Lookback: A History of Pear Demo Day

Sometimes the best ideas aren’t planned at all. They grow organically. That was how Pear Accelerator and Demo Day began.

In 2014, Mar and Pejman invited some talented Stanford engineers to hack in the Pear offices. They also offered their mentorship with no strings attached. That community of hackers became the first ever Pear Garage cohort, which continued into the summer by popular demand from the community.

During the summer, Mar and Pejman thought it might be helpful for the founders to practice presenting their ideas formally, so they decided to host an event and invite their network. 

“It wasn’t like a ‘Demo Day’ or anything else. We just thought it would be great to invite some of our friends to come and provide feedback,” says Pejman. 

So, 40-50 great investors from the likes of Sequoia and Accel crammed into the Pear offices to listen to seven founders pitch. 

“We had handwritten name tags and it was definitely not a sophisticated production with all the bells and whistles, but the teams were great and did their thing,” recalls Lily Johnson from the Pear Ops team. 

Those teams got the attention of TechCrunch however, which ended up publishing an article deeming the event “Silicon Valley’s Favorite New Demo Day.”

That was that. Pear now had a ‘Demo Day’. From then on the team decided to put one on every year, leading to the development of a formal Accelerator program. Demo Day moved into the more spacious Cooley offices. 

Still, Demo Day kept growing. And the Pear team’s visions alongside it.  

“The next year we needed a bigger space, so we were looking at different venues and we really wanted something to still have that Pear touch—not as sterile, or conference feeling. Pejman suddenly said, ‘What about Filoli?’” Lily remembers.

It was a dreamy idea. The historic Filoli Gardens are pristine and meticulously manicured, with 700 volunteers who landscape the entire 600 acres of gorgeous property. 

“I went to many Demo Days—you go and it’s very transactional. I thought, ‘What if we change the scenery, so you can have the same conversations in a nicer environment?’” says Pejman. 

But it was also a bit unorthodox for something like a tech Demo Day. The team wondered if it would confuse investors, or if they would even be able to find the venue, since it was a little farther out from the usual Demo Day locations in Mountain View. 

Ultimately, they decided to go for it. 

“Pear is a special type of VC firm, so I think it resonated with the brand, and it just worked with us and who our team was,” says Lily. 

With that, the big event planning and production process began—always an intensive project.

“It’s like a wedding times two or three, because there are just so many logistics that go into an event of this scale,” says Lily. “It’s such a whirlwind. I remember literally running from location to location.”

Since that first Demo Day in the garden, the event has just kept on growing and growing.

“Last year, we kept sending invites out, and then we started moving past 300 RSVP’s, which is the capacity of the auditorium. I’m starting to get nervous, like ‘Alright. What if everyone shows up?’—which never happens at an event, but in the case that it did, how were we going to fit everyone into this room?” Lily recalls. “Then we got to 600 RSVP’s and it kept climbing. So we were thinking of creative solutions. We ended up reaching out to this rental company and getting chairs that were more narrow, and we were able to fit 500 chairs and it was just an absolute miracle. I remember showing up the day of  and meeting with the equipment rental manager and we were literally going with a measuring tape across the room and just squeezing the chairs together. That was a classic.”

On top of the logistics of producing the event, there’s also the important job of supporting Accelerator founders to be on top of their game for the big day, with hours spent polishing slide decks and rehearsing pitches. 

All the hard work pays off when investors and founders gather to imagine the future together for a few hours. Plus, migrating to the massive lawn terrace from the conference room is always a showstopper.

“The garden, my God, the garden—everybody loves the garden!” Pejman laughs.

Indeed, with the beautiful garden environment, live band, hors d’oeuvres, minibar, and product demo booths, Pear Demo Day has become a righteous, glittering party over the years, far more than a mere networking event. 

“We try to keep it interactive and promote relationship building in a fun Pear-ish way,” says Lily. “The style of Demo Day is a nod to how Pejman has approached everything, where he was thinking, ‘I really want the networking afterparty to feel like an opportunity for people to chat and hang out. I want people to get to know each other, but still have a good time in the process.’”

At the end of the day, in spite of all the glitter, Demo Day is really about something quite simple — getting to celebrate the hard work of Accelerator founders.

“As corny as this sounds, it is always one of my favorite moments: where you just high-five each other and you’re like, ‘Damn, we did it—YES!’” says Lily.

While we won’t be gathering in the gardens this year, that is the spirit of Pear Demo Day that will never change.