The Real Secret Behind Consistent Content: Storytelling, AI & My Big Mishap

Summary

Episode Summary: The Real Secret Behind Consistent Content—Storytelling, AI & My Big Mishap

Podcast: Retail Media Breakfast Club
Host: Kiri Masters
Date: April 21, 2026
Guests: Austin Leonard & Elizabeth Donovan (from the "Unlocked" podcast)
Episode Length: ~11 minutes

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Overview

This episode features highlights from Kiri Masters’ guest appearance on the "Unlocked" podcast with Austin Leonard and Elizabeth Donovan, focusing on the creative process behind consistent content in retail media. Kiri delves into her routines, the critical role of storytelling, the use of AI tools, and ends with a candid, humorous mishap from her early days in the industry. The discussion balances practical insight with personal anecdotes, offering actionable takeaways for anyone producing content in retail media.

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Key Discussion Points & Insights

The Pressure and Motivation to Create Consistent Content

• Stamina for Content Creation:
  • Austin expresses amazement at Kiri’s consistency and stamina for daily storytelling, setting the tone for the conversation.
    • Quote: “How does she do it? This is incredible to have the stamina and it’s not easy to come up with this type of storytelling every single day.” (01:29 – Austin Leonard)
• Kiri’s Process:
  • Kiri emphasizes that it’s her full-time job, and while sometimes she plans ahead, other times, she’s drafting on tight deadlines.
    • Quote: “Sometimes I have content planned out for a week, sometimes it’s three o'clock in the afternoon and I’m like, I need a newsletter for tomorrow. What am I going to write about?” (01:52 – Kiri Masters)
  • There’s never a shortage of topics; the challenge is prioritizing which stories to tell next.

Storytelling as a Tool for Engagement

• The Power of Personal Anecdotes:
  • Kiri stresses integrating personal stories to make content memorable and relatable.
    • Quote: “I love to use personal anecdotes and stories whenever I can to make a point. And people seem to really love it.” (03:46 – Kiri Masters)
  • She references feedback from her audience—people recall specific stories, like her “baby Chino” anecdote.
• Story Worthy & Homework for Life:
  • Inspired by Matthew Dicks’ Storyworthy, Kiri adopted “Homework for Life”—writing a daily snapshot of something that happened, storing stories in Notion for future use.
    • Quote: “Some of the most powerful stories that we have is not about going on this amazing vacation…it’s about the conversation that you had with your kid or about the dog running away…” (04:39 – Kiri Masters)
  • This practice sustains her storytelling pipeline and encourages fun, connection, and creativity, even in a serious industry.

The Role of AI in Content Creation

• Tools of the Trade:
  • Kiri shares specific platforms she uses:
    • Claude: For writing and as a collaborative partner
    • Claude Cowork: For automating tasks
    • ChatGPT: Frequent use for ideation and drafting
    • Notion: For cataloging content, interview notes, and research
  • She acknowledges feeling overwhelmed by the pace of automation but encourages others not to stress about being behind.
    • Quote: “Don’t worry if you’re feeling behind on it. That’s certainly how I feel.” (03:31 – Kiri Masters)
• AI as Creative Partner:
  • Elizabeth imagines AI as a second brain and emphasizes the importance of using AI as an assistant, not a replacement for authentic storytelling.
    • Quote: “You have to be able to tell that story that creates that human connection that you’re talking about.” (06:39 – Elizabeth Donovan)

Why Storytelling Matters in Retail Media

• Differentiation and Human Connection:
  • The panel agrees: Storytelling sets apart brands and builds memorable, relatable content—vital for sales and team growth.
    • Quote: “Creates the strong relationships. It creates the ability for you to land a highly technical point because you can relate it back to something that they probably have experienced in their life too.” (06:56 – Elizabeth Donovan)
• Fun as a Value:
  • More fun leads to more engaging content and a stronger, more connected community within retail media.

Kiri’s Big Mishap: The Instacart Domain Incident

• The Story:
  • Kiri recounts registering “instacartforcmos.com” as part of writing her book, Instacart for CMOs, with a colleague.
  • She then received a legal takedown notice from Instacart, who believed she was improperly using their trademark, resulting in arbitration and the loss of the domain.
    • Quote: “I just wrote a book to tell everyone how great Instacart is. And, you know, no good deed goes unpunished.” (09:47 – Kiri Masters)
  • The story exemplifies the unexpected “hijinks” that come with content entrepreneurship.

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Notable Quotes and Memorable Moments

• Consistency and Commitment:

  • “Sometimes it’s three o’clock in the afternoon and I’m like, I need a newsletter for tomorrow. What am I going to write about?” (01:52 – Kiri Masters)

• On AI and Feeling Behind:

  • “Don’t worry if you’re feeling behind on [automation]. That’s certainly how I feel.” (03:31 – Kiri Masters)

• Storytelling Wisdom:

  • “Some of the most powerful stories that we have is not about going on this amazing vacation … it’s about the conversation that you had with your kid or about the dog running away or something like that.” (04:39 – Kiri Masters)

• On the Instacart Mishap:

  • “I just wrote a book to tell everyone how great Instacart is. And, you know, no good deed goes unpunished.” (09:47 – Kiri Masters)

• The Value of Storytelling in Sales:

  • “You have to be able to tell that story that creates that human connection … It’s definitely something that I hope people don’t underinvest in.” (06:39 – Elizabeth Donovan)

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Timestamps of Important Segments

• [01:29] – Austin introduces the challenge and admiration for Kiri’s content creation
• [01:49] – Kiri describes her daily process and pressure to deliver
• [03:08] – Discussion of AI tools (Claude, ChatGPT, Notion) and their role in writing
• [03:46] – Importance of personal anecdotes and the “baby Chino” story feedback
• [04:21] – Introduction of Storyworthy and “Homework for Life”
• [06:03 – 06:39] – AI as a second brain and storytelling’s business impact
• [07:59] – Kiri shares the Instacart legal mishap story
• [09:47] – Reflecting on the “no good deed goes unpunished” lesson

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Takeaways

• Storytelling, combined with technology, remains at the heart of impactful content in retail media.
• AI can support, but not replace, the authentic, human stories that engage and educate audiences.
• The best stories often come from everyday mishaps and relatable moments.
• Building an archive of stories, even simple daily events, is a powerful tool for any content creator.
• Legal missteps can happen in content creation—sometimes even with the best of intentions!

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For more, check out the full “Unlocked” podcast episode linked in the show notes.

Transcript

[Host]

I was recently a guest on one of my favorite retail media podcasts, Unlocked with Austin and Elizabeth. And this is one of my favorite podcasts because it is all about the career stories and personal POVs of notable people in the retail media industry. It is more candid and more personal than a lot of the very excellent but quite tactical or nitty gritty oriented

[Guest]

podcasts that are out there.

[Host]

So I was very flattered to be

[Guest]

asked on the show.

[Host]

And I talk a little bit about the origin story of Retail media Breakfast Club, what I was doing before all of this, some of my routines around content, things like that. But what I wanted to share with you on this little snippet from that conversation is a little bit more of my process as a writer. And, and this is something that I feel a lot of people could tap into to lean into storytelling. Austin has a really great perspective on this as well, which he shares after I give my little spiel. And to end with, I do share a kind of embarrassing but quite funny story from a few years ago that I've never shared publicly. I think you're going to like it. I do highly recommend checking out the the Unlocked podcast with Austin and Elizabeth. Now let's listen to some highlights.

[Austin Leonard]

Thank you for writing and continuing to educate our industry because I know when we first met about a year ago and I started to read your content, I'm like, how does she do it? This is incredible to have the stamina and it's not easy to come up with this type of storytelling every single day.

[Guest]

Well, thank you for saying that. I get that comment quite a bit. I'll say what I. What I usually tell people is one, it's my job. I don't have busy jobs like you guys. This is all I do. I sit at my desk and sometimes I have content planned out for a week, sometimes it's three o' clock in the afternoon and I'm like, I need a newsletter for tomorrow. What am I going to write about? And I just have to sit there and write the damn thing and then record the podcast. That. That's the thing. Second is, do you guys ever feel bored or like you've run out of challenges to solve in your jobs?

[Elizabeth Donovan]

No.

[Austin Leonard]

I don't know what boredom is. Probably because I'm a mother of two girls and.

[Guest]

Yes, well, there's.

[Austin Leonard]

I'm a chauffeur.

[Guest]

Yeah, right. Well, there's that too. But like, there is just so much to talk about. There is, there is a. I've got a list of. There's A hundred things that I want to get to and things that are kind of percolating and never run out of things to talk about. It's my job, it's what I do. And because I've done it for a while, I've become a bit more quick at doing it. And AI certainly helps. I use it all the time. It's an incredible tool. I wouldn't be able to have the same level of output as I do.

[Austin Leonard]

But yeah, you're the first one to bring up AI in our conversations and I know that's a little bit off topic, but would you share with our listeners a few of the platforms that they should look into?

[Guest]

Yeah, for me it might not be the same for everyone in the audience, but I use Claude for writing. It's a bit of better writing partner. I've started to use Claude cowork as well to actually automate some tasks solid. And I just, I feel hopelessly behind on all of this stuff on automation because it takes a while to actually learn it and set it up. So don't worry if you're feeling behind on it. That's certainly how I feel. I use ChatGPT a lot and then I also, I use Notion to store and catalog all of my content that I've written. All of my interview notes. Save a lot of research there. And one thing that I'm not sure if you guys have noticed it, I don't do it all the time. I really making more of an effort to do it. But I love to use personal anecdotes and stories whenever I can to make a point. And people seem to really love it. I've had people come up to me at events and say, oh my gosh, I love the baby Chino story. Which was like an opening of a story. It was like a story about my son and I love doing that. There was a book that I read a few years ago called Story Worthy and it was written by this guy who is, you know the Moth, the storytelling competition. The Moth, yes.

[Austin Leonard]

It's.

[Guest]

Yeah. So it's like a stand up storytelling. It's not meant to be humorous, but it's like people's personal stories and it's a storytelling competition. It's amazing. So this guy who's a champion Moth contestant, he wrote a book about storytelling and how to effectively tell stories. And he's got a concept in this book called Homework for Life. And it's basically every day you write, just write a quick snapshot of something that happened. It could be from that day. It could be a memory from years ago and just start documenting things that happen. It doesn't need to be anything significant. Some of the most powerful stories that we have is not about going on this amazing vacation or hiking the Camino Trail. It's about the conversation that you had with your kid or about the dog running away or something like that. So I started doing that. I write, write things down, extract it, and get it into my notion database. And then I use AI tools to see. I'll write an article on, like, how. Which story can I use as an opener for this? And sometimes a link will be a little bit tenuous, but that's something that I've really started to enjoy, is. Is bringing more of that storytelling in. And it's fun. I think we could all have a lot more fun in this industry. We do not need to be so serious.

[Elizabeth Donovan]

I don't know.

[Austin Leonard]

I'm having a lot of fun.

[Elizabeth Donovan]

Yeah, that's. That's part of why I think that this. All this content works too, is because there is a very engaged group, and we do like to have fun. We all work really hard, but we also, you know, we. We genuinely like talking about this stuff too. We can learn about it all day if they'll let us.

[Guest]

Yeah.

[Elizabeth Donovan]

I do have this image of you sitting there in front of your computer talking to the AI and writing back and forth to the AI because you're like, I couldn't get in on the phone today, so this is who I get to talk to. Here are all my stories. But it feels like it's almost like a second brain and a little bit of an assistant slash editor that's helping you stay organized even when you didn't realize that you were organized. Making those connections is really key. The storytelling aspect, though, is right on. And I think that's definitely throughout people's sales careers that if they haven't gotten the message around, you have to be able to tell a great story that helps differentiate your brand, your product, your team, whatever it is that you have to do. It's. It's definitely something that I hope people don't underinvest in the development of those skills just because there's easier AI tools that can help you spit out content, but you have to be able to tell that story that's. Creates that human connection that you're talking about. So.

[Austin Leonard]

Yeah, and they remember.

[Elizabeth Donovan]

And they remember. Of course they do. Yeah. Creates the strong relationships. It creates the. The ability for you to land a highly technical point because you can relate it back to something that they probably have experienced in their life too.

[Host]

Miracle Ads is the only retail media solution designed for both 1P and 3Pmarketplace brands. Why does that matter? Marketplace sellers demand a seamless advertiser experience that still offers full funnel ad formats. And retailers need a flexible solution that allows you to scale your media business. Learn [e-mail] that's M I R A K L.com and then in the interview, Austin and Elizabeth asked me about how I first got got into the retail media game. And this actually presented a perfect opportunity to tell a story that I've never actually told publicly before, that I think you're going to get a real kick out of.

[Guest]

Instacart launched their self serve ad platform and they just came out of the gate with something that was accessible, it was smart, it was really well thought out and it really made me think about this whole ecosystem outside of just the big behemoth in the room. So that was really the moment. So actually I partnered up with one of my colleagues at Bobsled Marketing, that was the name of my agency, one of our ad advertising leaders, Stefan. And we, we started writing a book about Instacart. It was called Instacart for CMOs. And because I wanted to get into this, Instacart's very interesting because it's a four sided marketplace. You've got the brands, you've got the advertisers, you've got the retailers and then you've got all the, also the shoppers in the stores as well. And that they're kind of like, they have a little bit of a choice in what product gets picked off the shelf as well. So it's just something new that I wanted to unpack and really understand. And so we interviewed a bunch of people. I spoke with some really great investment like equity analysts about Instacart and registered the domain Instacart for CMOs. And one day I get a text from, from my assistant saying there's something that you need to look at quite urgently. And it was a takedown notice from Instacart's legal team about this domain that I had registered Instacart for CMOs. And because I hadn't actually launched the book yet, it was just kind of like a holding page while I was getting everything ready. They thought that I was some personator, someone sort of like using their trademark as a bad actor. That was, that was in their claim. So they, they actually made me give up my domain instacart for cmos.com and I was Actually, just. I was preparing for this. I was just looking at this like it went to arbitration and everything. I was like, look, I just wrote a book to tell everyone how great Instacart is. And, you know, no good deed goes unpunished. So that's the kind of hijinks you get into when you're trying to get into the content marketing game.

[Elizabeth Donovan]

That's so funny. And obviously that for CMOs, it was really around, like, hey, this is a real media opportunity, real marketing opportunities. You need to understand it. And someone in the legal team was like, nope, we're just going to shut that down. By the way, I'll save everyone the trouble. I just tried to navigate to it. It is still shut down. So apparently. Apparently.

[Guest]

No, they own it. Instacart owns it now. Because

[Elizabeth Donovan]

Page, though.

[Guest]

No, of course not.

[Elizabeth Donovan]

All right, we'll have to call some of our friends. We'll have to call some of our friends over there.

[Guest]

That book, it's really funny. Like, the only people that. That buy that book are people who are interviewing for jobs at Instacart,

[Elizabeth Donovan]

which is not a small number, so.

[Guest]

Well, I guess so. It's a few years old now.

[Host]

Yeah.

[Guest]

Anyway, I wanted to tell you guys a story that I hadn't told publicly. So there you go. Well, that is it for today.

[Host]

I hope you enjoyed this little snippet.

[Guest]

Snippet.

[Host]

From that episode that I did with Austin Leonard and Elizabeth Donovan from the Unlocked podcast. We'll link up to it in the show notes. Thanks for listening and I'll catch you tomorrow.