WeatherPromise

Reframing proof into upside

Working together, we identified the gap: WeatherPromise had proof, but it fell short on framing. They signed partners like Expedia, but they were presenting that as a box checked rather than evidence of how much bigger the business could become. Instead of making investors imagine the next stage of growth, they were being told the case was already made. 

Things changed when they started viewing traction as the floor, not the finish line. The ceiling was higher than assumed. 

"As the European co-founder, I'll say that being fairly aggressive in our projections and in the way we present stuff doesn't come naturally to me," David said. 

But it was necessary.

That reframe was evidenced by a single slide David still points to: an exponential upside curve, built to pair the new message with a visual that investors could feel.

"That was a good way of message and visual coming together," David said. "It still makes it more believable."

They were still presenting the same facts, but they were aimed at a different question: Do you see what's still ahead?

Turning rehearsal into real preparation

From the first working sessions, it was clear the deck alone wasn't the problem. The co-founders had pitched enough times before to know the material cold. They hadn't yet been tested on whether that command translated under real pressure. How would that message actually sound out loud? Perhaps more importantly, would it work with two founders splitting the room?

We ran David and Daniel through mock pitches with a Hollywood-trained actor. They rehearsed the presentation the way a performer prepares for a live audience rather than just a slide-by-slide readthrough. That process surfaced specific language that could be dropped, phrases that weakened the pitch without either founder realizing it, and the process forced both to know exactly what belonged on every slide, without hesitation.

That process produced three things that didn't exist before:

1. A clear, rehearsed answer for what each slide was actually there to say
2. A deliberate split of who spoke to what, so two founders in the room read as one coordinated pitch and not just two overlapping ones
3. Talking points committed to memory, so David could pitch five or six times a day on a single trip without the material itself costing him energy. Cue cards were just the backup

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Learning how to tell the best version of the story they already had without hesitation was the foundation on which the rest of the pitch was built.

Turning the close into leverage

The round closed at $12.8M, more than three times oversubscribed, led by Maveron with participation from 1Sharpe, Lerer Hippeau, Clocktower Ventures, Commerce Ventures, MS Transverse, Start Ventures, 1Flourish, and former Expedia Group CEO Mark Okerstrom. This round brought the company’s total funding past $22M.

With it, came something harder to quantify than capital: time. With three years of runway, the company's focus on growth becomes much sharper.

"I can build the company now without having to think about the next fundraising," David said. "You can start stuff that takes two years to come to fruition because you don't have to worry about the next fundraising cycle." 

WeatherPromise had a term sheet within six to seven weeks of starting pitching. With a limited window on the ground during a West Coast trip, the team gave investors a deadline: Meet now, or lose the opportunity. That, plus a sharpened message, turned interest into three competitive term sheets, with the final offer winning.

For a travel-tech company, David called it a respectable raise in its own right: "If you look at AI, it kind of all feels like peanuts. But we're not in AI, and we're very happy with that result."

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More than a polished deck

For WeatherPromise, the confidence of being well-prepared went beyond the deck. Knowing exactly what each slide said and knowing how the co-founders would split the room and how the messages, slides and delivery all worked together at once was the difference.

Diligently rehearsing mock pitches gave the founders confidence and comfort that only comes when you know you are fully prepared.

WeatherPromise had in-house designers, and they could have made something just as visually polished on their own, but that was never the point.

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The pitch got sharper, but the business underneath it never changed. Synthesizing the message and preparing to tell it better helped WeatherPromise close its Series A three times oversubscribed.