5 Key Learnings to Host a Successful Founder Day

Katie Andresen
Better Ventures
Published in
4 min readOct 17, 2023

In September, the Better Ventures team hosted our founders at our Oakland office for our first in-person Founder Day since the pandemic.

Fostering a sense of community and connections amongst our founders is a big focus at our firm. We love seeing the light bulbs go off as founders talk about shared problems they’re tackling and make connections across other founders, investors, and our wider community. We also know that time is a very valuable resource for founders and, as a result, we need to make the day as valuable as possible.

Read on for some learnings about how to host a successful Founder Day.

Founder Day success!

Founders love to connect with one another — and need it!

Being a founder can be a lonely and demanding journey. They have a million things on their plates, daunting questions to find solutions to, and often few with whom they can share their concerns. Being surrounded by those who can empathize with the founder journey is a liberating and refreshing experience. They’re able to tap into a vulnerability that unlocks brainstorming and solutionizing. Plus, as humans, we all crave a sense of belonging and connection. The number one piece of feedback we received following the event was how valuable founders found the connections they were able to make at Founder Day.

Founders benefit from both mentor and peer conversations

To maximize learnings for founders, we’ve found mixing both peer and mentor conversations works best. There’s something about speaking to someone who’s in the trenches going through the same problem as you to unlock insights. At the same time, we constantly hear from founders that they want to talk to a founder one to two stages ahead to get insights into what worked and, importantly, what didn’t when they approached a similar issue. These key learnings can save time from those who have been there and done that.

Early stage founders in a small breakout discussion taking in lessons from an exited founder

Balance structured programming and unstructured time

We intentionally planned both structured and unstructured time for Founder Day. We want them to come away with learnings on topics they’ve expressed a desire to learn about. Plus, we’re able to see similarities in types of requests and asks from founders across the portfolio. By structuring segments of programming, we can jumpstart value.

However, there are always hidden similarities and points of brilliance that come out organically. Don’t overprogram the day — people will be exhausted and those pauses can hold moments of true spark. I’ll never forget the organic conversation between two PhD material scientists CTOs that we hadn’t anticipated because their companies were in vastly different fields. Magic is hiding in spontaneity.

Founders share one thing they love to do that they’re bad at and one thing that they’re awful at that they love to do.

Mix in opportunities to connect with other people from your broader community, including GPs & LPs

We ended our event with a community happy hour that brought together founders, LPs, GPs, and others in the BV community. Network is so important in the tech and venture ecosystem, so creating a space for these connections to happen is important. It gives a more organic path for founders looking for investor, customer, and expert connections to occur as opposed to cold emails (which still work by the way, but take some time). Plus, it’s also nice to end the day on a social and celebratory note.

Gather feedback from attendees

I have worked on many teams — both VCs and startups — who agree that feedback is a gift. Don’t forget to send a follow up to attendees asking for feedback. That could be in a survey, long form writing, or some other method. It helps you stay close to the needs of those you’re creating programming for and learn insights in a more candid way. One way to encourage participation is by turning the link for feedback collection into a QR code and sharing it right after your last module of programming. These insights will be valuable as you embark on the next event for your founders!

Do you have tips for hosting a Founder Day? Or are you a founder who can share more about what makes a VC Founder Day valuable? Share in the comments below!

Founders taking in some of the structured programming of the day

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Katie Andresen
Better Ventures

Head of Platform @ Better Ventures | Bay Area Native