One of the bigger lessons I learned over my time in Boulder at TechStars was this: Don’t Suck at Email. Now that I consider myself to be quite good at email, it pains me to see people suck at it. And the sad truth is that most people truly suck at email. This was a topic we discussed a lot over the Summer, so I hope in sharing this information I can help a few people.

Seven Rules to Not Sucking at Email

1. Use the Subject Line – Sounds simple, but it amazes me how many people send out emails with useless subjects like “hey”, or worse – no subject at all. The subject line is not only the first glimpse a person gets of your reason for contacting them (which is extremely important if you are cold-emailing someone), but it also is a key piece of information that people might search on when trying to find your email some time down the road. Take a moment to actually think about the purpose of your email. Keep it between 2 and 7 words. Make it descriptive and succinct.

2. The “Three Sentence Rule” – This is one that can be tricky to use across all emails you send, but it is definitely worth using when you are reaching out to people who (a) you don’t know personally, (b) you have never contacted before, or (c) you know suck at replying to emails. Keep your email body down to three sentences. I know that you might feel the need to put more information into an email than three sentences, but the reality is that the people on the other end of the line are giant question-marks. You don’t know how busy they are, how much they suck at email, how interested they are in what you have to say, etc. If you go above three sentences, there is a high likelihood that they will not reply to your email. It can be challenging at first, but eventually you’ll find that you can get your point across in an extremely succinct manner. Only ask them one question, and put it in your last sentence. This leaves the question lingering in the other person’s mind, and it allows them to quickly shoot you back a response without feeling the pressure of a mass-volume, heavy-content email that will require more than 1 minute of their time. Most importantly, it gets the volley of conversation started, so your more detailed questions or information can follow-on in a conversation that the other person is now invested in.

3. Spell Check – If you are not great at spelling, use the spell checker. Nothing makes you look dumber than bad spelling and bad grammar. Simple, but true.

4. Reply to Important Emails Right Away – I used to get important emails and decide that I needed to think about the response for a long time before replying. I didn’t want to send knee-jerk emails back that had incomplete information. So, I’d wait a day, maybe two days, or sometimes as long as a week. Two things happen when you do this: First, the person on the other end thinks that (a) you didn’t get the email, (b) you don’t care about the email, or (c) you are a complete idiot. Second, you could possibly forget to ever reply at all. So, when I get important emails, I reply to them right away – even if I don’t have all of the information the person needs, I’ll tell them that I don’t have it, but I’ll get it to them by X date, and then I set a reminder and make sure that I get them that information by the time I said I would.

5. Use “Unread” Status – This is a habit I’ve picked up, and I find it extremely useful. If I read an email that isn’t very important, but does require a response from me, I’ll leave it marked as “unread” until I have the time or information required to respond. Every time I open my email program, I see X unread messages, and I am reminded of the emails I need to respond to. At least once a day I know I have the time to respond to those emails (typically first thing in the morning), so I’ll go back and make sure that everyone gets the information they need.

6. Be Conscious of How Much You Suck – If you send out emails that you consider important and you don’t get a response, think about why that might be. Go back up to the points above and compare the rules to the email you sent: Did you use a descriptive subject? Was the body of your email full of too much information, or did you stick to the three sentence rule? Did you only ask one question, or did you manage to squeeze more than one question into your three sentences? Did you have spelling mistakes? Was your grammar so bad that the email didn’t even make sense? If you’ve done a good job on all of those points, then we fall into point 4: the person you are trying to contact (a) didn’t get the email, (b) doesn’t care about the email, or (c) is a complete idiot. Because so many people suck at email, I’ve often found myself falling into the (b) category. No matter which way the cookie crumbles, you need to remember the most important rule of all when sending emails…

7. Be Persistent – No matter what the reason is for someone not replying to you, persistence will get you everywhere. The best way to be persistent and not be annoying is to use rules 1, 2, and 3. Keep your emails about the business at hand, and don’t let emotion get involved – which can be difficult if you’re dealing with someone who sucks at email. The last bit of advice I can give on this point is to remember that we all live in the real world. Email is fast and easy, but the reality is that not everyone uses it, and not everyone cares about it. I know it’s scary, but if you’re dealing with someone who sucks at email, sometimes you just have to pick up the phone and call them.

We decided to pick up Git for the Vanilla & Garden projects after discussions we had with people from many other companies while we were in TechStars this past summer. Git is still a bit of an enigma to me, and I’ve been receiving pull requests from people for a while, and I’ve failed to successfully get their changes into my code – instead opting to just manually apply their changes with my own IDE. That is, of course, a total waste of my time and contrary to the entire purpose of us adopting Git. So, today I finally sat down and dug my way through to figure out how to handle a pull request.

After a few hours of frustration, it finally makes sense. Here’s the long and short of it: Define the user’s remote repo, get a local copy of their work, go into the branch you want to pull their changes into, and cherry pick their commit into your branch.

Here are the actual commands I used to accomplish this for a number of different pull requests today:

Step 1. Do you already have their repo set up as a remote branch on your dev machine? Check with:

git remote -v

If not, add the remote branch and fetch the latest changes with:

git remote add -f <username> git://github.com/<username>/Garden.git

Note: “Garden” is the name of our project on github. Obviously, you would need to substitute that for your project name.

2. Do you already have a local copy of their repo? Check with:

git branch -a

If not, create it and check it out with:

git checkout -b <username>/master

If you do already have a local copy of their repo, fetch the latest changes:

git fetch <username>

3. Get their changes into your personal working branch:

git checkout master
git cherry-pick <hash of user's specific changes that they requested you to pull>

That’s it. I can’t believe it took me so long to figure that out!

I just got back last night from a TechStars event in Seattle. The event was an opportunity for TechStars teams from all locations and years to get together and share the challenges they’re facing in every aspect of their businesses. Beyond that it was a great opportunity to meet some of the people from the Seattle entrepreneurial community and some of the fantastic mentors out there.

Listening to the other teams speak, the thing that really struck me was the different stages the companies were at based on the year they “graduated” from TechStars. Teams from the first year ranged from completely disbanded to successful exits (some of whom are onto their next big ideas). Teams from year two fascinated me most of all, as they represented the place where Vanilla can be a year from now. Some were struggling, others were seeing great success through bootstrapping alone, and others were considering new rounds of financing. Finally, the teams from this year (my “class”) were all in roughly the same boat – at or near closing their first round of financing, starting to hire staff, and really cranking hard at improving their products and services.

What struck me about the spectrum were the levels of what I’m calling “green”. I believe that we’re never going to know everything, and everyone is always in an intense state of learning – especially in start-ups, where there is always more to do than you had anticipated. I found that the knowledge I gained from interacting with the teams from the first two years was just as valuable – if not more valuable in some cases – as the knowledge I gained from interacting with mentors at the event. I left the event extremely excited about all of the things (yet unknown) that will happen to Vanilla in the next 12 months.

I spoke about these levels of green to some of the other teams from 2009 TechStars, and we all brought up one of our favourite sessions from our time at TechStars – the “Previous Founders Day”. On “Previous Founders Day”, David Cohen invited all of the companies that had previously gone through TechStars to come back to Boulder, sit in a big group across from the new class of founders, and field their questions until they ran out of them. To me, this past summer, those companies seemed so much further along than me, and I felt that we – sitting across from them – were clueless. What I didn’t know at the time was that they were sitting at various shades of green as well.

I, personally, can’t wait for that day to come in 2010. I’ve already started to compile a list of things that those founders should know about the program going in. For example: what it actually means to take on an investment and what the expectations of the investors are. In 2009 when I was going through the program, I was unaware that we’d be placed in front of investors so early in the summer, and I’m sure that to many of them I came across as a complete fool. Another example: how to make the most of your time. I thought I knew what “busy” was when I first entered the program, and by the last month of the program I ached for the heady, lazy days of month 1. Another example: how to approach mentors. In the beginning I was nervous about approaching mentors. I was afraid of saying something stupid and scaring them away. I didn’t realize that they expected me to say stupid things and have silly misconceptions. They wanted to help me work through the things I didn’t know.

Prepare yourselves, future TechStars, for the green room. I can’t wait to see what you’ve been working on, and share my “advanced” shade of green with you.

Another crazy couple of weeks. Two weeks ago I went out to NYC to meet with some investors and potential customers about Vanilla. Had an amazing time hooking up with everyone, and also managed to squeeze in some socializing with old friends from the very first forum I ever created – the one that inspired Vanilla.

Yesterday I just got back from San Francisco where we pitched Vanilla at the annual TechStars San Francisco investor day. The response to Vanilla has been fantastic, and we’ve met a ton of bright & interesting new investors as a result.

Now that I’m back I’ll finally have a little bit of time to help out people at the community forum. But there’s no rest for the wicked, and I’ve already got a long list of meetings lined up with investors.

I just got back from a week in San Francisco where I met up with a bunch of interesting people. Here are some highlights:

I met Paul Bragiel from Lefora for lunch at an awesome Indian place, and we had a great talk about the ups and downs of discussion forums, users, hosting forums, and a lot more.

I hooked up with Matt Mullenweg at his kickass WordPress/Automattic offices. I shared a bunch of our plans for Vanilla, including the brand new Vanilla 2 & WordPress Integration, and got some great feedback and insight on a myriad of subjects relating to our similar business models.

Matt Van Horn from Digg invited me up to their rooftop where we checked out the amazing view of San Francisco, had a beer, and talked about dominating the world. Matt also invited me to an event called “Digg Swigg” at a bar downtown, where I had a few too many free drinks, and met up with a ton of interesting people like Rob & Emily from Foodzie and Ryan Sarver from Twitter.

I stayed with one of my TechStars Alums, Adam Rodnitzky from ReTel Technologies, who was an amazing host and tour guide. There is nothing like being driven from one side of San Francisco to the other in a convertible Triumph with the top down.

I have a few pictures of the trip up on Flickr.

We’re heading out to Montreal today, and we’re going to be speaking at Last Drinks of Summer for the Montreal tech community. Looking forward to telling people about Vanilla & TechStars!

If you’re in Montreal, come out and say hi!

David Cohen recently announced that Eric Ries is coming to Boulder on August 19th & 20th. For those who don’t know him…

Eric Ries is a serial entrepreneur who has been talking about building Lean Startups in Silicon Valley and on his fantastic blog Startup Lessons Learned. He’s been sharing his ideas about Continuous Deployment, The Five Whys, the Ideas/Code/Data loop, Rapid Split Testing as well as Customer Development. His blog is simply fantastic and all reports are he’s even better in a person.

I’ve signed up for the workshop on the 20th, and I’m eager to learn all about his methods for building lean startups. If you’re in Boulder, you should definitely check it out.

Every time I sit down to write about TechStars, I end up getting up and walking away without putting a single word down. Not because I have nothing to say, quite the contrary, it’s because I have so much to say and I don’t know where to begin. TechStars is all about making connections with people, so I think I’ll tell my story by talking about them:

The Mentors
Do you have a mentor? I bet you do. Before TechStars I had this vision in my head of mentors being these god-like creatures that had knowledge I could never possibly obtain who would swoop in, explain something to me, and leave as quickly and mysteriously as they had arrived. The reality is that I end the Summer in Boulder not with a bunch of mentors that can help me, but with a bunch of amazingly smart friends. Jeffrey Kalmikoff is one of the coolest and cleverest people I have ever met, and I consider myself extremely lucky to call him my friend. Chris Moody is one of the kindest, most giving, and business-savvy guys I’ve ever met, and I consider myself extremely lucky to call him my friend. Micah Baldwin is a God-Damn biz-dev guru. He made me think of human interaction in ways I had never known possible. Again, I consider myself extremely lucky to call him my friend.

The list of people who have helped us throughout the summer is massive, but going in I thought they would be resources that I could leverage when I needed them. Selfish, I know, but that’s what I thought. Coming out of the program I think of them as friends that I can share my experiences with who will, in turn, share back so we can help each other. Mentorship in TechStars isn’t about them giving to us, it’s just as much about us giving back to them. Rob and Emily from Foodzie told me early on into the program to find out from my mentors what they were trying to get out of mentoring, and make sure they get it. When I tried to find out what they all wanted, the answer always came back the same: they wanted to help because it was fun and exciting. So the best thing I could do for them was to keep them as involved as possible so they know exactly what’s going on, and they can see their advice put into action. And this doesn’t end because the program is over. I’m staying in touch with all of my mentors and I hope to get them even more involved as things move forward.

The Founders
One by one the other founders are packing up and leaving Boulder to go back to their respective homes. Today I was at the office and it was silent for the first time that I can remember. The lack of energy there was palpable, and it reminded me of something Kevin Mann said on twitter a few weeks ago when he had to spend a day working at home instead of at the bunker:

Wishing I was working in the Bunker instead of the apartment, missing the energy the other @techstars bring.

At the time I thought he was being melodramatic, but now I see exactly what he was talking about. Never in my life have I been surrounded by so many smart, talented, and determined people who are pouring their souls into their ideas. I can’t imagine I will ever have the honour or privilege of living through this kind of experience with these kinds of people ever again in my life.

The Staff
Imagine having the answer to everything. Better yet, imagine being able to get an answer for everything. And not just an answer, but the correct answer. That is what David and Nicole can do. I can’t think of a single time that I had a question that they didn’t know the answer to, and most of the time, they’d tell me that answer before I finished asking the question.

David Cohen, like Brad Feld, doesn’t like to have his time wasted. I’ve never had a meeting with David that lasted longer than 30 minutes, and believe me, 30 minutes was more than enough time to get all of your questions answered and more. I tend to be a very pensive person. I like to take ideas and sit on them for hours, days, or weeks. Then when I execute, I do it extremely fast. David is the opposite of me in that way: David can see all the angles and make a decision immediately. This was overwhelming and a little scary when I first got to TechStars, and thankfully I didn’t have a serious meeting with Brad until later into the program, because Brad is like that times 10. You know when you’re talking to David or Brad that you better have seriously thought about your questions, or you’re wasting their time. Don’t waste their time.

But aside from the exacting and overwhelming intelligence of these guys, they’re also really funny, and genuinely awesome people. Oh, and David loves getting hugs. Hug him whenever you see him.

Nicole Glaros has been our rock. Always available, kind, and giving. Andrew Hyde is an unending fountain of connections, information, and kindness. Tim and Josh are two of the brightest, most upstanding young guys I’ve ever met.

Friends
So what did I really do over the last three months? 18 hour days, 7 days a week, no sleep, constantly nervous, lost 15 lbs, turned Vanilla into a business. Yes. All of that. But what do I come out of TechStars with besides a business? Friends. Friends for life.

So that’s me now: a TechStar for life.

Vanilla Interview with Mark O’Sullivan from Chris Moody on Vimeo.

I’m currently finishing up the new addons site. It’s looking nice!