Why I Left IBM

I was recently having a conversation with an aspiring entrepreneur and the topic of why I left IBM came up. It’s been just over a year since I left the consulting world and joined Three Screen Games full-time to lead the product team – I left May 1, 2009 – so I have a bit of perspective on the decision now.

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Why did I leave IBM?

First, let me say why I didn’t leave: I didn’t leave because I hated the company, the work, or the people. Almost without exception, I loved the people that I worked with. If you want to get to know your co-workers really well, go into a high-travel consulting job where you spend each and every week with your co-workers in a strange city. Where you eat more meals with them than you eat with your family. Where you sleep in a hotel room down the hall from them. You get to know them better than pretty much anyone else. I really enjoyed the people that I was working alongside – hugely talented, driven to do the right thing. I have a great respect for IBM in its ability to amass a formidable talent pool. As for the work and the lifestyle, I loved the consulting life – seeing different companies, each with its own culture and unique challenges.

So, why did I leave? In short, I’ve known for a long time that I wanted to be involved with a startup. After doing independent consulting during high school and college, I knew that I had the entrepreneurial bug. I initially went to IBM to see how the “big guys” solved all of the consulting issues that I ran into when I was working with clients independently. Finding that many of the issues were the same, just multiplied by millions of dollars, gave me a lot of confidence in my abilities.

While the people were great and I enjoyed the lifestyle, I was frightened of becoming complacent. I was afraid of getting to the point where I became used to the salary and the lifestyle. Flying around in first class, working on high profile projects, earning a nice salary, stock options, etc. – it’s all really easy to get used to. I knew that once I became used to it all, I would reach the point where I wasn’t able to take the 100% paycut to join an early stage startup. And so, I was afraid of somehow missing the ability to pursue one of my goals – helping to create a company from the ground up.

James Kwak does a really great job of describing what I was afraid of in his recent post Why Do Harvard Kids Head to Wall Street?: “…[O]nce you’re in the door, the seduction begins….Your expenses grow to match your income. As the decades pass and you realize that no, you’re not going to save the world, the money becomes a more and more important part of the justification. And when you have kids, you’re stuck; it’s much easier to deprive yourself of money (and what it buys) than to deprive your children of money.”

I think often we know what we should do, but it’s hard to actually go and do it. It certainly doesn’t get any easier with time, and in many cases, things just get harder. It wasn’t exactly an easy decision to make, to decide to leave my position last spring, with the economy still uncertain, and still getting a lot of experience and having a lot of mileage left in my career at IBM. But I knew that it was one of the few opportunities I’d ever have to take the leap, and I’m very happy that I did.

Part of this is the self-awareness that I believe is needed to be effective as an entrepreneur and wrote about earlier. In this context, do you know what you need to feel confident enough to make that kind of a jump? Is it a strong team, some validation of your concept, an early customer? Figuring that out will help you recognize when you’ve made enough progress to make the move. For me, some of that was having a business partner and a team that I was confident could hold up their end of the bargain, and having a top notch group of advisers through DreamIt Ventures. (Having people in my life that supported the decision and encouraged me was a big part of it, as well.)

Who knows where things will take me next, but I consider myself fortunate to have had the courage to take advantage of an opportunity and accomplish one of my goals for myself.

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Back to the anecdote that inspired this post – the aspiring entrepreneur that I was talking with was unhappy with the ‘big company’ internship that he had for the summer. It wasn’t going to give him the experience that he was hoping for and would be essentially worthless busy work day after day. He had pretty much already made up his mind before talking to me, but perhaps some of these thoughts helped him feel less crazy for walking away from a “perfectly good job”. In my mind, as I discussed with him, if you’re not getting the experience you want, especially when you’re young, there are few reasons why you should stick it out and so many reasons why you should take the leap to follow your dreams. After all, you may not get another chance.

I have a quote from Steve Jobs on my personal home page that I think speaks really well to this point:

“We don’t get a chance to do that many things, and every one should be really excellent. Because this is our life. Life is brief, and then you die, you know? So this is what we’ve chosen to do with our life. We could be sitting in a monastery somewhere in Japan. We could be out sailing. Some of the [executive team] could be playing golf. They could be running other companies. And we’ve all chosen to do this with our lives. So it better be damn good. It better be worth it. And we think it is.”

This is your life. Make sure you’re getting what you want out of it.

White Bear Yard – home for startups in London

Last month, while in London, we met up with an American friend who’s building a startup in the UK. His company and five others are working out of a new space in Clerkenwell called White Bear Yard. If you’re looking for an example of a great space for startups to work in, this should be one of your models. The space is fantastic and the companies are equally exciting – I’m sure we’ll see great things from this cohort.

The space was originally part of IDEO’s London studio, but is now the home to a bunch of motivated entrepreneurs (IDEO is still on one floor of the building). Below are two photos I took with my Blackberry, though they don’t really capture the essence of the space. It’s a very contemporary space, very airy and open, with nice areas for the companies to collaborate. And, for those times when you need to unwind, the space comes complete with a rooftop garden (also very nice!)!

If you’re in the area, I highly recommend you check it out. Follow White Bear Yard on Twitter and read more in this post on VentureBeat.

Located up a fairly nondescript alley in Clerkewell:

A vibrant home for startups – after hours…:

EDIT: Added link to White Bear Yard: http://www.whitebearyard.com/

Quick fix for MacPorts Ruby version conflicts

After configuring MacPorts, I was running into an issue on my Mac with Ruby on Rails where ‘/usr/bin/env ruby’ was giving me a different version of ruby than the one which has my gems installed. This was an issue for trying to run the ruby scripts with the shebang according to the best practices (i.e. /usr/bin/env ruby). So, trying to run script/console or script/server gave me lots of headaches. This may be a simple fix, but hopefully this will help others with similar issues.

$ /usr/bin/env ruby -v
ruby 1.8.7 (2009-06-12 patchlevel 174) [i686-darwin10]
$ /usr/bin/ruby -v
ruby 1.8.7 (2009-06-08 patchlevel 173) [universal-darwin10.0]

It took me a bit of fiddling and testing to figure it out, but I finally realized out that the MacPorts installation process had put its bin directories before the default bin directories. Ordering is fairly crucial – paths that are listed first take preference.

This is what I had after installing MacPorts:


export PATH=/opt/local/bin:/opt/local/sbin:$HOME/bin:$PATH:/usr/local/bin


This is the correct order (note – moved the /opt/local paths for MacPorts at the end to get things loaded in the right order):


export PATH=$HOME/bin:$PATH:/usr/local/bin:/opt/local/bin:/opt/local/sbin


With the order changed, now Ruby and Gem load from the same install (the MacPorts version of Ruby was loading overtop of the base Mac install).

Again, a simple fix, but hopefully, it might help someone running into the same issue.

A Different Way to Look At Group Projects – Who Makes You Successful?

A fruitful behavioral interview question is to ask about a time when the interviewee was working in a group and they had to deal with someone who wasn’t cutting it. I say it’s fruitful because it usually is always asked and therefore, since candidates know it’s coming, they have a thought out answer for it. The question usually attempts to get at how the person dealt with the issue – did they work with the student to resolve it, did they work with the professor, etc.

It can certainly be interesting to know how people handle themselves in difficult situations. However, I think for entrepreneurs, there is a different, more telling way to look at this theme. You want to get at what did the person learn about who makes them successful.

As I’m finding out, entrepreneurship is everything you expect from hearing about it – it’s fun and rewarding, it’s also confusing and downright tough sometimes. And it’s a constant roller coaster from good days to not so good. There’s some debate about whether you need a co-founder in this modern age of startups, but the plain truth is that it’s hard to succeed, in general, with startups and being alone doesn’t add much to your chances. I’m with Paul Graham on this one (see #6). The point of the Business Insider article is that you have slim odds of finding a co-founder that you align well with.

So, steering back on topic – figuring out who makes you successful.

In most groups in school, students are lumped together in groups, usually at random. But when it’s over, did they figure out who they worked well with any why? Did they distill that thought nugget down, so that the next time they get to pick who they’re going to work with, they know what traits they should be looking for?

Each person usually has specific types of people that they work well with. Maybe a visionary works well with an organizer. Or an organizer works well with a someone who’s very driven and motivates the team. Regardless of the specifics, I think its highly important for people to figure out who those types of people are for themselves and to do so as early as possible. Then, as you meet folks and make connections, you can seek to build relationships with those that align with the type you’d work well with.

This is a critical concept for entrepreneurs. The team is everything – it’s one of the three critical legs of the stool. If you know more concretely who you would work well with, that should go a long way towards helping you to figure out who you want to co-found a startup with.

As I started to discuss in my post on the first two steps to encouraging entrepreneurship, I think a big part of learning to be an entrepreneur is learning to be cognizant of things that most people notice, but don’t take note of or take action on. In much the same way as you need to train yourself to recognize the market “pains” that product opportunities create, you need to train yourself to note who you work best with, what personalities are most compatible. It’s almost like an entrepreneurial variation of Situational Awareness, perhaps a combination of the three levels. Regardless, being able to make those observations and and pushing to distill them down into something more actionable is key and if you can figure that out, you just increased your startup’s odds.

So, focus on who makes you successful.

Videos from DreamIt’s 2010 Kickoff, including Steve Barsh, the 2009 Alumni Panel, Lucinda Holt, and Startl

Videos of DreamIt Ventures Kickoff Weekend’s events are now on Vimeo – embedded below. This includes a video of Steve Barsh’s awesome keynote (which I discussed previously), a talk by Lucinda Holt – startup CEO extraordinaire, the 2009 alumni panel (also covered previously – featuring SeatGeek, Notehall, and my comments from FanGamb), and a presentation by the founder of Starl, which is partnering with DreamIt this year. It’s great to see these insights for entrepreneurs being made accessible to all from one of the top accelerators!

Steve Barsh

DreamIt 2010 Kickoff – Steve Barsh Keynote from WizeHive on Vimeo.

Lucinda Holt

DreamIt 2010 Kickoff – Lucinda Holt from WizeHive on Vimeo.

2009 Alumni Panel

DreamIt 2010 Kickoff – Alumni Panel from WizeHive on Vimeo.

Phoenix Wang on Startl

DreamIt 2010 Kickoff – Phoenix Wang on Startl from WizeHive on Vimeo.

IBM doing seed-stage acceleration the right way: IBM SmartCamp

Back in April, I posted about the IBM SmartCamp initiative taking place this year. I recently connected with Eric Apse, the IBM Venture Capital Group partner for the Boston area, who is leading the program in that city, to learn more about the initiative. IBM SmartCamp will run on June 3rd in Boston. Dates for other cities are on the program’s blog.

In short, it’s one of the most innovative efforts that I’ve heard of to align startups with a larger enterprise. IBM has really thought this one through. While there’s certainly a lot of potential upside to IBM if it helps accelerate high potential startups through this program, the success of the program is also being measured from the participating startups’ perspectives, so IBM has their priorities in order.
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Eric provided some details on how the program will work. SmartCamp is being run in select cities with strong entrepreneurial communities. In each city, there is a one-day program, bringing the selected startups together with a number of mentors and advisors. The program is structured interaction with the 25 mentors – 45 minute rotations with 5 mentors per rotation. Then at 3pm, the companies will present in a competition format. (The company that wins from each city will be invited to Dublin, Ireland, for a global competition in November – the winner there is deemed the world’s ‘smartest startup’.) Then following each of the city program days, the companies get 12 weeks of mentoring through IBM – TechStars will be helping to offer mentoring in Boston, Seedcamp in Europe.

During the mentoring, IBM places the startups in contact with internal connections that are aligned with the companies. The goal of these interactions is focused on helping the startups figure out the right go-to-market strategy. Internally, IBM is also putting together a cross-discipline board of Smarter Planet stakeholders to review the ventures and make decisions on which startups align with IBM’s initiatives and thus further partnerships should be made.

I asked Eric about how SmartCamp is being measured by IBM. After all, most business initiatives are measured by specific metrics and I was curious what IBM would be using to determine whether SmartCamp had been an effective investment. Eric explained that there were no specific metrics for SmartCamp’s success. Instead, IBM is more focused on what kinds of success IBM can drive from the program, whether that success is funding for a participating company, a partnership with IBM, or another kind of success for a participating venture. Certainly IBM is keeping a close eye on the ventures to figure out which would be best for IBM to partner with or acquire, but they’re taking a very long-term view on the success of the initiative, more around on how IBM can access these markets through startup partners over the long term.

Eric said that this is very similar to how IBM’s Venture Capital initiative has been running for over 10 years, taking a milestone-based approach towards measuring its success.

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On the whole, I was extremely impressed by what I learned about IBM’s SmartCamp initiative. The relationships with the mentoring programs (i.e. TechStars, Seedcamp), give the participating ventures important opportunities to get advice and feedback, in addition to powerful networks. And the internal connections to Smarter Planet stakeholders will be important for the participating companies, as well. But, I think the most telling aspect of the program is how it is being measured by IBM.

Instead of the typical corporate world, quarterly management dashboard, IBM is taking the right view on the program. Seed-stage acceleration isn’t something that works on Wall Street’s calendar – it takes time, and there are many twists and turns in the road, as I’ve learned first-hand. But, over the long term, you can build a program that helps convert ideas into sustainable ventures and transformative products with the right mentors, connections, and process. It appears that IBM has put a lot of thought into what kind of process would be most effective – not only for Big Blue, but also for the participating companies. And I think a lot of entrepreneurs are going to find that hugely valuable for their ventures.