AMA: Your top AI questions, answered.

Today, I’m tackling YOUR top AI questions!

• What AI subscriptions do you actually PAY for vs. use for free? Should I pick one or use an all-in-one solution?
• What’s the best way to implement AI without disrupting my business?
• How do I get my team to embrace AI — especially less tech-savvy members?
• How can AI help triage / respond to lots of emails?
• What’s the fastest way to master AI?
• What are the biggest AI mistakes business owners are making?
• Can I "AI-proof" my career?
• How can I avoid being replaced by AI?
• How do you get ChatGPT to write like you?
• What’s your advice for founders/CEOs trying to figure out AI right now?

To see yours answered in our next Q&A edition, submit it anonymously here.‍

Let’s get into it.

1. What AI subscriptions do you actually PAY for vs. use for free? Should I pick one or use an all-in-one solution?

As for the large frontier models, I personally pay for:

• ChatGPT (Plus account, $20/month)
• Gemini (included in Google Workspace Business account, now $14/month)

Too many people worry about which AI tools to use, rather than focusing on how to use them effectively. You don’t need a massive stack of AI tools — you can use the these large models for a LOT, and then fill in the gaps with specialized tools for specific use cases.

(You can see my full AI tech stack here.)

Another great option? All-in-one solutions like BoodleBox, which offers:

• Multi-model access: Choose the best model for the task or even combine multiple models.
• Saved knowledge: Upload important files for easy reference in chat threads. (Think: Brand style guides, product documents, buyer persona profiles, etc.)
• Collaboration features: Share AI-powered chat threads and collaborate with teammates in real time.

I like some of the native features that ChatGPT offers (like custom GPTs and Projects). But if you find you're not really taking advantage of those features, switching to an all-in-one solution can streamline costs, simplify your tech stack, and give you access to different features that might better suit your business.

2. What’s the best way to implement AI without disrupting my business?

Focus on work, not tools, and start smaller than you think.

AI adoption doesn’t have to be overwhelming. The key is to integrate AI where it naturally fits into your workflow, rather than forcing drastic changes. Many businesses get caught up in testing multiple AI tools, only to find they don’t have a clear strategy for implementation.

Instead of searching for the perfect tool, start with one well-selected use case that aligns with your existing processes. Choose a repeatable and scalable task — something your team does regularly — that AI can streamline. This could be automating meeting summaries, optimizing customer support responses, or drafting internal reports.

By focusing on practical, high-value applications, AI becomes a productivity booster rather than a disruption. Small, incremental wins will build momentum and ensure smoother adoption, allowing you to expand AI use in a way that enhances — not interrupts — your business.

3. How do I get my team to embrace AI — especially less tech-savvy members?

It doesn't matter if it's Facebook in 2010 or HubSpot in 2015 or ChatGPT in 2025... Adopting new technology company-wide is hard. The keys? Education, communication, and persistence.

After years of guiding companies through digital transformation, here’s what works:

• Address fears and misconceptions: Many people fear AI will replace them. Communicate openly and honestly about the role you see AI playing in your organization — for example, to augment human skills or to automate mundane work — to assuage your team's concerns.  
• Make them care: People resist change when they don’t see the value. Show them how AI can save them time, reduce tedious tasks, and even make their jobs more fulfilling.
• Normalize AI use: Encourage small, low-risk AI experiments. Start with a single process where AI can provide immediate, tangible benefits. And create a culture where using AI is seen as a skillset — not a shortcut.
• Make it easy: Provide structured training, clear documentation, and support. Don’t assume they’ll figure it out — walk them through practical applications relevant to their roles.
• Lead by example: If leadership actively integrates AI into their own work, it signals to the team that it’s not just a passing trend — it’s a shift worth embracing.

Resistance isn’t about AI — it’s about uncertainty. Reduce friction, build confidence, and adoption will follow.

4. How can AI help triage / respond to lots of emails?

This depends on whether you're managing an individual’s inbox or a team’s. For teams, having a shared AI-powered knowledge base can streamline workflows.

NotebookLM (and NotebookLM Plus, now included in Google Workspace Business accounts) allows you to generate responses based on your hand-selected sources, reducing hallucination risks and controlling quality. Use it as a single source of truth that you can query to find information fast. (For example: Customer service requests, product details, marketing content.)  

5. What’s the best way to learn AI (without wasting time)?

It’s ironic, isn’t it? AI exists to help us work smarter, yet keeping up with AI feels like a part-time job.

I strongly recommend that everyone develop a baseline understanding of AI, with a particular emphasis on generative AI and large language models. This foundational knowledge will help individual contributors to effectively use AI in their work and is absolutely essential for managers and executives who are responsible for making strategic decisions around AI.

Starting with a structured, high-quality training provides the benefits of any good education: It’s a shortcut, allowing you to learn from someone else’s research and experience so you can avoid common mistakes and build a solid foundation, fast.

After you've done that, the challenge is filtering what’s truly valuable from the overwhelming flood of AI news, tools, and opinions. Avoid trying to follow every update or test every tool. Instead, focus on information that aligns with your specific needs and goals. And be ruthlessly selective about your sources.

My criteria for trusted AI sources:

• Credibility: Real-world AI expertise (not just theory). Look for practitioners who are actively using AI, not just talking about it.
• Relevance: Practical advice that translates to real-world action.
• Insight: Nuanced, hype-free analysis that helps to separate signal from noise.
• Originality: Unique perspectives, not just repeating headlines.

Most importantly, apply AI instead of just learning about it. Experiment, refine, and integrate AI into your workflow — experience is the best teacher.

6. What are the biggest AI mistakes business owners are making?

There are a few...

• Getting distracted by new tools, instead of mastering the ones they have (Shiny Object Syndrome).
• Ruthlessly prioritizing efficiency gains, instead of quality gains (Commodity Trap).
• Getting caught up in the AI news cycle, instead of practical application (Inside Baseball).

But I think the most common mistake business owners are making today is simply hesitation — continually learning and never experimenting (Paralysis by Analysis).

If AI isn’t saving you time yet, you don’t have an information problem—you have an application problem.

You can solve for risk (AI Alignment Matrix, our 3S framework), you can solve for hallucination (Human in the Loop, our Good-Better-Best model), you can solve for, refine, and improve a lot of things. But you can’t improve nothing.

Stop overthinking and start using it.

7. Can I "AI-proof" my career?

I don't know if any job is 100% AI-proof, but you can make yourself AI-resilient by taking proactive steps to future-proof your role and skill set.

• Invest in AI literacy: Understand the fundamentals of AI, how it works, and how it is being applied in your industry. The more you know, the better equipped you'll be to leverage AI effectively.
• Develop deep domain expertise: Your ability to apply knowledge in nuanced, real-world situations is what sets you apart. Build a unique perspective that AI alone cannot replicate.
• Master complementary skills: Work on uniquely human qualities like emotional intelligence and leadership.
• Be adaptable and open to change: The only certainty is that AI will continue evolving. Those who embrace new technology and continuously learn will have an edge over those who resist it.

Those who thrive likely won't be those who resist AI or those who rely on it entirely — instead, it will be those who understand how to blend human expertise with AI's capabilities to achieve outcomes that neither could accomplish alone.

8. How can I avoid being replaced by AI?

Similar to the last question, it's important for both individuals and companies to think about the unique value that they offer that can't be replicated by AI.

This is especially crucial because as the same core models begin 'powering' more workforces, increasing sameness becomes a logical conclusion.

However, this presents an opportunity: When AI makes it easy for anyone to create, the real competitive advantage isn't just producing more — it's producing more of what makes you uniquely valuable.

That means:

• Scale your unique expertise: Don’t just automate routine tasks — do more of what makes you different.
• Invest in original thought: Stand out by offering unique perspectives and personal experience.
• Focus on high-value work: AI does the grunt work; you refine and elevate it.

Businesses that blend AI efficiency with human expertise will have the best chance to thrive. The rest will look, sound, and be like everyone else.

9. How do you get ChatGPT to write like you?

I’ve used a few strategies to get AI to write more like me (or a client/brand), including:

1. Examples
2. Insight

Examples: Few-shot prompting is a proven technique to get better results from LLMs, and this includes writing.

By giving ChatGPT more examples of your writing — and better yet the kind of writing that you're asking it to perform (your emails are probably different than your articles are probably different from your LinkedIn posts or your public speaking) — the more effective it will be at mirroring your structure, tone, and style.

Insight: Context and unique perspectives are critical to more authentic and original content. For example, instead of just saying, “Write an article on AI differentiation,” I might add: "Provide 3-5 thoughtful questions to ensure you deeply understand my perspective before drafting."

Then, I answer them via voice dictation. This keeps the output nuanced, authentic, and uniquely mine.

10. What’s your advice for founders/CEOs trying to figure out AI right now?

You built your business because you had a vision — because you believed in what you do.

But now, your success depends on you. Your knowledge is locked in your head. Scaling means working more, not less.

You wanted freedom, impact, and growth — but instead, you’re stuck doing everything yourself.

If that’s you, here’s my advice: Don’t just using AI for productivity; use it for leverage:

• Systematize your expertise so your knowledge doesn’t depend solely on you.
• Scale the unique value you bring to your business so you can grow your business, without adding more hours to your week.
• Automate low-value tasks so you can focus on high-impact decisions.

If you feel like the bottleneck in your business, you have a massive opportunity to transform your company (and your life) with AI.

That’s it for this edition! Want your question answered next time? Submit it anonymously here.