Hey hey,
Happy Saturday. This one is personal.
The Level Set:Â You may think that making sales and having consistent income is the hardest problem in your business.
But there’s a sneaky problem lying underneath that’s tripping you up. If you can’t clearly communicate the painful, pervasive, urgent, expensive business problem you solve, for the companies you hope to sell to, you’re dead in the water.
This edition is about how to move before you feel ready. Plus, an invitation to my FREE 5-hour Sales Intensive!
This Week's Shift: Waiting for clarity → deciding with the data you haveDelivering a clean answer to, "So what do you do?" is one of the hardest things for experts like us to clearly communicate. It's frustrating as hell. Why is it so damn hard?
You left corporate with an extraordinary amount of wisdom, pattern recognition and expertise. And since you were busy developing that expertise over the last 10-25 years, you might have been a touch too busy to also learn: positioning, packaging, pricing, marketing, sales, copywriting, technology, finance, accounting, revenue operations, or how to run a boutique company.
You’re not alone. Even I have changed LevelUp’s positioning 4 or 5 times, and our offers more times than I can count.
3+ years of being wrong in increasingly useful, yet exceptionally painful, ways has taught me a thing or two. Fortunately, I took notes. Here are some of the best lessons I’ve learned so far this decade:
Business clarity is NOT something smart people can think their way into. You EARN clarity, a little bit at a time. You make the best decision you can with the information you have at the time. Take action, collect more information, rinse and repeat.
The entrepreneurs who make it simply demonstrate more grit and resilience. We learn how to eat shit and be wildly uncomfortable most of the time. But we get back on the horse every single time we get knocked off.
And each time we get back on, we design the next experiment, with better data. Here is the loop: learn → take action → learn → take action → learn → take action. You get the gist.
Write a hypothesis in pencil. Take it outside. Say it to real people. Try to sell it. Listen carefully when they do not understand it. Watch what they buy and what they do not. Reflect on what happened. Change the hypothesis. Get back on the horse and try AGAIN.
That is how you earn the next layer of clarity. One rep, one reflection at a time.
What This Looks Like in Real Life
In the Summer Sales Accelerator that just wrapped up, the single most revisited exercise across all eight weeks was a clear positioning statement. One or two sentences. Accomplished founders and consultants rewrote that sentence more times than anything else we worked on, because compressing real expertise into one clean line is brutally hard.
YET it is also the highest-leverage work in the business: everything downstream gets easier once those 30 words are true. I have said every one of these to myself:
I should be clearer before I put myself out there. I should have the exact architecture of my offer figured out before I start talking about it. I should know exactly who my ideal client is. I should be ready.
Please stop shoulding on yourself. Doing the actual work is what makes you ready, not sitting at your favorite coffee shop dreaming up what you think your customers want.
→ Your Next Move
Write the one-sentence version of what you do, in pencil, using only the information you have today. Say that sentence out loud in three real conversations this week. Watch faces. Note what lands and where eyes glaze and show disinterest or confusion. Then revise from that data while it is fresh.
That is a real rep plus a reflection, and it beats another month of thinking about it.
Why This Matters
The market is moving faster than it has at any point in our careers because of AI, and my job is to stay a couple of steps ahead and quickly turn back to share my learnings with you.
And right now, I promise your biggest progress will come from iterating live, even when it is painful, even when you feel exposed. Waiting until you feel ready is playing small, and you playing too small is the thing I am here to squash.
You deserve to make the money you are actually worth (which was not your corporate salary, but more) and live a life you enjoy, doing purposeful work that creates deep impact, with clients you love to work with.
On September 11th, I am giving away five hours of my time, and we are going to work, together. We will: - crystalize the expensive B2B problem you are uniquely equipped to solve
- define who owns that big problem inside the companies you actually want to work with
- how to position yourself around that problem in a way that deeply resonates with your buyers
- Then we’ll do the money math to ensure the business you are designing supports your life, not the other way around.
- You will leave with strong hypotheses for your entire business foundation, written in pencil, ready to take into the market for refinement.
I’m in year 26 of my career and only this month did I crack the code and write a formula for you on how to write a deeply compelling, resonant positioning statement that will cut through the noise, and get you in the door. September 11. Five hours. Live. FREE. No replay. Come do the work with me.
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