Why Do Most Startup Conferences Suck?

Most startup conferences suck because of three things: format, content and speakers.

Format — Conference organizers love panels because they are really easy. Usually they recruit a moderator who then recruits 3 or 4 (and sometimes 5) panelists. Panels suck because of poor moderation. Panels are rarely conversations. They are often repetition of what each panelist thinks in response to the same questions — a little bit like watching a zipper go up and down. Some conference organizers have adopted the “fireside chat”. These can be a big improvement over the dreaded panel BUT it is still the same format — other people having a great time having a conversation that you, in the audience, watch.

Content — Most startup conference content is not that meaningful or actionable. It is either what you already know or it’s not very useful. Speakers like to talk about their businesses — everyone is in sell mode. They have a talk track, a public persona for themselves and their company that has been carefully crafted by PR professionals and repeated often. They want and need the world to think they are great, that everything is working exactly as planned and that they are unique in their success. How is this useful for you? How can you learn from them? What playbook can you take home to implement the next day?

Speakers — In a bid to sell tickets and attract attendees, organizers find high profile speakers like unicorn CEOs who offer little in the way of authentic insight into their path to success or actionable advice that can be put to use immediately. Why? Most of them live in a reality distortion field and few want to talk about the hairpin-turn journey that got them to where they are. And, at most conferences, the speakers are ushered in through a back door and when they finish their talk, they leave through that same door, by-passing the audience. Have a follow-up question or want to set up a meeting? Forget it. You are a mere mortal startup founder.

So, I designed a startup conference to fix all of these things. It’s called Flying Upside Down and it takes place at the Hiller Aviation Museum in San Carlos, CA on May 23, 2017. Here is what we are doing differently to make this startup conference suck (way) less.

Strictly Mobile 2014, Computer History Museum, Mountain View, CA

Format — No panels or fireside chats just speakers engaging directly with the audience. I learned how powerful this format is first-hand when I gave a TED Talk in Brussels. Talks average around 18 minutes, with some a little longer at 30 minutes and others (I call them vignettes) at 12 minutes. Lots of variation makes for a more interesting agenda. We also have a morning networking break and an extra-long lunch with opportunity to meet with speakers and fellow attendees, tour the aviation museum collection, and try your hand at the drone academy or VR lounge.

Content — Content that is useful and meaningful. As a pilot, startup founder and early stage VC, I have built the content for Flying Upside Down around the Four Forces of Entrepreneurship. Real advice to tackle every stage of the start-up journey, from high-level strategy to tactical execution, with new mental models for navigating the challenges of growth and real insights to put in motion tomorrow.

Speakers — Authenticity. I have personally curated a line-up of speakers who will tell it like it is, success and failure, and how to navigate the myriad challenges faced by startup founders and innovators. There are three kinds of talks being given: Keynotes (big concepts), Master Class (actual game plans) and Founder Vignettes (authentic founder stories). At Flying Upside Down, all of our speakers are attendees too and they are available to network and talk with you throughout the day.

Here are a few of our speakers, why we selected them and why you would want to hear what they have to say:

Al Ramadan, who wrote Play Bigger: How Pirates, Dreamers, and Innovators Create and Dominate Markets, is working with some of our portfolio companies at Relay Ventures on how to be a category king — the science behind the strategies that innovators use to create and dominate product markets.

Greg McKeown who wrote Essentialism: The Disciplined Pursuit of Less helped my team at Relay implement his model — it isn’t about getting more done in less time. It’s about getting only the right things done.

Amy Wilkinson interviewed 200 entrepreneurs with start-ups generating >$100MM in annual revenue, including Airbnb, Chipotle, Dropbox, eBay, LinkedIn, Palantir, Tesla, 23andMe, Under Armour and Yammer. For her book The Creator’s Code she decoded The Six Essential Skills of Extraordinary Entrepreneurs.

The rest of the speakers aren’t too shabby either:

Chris O’Neill, CEO, Evernote — The Playbook for Building and Growing Products, Brands and Teams

Matt Munson, Co-Founder, Twenty20 — How I Burned 10 Million Dollars So You Don’t Have To

Jen Holmstrom, Head of Talent, GGV Capital (previously Facebook) — How to create high-performing teams and winning cultures

Angus Davis, Founder, Upserve (co-founder TellMe) Flying Lessons — the most important and relevant lessons from flying

Acacia Leroy, Asia Pacific Trend Strategist, TrendWatching Asia: Disruption 101 — What You Don’t Know Will Kill You

Norman Winarsky, Author, If You Really Want to Change the World Creating, Building, and Sustaining Breakthrough Ventures

Spiros Michalakis, Quantum Physicist, CalTech Facing Insurmountable Obstacles When Probability is Against You

Jacco Vanderjooij, Author, Blueprints of a SaaS Sales Organization The Art of Making Love

Rob May, CEO, Talla Top 5 Fundraising Lessons for Entrepreneurs

Geoff Clapp, Co-Founder, Better Flying Too Close to the Sun — Failing to Find Appropriate Product Market Fit

Lt. Col. Rob “Waldo” Waldman — Decision making at 1,450 MPH

Format, content and speakers are typically why most startup conferences suck. What I have done with Flying Upside Down is build a full-day program that respects the entrepreneur’s time, delivers valuable and impactful content from authentic speakers (many of whom are entrepreneurs themselves) and to deliver this all in a format that is proven, informative, accessible and fun. Along with breakfast, lunch and amazing snacks from Foxtail, the hottest caterer in the Bay Area, in an amazing venue, the Hiller Aviation Museum, Flying Upside Down is an event that will change your opinion of startup conferences.

Note: For the last seven years I have curated and produced a Bay Area conference called Strictly Mobile, a half-day summit for mobile influencers to discuss the future of mobile computing and its impact on the world in such diverse categories as the democratization of education, consumerization of healthcare, mobilizing the enterprise and connecting the home and car. This year, I decided to replace Strictly Mobile with a completely new, full day summit for startup founders which I called Flying Upside Down (based on the notion that entrepreneurs and pilots have a lot in common).