𝗢𝘂𝗿 𝗚𝘂𝗲𝘀𝘁:

𝗞𝗮𝘁𝗶𝗲 𝗗𝘂𝗻𝗻 (𝘀𝗵𝗲/𝗵𝗲𝗿) is an angel investor and startup advisor who has financed $10B+ in commercial real estate and invested in nearly 30 early-stage companies. Through Masthead Strategies, she helps underrepresented founders sharpen their pitch, tell a clearer fundraising story, and walk into investor conversations prepared. Katie serves on the boards of Outcast Brands, Fierce Foundry, and the Enthuse Foundation—and she’s also the person to talk to if you want a candid take on Digital Twins.

𝗘𝗽𝗶𝘀𝗼𝗱𝗲 𝗢𝘃𝗲𝗿𝘃𝗶𝗲𝘄:

Fundraising often goes sideways for simple reasons: the story is hard to follow, the “why now” is fuzzy, or the ask doesn’t match the stage of the company. In this episode, Anne Murphy and Kyle Shannon sit down with Katie Dunn to break down what strong pitches have in common, what makes investors lean in, and how founders can prepare for diligence before it becomes a scramble. They also get into one of Katie’s favorite topics—𝗗𝗶𝗴𝗶𝘁𝗮𝗹 𝗧𝘄𝗶𝗻𝘀—and how that way of thinking can change how you talk about proof, performance, and trust.

𝗪𝗵𝗮𝘁 𝗬𝗼𝘂’𝗹𝗹 𝗟𝗲𝗮𝗿𝗻:

• The first 2–3 minutes of a pitch: what matters most (and what can wait)

• How to define traction in a way that fits your stage

• The questions that signal real interest vs. polite curiosity

• Common red flags founders can fix early

• Why Digital Twins keep coming up—and what founders should consider as they build

𝗟𝗜𝗞𝗘, 𝗦𝗛𝗔𝗥𝗘, 𝗦𝗨𝗕𝗦𝗖𝗥𝗜𝗕𝗘:

Catch a new episode of The AI Readiness Project every Wednesday at 3pm (PST), co-hosted by Anne Murphy of She Leads AI and Kyle Shannon of The AI Salon. Want to meet others navigating this new terrain with humor and humanity? Visit The AI Salon or She Leads AI to find your people.

Raising Capital with Clarity_ Katie Dunn on Pitching_ Investor Conversations_ and Digital Twins

Kyle Shannon: Ann Murphy,

Anne Murphy: how did we manage to get two bops in a row with our intro song? You know,

Kyle Shannon: we got, we've got the magic, we've got the magic touch. I don't know.

Anne Murphy: You know, and also the intro, um, the language is so good and you and I like, we kind of. We're like met a little bit when we picked it. When we chose it.

Kyle Shannon: Yeah. Yeah. It's good. It works. Yeah. It was probably Frankenstein together with some things. Yeah. But, but it was good. I particularly liked the part about, you know, focusing on what makes us human. That's been my, my, uh, my, my big revelation that's been evolving over the past three or four months is, is this idea that, you know, it's all about us.

It's all about humans and who we are, what we believe, what our values are, and then, you know, using AI to augment that and, um. Sometimes not using AI to augment,

Anne Murphy: sometimes not using ai,

Kyle Shannon: right?

Anne Murphy: Yep.

Kyle Shannon: Sometimes not using ai. Sometimes you use it, sometimes you don't. How have you been? What's, tell, tell me what's going on with you?

What's going on in, in, in She Leads, what are, what are you excited about these days and,

And, and it needed to, like, it had to, that was the trajectory. But it's so satisfying to like, meet all those goals and, and it's not just about like the KPIs, but it also is Yeah. Because in order to make it happen, you have to, you know, you gotta have certain, you know, baseline. But I didn't even notice it as it was happening because it was just like, people organically getting what they need.

Yeah. Yeah. And I'm making the right offer. And so I am, as we decide more about what we can pour gas into and what we don't have to do,

Kyle Shannon: and

Kyle Shannon: That's great. That's great.

Anne Murphy: Yeah. So

Kyle Shannon: I'm

Anne Murphy: really happy.

Kyle Shannon: What are you seeing? Are, are you not, is there, is there a different kind of person showing up or is, is how people showing up changing, like, you know, do, do you find you're getting beginners?

Um, what's, what's the nature of the, the folks that, that are. Joining these days.

Anne Murphy: Definitely a seriousness, a new level. Yeah. Of seriousness. Think.

Kyle Shannon: Yeah.

Anne Murphy: Think about Moji. So Moji, um, uh, her first big exposure to AI was when we did our virtual version of the Create conference.

music: Mm-hmm.

Anne Murphy: And she was asking questions like, oh, is this a career?

And, oh, how can I, you know, do a side hustle? What's the best

music: comp?

Kyle Shannon: Yeah, yeah, yeah.

Anne Murphy: Just like, you know, gimme the opportunity and I'll do it.

That kind of thing.

Kyle Shannon: Mm-hmm.

Kyle Shannon: yeah. I, I, that feels right.

And in fact, there's a brand new feature from Claude that just came out called Cowork.

Anne Murphy: Yeah.

Kyle Shannon: That was 100% written by Claude. 4.5 Opus. Was, and

Anne Murphy: you have a Mac. So have you used it yet?

Kyle Shannon: I haven't. 'cause I don't, I'm not you, you have to be a Max subscriber. So that's their 200 bucks a month. Oh. I can only afford 17 $200 a month subscription.

So the, I know one was just, was too much.

Anne Murphy: That's a little, that's the bridge. Too far.

Kyle Shannon: A little bridge too far. Um, yeah. AI is real now more than ever. Yeah, exactly. And, and, um, and the, the other thing that's happening within the AI salon with, within the, the practice lab where we have these weekly meetings for people that are designing their daily practice around ai.

Anne Murphy: Totally.

Kyle Shannon: But the other thing that I'm seeing, which I'm really digging is people rediscovering.

Rediscovering the things that they loved to do before AI was here. Yeah. So Kevin Clark, for example, is now writing an hour a day with a paper and a pen. Yeah. Cindy Coen cleaned up and is now using her art studio doing watercolor illustrations and things that gave her joy, and she's actually incorporating them into her AI work.

But there's something about, um, people integrating AI in this more holistic way that they're realizing that all of who they are is important and AI is some, you know, augmentation to that. But that, that, that centering of who they are is really important. So that, that very much tracks that people are coming in serious.

music: Mm-hmm.

Kyle Shannon: I think we're just gonna start to see things that are different. Like in the past week, um, three unsolvable math problems were solved by chat.

GPT 5.2 Pro, which is new.

Anne Murphy: Yeah.

n/a: Yeah.

n/a: Mm-hmm.

Anne Murphy: So I think, so I wanna share something about Cindy and about art, because it gives me an opportunity to talk about the Crate conference first.

Oh, good. So, um, Cindy last year, she was like, you know, you know what you need is a craft corner.

Kyle Shannon: Oh yeah.

Anne Murphy: And I'm like, I'm, I'm envisioning like spray painting macaroni. And I'm like, I don't know if we need a craft corner. You know, I'm not so sure. Well, Cindy

Kyle Shannon: painting macaroni, you definitely need extra glitter glue.

Kyle Shannon: Oh, that's great.

Anne Murphy: Yeah. Yeah. They need to, they have to, we have to get like a decoder ring at the end to figure out what our little thing meant. So what the

Kyle Shannon: secret messages. Oh, that's really great. That's really

Anne Murphy: great. This is the first thing, the first activity that we have confirmed for create and it's art.

It's correct.

Kyle Shannon: And just to be clear, they can get info for Create at, she leads ai.ai, correct?

Anne Murphy: Yeah. In like one and a half days. 'cause we're trying to launch. Yeah.

Kyle Shannon: Okay, cool. Go check it out. Um, no, that, that's, that's super important because, um, what, what Cindy has described, and Kevin Clark described this a bit to me and some of the others in the Mastermind, is that how they're using these AI or these analog moments is to.

n/a: Mm-hmm.

Kyle Shannon: Right. Either you get overstimulated and you have all these exciting ideas and, and you're just like, you know, adrenaline junkie out. You're endorphin right? Or you see the other side of it. You're like, oh my God, these things are so capable.

What's gonna be my role in the future? It can be anxiety producing, and what I'm finding people doing is, is they're using these other modes of their life to recenter, bring it down, calm down what's important, and, and keep that at the center.

Anne Murphy: Yep.

Kyle Shannon: That seems, that seems critical. I, you know, I'm even thinking back when we started this, even when we started this, this was much more about trying, I think we were lamenting the fact that we could no longer keep up with the technology, but we were still kinda dealing with the technology.

Anne Murphy: art. An analog art. An art analog lab or a analog art lab. Yeah,

Kyle Shannon: that's good.

Anne Murphy: Yeah, that's

Kyle Shannon: good.

Anne Murphy: And it's gonna have all kinds of stuff.

And so,

Kyle Shannon: and is it just gonna be live throughout the thing where people can go there and play like whenever they want? If they need

Anne Murphy: to, I dunno. Because everyone's gonna be doing crafts and not going to the sessions, so

Kyle Shannon: there's gonna be so much macaroni.

Anne Murphy: Look at me. Sorry.

Kyle Shannon: You just got shorter.

Anne Murphy: I don't know what's happening.

Okay. Um, what do you, you need to talk, you wanna talk about, or did you already talk about the, the, the mastermind kind of in a way?

And, and we recently created this thing called the, um, AI Salon Mastermind practice, which is a structured daily practice. And if you're part of the Mastermind, which is the subscription area of the AI salon, you can join us on a weekly basis where we talk about and are walking people through, setting up a daily practice.

Um. As someone who leads it. Aw, look at that. That's so cute.

This

Anne Murphy: is, this is, um, Ezra Izzy.

Kyle Shannon: Hey Izzy.

Anne Murphy: He's my shadow this year, this week because everybody's gone here.

Kyle Shannon: Oh, that's hilarious.

Anne Murphy: He's gonna join us.

Kyle Shannon: Um, but the, the, uh, the AI Salon practice lab, um, even though I am help, I'm co-leading it with Liz Miller Hirschfeld.

Anne Murphy: Yeah.

Kyle Shannon: And, and having it with intentionality. And, um, one night on my live, Liz came on my live and, and I said, I want to turn my live into a part of my practice.

And she asked me the question, what do you want more of? Very simple question. Oh, it destroyed me, Anne. Wow. It destroyed me because it's like when you, when you really, you know, think about the answer to that question, you get to, well, wait, so why am I not doing that? And what do I really want? And what might that look like?

And, and so a daily practice is, is a, it's a wild, it's a wild thing and it's a powerful thing, but it's not always a pleasant thing. Like I think aspiration, like, yeah, I'm gonna have a daily practice and it's gonna be awesome. Yeah. But it's,

I

Anne Murphy: mean, it's, I, I would say that you've been going through it, as they say

Kyle Shannon: that night where she asked me, what do you want more of?

That destroyed me publicly.

Kyle Shannon: Yes. Well, I did, I did a TikTok that was something about, you know, what I want more of. And then all the comments were like, well, you know, you're, we hope you're okay, Kyle. And I was like, no, I'm okay.

But it's just like, and that's the, the whole point of the, the Mastermind practice lab is to be able to go through that stuff with other people who are also doing it. And what's really powerful about it, Ann, is it's just, it's it, like you said it before, people are sort of stepping up and taking their relationship with AI and what's happening more seriously and really trying to integrate it into who they are and what they believe and the change they wanna make in the world.

And so it's, it's quite powerful. So anyway,

Anne Murphy: agree.

Katie Dunn: Hi. Hello,

Kyle Shannon: Katie.

Katie Dunn: Hi, guys. How are you? Good. We're

Kyle Shannon: doing doing great. We're doing great. We're, uh, we're, we're confronting dealing with this AI stuff. How are, how are you holding up? Well, first of all, wait, I'm, I'm gonna be good. Wait. You did it. You introduce yourself. Tell us, Kyle, want the people to know about us or about you.

Katie Dunn: Okay, I'll do that. Hi everybody. I'm Katie Dunn. I'm an angel investor. Board director and startup advisor. And my superpower, as I like to say, is helping people get really clear on their communication so that they can get investors, customers, and partners.

music: Mm-hmm.

Katie Dunn: Uh, but I have to, I have a comment, I have to make a comment before we get into things.

The whole like, offline, online ai, non-AI thing. So I am taking an oil painting class.

music: Good.

n/a: Mm-hmm.

Katie Dunn: And I really loved it, but I didn't keep it up after the class. Mm-hmm.

And so this year I'm starting it off and I'm gonna keep doing it, but it's really, it, it's one of those things that's, it's pretty amazing because you cannot think about anything else when you're doing it. Yeah. Mm-hmm. You have to be 100% focused, which I, I think. There's some crafts. Like I, I've also been a knitter, I've been a needle pointer.

You know, like the, all those kinds of things. You can watch TV and do that, or you can mm-hmm. Have a conversation and do that. I, I like painting is one of those things you have to solely focus. Yeah. Yeah.

music: Mm-hmm.

Katie Dunn: Which I love. 'cause I come out and I feel like, okay. It's almost like relaxing because you come out and your head is so clear.

Kyle Shannon: that's exactly what we've been hearing from people in the Mastermind is that it, it, 'cause there's something about AI that's the opposite of that, right?

Mm-hmm. Because it's like in an idea and 10 more come back at you and eight of them excite you and then you're in this, it's a frenetic kind of experience, right? And so,

Katie Dunn: totally.

Kyle Shannon: Yeah. And

Katie Dunn: AI is always on, so it's almost like. Sometimes I feel guilty. This is, I feel guilty that I'm not, if I'm on social media, for example, or I am, you know, I'm, I'm, I don't even know whatever, doing something else, and I could be on AI and like doing more things for my business, I feel guilty about it because AI is always on and it's

Anne Murphy: hundred percent.

Katie Dunn: So yeah, it's a little bit of a, like, I gotta be okay with it.

Wow. So we're not picking it up in our heads. It's, it's very real. It's very real. And when you recognize that though, that has really helped me understand that doing stuff offline off AI is absolutely critical to my mental health. Mm-hmm.

n/a: Yeah. Yeah.

Anne Murphy: And that I don't wanna, I don't wanna risk that, I don't wanna risk that, you know?

n/a: Mm-hmm.

But

Kyle Shannon: yeah.

Katie Dunn: You know, it's a

Introduction: Yeah.

Kyle Shannon: So yeah, go ahead.

Anne Murphy: I have, I have a good one. I think, um, I feel like in looking at your background and, and getting to hear you talk on TikTok, I feel like your person who has made a lot of high stakes decisions in your life, would you say that's true?

I,

Katie Dunn: yeah, I would say that's true. Yeah.

Anne Murphy: And what I, so what I was wondering as we were talking about it, was how much of that comes from intuition and how much of it came from knowledge and insights, would you say?

Anne Murphy: Mm-hmm.

Katie Dunn: You know, I'm very lucky. My parents are amazing and. Very stable. My dad like, was very integral in me being a finance person, Uhhuh, uh, you know, and, and teaching me finance, teaching me basics of budgeting and just, you know, giving me a lot of, uh, education to support myself and

Anne Murphy: yeah.

Katie Dunn: You know, I, I, before I was, became an, an investor and advisor full time, I was in commercial real estate and worked in banking

Anne Murphy: Yep.

Katie Dunn: For five years. And that's a very male dominated area.

Anne Murphy: Yep.

Is important. Like, 'cause I, 'cause making a lot of investments. I've made 30 investments and the ones that I have not trusted my gut on have failed. It's so like, it's so, it's so, right.

Kyle Shannon: Yeah. And, and what is it? They looked good on paper. You, you essentially talked yourself out of not investing in it is like,

Katie Dunn: no, I talked myself into investing in, I would say

Kyle Shannon: You

Katie Dunn: talked

Kyle Shannon: into investing in it?

Yeah. Be 'cause what? Because some external factor looked good. Like what, what was it that made you,

Katie Dunn: I think

Kyle Shannon: some of your instinct?

Wow. And then, um, yeah, and then another one, another one was a friend of a friend.

music: Hmm.

Katie Dunn: And so they were doing it, so I wanted to do it. Mm-hmm.

music: Yeah.

Katie Dunn: And you know, that, that kind of thing. So it's, and a lot of it too was probably in my early days of investing, of just thinking like, the, this opportunity came to me, so I should, I should do it.

And it's not that I didn't do due diligence and I didn't, you know, but it's, it's probably a, I probably didn't put in more money than I should have in, in some of the earlier deals.

Kyle Shannon: And what's it, what's it feel like when it's Right. When the, when the, when the instinct is there, the intuition is there.

It's

Yeah. Yeah. A good BS meter. Okay. A good bullshit meter, uh, that I very focused on. I, if you use a lot of buzzwords and you don't answer questions directly and you're pie in the sky all the time, it's not gonna be a good fit. That's not gonna work. I need somebody that's, that understands how to explain things to me simply and easily.

That really sees the clear vision for things. And that you, you can tell. So, sorry, my dogs.

Anne Murphy: Nope, same.

Katie Dunn: Doing something crazy.

Kyle Shannon: I've got one in here. Ready to, ready find. We're all good.

Katie Dunn: Yeah.

Kyle Shannon: We're dog friendly here.

Katie Dunn: Good. So we, but yes, so it's, it's a, it's a really, it's a strong feeling that I, I know the, and it's

Anne Murphy: awesome.

Kyle Shannon: Yeah. Yeah. Yeah.

Katie Dunn: Awesome.

Kyle Shannon: What, um, do you have, can, can you talk about your thesis and or like how that's evolving?

If it's evolving? What are you excited about these days? I'm just curious, you know, what, what you're looking for for anyone listening or watching. Um, what are the kinds of things

Katie Dunn: you're looking for? My first lens is underrepresented founder. Mm-hmm. Uh, you know, the, the women getting less than 2% of VC drives me bananas.

Heavily invested in beverage. I don't wanna do any more beverage right now. I need an exit from beverage before I do more. And then, uh, and then tech, so

music: mm-hmm.

Katie Dunn: By tech. I've done mo, most of the investments I've done recently are, are more tech focused. Mm-hmm. They're, you know, I don't, when I, I don't, I specifically don't say AI because mm-hmm.

I think AI should be baked into every single business. Yep.

Yep.

And I wanna make sure you're solving a real problem.

Yeah.

That don't you think Chachi, PT and Claude and they're are, they're gonna be able to do all these things that all these people built businesses around?

Kyle Shannon: It was actually one of

Katie Dunn: my,

Kyle Shannon: it was gonna be one of my questions to you. I'm glad you said it. Like, it's so bad. I have this gold button I use on my live.

music: You can make money with cha.

Kyle Shannon: That, that there, there are so many people that are just out there like, like we're in this, we're not quite in the frothiness of the, of the late nineties with the web stuff, but we're getting close and it's like. Uh, like what you said is like people should be solving a real problem.

It seems so obvious on the surface, right? Yeah. It seems so obvious, but

Anne Murphy: this is my O one and only sticky note in my whole entire life, and it says, what problem are we solving?

Kyle Shannon: Yeah.

Katie Dunn: Oh, there you go.

Kyle Shannon: This is

Anne Murphy: literally, and I got this from Suzanne Wilger. Jergens, of course, Kyle.

Kyle Shannon: Oh, that's great.

Anne Murphy: What is the problem we are actually solving?

Kyle Shannon: Exactly. And you

Anne Murphy: even silly and like poser ish if we keep saying ai, you know?

Kyle Shannon: Mm-hmm.

Anne Murphy: Ai this, AI that it's like,

Kyle Shannon: yeah,

Anne Murphy: yeah, but we get that now that's baked in to, to your point, it's baked in.

Kyle Shannon: Yeah. I think there's even a thing about this stuff we were talking about with analog and, you know, oil painting and or origami and whatever you, you do that's outside of that, I think, I think founders that are truly solving a problem.

You know, a they're gonna have to be nimble and adaptable. I think that's just, yeah. One of the new realities of the world is everyone's, we, we are all gonna have to adapt as these technologies evolve and get stronger. And I think that those founders that can look at the problem first and then, and then sure, be nimble with ai, but there might be some analog solution to the problem that's actually novel and interesting when combined with ai.

Katie Dunn: Yeah. There's, there's a lot of people out there that are building solutions. They're not solving problems.

They're trying to find the problem after they've built the solution. And that's, that's the thing that gets scary is I look for founders that are obsessed with the problem, not obsessed with their product.

Kyle Shannon: That's great. That's great. Mm-hmm. Well, it's also one of the, one of the real challenges of Vibe coding isn't It?

Is yeah. It can give you a solution so quickly that you're like, Ooh, this is a value. Well, it may or may not be right. Not

Anne Murphy: to everybody else. Yeah. I actually have been, have been spending a lot more time in the last couple of months with women who, women vibe coders and the, that pattern actually concerns me quite a bit.

Mm-hmm. Like you could, you could do a lot of things in this greater industry. Um, more it, I mean, particularly if you have like revenue goals, like it's gonna be a while. Mm-hmm. I'd like to see more women. I don't know. I'd like to see more women doing some of the, more of the other things along the way.

Katie Dunn: Yeah.

Sort of living in what's happening.

Katie Dunn: Yeah. There's a, one of the, uh, more recent investments I did is a company called Good Word, which is like your chief of staff network mining your network, helping you manage your network product.

music: Mm-hmm.

Katie Dunn: And it's an app and a web-based platform hooks up to your LinkedIn, your Google calendar, uh, your email, all that stuff.

So it really helps you understand how you know somebody and what the history of it is. Mm-hmm. And you can add notes. It has a whole chat feature. So you could, I could, I could go in and say, put to both of your, I could say to one thing, I could say, uh, did Anne and Kyle's podcast on January 14th? You know, make a note of that and it will go to both of your.

Um, and now that now she's the founder of this and then her, the co-founder. Yeah. This is a, her co-founder

n/a: Cool.

Katie Dunn: For nine startups and is the technical guy. And they are such a good pair. Hmm. He has seen so much stuff. And there's, there's something about having that, that combo of the non-technical, with the technical mm-hmm.

Right. Right. Mm-hmm. And it's, you still have to have that robust system to be able to take on a bunch of users and not fail and protect the data and make sure all of that information is safe. And, you know, there's so many other nuances to it that you. People that are vibe, coding something and selling it, they're not thinking about those things.

Right.

Kyle Shannon: Scalability's a real thing,

Katie Dunn: right?

Kyle Shannon: Yeah, yeah.

Katie Dunn: Especially around data privacy too. I worry about that for

Anne Murphy: Oh, a hundred percent.

Katie Dunn: So many founders. A

Katie Dunn: cool.

Anne Murphy: Go for It's great.

Katie Dunn: Yeah. You'll love it. I love it'll, yeah. And you should follow on TikTok if you're not already.

Okay. She's the, uh, founding, uh, the founding head of growth and her tiktoks are amazing. She's

Anne Murphy: Oh, really?

Katie Dunn: Yeah, she's great.

Anne Murphy: Yay. So,

Katie Dunn: yeah.

Anne Murphy: Oh, go ahead.

Katie Dunn: No, go ahead. You go ahead. Sorry.

Anne Murphy: I was gonna, I was gonna ask you when. When they approached you or you approached them or somebody connected, connected you with them, what did you particularly appreciate about their approach to potentially working with you?

Because I love it on, so we talk about generously leading and when you, on your tiktoks go through, like, I went through a pitch deck to, you know, three of 'em today and here's what I didn't like about them. So what hap or, or what I did, like what, what about Good word was what did it for you?

She was, uh, at chief, the, the Women's Network. Mm-hmm. Which I was a part of. So I knew her through that. And I knew she was building something about a year before she had come to a breakfast that I was speaking at and came up to me and said, Hey, I'm, I'm building something. I wanna tell you about it when I get it sorted out.

And I was like, great. Yeah. Come to me. And so basically that's what she did and I love that she. Had given me that preemptive thing. Yeah,

I love

that. I'm smart that, yeah. And she's, she's one of those people that's just made to be a founder. I, she's just so smart and thoughtful and analytical and has prepared herself for this very, very well.

And you know, I know that's not as big as every, some people and all that, but I, for me, that's a big a lot of humans. Lot. Yeah,

Anne Murphy: yeah,

Mm-hmm. And so I've met all the, it feels like drinking from a fire hose all the time. So I need a way to manage who have I met where and what is important? How did I wanna follow up with them? What if I wanna introduce these two people, you know, how do I write the email to introduce these two people?

Yep. You know? Yeah. That's like, I'll never find them. Sorry, I can't find them.

Anne Murphy: Yeah. Yeah.

music: That's

Anne Murphy: so

Katie Dunn: awesome. So that's what I really loved. They were solving a real problem that I had and I really was loved the founders and that, that, you know, I invested and, and ran a syndicate for them pre. Uh, pre-product.

Mm-hmm. And so they launched this October and I've been a beta user. I've been, or, you know, an alpha user and beta user and giving them feedback all along the way and, you know, talk to them all the time. So it's been, uh, it's been super fun to watch the, and just see how incredibly fast they can move and build and launch that,

Kyle Shannon: that, that's so exciting.

How do we navigate around that? Right. So I think that's huge. Um, I wanna, you, you brought up, you, you mentioned something about the, the, the female co-founder of, of good word that you said. She's just, she's so naturally an entrepreneur. She was meant to be an entrepreneur. So I'm, I'm paraphrasing exactly what you said.

It's my belief that we're about to enter an era where a lot of people are gonna be forced into entrepreneurship that might not be natural entrepreneurs and born, but they're gonna have to figure it out. So I'm curious, you know, either, do you have any experience with founders that you feel are, not that, but they're, they're learning it, you know, they're, they're, they're getting better at it.

Katie Dunn: Yeah.

Kyle Shannon: Now you're gonna have to do something on your own. Do you have any advice for, for that?

And I'm curious if you believe that that's coming as well. Actually, I'm just making a big in here.

Katie Dunn: Yeah, I do. I mean, I do think there's gonna be jobs eliminated by ai. We've seen it and you know, I think there's, there could be a correction. You know, there's the things that I worry about, you know, I think back to my experience in banking where you had the analysts that you would, you know, I would train the analysts every couple years I'd have a new analyst that would come in and work for me and then I'd be training them on how to build the models and how to write about our deals and put together the, the memos that we'd have to do all that kind of stuff.

Yeah. And understand that what goes into a deal getting done. Mm-hmm. Because you have, that's how you learn how to deals get done by working on the models and by writing about it. And by doing the research and doing the due diligence. If you're just popping in an address and it's spitting out all this stuff and you're not even looking at it, you're just putting it into the memo and you don't get it, you're never gonna get to the next level.

So I do worry a little bit about that is how are you gonna train people?

music: Yeah.

Katie Dunn: Uh, but to answer your question a little more directly, Kyle, the, the advice I would say to people is niche down. Don't try to be everything to everybody. I think people, you know, when I was in the process of leaving my. I, I asked my company to lay me off to gimme a package, and they did.

music: Mm-hmm.

Katie Dunn: But she was like, well, I think a lot of your, the founders that I work with would benefit from your advice.

How do you think you can help them? And I was like, um, I don't know. Like I, I think I would be good at, I give them good advice too, but when you really think about it, you've got niche down and have a very specific offer that you're bringing and something that you talk about that you can say, I know exactly how I can help you.

This is what I do.

music: Mm-hmm.

Katie Dunn: And it's if you're not, if you try to be everything to every. Buddy, you're nothing to no one. Right,

music: exactly.

I tell kids, teenagers, yeah, college kids. I know you can't use AI for school. Figure it out. Figure out out ways to play with it on your, on your own. Mm-hmm. Don't use it for school work. There's plenty of other things to do with it, but it's a, you know, you've got to learn it. So if you could, if you could learn the AI of what you did in your job and create something and then go to your, the customers or competitors or your people you used to serve and say like, Hey, I've got a new thing.

This is how I'm doing it. It's cheaper, faster, more efficient. You're gonna have better results, blah, blah, blah, blah, blah. Like that. Finding ways to add value and the ways you can add value are saving people time or saving people money. Yeah. So focusing on those two things, time, and anybody will, people will buy time and they will buy something that saves them more money.

Anne Murphy: Yeah. Okay, so, um, I was just catching up on our, on our chat. We are obsessed with digital twins and I know you have really good digital twins, and I would just love to launch into a little bit of a conversation about, um, any, like, take it any direction. Topic is digital twins. Where do you wanna go with it

Kyle Shannon: and go?

Katie Dunn: Yes. I mean, I love them. I love them. Yeah. I spent a lot of time building them and I didn't do it in chat. Bt I used a platform called Delphi. It's delphi.ai. And it's a, I chose that platform because of the security around it and because of the interface and the fact that you have to be a real person

music: mm-hmm.

Anne Murphy: Yeah.

Katie Dunn: Or Claude's words. It's, it's my, everything is built, built on my frameworks. Mm-hmm. And the really cool thing is they, it sort of learns what you're talking about. You give it purpose. You, so I have two. One is one I call the advisor. That's the nice Katie. She's the one that will answer like, she's meant to answer the kind of questions for that first time founder that thinks they need to fundraise, isn't really sure, doesn't know what it entails, wants a safe place to ask questions and to learn.

Kyle Shannon: think so, yeah.

I just, I just muted her so we're good. I'll

Katie Dunn: unmute her. So the, I, you know, the investor is, is really a challenger to, you can upload your pitch deck and she'll pick it apart. You can, you can give her, you pitch out loud and she'll say like, you weren't clear here, you stumbled there. You, uh, you know, there's things that you need to work on, uh, on this section.

Like she'll really, and she'll help you frame it out. Like make sure that you're saying it accurately and help you. I've had one founder that's one over a hundred, well actually two founders have won over a hundred thousand dollars. In grants using the digital twins to help frame their answers to,

music: yeah.

Kyle Shannon: based on, based on how people are interacting with it, it says, Ooh, people are asking about this thing that you don't have a point of view on.

Something like that.

Katie Dunn: That, and also as you're building it, it learns like what you're, the goals are and will say, suggest things. Yeah. Wow. So that was, that was super helpful.

Kyle Shannon: That's great.

Katie Dunn: That was, that was a big, and I can't remember if we talked about this before the, we got on live or after, but this was, that was a big thing that I dumped.

Like, I just went through these questions, just answered question after question after question, and yeah. Used, helped had GBT help me put it into a cohesive framework.

Kyle Shannon: So yeah, sort sort through it. Sort through it.

Katie Dunn: Yeah.

Kyle Shannon: That, that's really amazing. Now is Delphi, is it, is it just text interaction right now?

Katie Dunn: voice? Yeah, it's, it's voice. It's just like, like Chachi pt, you can dictate to it. You can, uh, message, you know, type messages or you can talk, and I, my voice talks back. Okay. They do have the ability for an avatar, but it's, for me, it's a little, yeah, yeah, yeah.

Kyle Shannon: I, I'm, I'm excited for when the avatars don't suck, but they still kinda suck.

So

Katie Dunn: there's, there's another one, another avatar one that I, I do like, and I've been thinking about. Uh, I met with a founder called Connection, and it's C-O-N-N-X-N-I think it is. Mm-hmm. Uh, but they. It's, it's better, the avatar is a lot better. Mm-hmm. Yeah. So it's pretty cool.

Kyle Shannon: Again, I think, you know, we're not that, we're not that far from those things being, being really close.

Katie Dunn: I do look at everything.

I look at every conversation because I wanna make sure everything's accurate. Um, especially like the, the first couple months it was, there were, you know, I wanted to make sure it wasn't recommending things that wouldn't really recommend. Yeah,

yeah, yeah.

Uh, just 'cause yeah, it's got that part's gotten a lot better.

Uh, but, but yes, I do, I do look at those things and I'll pop in there and sometimes I can message them. So after the chat, you get a email with a summary of the conversation and. Uh, but I can message them through the platform and it will send them an email and say the, Hey, the real Katie sent you a message.

Kyle Shannon: That's so

Anne Murphy: cool. Wow.

Katie Dunn: Yeah, it's great.

Anne Murphy: So in case you see something and you're like, I just wanted to also add that.

Katie Dunn: Yeah.

Anne Murphy: What a wonderful

Anne Murphy: that's so awesome.

Katie Dunn: Yeah. That's

Kyle Shannon: so cool. That's so cool. Yeah, it's fun. And do you, are you promoting them?

Like how are people finding them? What's, what's your, and and,

Katie Dunn: yeah, that's question not, well,

Kyle Shannon: what's its role for you is its role to offload these conversations?

Katie Dunn: Yeah. So I built them for a couple reasons. One is I get 20 to 30 DMS a day, I would say, with people saying, can I pick your brain? Can I talk to you?

Can I pitch you? Can I do this? Can I do that? So I. I will say, you know, I'm sorry, are you? Yes, you can talk to me. I'm very expensive. You can book me on Hubble, I'm $275 for half an hour, or you can talk to my digital twin for $15 a month. Mm-hmm. Like, that's a much better trade off. Right. Especially if you're founders, we know.

Right. They're always on, they're,

Kyle Shannon: they read everything

Katie Dunn: prepared. Yeah, they're prepared. They're thorough, they put it all out in a nice format right away. It's great. So I use them literally all day long too. Wow. So. Create, create content, all the, all the things. Uh, so it's, they're pretty great. So the, my, have I promoted them?

No. Not as I promote them in my dms and I mm-hmm. I, you know, I've talked about, I did do a demo of them on a podcast, uh, another podcast. But yeah, it's, they, I'm actually, I have a marketing person that's helping me to put together a marketing plan for them. So, yeah.

Kyle Shannon: Because I'm thinking it seems like it's a very valuable thing, and it could be People want

Anne Murphy: that.

Yeah. They need it.

Katie Dunn: Yeah. And it's, yeah. And that's, I just, I like that. It's, it's my, all my stuff like that, it can't be. Mm-hmm. It's not anybody else's. It's my, and, and that's what you're, you should be like, look, I am one opinion, but I've been very successful in helping people raise millions and millions and millions of dollars.

So. You can, you know, take it for what it's worth.

Kyle Shannon: Right.

Katie Dunn: A lot of people say, my opinion's pretty good.

Kyle Shannon: Yeah. Hey, figure some stuff out. And now that those smarts are in, in these digital twins.

Katie Dunn: Yeah.

Kyle Shannon: How do you do, how do you anticipate them evolving as the technology improves? Do you have any sense of that?

Katie Dunn: I, I think that probably the next thing is the avatar.

Yeah.

I, but I, the thing is, there's sometimes where I don't know about you guys, but like. My, my chat to bet is called Charlie. Mm-hmm. And she just annoys me when she talks sometimes. Mm-hmm. Like, she talks too much. I just wanna answer. I just want to That's a great idea.

And on. Yeah. But you know what I mean? So like, I, sometimes I, when I'm cooking, I want her to talk to me. Mm. And I want her Charlie to, to say like, what comes next in the recipe? And uhhuh, you know, so that's, that's fine. But there's other times where I'm like, just gimme the fricking answer Charlie. So, so there's, I want, I think that the ability to choose you've got is a good thing to have.

Mm-hmm. And how you want to be spoken, how you wanna interact with them. I think there's so much flexibility with it.

Kyle Shannon: Yeah. I think that's a great point. I hadn't, I hadn't thought about that, but just the nuance of. Modes like that, that it's got enough context and enough memory that, oh, Katie's in a no-nonsense mode here.

Katie Dunn: Yeah, yeah.

Kyle Shannon: That would be really good. Because yeah, you're right. Like I, mine mine's name is Quinn and, uh, okay. I, I, uh, sometimes I'm like, oh, I should go use, I should go talk to Quinn. And I'm like, I don't feel like dealing, like with all of her crap.

I don't wanna tell her to not talk to me, you know, don't answer anything until I tell you to. And then she does anyway.

music: Yeah.

Kyle Shannon: Yeah.

Katie Dunn: Exactly.

Kyle Shannon: Oh, that's exciting. Well, at where do, where do people find, uh, find your digital twins?

Katie Dunn: They are, uh, they're on my website, the masthead strategy.com. There's, uh, a page there that they can, they can, uh, learn more about them and then.

Go talk to 'em.

Kyle Shannon: Great. That's lovely.

Katie Dunn: Yeah.

Yeah.

Like

Katie Dunn: I'll give you my link enough. Yeah,

Anne Murphy: yeah.

Katie Dunn: Yeah. It took me, like, I have to say, it took me a long time to build it out and I, and that was, you know, part of that was the, me learning their platform, part of it was me, um, just not having a ton of time. Mm-hmm. But it was, it was now it's like second nature and it's, it's very, it is intuitive and it's, uh,

Anne Murphy: yeah.

Katie Dunn: But it's, it's great. It's really helpful.

Anne Murphy: Love it. You, you,

Katie Dunn: I have some, another friend that's gonna, that are gonna use it to, they have a community and they're gonna use it to help onboard people and to just

Anne Murphy: ah,

Yep.

Kyle Shannon: That's great.

Katie Dunn: That, yeah. So it's, it's, it's very useful's, so smart. There's so many use cases.

Kyle Shannon: Yeah. Yeah. So good. I'm also, the, the other thing that, that you said, but we didn't really hit on too much, I think it's actually really important. You've got the, the nice, the onboarding Katie, and then you've got the investor, Katie.

This idea of us having different personas of different versions of ourselves that we put out there, I could see that being. A really powerful skill in the future that you might have some of your digital twins that know all of your personal information and they might talk to doctors and lawyers and things like that.

Others or social entities and some that are professional entities. And so I think you're, you're, you're already sort of marching down a path that feels like it's gonna be a skill moving forward.

Katie Dunn: Yeah. I, and I think we've learned that, right? That there's giving certain, giving the AI like a perspective and context and it performs better.

music: Yeah, same

Katie Dunn: to do the next one.

music: Yeah.

Katie Dunn: Just because it just, it keeps things a little more streamlined.

It doesn't get confused. It, it just knows its purpose. And so I, that's why I did it for this. I, you know, it would be interesting if I do, I wonder, I think a little bit there could be confusion of which one do I use for the customer. Mm-hmm. So I'm working on that part of messaging of, oh, well if I don't, you know, is it gonna be able to ans is, does the advisor review decks?

Absolutely. Does the investor do it better? Yes. Right, right, right. So it's kind of that kind of thing.

Kyle Shannon: Yeah, that's You're gonna need a, you're gonna need a, a routing. Katie, you're gonna really wanna talk to here. Yeah.

Katie Dunn: Yeah.

Anne Murphy: I'm your triage.

Kyle Shannon: Yeah. She, triage. Triage Katie.

Kyle Shannon: Um, okay, so final question. We ask this to all of our guests.

Um, what does AI readiness mean to you and what would you say to someone just, just getting into this crazy game that we're all playing in?

Katie Dunn: Uh, I think AI read readiness is, uh, table stake. Honestly, I think you, if you are resisting it, you are gonna get left behind. Uh, and that AI readiness can be, but it can be as simple as I just use chat GBT to, to cook with.

Anne Murphy: Yeah. Mm-hmm.

Like ask, asking AI how it can help you.

n/a: Yeah.

Anne Murphy: Yeah.

Katie Dunn: It will tell you.

Anne Murphy: Yeah.

So.

Katie Dunn: And it, the way it learns. Like I, you know, when chat to BT a couple weeks ago got the integration with Lovable mm-hmm. And it, I, I just kind of screwing around and said, you know, Hey, what should we do together? And it like gave me like five different, or even more, I think 10 different things that knowing me, knowing how much I talked to it, it gave me 10 ideas of vibe, code, things.

I should vibe code with it right then and there. Oh, that's so cool. These are

music: good

Katie Dunn: ideas, you know? That's so cool. So yeah, just, just the playing around with it, talk to it, whatever mode. Back to the mode thing, whatever mode you works for, you do it.

Anne Murphy: Yep, yep.

They ask it all the time. They, you know, they're. I, I just, I feel like you've gotta be on the, everyone should, it's gonna make our lives easier. Let it like, make your life easier.

Kyle Shannon: Let it make your life easier. Yeah. Just be, be curious, like what you're talking to is curiosity, right? If you, if you just cook it right, you'll see, oh, it helps me more than I thought.

Which will then inspire you to go, well what, wonder if we could help over here? And the answer's yes. Right? So.

Katie Dunn: Yep.

Kyle Shannon: Awesome. That's awesome. Yeah. So folks should check out the masthead strategy.com. Anywhere else we should find you.

Katie Dunn: Anything

Kyle Shannon: else?

Katie Dunn: Yeah, I'm on LinkedIn, uh, a lot. Katie Dunn. And I am on TikTok.

I am Katie. Dun. My handle there. I heard that there's like, um, and Anne, this probably, or Kyle, does this happen to you guys where there's like people impersonating you out there?

Kyle Shannon: Yep.

Kyle Shannon: Oh, yeah. Then they try to sell your, your followers, uh, crypto and financial services.

Anne Murphy: Yeah.

Kyle Shannon: Uh, TikTok doesn't care.

Anne Murphy: Yeah.

Kyle Shannon: You can report them and tell your people to report them, and they will, and then nothing happens.

Anne Murphy: Yeah.

Kyle Shannon: Just crazy. Yeah. I guess they're making money on the scammers, just like they're making money on us. So it's good for, good for business, I suppose.

Katie Dunn: Yeah. So, and the sugar daddies, they have been,

music: oh, the sugar

Katie Dunn: daddy, they're hilarious.

music: Oh my

Katie Dunn: god. $7,000. They always wanna gimme $7,000 a month. Like, here's my, I literally, now I just say, great, here's my cash.

n/a: Yeah,

Katie Dunn: and they're like, I do. And it's my real cash app. I'm still waiting for the $7,000. You

n/a: haven't gotten one yet?

Katie Dunn: No. Always wanna talk on Telegram and I say no.

n/a: No. Good. I'm good. Yeah, I think I'm

Anne Murphy: good.

Kyle Shannon: It's so good.

Katie Dunn: That's good. I'm glad. Yeah.

Kyle Shannon: Katie, thank you so much.

Katie Dunn: Yeah, well thank you guys for having me. I really enjoyed it. It's been a very fun discussion.

Anne Murphy: I'm so glad.

Katie Dunn: Thank so glad you guys so much.

Kyle Shannon: Bye-bye.

Anne Murphy: Take care.