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Index/Startups & Founders/The Longer Game
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Season 4 Episode 8: Freedom To Fail

The Longer Game · 2026-05-29 · 37 min

0:00--:--

Key moments - from our scoring

Substance score

59 / 100

Five dimensions, 20 points each

Insight Density11 / 20
Originality10 / 20
Guest Caliber14 / 20
Specificity & Evidence12 / 20
Conversational Craft12 / 20

Backstroke uses generative AI to automate email campaign creation for e-commerce retailers, handling roughly 70% of routine campaigns while preserving the human touch for tent-pole moments like CEO letters or product launches. RJ brings 20+ years of digital marketing experience from his time leading email and marketing teams at Exact Target (acquired by Salesforce Marketing Cloud) and his previous AI startup Pattern89 (sold to Shutterstock in 2021). The conversation explores a deeper challenge than technology itself: organizational structures and leadership mindsets that block AI adoption. Michael and RJ discuss how fear of failure, tied to identity and survival instincts, creates corporate committees and bureaucracies that slow implementation. They examine the gap between stated AI goals and actual execution - many retailers create AI committees without clear metrics or decision-making authority, turning what could be accelerants into blockers. The episode challenges the narrative that AI will simply eliminate jobs, instead arguing that leadership must create space for teams to experiment, fail, and learn new tools like Claude without losing productivity targets.

Key takeaways

  • →Email marketing comprises 20-40% of e-commerce revenue, and Backstroke automates 70% of routine campaigns while preserving human judgment for critical moments like founder communications.
  • →Most retail organizations create AI committees and innovation teams without clear decision-making criteria or authority, inadvertently becoming blockers rather than accelerants to technology adoption.
  • →The real problem isn't AI capability but organizational fear of failure, rooted in human survival instincts that make teams avoid risk even when change is necessary.
  • →Successful AI adoption requires leaders to reduce daily revenue targets and sales goals temporarily to give teams permission to learn new tools without performance pressure.
  • →People hired into new leadership roles are most likely to implement AI change because they lack organizational inertia, while tenured employees face institutional resistance to trying new approaches.

Guests

RJ Taliar

Topics in this episode

generative AIEmail marketing automationCRM managementSalesforce Marketing CloudExact TargetShutterstockBackstrokePattern89predictive AI algorithmsretail marketing

Questions this episode answers

What percentage of e-commerce revenue does email marketing typically represent?

Email marketing makes up 20-40% of revenue for e-commerce and retail brands, making it a critical lever for business performance.

How does Backstroke handle the difference between routine and strategic email campaigns?

Backstroke handles approximately 70% of routine promotional campaigns, but the remaining 30% - such as new product launches, letters from the CEO, and other tent-pole moments - require human creativity and judgment.

Why do retail organizations struggle to adopt AI even when they understand its benefits?

Most retailers create AI committees without clear decision-making authority or criteria, and leaders avoid giving teams permission to slow down and learn new tools because they're unwilling to temporarily sacrifice revenue targets.

What advantage do newly hired leaders have in implementing AI at retailers?

New leaders haven't yet adopted the organizational status quo and inertia, making them more willing to reshape tech stacks and processes to implement change faster than tenured executives.

How does human psychology explain resistance to AI adoption in corporate settings?

Fear of failure is tied to identity and survival instincts - people avoid risk at high costs because failing publicly can result in being fired or ostracized from the group.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

11 / 20

The episode contains some substantive insights about AI adoption barriers in retail (committees as blockers, failure aversion, leadership challenges) and the need for human creativity alongside AI, but much of the 37 minutes is devoted to tangential philosophical discussion about entrepreneurship, failure, running, and personal development that, while coherent, doesn't directly educate B2B operators on the core topic. Valuable insights are diluted by meandering conversations.

they don't have like key... they're probably like, there's probably an exception where there's one that's like an accelerant, but most times what I hear from brands are like, I'd love to use this, but the new AI committee has to review all AI things
When I first pitched Backstroke, people, like leaders on the team, they're like, don't worry, no one's job's going away... And then about six months ago, I started hearing people say, aren't gonna backfill people because we think we can do things better with AI

Originality

10 / 20

The observation about AI committees functioning as unintentional blockers is useful, but most of the framing relies on familiar tropes: AI replacing jobs, the need for upskilling, failure being essential for growth, and creativity as the human differentiator. The conversation about scarcity vs. abundance mindset and drawing parallels between creative writing iteration and entrepreneurship are recycled concepts. RJ does offer specific CRM metrics tracking example, but the broader narrative lacks fresh angles.

Everybody goes to like AI is going to ruin us all, kill us all, take all of our jobs
You know, it's like iteration. And, you know, that's that's the entrepreneurial journey. That's the AI thing. That's like building new tech

Guest Caliber

14 / 20

RJ Talier is a legitimate operator with meaningful credentials: 10 years leading email/marketing at Exact Target/Salesforce, founded and sold Pattern89 to Shutterstock (predictive AI for social media), and currently runs Backstroke. He has boots-on-the-ground experience selling AI solutions to retailers and observing real adoption friction. However, the episode is hosted/co-hosted with Michael Maher (agency owner), making this less of a typical guest interview and more of a peer conversation, which dilutes the single-expert voice advantage.

I got my start in digital marketing about 20 something years ago when I was an early employee at Exact Target, which got acquired by Salesforce as part of the Salesforce Marketing Cloud. So I led the email and teams for 10 years there
I sold that business to Shutterstock in 2021. And then I started working on Backstroke

Specificity & Evidence

12 / 20

The episode includes some concrete details: Backstroke handles 70% of campaigns, email marketing represents 20-40% of e-comm revenue, a one-year deal cycle example, Pattern89 worked with Williams Sonoma and Facebook, and a CRM VP tracking hours saved via AI queries. However, these specifics are sparse and scattered. Most claims about AI adoption barriers, corporate inertia, and employee displacement remain anecdotal without supporting metrics, customer counts, or quantified impact data. The conversation largely operates at the conceptual level.

email marketing is the bread and butter a lot of digital marketing strategies, making up 20 to 40 % of revenue for e-comm and retail brands
we can do 70 % of your campaigns, but 30 % of them are like those tent pole moments, new product introductions, letter from the CEO

Conversational Craft

12 / 20

Michael Maher asks reasonable follow-ups (e.g., "Is it a scarcity versus abundance mindset?", "Do you think maybe in some cases these committees... are created an intentional blocker?") and pushes back on soft claims. However, he frequently allows the conversation to drift into personal anecdotes (his degree, running, faith, bourbon birthday gifts) that reduce focus on substance. He doesn't press RJ on specifics (e.g., how many retailers is Backstroke actually working with, what's the adoption rate post-implementation, why exactly are committees blockers vs. what should replace them). The interview becomes a philosophical chat rather than a rigorous exploration.

So when you say that, that makes me feel like there's not an AI problem. Maybe there's a leadership problem
And once you have a use case and you know what you want to do for it, then fine. How do you, how do you integrate this and what's the end goal that you're looking for?

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Most-used words

michael69maher68talyor67backstroke21back14learn14fail14failure10retailers9marketing9degree9point9different9saying9real8part8

Episode notes

Humans have a tendency to shy away from failure, and for good reason. It hurts. It could cost us our jobs. But what if on the other side of that failure lived an innovation that drove amazing change? Maybe we'd think about failure differently. We think so. R.J. Talyor, CEO & Founder of Backstroke, joins us on this episode to talk about his favorite subject: failure. "Whatever you can do, or dream you can, begin it. Boldness has genius, power and magic in it." - Johann Wolfgang von Goethe. Walt Disney also said, "If you can dream it, you can do it." The current economy surrounding AI has a lot of hype but also a lot of potential. There is this potential for us to leverage AI to allow us to be more human, yet we tend to focus on the dark side where humans are no longer needed. Sure, change is coming. People will lose jobs or remain out of work because of AI tech implementation. But could there be more that lives on the other side of that? We think so. Grab your goggles and swim cap and let's dive right into it. What they cover AI has evolved dramatically from the 1950s to where we are now in the world of generative AI. It's enabled us to do things better & faster.

Full transcript

37 min

Transcribed and scored by The B2B Podcast Index.

Michael Maher: Hey everybody, welcome to the longer game podcast that talks all about retail we bring you the real deal. We bring you people that are operators that have done the work that are not just sitting down on high and pointing fingers and telling you in theory what looks good or what should be done. We've got real hardworking folks coming on this show and on the show we have RJ Talier. He is the CEO and co-founder of Backstroke.

I'm going to let him tell you more about what he does, a little bit about himself. to the show, RJ. R.J.

Talyor: Hey, thank you. really appreciate the opportunity to so I'm RJ, I'm the CEO and founder of Backstroke and our company predictive ⁓ and on-brand campaigns retailers. I got my start in digital marketing about 20 something years ago when I was an early employee at Exact Target, which got acquired by Salesforce as part of the Salesforce Marketing Cloud. So I led the email and teams for 10 years there at traveled all over the world, working with retailers, literally every brand ⁓ you heard of.

It was an awesome job for somebody who was 24. ⁓ Michael Maher: ⁓ my gosh, you probably learned so much during that time. R.J.

Talyor: You know, I have an English degree ⁓ I got this job at Exact Target ⁓ because had a friend who worked there and ⁓ they growing really quickly and she was like, you should apply. So I did. And then I really didn't know what I was getting myself into. And I thought, I'm going to go to grad school in six months, whatever.

I'll just do this job for a little bit. And then I worked there for 10 years and I built my whole career. Michael Maher: That's amazing. R.

J. Talyor: You know, so it's, it was, you know, email was just coming out in 2000 or, know, it was out, but like can spam had just been passed in 2003. And so, or 2004. And so it was like early days.

And, yeah. So then I built my career in digital marketing and I, I left Salesforce. I went to another startup for about a year and a half. And then I started my first company, which was called pattern 89.

it was early AI startup that predicted what you would click on, on Instagram or Facebook. Michael Maher: Interesting. R.J.

Talyor: And we worked with brands like Williams Sonoma, actually Facebook was a customer and a bunch of Accenture customers. And then we sold that business to Shutterstock in 2021. And then I started working on Backstroke. So I've been in like AI world since 2016 when we called it AI, but it really wasn't AI, we were in the early days of AI and people would debate about machine learning versus.

Michael Maher: Okay. R.J. Talyor: data science versus the AI.

And now we're like in the deep part of AI with Backstroke. ⁓ Michael Maher: mean, AI has been around since the 60s, right? 50s, 60s, mean, it's been around for a long time, and there's been this crazy quick evolution over the past couple years. And it sounds like what you were doing was maybe, when people were calling it AI, maybe it really was more machine learning, but algorithm-based stuff.

R.J. Talyor: Yes. Yes.

Yes. Yeah. Yeah. Yeah.

I mean, it was like algorithms. So, but it was kind of crazy because back in 2016, back ⁓ to years ago, ⁓ when would say AI in all of our marketing materials, it said AI parentheses, artificial intelligence. And so would be like, we'd have to explain what we meant by AI. And I would do all this, like, what is AI?

you know, ⁓ conversations and, try translate what our data scientists were doing to regular folk and I'm a regular folk in this world trying to explain it. And now we talk about AI and like, you know, in, in like all of the extreme ways and everybody's talking about AI, this AI, everything, but it's funny because Michael Maher: People don't question it now. You don't need the parentheses. R.

J. Talyor: Right. Yes. Yeah.

Yeah. I mean, you know, in chat, TBT did that work for all of us. ⁓ So, ⁓ and that was what, you three or four years ago. It's kind of wild.

Michael Maher: That's crazy. It almost feels like it was like six months or a year ago when OpenAI came out with this huge announcement. I always jokingly say Al, because AI kind of looks like Al. But I don't think people like, I don't know how many people think it's funny.

I'm glad you're laughing. I'm like, who is Al? Can somebody tell me who Al is? I have no idea.

It keeps showing up in every conversation that I have. This is ridiculous. R.J.

Talyor: Yeah. Yeah. That's funny. That's good.

That's good. You know, my father-in-law's name's Al and I'm thinking, ⁓ Yeah. Yeah. Yeah.

Michael Maher: Oh, there you go. Is he real? That is the real question. Tell us at Backstroke, what's that evolution of AI for you now?

R.J. Talyor: Yeah. Well, you know, with, with backstroke, what we're doing is taking a lot of the point and click, the manual labor out of creating email marketing campaigns for retailers.

marketing is the bread and butter a lot of digital marketing strategies, making up 20 to 40 % of revenue for e-comm and retail brands. And, marketers a lot of time designers, CRM managers, digital marketing people. ⁓ They just, life, their, their daily grind is like. Michael Maher: Okay.

R.J. Talyor: uploading images, creating emails, testing them, et cetera. it's so formulaic and patterns emerge.

And so what Backstroke does is generates those emails for them and predicts what's going to perform. not only is generative and powered by AI algorithms, but it's it's predicted to perform for each subscriber on the list. So it does that work better, also faster and generates more revenue. So.

It's not for all the campaigns. One thing I would urge here is I say backstrokes like a 70, 30, we can do 70 % of your campaigns, but 30 % of them are like those tent pole moments, new product introductions, letter from the CEO, really important ones that I think require a human touch. But a lot of the promotions, those types of things can be done by backstroke pretty easily. Michael Maher: You mentioned to me that you have a master's in creative writing, right?

OK, which I love. have a fine degree that does not translate to the work that I do as an entrepreneur and marketing advertising agency owner at Cartology. My degree in college was Asian studies. And I that degree because I had the most credits to graduate with that.

⁓ And I to get the hell out of college. R.J. Talyor: Yes, yeah.

So, here you go. Yeah. Michael Maher: I had taken Japanese for like in high school, college, and I was just like, what can I get out of here with? And I was good at learning, but I didn't like being told what to learn.

And I wanted to cut my teeth on stuff my own way, which, know, now I'm an entrepreneur, been an entrepreneur for the past 16 years. Love it, enjoy it, and still an entrepreneur for different reasons than why I started. You know, a lot of people think about freedom and other things like that. But when you're really an entrepreneur, you are R.

J. Talyor: Yeah. Michael Maher: in service to the goal of whatever company or thing that you're building. And yes, there is freedom.

And maybe that's part of it. But it's like there's also an extreme responsibility to get these things done. And so there are often, would say, you're working harder or longer, depending upon in certain seasons to get there. I have a finance degree as well was my point with that story.

in this creative writing, R.J. Talyor: Yeah. Yes.

Yeah. Hmm. Yeah. Michael Maher: know, degree that you have.

That's a very, that's, I would say, an art, you know, and there is this conversation maybe that's happening of like, what is art if AI is doing it? And I've heard some really cool, like AI generated songs, but it's not really the artist. And people are saying that like, we're going to get to a point where it's indistinguishable. But I think at that point, R.

J. Talyor: Yeah. Michael Maher: People are just like we have to have sponsored on our listings Amazon or any advertisement has to say sponsored or someone is an influencer. That got regulated.

It's probably going to get to a point where it's AI generated. I people from an art perspective, and I could be really wrong. I have been before. But we're going to want the human touch.

The letter from the founder, by the way, I said you were a co-founder. You're only a co-founder with yourself. I now realize that you're just a founder. You're like a Michael Scott and Jim Halpert co-managers.

That's what that always makes me. R.J. Talyor: To be fair, I do have co-founders.

one of them is my wife. so I mean, we're right? So we're. Michael Maher: Yeah, exactly.

That's right. I was having a conversation with my wife, I don't know, a week or so ago. And she's like, my like co CEO advice is this. And she's got an amazing corporate job, but she's also very wise and smart.

And so I get to, you know, bounce stuff off her dinner. But this art conversation is like, people are going to want, I think, a human touch. And it feels like people just run to the extremes of AI is going to replace everything is going to replace all these people. R.

J. Talyor: Yeah. Michael Maher: And I think there will be jobs that go out of style or that get depleted because of AI. And there's still going to be a need for human touch.

And there's going to be new jobs that are created that require humans based on this new technology. And at the end of the day, I really believe that God created us to be in community and like that's how we're designed. We need interactions with each other. And I think if you look at the statistics people have like gotten smartphones and become more isolated and more focused on social media.

R.J. Talyor: Mm-hmm. Yeah.

Michael Maher: We are more depressed. Suicide rates increased. That is not good or healthy. That was a bunch of stuff that I just dumped on you.

when hear you have this, you're working in AI, but you have this ⁓ writing degree, those things can feel like it odds. ⁓ think they're just different. R.J.

Talyor: Yeah. Yeah. Yes. Yeah.

Yeah. Yeah. Yeah. man, you did hit with a lot there because they're, they're.

⁓ No, it's such a broader conversation. know, first off, everybody goes to like AI is going to ruin us all, kill us all, ⁓ take all of our jobs. I don't, I don't that. I think that that's a alarmist and extremist headline that gets clicks or something like that.

I think that just with any evolution of technology or Michael Maher: I'm really sorry. Great. R.J.

Talyor: advancement, there's change. And I think that, you know, like, you my father-in-law worked at Ford for 35 years and drove And as all these machines came in, he had to learn how to use the machines, you know? ⁓ But how you look at somebody like my former father-in-law and say, AI is going take your job. You just need to re-skill or learn, you know, that's a really hard lesson or that's a really hard thing to Michael Maher: Mm.

R.J. Talyor: shut down someone's throat who has been successful in building a career for 30 years. And I think the same thing's happening in a lot of white collar jobs where we're saying, hey, AI is now a tool that allows you to all of these things.

Your job just got bigger, ⁓ All you need to do is just learn how to use Claude and actually just learn as you go. Because no saying stop what you're doing, learn Claude for the week because it just got updated and a new model just came out. ⁓ Michael Maher: That's scarier for, I enjoy that. Because I'm like, let's get in, let's dive in and figure it out.

But most people, I think that scares them. R.J. Talyor: Yeah.

Yeah, well, I mean, you like we're talking about retailers, like all the retailers we work with are trying to like get just get their job done, get the email out, get the site updated, get the, and now, now we walk in the door and we're like, Hey, here's some AI tools that like, you know, mostly work, but like it might give you some weird stuff and six fingers, but like just learn to do as you go. It's real easy. And they're like, listen, had zero time to do anything new. And then you just added this to my plate.

Michael Maher: Right. R.J. Talyor: and somebody just went on maternity leave or they're not back filling that role because they said AI can do it.

there is like a real, there is change, right? There's change. And I think we're. Michael Maher: Yeah.

Is it a scarcity versus abundance mindset? Is that kind of what we're looking at? Because the scarcity is not enough jobs, AI is going to take them. The abundance mindset, and the abundance mindset, it doesn't mean that scarcity is a real thing.

But what is the abundance mindset is what the human perspective can look at is, all right, what's beyond this? And how do we plan for something like that? Which is not something that I think AI really can. R.

J. Talyor: Yeah. Mm-hmm. Yes.

Michael Maher: can work in the here and now and it can develop and it can grow and learn, but what is beyond this? R.J. Talyor: Yeah.

Yeah. well, mean, truly what's, what's beyond ⁓ of this is creativity again. It's like, it, it, it, it's, it's like hard to imagine, right? Like somebody has wisely said like, you know, whatever you can imagine that we can do, we can actually do.

So like, what are we not imagining yet? Because we're so constrained by the circuit, the current capabilities and the current, you mindset, like the, know, that You know, we're recording when Artemis 2 is out there, right? It's pretty amazing. You know, they've gone further than anybody's gone in whole world.

know, humans Mars and stuff, like what's something that we haven't imagined yet because that will be enabled because some of these mundane tasks that we complain about or ⁓ the that take our time today can accomplished with AI. I think that's cool. So more creativity, ⁓ more advancement, opportunity. ⁓ I think Yeah.

Michael Maher: So like humans being more human. OK. That is how my agency I've about implementing AI technology is how I take the sucky mundane things that people don't want to do that technology could do well in a repetitive and more accurate manner because it can find maybe better. got, you know, it can run a data set and R.

J. Talyor: So. Michael Maher: query stuff faster than you can create a pivot table or whatever. that would be a cool competition to have of like, who can create a pivot table or formulas faster inside of Excel and have like race.

the advantage here ⁓ and we approach is, what can I take off the plates of my humans so that they can do more of the cool, fun thing, things that they want to do? The problem in that to your point about like, yeah, just learn, cod as you go. It's not going to be a big deal. When you want to take on a new skill set, it very often feels like slowing down.

And if you've got all this stuff stacked in your plate, that's even like, okay, now not only do I have to get all this stuff accomplished, I don't feel I can get accomplished for whatever reason. I don't have either my priorities straight or people pile too much work on me. You want me to take time to learn this new thing. That is the like the real press, I think.

R.J. Talyor: Yes. Yes.

Yeah. Yeah. Yeah. mean, that's why, like people who are, yeah, they will be like the, that's why people who are potentially ⁓ laid right now actually have a big strategic advantage because not until you hit rock bottom or not until you are faced with the end, can you actually restart?

And it's so hard to adopt these things like, in line with what all the work. Michael Maher: They're out there. R.J.

Talyor: Um, I hear the most successful people are saying, Hey, I did a weekend project with AI. did this thing on my side project, on this board that I'm on or whatever, but like they, there's no shortcut, you know, like that you have to learn it and you have to go slow to go fast. And, that's, know, talking about retailers, man, that's, that's the challenge. Like who's saying, okay, just stop what you're doing for a week, put all of the work on pause.

Let's remove our daily comp goal. Um, the sales that we're looking at by the hour. and, let's just like get hands on in cloth or hands on in chat or whatever. Michael Maher: So when you say that, that makes me feel like there's not an AI problem.

Maybe there's a leadership problem you want people to learn stuff and you want to adopt technology. I also think there's a why issue of like people might say, we want to use AI. And my question is why? Not don't, not go for it, but why?

Why do you want to use it? Like what is your use case? R.J.

Talyor: you Mm-hmm. Yeah. Michael Maher: And once you have a use case and you know what you want to do for it, then fine. How do you, how do you integrate this and what's the end goal that you're looking for?

Cause you could integrate AI and it can make things more complicated for you potentially. So if you know what your end goal is and then you know why you want to integrate something, then great, go for it. But then it comes down to leadership. Like, Hey guys, we're going to shift our focus.

We're going to be okay with a less profitable quarter because we don't hit as many sales because we're learning this thing. And I don't, mean, is anybody doing that? R.J.

Talyor: No way. No way. No way. I went to this retail exec offsite where everybody was really rallying around a certain VP of CRM who said that their company was the number of hours saved by the utilization of AI and that each week there was a question of how much, like a calculation of how many queries were done into AI system and then that calculated to the number of hours and their goal was to hit X number of hours saved within the next year.

And that was API being reported at the leadership level, which is cool, right? That's a potentially good example. you talk about, like a way of the leader might lead there, like say like, hey, let's track these hours. But from like a leadership perspective, Michael Maher: Mmm.

R.J. Talyor: The dangerous part that I keep hearing customers tell me is like, back up just a second. I've been selling Backstroke for about a year and a half, right?

And so we've been talking about, talking with these brands for that amount of time. When I first pitched Backstroke, people, like leaders on the team, they're like, don't worry, no one's job's going away. We're not gonna fire anybody. We're not like, whatever.

And then about six months ago, I started hearing people say, aren't gonna backfill people because we think we can do things better with AI. Or we we're actually gonna backfill with a ⁓ more role. And so ⁓ no saying like, I'm gonna reduce the size of my team, or I'm to not rehire this person, but instead hire an AI version of this person. Like there's like, nobody wants to say like the quiet part out loud, which is like, it is coming, the change is coming ⁓ and force through.

Michael Maher: Okay. R.J. Talyor: through metrics or revenue targets or whatever, there's a lot of waiting and seeing and a lot of I see is a lot of people pointing at the bad examples and saying, see, that brand got messed, that brand got called out.

⁓ why we're not doing it yet. Or that's why we have to be cautious. that's ⁓ of there's a lot of action, like we're gonna create our AI committee. We're gonna create our AI workshop team.

Michael Maher: Mmm. R.J. Talyor: And these are these crews of people that are well intentioned, but they don't have quite a mission other than like figure out AI, you know, but it makes us feel like we're doing something.

So, you know, there's security reasons, there are brand reasons, there are other like operational reasons that are these committees or crews are being assembled. But ultimately, I think they're blockers of success. And that is a leadership challenge. Michael Maher: You think the committees that they're building are blockers?

OK, in a bad way. R.J. Talyor: Yeah.

They slow things down. Yeah. They don't, they don't Yeah, I do. Cause they don't have like key.

I'm sorry. Like they're probably like, there's probably an exception where there's one that's like an accelerant, but most times what I hear from brands are like, I'd love to use this, but the new AI committee has to review all AI things. then I say, well, great. What are the three things that they're looking at?

So I can make sure that where you're prepared to show them like, I don't really know. You know, like I changed. ⁓ Michael Maher: Yeah. I don't know.

We're just giving them money to do stuff, so I'm not really sure. R.J. Talyor: Yeah, so, but it sounds good.

So ⁓ why I think like, you know, with Backstroke or with NEI solutions, like what I look for is somebody who just got hired into a new leadership role because they're the ones who are going to implement the change. They're going to look at their tech stack. They're going to look at their processes and be able to actually implement more rare. But they're out there are people who have been at a retailer for five, 10 or 15 years or whatever, and said like, Hey, I'm actually the change agent.

So ⁓ of times in retailers, see their innovation teams, like the innovation team is charged with bringing new tech in. And sometimes those innovation teams are super, they're great partners of Backstroke because they are powerful. charged with ⁓ knocking the walls and getting new tech in. Other times they're just a bureaucracy.

So. ⁓ Michael Maher: Do you think, so you think maybe in some cases these committees, these innovation committees are created an intentional blocker? Or you think they just end up being that way? Okay.

R.J. Talyor: I think that they end up being that way. I don't think that they, don't think, I well.

Michael Maher: Because that honestly is not a bad idea. If you're like, I don't want new technology coming in here. Let's get a couple of people in a room. That's more of a conspiracy theory, probably.

maybe it's just the lack of intentionality turns it into that. Let's pull this person, and this person, and this person. What are their qualifications? What are the clear things that they need to determine for this technology to be useful?

And no one's doing that. just saying, figure out AI, like you said. R.J.

Talyor: No. Yeah, I- Yes. Yeah, well, comes, you know, it comes back to failure, which is my favorite topic that nobody like as humans, we don't like to fail, right? We avoid failure at very high costs.

We would be boring or average than fail. And ⁓ Michael Maher: Because why do you think that is? R.J.

Talyor: Well, because you can get fired really quickly if you fail. ⁓ Michael Maher: I don't know why I'm laughing. That a great reason to say that. I was going to say at an even deeper level, I think it's because we tie failure to identity.

R.J. Talyor: Yeah. yeah, as humans we're herd animals.

We want to be a part of the pack. We want to be different. We want to be outcast from the group. Michael Maher: You fail, you have been taken down by the lion as a gazelle, and you're no longer part of the pack.

Yeah. R.J. Talyor: Yes.

Yeah, yeah. You're different. You're other. Yeah.

All those things. Michael Maher: Could you imagine a pack of gazelles saying, guys, we lean into failure, fail for fail into the lion's mouth. Like, those things are so at odds with each other. But but yeah, like, because of, think, just ingrained in our DNA is like, we want to, and I think it makes sense.

Like, kids are very selfish and can be jerks because they are trying to, I think, survive. And so they're like, I want this, I need this, I want this. They're not. R.

J. Talyor: Yeah. Totally. ⁓ Yeah.

Yeah. Michael Maher: thinking about other people, but that's because they're designed to keep themselves alive. You make a bad decision, you get killed in the long run, and we have to learn to switch that into what we're doing now. R.

J. Talyor: Mm-hmm. Yeah. Yeah.

And corporate structure or, you know, in larger retailers, like you put your neck out on the line, you're going to potentially get the boot, you know, when things, ⁓ so, you know, like I really admire, innovative people in corporations and I've some of them through, because they're all the people that are interested in AI, which is pretty fun. but the hurdles that they have to, jump over to get some new tech in. Michael Maher: Yeah. Yeah.

R.J. Talyor: pretty aggressive. just landed a deal that took a year, a year to implement year for an AI solution, like where the art team was like, let's go, let's go, let's go.

I ⁓ I mean, I get tired after like two weeks, you know, of something new. ⁓ Michael Maher: Man. that takes a special kind of person and temperament to deal with a lot of nos, basically. R.

J. Talyor: Yeah, because you have to go through the security team, you have to go through the brand team, have to go to exec, you have to go through procurement. Like there's no AI budget. You have to then displace an agency or a solution that you already have to bring in this new untested thing.

And then you have to get the actual users to say, I'm going to take on this additional work that I have to slow down and learn. like, yeah, it's pretty. daunting. And that's why a lot of these AI solutions people are going to conferences or doing all sorts of things to say that they're like, I'm learning about AI, I'm trying to figure out what it is.

I'm not, I don't want to be that, you know, I don't want to be the failure and I'm going to point to the failure and then I'm going to put my proposal together for 2027. I'm going to put together my AMI bulletproof AI proposal for 2027. like, you know, I mean, Michael Maher: Hmm. By that point.

R.J. Talyor: Big companies will, they have enough padding to survive. that's why a lot of the innovation is actually happening with these smaller challenger like data, ⁓ brands who are gonna eat the lunch of the bigger ones or get by them because they're able to move faster.

Michael Maher: Mmm. Yeah. The acquisition part, think, is huge. You look at any big, well, one, I was going to say, you layer on the fact that these big brands are, let's say, they're publicly traded companies.

They've got governance and compliance that they have to abide by. So they are crossing their Ts and dotting their I's for sure. But that, and that makes it really hard sometimes to get stuff through. Because for some people, it is just, just working a job.

This is my job. I have to follow these rules and that's it is what it is. And that's okay. You know, the world takes all kinds of people, but those challenger people, I know one who works at a big company.

I had the great pleasure to work with him closely in a project and he's just like, he's the kind of person that I'm like willing to take his call any time. And he's willing to take mine anytime cause we did great work for him. But he, the way that he pushes back on stuff and he's always kind of like, R.J.

Talyor: Yeah. Yeah. Yeah. Michael Maher: You know, people are always telling me like, why are making so much noise and blah, blah, blah, blah, blah.

But like he's doing it not just to make noise, but because he really believes in these things. He's like, if we talked about this recently, he's like, if I try, you know, 20 new things and 19 of them fail, but one is like really, really successful and like that's a slam dunk. And that feels like a failure to some people because you've, failed 95 % of the time, but like that one could totally outweigh those other things. And so he's thinking about that.

R.J. Talyor: Yeah. Yeah.

Yeah. Michael Maher: that one. R.J.

Talyor: Yeah, well, I mean, that's a combination of one, right person, the right role, but then also created that role that he is able to test and fail and fail 19 times and win one like kudos to that. Cause there, that's how you end up winning too often. say to, or heard, and when I've worked at bigger companies, it's like a fail within this box. you know, like, yeah, Run, run the test, but like, if it's a failure, then cut it off after one day.

Michael Maher: You can fail, just don't fail that much. R.J. Talyor: And truly, it was going to minimize the loss.

And that's human, very human. you were talking about why you're an entrepreneur. I'm an entrepreneur because of this. I love it.

And it actually goes back to creative writing degree. Creative writing degree is all about like, Michael Maher: Yeah, ⁓ man. R.J.

Talyor: write something down, put it in front of your classmates and they all just trash it. And then you iterate and you iterate and you iterate and you and you get thick skin and you like try again. And life's about resilience and everybody says that, but like nobody likes the feeling of failure. I don't like the feeling of failure.

But it's like motivating to me. I kind of had a bad day yesterday. We're covering everything. And I was like really pissed.

And then I swim, which is why my company is called Backstroke. Michael Maher: Hmm. Yeah. I love that.

Okay. R.J. Talyor: Yeah, I swear I swim in high school swim in college.

I still swim. And so, you know, I was really upset. So I slept on it, got up this morning, went for a swim back in it. You know, it's like, let's go.

I'm frustrated by the what happened. But, you know, it's like iteration. And, you know, that's that's the entrepreneurial journey. That's the AI thing.

That's like building new tech. Michael Maher: That's everything, man. That is everything. R.

J. Talyor: Yeah, but some people don't want to feel that, you know, like I'm, people don't want to feel ⁓ downs as well as the ups and you just, you're kind of more comfortable with the ⁓ moderation. Michael Maher: was exactly what I was going to say, is that when we start chasing comfort, that should be the opposite of our lives. Because comfort doesn't actually get us to reach our full potential.

And while we may not want to feel pain, when we do reach our full potential, which comes death, I guess, that's your full potential, right? R.J. Talyor: Mm-hmm.

Yeah. Yeah. Michael Maher: because you've lived your whole life, hopefully, long life. But you don't ever reach your potential.

But when you do reach your potential, amazing because you have the And I'm not talking about like money is great. Don't get me wrong. I don't want say like it's not about the money. Like, trust me, if I had more money, I would fix a couple of problems.

Like, it would solve some problems. It doesn't solve all your problems. It doesn't make you truly joyful. It might make you momentarily happy.

But you start to actually R.J. Talyor: Mm-hmm. Michael Maher: achieve some things and maybe see some progress and move stuff like that incredible there's a an amazing that I love that I said someone recently ⁓ from the Bible a friend of mine who was just dealing with some challenges and I said Look regardless of what believe.

I think that this is and true but Because God created us and loved us are, and we deal with all these challenges and difficulties. It's not in spite of the challenges that we become conquerors. It is in these things, is what Paul says, in all these things, we are more than conquerors through him who loved us. We don't have the challenges.

We do not get to be conquerors. There's no battle. There's no win. And you talked swimming.

I was gonna say, I've been running a lot more. R.J. Talyor: Mm-hmm.

Yeah. Yeah. Yeah. Michael Maher: And the first mile, just because I have a buddy who's an ultra runner and he started inviting me to run with him, I'm like, I hate running.

This is stupid. And now I find myself running all the time. But the first mile is like, I hate this. I really hate like I do not like this.

And then by mile four, I'm like, OK, I think I could go for a while. Like, you you find your pace, like you find more a little bit more tolerance, I think, in the pain. But like you are you can become a conqueror because of those challenges. You live in comfort totally.

R.J. Talyor: Yeah. Yep.

Yes. Yes, Michael Maher: You don't challenge or press yourself. You conquer nothing. There's a, I think, a loss your side there.

You're not living up to what you truly can be. R.J. Talyor: Yeah.

Yeah, yeah, think that very much. ⁓ agree with it and it's... Yeah, it's like the cool opportunity and challenge of it all. I my kids this story, but back in the days, cars didn't tell you how many miles you had left in your gas.

⁓ It would just get down the thing and then the light would come on. And I knew that my old I could get to 287 miles ⁓ because I ran out of gas. Michael Maher: Yeah, ⁓ yeah. Mmm.

R.J. Talyor: And like, I knew exactly the number of miles that I could get to because I got to the side of the road and I had to, at that time, walk to the gas station ⁓ to get a can of gas. Yeah, it's the worst, you know?

But like, I know how many miles can get to, how long I can push it. And it's like a, it's a dated metaphor now, but like it's true, you know? Like you find the limit and then you pull back from it. I...

Michael Maher: Man, I've done that before. R.J. Talyor: You know, and I think that's one of the reasons that people like to work with me or with Backstroke or like, like to work with startups in general, because we believe in a future that's like kind of wild and crazy.

and then a lot of times corporate or bigger retailers are like looking for that, you know, because there is so much like mitigation. but on flip side, it's, know, it's exhausting and you have bad days sometimes ⁓ or ⁓ Michael Maher: I mean, that's just the reality. Like you said, you're going to have a bad day. But it doesn't mean that you failed fully or that you, I you ultimately fail in the wrong way when you just quit and say, I'm not going to push forward anymore.

Now, quitting is very different than like, this path is not working. I need to pick a new path. That's very, very different. But you said something that resonated with me.

I turned 40, and I have a friend of mine that gave me a book. I got 15 bottles of bourbon. R.J.

Talyor: Yeah. Yeah. Yeah. ⁓ Michael Maher: a pair of running shoes for my running buddy.

And then another friend got me this really incredible book called the creative art, a way of being by Rick Rubin. And it's like 400 pages and he's very like Zen spiritual, et cetera. And, there's a lot of cool stuff that's in there about creating art, but it could be certainly applied to anything. And the chapters that I were reading the past, like that I was reading the past two nights just talked about, like when you create art and you hold it back, you, R.

J. Talyor: Yeah. okay. Michael Maher: you let's say you work on something for two years, you start to become disconnected maybe from that work.

And it's not a true representation of who you are now. But a lot of times, you know, a comedian, my whole back of jokes, like I'm gonna wait for, you know, a bigger opportunity, a bigger time. But like you've there's always more if you think about it. So create, do the stuff.

it doesn't land. Maybe it doesn't perform, but you've always got more. Keep creating was like the point of it. And that's what I'm hearing from you is like you fail, but keep going, keep going.

R.J. Talyor: Yeah. Yeah.

Yeah. Yeah? Yes. Yeah.

Michael Maher: Try more thing, do one more thing. R.J. Talyor: Yeah, yeah.

You know, one of the things I've done startups now for a while and people ask me for advice and they'll start up. People say like, I want you to send this NDA. Like before talk about my idea. And I always think like, like.

never invented something that's like that mind blowing that would like, but instead I think share early, share often. And the way that I express this idea and solve it is so different than the way you might do it or somebody else that like, you know, we all see what the problem is. like generative approach to email, predictive email, like everyone kind understands what I'm talking about. The way that we're solving it at backstroke is different than our competitors.

So share early, share get the critique. Michael Maher: Yeah. R.J.

Talyor: pitch it as many times as you can and get the feedback and then listen, you know, then you have to kind ⁓ listen all those ideas and understand like what What are the themes that you believe in? Not just the themes that other people believe, but what are the themes that resonate with you to make the idea better? So it's the same thing. like, you know, you're talking about art, talking about building software, we're talking about solutions for things like sharing community, all that.

It all ties together. so, I mean, this is like, I don't know, conversation about AI that's gone all sorts of places, but that's exactly, I think, the way that it should go, you know? And that's what makes it so exciting. Michael Maher: It touches a lot of different parts of society, but it also, I think there's a threatening factor of it trying to replace our humanity.

And that's the thing that it will never do. R.J. Talyor: Yeah.

yeah, I am. Ship Conclusion. ⁓ Michael Maher: There we go, ship I absolutely love that. RJ, if people want to find more about what you're doing, where should they look?

In a pool? You're be doing some back shows? Tell people where they can find you. R.

J. Talyor: I mean, maybe that's a good spot, but backstroke.com, that's us. So just find us at backstroke.

com or can email me. I'm RJ at backstroke.com. Michael Maher: RJBackstreet.

com, love it. Which by the way is an amazing URL. Have you had that URL for a while? R.

J. Talyor: Hey, thanks. No, you know, no. like, you know, what's wild is I was trying to figure out what should be the name of this company and had all sorts of names and stuff.

And I've read some article that like, um, uh, hard K sound is a really like, like a memorable thing for the brain, like cola, um, like the, repetitive K sound. Um, and so was like, okay, trying to think about words that made sense to me. My previous company was called pattern 89. Michael Maher: Mmm.

R.J. Talyor: that no one remembered because they're like pattern 41, pattern whatever. It was a cool story and stuff, but I was like, I want it to be associated with me, something that I'm interested in.

And no joke, was a Sunday night, was kind of like drifting off and then Backstroke came to mind. I went online and it was affordable. I actually spent Butterfly in college. That was my stroke, but butterfly.

com was $750,000. So we're Backstroke. I could afford Backstroke back on. Michael Maher: Hmm.

Okay. man, that's so good. Hey, Cartology is the name of my agency. I did not even know that, so just lucked into that one.

All right, well, you heard it here, people. RJBackstrap.com, backstrap.com if you want to find out more about what they're doing.

That's all. You don't got to go home, but you got to go somewhere else. don't know where you're to go, but that's out. We're out.

That's it. We're out.

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