Mark: Alright Michelle, I'm going to say the title of a book, and I want your honest, one-sentence roast of what you think it's about. Ready? Do Cool Sht*. Michelle: Oh, easy. That's the official handbook for people who use 'disrupt' as a verb in every meeting and probably own a standing desk they never stand at. Mark: That's... surprisingly close. But today we're diving into the real deal: Do Cool Sht: Quit Your Day Job, Start Your Own Business, and Live the Life You Were Meant to Live* by Miki Agrawal. Michelle: Ah, Miki Agrawal. She's a fascinating and, let's be honest, a pretty controversial figure in the world of social entrepreneurship. She's the founder of companies like THINX, the period-proof underwear, and TUSHY, the bidet company. She really made a name for herself by tackling taboos head-on. Mark: Exactly. And this book, published back in the mid-2010s, is her origin story. It's less a formal business plan and more a high-energy, personal manifesto that really captured that millennial zeitgeist of wanting work to have more meaning. It received mixed reviews—some people found it incredibly inspiring, others found it a bit thin on substance. Michelle: Which makes it the perfect book for us to dig into. It’s not just about the advice itself, but about the person giving it and the cultural moment it represents. Mark: And the book starts not with a business idea, but with a moment that completely redefined her life. It’s an incredibly intense place to begin.

Michelle: I was struck by that. Most business books open with a market opportunity or a clever insight. This one opens with a near-death experience. Mark: It really does. Agrawal was working as an investment banker at Deutsche Bank in New York City, right across from the World Trade Center. On the morning of September 11, 2001, she had a breakfast meeting scheduled with a friend inside the Twin Towers. But she overslept, a rare occurrence for her, and missed the meeting. She woke up to the news and watched the tragedy unfold from a distance, knowing she was supposed to have been there. Michelle: Wow. That's an incredibly intense origin story for any book, let alone one with this kind of title. It immediately changes the context of "doing cool shit" from something frivolous to something deeply urgent. Mark: Precisely. She writes about this profound epiphany she had in the weeks that followed. She realized how many people lost their lives that day, unable to fulfill their dreams. She felt that fortune had given her a second chance, and she couldn't squander it in a high-paying job that she didn't love. That was the moment her definition of success began to shift away from financial freedom and toward what she calls "living to your full potential." Michelle: That makes so much sense. It’s a powerful motivator, but I think a lot of people have those kinds of epiphanies—maybe not as dramatic, but moments where they realize they're on the wrong path. The hard part is acting on it. What does she say is the first actual step after you decide to change everything? Mark: Her first principle is to "Stray from the Group." She believes that conforming to the norm limits your experiences. She tells a great story from when she was studying abroad in London. She got a prestigious internship at a PR firm, but it was miserable. She was doing menial tasks for bitchy bosses, learning nothing. The conventional wisdom is to stick it out, that it "looks good on a resume." Michelle: Right, you suffer through it for the credential. That’s what we’re all taught. Mark: But she didn't. She quit. She walked out, risking being sent home from the entire study abroad program. It was a huge gamble. But because she took that risk, the head of the program saw her determination and offered her a different, unconventional internship: working directly for a Lord, creating a visual arts project for the British curriculum. She had total autonomy and a meaningful project. Michelle: Okay, but that London story worked out perfectly for her. She quit a bad situation and was immediately handed a dream one. That feels a bit like survivorship bias, doesn't it? What about the people who stray from the group and just... get lost? What's the safety net? Mark: That's the thing—she argues there often isn't one, and that's part of the point. The book isn't about safety nets. It's about developing the muscle to handle uncertainty. She introduces this concept she calls "MB," for Mutually Beneficial. She says every relationship, every job, every interaction has to be MB. The PR firm was only beneficial for the firm, not for her. So she left. Her philosophy is that by eliminating what's not mutually beneficial, you create space for opportunities that are. Michelle: I like that framing. It’s less about just quitting and more about actively curating your life. She has that system, the BET system—Bullet, Eliminate, Take On. It's like Marie Kondo for your social and professional life. You make a list of people and situations that drain you and a list of those that inspire you. Then you systematically eliminate the draining ones to make room for the inspiring ones. Mark: It sounds simple, but it's incredibly hard to do in practice. It requires confronting people and situations. But she argues it's the only way to build a life and a career that truly fuels you, instead of one that you constantly need to recover from.

Michelle: That idea of actively curating your life is a great bridge to her actual business tactics, because they are nothing if not curated and... unique. Mark: That's a very diplomatic way of putting it. Her methods for getting ahead are definitely unconventional. This is where the book moves from the "why" to the very messy "how." Michelle: Let's talk about the "stalker smile." I read that section and my first thought was, is this a business book or a training manual for a private investigator? Mark: (laughs) It’s one of her most famous stories. She was at an exclusive entrepreneur event on a cruise ship and was desperate to meet Tony Hsieh, the late CEO of Zappos. But she was too intimidated to just go up and talk to him. So instead, she stood across the bar, waited for him to look her way, and when he did, she just gave him this huge, intense, unwavering smile and a wave. And that was it. Michelle: Hold on. The 'stalker smile'? Are we sure this is business advice and not a restraining order waiting to happen? Let's break this down. What was she actually doing there? It sounds a little unhinged. Mark: On the surface, yes. But the magic wasn't in the smile itself. It was the follow-up. After the cruise, she emailed him, referencing their "meeting" at the bar. Because the interaction was so weird and memorable, he actually remembered her. In the email, she pitched her business ideas—her farm-to-table pizza place and her idea for THINX—with such infectious, genuine excitement. Michelle: Ah, so the smile was just the hook. The real product was the passion in the follow-up. Mark: Exactly. Her point is that genuine excitement is magnetic. People, especially investors like Tony Hsieh, are pitched ideas all day long. What they're really investing in is the person and their unwavering belief. The smile was just a bizarre, creative way to get his attention so she could show him her passion. And it worked. He ended up flying to New York, visiting her pizza restaurant, and partnering with her to open a location in his Downtown Las Vegas project. Michelle: I see. So the 'how' is less about a specific tactic and more about finding an authentic, if weird, way to project your passion. It reminds me of her fundraising strategy. She hated the stuffy, one-on-one investor meetings where she felt she couldn't be herself. So what did she do? Mark: She threw dinner parties! She decided to create an environment where she could shine. She invited potential investors to these fun, high-energy parties, served them her amazing pizza, and had a friend present the business plan in an engaging way. She even got the Food Network to film it for a show. She raised her entire seed round of $250,000 that way. Michelle: That’s brilliant, because she changed the game to suit her strengths. She knew she was charismatic and her product was great, so she created a stage for both. But the book isn't all just clever wins. She's also incredibly candid about her failures. Mark: Oh, completely. The "Disaster Launch" chapter is a masterclass in what not to do. After all that creative fundraising and getting a ton of press in a popular newsletter, she opened her pizza shop. But she ignored advice to do a "soft opening." The press hit, a line of fifty people formed on day one, and the kitchen completely imploded. Michelle: It sounds like a nightmare. Wrong orders, cold food, hour-long waits. Mark: A total catastrophe. She says customers were furious, and she was hemorrhaging goodwill. But what's interesting is her recovery plan. She didn't hide. She and her team worked around the clock to fix the operational issues. Then, she personally wrote thousands of handwritten notes to every apartment in the neighborhood, apologizing for the rocky start and including a menu. Michelle: A handwritten note? In New York City? That’s bold. Mark: And it worked. She says 95% of their delivery sales in the first week came from those notes. People were willing to give them a second chance because she was honest, she took responsibility, and she made a personal effort to win them back. It’s a powerful lesson in humility.

Michelle: So when you put it all together, the book isn't really a step-by-step guide like you'd get in business school. It's more of a permission slip. It’s permission to define success for yourself, and permission to be a little weird and scrappy in how you get there. Mark: Exactly. And that's why it resonated so deeply with a certain audience, but also why it's polarizing and has those mixed reviews. The book's core message is a quote she attributes to Steve Jobs: "Everything around you that you call life was made up by people that were no smarter than you." She believes you can poke life, you can change it, you can mold it. Michelle: And that philosophy really informs her entire career, for better or for worse. When you look at the controversies that came later, particularly the allegations about the work environment at THINX, you can see that same "poke life" attitude at play. It’s a mindset that’s incredibly powerful for disruption, but it can also be a double-edged sword if it lacks self-awareness or empathy for the people you work with. Mark: That is the crucial insight. This book is a snapshot of the beginning of her journey, full of raw energy and a belief that she could change the rules. Her career since then has been a real-world test of that very idea—poking life, sometimes to great success, and sometimes getting poked back hard. It shows that "doing cool shit" is a lot more complex than just having a great idea and a lot of passion. Michelle: It really makes you think. What's one small 'rule' in your own life or career that you've been following without questioning? Maybe the takeaway isn't to quit your job tomorrow and start a pizza place. Maybe it's just to stray from the group on one small decision and see what happens. Mark: That's the perfect takeaway. The book constantly asks, "What sucks in your world?" and "What doesn't exist that should?" So a great question for all of us to reflect on is this: What's one thing that sucks in your world that you could try to solve in a small, creative way? We'd love to hear your thoughts. Mark: This is Aibrary, signing off.