2011 was…

the year I got a dog.
the year I asked Alex to marry me.
the first year I went to SXSW.
the first time I visited Europe.
the year I hired my first employee.
the year that the DC startup community blew up.
the year I got involved in community building.
the year I spent way too much time in airports.
the year that I finally dropped everything to pursue a grand vision.
the year that I first raised outside funding.
the year that I built a team.

ProudlyMadeInDC Turns One

One year ago today, we launched ProudlyMadeInDC. I sent out this message to our mailing list

In the wee hours of the morning, on December 2nd, 2010, the two of us
started throwing together a simple WordPress site, after a dinner discussion
with other entrepreneurs about improving the scene in DC. We posted a list
of startups that we knew about (a total of 40!), and shared it with a few
close friends. On December 13th, 2010 – we opened it up to the world. And by
“open it up” – we actually mean making a couple tweets/FB posts. We expected
maybe a couple hundreds hits to the site, and eventually it would just trail
off and disappear.

But you, the community, latched on to it. You took what we built, and ran
with it, turning ProudlyMade into something we could never have imagined.

More importantly, we’ve seen the community grow. While we could focus on the
birth and growth of so many follow-on efforts (DC Tech Meetup, DC Tech
Summer), as well as dozens of other resources coming online in the DC
area… That doesn’t matter. What matters is that every day, more and more
people are seeing that realizing their dreams is possible in the DC area.
They’re escaping their cubicle prisons, working nights and weekends,
validating their ideas, raising funding, and building companies. We’re
creating jobs and making the world a better place. Sites like
ProudlyMadeInDC, events like the DC Tech Meetup, and thousands of other
resources, meetups, and groups… we’re just here to support that. Just a
few years back, would anyone have dreamed that DC would be a place where
hundreds of startups would bloom? We certainly didn’t. Yet here we are. DC
is on the map. And you are making it happen.

So here we are – roughly a year after launching, still going strong. We’ve
established ProudlyMadeInDC as a home for entrepreneurs helping
entrepreneurs. We work 24/7 on our own startups (it’s currently 1:30
in the morning as we write this), and try and put whatever remaining time we
have into helping you. Going forward, we’re going to be adding more
resources, both internally and on our site, with the aim of helping you. So
thanks.

Oh yeah, we’re throwing a little party too.

Cycles

I had an idea.
(repeat 1,000,000x)

I had an idea.
I wrote it down.
(repeat 86x – based on Evernote usage since August ’09)

I had an idea.
I wrote it down.
I talked to a lot of people about it.
(repeat ~30x)

I had an idea.
I wrote it down.
I did a basic landing page, or mockups.
(repeat ~20x)

I had an idea.
I wrote it down.
I did a basic landing page, or mockups.
I told everyone I know.
(repeat ~3x)

I had an idea.
I wrote it down.
I built a prototype, 90% of the way there.
(repeat ~20x)

I had an idea.
I wrote it down.
I built a prototype.
I finished it.
I opened it up for the world to see.
(repeat ~5x)

I had an idea.
I wrote it down.
I built a landing page.
I told everyone I know.
I built a prototype.
I told everyone I know.
I pitched it all the time.
(repeat ~1x)

I had an idea.
I wrote it down.
I built a prototype.
I told everyone I know.
I pitched it everywhere I could.
I assembled a team.
I wrangled advisors.
I dropped all other  professional distractions.
I got us accepted into an incubator.
(in progress)

The Perils of Bootstrapping via Consulting

Since the last startup I was CTO of was acquired in 2009, I’ve been working for other startups and agencies as a consultant. While my main goal in life is to be building startups that I am the founder/co-founder of, consulting has been a great way to pay the bills while I iterate with different products, ideas, and people, figuring out the next big thing to throw myself into with all my heart. Everyone talks with great praise that taking on consulting projects while running a startup is a great thing – avoids outside financing and lengthens your runway.

There are real problems with consulting

1. You only have a limited amount of time during the week. Consulting takes time out of your day. What is your most precious resource?
2. When you’ve blocked a certain amount of time to work on your startup, when a client calls with a burning question or meeting, it’s a distraction.
3. Consulting encourages jumping around. I can on some days be juggling 8 or 9 different consulting projects, and have learned how to switch quickly. That is the complete opposite of a startup – where a laser focus.
4. The short-term opportunity cost of working on your own internal startup increases tremendously. When you’re being faced with the choice of “Do I work on my startup, with some chance of success in the future” vs “Do I make some good money right now” – and you’re being asked that every minute of every day, committing to your idea becomes even more challenging.
5. The biggest flaw. When you hit a rough patch with your business (bad feedback, lack of interest, technical challenge) and that little seed of doubt starts to grow… it’s effortless to take a few more consulting gigs, and before you know it, it’s been months since you’ve cracked open the code base.

What I do to prevent it (and I’m not perfect)

1. Break up both consulting work and internal startup work into manageable chunks. That way you can mix both together in a day.
2. In true GTD style, write down what you need to accomplish before you start your day. It’s at that planning stage where you can put thought into how you want to balance your day.
3. Don’t check email so often.
4. Hire other people to work with you. Task one of you with with client work, and the other with internal product.
5. Keep track of your financials. How much consulting work do you actually need to take in this month?

What I’ve seen other people do

• Block off a certain part of the week/day for client work, and part that’s just for startup work. Don’t even think about picking up the phone, or having a meeting
• As your team grows, you can have people focused entirely on internal projects, that will never touch client work.
• Magically find a product idea that your clients can pay you to build, and be your first customer

Don’t get me wrong, I love me clients. But we all know that consulting for an entrepreneur has to be treated as a means to an end.

A Solution to A Community Problem

The past sixth months we’ve seen an explosion in the DC community. Events where we normally may have expected a few dozen of the same faces to show up have now grown into the hundreds. There seems to be this constant flow of new people, new companies, and general enthusiasm around creating new ventures in the region. We’re hoping that this becomes self sustaining, and all signs point to that being the case.

With such a large community of new individuals, new challenges arise. We keep an ear open to every bit of feedback, and there is one constant piece of advice. The people sitting in the audience want to know each other, above all else.

Michael and I, and numerous others, have talked at length about this, and I’ve condensed this into a few hypotheses.

• A community relies on 1:1 connections – I can honestly state that, over the past four years of networking events, dinners, drinks, and coffee – I’ve been able to both give and receive the most amount of value by sitting down – in person – with one other person. Getting to know them, learning what they are up to, and figuring out actionable next steps to help each other out. I’ve made clients, friends, and business partners this route.
• Large events don’t provide the right atmosphere to facilitate real connections – When I walk into a large networking event, I maybe walk out with one or two people I’d actually be interested in talking with. Now, my tendency is to gravitate towards the people I already know, and just chat with them. I’ve heard how daunting it is, as someone who doesn’t know that many people, to walk into a room of 700 people, and not know who to talk to, or how to.
• Existing social platforms aren’t built for discovering other people – The initial use case of Facebook (I was in college at the time) was exploring and connecting who was in your classes, and who your friends were friends with. Over time, privacy and new features have all but destroyed the ability to connect with people you wouldn’t know otherwise. Even the groups feature isn’t conducive to connections amongst its member. Twitter’s utility as a discovery decreases with each new member being added… more noise.
• Social context isn’t necessarily the solution – Just because you’re in the same group on Quora, checked in to the same venue on Foursquare, or “like” the same social objects – doesn’t provide enough data to ensure that some kind of meaningful connection will happen.
• A platform purely focused on people discovery can serve many purposes. I’ve seen the value of connecting with others, and facilitating further connections between others. An online solution to facilitating offline connections has value.

That being said…. keep your eyes open. We’re working on something.

2011 Washingtonian Tech Titan

I’m honored to be on Washingtonian’s list of Tech Titans this year.

Onward and upward.

The DC Tech Community – Why I’m Doing It

It’s been a little under five months since we launched the first version of ProudlyMadeInDC, a website that has helped shed light on the growing startup community in DC. It’s received more media attention and traffic than I expected when it was built. Since then, we’ve launched two additional initiatives – the DC Tech Meetup (800 attendees expected for next week) and DC Tech Summer (over 400 interns applied in one week). ProudlyMade remains our flagship destination, as well as the biggest time commitment.

In terms of hard costs, PMiDC is relatively cheap. It is however a huge time commitment. We have companies to review and add all the time. All day long, entrepreneurs, VCs, and established companies are reaching out to us asking how to get involved, to vet their ideas, and what they can do to help the community. It is an incredibly exciting thing to do, but when you’re building a startup while already running a successful business, and in general trying to find time to enjoy life a bit, the opportunity cost is high.

So why do it?

Really simple:

Main Reason: If I can do everything I can to make DC a great place to build and grow a startup, then that increases the chance that anything I create here will succeed. I could move somewhere else to do that, and that’s never out of the question, but I’m here now.

Secondary Reason: These are my friends, coworkers, collaborators. I’m lucky to personally know so many awesome founders in the region. As anyone who’s been in an entrepreneurial community for a while, the peer support is amazing. This is one of the best ways I can think of supporting the community.

Secondary Reason: I started out in the community knowing no-one, and am always out there to discuss ideas, work through problems, and figure out the best way to help each other. I want to know everyone in the community, to work with them, discuss ideas, maybe get funding. Having a central role gives me that visibility into the community.

I’m Not Doing it for Money: Sure, I want my startup to succeed and be profitable. But I’m not here to make any money directly off the community. A lot of people, after an article is published or a big meetup, will reach out to me inquiring to me about my services. I’m not accepting new clients at this time, no matter how much you ask. That being said, as our initiatives grow and become more of a time commitment, that may change in order to better balance our time.

What’s Next:

We just had a great meeting yesterday regarding the next steps in the community, and have a product in the works to support it. Just wait and see. People Discovery + Social White Pages FTW.

Advice When Looking for a Technical Co-Founder

It’s been great watching the early stage startup community grow in the DC region over the past six to twelve months. Companies are getting funded, new ventures are being created every day, and on the whole, the entrepreneurs in the area no longer feel like lone wolves wandering around with no support network. As I’ve become heavily involved the mechanics of the community, through founding/co-founding ProudlyMadeInDC, DCTechMeetup, and Hackers/Founders, I’ve had a chance to speak with dozens of early stage companies. While the company may have an excellent founder, a great idea, and on occasion some seed funding, more often than not I hear the same thing:

“I’m looking for a technical co-founder.”

It’s a completely understandable situation to be in, putting myself in a non-technical persons shoes. You have a strong idea, (usually) a specific product roadmap, and a great marketing plan. All you need is someone to jam out some code in a weekend.

Limited Supply
The biggest issue in the market today is the extreme dearth of good, experienced developers. Even then, the good ones already have jobs, either at startups or large corporations with six-figure jobs and free cake once a month. And the more entrepreneurial types (referred to as hacker/founders) – most likely they’re already working on their own concept.

What do you offer?
A good developer knows their value in a startup. After all, they’re the ones who are actually building the product everyone is betting the farm on. In return for them getting payed a meager salary (or just equity), working 60+ hour weeks, and dealing with a plethora of product changes, users, system downtime, and all the other fun stuff with being the sole/primary developer, what do you bring to the table? What’s your track record? While they are building everything out, what are you doing? With them sinking so much sweat equity into cranking out code, what assurances do they have that you won’t just lose interest and walk away?

Here is some advice that I give out when I hear that line:

• Refine your product vision: If you still think that “MVP” is a sports term, spend a good amount of team going through the plethora of content related to Eric Ries’ lean startup methodology. A good chunk of the lean startup dogma is devoted to refining your product down to the absolute minimum necessary in order to gauge interest and, hopefully, revenue. When I’m handed a twenty page spec document split up into five phases, I always try and boil it down to the most basic, ugly, product that shows that it’s worth someones time continuing to build it out.
• Learn to code yourself: I’m sure I lost half the audience just by saying that. Some find too large a gap between someone who can architect software and someone who… tells them how to do it. But in truth, the difference is smaller than you’d expect. I’m not saying that you should expect to overnight become a master codesmith, but it’s certainly within your realm to learn enough Ruby on Rails (or PHP, Node, etc) to be able to crank out an initial version of what you’re trying to build. The documentation is plentiful, classes are always available, and due to the magic of open source software, there is a LOT of code that you can look at, learn from, and repurpose. Before you skip on this entirely, spend an hour starting off with http://hackety-hack.com/
• Hire a Team – So you’ve given up on coding it yourself. But if you have a very strong idea about what you’re looking to build, it’s certainly possible to get a decent product by hiring outside designers and developers (heaven help you if you think you don’t need a developer…). This should at least get you an initial prototype, and hiring a local developer to help support it and make changes can be done for a lower price.

Are you a developer?
OK, you might be reading this and happen to be one of the developers that everyone is looking for. If so, get in touch with me, right now. I’ll set you up.

HeyAstro: Dropping Everything and Jamming for 16 Hours

When Mike IMed me a few months ago to ask if I would join him and Kunmi for StartupXLR8R, I resisted at first. I am already focusing so much time on STRUCTO, and already distracting myself with side projects like WhoMails.Me and ProudlyMadeinDC (the latter of which Mike is a co-founder), that another project would be too much to handle. But we approached it with a different spin. While we all had our own startups, and all the other teams applying were for the most part well established startups, we were going to go from zero to launch. In two days (16 hours).

We had tossed around a number ideas, but ended up choosing a smaller idea that we knew we could launch an initial version of by 4 PM Sunday afternoon, when it was time to pitch our product for “investors” (not that we had any interest in raising capital for this). We settled on an idea I had, a daily e-mail customized for you.

So Saturday morning, we headed off into our breakout room (thanks Microsoft for an absolutely gorgeous space), and just started cranking out code. Kunmi worked on the frontend display, Mike on the email and configuration backend, and myself on all the data sources. It was an exciting weekend, with sixteen straight hours of heads down, don’t-talk-to-us coding.

By 3:59 PM (we were pushing code as we were walking into the conference room), HeyAstro was born. In the few days since we’ve launched, we’ve had over 150 people sign up, an immense amount of amazing feedback, and a laundry list of new things we want to do with the product.

Sign up for HeyAstro, and let us know what you think!

Final Stack:

• Ruby on Rails (#FTW)
• Heroku for Hosting
• Delayed Job for Queue Management
• SendGrid for email delivery and analytics
• Gems, Gems, Gems. There is no way we could have built this in any other language than Ruby, as so much of the backend relied on particular gems. Koala for Facebook, HttParty, Instagram, OAuth etc…

Presentation at DCPHP on PHP/AWS/Rightscale

In February of this year I presented at the DCPHP meetup. Based on my experience deploying large client applications built in PHP using AWS and Rightscale, I gave a detailed walkthrough of how to set it up. Fuzzy video below: