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Extra Extra

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EXTRA EXTRA

A newsletter about early sales from The Extra Group

In the lead up to my Path to Repeatable Sales program launching on September 16th, you'll be hearing from me a little more than usual. Same hot takes about startup selling, just a little more often, for the next two weeks.

Olympic athletes do not play about their mental game.

So why do founders?

Name an Olympic athlete. Guaranteed, they've got a kinda-out-there mental ritual that helps them perform and win.

Michael Phelps famously ran through visualizations before every race. He didn't just visualize what every second of a winning race would feel and look like -- he went through the worst case scenario too. This practice kept his anxiety at bay (and also helped him win gold in Beijing when his goggles had filled with water and he was essentially swimming blind!).

Sha’Carri Richardson has a strict daily ritual of positive self-talk in the mirror. Every morning she looks at herself and says “you are you, and you are enough.” (😭😭😭)

And of course, Simone Biles doubled down on managing anxiety and overwhelm after she came down with "the twisties" during the 2021 Olympics. She went on to win four medals in the 2024 Games.

For founders, these investments into your mental game can seem nice-to-have, silly, or a waste of time. But they're not. For athletes at the top of their game, they are just as important as their physical training.

Worry and self-doubt take over for so many founders. You might worry about coming across as pushy, your product not being good enough, or not having the answer to every question.

It is completely fair to feel all these things. But these stories don’t help you perform.

It’s hard work to shift a mental narrative. In fact, it's much easier to focus on more tangible activities like “just booking more calls” or “I just need to increase urgency with my buyers."

But if you find yourself avoiding the rejection that comes with regular selling, feeling out of control on sales calls, or stressing out about the quality of your MVP – you'll want to gently tend to your mental game. It’s an underrated tool to accelerate your startup's performance and revenue.

The mental game is a key component of my upcoming Path to Repeatable Sales program. It's especially present in the back-half. We start with teaching you the tactics that help you define your buyer hypothesis and book and run sales calls. But once we start applying those tactics? That's when I see the mental game become an accelerant or a hurdle. We have time and exercises built in to help you address any blocks that come up as you start selling more, like anxiety, avoidance, defensiveness, and perfectionism (and yes, I had to work through all of these when I myself was a founder, don't you worry). If you want to get your sales tactics dialed in and build the mental game to win as a founder, let's hop on a quick call.


upcoming events

"My Product's Not Ready" and five other myths about early-stage sales

Wednesday September 3 at 12 ET

​If you've found yourself mysteriously blocked on sales despite your best intentions, this workshop is for you. We'll cover the common myths that founders hold about selling and reframe them. You'll leave with new perspective, agency, and tools to win deals and manage the mental game of selling. Register here.

This is Extra Extra, a newsletter about the tactics and mindsets that drive early sales. I’m Caroline Fay, an exited social impact founder who’s spent my career launching and selling new products. I help non-traditional tech founders build sustainable, recurring revenue.

grow revenue ON YOUR TERMS

  • Early Sales Cohort Program: A new, more cost-effective way for founders to get all the curriculum and coaching needed to reach sustainable, recurring revenue. The next cohort starts on September 16. Have questions? Let's chat.
  • Sales Consulting: If you’re looking for completely custom 1:1 support to grow or refine your startup’s sales process.
  • Trainings for Accelerators: Sales workshops for early-stage founders, from someone who's been there.

Caroline Fay

67 West Street #GP24, Brooklyn, NY 11222
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Extra Extra

Extra Extra is a newsletter about the tactics and mindsets that drive early startup sales. I’ve helped dozens of startups get results like a 50x in repeatable revenue and a 400% lift in sales calls per week.

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