Why Execution Matters More Than The Right Idea with Issa Rae

Summary

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Aspire with Emma Grede

Episode: "Why Execution Matters More Than The Right Idea with Issa Rae"
Date: February 10, 2026
Host: Emma Grede
Guest: Issa Rae

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Episode Overview

In this illuminating conversation, Emma Grede sits down with acclaimed creator, entrepreneur, and actress Issa Rae to explore why flawless execution outweighs just having a great idea, and what it truly means to build a business—and a life—that reflects your ambition and values. Issa opens up about career pivots, creative risks, entrepreneurship outside Hollywood, the tension between visibility and power, money’s evolving role in her life, and the challenge of sustaining innovation and authenticity as her empire grows. The episode is rich with Issa’s signature candor, humor, and self-awareness, offering inspiration to creatives, founders, and anyone balancing ambition with self-reflection.

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Key Discussion Points & Insights

1. A Season of "New Beginnings" for Issa Rae

[04:31-05:27]

• Issa reflects on her transition from HBO to a new partnership with Paramount, describing this period as a "new beginning."

  • “It just feels like new opportunities, new horizons, and I’m kind of in this humble period where I’m proving myself again … it feels like a show and prove season in a new way.” (Issa Rae, 05:04)

• Despite past success, Issa continues to seek new challenges:

  • “I want to prove myself in new mediums. I want to prove myself in the work that I do. I’ve been writing a lot more and also just kind of taking a step back in certain areas.” (Issa Rae, 05:30)

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2. Ownership, Ambition & Finding Balance

[06:22-10:06]

• Ownership is critical to Issa:

  • “Ownership allows that. I hate, especially now, especially how volatile the industry is ... I need to feel like I’m in control of my own destiny.” (Issa Rae, 06:34)

• Ambition vs. creative necessity:

  • “I don’t want to feel like I’m doing the same thing over again. I love a routine, but I don’t want to feel like it’s work and I know what to expect every day.” (Issa Rae, 06:03)

• Challenges of work/life balance and recognizing a new personal ambition:

  • “I have been so ambit on the work side … and then I haven’t put as much focus on my personal side in the same way … That balance and trying to figure that out is something I’ve been like, oh, I don’t do it well … but now I actually care.” (Issa Rae, 09:06)

• On the possibility of motherhood and not forcing life’s timing.

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3. The Early Grind & Embracing Failure

[11:33-14:38]

• Issa details her long path to Insecure—early web series, failed pilots, and how setbacks (like missing out on a Shondaland project) taught resilience:
  • “I pitched a show for ABC and their development team … I approached it with the ‘what can I make for you?’ mindset, as opposed to what do I want to make … the ABC ended up passing on the project and I was like, I blew my one shot.” (Issa Rae, 13:31)
• Honest about fear and self-doubt, she describes the crucial moment when HBO called, leading to her breakthrough.

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4. Navigating Success & Staying Grounded

[15:37-19:07]

• Issa reveals she’s never really felt like a “star”:

  • “I’m always on the other side of just like, oh, when’s this gonna go away … This won’t last. Nothing lasts. And I’m very cognizant of that.” (Issa Rae, 15:49)

• Diversification and building an empire:

  • Issa discusses her ventures beyond television—consumer goods, restaurants, coffee shops—motivated by genuine passion and not a desire to do “just anything for a check.” (18:33)

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5. Creative Control, Hands-on Leadership & Execution

[19:07-20:26]

• Issa values being hands-on, editing projects herself, and finds delegating challenging:
  • “More people doesn’t mean it gets done faster. It means it’s just more people.” (Issa Rae, 20:26)
• Relishes getting her hands dirty and never wants to lose the “DIY” spirit she had making Awkward Black Girl.

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6. Visibility Versus Power, Decision-Making, and Industry Gatekeeping

[20:26-25:22]

• On the difference between having visibility and having real influence:
  • “There’s just so much power in just quietly doing. When things are ready, I love popping out with something finished.” (Issa Rae, 20:38)
• Emma and Issa discuss the often invisible nature of decision-making in Hollywood:
  • “The decision making was in the hands of one person’s taste … the things that I really, really wanna make on a large scale, I can’t make because of that.” (Issa Rae, 25:22)

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7. Gatekeeping, Gratitude, and the Business of Creativity

[26:34-29:52]

• Navigating gratitude, access, and when executives expect creators to be thankful for opportunities, not recognizing the value talent brings.
  • “I can realize. I’m happy to realize that. And it kind of made me disconnect and also, in a hardened way, look at myself as a product.” (Issa Rae, 26:46)
• Learning to balance creative instincts with market realities and audience testing, especially in film.

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8. Leadership Style and Growth as a Businesswoman

[30:19-32:20]

• Issa on being a collaborative, solution- and kindness-oriented leader:
  • “Everybody who’s a part of something for the most part wants it to be good … Unless someone is outwardly disrespectful to me, then I won’t return that energy.” (Issa Rae, 30:41)

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9. Leveraging Power, Black Representation, and DEI Rollbacks

[32:50-36:49]

• Issa acknowledges using her power more confidently, especially as she witnesses a cultural and institutional rollback of diversity efforts:
  • “I used to tiptoe a lot … Now that I’m like a business, I’m just like, yo, business gotta get done.” (Issa Rae, 32:50)
• She addresses the simplicity of DEI:
  • “Just look around and think about if it replicates what you see in the real world, honestly, which feels so simple.” (Issa Rae, 36:18)

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10. Money: Evolving Relationship and Financial Intentionality

[38:03-43:13]

• Issa is candid about money’s importance now:
  • “You have to have money. Like you just. You do. You have to be able to self finance, to be able to take risks ... Money matters.” (Issa Rae, 38:29)
• Has become less anxious, more intentional, and admits to being “so frugal”—preferring to spend on food, travel, and experiences.
  • “Just ‘cause I have it doesn’t mean I need to spend it.” (Issa Rae, 41:57)
• Advice for women: invest in yourself, but balance self-care with caring for others.

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11. Protecting Creative Flow & Scaling an Enterprise

[45:38-48:01]

• Issa credits trusted collaboration and hiring a COO for freeing up creative bandwidth:
  • “I needed focus … the best thing that I ever did was hiring a COO ... because a lot of my day was wrapped in meetings and managing the company.” (Issa Rae, 46:49)

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12. Boundaries, Prolific Output & Learning Discernment

[50:50-53:47]

• Current goal: to be “more prolific”—more movies, TV, digital projects and to be less accessible in order to preserve creative drive.
• Uses opportunity cost to decide where to put her time; only works on projects she’s genuinely passionate about.

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13. Legacy, Mortality, and Lasting Impact

[60:58-64:56]

• Issa speaks candidly on mortality as a motivator and her vision for legacy:
  • “When you love your life, you’re gonna think about death, you know … my happiness does come from … creating things, whether that is creating the life that I want, whether that’s creating your favorite shit, maybe creating a family.” (Issa Rae, 61:18 & 60:13)
• She wants to be remembered for who she was as a person, not just for her work.

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14. Enterprise Mentality versus Loyalty; Lessons on Firing & Execution

[67:55-73:55]

• Issa admits her biggest business challenge is giving too many chances out of loyalty, especially to creatives.
• Emma reinforces having an “enterprise mentality”—making decisions for the good of the business, not just individuals.
• Issa’s core lesson: “I don’t give a fuck about your idea if you’re not the person to get it done … I need executors.” (Issa Rae, 70:49)

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15. Advice to Women & Aspiring Creatives

[74:11-75:58]

• Encourages women to trust themselves and know their strengths:
  • “Always remember why you belong in certain spaces, what your strengths are … I am fucking good at this. No one can ever take this away from me … I know what I’m really, really good at … and also don’t be afraid to ask about what you don’t know.” (Issa Rae, 75:58)

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Notable Quotes & Memorable Moments

• On New Beginnings and Reinvention
  “I feel like it feels like a new beginning in so many ways… it just feels like new opportunities, new horizons, and I’m kind of in this humble period where I’m, like, proving myself again.” (Issa Rae, 04:35)

• On Ownership & Control
  “I need to feel like I’m in control of my own destiny. And ownership allows that.” (Issa Rae, 06:34)

• Creative Burnout and Change
  “I don’t want to feel stuck in any one place, and I don’t want to feel like I’m doing the same thing over again.” (Issa Rae, 06:03)

• On Failure & Learning
  “I approached it with the ‘what can I make for you’ mindset, as opposed to what do I want to make and what’s my voice? … they had wanted to work with me because of my voice.” (Issa Rae, 13:31)

• Visibility versus Power
  “There’s so much power in just quietly doing. And when things are ready, like, I just, I love popping out with something finished that I want people to see.” (Issa Rae, 20:38)

• Gatekeeping
  “What I wanted to make was in the hands of one person … I’m beholden to a singular person’s taste.” (Issa Rae, 25:22)

• On Leadership
  “Everybody who’s a part of something for the most part wants it to be good and wants to do a good job. And so talking to people like they don’t want that is, like, everybody loses.” (Issa Rae, 30:41)

• On Money & Financial Power
  “You have to have money. You have to be able to self-finance, to be able to take risks … If I don’t have the means to pay people to get things done, then I will suffocate.” (Issa Rae, 38:29)

• Enterprise Mentality
  “I don’t give a fuck about your idea if you’re not the person to get it done.” (Issa Rae, 70:49)

• Trusting Yourself & Moving Forward
  “Always remember why you belong in certain spaces, what your strengths are … I am fucking good at this. No one can ever take this away from me.” (Issa Rae, 75:58)

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Timestamps for Key Segments

• Issa describes her current chapter as “new beginnings”: [04:31]
• Importance of ownership and creative control: [06:22]
• On balancing personal ambition and work: [09:06]
• Early rejection—learning from Shondaland/ABC failure: [13:31]
• Feeling like a star? “No.”: [15:49]
• Building an empire beyond film & TV: [16:53]
• Why execution trumps ideas, and the need for self-reliance in projects: [19:07], [70:49]
• Visibility vs. power and industry gatekeeping: [20:26], [25:22]
• Experiences with DEI rollback in Hollywood: [32:50], [36:18]
• Evolving relationship with money: [38:29]
• Hiring a COO to sustain growth and protect creative bandwidth: [46:49]
• Learning to say no, opportunity cost, and project selection: [51:54]
• On mortality and legacy: [61:03]
• Advice to women: trust yourself and protect your core strength: [74:11], [75:58]

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Emma’s Rapid-Fire Questions (Selected Highlights)

• Favorite comfort TV: Any dating reality show—Love Island (US), Ultimatum. (77:05)
• Song for this chapter: Elmin’s "Reclusive"—captures her mood of intentional withdrawal and focus. (78:02)
• Genre Issa wants to explore: Grounded sci-fi/dystopian drama. (78:45)
• Book that changed her life: "The Courage to Be Disliked." (79:11)
• Aspiration she no longer holds: “Going to industry parties. I don’t … I’d rather stay at home.” (79:25)

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Episode Summary Takeaway

This episode is a masterclass in controlled ambition, resilience in the face of rejection, and the nuts-and-bolts reality of making things happen—and last—in any industry. Issa Rae’s practical wisdom about the necessity of execution, her honest admission of self-doubt, and her unwavering commitment to authenticity and meaningful ownership offer listeners a rare, empowering roadmap for carving out not just success, but significance.

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Transcript

[A]

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[B]

Thank you. I'm happy to be here. Thank you for having me.

[A]

I'm a huge fan. I have to say, I feel like I've watched every single Insecure episode maybe five times over. Like, I'm in.

[B]

You know it better than I do. I thank you for that.

[A]

No, I really do. I was dedicated to that show in such a big way, but I really wanted you to come here today. And I have to say, I've been handing your team since I started this. I was like, issa, Isa Issa. Because, listen, I follow you, I've been tracking you and it feels to me like you are building somewhat of an empire. And I feel like people think they know you. They think they know exactly what you're up to. But I wanted to ask you, when you look at this chapter of your life, how would you describe it right now?

[B]

You're catching me at such a weird time.

[A]

Tell me about that.

[B]

I feel like it feels like a new beginning in so many ways. I know, I know, I know. But bear with me. Like, I've been with, you know, the same company for the last 10 years. Maybe Insecure came out in 2016. Yeah, say that long ago. Yeah, it came out in 2016, the end of 2016. And now, like, I've moved on to a new home with Paramount. And congratulations, by the way.

[A]

Big deal out there.

[B]

Thank you. It's really, really exciting. And I'm still, you know, I Love hbo. I'm still doing business with them, but, like, it just feels like new opportunities, new horizons, and I'm kind of in this, like, humble period where I'm, like, proving myself again. So the chapter feels like, yeah, New Beginnings is the right thing. And I was telling the company that it feels like a show and prove season in a new way.

[A]

You still feel like you have to prove yourself.

[B]

Yeah, but I'm happy to, like, I want to prove myself in new mediums. I want to prove myself in the work that I do. I've been writing a lot more and also just kind of taking step back, a step back in certain areas. So I'm just reevaluating where I am, but in an exciting way and just trying not to allow myself to feel too comfortable with the direction that I've taken, you know?

[A]

Is that, like, out of creative necessity or is that because you're so ambitious?

[B]

Both. Yeah. When you say necessity, that resonates with me specifically, just because, like, I. I don't want to feel stuck in any one place, and I don't want to feel like I'm doing the same thing over again. I love a routine, but I don't want to feel like it's work and I know what to expect every day.

[A]

Yeah, fair enough. I mean, your work has always had a very particular and specific point of view. And I guess my question to you is, like, how important has the sense of ownership been to you?

[B]

So important, because, you know, like, ownership, you kind of get to dictate your. Your path and you get to. You run the show. I'm a bossy bitch. Like, I've been that way since I was young. And I don't mean it in, like, the Khalees way. Like I'm bossy. I mean, like, I need to feel like I'm in control of my own destiny. And ownership allows that. I hate, especially now, especially how volatile the industry is. And it doesn't kind of know what it wants to be and who it's serving. I'm very certain of that. And to be able to own that narrative and own what I make and own that lane is really important to me.

[A]

I want to kind of take it back a little bit and understand why, what, like, what made you the woman that you are today. So kind of going back to your childhood, I wonder, like, what part of the little girl is still inside you now? That little girl growing up, the sixth.

[B]

Grade girl, is very much in there in the sixth grade. I don't know about you. Did you ever have an awkward phase in your life.

[A]

Yeah, I had an awkward phase. You think I grew up with this glam on this face? So the sixth grade means I grew into these lips. I did grow into this head.

[B]

Well, girl say that 11 year old is in me. And I think it's just, there's just an awareness and you know, that like any part, any insecurity that remains, any discomfort, discomfort that I associate with the little girl, me, but then the imaginative side where you're just like, that person thought anything was possible. That person was like, just wait till I grow up. And I still feel like, just wait till I grow up. Even though, you know, I'm grown. But yeah, in some ways I miss not having that fear. I miss not having any expectations but my own. And yeah, like, I like to play and have a good time. Though recently I've been so. I don't know, I don't know what's up with me right now.

[A]

What is up with you?

[B]

I know, tell me, tell me, diagnose.

[A]

Me, tell me, give me the problems, like what's happening in that head of yours. I feel like you're on top of the world. If I was diagnosing you, I'd feel like, you know, she's just sitting back looking pretty with the deals flowing in and the offers happening and you know, looking back at her work going, I did that.

[B]

That's very much it. But I also feel like there's something missing that I haven't put my finger on yet.

[A]

Oh yeah, that's interesting. Yeah, you really are ambitious. You feel like it's a work thing or it's personal.

[B]

It might be personal. I feel like the work thing I feel good about. It's definitely on the personal side. And I think I'm wrapping because that is a thing. Oh, I think I just cracked it. Thank you so much. You helped. I feel like I have been so ambit on the work side and a lot of those things I feel like I'm achieving and then I haven't put as much focus on my personal side in the same way that I should and want to. And that has been an intention this year. So that balance and trying to figure that out and juggle, that is something I've been like, oh, I don't do it well. I don't get who cares? But now I actually care. Whenever someone asks me like, how do you juggle your work life and your personal life? I'm like, I don't, I don't, I don't know how to. And even Hearing you talk about, like, your. Your process when you go home. Like, you're. You have this family that you're able to tend to, and I'm. I'm just like, I don't know what that is yet. What I'm. What I'm. What I'm striving for on the personal side yet. But I'll figure it out.

[A]

I'm sure you'll figure it out. Do you feel like you want to be a mom?

[B]

I do. I do. I do. But I. Only if it's. If it's. If it's meant for me. No, I feel that sometimes I'm like, I don't want to force it. Like, if I were to find out right now that I was. I'd be.

[A]

Like, you said, we have spots for you.

[B]

If I were to find out right now that I was pregnant, I would be like, oh, no, I'm not ready yet, but in the future.

[A]

Yeah, no, and listen, I feel that and understand it deeply. I think it's kind of amazing that you admit that, because as an ambitious woman, I mean, listen, I feel like I spent my entire twenties trying not to get pregnant. I was just like, keep every baby away from me, right? It was like that part like this. And then all of a sudden, you know, like, something hits you and you're like, oh, I just want a baby and I can't think about anything else. But I feel like, you know, when, you know, and it is the curse of ambition, right? It's like you have to, you know, figure out what's going to come first. And especially in the entertainment industry, like, your time, like, you don't choose your timing. The time chooses you. Because, well, you were working. I mean, you had this incredible YouTube series you were killing. And, you know, all of a sudden, to the rest of us, it appeared you were plucked out of obscurity and suddenly you were on our TVs. I'm pretty sure there was some work that led up to that moment.

[B]

Absolutely. As you know. Yeah, it's been. It's been a long time in the making. And, yeah, Even before that YouTube series, the people knew there were two other ones that I wasn't in, but that I was still, like, working and grinding towards. But to your point, it has been just a constant, constant grind that I love, but there also has to be more in a different kind of balance. I don't want to, like, grind it out for nothing. Fair.

[A]

Grind it out for nothing is not the thing. Talk to me about your creative process, because I feel like you know, you're a. I mean, I assume that you are a writer and an actress first and foremost. Like, talk to me about the early days, like, what came before Insecure.

[B]

Oh, man. Before Insecure, I wanted to be a writer. I wanted to be a filmmaker. And, you know, I was entering contests. I entered a Sundance writing contest with a friend, and we were semifinalists. And I just wanted to make the movies that I love that weren't in theaters anymore. You know, like the Love Joneses and the Love and Basketballs, like, all those disappeared. And I was like, I wanna make those. Those movies make me feel way. And then I started making web series when I went to LA and tried to sell those movies that I was talking about, and there just wasn't an audience for them. And so I would just dabble with trying to make an audience online. And that turned into, like, I really like doing this, and now I' a following and I kind of just want to create for online until the right opportunity comes along. And then a few right opportunities came along that I fucked up.

[A]

Thanks for telling us that for sure. Please say more.

[B]

I mean, I'm very candid about an ABC opportunity with Shondaland, Shonda Rhimes company that I just wasn't ready for creatively because I was too scared.

[A]

Like, you were offered something and decided not to do it.

[B]

I had pilot opportunity. I pitched a show for them for abc and their development team was so great in terms of, like, holding my hand through the pilot process, because despite wanting to be a filmmaker, despite writing for my own web series, I had never really written a TV show before and much less like a network pilot. And so I was also such a fan of Shonda and everything that she was building, she has built over time. But to witness that firsthand, like I was in their offices working with their development team, it was just so cool. And I approached it with the what can I make for you? Mindset, as opposed to what do I want to make and what's my voice? And I forgot that in that process, like, they had wanted to work with me because of my voice. And so that process was just. I describe it as I turned in kind of like mush at the end of the day because I didn't know it was just voiceless, voiceless material because I didn't have a pov. And so, yeah, the ABC ended up passing on the project and I was like, I blew my one shot. And then HBO called after that to. To just see what I had.

[A]

What did it feel like emotionally? Like that waiting period between, you know, when you had the YouTube series to the ABC thing not working out, and then, you know, getting insecure, you know, going through hbo, like, what was that like for you?

[B]

The most anxious I ever felt was the waiting period to get the pilot for. To get the green light to shoot the pilot. That was such a long process. And that felt like literally my last chance to do. Cause again, I was now at my dream network. HBO gave me a chance to do another draft. And that's when I was like, I'm just gonna make it as raw as I can. Kind of reworked some things. Reworked a lot of things, and then just sat there like, I hope they say yes. And I remember the day I got the email that we were gonna be able to shoot a pilot, and I was like, I'm not gonna fuck this up.

[A]

And you didn't. You went in. Did it get to you at all? Were you like, I'm a star now?

[B]

No, no, no.

[A]

At what point did you start feeling like a star? I'm so interested.

[B]

I don't. I've never felt that way. I've never felt like I'm a star.

[A]

Yeah.

[B]

Do people feel that way?

[A]

Like, I'm sure they do. I'm sure, like, you know. Yeah, I'm sure they do.

[B]

No, I'm always on the other side of just like, oh, when's this gonna go away? Like, let's let me take advantage of it right now. Cause this will. This. It won't last. Nothing lasts. And I'm very cognizant of that. So for me, I'm always like, okay, what'? And how do I keep this going so that I can do the next thing? But, no, I've never.

[A]

Well, it's so interesting to me because, I mean, it's so clear that you have been able to leverage the success of that show and what it brought you as an individual, as a businesswoman. Because, again, and I will say this, I look at you and I'm like, she's building an empire. And I want to understand, like, why it's been important to you to have this diversification. Is it the fact that you can or did you always have this plan because you have gone into so many areas outside of entertainment in consumer goods and hair. You know, you've got this, like, burgeoning kind of restaurant empire that's happening. Will you talk a little bit about that side of things?

[B]

Yeah. It comes from having multiple passions and, you know, feeling like I didn't want to be kind of like, what I was talking about earlier, stuck in one place. Like, I love creating. Like, that is what I love the most. But I also always wanted a coffee shop. I also love the restaurant industry. I love to eat, I love to serve. I love these things. So these are, like, passion projects for me. And to your point, I wanted to leverage the opportunity to work with people I'm fans of, to collaborate with them to make these other passion projects or side quest work. And, yeah, it was just a matter of, like, not trying to limit myself and make sure. Making sure that it made sense that, like, my main business could support the other businesses. Otherwise, nothing works. And that's also something that I'm realizing, I've been realizing over the last year, where as much as I want to be, like, behind the scenes, I also have to be visible for these businesses to work, which is.

[A]

Damn right.

[B]

You're like, yeah, girl. I'm like, yeah, I know.

[A]

Get out there.

[B]

And that is. That's something I'm navigating because sometimes I just. I don't be. Want to be, like, right now. I've been off social media since the first, and it's a dream, you know, you have. I love taking breaks. I don't. I don't want to, but you have to. My most feared phrase about myself is, issa, just be doing anything. Like, that would be like, oh, no. Is that what you think? And I don't want to feel that way about myself. Like, it doesn't make sense. Like. Or I did it for the check. You know, like that. I say, no.

[A]

You ever do it for the check?

[B]

No. And my manager can tell you that. He'd be like, come on. It's like, just take it. It's a lot. It's a lot. You sure? And I'm like, no, I would rather not. No. Cause I wouldn't again. I would show up dreading it. And I don't like the feeling of, like, this doesn't feel right. Yeah, I'm impulsive. That I feel like is my best and worst quality. It's my worst quality because I don't ask enough questions sometimes going into something. But it's my best quality. Cause I don't overthink. And I'm optimistic in that everything will work out.

[A]

And fearless. It feels like there's a certain part of you that is not scared about what options that you have. You're just gonna go, thank you. I don't know. That's like. When I look at all the things that you do, I mean, I'm interested to understand what lessons you're learning as you kind of like juggling all of these businesses?

[B]

A lot of lessons. More recently, just, I like being nimble more than having, like, I really, really like being hands on. And it gives me anxiety the more I have to delegate. I find that I like to get my hands dirty. Like, I just re edited something myself a couple weeks ago. Cause I was like, I want to show how it should look. And I feel like it'll take me more time to explain it and I can see how it is in my head.

[A]

And you can do that? You can edit black footage?

[B]

Sure, yes, I can. That's where I came from. I had to do it for Awkward Black Girl. And yeah, this was like, basic, but this was just to get the message across. And I'm like, I miss doing that. I miss showing. And it pisses me off that things cost money, extra money when I know I can do it myself and I know I can do it well. And it takes extra time. And I'm just like, I don't ever want to forget where I came from, where I was. Like, I want to make something so I can make it. I can just do it. That is a huge thing that I'm learning this year is like, more people. Doesn't mean it gets done faster. It means it's just more people.

[A]

Yeah, it's just more people. That's all it is. When I feel like there's such a big difference between, like, visibility and power. When for you, did you kind of realize they weren't the same thing?

[B]

There's something about this era, and I was just saying this, like, because we're in this era of social media, you feel like because you have eyes on you, you should, like, I found myself. I want to talk about this thing or show what I'm doing. And I'm like, why? Who care? Who deserves? Why does anybody need to know this? Why does anybody need this? What is this doing for me? Where I find, like, there's just so much power in just quietly doing. And when things are ready, like, I just, I love popping out with something finished that I want people to see as opposed to having these moments of constant accessibility that kind of mean nothing and aren't special. Like, I think for me, what I've. The conclusion that I've come to over the last couple of years is I want to do stuff that feels special.

[A]

Where's that come from?

[B]

From having so much thrown at it. Like, everyone talks about the attention economy and just the barrage of content. And now, like, what slop is gonna be like, I think people are gonna crave. And I know that I myself crave things that feel like they are special and that they're fleeting or that they are conversation starters and that they make me feel a certain way. Like, I'm drawn to things now that just, like, I can't shake. Whereas if you asked me the last video I watched, I can't remember, but I can remember, like, yeah, I was happy in the moment, but it's not staying with me. I crave things that, like, stay with me. Cause I remember how those things, they made me want to be an artist. They made me want to create things that made other people feel the same way.

[A]

Yeah. And so is that, like, a barometer for you? When you're choosing your projects or you're choosing what businesses to go into? You're really looking for something that has, like, staying power, something that is going to be, like, memorable and thoughtful and move you.

[B]

Yeah. I said I want to make my. I want to make people's favorite shit. Like, and that means that can be a range of things.

[A]

You need a T shirt, and it has to go on a wall somewhere.

[B]

I just want to make your favorite shoe. And that can be anything. That could be, like, high art. It could be, you know, slapstick humor. But, like, there's some. I have just, like, I have a range of things that make me so happy and that have defined who I am because they just. There was some intention and there was something that resonated with me at the time and that the period that I was in, or. It means a lot to me and my friends because it's inside jokes. And so, yeah, I look for things that make me either laugh really, really hard because they're funny or stupid or things that just make me feel emotionally seen. And that's kind of my guiding, my guiding light.

[A]

I've always believed that hosting is about more than just having people over. It's about creating space. Space for connection and conversation and for people to feel welcome, whether that's friends, family, or collaborators. I love bringing people together in ways that feel thoughtful and personal. And that's something I really appreciate about Airbnb. When you book a stay, you're not just choosing a place to sleep. You're choosing a home that reflects a neighborhood, a rhythm, and a way of think, thinking. It's what makes the experience feel so personal. And for people who travel often, there's also an opportunity there. While you're away, your home doesn't just have to sit empty. You could Host your home on Airbnb, giving someone else that same sense of comfort and connection while also earning a little extra income that could go towards future travel or a home project you've been thinking about. Hosting doesn't have to be complicated. It's simply about sharing space in a thoughtful way and letting your home work a little bit harder for you when you're not there. Your home might be worth more than you think. Find out how [e-mail] host. I wonder what surprised you most about where, like, the decision making sits. Because you strike me as somebody that is very clear about your intentions. You have a North Star. You want to make people's favorite shit in the entertainment business, sometimes it's not always your decision. I just wonder what surprises you now about where the decision making power actually sits.

[B]

What surprises me?

[A]

Yeah. Or even like, it's not even what just surprises you. It's like, I guess you're someone who's kind of taken that somewhat into your own hands. Was that always part of the plan?

[B]

Ideally, yeah, that was part of the ideal plan. But to your question, something did surprise me where it resonated with me last year where I was like, oh, and I have so much respect for executives and people who give notes, but it dawned on me that what I wanted to make was in the hands of one person. The decision making was in the hands of one person's taste. And I was like, oh, okay. And they might be really honest about that taste. Like, oh, this genre thing might not be for me, but that also means it doesn't get made because it's not for them. And so that, that was like, eye opening for me in a way where it was like, oh, yeah, I'm beholden to a singular person's taste. And while their taste might be broad and I respect their taste, everything's not gonna be for them. Which means, like, I'm. The things that I really, really wanna make on a large scale, I can't make because of that. And so that took me a long realization. It took me a long time to realize. And. And so that also made me double down in another area where I'm like, oh, I want to be able to make things independently and have a breeding ground for experimenting. And I'm excited to do that more this year.

[A]

Do you think there have been moments, or rather have there been moments when there's been an expectation that you would be grateful for access when you are actually the one bringing real value?

[B]

Yeah, that's.

[A]

How did you respond?

[B]

Not well. Honestly. I've heard that said a couple times. And, like, there was an incident that happened where those words were kind of used. And I was like, oh, that's all right. All right. This is a business at the end of the day, and we're not friends here. And I can realize. I'm happy to realize that. And it kind of made me disconnect and also, in a hardened way, like, look at myself as a product. I think that that is taking feelings out of it where you're like, okay, I am creating a product. I need a buyer. And if they're looking at me that way, then there's a way where I need to balance, like. And this actually happened also on the movie side, like, working with studios and making things that a studio will be willing to buy, that has changed so much totally. Like, trying to figure out what is theatrical and molding to kind of their standards. It can be sometimes, like, soul crushing, where you're just like, oh, damn, this is it. But you guys know what you're talking about. You know what you're talking about. Like, there was a. When we produced one of them Days movie that I'm super proud of, that was, like, so much fun to make. I'd never done. I'd never tested a movie before that was like my own, you know? So we would test the movie in front of.

[A]

What does that even consist of? Like, showing it to them.

[B]

Showing, like, people that come to a movie theater, they will show up. We'll sample. Like, have a sample audience. They don't know what they're gonna come to see, and they're gonna.

[A]

They watch the whole movie.

[B]

They watch the whole movie. And we watch them watch it. And we watch when they laugh. We watch when they don't. We watch what they respond to. And then you kind of adjust the edit from there. And so the first time you're showing it, we know that there's flaws in the movie, but we want to test it for the audience to just see where we are. And after that first screening, the executives were like. Or no, the person who does the survey was like, you need something in the first 12 minutes of the movie that's gonna make the audience laugh. Otherwise, they don't know it's a comedy. And I'm like, that's so. Like, that's so reductive of an audience. Like, they're not smart. That's. I don't know. But, okay, let's figure it out. So we had to figure out and conjure this moment that was broad for audiences to Realize, like, this is a comedy. And we worked together to find that and finding the balance of, like, please, God, like, can we make it this? Can we make it this? Can we make this? And then we settled on a moment, and it literally works. Then the test decision, it was the right decision. And I'm like, that's when they know what they're talking about and have learned so much during this process. And that's when I'm like, oh, this is a product that has been tested, that has been sampled. And my creative instincts aren't always gonna be right, no matter how passionately I feel about them. There are formulas that work and that audiences swear by. If I wanna make stuff that isn't that, then that's my own creative risk. Then I'm not making a studio movie and I'm taking that risk on.

[A]

But that's like, you know, a culmination of, I guess, you know, experience and somewhat of, like, you being, like, having a maturity level to be able to, like, take that information. Yeah. I wonder, like, you know. Cause I feel like as women, we're so often encouraged to be collaborative and agreeable. And I wonder if you've ever felt the tension of having to be respected and having to be liked in your business. Of course.

[B]

Yeah, absolutely.

[A]

How do you navigate that?

[B]

Well, generally, I. I still approach things. Cause I've seen the other way. I've seen people just throw their weight around and do all that. And I don't like that. I don't. I don'. I don't like witnessing it. I've seen people I respect and talent I respect, like, talking to people any kind of way. And they maintain that that is how you get things done.

[A]

It's the worst.

[B]

But, yeah, it is the worst. And I feel like what I've done is taken a step back and realized, like, everybody who's a part of something for the most part wants it to be good and wants to do a good job. And so talking to people like they don't want that is, like, everybody loses. And so I try to find. I try to keep that in the back of my mind, like, you wanted this to be good. You want to help this. So, like, how can we work together to make that happen? Unless someone is outwardly disrespectful to me, then I won't return that energy. But make no mistake, if you are disrespectful to me, I will come at you really hard. But, yeah, generally, no, I try to operate with kindness and with the. With the intention to move Forward and make something good.

[A]

What kind of leader do you think you are?

[B]

That I feel like I'm one that listens. I'm one that I like to fix things. I hate things. The biggest challenge I've had is when people come to me with problems that are more to vent. And I'm like, I can't do anything, so I can't do anything about this. You're just telling me this and I still have to carry this now. And like, what can I do about this to fix this? And yeah, I think for me, if it's not a fixable thing, don't tell me.

[A]

You know, I mean, I'm not. I have a low tolerance for people coming to me unless it's a solution.

[B]

I'm like, yes, and help me find a solution.

[A]

Like, I will whine and moan with the best of them, but I need you to start with the solution and then we can bitch them over now.

[B]

But give me the solve.

[A]

Don't waste my time here.

[B]

I completely agree. You know, I have been like, please, if you're going to bring me something, like, bring me two things you want me to. You've been thinking about for a solution because I have to fix a whole bunch of different things in the day.

[A]

And so you've just got this part. How comfortable are you using your power? I'm like, please, come on, just rein it in. How comfortable are you using the power that you've earned compared to earlier in your career?

[B]

I think way more comfortable now. Before, I used to tiptoe a lot and do the. To your point, like, I just want. I don't wanna ruffle any feathers. I want. I just got here. I want people to like me. Now that I'm like a business, I'm just like, yo, business gotta get done. I don't care. And then, honestly, this period is pissing me off a lot. Because to watch people. Because it is like watching people comfortably be like, we don't want to make black shit or something is too black. Or like, we don't want to. We're stepping away from these things and sitting in that and feeling power, power. And like, oh, we don't have to hire. We don't have to do diversity hires. Because that's what I always thought it was the entire time. Like, not having that same mission and be able to just go back to the status quo. Like, that doesn't. It just doesn't sit well with me. Like, what is. Where's the intention? Like, where's the acknowledgement? And I'm not saying that, like, the way that things were was great at all, by any means. I feel like there was still a lot of. I don't know, there were moments of entitlement. There were things like that. But I just feel like not acknowledging that we have a broken system is so stupid.

[A]

So stupid. I want you to say a little bit more about that, because I do feel like, you know, there was this moment and this time and this energy where corporations. It was like a wake up call. And I think being, you know, not from America and being right in the thick of that and being surrounded by what felt like this, like, amazing moment where people that had just not thought about this stuff in the longest time were suddenly being forced to. And they were being suddenly forced to mandate it and measure it and be intentional. And then the mass exodus, like, what are you actually doing in your own business? That's contrary to that.

[B]

Maintaining it. You know, like, we really haven't switched up. And, yeah, the intention is still there. Like, we still have that same passion, fervor to break people into the industry to. Again, it comes down to telling these stories, telling our stories, and the commitment is just even more there. And when I watched Sinners, like, I was so excited.

[A]

Same.

[B]

We were all so excited. I mean, you know, like, it just felt like something so welcome during a time where we were so starving and thirsty. And it was clearly someone's personal art that just you could feel, watching.

[A]

Talk about something that stayed with you.

[B]

Yeah, stayed with me.

[A]

I feel like I've never seen anything like this before in my life.

[B]

Yeah, And I was grateful to have witnessed that, to share in that. And so that was a product of right after. You know, that was right after. I'd imagine, even the way that he was able to negotiate his deal, that it happened in the 2000s, like, 2021, maybe, and that process. And so, like, that's what we get out of something like that. That's the permission we're granted to make something like that. And that excitement. My favorite shit, honestly, deeply. And so, yeah, I. I'm like, we want to be able to create those things at our company, whether it comes from us or not.

[A]

Issa, if there's one thing that you could say to your industry about the rollback of De and I, what would that be?

[B]

I. I guess just be considerate. Like, just look at, like, literally there. So many sets that I've walked on, have literally just been like, it's all white dudes. Like, did y' all even. Are y' all looking at this, like, come on, just be my. Like, interview everybody at the very least. And that's the challenge. Just look around and think about if it replicates what you see in the real world, honestly, which feels so simple.

[A]

But can I just say, in the simplicity, that's the solve. Because I think what people don't want is they don't want things that are cumbersome. They don't want solutions that take longer. But when you talk and when I talk about this, like, it doesn't take many people in a room to be considerate. It just takes that one person to go, can I just check? Everyone here is everyone. And usually when one person speaks up, the rest of the room goes, oh, yeah, shit. Like, we need to rethink this, right? So I actually think that, like, our own personal responsibility here is that. Be that person. Be that one person that says something. Because often it doesn't take much more than that. Now, listen, we know there are spaces and places where one person doing something's not gonna mean anything, but in a myriad of ways, sometimes that's all that's needed. And so I like to encourage people everywhere, in every company, it doesn't matter what you do. Like, be the person who stands up and says, should we just check ourselves right now?

[B]

Yeah. I wholly receive that and agree.

[A]

Let's go. All right, Issa, my favorite part.

[B]

Ooh, ooh. The legs switched up. What am I for?

[A]

I wanna talk about money.

[B]

Oh, yeah. Let's go, let's go.

[A]

I don't. Nobody wants to talk to me about money. And I was so happy because at the start of this interview, you said to me in the green room, you're like, I'm here. And nothing makes me more happy than when someone just comes to play. Someone comes to have a conversation and just like, get it out. I want to start. Because you are a creative person. First of all, how important is money to you at this stage of your career?

[B]

At this stage, it is important to own. You have to have money. Like you just. You do. You have to be able to be able to self finance, to be able to take risks. Like, that is. That's a huge part of, like, what my. What my North Star is. And so if I don't have the means to pay people to get things done, then I will suffocate. And then I'm at the whims of the mercy of other executive studios. Money matters. And I have have put even talk to my business manager this year, like, in thinking about setting the goals that I wanted to set for this year and beyond. He was candid. He was like, everything. Everything that you're making now is for other people. Like, you're fine, but this is. Everything that you're making from this point is for you to invest in other people, for you to invest in projects. Like, you could be fine right now. You could retire, you could be done. So think about that and how you're using your money. And I was like, oh, that kind of put a battery in my back where I was like, oh, I'm cool. Cause I have been used to just, like, watching myself and making sure that I'm financially stable and feeling like, again, these things will go away. And to be able to hear like, no, you're good. Also was like, oh, well, shit, I can do more.

[A]

How did that make you feel? There's nothing about you that was like, oh, good, I'm gonna like a house in the countryside and chill.

[B]

No. But I was like, oh, that's in my future. Cool. Great. And it's again, so dumb that maybe I didn't think that, but I'm so used to, like, hustling and grinding that it was, yeah, it was a wake up call. That there's nothing stopping me beyond wanting to have a successful business and businesses, like, I don't want to be reckless at all.

[A]

Have you had times in your career where you've been reckless? Because obviously you have invested in yourself. Have there been moments where you've taken risks and perhaps you didn't understand, like, or fully understand the costs or what might have happened?

[B]

Yeah, ironically, when I didn't have money, like, I was taking all these risks and going, you know, heavily into debt, like, I felt so crippled and crushed by the money that I owed, you know, and that sucked. But I was like, there's no other way that I'm gonna get this done. And I guess I. The impulsiveness. I didn't plan this out. I didn't know how to budget. I didn't know what things cost. For me, it was like a necessity to make things. And, you know, ultimately they paid off. And that came with the optimism, like, okay, if I spend this now, I know I'll figure out a way to get back. I'm working three, four jobs now in different night shifts. And, like, I will figure this out, but I need to do this at this time.

[A]

How's your relationship with money changed over the years?

[B]

It's changed a lot in that, like, now I feel, like I said, comfortable. I don't think about it as much in my like personal, daily life. I think I only think about it when it comes to investing and advancing my businesses and what's possible. But I honestly, I still am approaching things with the, like, we can get it done for this. Like, we don't need to spend that much money.

[A]

You're frugal.

[B]

I am so frugal. I am so frugal. I don't have all the streaming services. Cause I'm like, why am I paying for stuff if I'm not watching this thing? I don't. People make fun of me for that.

[A]

But I'm like, I'm frugal.

[B]

I'm like, just cause I have it doesn't mean I need to spend it. And if it doesn't make sense. So what I will say is, like, you asked me my reckless things. I was just talking about this last night.

[A]

I wanna know your reckless things. I wanna know, like, the last fun purchase.

[B]

No, it's all. It's literally food and travel. That is it. I will pay so much for a restaurant experience. For Michelin whatever. For someone that's. That's what you love.

[A]

That's a treat to you. Like Michelin star deliciousness.

[B]

I love pet wine pairings. I love alcohol. I love all the samples. And I love going places that like. Like being able to point on a map and being like, I'm gonna go there and I wanna stay in the best resort or the hotel or wherever it is. Like, that is mine. I like it. Yeah, but. Which are things that I can keep, but they stay here. Like, I don't really buy things, unfortunately, that are like, I can point to and be like, oh, I have that. That's what I spent money on.

[A]

No, you're like, I went to Japan and I had these insane experiences and that meant something to me. Yes.

[B]

Yeah, true.

[A]

I mean, that's a great way to spend your money. I mean, for women that are listening to this and they're always told to, you know, like, invest in themselves. What do you think about that conversation? That deserves a little bit more honesty, given your experience.

[B]

I guess. Yeah. Sometimes there's a reticence to take care of themselves. Like, especially if they have families. Like, they're like, I have to make sure everybody else is good, which I respect. But nobody will be good if you're not good, you know, And I think that if anything, that's the message. But I've been. I think I'm working on being a little less selfish this year. Anything. I have been selfish and I've acknowledged that. Like, I'm like, oh, wow. The older I get, you're like, I.

[A]

Could tip the scale the other way I could.

[B]

I could definitely do that.

[A]

Please tell me about that, because that, to me, is so interesting. You know, I've just written a book. It comes out in April. It's called Start with Yourself.

[B]

And I am big on selfishness, but I feel like you can afford to be like, come on. But I guess, you know, this industry will have you feeling like. And you asked me if I feel like a star. No, but I've definitely been catered to. And this industry will make you feel like you're important, and that's not real, you know? And so in that way, like, I've had to shake, like, yeah, this is not about me. There are other people that make this work. Like, you should be thinking about other people a lot more throughout this process and making sure that they're good. And I do, to an extent, but I could do more, you know, and not even to an extent, I do think about other people. But, yeah, there's just more that I could do to decenter myself.

[A]

So what does the season of less selfishness for Issa even? Look.

[B]

It is, like, being more intentional about, like, these were also my resolutions.

[A]

But please give them to us, like.

[B]

More family time, being there for friends. Like, so many of my friends have been there and family members have been there for my events, and, you know, I want to make sure that I'm there for the things that matter to them and carving those time, carving that time out, and, yeah, just being more generous with my time for the people that I care about.

[A]

Is some of this stuff, like, just age and wisdom, or is this coming with a certain thing that's happening?

[B]

It's probably going back to what I feel like is missing, you know, like, the personal side and investing in the personal side and making sure that that balance is there. So, yeah, it's coming with age, but it's also coming with, like, the awareness of. Of what else fulfills me.

[A]

Yeah, I wonder. I wanna go back to all these businesses that you're building, and I wonder how you protect, like, your creative flow and your creating energy when you're doing so many different things in different lanes.

[B]

I trust the people that I work with and that I collaborate with. I make myself available when I'm needed, but if people have a. And then, you know, I'm there for, like, the critiques and trying to improve things. But I. For this year, I have such a target and have such specific goals about what we need as A company, what I need as a creative that I've been really focused on that because like I said earlier, if I don't have the things that I'm creating, also if I'm not visible to a certain extent, then nothing else really works or matters in the same way, like in. And a rising tide lifts all boats kind of way. So I really have to make sure that, like, why, like the core of why I got into this industry is functioning and functioning well.

[A]

And is that how you do it? Like you set goals for yourself and the company?

[B]

Yes. But also the best thing that I ever did was hiring a coo. I really wanted that a long time ago. And a lot of it's a goal. It was. It's been a goal for a long time. I've been looking for a long time. And because I find that, you know, a lot of my day was wrapped in meetings and managing the company and that meant that I didn't have time to.

[A]

Production company specifically.

[B]

Yes, like the company hooray at large. And so to be able to have someone who is actively strategizing and actively keeping us on target and actively holding people accountable in a way that, that I almost felt embarrassed to only because, like, I can't hold you accountable if I'm not holding myself accountable to this deadline and blah, blah, blah. And I have. My attention is split so many ways. So to be able to find that right person to do that has been a huge weight off of my shoulders. I'm still deeply involved in these targets and like I said, I'm super hands on. But yeah, I needed focus and I needed that.

[A]

This episode is sponsored by BetterHelp. February has a way of putting a spotlight on relationships and not just romantic ones. Whether it's partnership, family, work dynamics, or how you're relating to yourself, it can start to feel like everyone else has it all figured out. The reality is that most people are still navigating things in real time. And no matter where you are, are married, dating, single, or focused on personal growth. Therapy can help you find clarity. It's a space to slow down, understand what feels heavy, and take some pressure off yourself. Therapy can help you identify what might be getting in the way of healthier connections and more grounded decisions. Whether you're working through things on your own or with someone else, it's not about having everything solved. It's about creating room to think, reflect, and move forward with intention. BetterHelp makes it easier to get started. Their therapists are fully licensed in the US and work according to a strict code of conduct. They handle the matching through through a short questionnaire. And if your first match doesn't feel right, you can switch it at any time. With over 30,000 therapists and more than 6 million people served worldwide, BetterHelp has an average of 4.9 out of 5 rating for live sessions. Sign up and get 10% off at betterhelp.com aspire that's B-E-T-T-E-R-H-E-L-P.com aspire Lets be honest, finding supplements that are clean, transparent and well made can feel totally overwhelming. Too many brands hide behind fillers, mystery ingredients and taking care of your body just should not feel that complicated. That's why Symbiotica stands out. They're redefining wellness with clean science backed supplements designed for superior absorption. Everything is luposomal, third party tested and made without unnecessary additives. This is wellness done with intention. One of the biggest reasons why, why I love them no pills. Symbiotica supplements come in convenient single serve pouches. You just squeeze and go. They're easy to take everywhere. Whether you're traveling, heading to a workout or moving for a busy day, they actually taste great. Some of their most popular options include lupizomal vitamin D3 plus K2 and CoQ10 and lupizomal vitamin B12 plus B6 now available in portable packets that make daily routine things simple. They also offer magnesium, L threonate, glutathione and vitamin C. For a well rounded approach to daily wellness, Symbiotica is as high quality as it gets. Wellness made simple for you and your loved ones. Go to symbiotica.com aspire to get 20 off plus free shipping. That's C-Y-M-B-I-O-T-I-K-A.com aspire for 20 off plus plus free shipping. What are your goals? What are you ambitious for now?

[B]

I want to be more prolific, you know, even in the things that I make. I do, I do.

[A]

I want to be more prolific.

[B]

Yeah, like there's so much that I want to make. I want to make so many. I want to make more movies, I want to make more TV shows, I want to expand my digital footprint now that I can like there's just. And that's not just me, that's working with collaborators that I've always wanted to work with. And now that I can be available to do that, another resolution was to be less accessible, you know, and that like accessible in the sense that Yeah. I would take these meetings, I would meet with you for lunch, I would go to dinner, and then that would be more time sucks for me, and, like, more time that I'm not doing what I feel like I'm supposed to do. So I have been humbly staying inside.

[A]

How did you learn that discernment? Cause I'm sure after Insecure, right. The floodgates opened. Everybody wants to work with you. What's the conversation that goes on in your head that decides whether you should be involved in something or not, or take an offer or not?

[B]

Oh, man. What's the conversation? Yeah, it's just.

[A]

Cause I just imagine you, like, in a mirror having a conversation. Don't know why.

[B]

I write it down, actually. And I will. I will weigh the. What is it? The opportunity cost. That's like, the one thing I learned in economics is that. And just, like, what.

[A]

That's a big one to learn the opportunity cost. Especially for someone like you, because, you know, for you to be visible in some. Your time is finite. There's only so many hours in a day and days in a year.

[B]

Yeah. But some people do it really, really well, and there are some people who genuinely enjoy it, and I don't. I have to recognize that, like, are you gonna, like, Are you gonna, like, shilling yourself out for this? So it really has to matter. Like, when I love something, I will whore myself out for all day, like, in all aspects. But if I'm, like, only lukewarm, then it does feel embarrassing to me to show up and be like, hey, I'm promoting this. You know? And so I think about that often. Like, how are you gonna feel when it's out?

[A]

Yeah.

[B]

Or when it's. Yeah. When it is, like, you have to post it on your social media. You have to do that collab post. You have to do whatever it is. Like, are you gonn. Are you gonna feel good about it? Are you gonna feel like, ugh?

[A]

And.

[B]

But post Insecure was different. I didn't have the experience. For me, it was just like, my eyes are open. What?

[A]

Yeah, you're not.

[B]

Like, this is a possibility. I can work with this person. Even though I may not be mentally ready yet. Like, I. Yeah, I'm gonna go for it. Okay. I fucked it up. Damn. Like, a lot of that happened. Yeah.

[A]

Like, absolutely no doubt that happened. What are you most excited about now?

[B]

Now I'm just proud of the stuff that I'm making and the collaborators that I have. I'm. This. I keep saying that this year is. It does feel Like I've been saying, like 2016. It's been feeling like 2016 before. Everybody else has been saying it.

[A]

Oh, were you. Were you an early adopter of that?

[B]

I was. I read it last year. I was like, my husband says that.

[A]

I'm like, shut up.

[B]

He said that too?

[A]

Yeah. He's a Pisces.

[B]

Oh, he's a Pisces.

[A]

He's a Pisces. Yeah.

[B]

So he knew. He had the feeling that this year.

[A]

I think he's usually good at, like, catching a vibe. He's like, emma, you know, this is what everyone's gonna be talking about saying. And I'm like, no, not that 2016. Around me.

[B]

It's real. It felt similar in that. Like that year for me, I was on the cusp of creating and felt like I knew that I was making something that I really desperately wanted to be making that I was super excited about. And I have the same energy this year around multiple things where I'm like, oh, this feels like the build it year. And. And it feels like the reaping year. And then the sewing year is next year. Oh, it's like a two year old. It's a combo.

[A]

Yeah. No, no, it's a 1, 2 patch. This I understand. I'm into the 12 patch. Like, I like to brand my years and I always have like an idea for like, this is this year and then this year leads to this next thing. The 12 totally works for me.

[B]

What's your brand for this year?

[A]

Oh, like, this is the breakout year.

[B]

Oh, I love. Okay. Yeah. What was last year? Totally.

[A]

I don't know. I've been sitting behind a desk for the last 10 years. I can't tell. They're the typing years.

[B]

Okay, so that was the clutch. It was the clutch. The class year of years that she's.

[A]

Been like, you know, meant sewing.

[B]

The breakout year.

[A]

It's gone in such a flash that, you know, sometimes, like, you can lose years. That's what kids will do for you. Between the kids and the companies, I'm like, I need to break out. And I don't mean it in that sense of like, you know, a star breaking out. I mean, breaking out. I completely get it. That have sucked and taken every bit of time and energy that I've had.

[B]

I need to like, feel that you've.

[A]

Grown up now, feed yourself. And that company works.

[B]

Okay, bye. Bye. Yeah, I feel it. You're pouring into me. Is this also what the book is about?

[A]

Kind of. I mean, the book is really one of these things That I was desperate to say because I just feel like we're in such an interesting time in the culture and the way people work and so you know, I can't. I'm like in the same way that you said you don't wanna hear people just come to you with like noise. I don't wanna hear that from a whole section of society. So I just thought, I just tell em what I think.

[B]

Woo. Yeah, I'm gonna pick that up. Cause yeah, I need to hear all that. But the breakout year, I feel it.

[A]

We try but I love the one, two punch. I love this idea that you're like sowing the seeds and then you're gonna reap the rewards. I mean this is, it's pretty incredible stuff though. Like it feels like Elaine and you're doing the, you know, great stuff and great work and you look like a person who is somehow kind of quietly confident about what they're doing.

[B]

Yeah, I would say that I am quietly confident. Yeah. Because I just don't want to be seen being confident. You know, it's just.

[A]

Yeah.

[B]

I would rather again be behind the scenes and just working and then emerge like. Yeah, the cocoon thing where I'm like, I feel like I'm very much in this cocoon and like this self made cocoon just like becoming what I want to be. Like becoming this. To your point about the typing cluster years, I feel like the last couple of years I've been a moth and now I'm like oh, I'm about to come out a butterfly. You.

[A]

That's a c. I mean I love that I'm thinking about this idea about you know, like productivity and pressure. Like at what point does all of this productivity that you've got in your life become pressure to you? Is there any sense of uh, I.

[B]

Think when it comes to. I, I put a lot of pressure on myself for sure. But then yeah, when I think about the other people who are depending on me and that could be people at the company that could be, it could be familial. Yeah, I just.

[A]

Oh, you have that too.

[B]

Yeah. Yes I do. To a less extent than you. For sure. For sure. I'm gonna four girl. I don't have four kids. Um, but ye. I think about it is mostly on myself because I envision in my head where I want to be and I'm so impatient, you know, like it really, it really bothers me when things don't happen on my time and like I always learn on the other side like oh, the timing was just Right. But it's a lesson I have to learn literally every single time.

[A]

Really. Because it just doesn't. Like. It's just not dropping in for whatever reason.

[B]

Yeah. I get frustrated when I. When I can't do things the way I want to do them now. When things aren't on my time, like, I think. I guess that goes back to being bossy. It goes to being ambitious. It goes to this overwhelming feeling that I'm running out of time. Like, all these things. Do you feel that? You feel like you're running out of time? Yeah, yeah, yeah.

[A]

What is it about the fault is that does that to you?

[B]

Shit is fucked right now.

[A]

That shit's for real.

[B]

Shit is so fucked. But, yeah, like, you know, I think also in a good way, where it's just, you only have this life if you don't believe in reincarnation, which I would like to believe in it. Heaven's. Never mind. I'm not going to get into that.

[A]

Don't. Go on, Go on. I love that.

[B]

Well, just heaven sounds so scary. Hell sounds scary. But, like, living in a place, it's. I'm getting too much. But, yes, I want.

[A]

I was so into. I was like, we're going to be scared of heaven.

[B]

There's.

[A]

Well, you feel like you bored. You're going to be bored in heaven.

[B]

I hope not.

[A]

It's not enough.

[B]

Do you know what? It's infinity. It's like the infinite. Like, when I think about things going on forever, whenever I think about, like, time goes on forever, I would rather be doing different versions of that time as something else as opposed to whatever this is.

[A]

Well, you're like a person who's, like, craving the transition.

[B]

Like, craving, like, the what's next.

[A]

Like, something's great and you're, like, not resting on your laurels. You're already moving on. Like, you're trying to cook the next thing.

[B]

Yeah, kind of. Yeah. No. Yes, that. But, like, where life is concerned, I absolutely have to make the most of it right now.

[A]

Yeah. And also, I feel like there's a certain amount of privilege in this situation that you've created for yourself, that you're like, why wouldn't you make the most of it?

[B]

Yeah, if I can. There is so much, like, anytime I'm. By no means. I feel restless right now and I feel weird and I've been expressing that, but I am beyond happy. Like, I feel happy that I've been able to build a life that I want. You know, there's. And my happiness does come from, like. Yeah, Creating things, whether that is creating the life that I want, whether that's creating your favorite shit, whether that's maybe creating a family, maybe that's whatever. Like, I feel fulfilled when I'm productive and doing things and. And those things fulfill me. And waking up every morning and feeling like I have a go at it and a go at something new really, really excites me. I love that.

[A]

How do you think about legacy? Do you think about legacy?

[B]

Yes. Yes. Because I think about death all the time, clearly.

[A]

Do you?

[B]

Yeah.

[A]

Because of the heaven thing was just the question I asked you.

[B]

Thinking about. I watch it all the time.

[A]

You do?

[B]

That's like, when you love your life, you're gonna think about death, you know, you. And. And what's. What is next. And so I think, yeah, I know that part of the running out of time thing for sure, is, like, wrapped up in mortality for. You know, but it's also thinking about Windows and the like. So, yeah, I think about.

[A]

It's amazing to me that you say you think about death like one of my. I'm gonna totally mess the quote up, but, you know, that Steve Jobs quote, it was like a. I think it was like a Stanford commencement speech where he said, the single best invention of life is death.

[B]

Oh, man.

[A]

And it just is like, you know, the knowing. Waking up every day and knowing that your time is finite and one day you'll be gone is the best thing.

[B]

It's a great motivator. It honestly is. And it's so funny. I think about his last words a lot. Like when he was dying of cancer in the hospital bed, he, like, lost consciousness for a bit. And as he was dying, he said, oh, wow. And I think about that. I was like, what did he see? What did he see? And then he just, you know, he left.

[A]

Oh, wow.

[B]

Yeah, that's what he said.

[A]

That's just crazy. What did he say now? I want to know. What did he say?

[B]

What did he see? What we want? No one told us.

[A]

What a life.

[B]

Yes. Oh, wow. Yeah.

[A]

Look at that shit that I did.

[B]

He could have been flashing back to what he did, or he could have just seen what's next.

[A]

Yeah, he was, like, doing an Easter. He's like, I made your favorite shit. Oh, wow.

[B]

This is it. Yeah.

[A]

Yeah. Unbelievable.

[B]

I'd like to think that.

[A]

Unbelievable. So your legacy will look like, what? If you can fast forward and look back and say something about your career, what would it be?

[B]

I don't get to dictate that, but if I could, I like what you said about being fearless, like, but I. When I compare myself to people who are actually fearless in the face of danger, it doesn't add up. So I take that back.

[A]

No fair.

[B]

I take it back. I take it back.

[A]

I understand that. I mean, in your industry and what you're doing, because, Issa, there's a part of you that's like, as I was doing my research, I was like, she's a one of one. There's not 10 issas. There are. You're very, very formative in forging a path and doing things in a way that isn't easily replicated or seen. And so I do think that there is a part of you where that fearlessness, like, has to be. Like, it has to be there. Like, as I was going through, I was like, wow, she's not scared of anything.

[B]

She's just going, that's so interesting.

[A]

Isn't it interesting what other people think about you?

[B]

Yeah, it is. And I really, really try not to think about it, but I thank you for that. No, I want to be remembered more as a person than for my work. You know, I want my work to be. To stand on its own. But, like, the good things that people say about you are, like, the interactions. Like, that still matters to me, too. Like, I want to feel like. And that is part of my personal work. Like, I want to be more considerate. I want to be less selfish. I want those things. And I do feel like there's a chapter of my life that I'm gonna enter outside of this that feels more purposeful in a different way once I figure out what's missing. There's nothing worse than, like, loving something, loving a work, and then kind of hating the person behind that, or not appreciating the person's behind that. Like, I hate hearing that some of my faves are monsters, you know?

[A]

It's the worst. There's nothing worse than meeting your heroes and being disappointed by them.

[B]

Yeah, I try not to meet a lot of them.

[A]

Yeah. I just don't meet him.

[B]

Yeah, Just.

[A]

That's what I learned. Just don't meet him. Just keep it in your imagination.

[B]

Yeah, everyone's great in my imagination.

[A]

I'm absolutely right. You know how rent is one of those things that most people pay every month and don't really think twice about. It's just part of life. But BILT is built around the idea that if you're paying rent anyway, you should actually get something back from it. BILT is the loyalty program for renters that rewards rent payments with points you can redeem towards things like flights, hotels, Lyft rides, Amazon.com purchases, fitness classes, and so much more. BILT members can earn points on mortgage payments for the first time. So whether you're renting now or thinking ahead to what's next, you can be rewarded wherever you live. BILT also unlocks exclusive benefits with more than 45,000 neighborhood partners. From restaurants to fitness studios, videos to everyday essentials, it's designed to fit into real life, not change it, and to make a monthly expense feel a little more intentional. If rent is part of your reality, BILT gives you a smarter way to engage with it. Join the loyalty program for renters at joinbilt.com emma that's J-O-I-N-B-I-L-T.com emma make sure to use our URL so they know we sent Starting a business gets complicated fast, and that's something I hear all the time from founders. One minute you're focused on the idea, the next you're juggling conversations. Follow ups and try to remember where every deal actually stands. Things start living in different inboxes, different notes, different spreadsheets, and suddenly there's no clear picture of what's moving forward. That's why I've been recommending pipedrive, my favorite sales CRM for small and medium. Because businesses pipedrive is designed to bring clarity to the chaos. It gives teams a simple visual sales pipeline so you can see every deal at a glance and customize each stage to match how your business works. It's easy to set up, intuitive to use, and helps keep everyone aligned without adding unnecessary complexity. It also connects with over 500 apps so it fits into the tools the business is already using. And it's built to scale as teams grow and processes. A new year calls for a new CRM. If you're starting a business or working in sales, I would highly recommend checking it out. Over 100,000 companies are already using Pipedrive to grow their businesses right now. If you go to pipedrive.com aspire you'll get a 30 day free trial. No credit card or payment needed. Where do you think your biggest challenges are going to come from?

[B]

H Besides like myself?

[A]

Oh, it's you.

[B]

It's all you. I'm always you. Be the problem. Like I will own that I am the problem. I think also my biggest challenges are not knowing. I was just talking about this like letting things, giving people multiple chances and.

[A]

Not you're not good at that.

[B]

I am giving. I'm too good at giving People. Most. You're too good at giving people. Like, I will see the best in people. And I've had to.

[A]

You are a lovely girl.

[B]

I'm stupid, like, in that way for sure. And I've had to be like, no girl. Nip it in the back. It's not working.

[A]

Yeah, got it.

[B]

Doesn't make sense. I am great with that in my personal life, easy.

[A]

But in business, not so bad.

[B]

But in business. Yeah. Cause I'm like, I'm.

[A]

That's interesting.

[B]

Yeah.

[A]

Oh. So I. Most women I meet are almost like the other way around. Like.

[B]

Ah.

[A]

So it's the business where you're. You're giving people are maybe too much.

[B]

Leeway, especially when they have passion.

[A]

I'm just like, I guess there's a creative component for sure of that. Yeah. I'll fire an annoying creative much slower than I will like a really annoying person who works in corporate in my office.

[B]

Interesting.

[A]

Because there's a value to the creativity that's somehow harder to replace.

[B]

Yeah, for sure. Yeah, I, I completely agree with that.

[A]

Give me an example. Like, when has there been a time when you've just like, not, you know, just haven't cut it off quickly enough.

[B]

Without being with the person seeing this and they're like, that's me. There have been.

[A]

What color hair did she have?

[B]

There's been. And this applies to a few people where, like you, you try to craft a role for them because they are so talented, but that can be expensive or, you know, they may not show up in the way that you. You need them to. Where deadlines are concerned, I need go getters. And when I'm like, one of the things that I've also learned within the business is that we have a lot of. In my company, we have people who come up with brilliant ideas who are the smartest. But I need execut. If you're not. I don't give a fuck about your idea if you're not the person to get it done. You know, facts like, we can talk about how great this idea is all day, but I need executors. I'm an executor, but I can only execute so much. So I need you to be the ideator and the executor along with me and do it well. And so that is the thing. And that's like my biggest pet peeve is someone coming with. Coming at me with a, we should be doing this, we should do, do this, do this. And I'm like, oh, that's great. Do you mean. I Should be doing that then. Cause then how are we gonna get it done? Cause I'm already doing this, this, and this. So, like, help me.

[A]

I feel like that's a great lesson, though, for any business owner, founder, because I call it having an enterprise mentality. Because to me, you have to put the business first. In the times when I have taken a person that I have a certain affinity for and tried to mold something for them, it's never worked out for the company. And so to me, having an enterprise mentality means you might be amazing, but what I need for this company right now is something else. So you gotta go and take your amazing somewhere else. And that will be better for you too, eventually, even though you don't know now. And I might be the first person to tell you, but that doesn't matter. And so I think learning to have an enterprise mentality, what is best for the business is the decision that you have to make as the owner of the business. And then everything else has to figure it.

[B]

I needed to hear that. I needed to hear that. And there's also. I'm a loyal person too, and also trying to separate loyalty from, I guess what you're. The enterprise mentality. Because it's just like. Just because someone has been with you for a long time doesn't mean they need to come with you for every chapter. Maybe they've served their purpose.

[A]

Yes.

[B]

That sometimes doesn't feel right to me. But I have to, like, business is business, and I have to have a business mindset.

[A]

Yeah, it's very, very, very difficult. And I feel like as somebody that's grown companies, you know, I always talk about it's the people that you started with. They're not always the ones that take you to where you necessarily want to go. The framework that always really helped me is that I always think when somebody's sitting in a seat that perhaps they shouldn't be. I don't think about that person. I think about the person that should be in the seat. I'm like, get out of the seat. No, but you know, in a minute. It's like you're actually stopping the person that needs that right. From having that row. You see how I do this?

[B]

I love it. You're just burning a hole in the chair. Yeah.

[A]

Literally with my eyes and every part of me. No, but I think that it's a really.

[B]

It's so true, though.

[A]

Listen, it's like. Cause you need other things. And usually my experience is it actually benefits that person as well. Because people know when their time is up. They know when they've come to the end of the road. It's so hard for them to say. It's so hard for you to say. But you check in with that person, six months later, they're like, oh, my God, I'm killing it over here.

[B]

Yeah. And you have to go back.

[A]

And now I'm in. And now I'm, like, wanted. And, like, everyone was feeling it.

[B]

That was me as an employee. I gotta say, I've discovered. I realized that a few years ago, I was like, I was such a bad employee because I wasn't in the right place.

[A]

Yes.

[B]

I needed to be somewhere else and I needed that. Like, I've never been fired. I've never been fired. I've never been fired, But I should have it. I should have been.

[A]

You should have been.

[B]

I should have been. There were a few jobs where I clearly. One job, I tried to, like, come in and give it my all. And as soon as they shut down my ideas, I was like, y' all don't deserve me. And I did the quiet quitting thing and did the bare minimum. I should have been fired.

[A]

Yeah.

[B]

But, like, I needed to be out of certain jobs to be who I am and where I am today.

[A]

Fair. What do you hope that other women that are forging a path in your. In your image or, you know, are trying to have the type of career that you've had, what do you hope they will learn from your journey?

[B]

I mean, I trust myself a lot. And now I didn't enough early on, like, those. Those times when I forgot why I was here, why I was in the room. When I second guessed it, I wasted a lot of time. And, yeah, I had to go through those things to ultimately gain the confidence to feel like I belonged in these rooms. But, like, I spent so much time second guessing that that, like, I would encourage other women to just always remember. Like, always remember why you belong in certain spaces, what your strengths are. So in the same way that Larry told me, like, protect what this story is. Protect this. Like, always remember, like, I am fucking good at this. No one can ever take this away from me. These are my strong suits. I always have this. And no matter what, like, I can rest confidently knowing, like, I am good at this core thing, these core things things, and then I'll be okay. Then I can. Then I'm like, all the other things will bounce off of me. Like, all the other doubts that people. I may feel people have about me don't matter because I know this deep within myself that this is what I'm great at. And I feel like I have that where I'm like, I know what I'm really, really good at. And I think my strengths are also recognizing what I'm not good at and asking for. So I guess, yeah, for women, knowing what you're good at. And also don't be afraid to like ask about what you don't know.

[A]

What do you still aspire to do or become?

[B]

I always say better and I don't know what that means in the moment, but I can look like at this year and be like, I'm better than I was last year. I know that I've never regressed.

[A]

She doesn't go backwards.

[B]

Know aspire to become the second phase of my life. I'm still figuring out. I aspire to figure that out.

[A]

That's pretty amazing. I love it. That's just. I love it. You're honest.

[B]

I am.

[A]

You really are. So before we wrap, a quick reminder that Start with Yourself is available for pre order and tickets for the live shows are available now. Starting April 15th, we're coming to New York, Los Angeles, San Francisco, Chicago, D.C. boston, Atlanta and London. Visit emmigree.com for tickets and full tour details. I cannot wait, babe. I only have some rapid fire questions for you and I'm gonna get you out right on time. All right, first rapid fire, which is impossible for me. Cause I'm so long winded. Okay. What is your comfort? Classic TV show.

[B]

Can I just. This is a classic. It's any dating reality show. Like I will wear watch.

[A]

I stopped loving reality.

[B]

That's what I love.

[A]

Island. Like what?

[B]

I loved Love Island.

[A]

The English one or the American one? Which one?

[B]

I actually started with the American one.

[A]

You did?

[B]

Yeah. I've never seen the English one. Oh, I think I only see one. I know, I've heard, but I didn't have because I don't have all the streaming services. I didn't have because you got off.

[A]

All your apps cuz you're so cheap.

[B]

But now that I got them, I got gifted one of the things. So I'm going to watch uk.

[A]

I mean, I've never seen it.

[B]

I. You've never actually seen it over here?

[A]

No, I've never seen.

[B]

I think that's the best one.

[A]

Well, that's what I heard. Okay.

[B]

So that I used to watch Love Islam. I love the Ultimatum. I can't wait for it to come back. There's a.

[A]

You like trash.

[B]

You're looking trash. But it has to be. I like watching people be Attracted to each other. Oh, and, like, falling in love. And so, like those shows. Give me that.

[A]

All right. What song best captures this chapter of your life?

[B]

This is gonna piss me off. Cause I have one, and there's too many, I guess I'll say. Elmin has a song called Reclusive, and he's my favorite. And it's. That's how I feel right now. I feel like I'm in a kind of reclusive state so that I can do what I need to do.

[A]

What are you still learning to say no to?

[B]

I'm still. Despite trying to be less accessible, still learning to say no to that classic. Hey, can we meet up for coffee? Or can I pick your brain? I'm getting better, but I'm gonna say no. So if you ask me and I don't respond, that's why I don't want to. I don't want to do it. I can't.

[A]

What is a genre you're curious about exploring that people might feel surprised by?

[B]

I like literal genre. Sci fi. I like it a lot, but I like grounded sci fi.

[A]

What's grounded sci fi?

[B]

It's not. I'm not doing, like, aliens, and I don't like fantasy.

[A]

Okay.

[B]

But I like dystopian. Oh, I like dystopian dramas and drama Ds. Okay.

[A]

We are. We're ready for that. I feel. What's a book that changed your life?

[B]

The Courage to be disliked.

[A]

It's a great one. Okay, final. Final question. What is something that you aspired for or to when you were starting out, that you no longer aspire?

[B]

Going to industry parties. I don't. I don't need to be there. She's not that I'm not going. Also, you know what? I've. In my reclusive state. I'm not watching as many things. You see, I just told you what I watch. Like, I watch a lot of trash TV with the occasional show that everybody's talking about that I'm excited about. But when I go to these events and I don't know people, I feel so embarrassed. I feel so deeply embarrassed that I do not recognize you from your show or movie. Cause I'm not up on it. So I would rather stay at home.

[A]

Even though everyone knows who you are.

[B]

I don't want that. That's worse. If someone knows you and is, like, also complimenting you and you can't give it compliment.

[A]

That is very interesting.

[B]

It happened to me, actually, just recently. I was doing a music video for an artist that I'm a fan of and I hadn't seen this show that everybody was working. Cause I just, I was working and I hadn't gotten to it yet and I met a girl and I was like, oh, are you in the band? And she was like, oh yeah, kinda. And then I walked out and my hair and makeup was like, you know who that was, right? And I was like, oh no. Oh no. So that would be my stay home everyday.

[A]

She said, so you said what? I said stay home.

[B]

You stay home. I will stay home. Thank you. You've given me the permission. I will remain at home.

[A]

Thank you. You're just wonderful. You are the least disappointing person. Oh my God. You wanted to meet.

[B]

Thank you. I received that. I am honored. Thank you. But thank you for the amazing question.

[A]

Wonderful.

[B]

You made me really think in that. It hurts a little but thank you.

[A]

I'm happy to hurt you. You're still a one of one in my mind. Thank you. If you're loving this podcast, be sure to click follow on your favorite listening platform. While you're there, give us a review and a five star rating and share an episode you loved with a friend. We'll be so grateful. Aspire with Emma Greed is presented by Audacy. I'm your host, Emma Greed. Our executive producers are Derrick Brown and me. Our executive producers from Audacy are Maddie Sprung Kaiser, Leah Reese, Dennis, Asha Salouja, Lauren Legrasso and Jenna Weiss Berman. Stephen Key is our senior producer. Sound design and engineering by Bill Schultz. Angela Peluso is our booker. Original music by Charles Black. Video production by Evan Cox, Kirk Courtney, Andrew Steele, Carlos Delgado and Arnie Agassi. Social media by Olivia Homan. Special thanks to Brittany Smith, Sydney Ford. My teams at the lead company and wme. Maura Curran, Josephina Francis, Hilary Schuff, Eric Donnelly, Kate Hutchinson, Rose, Tim Meekol, Sean Cherry and Lauren Vieira. If you have questions for me, you can DM me at Aspire with Emma Greed. Greed is spelled G R E D E. That's Aspire A S P I R E with Emma Greed. Or you can can submit a question to me on my website emagreed me.