Gianna's Gem: F-It, Ship It. Lessons from Running Events at Airtable and Windsurf

Hi there,

Last week, Airtable sold to Bending Spoons in an all-cash deal valuing the company at a little over a billion dollars, with an equity value of roughly $2.25 billion once you factor in cash on hand. Airtable was valued at over $11 billion at its 2021 peak. Do the math on that, and you'll understand why the news stopped me mid-scroll.

I was Airtable's first Global Head of Events,  hired at the golden moment the company was scaling fast, pivoting from product-led growth into selling to big Enterprise, and launching an entirely new category: the connected apps platform. I fully expected pivots. I expected delayed approvals on our first major externally hosted events. That's the nature of hypergrowth, and I signed up for it with my eyes open and loved and respected every minute of the grind alongside my colleagues and leaders.

What I didn't expect, and what I still think about, is how much overthinking and conservative rather than bold decision-making crept into the approval process for initiatives like events. This apprehensiveness became deeply embedded in the culture and company’s ability to operate and execute with courage and audacity. Not because anyone was lazy or careless -quite the opposite; these were the brightest colleagues I’ve ever worked with (and I’d worked at Google, Amazon and SoftBank Vision Fund)...everyone cared enormously, which is often exactly the problem. But overanalyzing too much about avoiding a wrong move can sometimes cost you the right one. I can't help but wonder whether some of that hesitation cost us opportunities, and in the case of events the “signaling” we needed to strengthen our brand as we scaled and to have a more successful exit.

Gianna's Gem: Fear can be masked inside a company as "prudence” or "vigilance." But "let's revisit next quarter” slowness has a price tag too, and nobody puts it on the leger.

Contrast that with Windsurf (now Cognition).

I came in as fractional events lead with exactly one event on the calendar: AWS re:Invent. Within four months, we had secured the best location right in front of registration at Google Cloud Next for a bespoke Windsurf Lounge and within six months, we were designing and building our own 1,000-person user conference from scratch. No decades of institutional caution. No fifteen rounds of approvals. Just a clear-eyed, level-headed approach to taking calculated bets based on data and sentiment that the moment called for boldness, and the willingness to move. Fast. I loved the bold culture!

Open Ai announced that they were going to acquire us, but…that event didn’t happen, and neither did our Conference. But that’s because before it could happen, Google acquired the majority of Windsurf in the tech story of July 2025, and Cognition swiftly acquired the remainder within 48 hours. 

Is that a coincidence? I don't think so, and I don't think it should surprise you either. A team that moves at that speed on something as visible and vulnerable as a first-ever conference is a team that's operating with conviction across the board. That kind of energy and bold audacity gets noticed. It gets acquired.

Gianna's Gem: The companies that win aren't the ones with the fewest mistakes. They're the ones with the shortest distance between "we should do this" and "we did this."

Here's my philosophy, and it's not reckless, it's disciplined, but bold and action-oriented: 

Do your research. Budget responsibly. Get crystal clear on the ROI or output you actually want from your event and what absolutely cannot happen. And then, f-it, ship it already.

Gianna’s Gem: With events, there is no bad data.

You either crush it, or you learn something you couldn't have learned any other way. Both outcomes beat the alternative: losing the opportunity entirely because you were too afraid to take the swing, and spending the next year regretting it.

Because here's what a great event actually does for your business:

• It’s a Signal: hosting an event at scale tells customers, industry influencers, press, analysts, and investors that your company is serious, and it builds pride internally in the company's growth trajectory.

• It’s a thought leadership driver: the physical environment to show what leadership means to your company and your community.

• It’s a brand personality exemplifier: the place where your brand comes alive IRL, where attendees immerse themselves in the community in a relaxed environment, and where brand impact and social sharing happen organically.

• It’s an morale and momentum booster: it builds momentum heading into the year ahead.

• It’s a pipeline accelerator: it can dramatically expand and accelerate customer and investment pipeline through the new ideas an event generates.

• It’s a relationship builder: a demonstration of what your company stands for, built through the relationships forged between leadership, customers, partners, press, analysts, and investors.

• It’s an appreciator: a genuine thank-you to the employees, customers, and champions who support the company.

• It’s a feedback collector: a live feedback mechanism for needs, challenges, and honest conversation you won't get from a survey.

That's a lot of value sitting on the other side of a "yes." And the cost of not doing the event is just as real, it's just harder to see on a spreadsheet. In today's environment, agility isn't a nice-to-have. It's often the whole ballgame.

Your Challenge This Week:

Find the event (or other initiative) that's been sitting in "let's revisit it" parking lot purgatory. Get honest about what's actually driving the delay: is it a real resourcing constraint, or is it fear wearing a prudent-sounding costume? If it's the latter, do the research, set your budget, get clear on your ROI, and then give yourself permission to ship it.

If you need help overcoming your fear of hosting an event, let's talk. I'm happy to coach you through it or step in as your fractional head of events to take you to the finish line.

You've got this.

XX,

Gianna.

P.s. Want to work learn more frameworks for creating the gold standard in events and experiences, negotiating, or creating better content for your events? New individual modules from my masterclass are now available at: giannagaudini.com/learn-from-me