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How to Plan a Top Tier CEO Summit for your VC Firm – A Conversation with Stephanie Rich

Belle Raab
Why does your VC firm host CEO Summits and how many have you done? Is there anything you wish you’d known/realized before your first CEO Summit? If you had to go back in time and try and convince your investment team to allocate a budget for a CEO summit, what points would you use? What costs of a CEO Summit are typically covered by the firm vs founders? What’s something you’ve tried at a summit that you’d never do again? What’s something you’ve tried that you’ll make sure to always do in the future? Any tips to maximize the budget/value add ratio for coordinating a CEO Summit? Is it worth attempting a virtual summit these days or do you think it needs to be in person?
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VC Head of Platform shares advice on how to plan a founder-focused CEO summit.

About Stephanie Rich

Stephanie Rich is Head of Platform at Bread and Butter Ventures where she builds scalable networks, resources, tools and knowledge that help their portfolio companies succeed. She spends time working in the Twin Cities startup ecosystem and mentoring founders building in food/ag tech, digital health and enterprise saas. Before working in VC, she gained experience in early-stage marketing and building brands and communities. And she love dogs.

You can find Stephanie on LinkedIn and Twitter.

Why does your VC firm host CEO Summits and how many have you done?

Stephanie: We did our first official Summit in the summer of 2023. We invest all over the country (actually the world!) so we wanted to host a Founders Summit to bring our portfolio together to build connections between founders as well as to meet our network in MN. Our goal for the event was to have everyone leave feeling inspired, motivated and armed with something new -whether a new contact, new resource or new skillset.

Is there anything you wish you’d known/realized before your first CEO Summit?

Stephanie: I wish I’d thought (and perhaps tested) the space we used a bit more. I’d recommend really thinking about how you’ll utilized Summit locations for big presentations, workshops but also for small moments for founders to connect in small groups. The space was still great, but I think it would have been even better if we’d approached it more thoughtfully.

If you had to go back in time and try and convince your investment team to allocate a budget for a CEO summit, what points would you use?

Stephanie: I’d focus on the benefits that our founders would get out of summit – connection, inspiration and motivation. Zoom is great but there’s something about getting people together in person that solidifies founder to founder and investor to founder relationships.

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What costs of a CEO Summit are typically covered by the firm vs founders?

Stephanie: Depends primarily on two things – size of the firm and amount of sponsorship dollars raised. At the least, firms should plan to cover all activities and food throughout the event – if you have the budget for it we recommend covering (or at least subsidizing) accommodations and travel.

What’s something you’ve tried at a summit that you’d never do again?

Stephanie: We did basically all of the planning and prep in-house – it was fun but a ton of lift from our team. Next time I will probably work harder to figure out what different things we could partner on or hire someone to handle – especially when it comes to design and audio-visual skills.

What’s something you’ve tried that you’ll make sure to always do in the future?

Stephanie: We did a great session where we had one founder briefly interview another in front of the whole group – and we repeated this about 10 times. I was blown away by the amount of research founders did to prep for this – they asked each other insightful, thoughtful questions that really led to all attendees a great window into what each person is building, the journey they’ve taken, and the things they think about every day while running the company. It proved to be super inspirational and led to lots of connections afterward.

Any tips to maximize the budget/value add ratio for coordinating a CEO Summit?

Stephanie: Spend money on your high-value things – speakers, major dinners/experiences, location – and find ways to deliver on the details in a more budget conscious way. Also be creative when it comes to the city you host in. While there are certainly advantages to hosting in hot spots like San Francisco, New York or Miami, you can save a ton of budget by holding your summit in a city like Minneapolis where buying our restaurants, securing venues and paying for activities requires significantly less investment.

Is it worth attempting a virtual summit these days or do you think it needs to be in person?

Stephanie: Part of me completely understands the desire for a virtual summit – it’s so much more cost efficient but keep in mind you’re really missing out on the in-person connection and inspiration that make in-person summits so magical. I’d also say a virtual summit is only worth it with extremely stellar and useful content. Make sure you’re giving people a real reason to show up and be very cognizant of the length of event.

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