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.

𝗢𝘂𝗿 𝗚𝘂𝗲𝘀𝘁:

Kimberly Offord is an award-winning AI Filmmaker and creative visionary whose work sits at the intersection of music, culture, and technology. She has produced groundbreaking AI-generated music videos for two Grammy-winning artists, including three official projects for Lalah Hathaway’s VANTABLACK album: the original “Tunnels” video, the official Tunnels Remix video, and the viral reel “Black.” Her work also includes a music video for singer Sy Smith and cinematic projects for entrepreneurs and corporate clients such as Bronner Brothers. Kimberly’s AI short film Cafe Conversations placed in the Top 50 of the Reply AI Film Festival in Venice, highlighting her global recognition in the AI film movement. She is also the creator of the Playground Pastime AI Film Contest, the Chicago AI Film Festival, and the Black AI Film Festival launching in 2026—initiatives that are defining new spaces for underrepresented voices in AI-driven storytelling.

𝗦𝗵𝗼𝘄 𝗢𝘃𝗲𝗿𝘃𝗶𝗲𝘄:

AI isn’t replacing filmmakers—it’s removing the gatekeepers. In this conversation, Kimberly Offord, founder of Playground Pastime and the Chicago AI Film Festival, shares how AI is reshaping visual storytelling and clearing space for underrepresented voices to lead a new cinematic movement.

Listeners will get a front-row seat to two standout AI films, including last year’s Festival Winner, and hear how the Playground Pastime ecosystem is opening doors for creators who’ve traditionally been kept out of the industry. This is a conversation about technology, but even more so about access, visibility, and rewriting the script on who gets to tell powerful stories.

𝗝𝗼𝗶𝗻 𝗨𝘀:

The AI Readiness Project airs every Wednesday at 3pm with hosts Anne Murphy of She Leads AI and Kyle Shannon of The AI Salon. Subscribe to stay connected to the people shaping what’s next.

"𝘐𝘧 𝘺𝘰𝘶'𝘳𝘦 𝘢 𝘤𝘳𝘦𝘢𝘵𝘪𝘷𝘦 𝘱𝘦𝘳𝘴𝘰𝘯 𝘢𝘯𝘥 𝘺𝘰𝘶 𝘩𝘢𝘷𝘦 𝘴𝘰𝘮𝘦 𝘨𝘳𝘦𝘢𝘵 𝘪𝘥𝘦𝘢𝘴, 𝘸𝘩𝘺 𝘸𝘰𝘶𝘭𝘥𝘯'𝘵 𝘺𝘰𝘶 𝘶𝘴𝘦 𝘈𝘐 𝘵𝘰 𝘣𝘳𝘪𝘯𝘨 𝘺𝘰𝘶𝘳 𝘴𝘵𝘶𝘧𝘧 𝘵𝘰 𝘭𝘪𝘧𝘦? 𝘐 𝘤𝘰𝘶𝘭𝘥 𝘯𝘦𝘷𝘦𝘳 𝘥𝘰 𝘵𝘩𝘪𝘴 𝘧𝘪𝘷𝘦 𝘺𝘦𝘢𝘳𝘴 𝘢𝘨𝘰... 𝘪𝘵'𝘴 𝘵𝘩𝘳𝘪𝘭𝘭𝘪𝘯𝘨." — Chris Vallone

𝗦𝗵𝗼𝘄 𝗢𝘃𝗲𝗿𝘃𝗶𝗲𝘄

This week, hosts 𝗞𝘆𝗹𝗲 𝗦𝗵𝗮𝗻𝗻𝗼𝗻 (𝗧𝗵𝗲 𝗔𝗜 𝗦𝗮𝗹𝗼𝗻) and 𝗔𝗻𝗻𝗲 𝗠𝘂𝗿𝗽𝗵𝘆 (𝗦𝗵𝗲 𝗟𝗲𝗮𝗱𝘀 𝗔𝗜) start with an honest check-in: the difference between “being busy” and having a practice you can return to—especially when you’re stressed, avoiding something annoying, or stuck in that not-knowing feeling. From there, the conversation widens into what people actually 𝘣𝘶𝘺 when they buy “AI” (and what they don’t), why one-and-done training often falls short, and how community can be the difference between quitting and getting traction.

Then 𝗖𝗵𝗿𝗶𝘀 𝗩𝗮𝗹𝗹𝗼𝗻𝗲 joins to talk about a massive shift in independent film: what happens when your biggest constraint isn’t budget anymore. Chris walks through his creative process, how he works with writing tools without handing over the wheel, what film festival reactions have been like, and why newcomers who ignore these tools may be putting themselves at a disadvantage.

𝗞𝗲𝘆 𝗧𝗮𝗸𝗲𝗮𝘄𝗮𝘆𝘀

• 𝗣𝗿𝗮𝗰𝘁𝗶𝗰𝗲 𝗯𝗲𝗮𝘁𝘀 𝗺𝗼𝘁𝗶𝘃𝗮𝘁𝗶𝗼𝗻. A steady approach helps you work even when you don’t feel like it—and helps you tolerate the “I don’t know how” moment without spiraling.

• 𝗦𝘁𝗮𝗿𝘁 𝘄𝗶𝘁𝗵 𝘄𝗵𝗮𝘁 𝘆𝗼𝘂’𝗿𝗲 𝘁𝗿𝘆𝗶𝗻𝗴 𝘁𝗼 𝗱𝗼 𝗮𝘀 𝗮 𝗵𝘂𝗺𝗮𝗻. Tool-hunting is a trap if you haven’t named your goal.

• 𝗙𝗼𝘂𝗿 𝘂𝘀𝗲𝗳𝘂𝗹 𝗺𝗼𝗱𝗲𝘀 𝗳𝗼𝗿 𝗹𝗲𝗮𝗿𝗻𝗶𝗻𝗴: reflect (how am I showing up?), get curious (play and explore), build (apply), and serve (share, ask, support).

• 𝗖𝗼𝗺𝗺𝘂𝗻𝗶𝘁𝘆 𝗶𝘀 𝗮 𝗳𝗼𝗿𝗰𝗲 𝗺𝘂𝗹𝘁𝗶𝗽𝗹𝗶𝗲𝗿. You don’t have to quietly struggle through every stuck point—especially when tiny settings and small choices can change everything.

• 𝗙𝗶𝗹𝗺 𝗶𝘀 𝗮 𝗰𝗹𝗲𝗮𝗿 𝗲𝘅𝗮𝗺𝗽𝗹𝗲 𝗼𝗳 𝘄𝗵𝗮𝘁’𝘀 𝗰𝗵𝗮𝗻𝗴𝗶𝗻𝗴 𝗳𝗮𝘀𝘁. Chris explains how today’s tools can shrink costs for scenes that used to require huge crews, coordination, and cash—while still demanding taste, direction, and craft.

𝗢𝘂𝗿 𝗚𝘂𝗲𝘀𝘁

𝗖𝗵𝗿𝗶𝘀 𝗩𝗮𝗹𝗹𝗼𝗻𝗲 is a longtime filmmaker and artist (and also a vintage VW Beetle restorer) who’s bringing scripts he wrote years ago to the screen using today’s video tools. From MiniDV-era, shoestring sets to AI-assisted storyboards and trailers, Chris shares what’s gained, what’s lost, and what still matters most when you’re trying to tell a great story.

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.