StartUp Founders: T-21 Days. Ready?


Hey Reader,

Don’t say it. December’s a dead zone. Investors are skiing, customer "out of offices" are already appearing, and you've put your pipeline & outbound on ice.

I don't buy it, but let’s pretend I agree. That leaves one option…

T-21 days. 504 hours (300 working hours?). To roll into 2025 ready to just f’n explode. Jan 6th. First Monday back. That’s your moment of truth.

This isn’t the end of a year. It’s the start of one.

While everyone’s mumbling their “New Year, New Start” mantra, you better be gearing up and already in motion, ready to EXECUTE on day one. Otherwise, you’ve already lost Q1.

If you didn't build your strategy, you can’t blame the market for your failure to do the hard work.

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HYPER RELATED:

Last week rattled some feathers: You don’t do product. You don’t do growth. You don’t do innovation. You don’t do funding. You don’t do disruption. You don’t get to self-name these attributes. They are given to you. By the market. They are outcomes.

LETS GET INTO IT:

Most founders write off the stretch between Thanksgiving and New Year as dead. It’s not. It’s Q5. The pocket of weeks that everyone gets, but few actually leverage.

I had a boss who would turn your Q4 into his Q1. While everyone else treated October - December as a year-end final close / cooldown, he used it to map every account, build his strategy, tune his engines, refine his message, make his critical hires, and line up every ask. By January, when everyone else is just warming up, he was in full stride, his Q2.

First. Your Pipeline: Two Customer Types

  • Not-Ready-to-Close: Send a personal holiday note. Real gratitude, real connection. No automation, no templates, no hidden agenda, no growth hack. Just genuine appreciation. If you can't think of something personal to say, you're not building relationships, you're collecting contacts and haven’t realized sales is a personal journey.
  • Proposal Sent (HubSpot Column): Most founders avoid tough questions because they fear tough answers. It’s time. Pick up the phone or jump on Zoom: “We’ve been working on aligning our solution to your needs. Do you think this is a deal we can make happen?” Direct ask, clear intent. If you lose them now, you were going to lose them anyway. If not, you’ll get clarity on the close plan.

    I’m not worried about whether it’s 15 days or 5 days before the new year. That’s not the point. I’m focused on forcing you to ask the question that’s been living in your head since the prospect entered your pipeline... will it close.

Second, Your End-of-Year Update

Send it to everyone. Customers, prospects, investors. Show them the future they want to believe in.

  • Thank You: For sticking with us, giving feedback, being part of this journey.
  • Our Outcomes: The real, tangible results you're fighting to deliver.
  • Our Execution: The wins, the lessons, the behind-the-scenes peak into your soul.
  • Our Continuation: How you're doubling down, no matter what.
  • An Ask: Why not ask for something you need (not funding).

They know you’re early-stage. They know it’s not all sunshine and rainbows. Transparency is an underrated quality. Show them you know where you stand, where you’re going, and how.

I want to read it too, add me to your mailing list.

More Important: Your team needs to know exactly what they’re heading when January hits. Not vague growth goals or general direction, crystal clear and absolute objectives and priorities. It would seem reasonable to ask if everyone in your company knows your top 3 objectives? Can they? Ask them...

.....Fighting the urge to scrap this entire newsletter and rewrite it as a manifesto against founders who isolate knowledge, treat objectives like classified info, and push people to stay in their lane. Don’t do that. Make it explicit. Share it. Alignment matters.

So. Before January 6th...

  • Account planning - know exactly who you’re targeting
  • Prospect heat maps - know your buyer profiles per target
  • Messaging - refined, deployed & ready
  • Outbound engine - tested & tuned
  • Dashboards - simple, clear & actionable
  • Alignments - a fully sync'd team
  • Blockers - identified & addressed
  • All of it.

Wake up January 6th in execution mode. Do the hard work now.

As always, if I can be of service, feel free to grab time.

LFG.

-- James

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Where 140k+ founders read my weekly newsletter offering tactical insights to start, scale, and fund their startup. Real advice from a 3x exited founder.

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