Your Boxing Day business gift

Hi,

Welcome to bankrolling tomorrow, your no BS guide to capital raise.

Hope you had a very Merry Christmas yesterday, and wishing you a happy new year ahead.

Since it's Boxing Day, I'm conscious to not take up much of your time while you're probably still in a food coma or untangling yourself from wrapping paper.

So cutting straight to the point: this week, I broke down PayPal's capital raise, and as a Christmas present, I'm going to give you one thing you can take away from PayPal, and apply it directly into your business.

Stop running from customer concentration - lean into it.

PayPal raised $216M while 67% dependent on eBay. Sounds terrifying. But that "risky" dependency gave them exactly what startups desperately need: massive volume, real user data, and constant feedback. Instead of spreading themselves thin trying to diversify, they used that concentrated demand as rocket fuel to build world-class infrastructure faster than anyone else.

The lesson? If you've found real traction with a concentrated customer base, don't immediately panic and try to diversify. Use that momentum to build something stronger, raise capital, and become indispensable. Most startups fail because they never find that initial fire - if you've got it, feed it.

Customer dependency isn't always a weakness - sometimes it's exactly the accelerator you need to build something unstoppable.

Something to think about as you digest yesterday's turkey (or whatever your Christmas feast was).

It's been an incredible journey sharing these insights with you this year - hopefully they've helped you dodge a few fundraising landmines or will give you some ammunition for 2026. You won't hear from me again until January because this is the time to put the laptop away, watch an enormous amount of Christmas movies, and actually be present with the people who matter most. around me.

But if you have any questions until then, or need to chat about anything, just drop me a reply and I'll get back to you ASAP. 

See you in 2026!

Talk soon,

James