“I was always a computer nerd—I got a computer for my bar mitzvah,” Brad Feld says. “I was a pretty serious tennis player for a couple of years until I turned 15, then I discovered girls and computers at about the same time and that was the end of my tennis career.”

He wrote tons of programs as a teenager, but the most memorable was a Yahtzee game that was shipped out on a supplemental program disc with an early Texas Instruments PC. “I don’t remember if it was my friend’s dad who gave it to someone in his office, and there was a couple days where we were like, ‘Hey, we should get something for this!’” he recalls. “But we were like, whatever, we were in 10^th grade, this is just cool. They probably sold a grand total of nine TI PCs, but I remember that because it was the first time I felt like I wrote something that shipped to a bunch of people.”

He also got a taste for entrepreneurship early. In the summer before college, he was the first employee at a company that wrote software for oil and gas industries. He didn’t have equity in the company but got royalties from the software that he wrote while he was there, so would get monthly checks for thousands of dollars while he was in college.

“Very early on, I got this sense of controlling my own destiny from an economic perspective, and I loved working for this very young company,” he says. “I remember lots of afternoons hanging out in [founder] Chris’s office, and at 4 p.m. we’d each be drinking a beer, and I was 18 years old and having fun with the creative experience of creating a company from scratch.”

He got into MIT early, never applying anywhere else. “I picked MIT because my very first real girlfriend—to the extent that you can have those in eighth grade—totally loved engineering and science and wanted to go to MIT, so it stuck in the back of my head that MIT was an interesting place,” he recalls. “It’s a brutal place to go to school, and for many people it’s a daily assault on your self-esteem.”

He’d intended on majoring in computer science, but ended up getting a business undergraduate degree with a focus on computer science from the MIT Sloan School of Management. He continued on to get a master’s from Sloan and even spent some time in the Ph.D. program. But though he was at school from 1983-1990, he’d checked out by his junior year, when he started a company called Feld Technologies. “We wrote business software in the 1980s for medium-sized companies back when even just having a PC was a new idea, let alone having networked PCs in an office,” he says.

He and his partner raised no funding and built a profitable 20-person company with a few million dollars in revenue, before selling it about nine years later to AmeriData in 1993. “Up to that point, I’d never done investments, I’d never done deals, I was running a small company in Boston,” he says. 

When he became CTO at AmeriData after the acquisition, he started making his own angel investments. “They were small, typically, in a bunch of startups, including a number that ended up being very, very successful—a couple of early Internet software companies that had IPOs,” he says.

Along the way he connected with some guys from Softbank Technology Ventures, and they founded Mobius Venture Capital in 1997. They raised a series of funds in 1997, 1999, and 2000, but after a difficult few years from 2001-2003, they decided not to raise another fund as a team. He started Foundry Group in 2007 with three people he’d worked with at Mobius, investing in new companies as well as managing the active companies from the Mobius portfolio.

He started blogging in 2004 because he was interested in a protocol called RSS. “I didn’t totally get it the first time I saw it, but I got the connection to blogging,” he says. “I thought if I really wanted to understand this technology, I should just use it, so let me learn how blogging works. I didn’t have any expectation that anybody would read this stuff, except maybe my mother.”

Now, he blogs to be accessible to entrepreneurs, and to help them in a scalable and impactful way (that’s also why he’s involved with TechStars, a program that provides seed funding and mentorship from investors.) He blogs not just about venture capital, but about his life, his running, and his relationship with his wife Amy. “I talk about things that inspire me, things that are important to me, things I think about,” he says.