Anne Jacoby | Designing Organizations and Individuals for Creative Thinking

Srini Rao

Anne, welcome to the Unmistakable Creative. Thanks so much for taking the time to join us.

Anne Jacoby

It's great to be here 

Srini Rao

It is my pleasure to have you here. So I found out about your work by way of your publicist, all of which we will get into. But before we start, I wanted to start asking you what is one of the most important things that you learned from one or both of your parents that have influenced and shaped where you've ended up and what you've done with your life?

Anne Jacoby

Hmm. Well, I'm super close with my parents. I learn something from them all the time. Um, and I think one of the things that I take, especially now that I am a parent, is this concept of letting your kids fail and their support of my stumbling. And I think, you know, one of the things that I, I did early on was really follow my heart in terms of my pursuit of creative expression.

And that meant singing, acting, dancing. I kind of grew up in the theater. I thought I would do it for a lifetime. And I went to Northwestern studied theater there and ended up deciding to drop out because I got my equity card. I thought it was going to, you know, go pro, which I did for awhile, but you can imagine, I know you can relate to this, Rene, right? The parents of, you know, they were public servants. My mom was in education, you know, teacher, principal, you know, CEO of a charter school.

My dad was in social security for his whole career. So they're public servants and here is their child dropping out of Northwestern university, probably not their proudest moment, but they let me, they let me do it and they supported me through that. And they made that, that decision. They let it be mine. And I think that was a really powerful moment in our relationship.

Would I do that again? Maybe not. Would I advise my kids to do that? Maybe not. But I think the unconditional love and letting me kind of stumble my way through it was a really powerful lesson.

Srini Rao

Duh.

Srini Rao

It's funny because you went to business school at Stern, you went to undergrad at Northwestern. I'm like, oh, wow, you went to the two places that I got rejected. I applied to the Northwestern School of Music and didn't get in. But I remember going to Evanston thinking I was like, the weather here sucks. And when I didn't get in, I was like, you know what? That was a blessing in disguise. But this conversation about dropping out, particularly when you go to a place like Northwestern, because I remember having a conversation with my dad about taking a semester off of Berkeley.

Anne Jacoby

Hehehe

Anne Jacoby

It does.

Anne Jacoby

Right.

Srini Rao

so I could go work and my parents were like, we know you well enough to know that if you start making money, you'll never go back. So talking about how you navigate that conversation without them thinking, what the hell are you thinking? Have you lost your mind? You just got into Northwest, you know, you're at Northwestern one of the best schools in the country and you want to drop out.

Anne Jacoby

Yeah.

Anne Jacoby

Yeah, yeah. I mean, gosh, I think the conversation went a little bit like, well, here I am racking up all of this student loan debt. And here I am with the opportunity to, like you said, earn a living, get some money, doing what I want to do. My passion. It's why I'm in school. I was a theater major. And here I was given the opportunity to do it professionally. And I think.

For me, I had such a strong work ethic, and that is something that I got from my parents, no doubt. Just the value of working hard, earning your own path. That opportunity was too compelling. And I think we kind of reached an agreement that, hey, you can always go back. There's always an opportunity to return. I ended up not returning to Northwestern. I got my degree online. But I think that's a great thing.

that was an okay solution in their mind. And they understood that my drive to perform and to do that in the professional setting was such a strong passion that if I had said no to that, that would have been more harmful and more disappointing and more of a, yeah, disappointment, I guess.

Srini Rao

Well, you mentioned that you're a parent now, and this is something I always wonder. I wonder what this will be like when I become a parent, because I think there's sort of two sides to this coin, right, we think about all the things that we won't do that our parents said to us, like, oh, that's one thing I'm never gonna do, because it didn't turn out the way I wanted it to. But I wonder how you think about those things, like, what are the things you think you're not gonna repeat? Because I feel like everybody says that, and apparently they just repeat the same things. Like, I have a friend who's a teenage daughter.

I was like, do you ever find yourself sounding like your parents when you're lecturing your daughter? He was like, now that you mention it, yeah.

Anne Jacoby

It's really tough not to fall into those patterns, Trini. I think that's every parent's just plight. But I think, you know, one thing that I've learned from my kids is just how different they are and how you really have to meet the child and meet every individual where they are. And no two kids are alike. I mean, my sister and I were very different growing up. And my kids are...

quite different as well. And I think just tuning into what their needs are in the moment and writing that out. And sometimes it's not always easy, but just being present is the lesson that I try to take with me.

Srini Rao

It's funny that you say no two kids are the same. And I've been going back to Gabor Marte's book on ADD called Scattered Minds. And one of the things he talks about is no kid is raised by the same two parents, even if they are in the same family because of the life stage that they're at. I realized my sister and I had wildly different upbringings and she probably had a very different experience of navigating the relationship with my parents than I did.

Anne Jacoby

Mmm.

Anne Jacoby

Yeah.

Anne Jacoby

Mm hmm. Yeah, I think that's a really interesting insight. And yeah, I mean, parents have their own stuff going on, you know, to raise kids, especially in the middle of a global pandemic and launch a business and try to stay sane. I mean, that's a tall order for anyone. And we've all learned a lot through this phase in our life and in history.

Srini Rao

Yeah, well, talk to me about what happens after you drop out of Northwestern, because I think that, you know, you and I both know career in the arts, particularly if you're talking about theater or acting, the odds that you're going to be successful are really low.

Anne Jacoby

Yeah.

Srini Rao

You know, like one in a million. I mean, even being an author, the odds are unlikely. I remember asking my editor Stephanie at Penguin once like, what are the odds that somebody gets a book deal? Like how many people want one? And how many people end up here? Because I needed to rub it in my dad's face and say, this is actually harder than it is to get into medical school. He wasn't having any of it, but it was like one in 5,000.

Anne Jacoby

haha

Anne Jacoby

Mm-hmm. Yeah, I mean, I think, you know, for me, I'd been doing it for such a long time since I was a kid. And, you know, I did it professionally in Chicago. I moved to New York, did it professionally there for a while. I was in New York during 9-11, kind of dating myself here. But that was a pivotal moment for me to just kind of zoom out and figure, you know, gosh, someday I really, I want to be able to buy a house. I want to be able to have a family.

There are plenty of performers who end up doing that and they make their way of it. But I just really was craving more stability and a different kind of intellectual stimulation, I guess. So that's kind of when I made my pivot to business and joined a startup. I thought that was more stable. It shows how little I knew about the startup world, but I ended up staying there for over a decade and growing this.

business and scaling it from seven people to thousands. And that was kind of my aha moment that creativity in business is just as applicable as in the arts. So that kind of tapping into your creative thinking is a real skill that's useful. Yeah.

Srini Rao

Yeah. Well, you know, I want to spend a bit more time talking about the time that you spent in theater. There are probably numerous things that come about in terms of navigating profound uncertainty on a day-to-day basis, wondering sometimes, well, how you're going to pay rent the next month, before you hit that point of, okay, I want more stability. How did you manage your psychology and not lose your mind?

Anne Jacoby

Creativity, my friend. That's what we're talking about. And I think, you know, figuring, I mean, gosh, when I was living in New York, I was waiting tables. I was a nanny. I was an executive assistant at a real estate company. I was also performing. I mean, I was wearing all these different hats and was really just, I was a big planner. I still am a big planner. So I think.

If you kind of plan it all out and you figure, okay, this is what I need to do to make this work and to pay my rent and to live in the city, you figure out a way. There's always a way, but you have to have that drive and commitment to find a path, whatever it is.

Srini Rao

Yeah.

Srini Rao

Mm-hmm. Talk to me about the sort of day-to-day discipline and habits that come from being a theatrical performer and how you've applied those in other areas of your life.

Anne Jacoby

and

Yeah, I mean, I write a lot about that now, just the connecting the dots from the arts and what I really learned about collaboration and leadership and building empathy and, you know, a lot of the skills that now apply in the workforce and that are really sought after in today's work environments, I learned from the theater and connecting with lots of different people. You know, I went to the High School for the Arts here in Los Angeles, LACSA, and that was really

an incredible training ground to connect with lots of different creative people to build something of value, you know, and to play off of each other in a way that melded all of our different strengths and backgrounds. I mean, there were folks who, you know, came from very toney neighborhoods and folks who didn't have a home. And having that rich diversity as kind of your palette.

as a teenager was incredibly transformational for me, to just see different ways of living, to experience different humans, and then to come together with a united mission of we're focused on our craft, we're dedicated to building our artistic discipline. It was an incredible experience.

Srini Rao

Yeah. Well, you know, I think that you're very lucky. I mean, I was really fortunate that my parents dragged me around the world, which I thought was a negative until very recently when my sister kind of said, you got to stop complaining about this. And I realized that she was right because they basically taught me to be a citizen of the world. And yet, if you look at the way that we socialize people, we educate people and how people consume content, we basically program people to have these very myopic world views now.

Anne Jacoby

Hahaha

Srini Rao

And you're talking about diversity and being able to collaborate with people from different backgrounds, people with different police systems. How do you bridge that gap from between the myopic viewpoint and having people not get stuck in echo chambers? Because I remember when I wrote my first book, I jokingly always said the title of this book could have just as easily been called Everybody is Full of Shit, even though Penguin wouldn't have published that. But I realized that I just kept seeing this sort of

Anne Jacoby

Hmm.

Anne Jacoby

Yeah.

Srini Rao

myopic worldview over and over again where people would just see something in an echo chamber and then wonder why they couldn't stand out.

Anne Jacoby

Yeah.

Yeah. I mean, I think it comes down to listening. And again, empathy is huge to, to really take, take a moment to walk in someone else's shoes. And to imagine what that must feel like is a really powerful skill and much needed in today's world in business, certainly, but as a citizen of the world, like you say. So I think that really helps. And I think just finding, hey, what do we have in common? How do we.

Find some common ground that really unites us and brings us together. We are different and we want to celebrate that. But let's find that common ground first and build off of that.

Srini Rao

Well, so going back to parenting, I know what Redondo Beach is like. And you went to Northwestern, I went to Berkeley. We both came from fairly privileged circumstances relatively. How do you maintain that sort of diverse worldview in your kids when they're growing up in an environment like the ones they're growing up in?

Anne Jacoby

haha

Anne Jacoby

Yeah, it's, I think that's a constant challenge for any parent. I think, you know, thankfully they can get exposure to different ways of living. You know, due to the pandemic, we haven't really been traveling all that much, but, you know, our hope is that we can travel to lots of different places where they can get a window into that and start to kind of get out of themselves because you're absolutely right, there is an echo chamber, there is kind of a feeling that.

oh everyone lives right by the beach. It's not true. So I think that next step is going to be really important for our family, certainly.

Srini Rao

Yeah. Well, tell me what your sort of low point was when you were in theater that made you finally say, okay, that's it. I am done with this. I need to find something more stable. Like what was the catalyst for that?

Anne Jacoby

Yeah, I mean, I think certainly 9-11 was the start of that catalyst. And I think, you know, they're just reached a point where I could have stuck it out, but I had been doing it for so long that kind of, I wanted a different kind of challenge. And I think, you know, probably like you, Srini Rao, I really, I love to learn. I love challenges. I kind of lean into them. When anything feels comfortable to me, it's time to make a change. So.

I was really looking for, okay, what's my next challenge? What's gonna get me out of my comfort zone? And for me, that was kind of joining a company and trying to figure that out and build this business. And so I liked that, the intellectual challenge of it and needing to get creative and figure out how are we gonna grow this business? But certainly, I mean, there are low points all the time. That was certainly one when the world felt like it was crashing down.

Srini Rao

Yeah. So I've talked to two people who were in New York on 9-11, Emily Fletcher and Susanna Scully, both of who've been guests here. And I think it's one thing for those of us who watched 9-11 unfold on TV versus people who were actually there. And I'm just curious what that day was actually like if you're somebody who's a citizen of New York. Do you remember it in vivid detail? What were you scared of? You know, what was going through your mind?

Anne Jacoby

Hmm.

Anne Jacoby

Yeah, I remember it quite well and I had the presence of mind to kind of write down what I had experienced after the fact as well. I think I got off the F train in SoHo right after the second plane had hit and I just remember kind of walking around the neighborhood. I was walking to the office that I worked at the time and people would kind of watch all these ambulances racing down Broadway.

Just thinking that it was a fire in the building and just I'll never forget that moment of ignorance where we didn't really understand the magnitude of what had happened and people just thought, oh gosh, what a terrible fire. We could see the smoke kind of coming out of the buildings. But you know, I think that day obviously changed everyone's life in some way, touched everyone. But as a New Yorker at the time, it really did bring people together.

kind of an unspoken knowing you just kind of make eye contact with people on the subway that everyone is going through the same thing at the same time. And I think we're experiencing something similar, certainly with the pandemic, where everyone is a bit traumatized from what's happened. So it's an interesting moment.

Srini Rao

Yeah. Did you lose any close friends?

Anne Jacoby

I didn't, thankfully, certainly knew people who were immediately impacted, but I didn't lose anyone that day. I think just reflecting on how that shifted a lot of people's kind of path, a lot of people decided to leave the city, again, similar to the pandemic.

wanted to live every day in a different mode and of ramping up the gratitude and ramping up the presence, just enjoying what we have.

Srini Rao

Yeah. I wonder when you were confronted with the reality of mortality at such an early age, what decisions did you make about how you would live your life going forward?

Anne Jacoby

Yeah, I mean I-

I think, again, I think it's similar to anyone who experiences something pretty shocking like that, a big tragedy that is shared by many people. It does force you to reflect and be really intentional about what you want in life. And, you know, for me, I, again, I wanted that stability. I wanted to be able to have a family, you know, just wanted a little bit more self-direction and control over my destiny. And as a performer...

you're often at the mercy of the casting director or, you know, what, um, you know, what opportunities exist in a certain piece. Uh, it's, it's a lot harder, I think, to chart your own course. And I really craved that, that creative control. So that for me was the pivot to, to business and to, you know, thinking about, um, being part of that corporate world. Um.

You know, for others, it, it steered them in the opposite direction, right? They thought I'm going to live my life. I'm going to be a performer and this is what I'm destined to do. And so they doubled down on that. So I think everyone kind of, um, absorbs that kind of shock in a different way.

Srini Rao

No.

Srini Rao

Yeah. Well, it's kind of funny because you're kind of an opposite of a lot of the people I've interviewed where they all abandoned the corporate world to go do something creative and you basically abandoned something creative to go do something corporate. So I wonder when you are in the early stages, something you mentioned growing something from seven to 1000 people what goes into scaling something to that level.

Anne Jacoby

That's a good one.

Anne Jacoby

Yeah.

Anne Jacoby

Yeah. I mean, it didn't happen overnight. So, uh, you know, it was over the course of many years, but, um, for us, it was really about the culture. And that's the kind of work that I do now is focusing on creative cultures, cultures that want to innovate and to build and to grow. Uh, and that requires a certain mindset among its founders, among its leadership team to

to set the stage where people can bring their fresh ideas, where they're not scared to take risks, and cultivating that kind of environment is really appealing to me. So that's, I think, the secret sauce that we had as we scaled the organization. We certainly made a lot of mistakes along the way. It wasn't a perfect path, but I think being safe to make those...

stumbles and to take risks was how the company was able to succeed is by creating that kind of environment.

Srini Rao

So there are two sides of this coin that I think about. And the reason I wanted to ask about this is because I'm in that process of thinking, how do we grow beyond where we're at? We raised an angel around that a couple of years ago, and now it's just like, OK, where is that lever that's going to get us to, from three people working together to potentially being acquired by a big company? And the thing that I wonder about is that

Anne Jacoby

Mm-hmm.

Anne Jacoby

Yeah.

Srini Rao

While you want to give people the freedom to take creative risks and bring lots of ideas to work, how do you filter that so that you actually stay focused? Because this is fresh in my mind because I've been working on our sort of product roadmap and I remember looking at it with my community manager, it was like, this is way too complicated, there's too many things going on. I'm like, we're going to kill all this stuff. It's killing our focus. And at the same time, to your point, we need that freedom to basically play.

Anne Jacoby

Hmm.

Anne Jacoby

Yeah, it's such an interesting tension. And I think, you know, for us and what I try to help other companies to do is to really have that North star. And I think you, you're onto something where it needs to be simple enough where everyone is clear about the vision, the mission, the organizational purpose. That's gotta be really crystal clear. Um, the values that we express along the way, how we're going to show up for each other. So I think that's a really good place to start.

before starting to scale and bringing more people on because you bring more people on, it becomes more complex. There are lots of different points of view and that's a good thing, but you need to have that North Star established first in order to get everyone aligned.

Srini Rao

Yeah.

Srini Rao

Hmm.

Srini Rao

Well, let's go deeper into each one of these things, vision, purpose, mission, because I think that often these words get thrown around a lot, and they tend to basically just be buzzwords, but if you actually talk to people about these things, they don't actually have a clue. Because I remember the first time I ever interviewed Simon Sinek, he was like, your why is that you're obsessed with people who are good at unusual things. And I was like, that's great, Simon, what the hell am I supposed to do with that? And the funny thing is now 10 years later, it's like,

Anne Jacoby

Yeah.

Anne Jacoby

I'm sorry.

Anne Jacoby

Uh huh.

Srini Rao

Oh my God, every person that has been a guest on this podcast is a reflection of that core idea. And I realized everything we're we do here is driven by this fundamental belief that everybody has a story worth telling. And I was like, that's it. Everything we do needs to be an expression of that core idea. It's taken me a long time to come to that realization. But when you walk people, they're figuring this stuff out, you know, like vision, purpose, mission, all of that. What is involved in this? Because I think that often these are concepts that can be very nebulous.

Anne Jacoby

Yeah.

Anne Jacoby

Yes.

Anne Jacoby

For sure. Yeah. And people have different interpretations of what that whole ecosystem is. I mean, for me, that why is the organizational purpose, right? That's the impact that you have on the world. That's kind of the big, big North Star. And I think that's always a good place to start. The vision and mission is the what and the how. So the vision being this is what we want to become and the how, this is how we're going to get there. That's the mission. And then you kind of think about values. Well, how, you know...

How is it going to show up in our behaviors? What are we going to reward? What are we going to encourage people to do versus we're not going to tolerate that kind of behavior? That's really the values, what you care about. So I think understanding that ecosystem, getting clear about the definition always helps to kind of, OK, we're aligned on what we're trying to develop here. And then again, to your point, Srini Rao, it's about story and really understanding.

Okay, these are the stories of our organization. This is what we really value. This is what we want to celebrate. And this is where it's, it's actually come up. This is how it's lived and getting those stories out of people is a great place to play and to help refine whatever your whole ecosystem of purpose, vision, mission, and values are.

Srini Rao

Well, so one thing that I have noticed with a lot of people that are in our community or even my readers, my listeners, is that they feel that this creative part of them is something that has to be separate from the person that shows up at work. And it's like, oh, this creative thing I do on the side is like, no, that's completely irrelevant to my work. And I've so often found that the things that I have done that have no purpose or end in mind that are just creative things for fun.

have had a massive impact. So the entire visual aesthetic of Unmistakable Creative came from a 30 day project where I tried to teach myself how to draw and realized I couldn't draw. And, but because of that, I started to actually figure out that I could collaborate with other people who could draw. I was like, oh, other people can bring my vision to life even if I can't do this thing that I want to do. But I think that that's, I mean, I'm in, you know, the position to be able to do that because I own my own company and I, you know,

Anne Jacoby

Bye!

Anne Jacoby

Yeah.

Srini Rao

basically the person who gets to make decisions, but I don't think a lot of people feel that freedom.

Anne Jacoby

Yeah, yeah, and this comes down to the culture piece. You know, our leaders creating those spaces for people to play and to do creative thinking and to do deep work. Are you just kind of a task master and everything's just kind of drilling people down, wearing them down versus, okay, protect this, even if it's 15 minutes, honestly, do some creative thinking.

you know, get your ideas out there and have that white space in which to play. I think that's, that happens with great leadership and creative leadership. And to your point, you know, I think not only do people think, Oh, this creative thinking is outside of my work life. A lot of people don't identify with being creative at all. And I think that's a real miss as well. Um, you know, folks who are in finance or, or legal have the misperception that, Oh, are.

our organization or our function is not creative. We're not meant to be creative when in reality, there's always room for incremental improvement and innovation and new ways of doing things. And that's gotta be a muscle that's flexed and practiced and developed. So I think that's pretty important.

Srini Rao

What do you see as the difference between organizations that foster this kind of thinking versus the ones that don't? Because I can tell you every company I work at, I felt like this is a place where I am going to be rewarded for conformity and punished for going out of line.

Anne Jacoby

Oh, that's so sad to me. That's so sad. I mean, there are big differences. And I think you see that in the relationship with customers. You see it in the stories across the organization, across the employee population. I mean, gosh, we're living in a time where if you don't get this right, people have so many choices, they're out the door. And I think one in three.

employees right now are actually engaged at work. So if you're dealing with that kind of backdrop, getting this right and focusing on culture is more important than it ever has been. And there's so much opportunity to make work a place where people can express themselves, where they are bringing their best ideas, but it needs to be intentional. It's not something that you can kind of take for granted and just say, oh yeah, they'll figure it out. To your point, it is a lot about.

top-down conformity and command and control, even though we know that there are better options out there.

Srini Rao

Yeah. Well, so if you want to design an organization that fosters creativity, innovation, creative thinking, and you don't have the pockets of Google where you've got billions of dollars to basically explore that shit crazy ideas like let's go to space, which by the way, I had a friend who's working on a space travel company. He's like, do you know anybody who wants to go to space? I was like, I don't know anybody who wants to go to space because most of the people I know haven't seen enough of the earth yet.

Anne Jacoby

I'm going to go ahead and close the video.

Anne Jacoby

Yeah

Srini Rao

And the more I thought of it, I was like, that just sounds like a really long airplane ride where you actually don't go anywhere. So no offense to people who are interested in space travel, but, um, it just got me thinking about, about that. It was like, that's ridiculous, but to, to what, you know, to the point, you know, if you don't have, you know, Google's resources, how do you foster and design an environment like that intentionally to bring out this kind of thinking in people?

Anne Jacoby

Yeah, well, I think there are a lot of different ways to think about it. And, um, you know, uh, a big thing for me is, is storytelling, you know, getting people comfortable sharing stories of trying new things, um, exercising their growth mindset, and especially for leaders demonstrating things that they did not do well, and that takes a lot of vulnerability and humility and, you know,

Basically the mindset that I don't have to be perfect as a leader, but that's really what employees are craving is this permission to be human and to try things and to ask for help and support among their, their colleagues. And I think that's a really great place to start and it's free, right? You can have a team meeting where, gosh, the last 15 minutes of the meeting, we're going to talk about things that we tried that did not go well, and we're going to support each other to.

extract the learning from that and to do things differently going forward. So that's just one practical thing to put into practice.

Srini Rao

No. You know, you mentioned industries like legal and finance. I did a bunch of interviews with our readers just to kind of understand what their challenges were so we could shape content accordingly. And one of them worked at a law firm. And she left me the question of how can you be creative when you work in an industry that's not? And I thought that is actually a really good question, because a lot of people, I think, when they work in industry that are not sexy or glamorous, they're like, yeah, I work at a law firm. How can I possibly be creative there?

Anne Jacoby

Mm-hmm.

Srini Rao

Given your background and your research, how does that play out in environments that are not quote unquote creative?

Anne Jacoby

Yeah, well, I think again, it's kind of the nomenclature of a law firm isn't creative. I would say a law firm has to be creative. If you have clients who are faced with challenges that have never been faced before and who are trying to negotiate and have mergers, I mean, negotiation is a creative endeavor, right? Finding a path and finding a solution is inherently creative. And I think it's about reframing and reshaping and giving your...

your lawyers the permission to think creatively about how are we going to build our book of business, right? How are we going to acquire new clients or differentiate ourselves from the other white shoe law firm down the street? You know, there are lots of ways to bring creative thinking into those kinds of environments. But I think it takes kind of a reframe reshaping of what the expectations are and really giving yourself permission to do things in a different way. And that's what companies and clients really are after.

Srini Rao

Mm.

Srini Rao

No, well, let's talk about taking a risk because I have seen this pattern over and over again in my life that as people get older, as they become more and more conditioned by the world around them, their tolerance for risk goes down significantly. And it's funny because if you look at the way that we educate, you look at a kindergarten classroom, it's basically a breeding ground for risk. And you look at a college classroom or even an MBA class, it's a breeding ground for conformity.

Anne Jacoby

Hehehe

Anne Jacoby

Yes.

Srini Rao

And so basically you've been taught your entire life to fit in when we live in a world that rewards people for standing out. So how do you rebuild that tolerance for risk both at an individual level and an organizational level.

Anne Jacoby

Yeah, I mean, I think you're really onto something, especially among leaders. And I coach a lot of executives who are faced with that, right? They have a lot to lose. And I think, um, you know, we've kind of seen in this moment in time where. Gosh, global pandemic, we have all these creative constraints put on us. Let's just cling to the status quo, right? Let's cling to what's certain where in reality it's.

It's the big bets of no, let's, let's try something really different and see what our customers think of that. That those are the things that are breakthrough successes. And so I think for the leaders to, to understand and kind of get aligned on the value of trying things in a new way. And it doesn't have to be big, right? It doesn't have to be huge transformational change, but really getting comfortable with incremental improvement and experimentation as part of the.

Anne Jacoby

That's the muscle that we're trying to develop here.

Srini Rao

Yeah, it's funny because I think that people don't see the degrees of risk. When I talk to them about this, like I either have to do this huge thing or nothing at all. And I realized that everything that I've done has been a series of incremental risks where you get feedback. One thing I wonder is when your risk doesn't pay off and it blows up in your face, how do you maintain the guts to do it again?

Anne Jacoby

Mm-hmm.

Anne Jacoby

Yeah, I mean, gosh, a mentor of mine said, if you're not embarrassed by what you did six months ago, then you're not growing fast enough. You know, you kind of owe it to yourself to keep, keep moving forward. And, you know, one thing that I want to add is there's a risk to doing nothing. And I think that opportunity cost is often undervalued, you know, under assessed or under reported where people think, Oh, let's just keep doing what we're doing. There's really a risk in that as well. And so. Being, um,

clear about what are all the choices and yes, there could be something that could blow up in your face, but you could also go under just by doing what you're doing today.

Srini Rao

Yeah, I try to think about risk from a sort of strategic standpoint of OK, look at the downside, look at the upside, be calculated about it, but not reckless. So when you work with people, how do you define the distinction between strategic and reckless risks?

Anne Jacoby

Well, you know, a lot of companies are embracing more data informed business practices, which I think is great. And I think getting the data really listening to customers first, that's a must, right? You can't just, to your point, be reckless. Hey, let's just try this, you know, throw it against the wall and see if it sticks. No, it really should be informed by the data that you're hearing from customers, the research that you've done across other similar industries.

different industries that might apply. I mean, all of that, that planning has to be done in order to, to make that, that safe bet. Absolutely.

Srini Rao

Well, for me, that raises a question about looking at data and making data-driven decisions without compromising the integrity of the creativity. And I'll give you a more specific example to frame it. So one thing that I am known for is turning down very famous people who pitch us to be on the podcast, people that everybody listening to this has heard of. I think I've probably even mentioned that we've turned down Gary Vaynerchuk multiple times. And that's something I'm proud of. And at the same time,

Anne Jacoby

Okay.

Srini Rao

I also know that Jerry Vanerchuck on the podcast would increase our metrics. And I've always had this line of I will never compromise the integrity of the content to in service of the metrics. And sometimes I've had to do that. I will make guess choices. And I'll choose a good story at the cost of our metrics because I felt that in the long run that would matter.

Anne Jacoby

Hmm.

Anne Jacoby

Yeah.

Anne Jacoby

Yeah. It's all about values, right? Um, going back to that. And I think, um, yeah, yeah. But if you think about it, you know, data is only as good as what you have been doing, and I think if you're really trying to do something differently, sometimes you have to look outside of the data set and think, well, what could it look like if we introduce something completely different? And I think that's what's powerful about creativity.

Srini Rao

And at the same time, we're running a business.

Anne Jacoby

is introducing something that's never been done before, something that is an outlier, that's not in the data set. And we need to push ourselves to keep doing that. That's why, um, you know, diversity is so important is you, you need those outliers to put you on a different path.

Srini Rao

Yeah, you know, I think back to this story, and I probably shared this before, where I was watching this documentary about Nike and sweatshops during the Olympics, and there was a journalist who was doing an expose for CBS. And Nike was sponsoring the Olympics that year. And she went through this whole expose, and then CBS killed the story because Nike was sponsoring the Olympics that year.

Anne Jacoby

Mm.

Anne Jacoby

Wow. That's tough.

Srini Rao

And part of me wonders if I was the CEO of CBS, if I would have made the same decision.

Anne Jacoby

Yeah.

Srini Rao

Because at the end of the day, it's like, okay, this is millions of dollars we're talking about from an advertiser or somebody brings in a ton of revenue. And, you know, there's, there's a question of, okay, am I doing something unethical, my compromising my integrity, or am I actually doing what's right for the business?

Anne Jacoby

Mm-hmm

Anne Jacoby

Right. These are not easy decisions to make, you know, but...

Anne Jacoby

Yeah, that's a tough one.

Srini Rao

Yeah.

So where do people get this wrong? When you work with leaders, where have you seen them do things wrong that actually kill creativity in organizations?

Anne Jacoby

Oh gosh. I mean, your point about conformity really rings true. I think one of the dangerous things is leading by fear and kind of setting that tone where people are really afraid to step out of what they've been doing. They're overly cautious about introducing their ideas.

I mean, that's a big creativity killer. So I think that's a big one is just that psychological safety that's been either cultivated in the team or, or not. Um, so that's a big watch out. Um, and then I think, you know, what I see often is just over engineering where, you know, people are not robots or machines and I'm all for process, but you need to give people a container in which to play and, and allow them.

Srini Rao

Mm-hmm.

Srini Rao

Yeah.

Anne Jacoby

to do things their own way and make it much more, you know, more why, less how, people will figure out their own how, how they're going to get it done. If you're really clear about the why, that's what's most important. And I think leaning into that is a better way to bring out creativity across the team.

Srini Rao

Mm-hmm.

Srini Rao

Yeah. One other thing I wonder is how organizations end up becoming less creative as they get bigger. Because I was going back through Salim Ismail's book, Exponential Organizations, and he talks about Kelly Johnson's Skunk Works, which was like this thing that started at Lockheed, God knows how many years ago. And I remember pulling the essay on Fall Rules and they intentionally kept Skunk Works separate from the rest of the company because like if it

Anne Jacoby

Mm-hmm.

Srini Rao

the rest of the companies involved in this, nothing will come out of here that's interesting or innovative because they'll kill it with bureaucracy. And how, so as an organization scales and gets bigger, to your point, I have a lot more to lose now than I did when I first started the show and started the business. And so my risks have a very different consequence if they don't work. And at the same time, the very things that got me into this position are the risks that I took. So it's this chicken and egg problem.

Anne Jacoby

Ha ha.

Anne Jacoby

Mm-hmm.

Anne Jacoby

Yeah. I love that book, by the way. You know, I think Jennifer Mueller talks about creative blockers and it's a really interesting concept where you have to make sure that creative ideas have a chance to flow up through the organization and that you're really aware of the folks who are either green lighting them or blocking them. And a lot of times with the best intentions,

People will say no to ideas that are creative because they look foreign and different and it's uncomfortable, right? It's something you've never seen before. And so to your point about risk, they're not willing to take that risk and try it out and it just dies before it even has a chance to be experimented with. So I think being really mindful of, okay, where are our gatekeepers for creative ideas across the organization and how are we

allowing folks at all levels to introduce new ideas in a way that sometimes is anonymous. So you're not attaching, okay, an intern suggested this, we're going to say no, it's anonymous. We're going to look at the idea in isolation. I think that's also a really important technique for businesses is to have that objectivity a little bit.

Srini Rao

No.

Srini Rao

Well, I want to kind of bring this full circle. We started out talking about where we went to college, Northwestern, Berkeley, and then, you know, obviously you went to NYU Stern, and I went to business school, and we're talking about the fact that so many people are trained to be taskmasters, and I don't.

Anne Jacoby

Haha.

Srini Rao

honestly think that business school prepares anybody to run a business. I think that I even had an article titled business school teaches you nothing about running a business because I realized it doesn't. It teaches you how to be an employee in somebody else's. So when you think about sort of how we are going to educate people for the future, particularly given your background in the work that you do and having gone to two elite universities, what would you change about the way that we educate people?

Anne Jacoby

Oh gosh, and this rings true as a parent as well. You know, I think about my daughter. Yeah. And when my daughter started kindergarten, I remember her reflecting and saying, gosh, mom, you know, it's just so structured for her as a kindergartener at five years old to recognize, well, gosh, you know, you have to sit at this time and you have to do this at this time. Obviously there are alternate schools out there that teach in a very different way. But I think to your point about.

Srini Rao

That's why I asked the question.

Anne Jacoby

entrepreneurs and how do you cultivate those skills? I'm a big fan of kind of incubation labs and learning labs. I'm an advisor to a venture firm called Dangerous Ventures. And they're really trying to tap into what are the skills that help entrepreneurs to thrive and to be successful. Really thinking about the competencies required and how do we cultivate those.

and get folks to practice those. It has nothing to do with school. I couldn't agree more, Srini Rao, that going to Stern, it was not how I got my business chops. It was really by trial and error and seeing, oh gosh, this works, or I'm well-networked and I know these people, and that really helps me to connect the dots. And I think it's a lot more about lived experience.

Srini Rao

Yeah.

Well, you know, I think Navarra Avikant had a really good way of expressing this. He did this podcast titled how to get rich without getting lucky. And funny enough, I don't listen to podcasts at all, but I have listened to that dozens of times. And one of the things that he said was that there are idiosyncrasies that express themselves in, you know, practice that don't in theory. And I thought about that from the standpoint of sort of like a business school case study, I was like, yeah, in a business school case study, the people are static. They don't, you know, waver between being gigantic assholes.

Anne Jacoby

Yeah.

Srini Rao

the nicest people in the world are being, you know, brilliant and complete morons.

Anne Jacoby

Right. Yeah, that's so true. You know, I love kind of role plays as well as a way to learn and to really, it's probably back to my acting roots, but just kind of embodying, okay, these are the set of circumstances. How would you really behave under these conditions? And let's play it out and let's try it on. And you can really learn a lot from those exchanges. Yeah.

Srini Rao

So two sort of final questions, like when people come to you to hire you and ask you to come into an organization, what are the problems that they're asking yourself? Like why does somebody typically come to you and what are they looking for?

Anne Jacoby

Yeah, I mean, I think a lot of organizations are trying to figure out how do we create the culture that we want under these sets of circumstances that we never predicted. You know, folks who are moving to more of a hybrid setting or going completely remote and how do we preserve and really strengthen our culture under these conditions. So a lot of the time we're thinking through...

What's the strategy to, to ensure that our culture can thrive, that people can build the skills and relationships to feel connected to the organization and that they're given the tools to really innovate and bring their creative thinking to the workplace. So that could be a small company that's really just, you know, hyper growth, trying to figure it out. They're hiring a lot of people and it can be also a large organization that's trying to ensure that their culture is.

is ethical and strong under these conditions.

Srini Rao

So I know I said I had two more questions. I guess it was three because this is actually one thing I've wondered a lot about ever since I left the corporate world. I mean, I was a terrible employee. And I was constantly being put on performance improvement plans. It's no surprise that I didn't work out. But one thing that I kept coming back to was this idea of mismatching talent with environment that I just kept seeing over and over again. And I thought to myself, if somebody had put me in a different job, I probably would have thrived.

I always jokingly say, I was like, performance improvement plans don't improve performance. They prevent wrongful termination lawsuits. And it's true, honestly, I don't know anybody, I don't ever remember getting off of one of those plans and thinking, oh, now my job is safe. Most of the time it was like, I'm on this performance improvement plan. I got three weeks to find a new job.

Anne Jacoby

Hahaha.

Anne Jacoby

Aw.

Srini Rao

And I looked back at it and said, you know, rather than saying, OK, like this person is underperforming, there's no question. There's never a question as to whether this person is in the right role to begin with. Have we aligned their strengths with the job that they're doing?

Anne Jacoby

Yeah, yeah, it's such a powerful insight. And I think, you know, there are some organizations that really lean into that and who are open to shuffling people around and are really thinking about skills and strengths to your point. And some that are just not set up for that, which is a shame because, you know, the talent that you have within your organization, they're right there, you know? And if you can tap into that potential and to develop it in the right way.

I believe you can really help the organization to go in the right direction, but you're right. Sometimes they're just sitting in the wrong seat.

Srini Rao

Yeah, I was telling a friend the other day, I said, if I went back to corporate now, one of two things would happen. I'd get promoted in the first week or I'd get fired on the first day. I mean, because I have like so many data points from having had thousands of conversations on this podcast with people that I'd probably see things that most people can't. And I would either go too fast for most people and then look like I'm doing nothing or I'd get fired on day one.

Anne Jacoby

That's right.

Anne Jacoby

Yeah.

Anne Jacoby

Well, you're going in with the right kind of expectations, I guess.

Srini Rao

Yeah, yeah, absolutely. Well, this has been really fascinating. I have one final question for you, which is how we finish all of our interviews. What do you think it is that makes somebody or something unmistakable?

Anne Jacoby

Yeah.

Anne Jacoby

Well, I mean, I think that someone who can tap into creativity and be completely themselves unapologetically makes them pretty unmistakable. And that means being perfectly imperfect. And I think our world needs a lot more of that.

Srini Rao

Amazing. Well, I can't thank you enough for taking the time to join us and share your wisdom and your insights with our listeners. Where can people find out more about you, your work and everything that you're up to?

Anne Jacoby

Yeah, you can check me out. I'm on Instagram at Ann Jacoby dot author. And then, uh, my website is spring street co.com.

Srini Rao

Amazing. And for everybody listening, we will wrap the show with that. Awesome. Yeah, my pleasure. That was super fun.

Anne Jacoby

Thanks, Street.