Hey Reader,

This week I'm sharing some practical AI tips straight from a presentation I just gave at a mastermind I was at this week. These aren't hypothetical "someday" tools — they're the actual systems that have helped me increase profit margins by nearly 4x while running BestSelf within strict daycare hours.

In this newsletter, you'll discover:

• How I documented 7+ years of company knowledge without in hours not days

• Exact process to streamline your newsletter by 80% (with 62%+ open rates)

• A voice tool that's helped me write 200,000+ words in just three weeks
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How I'm Preserving Company Knowledge (Without Losing My Mind)

When I bought back BestSelf, I faced a unique challenge:

• My original team was gone
• I had limited working hours (9AM-4:30PM daycare hours)
• Years of product decisions and internal knowledge lived only in my head

What made this especially challenging? I discovered our company Notion docs had been deleted when the previous account was closed and never properly transferred. With a previously tenured team (the shortest tenure being 2 years, the longest 7 years!), there was always someone to ask about why we did things a certain way.

Somehow I needed to simultaneously hire new people while creating systems to handle the constant flood of questions about products and processes at the same time as ensuring everything continued to run and serve customers.

I realized I needed a way to extract the knowledge from my head without spending hours at a computer. My solution? Have AI interview me while I was walking or doing laundry.

Instead of sitting at a computer for hours typing everything out, I posed the challenge I faced and then had it:

1. Generate interview questions about our company history, product info, stories decisions, and processes.
2. Recorded voice memos answering these questions while doing mindless tasks
3. Dumped transcriptions into ChatGPT to start creating a knowledge base
4. Had ChatGPT create any followup questions based on my transcriptions
5. From there I created a GPT with the docs that can be queried against

The result? New team members can now understand years of context in a fraction of the time. Plus, I preserved critical institutional knowledge without it taking over my life or my day.

If you're building something, start documenting early. If I could go back in time, I'd have been voice-memoing business decisions from day one.

Pro tip: You don't need fancy software for this — just the 'Voice memo' app on iPhone which now automatically creates transcripts. dump into ChatGPT and have it organize it for you.

How We Cut Newsletter Creation Time by 80%

When I bought back BestSelf, I knew a high-value newsletter would be crucial. But as a solo founder rebuilding a business, writing quality content weekly felt overwhelming.

Our "Winning Wednesday" newsletter now achieves:

• Average open rate of 62.7% to a list of 82,000+ subscribers
• Peak open rates of 76-79% for our best issues
• Creation time cut from 4-6 hours to just 45 minutes

The secret? I created a system using Claude and Lex.page that maintains my voice while dramatically cutting production time.

​Here’s the whole process soup-to-nuts (prompts and process included):​

Key insight: The most valuable part of this process isn't just time saved — it's that I no longer dread writing the newsletter. What was once a burden is now one of my favorite marketing activities because the AI handles the parts I find tedious while I focus on the strategic thinking. I'm also a month ahead of publishing schedule!

New Tool Alert (I'm in Love 🥰)

My new obsession tool is Wispr Flow — in just 4 weeks, I've dictated over 220,000 words. I use it for brainstorming, coding, writing, slack messages. This tool lets me speak naturally while it transcribes in real-time and inserts the text wherever my cursor is.

More AI Experiments I'm Testing:

1. Voice Cloning for Audio Content

I cloned my voice using ElevenLabs. Why? Partly curiosity, partly practicality.

As a founder/CEO trying to limit have more work/life balance this time around, time is my ultimate bottleneck. I should theoretically focus only on high-leverage activities, but I genuinely love experimenting with new tech.

I wanted to see if we could create founder-led content without me personally recording hours of audio. (I'll update you on the results in a future newsletter!)

2. Audio Learning for Team Onboarding

When onboarding new team members last month, I discovered some were struggling with our dense product documentation. I wondered: could we make this information more digestible?

I decided to experiment with a new approach:

• Uploaded all our product overviews to Google NotebookLM​
• Asked it to create a conversational "podcast-style" walkthrough of each product
• Shared the audio files with the team as an optional learning resource

Is it a professionally produced podcast? No. But is it significantly more engaging than reading through technical documentation? Absolutely.

One team member told me they "binged" all our product info while cooking dinner 😁

3. The "Brutal Advisor" Prompt

This prompt is insanely valuable if you use ChatGPT as regularly as I do.

Think about this - we used to say Google knows you better than anyone because you'll search for things you'd never admit publicly. Well, if you're using AI extensively like I am, it eventually knows your patterns, blind spots, and tendencies better than anyone.

I've done coaching, therapy, and worked with mentors, but some of the insights I get from AI with prompts like this one below are genuinely mind-blowing. It can cut through your own self-deception in ways that are both uncomfortable and incredibly valuable.

When you need tough love and strategic clarity, this prompt is gold:

An Unexpected Benefit of Sharing Online

I started sharing online back in 2012, so it's been 13 years of writing, tweeting, and documenting experiments and business ideas.

What's happened over that time is magical: I've built genuine relationships with people I admire, and now in Austin, many of my closest friends are people you'd recognize from their own online sharing.

There's a compounding effect to this sharing habit:

1. You learn more deeply. When you teach or write about something, you have to understand it at a different level. Explaining concepts clearly requires truly grasping them first.
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2. You attract your people. Case in point, a few months back, a mechanical engineer from NASA responded to one of my newsletters. She happened to be in Austin for a 3D printing conference, so we met for coffee and had a great conversations. Then last month I texted her about 3D printer options and she gave me expert advice. Now I've been 3D printing prototypes for a new product and also doing cool experiments with my daughter.

If you're not sharing your journey yet, start with the beginner mindset. Your "day one" content should be awkward—that means you're growing! What seems basic to you might be revolutionary to someone else.

I'm trying to practice this myself by documenting what I'm learning about coding and how I'm using AI for specific, practical business cases in these newsletters. The connections and opportunities that come from putting yourself out there are worth every uncomfortable moment.

Have a great week Reader!

Cathryn

P.S. What AI tool are you loving right now (like WisprFlow) that I should know about? Hit reply and let me know - I'm always looking for new tools to experiment with!

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