Leaving Microsoft: From Redmond to Sand Hill Road

After nearly three years at Microsoft, based in San Francisco and focused on our BizSpark startup business, I’ve decided that it’s time to move on and begin the next chapter. I will be joining early stage venture capital firm Shasta Ventures on July 11, 2011.

The past three years at Microsoft have been an incredible experience. I’ve worked with some of the smartest people I’ve ever met, had the opportunity to shape and launch global programs, and be inside of one of the world’s largest corporations as it strategizes, builds, and launches products which affect hundreds of millions of users. What continues to boggle my mind is the sheer scale at which this company operates. We’re not just an operating system software manufacturer, or just a database software company, or just a cloud services provider, or just an email service provider, or just an advertising company, or just a search engine, or just a gaming console manufacturer with one of the largest online communities of gamers, who recently set the record for the fastest-selling consumer electronic device in history. We don’t just help enable students to succeed, or workers to be productive, or banks to be secure, or intelligence agencies to be operational, and cities to be efficient. We do all of it. And it all needs to work, flawlessly. That is a big job.

I’ve had the great opportunity to work with some of our highest potential BizSpark startups, providing support and a tangible roadmap to success by helping connect the dots for them both inside, and outside, of Microsoft. It’s been an absolute pleasure working with the entrepreneurs behind companies like Huddle, LiquidSpace, Rally (née Piryx), Nutshell Mail, Apprenda, Lymbix, Spoke, SocialShield, and partner organizations like StartupWeekend, The Kauffman Foundation, Founder Institute, Orrick, and many many more.

It hasn’t always been a walk in the park. Having evangelized and marketed Microsoft products in Silicon Valley, and other startup hotbeds, I’ve received more than my fair share of snide remarks, insolent quips, and laughing fits in my face. However, over the past three years we’ve seen some incredible traction and positive change in how startups perceive Microsoft in general. We began at ground zero with not much more than spoken word and a banner, and through the tenacious leadership of Dan’l Lewin, we designed and executed a program specifically for startups. The first of its kind at Microsoft, BizSpark provides software, support, visibility and business development opportunities for startups around the world. We now have over 40,000 actively engaged startups in over 100 countries.

I’m not one to shy away from big obstacles, most of my life I’ve been creating new things, and I work best where I have a set of objectives and an undefined path to get there. I thrive at the opportunity to jump in head first, work tirelessly, and can make a tangible impact on the direction and growth of a business.

This is why I’m thrilled to be joining Shasta Ventures. The founding team, Tod Francis, Rob Coneybeer, Ravi Mohan and Jason Pressman have done a phenomenal job building their 6-year old “upstart” firm into an active, well-regarded Sand Hill Road VC firm with an outstanding portfolio including: Mint, LiquidSpace, TaskRabbit, Gowalla, Smule, Zuora, Spiceworks, and more. The team, which also includes Austin GroseSean Flynn and Joe Ryan, has brought together their decades of consumer, technology, and investing experience to assemble a firm with an absolute focus on the entrepreneur making a point of always being personally available and quick to provide assistance wherever needed. I have been struck by how genuine and truly approachable each member of the team is. Their honesty, transparency, and lack of ego are extremely important traits of a team that I’m soon to consider myself a part of.

In my role at Shasta Ventures, I will be tasked with meeting the best entrepreneurs with the biggest ideas, helping evaluate startup ideas as candidates for investment, and keeping a finger on the pulse of the industry to identify shifts and new trends as quickly as possible. To me, it’s a dream job, and I can’t think of a better firm or group of people to be joining.

I want to thank the many, many people at Microsoft who have contributed to my experience and believed in me enough to entrust me with some big-ass responsibilities, including Dan’l Lewin, Cindy Bates, Mark Hindsbo, Cliff Reeves, Matt Thompson, Joshua Waldo, and Michael Francisco. I look forward to keeping a close relationship with Microsoft, and all of my friends, in my new role at Shasta Ventures.

Beginning July 11, I’ll be on the lookout for the most innovative companies, strongest teams, and biggest ideas around. If you think there’s something I should see, let’s connect! Email me at jacob at shastaventures dot com; I’m @jacob on twitter, so reach out, let’s catch up, and let’s talk about the future.