Location: Green Lake
Where to find him: danshapiro.com
On paper, Dan Shapiro looks like many other guys who graduated from a high-ranking math and science university in the late ‘90s and got a job out of college at Microsoft. But five years later, his career got interesting, and he’s now raised over $30 million dollars total in venture capital to invest in startups.
“Eight years ago, I knew nothing about starting companies, I had zero experience writing a pitch deck and I knew exactly one angel investor and zero venture capitalists,” says Shapiro.
After five years of working at Microsoft, which he looks back fondly upon, Shapiro started to realize that there were two kinds of people out there in the professional world: “Those who are experts in something and who refine their skills to an art, and those with short attention spans who compulsively throw themselves into situations for which they’re under-qualified and ill-prepared,” says Shapiro. “I fall in to the second camp, for better or for worse.”
Through the help of a supportive community and what Shapiro describes as “many, many coffee meetings,” he started to navigate the startup world. “I can’t easily repay the time that was invested in me, but I can pay it forward,” he says.
But there are only so many hours in the day to do one-on-one mentoring at coffee shops, so Shapiro has found writing to be a great way to funnel his wisdom and share it with the startup community.
Other than perhaps the early years of danshapiro.com, which were primarily devoted to blogging about woodworking, Shapiro’s blog — “quite possibly the only entrepreneur blog” — is devoted to touching on many issues pertinent to startups. “I’m a miserably slow author, but bit by bit, the material comes out,” says Shapiro. “And while I’d rather spend the time with individual companies than cranking out a few pages of material, I know that I can help more people by writing than by scheduling a day full of coffee meetings.”
As to how he has managed to raise such an incredible chunk of venture capital money over the last eight years?
“I wish I knew what works because I’d do more of it. I suspect, though, it has a lot to do with forcing myself into extroversion,” says Shapiro.
Like most of us, he hates the forced interaction that comes with meeting new people. “But I’ll be damned if it doesn’t seem to work,” says Shapiro. “Seattle’s full of amazing people who are not afraid to roll up their sleeves and make things happen when the circumstances are right.”
In fact, the sale of his last company, Sparkbuy, to Google came about from a conversation with his seatmate on an Alaska Air flight from San Jose to Seattle.
Currently, Shapiro’s most exciting project is the O’Reilly book he’s writing about startup CEOs.
“I’m incredibly excited about telling some of the amazing stories and sharing some of the knowledge I’ve learned over the years with a wider audience,” says Shapiro. “It’s slow going, but enormously gratifying.”
Beyond the countless hours mentoring, advising and writing, Shapiro loves being a dad and is more proud of his family than anything else. His four-year-old twins “are the very best kind of startups,” says Shapiro. “Watching them build Legos, tell each other stories, and sing songs to us is more rewarding than anything I could ever do at the office.”
Having spent most of his life in the Pacific Northwest between Portland and Seattle, Shapiro is glad to be raising his kids here with his wife, Leslie. “They love the preschool curriculum at JDS, which seems to get better every year, and we love the fantastic community of parents, as well as look forward every weekend to services at Seattle’s best-kept synagogue secret: Emanuel Congregation,” says Shapiro. “We feel incredibly blessed for the community we’ve found here in Seattle!”