Every great conversation starts with a question

Published On Jun 7, 2022

Startupfest this year is all about engineering serendipity. We’ve already explained how we’re using an unwebinar philosophy and the six archetypes of the startup world to build unexpected experiences throughout the event. Last week, we walked you through our Five Fresh Faces matchmaking algorithm, and today, we want to share a bit about how we’re helping great conversations to happen onsite.

We’ve scoured the web, and surveyed founders and investors on Twitter, for some of the most thought-provoking and controversial questions startup founders have to tackle.

Some of those questions are specific to a particular role:

  • Investors debate among themselves how to set the best valuation, or how to make a profit while still motivating founders.
  • When analysts meet, they agonize over being data-driven while leaving room for inspiration, or how to get executives to care about metrics.
  • Left alone, hackers argue over striking a balance between technical debt and over-engineering their prototypes, or which tech stacks make an acquisition easiest.

Other questions are specific to the challenges startups face: Legal and structural decisions, financial questions, finding the perfect pitch, or building a superb team.

Throughout the 2022 Startupfest venue, we’re going to be prompting attendees with these questions using something we call Conversation Codes.

Birds Of A Feather Conversation Cubes will prompt you with questions specific to your role. If you’re a designer, find another designer, scan a cube, and spend 30 seconds answering the question you get on your device. Each of the six sides of these cubes will have questions tailored for a specific role, as a way to get to know your peers and hear other opinions on some of the most vital topics in the startup world.

Startup Challenge Conversation Codes will line the walls of the Old Port venue. Scan the code from up close or across the room, and dive into hot topics like pitching, building a team, legal structure, and funding.

Conversation Codes are another facet of the experience we’re building this summer as we get attendees out of their comfort zones, helping them to foster valuable connections and explore new ideas. It’s all part of our Fresh Starts theme, and we can’t wait to see what you do with it.


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