Archive for the ‘TechStars’ Category


Thursday, May 19th, 2011

No Doubts

Fred Wilson states that (a wise VC he knew stated):

A CEO does only three things. Sets the overall vision and strategy of the company and communicates it to all stakeholders. Recruits, hires, and retains the very best talent for the company. Makes sure there is always enough cash in the bank.

Fred goes on to say:

I’ve learned that great CEOs can and often will do a lot more than these three things. And that is OK. […] But I have also learned that if you cannot do these three things well, you will not be a great CEO.

I wish Fred had posted that on the web a year before he did, and I wish I was wise enough to understand what it meant at that time.

When we took Vanilla through the TechStars program in Boulder in 2009, we really went there for the mentorship & networking. The program most definitely delivered on that account, and we came through a gruelling 3 months with our minds in heavy “listen to your mentors” mode. After leaving the program, we were able to raise a round of financing, and Vanilla’s Board of Directors was born.

We have an awesome board of directors at Vanilla with, we believe, some incredibly smart people who bring unequaled insight to the table. This fact, combined with the fact that we had just come out of a program where we had been heavily (and happily) mentored led to one powerful problem: I was not a good CEO.

The part of Fred’s quote above that got me was that a CEO “Sets the overall vision and strategy of the company and communicates it to all stakeholders.”. I failed at this job. Miserably. Instead of coming into board meetings with strong opinions about what we are doing and where we should take the company, I was deep on the other side of the fence: asking (practically begging) for advice, always willing to accept criticism on decisions to the point where I never sounded confident in any of them. I treated our board of directors like mentors instead of equals.

The hard lesson that I’ve learned over the last year is that when you put yourself in a diminutive position, people will treat you accordingly. In other words, if you act like you might be wrong, people will assume you are wrong. And if you act that way all the time, they will think that you just don’t have any idea what you are talking about.

It’s a hard fact to remember, but for all their experience, investors put their faith (and money) into your company (ie. you) because you are the experts in your field. You should always have the strongest opinions about the direction of your company from day-to-day tasks to overall vision & strategy.

I’ve spoken with many CEO’s about the struggles of being one, and there are many pitfalls that my friends and colleagues have experienced – this one being no exception. I hope that someone (perhaps the latest companies leaving the warm embrace of TechStars) reads this and takes it to heart.

Don’t Suck at Email

Wednesday, December 9th, 2009


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.

The Green Room

Friday, November 6th, 2009

TechStars in Seattle

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.

Vanilla in Montreal

Wednesday, September 2nd, 2009


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!

TechStar for Life.

Saturday, August 8th, 2009

TechStars for Life

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.

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.

A Brief Retrospective

Saturday, August 8th, 2009

I plan on writing an epic post about my experience at TechStars after I recover from the wicked hangover I’m experiencing from last night’s founders party at our crappy apartment. In the meantime, I thought I’d post this video interview I did with one of my favourite people in Boulder, Chris Moody. It’s 22 minutes long, and I think watching it you can get a sense of how exhausted I am after the end of TechStars. I can quote Todd saying that TechStars has been “the best experience of my life”, and hopefully that comes across in the interview as well. Here’s Chris’ post about it, and here is the interview:

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


Tuesday, July 14th, 2009

I had a brutal summer cold last week that left me bedridden for a few days. I’m finally over it and working away furiously at our task-list.

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


Tuesday, June 16th, 2009

A few months ago I posted about how I went down to Boulder, Colorado to attend TechStars for a Day. TechStars is a mentorship-driven seed-stage investment fund. In human terms, it means that they invest a small amount of money in your business and provide mentorship to help you get off the ground in exchange for a small stake in the company.

I stumbled upon TechStars when I decided that it was time to take Vanilla to the next level. Garden and Vanilla 2 were nearing completion, and I realized that without some kind of small investment, I was going to fall back into the pattern of trying to support my open-source efforts by doing side-projects. And inevitably those side-projects become my main project, and Vanilla becomes the side-project in turn. I started emailing and calling everyone I knew asking if they had any ideas for how I might make a real business out of Vanilla. One of my good friends referred me to Jeffrey Kalmikoff at Threadless, and Jeffrey referred me to David Cohen from TechStars.

I honestly didn’t think TechStars was a viable option for me. In my mind I just needed some money so I could continue to develop and pay my monthly bills. Furthermore, I didn’t think that I’d get in if I did apply. After speaking with David, I realized that the money wasn’t the important piece at all – the mentorship was. I decided to attend TechStars for a Day so I could get a better glimpse of what it might be like. Eventually I understood it to be an instant network of people who are all interested in helping me succeed. Living remotely in Saskatchewan, I had nothing of the sort. I could have moved to Toronto or Vancouver and attempted to build a network like this on my own, but getting access to the types of people that TechStars boasted would have taken years.

The most important thing for me was to have the ability to work at Vanilla full-time. I realize that there are so many things about it that could be so much better, and those things would be better if I could just devote 100% of my “office hours” to the job. So, I applied. A few weeks later I discovered that I had been accepted. At that point I scrambled to get as many contract-work hours as I could, scrounged every penny I could, and development on Vanilla ground to a halt.

I’ve been in Boulder now for just over a month, and I still haven’t really had any time to do any development on Garden & Vanilla. The first month was totally devoted to meeting this network of people. I’ve met people from Mozilla, Facebook, Digg, Microsoft, Yahoo, Google, AOL, and many many more. All of them have been excited about Vanilla and very supportive of my efforts. They’ve shared advice, support, contacts, and so much more than I really could have imagined.

So, why am I telling you this now?

There are over 300,000 installations of Vanilla out there that I know about. Over 1,000 plugins are downloaded from our addons site every day. Vanilla has been adopted by Mozilla, O’Reilly Media, and many other companies. There are over 10,000 members in the Lussumo Community. I’ve left my wife and family behind in Canada to spend the summer down in Boulder living on beans.

I wanted everyone who uses Vanilla to understand just how committed I am to making Vanilla better.

My Trip to Boulder

Tuesday, March 3rd, 2009


Today I spent the day at TechStars for “TechStars for a Day”. It was a very overwhelming day and I met a lot of interesting people. I came out of the day with a number of realizations about things that I’ve been doing “wrong”, and improvements that I need to make in my approach.

1. Private Beta == Bad
This notion that I’ve had of letting just the core community members in to test a closed beta of Garden & Vanilla 2 is simply a bad idea. After all, why limit the user-base when I know that *all* of you have fantastic ideas? So, the first beta that goes online will be open to anyone to register and use. I want everyone to get a taste ASAP.

2. Delivering on Promises
I’ve been explaining the softare for literally months without giving any of you any real immediate interaction. I need to pick up the pace and get something out there for you guys to play with SOON. I don’t have a specific date for you, but my hope is that we’re talking about weeks, not months.

3. Listening to You
Obviously I have my ideas of what I would like to see the software do. But ultimately it will be you, the users, who judge the software as something you will want to use – or not. So, after you’ve had a chance to use it, I will be paying a lot of attention to your feedback. What do you like? What don’t you like? What is missing? What have I overlooked? etc.

4. Open the Source
I still believe that it is important to have a real focus on where the software is going. But I think I’ve been confusing that need with “letting go of control”. The way that changes were implemented with Vanilla 1 were far too constricted. I’ve been speaking in private chat with a bunch of the Vanilla 1 developers about this, and while I won’t be allowing *everyone* to commit changes to the core, I will be accepting bugfixes and change suggestions from the community and allowing other Vanilla 1 developers to review and decide on which ones should be a part of the core. Some Vanilla 1 developers are already looking into ways we can facilitate this process, and I’ll be relinquishing a lot of control to them right away.

With all of these things in mind, my primary goal for the software in the immediate future is to get a beta online right away. I’m trusting that everyone is aware that the design isn’t going to be as polished as the final product will be. My focus will be on completing core features and not focusing so much on design. Design can be polished later.

The bottom line comes down to a quote I heard today: Getting all of your ducks in a row is important, but it is more important that you do something with the ducks. That is now the focus.