Archive for the ‘Startups’ 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.

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!

Eric Ries Coming to Boulder

Monday, August 17th, 2009


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.