One year ago today a startup was born
This morning, my roommate Jonathan Woodard and I woke up at 6:00a, and without many words, got dressed, walked out to my car, and made the drive out to Mapleton & 30th for our 6:30a workout at Crossfit Roots. The workout was especially entertaining: 100 burpees. Stand up straight, lay down on the ground so that your chest touches, stand back up, jump up in the air, and clap your hands your hands above your head while you’re in midair. Do that as fast as possible. 100 times. Jonathan and I both finished in just over 9 minutes.
We got back in the car and, still with few words, anxiously awaited getting back to the apartment to massacre some veggies, sausage, bacon and eggs. During the massacre, Jonathan speaks up (we had finally woken up), “Hey so 4sq & 7 emailed me this morning. It was a weird series of checkins a year ago today, and then I figured it out: It’s our 1 year anniversary.” One year ago today, Jonathan and I were at Walnut Brewery and discussed, for the first time, working together.
I arrived via U-Haul, Volvo in tow, in Boulder on August 2nd, 2010. Jonathan got here the day before me. We didn’t know each other. For the next several months, we kept seeing each other at events all over town. I would see him on Twitter and at Atlas. I would wonder who this guy was at BOCC being even louder than me. Eventually we met, started talking, and one night while out at the Walnut Brewery for dinner, I asked him if he wanted to create a startup together. In between staring at the cutie waitress, we decided to go for it. “Let’s see what happens.”
One year ago….
And with that, we were off. We looked at, and in most cases prototyped, a lot of ideas. I can think of at least 5, but I don’t rule out the possibility I’m forgetting one:
- an app to help plan ski trips
- an app to help buy consumer electronics
- a social widget that gave online retailers insight into the minds of their customers at the point of sale
- an omniscient browser extension that would monitor what you’re doing online and automatically let you know when those in your social circle had previously done something similar
- our current project, which isn’t exactly a secret, but not something I’m ready to blog about
A lot happened in the past year. We looked at raising money, met with VCs, had discussions about a potential merger with another fledgling (but better capitalized) startup. One product came to fruition (the 3rd one in the list), launched at BDNT and Boulder Beta, got some early users, but never panned out as expected. We haven’t given up on that social insight widget, but it’s on the back burner for now. The omniscient widget idea started to get prototyped, but after consulting with some very smart people around Boulder, we decided it just wasn’t something we wanted to pursue right now. We applied to TechStars twice, once in Boulder and once in NYC. Obviously, we were not accepted. We also never raised money, and never merged with anyone.
Throughout the year, we flirted with bringing on a third founder 5 times. The first four didn’t pan out, and we were lucky in that all the business relationships ended amicably and left the personal relationships intact. For us it’s turning out that the fifth time is the charm. Alec Uitti, a designer with a ton of experience, joined our team a few months ago, and we’ve been plugging along ever since.
For the entire time, Jonathan sustained himself as an independent contractor. I was working for Punchbowl.com until May of this year, and have been working as a contractor since then.
So one year later we have no revenue, we have no product, we have raised zero dollars, and while we’re incredibly excited about what we are working on now, there is as of yet no guarantee it’s going to work out.
So how do I summarize the last 12 months? Was it a waste? Have we been spinning our wheels? Are we stupid failures?
Hell no.
For starters, we’ve learned one of the most important things that founders can learn about a partnership: that we can work together. Jonathan and I share a lot. We work together. We live together (he moved into my spare bedroom in January 2011). We fly in similar social circles. We are both in the same ski house up in Vail this winter. We both hang out at Atlas Purveyors. And as mentioned at the start of this post, we workout together at Crossfit Roots. I’ve yelled at Jonathan. He’s been furious at me. I’ve apologized. He’s apologized. We’ve gotten very drunk together. I’ve tried to give him a haircut while he was brushing his teeth one morning. He’s videotaped me throwing up. We haven’t killed each other yet, and we (probably) won’t in the future.
We’ve both gotten a hell of a lot smarter and more pragmatic. There’s something to be said for biding ones time in search of the right idea. Any business takes a little bit of luck to work, but you can maximize for luck by being smart about how you select an idea, and we’ve gotten better at that. Any one of the ideas in that list above can be made into a successful business, but for one reason or another, none of them are right for us right now.
One of the most interesting things I’ve noticed is that we’ve ‘settled’ into Boulder. When I moved to Boulder, I didn’t know anybody. I was alone. I attended every event I could, I talked to people, and I reached out to strangers. But it took over 2 months before I ever got invited to go socialize on a weekend (thanks Chris Hough). Once I started to make real friends here, I wanted to make the most of it: socializing all over the place, never turning down an invitation or a public event, tweeting at everyone constantly, watching the Bachelor & Bachelorette at Alpine0210 every week (thanks Joni & Alexis!). Back in March, when I was finally about to give my notice at Punchbowl, I didn’t have much of a savings. I went out to the Mountain Sun with Chris Rosen (owner of Atlas Purveyors) and told him I was pretty scared. He looked at me, smirked, leaned in, and as he looked left and right around the room, said “Dude… you’re here.” He didn’t mean the Sun dining room. He meant Boulder. He meant the community; the family. In just a year, I really have come to feel like I’m a part of it. I feel safe here. And with that comes the ability to be comfortable putting my head down for 3 weeks and not socializing or trying to make new friends.
So now, after a year of doing what we’ve been doing, this is the state of things: We have a killer idea that fits us — and Boulder — perfectly. We have the skills to build it. We have enthusiastic early users with cash to spend. We have advisors that I trust in and that believe in us. We trust each other. We’re working our asses off.
For the past year, Jonathan and I have been working in a startup: a temporary organization built to search for a business model. After a year of doing that, I feel more ready than ever to turn this startup into a business.
So here’s to the next year, Woodard. Let’s go knock this out of the fucking park.

Mea Culpa? Me-a bummed out.
It’s a bummer that Mark Suster was bullied into this:
http://www.bothsidesofthetable.com/2011/08/24/mea-culpa
It’s a bummer because his original post (here) was brilliant. It was even-tempered, rational, and necessary. The dozens of FNAC corporations that get bought each year and get plastered all over TechCrunch are poisoning the minds of current, past, and future entrepreneurs - mine included.
I’m not saying there is no value in FNACs like group messaging services GroupMe & Beluga. There clearly is value; it’s apparent in their acquisition. But that does not make them a business. They are a cool set of features with some cool tech, great vision, and a talented team. Everyone on those teams deserves what they got in terms of cash and equity.
It’s admirable to take a chance on some cool new technology (I’ve done it twice) but to do it under the guise that you’re building a real business like everyone else is a tragedy (only did that the first time :) ).
I think we all could benefit from the wake up call that Mark gave in his original post. There is a difference between a Feature and a Company. Make sure you know which you’re getting into.
Required reading: http://www.bothsidesofthetable.com/2011/08/22/fnac-feature-not-a-company/
A great funding presentation from Mark Suster
EDIT: I’m sorry about the weird whitespace in this post. Tumblr or DocStoc insists on injecting some iframe that I can’t get rid of. #nerdrage.
I really like this guy:
How to run a startup (Or why I just got a man crush on David Karp)
Yeah.
We roll out changes to the site every day at 11 a.m….
After we launch a new feature, I keep a close eye on how many people are using it. If it’s unpopular, we’ll discontinue it and try something else. Every feature has some maintenance cost, and having fewer features lets us focus on the ones we care about and make sure they work very well. For every new feature we add, we take an old one out.
Holy crap.
This is how a startup should be run. I love every single sentence in this article.
One of the things I love most about this article is the pragmatic nature of it. It’s just a series of statements with no attempt to be poetic or egotistical. It’s just David saying “Here are some bullets points on how I run my company and why.”
Damn, David Karp. I salute you.
Seeing the country for the forests

“…we were struggling to make sense of the bubble and its aftermath, what it meant for technology and what it meant for venture capital.”
-Fred Wilson
This quote from a recent Fred Wilson blog post reminded me of something I’ve been going through lately.
I’m out in the world. I have a “neat idea.” I talk to a lot of people about it. I get lots of wide eyes and “whoas” and great feedback. After months of searching for a great idea, it’s easy for Jonathan and I to rest on our laurels and think “well that was hard, but we worked hard and talked to a lot of people and did a lot of research and we finally got it.”
Not so fast.
Now that we have a product, Jonathan and I have to figure out what it really means in the grander context. Where does it go? What is the future of the product and the brand? These are questions similar to what Fred was talking about in his blog post: what do we go from here?
When I first saw Square, I thought to myself: “Thank you, Jack!” But I also thought to myself “hrm that’s nice… buuut is that it?” I wondered what would be next for them. What’s next for them is Card Case, and while the fantastic design of Card Case is a shining example of seeing the forest for the trees, the evolution of the Square payment platform from ‘just’ Square to Square + Card Case is a level higher: it’s seeing the country for the forests.
Square is not just building a product. They’re building a company with a greater hunger and vision. That’s something I am looking forward to doing with FourthSegment. I’m looking forward to reminding myself constantly to never stop thinking about the bigger picture; to never stop seeing the country for the forests.
Now hopefully this blog post will do its job and help me remember that ;)
FourthSegment Blog: Welcome to the FourthSegment Blog
Check out what I’m working on next:
Hi,
I’m Ryan Angilly, and I, along with my business partner Jonathan Woodard, want to welcome you to the blog for our new company, FourthSegment.
Back in November, Jonathan and I started to ask ourselves: What’s the next big thing? What’s coming down the pipe that is going to…
We moved to Boulder and….
Let’s face it, people: Boulder is a pretty awesome place. I knew that before I moved here — to be honest I knew that before I had ever even been here. But I was still blown away when I got here to see what a welcoming community this is.
For months after moving to Boulder, I kept meeting people who also just moved to Boulder. People starting companies; people speaking at Ignite; people creating works of art on the chalk board at Atlas Purveyors; people speaking at local developer and business meetups. It’s a town where if you have the right mindset, you’ll just fall right into place.
So when I was asked to come up with an idea for a Boulder Startup Week event, it wasn’t too difficult
So!
On Friday, May 20th from 5-7p at InspiringApps, some of Boulder’s most recent freshman class (with some sophomores and juniors thrown in for good measure) will gather to share their stories:
- Why they moved here
- Where they came from
- How quickly they got plugged in
- How awesome the ride has been
- What they’re up to now
If you’re attending BSW from afar, check out this event. Feel free to reach out to me with any questions you have.
If you’re in your first year or two here in Boulder, want to wear a fancy a name tag, and don’t mind sharing your story, get at me over email or twitter.
I attended Gluecon last week. It was awesome. I had a phenomenal time talking to some really smart people. While I was talking to someone at one of the demo booths about 
