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Welcome back to the Launch Key 🚀 |
Three years ago this week, I hit send on the very first Launch Key. |
158 weeks later, I want to do the most important thing - and that is Thank You. |
I get enough ‘atta boy’ texts, emails, comments and poll responses to tell me that you find some value in this newsletter. And its a solid creative outlet as my old guy side hustle. |
So this issue is our Year 3 review, plus I’ll show a little about how this newsletter actually gets made. Then I need your help deciding what comes next. |
Let's get into it. |
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Table of Contents |
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Pull to Eject |
Year 3: the year I chose smaller |
I've done this look back twice before, in year one and year two. I don’t need to rehash how Launch Key got started, but having an audience and a weekly publishing cadence has been a great experiment for me - and I am grateful. You’ve given me the ability to try new tech, creator economy trends, improve my writing and test ideas in a real time sandbox - all while understanding that you can unsubscribe at any time. |
After a flood of new subscribers last year, the thing I’ve been working to improve this year is engagement: your open rate is back to about 39%. That's roughly two out of every five of you, every Tuesday. |
It didn't get there by accident. Year 3 was the year I stopped chasing a bigger list and started building a better one. |
Three decisions: |
I cleaned house. I ran re-engagement campaigns, and when people didn't open or click, I removed them. Just like web sites need content gardening, it turns out newsletters require subscriber gardening. It felt like firing customers. But it was the right call. I stopped paying for subscribers who didn't stay. I’ve spent more than $5,000 on paid acquisition and referral programs. The subscribers showed up and then quietly disappeared. Paying for a list that doesn't read you is the wrong vanity metric. I built things that last. I once thought SEO was a dumpster fire. But I started the year by moving the Launch Key domain to Beehiiv to simplify findability. I worked with Google to improve search of published issues. I also wrote a few evergreen articles, like 12 Encore Career Ideas for Executives, The Late-Career Entrepreneur and Start a Business Without Risking Your Retirement. And I showed up on LinkedIn most weeks. New readers now arrive because they went looking for this exact type of content.
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The list is a little smaller. The room is a little better. |
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The message got sharper |
Early Launch Key said something close to "it's never been cheaper to start." That's still true. I even made it a free download. |
But three years of writing, and a lot of your replies, sharpened it into this: tools are the commodity. Experience is the moat. |
I first wrote that technology is a commodity, even AI back in 2024. By this summer it was simply always the commodity. |
AI can write, code and design for anyone. It can't hand anyone thirty years of watching deals go sideways, clients walk away, or the "sure thing" fail. Nobody hires a calculator. They hire the judgment. You already have it. That's what this newsletter is about now. |
How it gets made today |
This year I told you that AI has become an important part of my process. I haven't completely shown you the system I’ve built. Here it is. |
1. The capture layer: a Notion second brain.
Every idea lands in a Notion inbox. That means a tweet, a podcast line, or something I said on a panel that I'd like to say better. I can add ideas manually, I can ‘talk’ them in via Wispr or I can ask Claude or Grok to add entries with links etc. Notion connects my library of career digital examples, favorite books, pdfs screenshots and case studies. From there, good ideas become seeds in a newsletter pipeline, and each seed moves through stages: Seed → Developing → Drafting → Published. |
The key: seeds don't stay one-liners. They collect evidence over weeks or months, like quotes, timely news, pods, articles, links to book notes, and my own stories. Some of the topics you've read this year sat in there for six months, getting heavier, before I wrote a word. Patience isn't just a virtue. It's a production method. |
2. The research agents.
A Mac Mini in my office runs research agents. They scan Reddit communities where people like you ask real questions, they review LinkedIn articles, check whether anyone is actually searching for those topics, and rank what's worth my attention. The best of those topics also land in the Notion inbox. They can add to an existing seed or create a new one. One agent runs on Claude and one on Grok, and I grade them both like interns. I typically triage Sunday evening and throw out weak inbox entries. |
3. The writing partner: Claude.
This is the part people ask about. Claude is connected directly to my Notion databases and to Beehiiv, where this newsletter lives. It can read my seeds and the supporting material, read three years of past issues, connect ideas I’ve overlooked and even draft inside the Beehiiv editor. |
What it can't do is decide what's worth saying. That part's still mine. I made that argument back in Human-generated content, and I believe it even more now. |
4. The distribution.
Tuesday morning, Beehiiv lands these in your inbox, then a Mac Mini agent turns the issue into a few LinkedIn posts. I haven’t automated that part yet, so I edit then paste a couple of those into LinkedIn most weeks. I eat my own dog food. |
Why it took three years |
I didn't start this way. For most of three years I wrote every issue by hand, because consistency beats talent. My old Notion swipe file was a collection of topics and links but not nearly the inter-connected ideas that’s bloomed as I added old Evernote files over the past 6 months. Three things had to be true before AI became truly helpful: |
An archive to point it at. 158 issues is what teaches it my voice. Without them, the output is generic. A pipeline with real material in it. A seed that says "write about judgment" produces nothing useful. A seed with six sources, two stories and a counterargument produces a draft worth editing. Earned trust. I didn't assume the output was good. I checked it, week after week, until I knew where it's strong and where it needs me.
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Someone starting cold with the same tools gets bland output and decides AI doesn't work. They're half right. My own experiments showed me the same thing in 2024. The tool was never the asset. The body of work you point it at is. |
And that's the good news if you're sitting on 25 or 30 years of experience. You've already made the deposit. Your uncommon knowledge just needs to be written down somewhere a machine can reach. |
Help me build year 4 |
Year 4 should be built more around what you want, not just research topics in my Notion files. When you've asked before, I've listened. |
Take the poll below. It's one click. And if you want to say more, comment below or hit reply. I read every one, and last week's replies about AI experiments are already in the pipeline. |
Thank you for three years of your attention. Especially those of you who've been here since Hello World. |
I am grateful for the opportunity to keep writing my own permission slip! |
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Now go launch something 🚀 |
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What should year 4 of The Launch Key do more of? |
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The best time to plant a tree was 20 years ago. The second best time is now. |
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For product teams moving at AI speed. |
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AI makes it easier to ship anything, even bad ideas. The hard part is knowing which ideas are worth building. |
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Capture ideas, prioritize with evidence, and build living roadmaps your team can rally around—all while staying connected to delivery in Jira, so everyone can see what’s being built and why. |
Better product decisions in the AI era. |
Try Jira Product Discovery |
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Old School Wisdom |
You're not 25 with nothing to lose. You have decades of experience, a reputation, and a voice in your head asking if you've missed your window. |
The data says you haven't. |
This data-backed field guide pulls from MIT and U.S. Census Bureau research on 2.7 million startup founders — proving that the average founder behind the most successful companies was 45, not 25. A 50-year-old entrepreneur is twice as likely to build something massive. A 60-year-old? Three times as likely. |
Inside, you'll find the stories behind that data: Ray Kroc at 52. Bernie Marcus at 50, right after getting fired. Arianna Huffington at 54. Morris Chang at 55. Real founders who built category-defining companies after the age most "startup advice" tells you to give up. |
You're Not Too Late |
A Field Guide for your Second Act |
Launch Key | The Newsletter for Late-Career Entrepreneurs • Launch Key newsletter |
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Modern Tools |
I’ve used many email platforms over the past few decades, including both enterprise and individual solutions. I never really loved any of them, until Beehiiv 🐝. |
If your business will send newsletters, I can’t recommend it strongly enough. |
They’ve made it drag-and-drop easy and free to start They have built-in design tools They have a very good recommendation engine for other newsletters Their Advertiser network is robust and growing
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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. |
Ready to get started? |
Click on the link below to save 20% off your first 3 months of a paid plan after a complimentary 30-day trial. |
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Recommendations |
📕 MGMT Playbook : Practical management insights straight to your inbox every Wednesday. |
🚏 The Cautionary : Learn to challenge conventional wisdom. |
🏢 Retirepreneur : Your guide to turning decades of experience into profitable consulting, coaching, or course businesses, without risking your retirement security. |
🗃️ Dealroom Business Success Uncovered : Learn directly from billionaire entrepreneurs on how to grow a business. Join a community of 2,000+ innovators. |
🧾 Redefining Retirement : Too Young to Retire, Too Old To Take Orders? Yeah, Me Too. |
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Visual Crapshoot |
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Launch Key readers – Thank you for your support as we celebrate 3 years 🎆! 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. |
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| ~ Rob |
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