the past 20 years.

This is the June 12th eruption of the Sarychev Peak Volcano as photographed from the International Space Station (400 km above Earth).  Lest we forget, we are a very small species on a very small planet in a very large universe.  Try not to take yourself too seriously today – if you start, just ponder this photo.

The Founders | TechStars Boulder | Episode 4 "Skills & Persistence" from Andrew on Vimeo.

I’ve just spent the last 18 hours with my Foundry Group partners at our quarterly retreat.  This is an approximately 24 hour affair that includes staying overnight somewhere in Colorado within driving distance of Boulder.  We’ve been doing this quarterly since we conceived of the idea for Foundry Group.

Our retreats aren’t “portfolio review sessions” nor are they complex travel boondoggles.  They are a simple, focused, 24 hours away together to discuss our business, reflect on how we are working together, and explore ways to improve things.

In Feld Technologies (my first company) I used to do this monthly with my partner Dave Jilk.  We lived in Boston at the time so we had our retreats within driving distance of Boston.  Same drill – leave in the morning of day 1; return in the afternoon of day 2.  Spend the time talking about our business and how we were working together.  Deal with any hard issues head on and try to figure out what we were going to do about them.  Dave and I managed to do this 10 out of 12 months a year (we’d occasionally miss) but when I think back on Feld Technologies, these were some of the most important and satisfying times we spent together.

While my life is frenetic, the world around us is chaotic, and as I like to say “something in my world somewhere is totally fucked up every single day”, I generally achieve a very deep calm.  On the surface I appear to be extremely busy, but at my essence I hear the birds chirping and think of fields of golden retriever puppies.

I woke up thinking about this and realizing how incredibly powerful it can be.  The lights on one’s existence go out suddenly and often unexpectedly.  There are endless (and daily) twists and turns in the path to happy, whatever you define happy as.  I’ve often said anxiety and fear are useless emotions in most contexts; a deep calm helps counteract them when they arise.

I encourage you to ponder this as you go about your day.  Time for a run.

Dan Putterman sent me back a response that included words like UPnP and Rendezvous along with a link to OpenPogo – a new website aimed at “getting the most out of your Pogoplug.”  The super cool thing is that Cloud Engines has nothing to do with this site – it was created by a user / fan / hacker that is building a series of guides for getting the most out of your Pogoplug.  For example:

• OpenPogo-Base Installation + Package Manager: You need the package manager installed as a starting point.
• Web server: Lighttpd (and PHP): How about a Web server on your Pogoplug.
• MySQL: Installing MySQL on your Pogoplug!

Extremely cool.