Why Inclusively’s Charlotte Dales Flew to New York Unannounced to Save Her First Exit

Why Inclusively’s Charlotte Dales Flew to New York Unannounced to Save Her First Exit

The call came without warning. After months of due diligence, legal fees draining the company’s remaining cash, and the exhausting emotional roller coaster of selling a startup, the M&A lead from American Express delivered the news Charlotte Dales had been dreading: they were pulling the deal.

In a recent episode of Category Visionaries, Charlotte Dales—now CEO and Co-Founder of Inclusively, a workplace personalization platform that’s raised $20 million—shared the story of the most desperate 24 hours of her founder journey. It’s a story about the difference between giving up and getting on a plane. And why sometimes, the only thing standing between liquidation and a successful exit is pure, shameless audacity.

When Everything Falls Apart

It was 2017. Charlotte and her Co-Founder had spent four years building a mobile payments app for restaurants and bars in London. They’d grown to 200 locations. American Express wanted to buy them. The deal was happening.

Then it wasn’t.

“We got a call from the person who was leading the deal and she was, you know, very nervous to call me. And she knew how much it meant to us to sell this company. And you know, that we had paid, you know, so much money and lawyers and everything, you know, were basically doing this. We were putting everything into doing this transaction. We had done jump through all the hoops. And she said, you know, we’re not going to be able to do it,” Charlotte recalls.

The timing couldn’t have been worse. They’d already invested heavily in the transaction. Legal fees. Due diligence preparation. Opportunity cost. “And I was just like, that just can’t be true. Like, we’ve done everything. We thought through diligence, we did everything.”

Her board and M&A advisor saw the writing on the wall. “I just called my board and I said, and we had an M and A advisor. And I just said, you know, they were kind of like, you know, talking about just going into liquidation and all these options.”

Charlotte’s response was immediate and instinctive. “And I was like, that’s just not happening. I’m going to New York. If someone wants to come with me, they’re welcome to come.”

The Eight-Hour Gamble

What happened next was either brilliant strategy or calculated desperation—probably both.

Charlotte knew she had one advantage: the M&A team and her point of contact wanted to do the deal. “Like the M and A team wanted to do the deal, this person wanted to do the deal. But you know, in big companies lots of things can just change. People leave and they can just kind of, you know, quickly pivot.”

The problem wasn’t the people who knew her company. It was the people who didn’t. Someone in Croatia who had decision-making power had pulled the plug without ever meeting Charlotte or understanding what they’d built.

So Charlotte engineered a situation where American Express couldn’t say no until she was already in New York.

“This was kind of back when you didn’t really have WI fi on airplanes. And so at 9:00am London time, I was on the plane, sent the text as were taking off to my point of contact there and said, I’m on my way to New York from London and I’ll land at 1pm and I’ll come by the office. Then, you know, took off and had eight hours of no service and landed.”

Read that again. She sent a text saying she was coming, then deliberately became unreachable for eight hours. “I strategically did it because I was like, you know what? They’re going to know I don’t have Wi Fi, so they’re not going to be able to tell me not to come. Like, I didn’t give them enough time to redirect me.”

When she landed, American Express had spent those eight hours figuring out how to handle her. “And you know, they had all had a lot of time to kind of figure out what to do. And they’re like, okay, you please don’t come in today. Like we need to get the right people.”

But it was too late. She was already in New York. And importantly, her audacity had forced them to escalate. “And they wanted to do the deal. Like the M and A team wanted to do the deal, this person wanted to do the deal.”

The Whiteboard Pitch That Changed Everything

American Express didn’t just agree to a quick meeting. They got the President of the Consumer Group—someone who hadn’t been involved because the deal was too small (under $20 million) to merit her attention.

“And so luckily I actually got to go to the top. And, you know, I went in and the M and A advisor and the woman who was running the deal on the team, we met for an hour before the president came in.”

Charlotte and her team had spent weeks perfecting pitch decks and presentations. None of that mattered. “And, you know, we spent all this time, like, doing all these perfect decks and making everything perfect. And the end of the day, I was writing a whole pitch onto a whiteboard, waiting and presenting that to the president of the consumer group at Amex.”

The President of the Consumer Group wasn’t even really part of the deal process. “And I think she, you know, like, she wasn’t really part of this was a small deal for Amex, so she wasn’t even really part of it. It’s under 20 million. And so, you know, after, like, getting to hear from me directly what was going on and why I thought this was valuable to the company, they said, you have this one piece of functionality. And I was like, yes, we do.”

That’s when Charlotte got her opening. “And so they said, okay, we’re going to send someone over for diligence, you know, in a week or two to confirm all of that. And then, like, we can start to think about moving forward again.”

Charlotte flew back to London and built what they needed within a weekend. “And so went back to London and we built what they needed within a weekend and got through the diligence and closed the deal.”

Would It Have Worked Without the Flight?

The obvious question: was the dramatic flight necessary, or just theatrical?

Charlotte doesn’t hesitate: “100,000%.”

The deal would have died without that flight. The phone calls wouldn’t have worked. Email wouldn’t have worked. Waiting for the right moment wouldn’t have worked. The only thing that worked was forcing American Express to deal with her in person, immediately, at the highest level possible.

“And you know, when the deal closed and when were kind of started working at the company, like, they bring up this story, you know, the woman who ran the whole deal is actually now an advisor of my company now. And I mean, the story just comes up all the time.”

Years later, the President of the Consumer Group told Charlotte directly what the flight meant. “When I eventually left to start this company three years later, she was just like, that was one of the most amazing things I’ve ever seen. And, like, you got getting on that plane just like says everything about you.”

The Deeper Lesson About Founder Leverage

Charlotte’s flight wasn’t just about persistence—it was about understanding her leverage.

“And so I just feel like as an entrepreneur, you just really have to not, like, you just can’t have any shame. Like, there’s just nothing more important than showing how much you care about, you know, moving your business forward.”

She had nothing to lose except a plane ticket. “Like, we had everything to lose. Like, I had nothing to lose besides a plane ticket.”

The board was already discussing liquidation. The deal was already dead. The conventional playbook said to accept reality and move on. Charlotte recognized that conventional wisdom only applies when you have something to protect. When you’re already at zero, audacity costs nothing.

This is the calculus that separates founders who close impossible deals from founders who accept reasonable explanations for why things didn’t work out. Charlotte didn’t have a better pitch or a more compelling product. She had a willingness to be uncomfortably bold when everyone else was being professionally resigned.

The Principle Behind the Tactic

Strip away the dramatic flight and the whiteboard pitch, and you’re left with a simple principle: create situations where the other party has to engage with you on your terms, not theirs.

American Express was comfortable pulling the deal over email and phone calls. Charlotte made herself physically impossible to ignore. She forced them to escalate to people who could actually make decisions. She compressed what would have been weeks of back-and-forth into one high-stakes meeting.

The eight-hour communication blackout was genius because it prevented American Express from controlling the situation. They couldn’t redirect her to a phone call. They couldn’t delay. They had to deal with the fact that she was coming, and they had limited time to decide how to handle it.

When to Get on the Plane

The obvious question for founders reading this: when is this tactic appropriate?

Charlotte’s situation had specific characteristics that made the flight make sense:

• The deal was effectively dead (nothing to lose)
• The people she’d worked with wanted it to happen (allies inside)
• The blocker was someone who didn’t know the company (information asymmetry)
• She had the financial resources for the flight (risk was contained)
• The deal size justified the effort (under $20M but still significant)

If any of these factors had been different, the flight might have backfired. But Charlotte read the situation correctly and acted decisively.

The broader lesson isn’t “always get on a plane.” It’s “when you have nothing to lose and everything to gain, don’t let professional convention stop you from doing what needs to be done.”

Charlotte built Inclusively with this same philosophy. When traditional marketing stopped working, she didn’t optimize—she rebuilt from scratch. When her ICP needed to change, she didn’t gradually transition—she pivoted completely.

The flight to New York wasn’t an anomaly. It was the origin story of a founder who understands that sometimes, the only way forward is to do something that makes everyone uncomfortable—including yourself.