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Well, it’s over. Sad face emoticon. The program that I had my eyes on for a year an a half, tenaciously applied to (twice), and eventually got the privilege to become a participant in came to a close last Thursday with an epic showing at Demo Day. As you can see, I’ve neglected my blog as things picked up early on. It’s a shame, but I hope to rectify things a bit with some reflections on my time spent at the #1 startup accelerator in the world.

I was a HackStar in TechStars. I got to attend all the sessions, spend my nights and days in the bunker, and even pop into mentor meetings if I asked a team to let me listen in. What I didn’t have was a company with a HUGE opportunity to show the world what they could do. In some senses this changes my perspective on the program, but in others it gives me a more fly-on-the-wall lens to see the whole shabang through.

There’s not much about TechStars I could say that is new and different, it’s awesome for all the reasons you’ve read about in 100s of blogs, but here’s a couple off the top of the head bullet points:

• Every session is worth attending.  I’m not an angel investor nor do I expect be one (at least not for a long, long time), but hearing what goes into consideration in angel investing helped me understand what an angel expects.
• TechStars prides itself on choosing teams rather than ideas.  It works and it’s incredible to see in action.  GoSpotCheck, a badass team with an idea that wasn’t working out scrapped the whole thing and rebuilt themselves into one of the top companies at demo day in 37 days.  They were living proof of how the picking teams vs. ideas mentality works.
• (My favorite) The camaraderie that TechStars inspires is one of the hidden gems of the program.  It’s the closest thing to freshman year of college that I’ve experienced in my 7 years since my freshman year of college.  Long nights of hard work with good friends and maybe a couple drinks…  I walked out of the program with a new friendships I’ll have for many, many years to come.

TechStars Boulder 2011

The actual name of this session was “All the stupid questions you wanted to ask about fundraising but were too afraid”. We had Brad Feld of the Foundry Group, David Cohen of TechStars who is also an angel investor, and Mark Solon of Highway 12 Ventures for a dinner session on fundraising. Questions (and answers) ranged from very general – What does Series A, B, etc. mean? – to very specific questions about specific investor-company relationships.

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“Raise the least amount of money to get you to that next step with the investors that will support you if estimated incorrectly”

“In any fair deal both parties walk away from the table feeling equally dissatisfied”

Mark Pincus (of Zynga) paid himself 32,000 a year for the first 2 years, minimum amount for a CEO in California.

Pay your team accordingly. If it costs 100,000 to prevent early talent from going somewhere else, that’s what it costs.

Another entry in my TechStars session notes. Brad Feld on being a CEO. (By the way, if you have any interest at all in startups, you should ABSOLUTELY be reading his blog).

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To previous CEO’s: What wasn’t awesome about being CEO of 10 persons company?

Not dealing with issues early on, classic problem.

It’s the CEO’s job to not run out of money. Front and center your job.

“If you the CEO, and the product lead, and responsible for money… you’re probably fucked”.

Mistake #1, CEO’s that wanna do everything.

“Having nobody that you manage as a cofounder is a very powerful thing”

Matt Van Horn spoke at TechStars and some of the things he said really stood out. I missed the first half of the talk, but even still I was incredibly compelled. Decided I’m gonna start taking notes on these session. Don’t read too deeply into them, they’re spontaneous, spur of the moment thoughts and it’s possible I misunderstood. Nonetheless, here they are (and will continue to exist in this blog’s notes category).

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Business development, VP at path.

Pulling from experiences with Digg and Path. Very compelling stuff about maintaining connections, following up, engaging in Twitter, Facebook. Considers IM to be a huge thing for developing a mentor relationship.

Hugely related to his uncomfortable feelings and chugging a glass of wind at a conference. That was my approach to SXSW.

“Just get 15 cards. Once you get 15 you can get the fuck out of there”

3 most interesting things about you.

We’re just over 1 full week into TechStars.

I have a very, very difficult time believing that sentence. At the end of last week I tweeted out that this is gonna be the longest, shortest summer of my life. Long days passing incredibly quickly.

After a week in I’ve gotten to know some of the teams, get the gist of some of the technology they’re using, and see how this whole startup thing works. It’s all made me feel pretty behind.

I came from an industry that doesn’t know what Twitter is. Foursquare? That sounds stupid. You went to South by Southwest? Is that a cowboy festival? As far as what was happening in new technology I was WAYYYYYY ahead of the curve in comparison to my coworkers. Now I’m in a room everyday where these things are not only the norm, they were the norm several years ago. The pace for keeping up has greatly accelerated.

I’m in the TechStars program as a HackStar, I’m suppose to help the other teams do more, faster. In alot (maybe most) cases they’re using products and technology that I’m not familiar with. Initially I felt kind ashamed of this – I should be better at helping out than I am right now – but after some thinking I realize it’s a tremendous opportunity. Where else will I get to spend 3 months in a room and learn cool stuff for 12 hours a day from some really smart group of people. After viewing this as a new approach to my technological deficiencies the HackStar problem has completely morphed for me in terms of what I’ll get out if it.

If this is a week in, I can’t wait for this time next week. Much less the end of the program.

Today was the inaugural session of TechStars Boulder 2011. It’s gonna be an awesome summer.

First impressions:

• Lots more excited about that teams after hearing elevator pitches, way better than a couple sentences written down
• David Cohen doesn’t say alot, but when he does it makes you think in a big way
• Truly impressed with how responsive every team was to feedback

It’s amazing how in one day the companies pitches had already changed. Can’t imagine what it’s gonna look like 3 months from now.  I feel lucky to be able to bare witness to it all.

When applications opened for TechStars for Boulder 2012 I had an idea but no cofounder. Knowing full well that TechStars selected based on team more than idea, I was at a significant advantage. Thinking that once again this wouldn’t be my year, I said “might as well put something in, hopefully they’ll recognize my name next time around”. Thought that was the end of it and that maybe the stars would align next year.

Sad Panda

Luckily, that wasn’t the end. I got an email back asking if I’d thought about being a HackStar, pointing me to the application. I hadn’t even heard of it at that point, but reading the description I knew it was a 100% fit for me. I amended my application and from that point forward I was gunning for a HackStar spot.

HAPPY PANDA!

I can’t tell you with 100% certainty what TechStars is looking for in a HackStar applicant, but I can tell you what I did and that it got me a spot.

I’d had several conversations with founders from previous TechStars classes. The one piece of advice that I heard time and time again was “show progress” or something else echoing that sentiment. Since I didn’t have an idea to progress on, I decided I’d work on whatever came to mind and continue to update the TechStars team with how it was going.

In the end, I’d exchanged 40 emails over with Nicole and David of TechStars, letting them know each little detail of what I was working at that point. I even put together a YouTube video of me demoing what I’d done in a short amount of time as well as a Google Docs spreadsheet with any project I’d ever worked on, how many users/view it had, and where it could be found online, etc.

Lots of emails

It’s pretty likely that only a fraction of what I had sent to TechStars was ever even looked at closely. Perhaps it was even overkill. Nonetheless, I think the fact that I was continually sending updates played to my advantage. I’d hesitate on whether or not to send an email or just continue to wait patiently, but everytime I did send them something I was always happy with their response, however small.

“Sorry for the amount of emails, just trying to stay in your frontal lobe (I think? I’m not sure if that’s the right part of the brain or not)” – me

“dude, you are full frontal (lobe). ” – David Cohen

It took some time (HackStars positions are decided after teams are chosen, about 1 1/2 moths after the app deadline in my case) but eventually I had my interview. When the offer came around, it was a no brainer.

Founder dating was awesome and it gave me a taste of what was going on outside of my 9-5 world. That being said, knowing about something and wanting it doesn’t necessarily make you qualified for it. The TechStars 2010 teams had been chosen and the program moved to the back of my mind for the time being. Work was going pretty well so I was content (happy, in fact) to keep doing my 9-5 and screw around with whatever side projects I could in my freetime.

CheckoutCheckins.com

Astdroid, a Kickstarter funded phone-in-space project

My most visited website got about 10,000 views and my most successful app has been downloaded about 4,000 times. Plenty of people working on stuff in their spare time have had far greater successes. Nonetheless, my “cred” seemed to slowly build. At first it was a couple tweets, then some emails asking to talk, toward the end I even had foursquare request my resume.

My intention in the onset wasn’t to leave my job, it was just to build cool stuff and put some ideas into action. The side effect of that was that I was proving that I could execute. Doing so began to attract attention from those looking for workers (particularly in the Android realm). It also had the added benefit of being a HUGE piece of the TechStars application. You have a lot more going for you when you say “I did this and this and this” then you do saying “I can do this, just haven’t yet”.

If I had only tinkered with projects that I made me money or granted me fame, I’d have nothing to show today. I did it all because it was fun for me and I wanted to. Pretty simple. It’s as cliché as cliché gets, but I worked on what I loved working because I loved working on it and the rest of the good stuff came as a consequence.

I’M GONNA BE IN THE TECHSTARS BOULDER 2011 PROGRAM AS ONE OF THEIR HACKSTARS! WAAAHOOOOO! (Humility is great and everything, but I can’t keep that one contained. So unbelievably excited.)

It’s been a little over 48 hours since I found out and just about 36 since I told my work that I’d be leaving.

Wooohooo!

This is a huge new adventure and I’m going to do my best to tell others about it via some blog posts here. It was invaluable for me to read others’ accounts of the program, so in the interest of reciprocating that I’m gonna post my own take on things.

One thing I want to make clear, I have absolutely 0 history in startups. None. At all. Whatsoever. I’ve worked the last 3 1/2 years in Defense and have done so since college. I wanted to make a change in what I did and had absolute no advantages, no prior experience, no connections, nothing but some determination (and an assortment of software skillz) to make it happen.

I’m hoping someone waffling on whether or not to go to that first meetup and (oftentimes awkwardly) stick themselves in a new community reads this and does it. Cause I waffled. And ultimately gave it a shot. And it changed my life.

You can’t always point to that moment in time when the butterfly first flapped it’s wings in Bombay and a rock slide was cause on I-70 (damn butterflies causing mountain traffic) but I’ve got a pretty good idea of where an event like that took place for me. It was TechStars Founder Dating in 2010.

A Lorenz attractor, a mathematical model of the butterfly effect

I learned about techstars about 2 years ago while busily coding in the defense industry. Some tweet lead to a blog, lead to techstars.org. Thought it was an amazing program and began reading what I could and following those involved. I saw an announcement for an event called “Founder dating”. I had been working on checkoutcheckins at the time and thought about finding a cofounder to take the idea a step farther (in retrospect, this wasn’t anywhere near the caliber of idea that would have made a respectable techstars entry, but hey, it got me there).

Went up to Boulder and made my first visit to the TechStars bunker. I was 100% solo. Didn’t know a soul. Met David Cohen without knowing at the time who the hell he was. When it started I regretted visiting because I felt so awkward. Then I had a beer and regretted it less. Then had another beer. By the time I left I was loving it.

Walked outta there having met some cool people, having had some cool conversations, and having making a particular connection with Rob Delwo. We made plans to get together and see what we could come up with.

Rob and I met a couple times over the next few weeks and hashed out a idea and for a TechStars application. Ultimately, we canned it recognizing that we missed a couple huge pieces. (At this point, the problem we were trying to solve still exists and I’m constantly reminded by others’ attempts that we were on to something, which is cool) It looked like being a techstar in 2010 just wasn’t meant to be. Oh well, no big deal.

Rob and I kept in touch. I let him know about whatever side project it was I was working on at the time and he let me know about people I should meet or get in touch with. As recently as last week he’d introduced me to the folks at Orbotix which lead to an impromptu interview.

Founder Dating wasn’t a mindblowing event, nor was it intended to be. In fact, there are probably hundereds of events like it. However, for me it was that first step down a new path that ultimately changed the direction of what I wanted to do with my life.

"You've taken your first step into a larger world"

So go. Seriously, just go. Go to whatever it is your thinking about not going to because you don’t know anyone and it may be awkward. If beer is available, even better. You’ve got no idea what it might lead to, but you’re 100% certain of what not going leads to – the same. And if you were interested in things being the same as always you probably wouldn’t have made it to the end of this post.

I like groupon, quite a bit in fact. I use it a couple times a month. It has some great deals.

The problem is I also use LivingSocial. And I use Denver Daily Deals. And I’ll likely have no problem using the forthcoming Google Offers.

And that’s why Groupon is screwed. The simplicity that makes these daily deals sites so great (I bought $80 of wine for $40 on a chair lift while snowboarding, WE LIVE IN THE FUTURE) also homogenizes them.

Daily deals websites aren’t like others on the interenet. You’re not using their service because you NEED it. Or because it does something others don’t.  Nor are you signing up for them because your internet social circle exists there. You’re just trying to score some sweet deals on cool stuff.

When each deals site offers the same stuff and provides a half-decent user experience, there’s no reason for customer loyalty to one as opposed to another.

Groupon did it first. I think (right now) they’re doing it best. I think the success they’re enjoying is deserved. However, it’s fleeting. Other deals sites will grow, Groupon’s momentum will slow, and in 3 years they’ll be out of business or wishing they’d accepted Google’s $6 billion. Or both.