Less content, more engagement: Here’s why

Crowd clapping

When we announced this year’s event, we alluded to some of the things we have planned. It’s time to bring you along on some of the things we’re working on.

Startupfest has always had great content, and this year will be no exception. But the Pandemic hasn’t created a shortage of content. In fact, quite the opposite: It’s allowed us to share stories around the world and around the clock. It’s the engagement that’s been lacking, because there’s always an email waiting for your attention or something distracting in the next tab.

We’ve also been missing our friends. Over the last decade, thousands of speakers, panelists, investors and startups from around the world have taken our stage. Many of them returned year after year to soak up the Startupfest vibe, reconnect with one another, and share vital lessons with aspiring founders.

And we’ve forgotten how to break the ice. Without rooms to work, we don’t remember how to work the room. Without conventions in which to convene, we’ve lost the skill—and maybe the will—to network. But connecting to share ideas, meet partners, build a team, close funding, and find customers is fundamental to the success of a startup.

We’re going to help you find the things you’ve lost, and give us all a fresh start.


We’re inviting back mentors from past years and around the world, along with some fresh faces, specifically to meet with startups. We’ll make them easy to find, with unique badges. We’re equipping them to set up one-on-one meetings on site with pre-printed “dance cards” they’ll award to startups who they feel they can help with everything from funding, to legal advice, to product and tech changes.


Networking often means getting outside your comfort zone, which is much easier when everyone else is, too. The team behind Startupfest has spent the last two years designing unexpected ways to connect, online and off. We’ve helped international magazines, governments, nonprofits, and festivals stand out.

We’ll kick each day off with activities that will help you meet your fellow attendees, individually and as groups. Telling you how they’ll work would spoil the surprise, but expect to be moving around, shouting out loud, and crowdsourcing answers to real startup problems.


The difference between a run-of-the-mill conference and a landmark event is the connections we make. Sometimes, that’s a kindred spirit who helps us see a familiar challenge in a new way. Sometimes, it’s an investor who closes out a round. Sometimes it’s the perfect co-founder.

So we’ll be asking every participant a series of questions about their role, business model, funding stage, and vertical, as well as their goals at the event. Then, for attendees who opt in, we’ll use that information to recommend people you should meet during the three days of the festival.

Walking meetings

During COVID, we’ve used videoconferencing to work with our colleagues and to attend online events. That meant we had our full work environment at our fingertips, whether that was taking notes in Slack to remember a conversation; reviewing a diagram together; exchanging contact information; or sharing a link.

That was the good part.

But the sheer sameness of those events and meetings blurred them together. And with so many invites and friend requests, true interactions with people we actually knew, the value of networking diminished.

That was the bad part.

We wanted to build a better kind of in-person meeting, building on what we’d learned from our time online. And to do that, we’d need some new things.

First, we’d need a place to meet. A festival in one of the most historic ports in the world should make use of everything that’s on hand, including some incredible sights, coffee shops, waterside trails, and parks. In addition to our stages and tent village, we’re turning the Old Port itself into a networking platform.

Next, we’d need a simple, fun way for people to have productive meetings with genuine contacts.

We decided to build that part.

More specifically, some of the folks behind Startupfest, along with a team of developers, created a startup to do so. We can’t wait to show you how it works, and learn from how you use it. We’ll be reaching out to beta testers in coming weeks, too, so some of you might get invited to take a stroll with us!

Conversation starters

Deciding what to discuss can be hard. We’re building prompts to help kick things off, serving up conundrums and provocations about every facet of the startup process. We’ll serve these up in card decks and interactive signage, giving you plenty of pivots to consider and strategies to mull over with your new connections.

This year’s Startupfest is about Fresh Starts, and while we’re keeping plenty of things you love from years past, we also see ourselves as a bit of a business coach, helping you to get the engagement you crave, the friends you miss, and the ice you need to break to build, grow, and fund successful startups.