Hey Reader,

Every founder has an imaginary list called “I’ll get to that in December.”

It follows you all year while you're in the trenches, this dumping ground for everything you don’t have time for but swear you’ll handle when things “calm down.”

Do I need to list them, or are we on the same page...

So. Funny story. December is here. Four weeks to do nine weeks of work... The stuff you pushed off, the stuff you forgot, the stuff you should’ve done already, and the stuff you promised yourself you’d tackle for your “founder glow up.”

Because 2026... is going to different... right?!

Nope. Wanting it to be different doesn't make it different. For something to be different, you have to do something different.

December is the most valuable month for literally every reason, and you have to treat it like day one over and over again, taking nothing for granted. Just a reminder, like every week, this is not an homage to tech bro founder mode. It's an homage to getting you where you need to be fast.

Here are your three modes, pick one.

(1) Nothing changes, you are doing the busy work you've done all year, just fewer meetings, a little more personal time.

(2) The "everyone's checked out" justification for your own slowdown, or for not sending the email or doing the thing.

(3) Going really f*cking hard. As in, last mile of the marathon, you are finishing either way, the question is how you finish.

December is a nice gauge of your commitment level and unfortunately what you are willing to sacrifice. You're exhausted, deserve a break, need a minute, have ignored your family for most of the year, have so much to be proud of. All fair points. I agree, you've been grinding all year.

Just say it. "I'll be back in January" - SAY IT.

It is totally reasonable to know your boundaries for your family, for your health, for whatever matters to you, for your sanity. But you have to know them, have to say them, right now, so you can work into them and not through them.

• If you need December 23-31 completely off, great. Plan for it. Communicate it. Actually do it.
• If you're working straight through, great. Plan for it. Tell your family. Actually do it.

Just don't lie to yourself about what you're doing and wake up in January knowing you could have done more, could have been a little more prepared. Regret is a vicious friend.

If you are playing along, this is what a powerful December COULD look like:

• Close what can close
• Send your end-of-year update
• Align your team on Q1
• Show gratitude (strategic, not soft)
• Do the sh*t you've been avoiding

Also. Your day job of day to day.

Also. Not even talking about your 2026 strategy because if you haven't done it, you probably won't - so we can fight about that next week.

CLOSE WHAT CAN CLOSE

Who in your pipeline has been just sitting there? Who is not moving as fast as you want? Who do you think would actually like to close?

December is the month you up your sales leadership!! Ask the tough questions. Get clarity on where you stand. Close the deal, understand the deal, or move on. Build up the courage to learn the difference between a lead and a buyer.

Let's end December cleaning up our CRM, ask the question you have been avoiding because you fear the answer and acknowledge if you're going to lose the deal, you were going to lose it anyway, because in general, buyers buy.

So many sales plays to run, I have a general belief that if you have spent the appropriate amount of time being of value, being an ally, being genuine to your prospect, then perhaps December you get to just finally, ask the question.... What can I do to make this deal happen?

Here is an example. Hey. You know my book has been out for 45 days, it's charting well, I'm negotiating my second book, if you didn't pick up a copy - please consider it (here) - if you did please consider leaving a review (here).

<< See? Not hard. Because I don't need a favor. If you got this far, you read my emails, you didn't get offended by my ask.

Sure, you could also offer some version of an end-of-year discount or timeline acceleration. Or maybe the end of year isn't critical for you, but you can at least find out where you stand. The point I am making is to ask the question.

Action:

• Audit your pipeline. What can actually close by Dec 31?
• Call every "proposal sent" deal. Don't email. Call. On the phone!
• Ask the question you've been avoiding: "Do you think this is a deal we can make happen?"

FUNDRAISING??

More VC deals close in December than any other month. There's actually data on this. December 15th is (according to Carta) the best week for VC-backed startups closing rounds.

VCs are working. They're closing rounds. Just not with you... yet.

I don't focus on fundraising, there are plenty of better people for that, but having raised $50M+, the rules I know to be true should be accelerated in December:

1. Try to wrap into an accelerated time period, as close to a time box as you can.
2. At least set up your January meetings now. Ask for your intros. Build your pipeline.
3. Make sure any paperwork is updated with Q4 dates. (That one doc you saved as "Pipeline_June_25"? Update it.)
4. If you don't have a fundraising plan, and it's random acts of outbound, and random acts of a weird powerpoint, it would be unfair for you to be shocked if no one gives a sh*t.

I had a boss who would turn your Q4 into his Q1. While everyone else treated October through December as year-end cooldown, he used it differently. He mapped every account. Refined his message. Tuned his outbound engine. Made his critical hires. Lined up every ask.

By January, when everyone else was "warming up," he was in full stride. His January was everyone else's March.

And aside from this guy being an absolute beast, what was insane was how it compounded.

When you're executing in January while others are planning, you're closing in February while others are ramping, you're building momentum others can't catch. The gap widens every month. I watched it first hand. So do it. Because prepping your Q1 GTM now is a massive advantage.

SEND YOUR END-OF-YEAR UPDATE

Send it to everyone. Customers, prospects, investors, anyone who has come across your desk. Have you added all the people you're emailing with into your mailing list? Find a tool. Do it. NOW. (I use Kit*)

Not a generic "Happy Holidays" blast. An actual update. Think about what you want or need. This can be looking back or looking forward or a way to say something you want to say to your prospects. Think deeply about how you want a reader to feel, and write for that, do NOT write for your ego.

Yes, flex a little. Yes, give FOMO for the prospects. Yes, drop massive feature notes like it's not big deal. Yes, include the quote from the customer. Yes, whatever is true and real wrapped in a bow that gets the prospect who has ignored your "checking in" emails for two months to read...

You can be early-stage and still operate with clarity. Choose your tone, choose your style. Show them you know where you stand, where you're going, and how you're getting there. Do not send them to sleep.

I want to read it too. Send it to me. I read every one. They matter. james@startuptoscaleup.com​

ALIGN YOUR TEAM ON Q1

Live, not via Slack, ask the next person you speak to on your team "What are our top 3 priorities for Q1?"

You should stop here and do it. Or don't because you and I know how it plays out. Do they all say the same thing? Nope. Do they all list their own individual objectives? Yup. That's not leading, that's hoping!

Your team needs to know exactly what they're targeting when January hits. Not vague. Not general direction.

If everyone on your team can't articulate your top 3 priorities, you have alignment work to do. December is when you fix that. This is Phase 1 of your 2026 strategy, which you won't do. That's fine. At least do this.

Action:

• Write down your top 3 objectives for Q1. Actually write them.
• Test it. Ask your team what the priorities are. In your ELT / WBS, ask everyone to write them down, real time.
• Share it explicitly. Make it clear. Create alignment.

Just a quick reminder, individual priorities cascade from company priorities. No individual can have a priority that doesn't ladder up to the company priorities.

SHOW GRATITUDE

Who helped you this year? Who opened a door you couldn't open? Who made an intro that turned into something real? Who gave you advice when you were stuck? Who took your call when they didn't have to?

List the people who moved the needle for you this year. Now thank them. One person, one direct message. Be specific about what they did, how it helped, why it mattered, no ask. Just thanks. This will take forever. Do it anyway. Because your competitor isn't.

Relationships are your unfair advantage. Most founders don't do this. You should. You won't. This includes your customers too...)

NEXT WEEK.

By next week, I want you to know your goal for this time next year. Revenue goal is fine, if it's reasonable, feasible, and based on evidence. Grounded in what you're actually building.

What can you actually achieve in 12 months if you execute? That number. Next week we are going to back in to how you are going to get there.

If I can be of service, feel free to grab time.

LFG.

- James

​

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