My latest Boston Globe column looks back at the impact of two initiatives born in Cambridge in 2005: Web Innovators Group and Y Combinator. I also ask what we can do to improve Boston’s stickiness for consumer-oriented web and mobile startups; it’s impossible to look at the alumni of both programs and not notice that may of the most successful, like Reddit, Dropbox, Birchbox, and E la Carte, have migrated to New York or the Bay Area.

We asked David Beisel of NextView Ventures to write a piece looking back at a decade of the WebInno gatherings. A snippet:

A decade ago when WebInno started, the tech industry was still recovering from the crash that followed the dot-com bubble of the late ’90s. Startup funding was hard to find. So were experienced entrepreneurs and investors willing to act as mentors to young companies. Networking forums to exchange ideas were few and far between.
Google executive Don Dodge, who attended some of the earliest Y Combinator demo days in Cambridge, wrote a piece reflecting on what that program has become:

Y Combinator… is a startup that creates more startups. Y Combinator attracts the best entrepreneurs, who in turn attract the best investors, which leads to the highest valuations, which attract the best advisers, who bring it full circle by attracting the best entrepreneurs.
Some bonus material that didn’t make it into my column…

Reflections from Reddit co-founder Alexis Ohanian, who was part of the very first class of Y Combinator in 2005:
We got lots of great advice. Back in 2005, starting a startup wasn’t as cool as it is today (it’s the new “starting a band”) and there were far fewer resources for total novices like us. Having the YC partners for office hours, combined with our batch-mates for motivation, support, and friendship, gave [co-founder Steve Huffman] and I the environment we needed to ship code and get users (the 2 most important things for an early stage tech startup). Steve and I raised (on top of the $12K YC invested) another $70K on Demo Day. Yep, that’s it. The two of us were thrilled because it meant we could live like college students for at least another two years.
Steve Huffman participated in Y Combinator twice: once in Cambridge with Reddit, in 2005, and a second time in Mountain View with the travel-booking site Hipmunk, in 2010. I asked him to compare the two experiences:

In 2005, YC was a startup like any other, figuring out their place in the world, figuring out their strategies. But it had the same overall structure then as it does now — the weekly dinners, the shared experience. Paul [Graham] and Jessica [Livingston] cooked the dinners. It was crockpot food; we used to just call it glop. Jessica would make these big elaborate cheese spreads. It was the first time I’d had bread and cheese as a fancy snack.

The first summer, there were eight companies. It was 45 startups when Hipmunk went through. With Reddit in 2005, we were starting from scratch. Now companies will come in with real revenue, more experienced people. They’ve been around a year or two.

There was a demo day at the end of the 12 weeks. Each startup had like 20 minutes to present. The audience was maybe 20 or 30 people. Some of the audience were the other founders. The investors — if not 100 percent were from the Boston area, then it was close. Many were Paul’s friends from Viaweb [an e-commerce company Graham had co-founded, which was acquired by Yahoo.] Nobody gave a sh– about that first demo day. Now it’s a big event.

With the first batch, [the YC partners’] advice was, “Be extremely wary of VCs.” We heard horror stories about them taking control, and firing founders. Now, YC and VCs have a much better relationship. But one of their missions was to keep the power in the hands of the startups, and not investors. Investors bristle at that, but founders have so much more leverage now.

The summer [of 2005] was so busy. There was not a whole lot of hanging out. But during the winter and the following spring, Justin [Kan] and Emmett [Shear] had sold [the calendaring app] Kiko. They would come over to our apartment in Cambridge and play video games. They were the only people we knew in the city.
HubSpot co-founder Dharmesh Shah attended the very first Y Combinator demo day in 2005:

I went to what I think may have been the first Y Combinator demo day. Reddit and Kiko are the two companies I remember.

…I’ve gotten to know many of the early YC founders (Wufoo, Weebly, Xobni, Disqus, Slinkset, etc.). I’m an investor in over 10 YC companies — I’ve always had an affinity for them. I will say, I feel less of a connection to the recent cohorts, simply because the size is so large and they’re caught in such a storm of attention, it’s hard to really get to know many.

I remember being really disappointed when I heard that YC was going to shut down their Cambridge operation. It was such an energizing force for the Boston area.
I interviewed Y Combinator co-founder Paul Graham for a 2008 Globe column. In this video, you can hear that he’s starting to get frustrated with the passivity of Boston investors:

Six months later, Graham announced that Y Combinator would operate in Silicon Valley year-round; the August 2008 demo day, which I attended, was the last one held in Cambridge.

The first WebInno gathering — not yet a demo night — was held at Tavern in the Square in Central Square in 2005. Founder David Beisel has this recollection; Peter Caputa’s blog post about the event has a list of participants that is pretty amazing — they went on to become partners at Andreessen Horowitz, key Twitter execs, partners at Spark Capital, and to build companies like HubSpot and Shareaholic.

Angel investor and Akamai co-founder Jonathan Seelig attended that first WebInno, and also some of the early Y Combinator demo days:

Paul & Jessica pulling out of Cambridge was bad for Boston tech. I understand why they didn’t want to be bi-coastal — but having Y Combinator in Cambridge was great and they are missed.

David [Beisel] has done a great job with Web Innovators Group. Despite the proliferation of various incubators and demo days in Boston, it is still a very high quality platform to showcase new companies.

I think that Boston has always been supportive of young companies. We are more supportive of web and mobile startups than we were 10 years ago. But Silicon Valley’s leading players’ support of companies in this space has been on steroids compared to ours. Boston (and NY) based investors went to YC demo days (and go to today’s demo days) looking for a company that they want to fund — and treat that funding decision like any other decision in their portfolio. The “fund them all” tactic that Sequoia, SV Angel, Yuri Milner, and A16Z have taken with YC is inconsistent with the way that almost all non-Valley investors behave.

Even the most successful “newer” funds on the East Coast (think Spark or Union Square Ventures) still take every check they write as a very serious commitment to the entrepreneur. This is good and bad for entrepreneurs. It’s bad because it’s harder to get that first investment in the door — but it’s good because you know you are with a partner who treats you like a portfolio company, not like an option on a portfolio company. But it also explains why some founders are easily convinced to pick up and move west.

Personally, I have some ambivalence about this. I like being in a town where investment capital is deployed with greater prudence — but when the tech markets are on a tear, it’s hard not to wish that you were in a place where they turn the volume to 11.
Reflections of TJ Mahony, who presented his rental startup FlipKey at WebInno in 2007:

Demoing at WebInno was primarily a confidence booster for FlipKey. After the demo, we had a line of people, mostly entrepreneurs, wanting to hear more. A few VCs stopped by and asked for meetings, but it was the enthusiasm and compliments made by others that put the wind in our sails. The next morning we found several mentions of FlipKey in the blogsphere and we self determined we had “won WebInno.”
Raj Aggarwal, CEO of the mobile analytics startup Localytics, which also presented at WebInno early in its life:

WebInno was like a coming-out party for us, where we finally had an opportunity to demo our product to a wide cross-section of the Boston tech community. Our demo booth was swamped and it directly led to a few key early customers signing up. We also connected that day with someone who became one of our earliest employees, and the exposure WebInno provided supported our recruiting efforts in the longer-term too.
VentureFizz has this slideshow listing some of the more notable alumni from WebInno.