Hey Reader,

This week I'm sharing two important updates: how we're using AI to transform BestSelf (with real examples), and some crucial year-end tax strategies for entrepreneurs. Let's dive in!

How We're Actually Using AI (No Fluff!) 🤖

One of the biggest game-changers has been creating custom GPTs for specific tasks. Think of it like building a super-smart assistant that knows everything about your business. For example:

• Product Knowledge GPT:​
  Loaded with all our product details, specs, and common questions. Now our customer support team can get instant, accurate answers.
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• Ad-Machine GPT:​
  Trained on our best-performing ads and copywriting principles to help generate and optimize ad content across platforms.
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• Company History GPT:
  ​As we approach our 10-year anniversary (wild!), I realized I needed a way to preserve our institutional knowledge. I spent a week having AI "interview" me about everything from product decisions to internal challenges we've faced. Now we have a comprehensive document loaded into a GPT that anyone can query about why we made certain decisions or stopped specific initiatives. No more bottlenecks where I have to explain historical context!

Real-World AI Applications 🔍

Here's how we're using AI in practical, day-to-day operations:

1. Customer Feedback Analysis:
   We used AI to sift through product reviews and identify patterns. This led to a major quality improvement – we discovered consistent feedback about paper quality in our journals (something I personally agreed with). Result? We've moved back to our original supplier to restore the quality our customers loved.
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2. Marketing Optimization:
   Creative ideation: We've been testing a TON more creative than we used to for ads which requires more effort and energy on hooks, angles, ideas etc. We’ll use Foreplay to find ads we like and use AI to help us adapt the ad for our product and create a brief for us and go from there.
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   AI helps us extract "golden nugget" reviews for ad copy, making our marketing more authentic and resonant with potential customers.
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3. Institutional Knowledge:
   Remember playing the game "20 Questions"? I basically did that with AI about our company history. It helped me document everything from product evolution to why we made certain strategic pivots.​​
   Now anyone on the team can understand the context behind our decisions without playing phone tag with me.
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Rebuilding Customer Relationships Differently 💌

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Here's something interesting: When I looked at our email strategy, I started thinking about how ecommerce treats email lists like a bank account. Most brands spend Q4 making constant withdrawals, burning through their lists to convert subscriber goodwill into holiday dollars.

But here's the thing – you can't keep making withdrawals without deposits. At least not in any bank I know about (unfortunately 😆).
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Coming back post-sale our email list was pretty burned and stagnant. I knew we needed to start making serious deposits of value now, building up goodwill with our audience before Q4. Think of it like saving up for a big purchase – the more you deposit early, the more you have to work with when you need it.

So I'm trying something different:

Our new weekly 'Deposit' email

We used to send a weekly action-packed email on Monday that had fallen by the wayside. Rather than starting the old one back, I set up a new one going out on Wednesdays (easier to get eyeballs on inboxes than Mondays).

A new initiative where we send value-packed emails with no selling. Just pure, actionable content to help our community win, same structure for each week. We call it 'Winning Wednesday' and here's general structure:

1. Subject Line: [Winning Wednesday] + Hook
2. Story Opening: Brief personal anecdote to introduce a theme
3. Main Teaching: One core lesson with actionable steps
4. Wednesday Challenge: Single, easy task to do today
   • Must be quick and simple
   • Clear benefit
5. Reflection Question: One thought-provoking prompt
6. Quick Picks:
   • 📚 Reading Corner: One book and/or video
   • 🔍 Cool Find: One useful tool/resource
7. Sign-off:
   • Friendly close
   • P.S. with call to action

The key is consistency. Same format every week, focusing on value over selling. Each section is brief and scannable, designed to be read and acted on quickly. If you want to see it live you can sign up and see it here.​

I built a GPT to help me with this so each week it takes me less and less time.

Personal Connection: I'm sending emails from my own email and actually responding to replies when they come in, spending 5-10 minutes in between other tasks.

What's Working (and What's Not) 🎯

Being honest – like I mentioned in my last email, coming back to the business was like walking into a house on fire. There were urgent issues everywhere, and I've had to relearn a lot. But these AI tools have been game-changers in helping me put out the fires and rebuild systematically.

What's Next? 🚀

Since many of you have asked about the nitty-gritty details of creating custom GPTs, I'm working on an in-depth blog post that will walk you through my entire process. I'll share it on littlemight.com soon – keep an eye out!

In the meantime, I'd love to hear from you:

Would love to hear your thoughts! Have you tried using custom GPTs in your business? What's working for you?

Smart Money Moves for Year-End 💰

With year-end approaching, here are some tax-saving strategies I'm using (and you should consider too).

Quick note: This is US-focused, but the principles might be useful wherever you are!

HSA: Your Secret Tax-Free Investment Account 🏦

If you have a high-deductible health plan, you should absolutely be maximizing your HSA. Here's why:

• It's like a stealth investment account where money grows tax-free and you can use on way more than you think.
• If you can afford to pay out of pocket then you can invest the money while building up a stack of "IOUs" for future use
• Pay for qualified expenses now, keep the receipts, and reimburse yourself later while letting your money grow

Pro tip: I use Lively to manage my HSA and track receipts. Here are some surprising things you can use HSA funds for:

• Regular medical, visits and qualified supplements
• Health tech (like my new Oura Ring for sleep tracking)
• Alternative therapies (including sauna treatments)
• Functional medicine visits
• Mental health services

Check out TrueMed for more details on this which I was able to use to get my monthly Tonal subscription paid for through our HSA.

The key is: to pay upfront, save the receipt, and let that money grow tax-free until you need it. I started this account in 2022, and have put in ~23k in total deposits but it's now grown to $36,000 through investing in the market.

Here's a real example: I've accumulated $24k in reimbursable expenses since 2022 – mostly for things I would have bought anyway (like my Oura ring). By paying out of pocket and keeping my HSA invested, I'm essentially creating a tax-free investment account while covering my health expenses.

Solo 401(k): The Self-Employed Superhero 💪

If you're self-employed, here's a massive opportunity: you can put up to $69,000 into a Solo 401(k) per year. Here's how it breaks down:

• Your business contributes as the employer (up to $46,000)
• You contribute as an employee (up to $23,000)
• Can potentially do this for both you and your spouse

Important: This needs to be set up before December 31st! I use Carry to handle all this for me. Yes, you'll deal with some payroll taxes, but the tax savings can be substantial. Disclaimer I’m a tiny investor in Carry from their seed round but only sharing now that I actually use and love the product personally.

Quick Life Updates 📸

• My daughter is in her Frozen era (so cute 🥰)
• Celebrated my friend Codie's book Mainstreet Millionaire launch. I brought my mum with me and she had the best time.

We did Virtual Reality Squid games event for my birthday and it was so fun, high recommend!

• Here’s the Appsumo video I did that I forgot to link in the last newsletter
• Here's the YouTube video from my appearance on The Nathan Barry Show talking about buyouts, embezzlements and other fun stuff

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See you next year, Reader!

Thanks for reading,
Cathryn

P.S. If you found this helpful, would you do me a quick favor and forward it to one entrepreneur friend? Or have them subscribe here.

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2028 E Ben White Blvd #240-5675, Austin, Texas 78741
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