Welcome back to the Launch Key 🚀
I lived Thomas Wolf’s famous title, ‘You can’t go home again’ last week on a 1200 mile road trip to my hometown of York PA. There were family reunions along with Maryland crab cakes and Pennsylvania scrapple, but change is so visibly obvious when you’ve been gone for decades.
Technology changes far faster than towns. And no matter the time period there is one technology that continues to work.
Let's get into it.
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Table of Contents
Pull to Eject
Last week we talked about writing as the moat. This week, writing into what?
Because here's the thing nobody tells you when you decide, sometime in your fifties, that you'd like to build something with your own name on it: every place you might publish is owned by someone or something else. And that something else has its own interests.
A perfect example is LinkedIn. I’ve got 2+ decades of LinkedIn use and kept my account clean by only connecting with people I knew or worked with. But as I started to publish this newsletter knew I needed additional reach.
LinkedIn decides who sees you. So does X. So do Instagram, YouTube and TikTok. Same for whatever Substack-of-the-month replaces them next year.
The algorithm is not your colleague.
It's a system optimized for engagement, velocity, controversy, and youth-culture cadence — none of which is the natural tone of a 55-year-old operator. Thirty years of pattern recognition are lost in the void.
You can post into that machine for a year and have it decide, quietly, that nobody needs to see you.
There is one exception.
The Permission Medium
Email is different.
If someone gave you their address, they gave you permission. If they open the message, you're in. There is no algorithm between you and your reader. There is only a subject line you've earned, or you haven't. And it’s the reason I chose email as the medium for Launch Key.
That's it. That's the whole architecture.
It's also, not coincidentally, the medium your audience grew up on. Late-career professionals have a complicated relationship with social media — and a clean one with email. We’re used to an inbox. I had a CompuServe address in the 80’s. We’ve been making decisions out of it for thirty years.
So when I tell you that email is the only audience asset you actually own, I'm not making a nostalgia argument. I'm making a property rights argument.
The list is yours. Subscribers can unsubscribe, but nobody can change the rules on you. No platform can throttle your reach to sell you reach back. The platforms are disposable and if you ever leave Beehiiv or Substack or whatever you're using, you simply take your list with you.
Try doing that with your LinkedIn followers.
I Watched this Happen in Real Time
Here’s a case study I happen to know personally.
About three years ago I helped my middle son Clay grow his newsletter – Confluence – which he’d already been building for a few years. He started with topics that were relevant to his work as a private markets investor, and he published religiously every week for ~6 years.
Over that time frame, the community grew to more than 20,000 subscribers from over 1,500 of the premier venture funds. He had grown loyal readers, sponsors, a paid community, and - most importantly - deal flow.
He saw a bigger opportunity to convert that attention into something larger than an audience, and that audience became the foundation Clay is now raising a venture firm on top of - Outlaw Fund I.

Newsletter flywheel: ideas → content → audience → trust → opportunities
Fund flywheel: finding (heavily boosted by audience and opportunities created in fund flywheel), picking (improved with ideas strengthened judgement via writing), winning (improved as newsletter asset differentiates from other investors who provide capital only), and helping (talent pipeline, distribution-as-a-service, downstream capital available to portfolio)
Read that arc again, slowly, because he built distribution first. The distribution then acted as the catalyst for something larger to be built on top of it.
Six years.
No algorithm gave him permission. No platform decided his fate by choosing what was worth amplifying. He earned the open, week after week, until the people opening were the exact people he needed in the room to do the next thing.
Then he did the next thing.
That is what an email list is. It is not a marketing channel. It is a coalition you assembled by being useful in the inbox, and it compounds in a way nothing rented ever will.
What This Means This Week
You don't need 20,000 subscribers. (I know — I have 18,000 subscribers, and I'm telling you, you don't need that many.) You need an opening list of people who would genuinely care if you stopped writing. A hundred is plenty to start. A thousand is a real asset. Ten thousand is a business.
Three things to do this week, ranked by how much they'll matter five years from now:
1. If you don't have a list, start one. Beehiiv free tier. Substack. ConvertKit. The platform matters less than the decision. The decision is: from now on, the people who care about what I'm building have a way to hear from me directly that no third party controls.
2. If you have a list, write to it this week. Not "when you have something polished." This week. The relationship is built by showing up, not by perfection. Open rates beat follower counts the way compound interest beats a lottery ticket.
3. If you have a list and you're writing to it, look at your subject lines. That's the entire game. You don't need better content; you need the email opened. Carlton would tell you the same thing. He was right last week. He's right this week.
The algorithm picked its team a long time ago. It wasn't yours.
The inbox still is.
Now go launch something 🚀
P.S. - Interested in doing something other than a newsletter? Read 12 Encore Career Ideas for Executives (that actually use what you know)
Permission Marketing is the tool that unlocks the power of the Internet.
Old School Wisdom
Seth Godin coined the term permission marketing more than 25 years ago. It’s still pertinent today.
Modern Tools
I’ve used many email platforms over the past few decades, including things like HubSpot, Marketo, Constant Contact and Campaign Monitor. Full disclosure, Clay introduced me to Beehiiv 🐝.
If your business will send newsletters, I can’t recommend it strongly enough.
They’ve made it drag-and-drop easy
They have built-in design tools
They have a very good recommendation engine for other newsletters
Their Advertiser network is robust and growing
They continue to add features to improve your newsletter business
Each week I get suggestions of companies who want to boost or sponsor my newsletter. I simply choose the ones I think will make the most sense for this audience.
Everything is automated: scheduling, distribution, payments, sponsorships, recommendation engine - all integrated with easy-to-use tools. And of course you can launch for free.
Ready to get started?
Click on the logo below to save 20% off your first 3 months of a paid plan after a complimentary 30-day trial.
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🔖 The StartUp Marketing Newsletter : Your cheat sheet for marketing news, insights & tips tailored for the startup space.
Visual Crapshoot

Help me help you: What's the #1 challenge holding back your late career side hustle?
- Financial risk management - can't bet retirement
- Worry that you're not tech savvy enough
- Have connections but unsure how to use them
- Business model selection confusion
- Time management with family obligations
- How to validate product while still employed
- Age discrimination concerns
- Is it too late for my idea?
- Other
Launch Key readers – thank you for your support and feedback. I appreciate each and every one of you as I work to build something you value.
Remember, if there's anything you'd like to share — a recommendation, a story idea, or just a note to say hi, hit the reply button and fire away.





