Ep. 12 | Embarrassment, Experimentation & the Founder Mindset: What Slack’s Co-Founder Can Teach Your Career

📖 Episode 12 Summary

In this episode, Amanda breaks down a surprising founder story from Slack’s early days — including the moment Stewart Butterfield publicly called out Slack’s first product and how the team responded in an unexpected way. Rather than focusing on shock value, Amanda uses the story to reveal what it teaches us about creativity, innovation, and the inner game required to build something that doesn’t exist yet.

She explores the mindset shifts that separate game changers from the crowd — how they interpret tough feedback, how they move through imperfection, and how they turn discomfort into forward momentum.

Listeners are then invited into a simple but powerful reflection exercise to identify the qualities that already make them creative — and the edges that, when strengthened, unlock their next level of potential.

This episode is a masterclass in thinking like a founder, experimenting like a creator, and reframing embarrassment as one of your greatest tools for growth.

Referenced Resources

• Business Insider feature on Slack’s early founder story

Transcript

Amanda Escobedo (00:01.25)
Welcome to the game changer by a powerhouse coaching your podcast to master the mental game, elevate your brilliance and build a legacy of progress and impact. My name is Amanda Escobedo. I'm your host, inner game coach and here to help you change the game. Welcome to episode 12. It has been 12 weeks already. A little crazy. I hope you all had a wonderful Thanksgiving.

I did very much so. My family's traditions have kind of evolved through the years. When we were little, there was a lot of intention with bringing the kids together, all the cousins together, and we'd have a whole feast with our grandmas and all that. But now, know, some of the grandparents have passed. Now all the kids are adults. Some of them live in different places. And my parents and me and my brother have

moved from LA to Orange County and majority of our family's from LA and it's almost like we moved to a different country. So the effort of trying to get the family together for Thanksgiving or holidays, moving LA and Orange County people together always feels like a lot of work. And I think my parents and family's a little overcooking for good reasons. So we went to a restaurant, a Mexican restaurant, a fancy one, and it was very tasty. It was so freaking good. I had like a surf and tur-

dish that was bomb dig. We basically got VIP service from this great restaurant and it was amazing. I will say our family, did have some type of turkey. We're not really big turkey Thanksgiving like folks, even when we were younger, the feast was primarily like Mexican food. for this and maybe we had some ham or something, but for this Thanksgiving, my brother actually hosted a really great friends giving and he smoked.

an amazing turkey and then there was all these goodies. So I did have a traditional Thanksgiving. There were a ton of people there and my parents were there. So I feel like we had like your traditional Thanksgiving the week before and then our family when we relaxed at restaurant was amazing. I ran nine miles that day. I'm going back and forth with myself with like kudos or like not following through on my commitment, following through on my commitment. And what does that mean for myself? Well,

Amanda Escobedo (02:13.686)
In my mind, the day before I and actually the week of maybe the whole week, I had told myself for Thanksgiving, I am running 11 to 12 miles and I ended up running nine. And I'll be honest, I don't even know how I made nine. I just felt like my body was fatigued. I had set my alarm for super early for like three thirty in the morning to like have my pre-workout, let it digest and go for my run at six.

I just kept snoozing and snoozing and snoozing. So something's going on with my body because it's been a system for me that's been happening these last two weeks. Usually I'm up at the gym at the 5 a.m club, but my body has just been breaking down and I'm trying to figure out well one I have not been sleeping very well so that's one and I always go back and forth on what's that line in which you push yourself and versus what's the line and when your body's literally talking to you and you need to listen to your body because I've gotten it wrong.

and when I get it wrong and I push myself too much, then I'm out for like a couple of weeks or even a month because of whatever I pushed myself too hard on. So that was the balancing game I've been playing. I'm still kind of playing, playing a little fatigue. So that being said, I was snoozing, snoozing, snoozing. I was like, okay, we're going for a run. Even my brain was trying to do the, what if we do it tomorrow and then we can do the full 12, all these things. And usually for a long run, I run by the beach. So it's a lot more engaging. You get

breeze in your face. Like you have the beach and the water and the sand to look at. But I think just because I had pushed my run out so late, I was like, let's just run in the neighborhood, which is just big laps around my complex area. It gets a little dull, gets a little boring. And doing that over and over and over. I don't know. I, my body wanted to shut down at mile five and I got to mile nine and I was like, can we do mile 10? And we were like, it's not.

I'm proud that still a long mile. Nine miles is commendable. It's a lot of miles, but mine still is kind of like kicking myself in the butt. I didn't at least do the 11. So all is good. Still proud. Still, you know, earn my calories to grub that day. We just got to keep putting in the work. So it's a little of my fun Thanksgiving. Also very fun. I took my dad networking with me, which was so great. So my dad is just a natural smoozier.

Amanda Escobedo (04:34.562)
way better than me. He's so much better at business development than me. He's natural, such a natural connections and he's always just whatever he's passionate about. He's, hate to use the word sell. He's all about adding value to people. So he's a massage therapist as well. And so he's always talking about massage therapy and everyone's like, how do I get services from you? And he's not trying to sell anybody. He's just really passionate about healing people, about helping people.

And he feels very passionate about me and exactly what I'm doing in my coaching world. And so I thought who not better than to bring onto the empower house team, somebody that's passionate about what I do believes in what I do. And him and I have very similar personalities. We're both pretty engaging. We both build relationships pretty easily. We're both very curious.

And we both just want to add value. And he's always kind of looked to me like, Kuschma, and I wish I was able to do what you are doing. Like, cause he believes kind of the coaching world is very much in his realm of expertise and expertise is maybe the wrong word, but this industry aligns with his personality and who he is. And so I think he was very excited to kind of join me within this. And so it was fun. Like I was at this networking event.

with all these like business owners or people that support businesses and doing introductions and I'm like, and here's my dad, which was hilarious. Everyone's like, oh, your dad's here. And then my dad is hilarious because he's speaking to like such a proud father and he was making connections through the room. And then all these people were coming up to me like, I just had to meet you. Your dad is just so proud of you. So it was very, it was a very fun and networking environment to have done that with my father. The goal is to let him.

fly without me. So he's got a lot to learn about in powerhouse. He's got a lot to learn about what we specialize, what we do. And I'm excited to bring him on board. And I also have my mom helping me with operations. So we're also looking to just streamline some things, improve the customer experience, and then streamline like social media stuff and all that. So who not better than to bring on the Escobedo family to the empower house family. So it's very exciting to be partnering with my family on all.

Amanda Escobedo (06:49.976)
this. So for today, let's dive into a bit of our topic for today. I was going back and forth on these two articles. I want to like do the whole like beating a dead horse sort of thing. There was one article in particular that jumped out at me that was related to AI and the job market. And there was a bunch of layoffs that happened at Amazon and like just the ties of the title.

reading through it was the same narrative where it's like they're pulling out and inferring that these layoffs are related to AI. And then when you actually dive into the article and things that they're quoting, you're like, actually has nothing to do with AI, but the deadlines and the whole narrative is just bleeding fear, bleeding fear. So I'm not gonna break that down, because we've done that last week for you all. We did it the week before, but what I do wanna leave you with is really, again,

I want to cultivate a curious mind for you all. Curious, curious, curious, curious. I'm going to say it over and over and over. I want to cultivate a curious mind. Again, my goal is not to tell you what to think. My goal is to help give you some tools on how you can effectively think. And effectively think is really understanding how to see and experience the world more objectively than subconsciously your

bringing in all your past experiences, your jaded experiences, you're bringing in everybody else's opinions that you don't even recognize have you have now absorbed, they have now become your belief system, similar to you absorbed all the social media and the media narratives, and they have potentially become your belief systems. And so I want to challenge your belief systems. want to shake up your belief systems. want to increase your awareness of

What are narratives that you are potentially applying to circumstances? What are judgments that you're potentially applying? Because judgments block your creativity. Judgments block the access to your inner confidence, your inner wisdom, the groundedness. You know, if you're trying to break away from the anxiety that you're feeling all day, the way to do that is by starting to shed off and one, become aware of the type of judgments that you have on yourself.

Amanda Escobedo (08:56.204)
become aware of the type of judgments you're applying on other people, become aware of the judgments you're afraid of what people are going to think or say about you. And those judgments and narratives are applied to every single type of circumstance. And so I'm trying to increase slowly your awareness of what is truth versus what is a narrative? What is truth versus what is your judgments? What is truth and objective reality versus what is a tale?

just these stories and these belief systems that are applied to circumstances. So again, I'm not going to dive too deep into this article because it feels like it's the same thing I'm starting to repeat over and over. So, but I didn't want to highlight once again, another article. And if you are in a position of wanting to go to do something on your own, you're trying to determine, am I gladiator? Am I a Spiderman? Is this my gladiator season where it's really, I'm all in whether I live or I die. You know, you're jumping out.

no matter what the headlines are saying. maybe, and if this is the case, maybe you're taking the headlines as data points on, this a safe job market? Is this an opportunity for me to go aspire for my dreams? Whatever that is. So that's one piece. Or maybe you just got laid off and you're very fearful on how do I get another job? The job market looks bad. AI is taking everybody's That's the narrative I wanted to kind of like shock out of you. That narrative is not going to help you get another job. That narrative is not going to help you get creative on how you can

approach these different organizations. It's not going to help cultivate the creativity on how you can solidify that next opportunity for yourself. So the more we can get you out of fight or flight state, the more we can get you into your grounded state, the more we can get you into this abundance mindset, the more you will flourish. And all I want you to do is flourish people. All I want you to do is activate your human potential.

Create a vision for your life and go follow and do that fearlessly. And I say fearlessly, you know, really the goal is not fearlessly. You're a human, you're going to have fear. But the goal is help you reframe that fear and walk hand in hand with fear and go after your dreams. And so instead of going too deep into a particular article on that topic, we're actually going to review a founder story. you know, one of the things I do is I specialize in supporting

Amanda Escobedo (11:17.812)
founders. I'm a coaches founder, a coaches founder, a founders coach, a founders coach. I work with founders. I work with a lot of executives and business owners. And so what I always love to do is unpack the founder story from like, what are the key characteristics that create just a driven innovative founder? They're very unique human beings. Not everybody thinks like them. And because they think so differently is what

as them go onto the path of uncertainty innovation. They've got a vision that they are so obsessed and attached to. They're able to see something that not everybody else is able to see. And they have full faith and self-belief that this is a possibility to create. Whereas everybody else in the world, we're all looking for certainty. We won't go down the path of uncertainty. We need to know that we will be safe. will, this is founders are the gladiators, right?

They will go into the arena and they will go in whether they live or they die. They will die trying. There is no regrets in their life, people. And so I want to unpack this founder story a little bit. It's actually a recent story that was published on Business Insider on November 23rd. And so it's a story about cultivating creativity in business. As you all know, I've mentioned over and over, I specialize in cultivating creativity in business.

The headliner that caught me was called Slack Co-Founder. Slack Co-Founder says embarrassment can be motivating, but it can also lead to employees papering the office. And I was like, what in the world is this about? know, Co-Founder caught my attention, Slack, a company I know caught my attention.

The word embarrassment and motivating caught my attention. I'm like, here's a coaching story. And then what got me very confused is, but it can lead to employees, papering, and office was very confused. And so again, in today's story, this is really about cultivating creativity in business. And I specialize. So one of the things that I'd say that separates me than other coaches, my biggest approach to solving problems for founders, executives,

Amanda Escobedo (13:31.682)
I specialize in cultivating creativity in business and also cultivating creativity in life. And so that's what the story is about. And cultivating creativity in business, it's about a messy reality of building something new. And it's a mindset that takes to pioneer when the path does not exist yet. And so again, as I was scrolling through and I saw this headline, I was like, Ooh, a tech story about a Slack founder, Stuart Butterfield. That's what caught my attention.

What caught my attention also, again, Slack, one of the most known companies. think if you're working in an organization, you probably use Slack to connect and communicate within your team. Secondly, is this founder story. As I mentioned, I'm always curious on how founders think and how it connects to some of the fundamental creativity tools which I'll be sharing today. And then also what caught my attention is, you know, this is an article that just pushed out November 23rd, as I mentioned, of 2025, but...

really they're just retelling a story from 2014 which means this moment clearly left a mark this 2014 story clearly left a mark we're still making it about a decade later so that's what i found interesting so here's kind of what the story is about so back in 2014 when slack was still early

Stewart did an interview with MIT Technology Review where he described the product, the product of Slack that they were building and I quote, a giant piece of shit. That's what he said about his own product on an interview with MIT. He said the team should be humiliated. So now this is, now he's bashing the team. Not a good thing. He said the team should be humiliated.

that this was the version they were offering to the public. Bold, bold. Am I right? Especially when your employees are still in the trenches of building this product. And what I want to be super clear about as I'm referencing this founder story, I would not hold this story or anything that we're walking through here as an example of great leadership communication. That's not what I'm highlighting. So you will...

Amanda Escobedo (15:47.086)
I find notes throughout this story. would say poor leadership. I don't like to generalize. He's not a poor leader. He's obviously very successful and Slack is very successful. And one of the things I don't like to do is generalize people. One of the things we, as people tend to do is generalize people. Someone is either good or someone's either bad. I think what's more effective is pulling out specific behaviors that

or maybe not good or bad and putting judgments on those particular behaviors as an example, rather than putting the judgment on the person. And so as an example, if we were to kind of extract this for a second saying, you know, and I quote, like the product that Slack had produced today is a giant piece of shit. And then also the team should be humiliated. I'd say those comments is communication and referencing the team is very poor as an example.

leadership. I wouldn't call him as a whole poor leadership. I don't have enough data points honestly to judge his leadership as a whole but those are examples where I'm like that's not gonna be very motivating for the team. I say that however we shall continue through the story and you'll find maybe something completely opposite than I just said. So you know as I mentioned if I were coaching a leader

And especially in a large enterprise, I would not say, hey, go call your team product, go, go in front of press and call your team piece of shit. But I would not be recommending that at all. That's not, again, the point of why I'm sharing this. So my approach with this story is to really extract the creative entrepreneurial game changer lens. So looking at this from a mindset point of view.

the drive, the motivation and drive and the characteristics that fuel innovation. So not using it as a template for clean, mature leadership behavior. Obviously we're experiencing phases of growth in his leadership. That's a whole nother episode to unpack. And what I'm interested in is what does the story reveal about the mindset required to build something that has never existed before?

Amanda Escobedo (18:03.022)
So again, what is the mindset that is required to build something that has never been built before? So as the story continues for this 2014 story, the next day after Stewart had that interview with MIT and he was talking to the press and spoke poorly about the team, his team, the team that he was talking poorly about, printed Stewart's quote onto 40 sheets of paper and pasted it all over.

the office. And so they literally quoted the, you know, the team is a piece of shit, so our quote and they printed 40 sheets of paper of it. Now that type of response from the team, it tells me a lot about a startup culture. I've worked at many startups and it tells me kind of reinforces some of the cultures that I've worked at, but it tells me a lot about a startup culture and the kind of person who tends to work at a startup.

Startups are not easy. So number one, if you've ever worked at a startup, it is not easy. It demands a lot of grit, a lot of adaptability, a lot of resilience and thick skin. Honestly, you definitely cannot take things personally at a startup. And most people who consciously choose to work at a startup are there because they believe in the vision. They're excited about what's possible.

And they want to be a part of building something that's never been done before. So I have to say, you one of the first times I went to a startup, some of my friends or family was like, are you sure you want to go there? Startups are not secure. What if you get laid off? What if the business closes? And you know, the mindset that a startup employee has is so what I'll get another job. That was my mindset. Okay. They're like, you need, don't you want good benefits? All this stuff. It's like, yeah, but you know, all that stuff comes and goes. Nothing is guaranteed.

And so when you move to that startup again, the type of employee that is attracted to a startup is someone that believes in the vision that that founder has for whatever they're building. And they're excited about what's possible about building out that vision. They want to be a part of building something that's never been built before. And so when the founder who has a clear internal vision for what great should look like says something so harsh, like the team.

Amanda Escobedo (20:23.158)
should be humiliated, etc. And the team has a playful response starting to print that quote, plastering it everywhere and turning it into wall quotes. To me, that actually shows a culture of humor. It shows a culture of shared ownership. It shows a culture to me of shared understanding of the standard, and it shares a hunger to improve. To me, and this is my interpretation, so someone else could

definitely disagree, but to me, because the entire office was all about printing this quote, plastering it all over and they did it together. This tells me the team says, okay, if we're going to build something world class, then let's own this moment together. And to me, that is such a startup response. And that is the type of attitude that will make you successful in working at one of those organizations. And so at first glance, you know,

couple different things about this story that surfaces is continuous improvement versus protecting the past. What does that mean? Continuous improvement versus protecting the past. So these are key what I'm starting to do now is unpack key characteristics of what I consider like the game what makes someone a part of a game changer story. Continuous improvement versus protecting the past. So at first glance continuous improvement

Sounds obvious, right? Like, of course, Amanda, everything should be improved. And when I'm talking about continuous improvement, means being an employee, being a leader in an organization, and one of your goals is to continuously improve something. whether it's processes, customer experience, efficiency, your mindset is always, anything can always be improved. There is no end to improvement. So we're constantly looking for ways to improve.

Now that might sound obvious. Yeah, Amanda, everybody has that mindset. Everyone should have that mindset in an organization. How can we continue to improve? Right. But in my experience, especially working inside of a large organizations, large enterprise organizations, this is not a given. What often happens in a big organization is a leader or a team build something big. Let's say they build a process, a system, a program. It works. It solves a problem.

Amanda Escobedo (22:46.818)
Right. And so in this large enterprise, whatever you've built, it works. It solves a problem. You get recognized and you get rewarded for building that. And that success then becomes a part of your identity. Like I built this thing. This is my legacy here. So when new leadership comes into play or new talent comes in with an impossible goal or what feels like an impossible goal.

So, when new leadership comes into play and they're like, this is the new, I don't know, goal stop, proper term, but this is the new, not the new vision. The vision is generally always the same, but this is the new goal for the year. Let's just simplify that. If a new leader is coming in and saying this is the new goal, we need to evolve this. What they're saying, we need to improve, we need to do things differently in order to achieve this goal.

When a new leader is coming in and setting that new precedent, it can actually feel very threatening. So instead of thinking, yes, everything can be improved. Let's figure out how to do this. A lot of people in large enterprise organizations, I'm totally generalizing by the way, but a lot of people within these larger enterprise organizations, they start instead of again, going to let me figure out how to achieve this goal. Let me figure out how to make things better to achieve this goal.

The mindset starts to shift and it's like, no, no, what we built is actually the best version. It can't get any better and change. means you're saying that we failed. That's what the actual underlining interpretation is. If you're saying that you need to change what I've built, this was my legacy. This is my identity. It becomes threatening to my position. It becomes threatening to my identity. And so what happens is people start to cling to their old work instead of evolving it. And that's the opposite of

creativity. That's the opposite of a game changer mindset. Because at the end of the day, whatever you believe drives your behaviors. So if you fundamentally think that or believe everything can always be improved, then your brain will start scanning for opportunities to refine, to evolve, to simplify, to elevate. But if you fundamentally believe, this is as good as it gets. I've built the best. It doesn't get any better.

Amanda Escobedo (25:07.928)
then what happens is if someone is starting to challenge you to do better, is challenging you, hey, there is an opportunity to make this more efficient, to pivot, whatever that is, then what happens is you start scanning for all the reasons of why this won't work and you start to protect the past instead of building for the future. And so Stuart, for Stuart, this is a terrible comment that came from, you know, there's a gap between here and where we

where we need to be. That's the belief. So when we go back to his terrible comment, you know, what we've built today is a piece of shit. I should probably stop saying that word, but what we've built is not great and the team should be humiliated. His underlining note there is there is a gap between here and where we need to be. That's what his underlining note is with that phrase. And again, I'm not praising his delivery on what he's saying. I'm more highlighting the underlying the belief. There's still a gap people.

We have not made it. Don't think you're done. The system can be better. We have not achieved what is possible. And so this to me is a very deeply creative mindset. And I want to go back and highlight what I'm trying to highlight. It's a continuous improvement versus protecting the past. And so I want to invite you to think of for yourself, you know, when people invite you to create something, to change something, are you resistant to the change or are you constantly

Like, huh, let me figure out how to do that. And how you're approaching that invite is either going to block your creativity or it's going to cultivate your creativity. So the second thing I want to highlight about this story or really about this founder, Stewart, is a clear vision of what great should be. This is what really is so powerful for founders, their vision. They have such a strong, clear vision. So when Stewart said the product was terrible,

He wasn't just attacking the team. That's what I want to make clear. He was really pointing at the space between the space of where the product was and where it needed to be in order to fulfill the vision that he had for Slack. And so in his mental picture, felt it made sense of what Slack could become, how smooth it could be, how intuitive it could be, how transformative it could be for teams, how central to the future of work it could be. That clarity,

Amanda Escobedo (27:35.618)
his clarity starts to move the company forward with that vision. Creative pioneering people often feel this tension as well. When I talk about this tension, it's this tension of what exists right now and then not yet reflective of the full vision that I can see of what's ahead. And so sometimes that frustration of that tension, right, of where we are today versus where I believe we can be,

Sometimes that frustration leaks out into intensity and harsh critique. And again, not a best practice of leadership. There's an opportunity to cultivate conscious leadership here. But a very real founder of psychology, they're living in the future vision while everyone else is really dealing with the MVP.

Now the third note that I want to highlight of just kind of the mindset of the founder that is very creative is this whole embarrassment and a positive attitude towards failure. That's really what this story is about. The headliner talked about the embarrassment and how it could be a motivating factor. And so let's carve this out of its own section for a second because,

This is less about a positive attitude towards failure in a fluffy way. It's more about your relationship from my perspective, to embarrassment and experimentation. What is your relationship to that feeling of being embarrassment and what is your relationship with experimenting? So when you're building something new, a product, if you're building a service, if you're building a brand, if you're building a company, it's called new for a reason.

If you're building something new, a new product, a new service, a new brand, a new company, it's called new for a reason. It's never existed before. So you have to treat it like a trial and error. You have to treat it like an experiment and adjust. You have to treat it like a launch and a learn. Failure in that context then becomes data. It becomes information. It becomes direction.

Amanda Escobedo (29:47.64)
What's critical though, through this entire process also, is reflection. So when things, when you launch something and things don't go as planned, don't meet your expectation, it's reflecting, meaning watching the replay. Go watch the replay, go sit with the feedback you received, go study the friction points, ask yourself what worked and what didn't work.

and not coming from a place of self-attack, right? Not coming from a place of self-judgment and beating yourself up, but more coming from almost like a curious scientist mindset. So, and what that means to me is almost like you have, you know, we had a hypothesis, we ran an experiment, and now what did we learn from this experiment? And somewhere along the way, often very early in our school of childhood, many of us have internalized this

perfectionist mindset. If it's not perfect on the first try it means I'm not good at this right. If it's not understood by me immediately it maybe this means I'm not meant to do this. But game changers don't operate in that way. There isn't a perfectionist mindset. They fundamentally understand again that it's not about failure that they're recognizing they're doing something new.

And so they're treating it like an experiment. So they have to treat it like trial and error, experiment and adjust and launch and learn. And so when things don't go as expected, they're taking in the data, they're taking in the information and then they're redirecting accordingly. And so let's go back to this example or this note on embarrassment. If you can get comfortable with getting embarrassed, if you can get comfortable with yourself,

putting yourself out there, experimenting and being open to looking dumb, you will naturally become more creative. You will naturally become more resilient and more effective. And as an example, you when I first started coaching, I remember when I first launched my Instagram account and I had no followers at the time, right? Once you create it, you have no followers. You have to invite people or like start posting and maybe hopefully have organic.

Amanda Escobedo (32:04.618)
traffic, but in the beginning you really want to at least invite the people that you know to follow you, right? And so when I first created my Empower House underscore coaching Instagram account, I took a very long time to invite my friends and family to the account. I didn't want people from my old or current life to really see what I was doing. I was so scared.

for them to see what I was doing because I was so new to it and I didn't really know what I was doing. And so I just was like, people are going to start to question what the heck is Amanda doing? Who does she think she is? And I remember when I first posted my first video. So I actually invite you all to go deep, go deep, go deep, go deep into my Instagram account to one of my first videos. I look like a deer in headlights. I look crazy.

I look so crazy when I meet, but I look crazy because I was just so scared in that first video. I didn't know how to make a video. All I knew is I had information to share. All I knew is I had information to educate people. And all I knew is I just wanted to help people. And so I created this video and was just talking on the camera. I look crazy. Like the background is just so blank, like all the things. And I just look like a deer in headlights. And so I remember I pushed that out. I don't know if that.

the time if I had followers or not yet. I did. Either way, those are probably my two biggest scary moments with my social media accounts was one creating it and inviting people I already knew and then two pushing out my own video. And again, the fear that embodied you and just choosing to do it scared anyways. And I know one of my friends from high school, so I had another podcast back in the day.

And her sister was listening to that podcast and her sister texted my friend from high school who then texted me, Hey, I want to let you know my sister's been listening to your podcast. And she sent me a text saying, Amanda has gotten so much better. That tells me she's really been on this journey with me and following me. And it made me a little nervous and insecure, but also confident at the same time, like how many people have been following my journey. And then also how cool for them to see that I'm getting better. I'm getting more comfortable in my own skin. I'm starting to fall.

Amanda Escobedo (34:21.346)
figure out my rhythm with this, right? And so it's the same thing too. When I first went networking, I remember one of the first times I went networking, so scared to go to my first event. And part of why I was scared to go to one of my first events is one of the scariest things someone could ask me is, you're a coach. What kind of coach are you? And I didn't really have a great answer. was like,

kind of that transforms lives, you like I wasn't very focused. I wasn't very niche. I was too scared to be niche because I was like, I could really solve any problem you have. And when you're a master of everything, you're a master of none, right? And it just creates so much confusion, but like I had no answer. I didn't know how to respond to that. And I also just felt very scared from the sense of like, it's my first time being like a business owner, a solopreneur going out and meeting all these other business owners. was very intimidated by

lawyers, by business owners, by any of these type of business type industries. I had never really interacted with them. so that was, you know, unpacking my fear with going to a networking event. I realized my mindset is not sustainable. It's definitely not going to help me succeed if I'm walking to these events, feeling scared, feeling embarrassed, feeling nervous around other people. And so I recognized I had to reframe my networking relationship.

So instead of seeing each conversation as a test of me, do they think I'm a legit coach? And so, cause what would happen is, especially in that first event, second event, going out, trying to interact with people, people just felt very confused when they met me. What I mean by confused, they just didn't understand what I was doing, what kind of coach I was, what there's so many people don't even know what a coach does. So imagine all the obstacles is one, there's so many people that don't know what a coach does to

Like if I can solve every problem, that means I can't articulate what problem I'm solving. So every time I meet people and they ask, what do you do? They just looked so confused. And then that was just so defeating for me because I'm like, gosh, I just don't seem legit and I don't come off trustworthy or competent. And so instead of, again, seeing these conversations as evidence of why I'm not a good coach, as evidence of why I suck at this or why I shouldn't do this or not interpreting those interactions as

Amanda Escobedo (36:42.188)
or asking myself, do I seem legit? I started approaching networking a little differently and the approach turned and shifted into a place of this is really just practice for my elevator pitch. So I started to turn networking events into my experimentation. This is an opportunity for me to try new elevator pitches and then see how it lands with people. Is the direction I'm going make sense? Are they starting to nod their heads or things are starting to click?

Or are they still giving me also deer and headlights confused don't understand? So it became more of my experiment. It became more of my data and not proof that I suck, right? And so the kind of the new narratives that started to come with me through this experimentation of networking was, okay, the phrase clearly didn't land as I expected. Maybe my explanation was too vague. Oh, this example really lit them up. I'm a lot closer to the value I'm trying to provide.

And so that dialogue in my head starts to shift a bit and I start to shift out of embarrassment. But again, what I want to highlight is these feelings of embarrassment, these feelings of fear, you're going to have them. Okay. Anything you're doing new and you're putting yourself out there, the brain does not want to be judged by other people. And so in the beginning phase of all this, you're going to be embarrassed. People are probably going to think you look dumb.

But if you have the courage to say it's OK and reframe and start turning these new experiences as an experiment and people's responses as data and information on how you can pivot, that's what's going to cultivate your creative mindset, taking embarrassment as feedback, not as a full stop. And so again, going back to Stuart in his example, he's saying the team should be embarrassed for what they have.

What that tells me is Stuart was embarrassed for what the team had produced. He's leading. He's embarrassed of the type of product that's out in the world today. But he's turning embarrassment into fuel. He's not okay with this outcome. And this is the example of reframing. How can you reframe your relationship? He's not using embarrassment as evidence of this is why I suck. This is why we can't do this. He's using it as fuel.

Amanda Escobedo (39:03.566)
Then with the right team, turned those jaded jab comments from Stewart into fuel as well, into shared ownership, into a challenge, all right, let's do this right together, into playful energy. Now, the other kind of characteristic or note that I wanted to highlight is what I would consider a little bit of the challenger factor in this sense. And so what I mean by that is, you know, this article really touches on this idea that Stewart's direct

criticism could be motivational. And this is where the Challenger Effect comes in. in psychological, if you're familiar with the Challenger Effect, what it's really the Challenger Effect is really about disrupting the status quo. It's about challenging assumptions. It's about being direct and honest about what isn't working. It's about challenging ideas.

Now, what makes the Challenger Effect effective is you do have to have psychological safety. Psychological safety is key. But psychological safety, I have to say, can also be a bit nuanced because depending on how your relationship is, you can actually say almost anything you want to somebody. You just have to deeply know your audience.

And so if there's a foundation of trust already and everyone understands the shared mission, then you might be okay with saying what the team has produced is a piece of shit and they should all be embarrassed because if that tells me that he has some type of trust within that team already and they don't take it personally and they he's challenging what they've produced, he's saying it's not okay. Now, take his same comments as a leader and let him as a leader

say it in a corporation as a CEO of 100,000 employees. I'm going to bet that that CEO, Stewart, of 100,000 employees of a corporation saying that same quote out in the media, our product is a giant piece of shit, that would land very differently in an enterprise corporation. It would be demoralizing, it would be shaming, it would be confusing, but it doesn't land the same way in a startup.

Amanda Escobedo (41:22.092)
And why is that? Well, my personal belief of why it lands a little different in a startup is because people are a lot closer to the founder in a startup. Startups are smaller. Generally, there's an intimate relationship with the whole team. Everybody knows each other. You have direct access to the founder. Whereas in a large corporation of 100,000 employees, you don't have a relationship with the CEO. That's way, you're way too far removed to get to know, and trust that CEO on that level.

And so when you're in this startup in a smaller environment and you know each other intimately, it means you start to know and understand how people think. And this group, if they're there, they're likely aligned with the mission that he has and they're signed up for a fast paced, high intensity environment. their response, you know, printing the quote and plastering it everywhere shows me, you know, we know this doesn't, this sucks. We're on this. We get the standard. Let's go fix it.

And so again, it doesn't mean that it's the best way to challenge the team with these type of comments. Again, I'm not rewarding how Stuart really expressed his frustration, but it's an example to me of the challenger energy inside a specific culture. And through this, example really to me shows what can make this successful. And what do I mean by this? What can make this successful?

Stewart said some defaming comments about the team, but I think what allows the team not to take it personally and allows it to take it as a challenge and as a motivation is there must be some type of high EQ amongst the team as a whole. They must already have a belief of good intent. There must already be relationship building. There must already be curiosity and a shared commitment to the vision. That is the only way that its entire team

is unified by this comment is through the line of EQ belief that he has good intentions, there's some type of relationship building, there's curiosity, curiosity is key here folks, there's a shared commitment to the vision. Without these the critique becomes destructive in this type of environment. With these the critique becomes, with the other side that I just mentioned, know this critique really becomes rocket fuel for the team.

Amanda Escobedo (43:48.239)
Another key characteristic is curiosity and powerful questions. So this is really where we move from the story into practice. What do mean by that? So instead of just hearing this product is terrible. Give me one second. I'm to take a sip of my water.

Amanda Escobedo (44:09.294)
So the product is terrible. A creative and empowered employee or leader can get curious and ask. And so how do I, before I go into the questions, if my boss comes to me on something I built and says, Amanda, the product we've built is terrible. A creative mindset is somebody that gets super curious by that and starts to ask themselves or the other person powerful question. what exactly makes this product bad in our customer eyes?

What are they getting stuck on? What are the top friction points in the experience? What value are we trying to deliver? And where are we really falling short? What would it look like if this product truly delivered the promise we were making? So when you get a critique as such, rather than getting defensive, rather than it should have been shared differently, at the end of the goal, it's feedback. How do we turn the critique into feedback? And feedback

If we're talking about there's two types of feedback, there's feedback of reinforcement, like we need to keep doing what we're doing. And then there's course correction feedback. So in this example, if we're talking about the product is terrible, this is course correction feedback. But how do we course correct? Before you can course correct, you have to respond with curiosity and powerful questions. So again, if my leader is coming to me and saying, this product is terrible.

This is my opportunity. A creative mindset gets curious and responds with open questions, which is, what exactly makes this product bad or in our customer eyes? What are they getting stuck on? What are the friction points in their experience? And then from a founder mindset, similarly, maybe the founder is also thinking and asking, know, what exactly are we overcomplicating in this tech? What are...

or where are we building features for ourselves instead of our users? And if we had to make this maybe 10 times simpler and 10 times more delightful for our customer, what would we change first? There's a variety of questions you can answer. What we're trying to do is trigger reflection. What we're trying to do is trigger the roots of what's not working and then trigger new ideas on how to solve it.

Amanda Escobedo (46:26.668)
These are not yes or no questions, if you've noticed. They're creative catalyst questions. They open space. They invite ideas and they shift people out of a defensive mode and really into a design mode, honestly. And then my second to last note within this story, again, our goal with bringing in this story is to pull out key attributes, characteristics that create, that cultivate creative humans. We're all creative.

really cultivate your creativity inside. I like generally these are key characteristics I see within the startup world. The next characteristic is really from a founder's point of view. It's an obsession. A lot of founders have a strong obsession with their vision. Everything we've talked about, the critique, the discomfort, the embarrassment, it's all rooted in one thing. It's rooted in their obsession with their vision.

Stewart didn't want the team to feel cozy and satisfied. He didn't want them to feel fluffy and good about what they built. No, he wanted them activated. The comments of, is terrible, came from a deep standard of excellence. I know that what this could be, and I'm not going to pretend we are already there.

That's what his comment tells me. Game changers live again in this tension of between. They live in this tension in this world of what is versus what could be. And that gap is extremely uncomfortable for them, but it's also a source of energy. It's a source of momentum and it's where the breakthroughs are born. And then the last but not least is a key characteristic that cultivates creativity.

you didn't know is playfulness. Yes, if you are allowed to have fun, it's not only you're allowed to have fun, having fun is a key ingredient to creativity. And then this example of this story, their playfulness, the team's playfulness, the founders playfulness and playing along with the team, they turn critique into fuel. So the team's reaction again, of printing this quote out and having putting it all along the wall, this

Amanda Escobedo (48:46.118)
paper trail along the walls with this quote, it's more than a funny move. I actually find it as a coping, creative coping from the team. It's humor after a very sharp critique and it's transforming tension into connection. The team took something that could have felt very harsh and they made it memorable. They made it laughable. They made it motivating for themselves.

And that is powerful. That is creativity. That is group flow. That is really what every organization strives for. We don't want individuals, like one individual to be creative. We want group flow. We want the team to be creative. We want them flowing and jiving. And this playfulness is an example of group flow. And when we are in this playful world, this is when the brain starts to open up.

The nervous system starts to relax and this is where we start to create more space for energy ideas, ideating to solving these problems. This is where more reflections start to flow through and teams who can play together, especially after hard feedback are often the ones who can innovate together. So let's bring this all back together. You know, these key characteristics, let's bring them back from Slack and Stuart back to you.

Everything we just talked about, continuous improvement, clear vision, courage to be embarrassed, curiosity, challenger energy, playfulness, these are not qualities reserved for founders or billionaires of organizations. These are human qualities. They are qualities that you all actually already have. The work isn't to get them, isn't to get these type of qualities. The work for you is to help

refine these qualities is to sharpen them so you can activate your full creative potential. And so here's some reflections that I want to leave with you. Number one, one of the first things that you have an action. I'm going to start having action plans for all of you. Number one, you have an action for yourself and the action for yourself is to identify your strengths. What do I mean by that? Well,

Amanda Escobedo (51:07.278)
I want you to think about your career and your current season. So your career or your current season as a whole, whether you're an engineer, whether you're a product manager, a solopreneur, you're an early stage founder, someone with a high side hustle idea, and it's just an idea stage, but you've been sitting with this idea. I want you to ask yourself which of these qualities most natural to you right now and apply it to this

career or business journey you're on. What qualities are your strengths? it continuous improvement? Is it the fact that you have a clear vision? Do you have a positive attitude towards failure? Do you have that challenge your curiosity and energy? Are you obsessive? Are you obsessed with this vision you have? Are you playful? Do you have the courage to be embarrassed?

I'm going to bet you're not a master at any of these. I'm going to bet that you're not even a master at two, but we still want to highlight what are your top two to three that you feel like, okay, maybe I'm not great at all of these, but these are maybe two to three that I'm a little better at. What is that? If I were to look at this myself, my strengths within this are my continuous improvement, my positive attitude towards failure, my courage to be embarrassed.

I do it, I hate it, but I do it. I almost also want to say my obsession with my vision. My clarity of my vision, I would have learned for myself, is clarity of vision gets clear through action. So I'm constantly in this journey of clarity. I think I have clarity and then my clarity gets muddy. But because I'm so obsessed, I'm continuing to move. And that's what really drives my courage to be embarrassed. So maybe if I were to let go of the courage to be embarrassed for a minute,

I'd say one of my strengths is my obsession with my vision and my positive attitude towards failure. The next thing I want you to do is identify your edges. I want you to ask yourself which of these qualities feels least developed in me? Which one do I avoid?

Amanda Escobedo (53:22.53)
Which one feels most uncomfortable or unfamiliar? And I want you to pick your bottom two to three. And so if we go back to the examples, which one do you feel like you suck at? Is it continuous improvement? Is it a clear vision? Is it a positive attitude towards failure? Is it that challenge or curiosity energy? Is it the obsession piece? Playfulness? Is it the courage to be embarrassed? Which ones do you really feel like you suck at?

Pick your bottom three and then from there from your bottom two to three choose one that's really calling your attention. The one that if you worked on it, if you focused on it, if you strengthened it, it would be the biggest difference that made the difference for you. And maybe it's the positive attitude towards failure. Maybe it's you cultivating the courage to be embarrassed. Maybe

It's cultivating the curiosity instead of defensiveness or the self-judgements. Right. And so let's say your edge is a positive attitude towards failure or courage to be embarrassed. These are your low rated ones. From there, we want you to design an experiment for this week. What do I mean by that? Well, what would it look like to set an intentional experiment this week? So if, for example, you're a solopreneur still finding

your elevator pitch, you're still evolving it, you're still trying to figure out and master that elevator pitch. What if this week you go to a networking event and you treat every conversation as practice, not as performance, as practice, as an opportunity to try a new pitch with different people and use their faces, their responses as data, not as proof that you're not good at this.

not as proof and evidence of why you suck and why you shouldn't continue on this journey. No, as data and information on whether your pitch is working or needs to continue to evolve. If you're building a social media presence, as an example, post one video where the goal is not perfection. The goal is reps. The goal is learning. The goal is gathering feedback. If you're doing outbound emails or cold calls,

Amanda Escobedo (55:43.834)
as part of your business development strategy and you're afraid of rejection. Maybe you're just sending a batch of emails with the explicit intention of just saying, hey, I'm here to learn what lands and what doesn't land on these emails. Treat every no. What if you treated every no or every non-response to your batch of emails or your phone calls as market feedback, not as a verdict of your worth? The goal here, people,

is to approach your business, is to approach every circumstance as a scientist. Set your intentions, run your experiments, observe the results, extract the data, and adjust from there. That is how creativity grows. And that is how you become more resilient. And that is how you quietly transform into the game changer that you already are.

That's all I've got for you folks today. My name is Amanda Escobedo and you've been listening to Game Changer. If today sparked any insights, ahas, or appreciations, new perspectives, I'd be so grateful if you left a review and shared this episode with at least three people in your network who are ready to master the inner game and unlock their full potential. Your support helps others discover this resource and invites them.

to be the next game changer. Join me next time for another conversation on leadership, culture, and creating impact that lasts. Thanks for listening.