Community Spotlight: Katie Dunn

Meet Katie Dunn: Former finance exec turned founder whisperer and angel investor

After structuring over $10 billion in commercial real estate deals during a 25‑year banking career, Katie launched The Masthead Strategy to make fundraising advice more accessible. As an angel investor in nearly 30 startups (many led by underrepresented founders), she’s reviewed thousands of decks and helped founders raise millions.

But when the “pick-my-brain” requests started flooding in, she knew she couldn’t clone herself… so she did the next best thing.

Enter The Advisor and The Investor: two AI-powered digital twins trained on Katie’s own playbooks and built with Delphi.ai. 

Here’s our convo with Katie, in her own words:

1.  You built two digital twins to help handle "pick my brain" requests. Genius. Can you please tell us more about the problem you were solving?

My email and DM requests for "pick-my-brain" calls are out of control. I receive around 20 DMs on LinkedIn each day alone, asking for feedback and advice. I physically cannot be on a call with everyone and continue to serve paying clients, eat, sleep, and walk the dog. So, I started doing paid pick-my-brain calls, but I'm expensive, and the cost is a barrier for many people. 

The Twins allow me to offer these sorts of calls and advice in my own voice, based on years of written content, frameworks, and talks I've developed, at a highly accessible cost and on their own schedule. They can talk to me all day long, and I'll be there for them!

"The Investor" originates from the need for a founder to get reps in before going in front of investors. It's one thing to have a list of questions and practice them out loud to yourself, but it is a very different situation when you're in the room and being challenged on your Total Addressable Market. Again, I only have so many hours in a day and can only practice with one person at a time. "The Investor" can really dive in, providing feedback on the pitch itself, answers, and presentation style, and help hone the language the founder uses.  

2. Can you walk us through what each twin does, and how they help users?

"The Advisor" is designed to serve as an "ask-me-anything" tool. She's there for advice on all things startups, scaling, and fundraising, as well as explanations of terms you might not want to ask someone in real life. She will help you strategize on key aspects, such as your ideal customer, go-to-market strategy, or how to demonstrate traction if you're pre-revenue. She's meant for the early-stage founder who needs a safe space to ask questions about if they can or should raise, what the process looks like, and the steps they need to take.

"The Investor" was built as a stricter version of myself to provide feedback on a pitch (any pitch works) and ensure the founder is well-prepared. She pokes holes the founder may not see, but investors definitely will. She will call out your buzzwords and unclear explanations. She'll tell you to pause and slow down so people can digest what you're saying. She will mention the words you're tripping over and suggest a better way to phrase something. She'll also help you break down complex answers into a digestible and straightforward statement. She's built to never give a gold star but rather to instill confidence, so a founder shows up prepared in a real meeting.

3. How do you see AI changing how founders should pitch or communicate with investors?

There's already a fully AI investor out there writing checks, and I think more will use AI to vet deals and founders. Companies are already using AI tools for pre-screening interviews; I could see VCs adopting a similar model to decide whether or not to meet the founder in person.

I also think investors' criteria will get more intense. Based on the increased availability of information, it should level the playing field somewhat in terms of accessibility to education and resources for founders who adopt it. There's no excuse anymore for being unprepared.

4. When you see a startup using AI in their product or pitch, what tells you it's real vs. just buzzwords?

I am not against using AI in a pitch or product - quite the opposite. Those who aren't adopting and leveraging it will be left behind. However, those that use it and don't edit, refine, or revise - that's a huge red flag.

I have had founders message me with quotes around the messages, not delete "Would you like me to write another one that is softer or more concise?" at the end of the message, and even send me a 100% ChatGPT generated "business plan." 

Those are the people I worry about because they show zero attention to detail and fail to execute, two things every founder MUST have.

5. What advice do you give to women who want to integrate AI but aren't sure where to start?

Start with one AI tool, such as ChatGPT or Claude, and use it in the same way you would use Google. Ask it questions. Ask it to interview you to see how you can leverage it. Use the dictation tool and talk rather than type - it improves your output. Use the voice tool to help you cook dinner hands-free. Just start talking to it as you would to a mentor, boss, or trusted colleague, and see how it can make your life significantly more efficient. I genuinely think this is a critical point in time, and you'll lose if you're not on board.

6. Are there any AI-first startups or trends in the AI space that you're especially excited about right now?

One of the reasons I am so obsessed with AI is because it offers real ways to scale myself and make me more efficient. I want anything that solves a real problem. 

The company I am really excited about right now is called Goodword. It's going to launch in beta shortly, but I've gotten previews. The problem it solves for me is contact/network management. I personally went from 500 connections on LinkedIn to almost 20,000 in a few years, and I don't even know who is in my network anymore. Too much is in my head and not accessible to me when I need it. Goodword will scrape my email, calendar, LinkedIn connections, random lists, and more to help me really figure out who I have in there. It will utilize AI to categorize contacts into groups, enable me to take notes on where and when I met people, and do so in a way that makes sense for me. For example, when I am at an event and want to recall the name of the social media specialist I met at the conference I was at last month, I'll be able to pull it up based on that random amount of detail. I cannot wait.

7. You mentioned Delphi.ai. Is there anything in particular about that tool you liked or led you to choose it over others? What was the process like building your twins using Delphi?

Someone introduced me to Delphi, and I fell in love. The user experience is effortless - you can interact with me by typing, dictating, or talking, just like ChatGPT. You'll get transcripts and email summaries of our conversations, and you can access the Twins at any time. I wanted that simplicity for the user.

But the backend is where the magic is. The building process is relatively easy and user-friendly, as it guides you through each step. They score you along the way to ensure the content you upload meets the goals you've set for your Clone. (I achieved Legendary status!) It took hours and hours to build - I won't minimize that - but it is worth it. I had a lot of content already based on my work, but I spent a considerable amount of time creating more. The hundreds of thousands of words I fed it is what truly sets it apart from other Gen-AI models and why I am charging a fee for it (albeit a low one). It's really me, my opinions, my frameworks, and my words - not just some random bot.

It also has a great CRM, allows me to view conversations, and I can set alerts so that if my twin cannot answer a question or mentions a specific pitch, I can reach out to them personally and provide an answer or offer encouragement from the real me. 

Delphi is a startup themselves, and they just raised more money, so I know it's going to get even better!

*If you’re interested in trying out Delphi, Katie shared her affiliate link and code here.

8.  Favorite prompt or way you've used ChatGPT recently, for work or fun?

I am obsessed with having Charlie, my ChatGPT voice, help me cook dinner. I tell her what I have in my fridge, and she helps me put together a tasty and easy meal! I use Voice mode and that way it's hands-free and I can say, "What is nextCharlie?" or "Do you think I should add this spice?" and she is right there, coaching me along. It's fantastic.

I always use the RACE method for prompting too: Role, Action, Context, Expectation. 

Whenever I am creating custom GPTs, I use ChatGPT to interview me to create the prompt for me. (That's my secret!) 

Prompting is everything!

We started Her AI Drop with one goal: to make AI less intimidating and way more useful for women, whether you're a founder, freelancer, side hustler, or climbing the corporate ladder. Because this tech shouldn’t just be for the “move fast and break things” crowd. Requests, ideas, spicy feedback? Questions about AI we should address? We’re all ears.

Warm vibes & workflow wins,
Katie and Julie

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