Young and Profiting (YAP) with Hala Taha
Rachel Hollis: Reinvent Yourself After Failure and Build a Business That Lasts | Entrepreneurship | E350
Mon, 12 May 2025
Rachel Hollis's career wasn’t an overnight success. After writing five books and experimenting with various business ideas, it wasn’t until a raw post about her stretch marks went viral that her career in personal development took off. Her sixth book, Girl, Wash Your Face, became an instant hit, transforming her into a bestselling author, renowned podcaster, and a source of inspiration for both women and entrepreneurs. In this episode, Rachel shares insights from her latest book, What If You Are the Answer?, exploring transformative questions that turn setbacks into opportunities and the mindset shifts that helped her build a thriving business. In this episode, Hala and Rachel will discuss: (00:00) Introduction (01:18) The Power of Routines and Habits (05:17) Growing a Career Through Consistency (13:50) How One Post Sparked Social Media Success (24:10) Overcoming Setbacks in Business and Life (28:37) Navigating the Ups and Downs of Entrepreneurship (39:47) Mastering Better Business Decision-Making (47:38) Why Entrepreneurs Must Learn to Let Go (52:57) Reevaluating Limitations to Achieve Your Goals (56:57) Raising Your Floor: The Key to Lasting Success (01:02:30) How to Handle Wins and Losses in Business (01:08:50) Identifying Your Sources of Business Growth Rachel Hollis is a bestselling author, motivational speaker, and entrepreneur known for her work in personal development. Her books, including Girl, Wash Your Face and her latest, What If You Are the Answer, have sold over 7 million copies. Named one of Inc. Magazine's “Top 30 Entrepreneurs Under 30,” Rachel is also the host of The Rachel Hollis Podcast, where she explores topics like entrepreneurship, health, lifestyle, and motivation. Sponsored By: Indeed - Get a $75 sponsored job credit at indeed.com/profiting Shopify - Sign up for a one-dollar-per-month trial period at youngandprofiting.co/shopify Microsoft Teams - Stop paying for tools. Get everything you need, for free at aka.ms/profiting Mercury - Streamline your banking and finances in one place. Learn more at mercury.com/profiting OpenPhone: Streamline and scale your customer communications with OpenPhone. Get 20% off your first 6 months at openphone.com/profiting Mercury - Streamline your banking and finances in one place. Learn more at mercury.com/profiting Airbnb - Find yourself a co-host at airbnb.com/host Resources Mentioned: Rachel’s Podcast, The Rachel Hollis Podcast: bit.ly/TRH_Pod Rachel’s Book, Girl, Wash Your Face: bit.ly/Wash-Your-Face Rachel’s Book, What If You Are the Answer: bit.ly/WhatIfAnswer The Dip by Seth Godin: bit.ly/The_Dip Active Deals - youngandprofiting.com/deals Key YAP Links Reviews - ratethispodcast.com/yap Youtube - youtube.com/c/YoungandProfiting LinkedIn - linkedin.com/in/htaha/ Instagram - instagram.com/yapwithhala/ Social + Podcast Services: yapmedia.com Transcripts - youngandprofiting.com/episodes-new Entrepreneurship, Entrepreneurship Podcast, Business, Business Podcast, Self Improvement, Self-Improvement, Personal Development, Starting a Business, Strategy, Investing, Sales, Selling, Psychology, Productivity, Entrepreneurs, AI, Artificial Intelligence, Technology, Marketing, Negotiation, Money, Finance, Side Hustle, Mental Health, Career, Leadership, Mindset, Health, Growth Mindset, Side Hustle, Startup, Passive income, Online business, Solopreneur, Founder, Networking.
Chapter 1: Who is Rachel Hollis and what is her entrepreneurial background?
Oh my gosh, this is like asking what is my favorite child. I think honestly the biggest shift that happened for me about 15 years ago was understanding what a morning routine was and the value of creating one around not just what I wanted to achieve, but the season of life that I am in. I think there's so much content out there telling you how to build a morning routine.
And it's really easy to start to gather information and not really take that on board in what will work for you. So if you are a new parent with a new baby at home, your life and your ability to wake up in the morning is going to look very different than if you are a freelancer in your 20s.
So for me, really understanding the importance of that time, like I have four kids, so waking up before my kids wake up, I know it sounds so simple, but if you start your day on offense versus on defense, it makes all the difference. So waking up before anyone else in the house, having my coffee, I sit in the same spot every single day. I read nonfiction. I do a gratitude practice.
I do those things that are really paramount to what I am trying to accomplish in my life right now. But that's not something I understood I needed a long time ago. So I know that's kind of like a bigger scope, but building that morning routine around your life and your goals is the key.
Chapter 2: How did Rachel develop her morning routines and habits?
That makes sense because every season of life is different and requires different things. Now, what if somebody feels like they're just not a morning person? This is me, right? I struggle waking up early. I get really creative late at night. It's just my natural rhythm to want to stay up late and not necessarily wake up super early. So what would you say to somebody like me?
Well, I would say if you don't have anything that requires you to be up early, then you should go with whatever your natural rhythms are. So if I didn't have four kids, I'm not sure what my normal rhythm would be, but I have to make sure everybody gets up and gets out the door to school.
And then there are other people listening who might have a nine to five job that they have to start a commute for. But if you don't have to, like I have a ton of friends who are entrepreneurs and they might not wake up until 11 a.m., 12 o'clock because they don't have to. And they can stay up all night and really lean into when they feel most creative.
That's why I was saying having a routine that works for you. Take a bunch of the information and do the research. Find out what works for other people. But at the end of the day, it needs to be applicable to your life or it's not going to get you the results that you want. Now, I will just...
caveat or add a little bit here, for someone who does need to be up early and they really want to have a morning routine, they want to be a morning person, but they don't feel like they are, that's a learned skill. Nobody comes into this world, nobody gives birth to a baby and the doctor looks at the baby and they're like, oh, it's an early riser. That's not a thing.
So if you want anything in life, if you want a habit that you don't currently have, you can teach yourself that habit. So if I were you, and let's say you get up every day at seven and you want to get to a place where you're part of the 5 a.m. club. Set that alarm 15 minutes earlier every single day. Let your body adjust to getting up earlier.
Make sure that you have something exciting to wake up for. Like I love coffee. So it's really easy for me to pop out of bed. Or if I have a new book that I'm reading, because I'm super nerdy, but if I have a new book that I'm reading that I feel like I'm learning a ton from, that'll get me out of bed.
Have something that you're headed right into so that you've got a reason to meet your alarm where it meets you instead of hitting the snooze.
I love that advice, just setting the clock back 15 minutes early every single time so that you can just wean yourself. I love that advice. So we are talking about seasons of life. And I know a new topic that you talk a lot about is reinvention, right? And you've reinvented yourself several times. So talk to us about the different seasons of life that you've had so far. And where you are now.
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Chapter 3: What was Rachel's journey from blogging to bestselling author?
And that was my only goal was I thought, well, if you read my first book and you read my third book, As a reader, would you think I had improved as a writer? That's all I was trying to do. And Girl, Wash Your Face was honestly, I think, a fluke in a lot of ways. I actually think my ability to write fiction is why I have success in the personal development space.
because my audience are not people who self-identify as personal development nerds. It's not like Tony Robbins' entire audience goes over to me. I was speaking to women who maybe had never considered personal development before. They might not even have ever gone to therapy. They really had not considered these things at all.
So I think my ability to storytell and explain how I went through it and how it was helpful, that really was a massive unlock that wasn't in the space. Because I didn't really know how to be a personal development writer, I think that I brought something to it that maybe didn't exist before. But gosh, I cannot stress that enough to any of your listeners.
It really is an overnight success after working at it for a decade. It's like what we do in the dark that gets celebrated in the light. Nobody's going to cheer for you. Nobody's going to be there like rooting you on, especially at the hardest moments.
the process enough to keep going because you know, you don't know when, but you know at some point you're going to get the results that you're striving for.
I know even in my own experience, I started my career in radio working at a hip hop radio station. Nice. And then I had all these different music. I had a music blog in 2012. I had all these different music online radio shows before podcasts. And Young and Profiting was my fifth show, but it was my first business entrepreneurship type show.
That's great.
And then it worked out when the other shows didn't work out. So I always love to tell my listeners, there's no one straight path to what you want. You want it to be an author that had an audience. You did it in a slightly different way and something changed with the way that people were really receptive to it and it worked. Yeah, absolutely.
Yeah. And I think going back to that idea of the audience, if you figured out your customer base, if you figured out your audience, and even as you were changing the format of your show, you were learning how to do a show. You were learning how to be better. You were learning how to tell jokes or do an interview. So nothing is wasted. Nothing is lost.
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Chapter 4: What was the viral moment that changed Rachel's career trajectory?
Chapter 5: What lessons did Rachel learn from business setbacks and failures?
caveat or add a little bit here, for someone who does need to be up early and they really want to have a morning routine, they want to be a morning person, but they don't feel like they are, that's a learned skill. Nobody comes into this world, nobody gives birth to a baby and the doctor looks at the baby and they're like, oh, it's an early riser. That's not a thing.
So if you want anything in life, if you want a habit that you don't currently have, you can teach yourself that habit. So if I were you, and let's say you get up every day at seven and you want to get to a place where you're part of the 5 a.m. club. Set that alarm 15 minutes earlier every single day. Let your body adjust to getting up earlier.
Make sure that you have something exciting to wake up for. Like I love coffee. So it's really easy for me to pop out of bed. Or if I have a new book that I'm reading, because I'm super nerdy, but if I have a new book that I'm reading that I feel like I'm learning a ton from, that'll get me out of bed.
Have something that you're headed right into so that you've got a reason to meet your alarm where it meets you instead of hitting the snooze.
I love that advice, just setting the clock back 15 minutes early every single time so that you can just wean yourself. I love that advice. So we are talking about seasons of life. And I know a new topic that you talk a lot about is reinvention, right? And you've reinvented yourself several times. So talk to us about the different seasons of life that you've had so far. And where you are now.
Yeah, I don't know if this is every entrepreneur. I sort of think it is. A lot of my friends who are in the space or who are entrepreneurs, I feel like every five to seven years, there starts to be a shift. Or if there's not, I think the work begins to feel a bit stale. Especially if you're an entrepreneur, you're a risk taker, you're ambitious, you're competitive.
And so I think you're always looking around for what's happening in the market and how you might move with what's going on. So I actually started, my very first business was as an event planner. In Los Angeles, I started planning weddings and bought mitzvahs.
And then I slowly moved into getting to do corporate events, getting to work on movie premieres and press junkets and working in the entertainment industry. And then in 2007, 2008, I kept hearing about this thing called a blog. Everyone was blogging. I didn't really know what that meant. So I just started to blog.
I would literally write about what I ate for dinner last night and I just kept putting it out. And I had an intern one day that said, you know, blog's actually supposed to be about something, right? And I was like, oh, thank you. So I started to blog about events and how you could host events in your home and set a beautiful table.
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Chapter 6: How does Rachel advise entrepreneurs to diversify their audience and revenue streams?
Chapter 7: Why does Rachel believe in asking transformative questions in her latest book?
Have some humility. And I guess if you are going to share your successes, make sure that there's actionable advice of why you brought it up.
Right, right. Yeah. We do it too because women are so often underestimated in business. So we want to say, oh, but wait, I've built an eight-figure company. I have 60 employees. Like I've done these because you want to like legitimize yourself. But then simultaneously, I think people just the framework is they tend to hear that as bragging and you're not trying to brag.
You're more just trying to share your story. But yeah, I just think. Oh, I feel like such a like cheesy, but like be careful, be thoughtful.
I appreciate that. So how about somebody who maybe they're like you where they have to lay off a bunch of people, something happened where their business got turned upside down. They weren't expecting it. They didn't diversify enough. And now they're stuck in a spot where they feel like a failure because they tied their identity to their company and now their company sucks. So they think they suck.
Gosh, first of all, you're not alone. That's so many people. But I think that if you're feeling like that right now, you really need to study more successful entrepreneurs. Because if you study more successful entrepreneurs, you're going to find failures at the greatest, most massive levels. I promise you failures that are way bigger than what you've just gone through.
And the people whose names we know, it's because they stood up and went again. I sat down with Alex Hormozy a month or two ago, and he was talking about how many times he's failed. And if you follow his journey at all, you hear all these stories. It's like four times he's had these massive failures where he's been not just failed, but someone else has taken all of his money kind of thing. Yeah.
Where it would be so easy to get so bitter about that and to be like, see, like people are bad. The world's out to get me. I'll never succeed. And I asked him, I'm like, how on earth do you stand back up and go again when this happens for the fourth time? Not the first, the fourth. And he's like, well, because I figure at this point, I at least know what not to do.
I actually have a lot more information than I had previously. I'm back at zero, but I'm not at zero in terms of knowledge. So now I'm like, okay, I know how to build because I've done that before. And I know the pitfalls because I've fallen into them. He really sees that experience as this beautiful level up instead of as if he's done something wrong.
So just study other people and listen to other people's stories because you're going to hear that this is part of the journey. Failure is part of the path to success, period. And every time you reach a new level, you fail at new levels. Every single time you get to a new level, you're going to encounter ways that you're going to mess up or lose money or lose time or hire the wrong person.
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Chapter 8: What mindset shifts help entrepreneurs reinvent themselves after failure?
So if you could pay your bills in a different way, if you could maybe have a job that doesn't require quite so much, and maybe it's not as exciting, but like we're paying rent and we can like fully put our heart and soul because we have the energy and a higher vibration to put into the dream, I think you'd be shocked at what would happen.
And I feel like on the flip side, if you decide I would be an entrepreneur, I would do exactly what I'm doing now, I can imagine that that would really fire you up. And then you'd realize the highs and lows, it doesn't matter. I would be doing this no matter what. And I feel like it would make you feel more optimistic and inspired to do the work.
There's a fantastic book that everybody should read. Honestly, everybody in your audience. It's very small, super easy to get through. It's The Dip by Seth Godin. It's so fantastic. If you find yourself in a season of, do I really want to do this? Should I keep going? Should I stay in this? Should I go?
He gives this beautiful quote, which I reference in this book, is the opposite of quitting is not to continue to do the same thing. The opposite of quitting is recommitting with passion. So people find themselves and they're like, should I quit or should I keep going?
But if you decide not to quit, the way that you come back and you add life to that and power to that is you're like, not only am I going to keep doing this thing because I believe in my dream and I believe in my company, I'm going to show up, but you recommit with passion. You're like, I'm all in. You get fired up. You remember your why. You show up for what you're trying to do.
Because otherwise, you're going to be in the exact same spot questioning the exact same thing again next year.
So let's talk about another question. You actually opened the book up with a question. What must you let go of? Why is that important?
Because I think that the world teaches us that the answer to everything we're looking for is to add more things. The world's like, add a new house, get a new car, get a bigger job, make more money. And the older I get, the more I understand that the clarity and the sense of purpose and the real true impact of our work happens when we start to strip things away, not when we add to them.
So, you know, if you have people in your community who are working on side hustles and Same with my peeps and whether it's at a book tour or maybe they call in to ask a question on the podcast, I will inevitably have people who are like, I really want to build my own company. I'm like, that's amazing. Tell me about it.
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