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Jessica Zweig
Have you ever had the feeling that your business is good but it's nowhere near where it could be? That you're amazing at what you do? I don't doubt it, but you're undercharging, you're underseen and you're over delivering, sister. That ends now. This is your official invitation into the Feminine Frequency Business School. The most comprehensive embodied and elite business and leadership certification for women who are done playing small over 12 weeks. We leave no stone unturned. You're going to master messaging, branding and visibility, sales and marketing with sol. How to create your one of a kind offers and scale them with strategy. How to build systems operations, grow a team and step into your CEO embodiment. Plus you're going to learn from the biggest experts in the space on AI, social media, virality, meta ads, podcasts and PR. How to land a book deal, Legal Must knows everything you actually need to build a seven figure business in 2025 and beyond. This isn't just another course or group program. This is a transformational experience of building business redefined through the lens of the feminine. A modern day MBA program designed for women just like you who are finally ready to rise. And the results, well, they speak for themselves. We've had graduates go from $2,000 retainers to 10k months, from undercharging to closing $90,000 in contracts within weeks of graduating, to landing national TV segments and to hitting seven figures in revenue. Yep, in less than a year. If you are ready to be seen, paid and positioned like the expert you are. FFBS was designed for you. Doors close August 27th and spots are filling up fast. So go to jessicasweig.com FFBS linked in the show notes and book your call with me and my team today. Now this program sells out every single round and it only opens twice a year. So trust your gut if it's pulling you towards this. I feel that sister, this is your moment. Let's build your brand, let's build your platform, let's build your wealth, let's build your impact and most of all your feminine legacy. Together. I cannot wait to meet you inside of FFPs. Link to book. Your call is in the show notes. Welcome to the Spiritual Hustler Podcast. I'm your host Jessica Zweig, multi seven figure serial entrepreneur, best selling author and branding and business coach. And this is a show where we are redefining the word hustle, reclaiming our true feminine nature of magnetism and putting down the self judgments and shame around loving to work and making a lot of money at it.
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It's going to make you a whole lot richer too. This is the Spiritual Hustler Podcast. Well, hello and welcome back to the welcome to the show my beautiful, beautiful spiritual hustlers. I'm so excited to drop in with you today on this extremely special episode. I am bringing you a conversation today that I had with my dear friend and a woman that I have admired and aspired to be in her orbit for for years, for over a decade. And Lindsay Pinchuk is the founder of Dear Found her a consultant, an exited founder. She actually sold her business a couple years before I sold mine and I had Lindsay on my podcast back when it was the Simply Be podcast. I was still running my agency and I brought her on the show to talk to me about her exit. And I took such serious notes because I had in the back of my heart, actually, if I'm being honest, in the front of my heart, a goal to sell my business too. And lo and behold, as you probably know, if you've been following my journey, that I did sell my business and rebranded my life, including this podcast, launched my own personal platform, have become a full time coach for female entrepreneurs, helping them throughout my business school and my retreats and masterminds and everything that I created, not just in the Simply Be chapter, which was a business that I started from nothing and scaled and sold as well as the business that I started before that, Cheeky Chicago. It was an online magazine that I ran in the city of Chicago for seven years that I scaled and failed and took all of those lessons and poured them into the Feminine Frequency Business School to really help women stand up in the market as actual owners of businesses. And the doors for the Feminine Frequency Business School close tomorrow. So if you're listening to this podcast, you've been following this journey. We had a beautiful launch event with the Brilliant Summit and we've welcomed in women from across the world and we have just a few spots left. And if you are interested in joining this incredible community. You can book your call. One last chance. I'm going to leave a link in the show notes. But as far as my actual experience selling my business, it wasn't all butterflies and rainbows as it never is. And Lindsay herself knows that all too well. And so she actually had me on her podcast, Dear Found her, which is a massive show. She is interviewing some of the biggest female entrepreneurs in the world, has scaled her platform in such a short amount of time. She's definitely someone to watch, to follow, to listen to. But her and I dropped in on this conversation in a really raw, really honest, pretty transparent way that I really haven't shared elsewhere. Because to sit down with another founder who understands the experience of selling a business and have that heart to heart was really, really powerful. And so I wanted to take you guys into this conversation to hear a side of that story that you probably haven't. And I hope that no matter what you take away from this conversation, that the biggest thing you take away is that anything that you put your mind to, you can achieve, you can accomplish. But that it's okay to change your mind. It's okay to feel in alignment for so long and then one day not to pivot, to think bigger, to rebrand yourself, to allow parts of you that are no longer you to die, to fall away, to peel off so that you can really step into the woman you came here to truly be. And I'm so grateful to Lindsay for welcoming me on. She's such an incredible interviewer, you guys. You're gonna love her and you're gonna love this combo. So without further ado, here is my amazing conversation with Lindsay Pinchuk on the podcast Dear Found her on what It Was really like to Sell My Company.
Lindsay Pinchuk
Today's guest isn't just any guest. She's also my friend and someone I respect madly and deeply for living her own entrepreneurship journey. Jessica Zweig and I basically lived parallel lives for many years, and we didn't even know each other. While I hosted events for the Expectant Moms of Chicago, she was hosting events for the singles of Chicago. And it's almost crazy that our paths didn't cross for real until just a few years ago. After I sold my company and I wanted to leave, a mutual friend of ours encouraged me to reach out to Jess for advice. And I will never, ever forget the support that she gave me during a time when many in my life just didn't understand. Jessica's not only an incredible business person and a branding expert, she is an amazing human being and one who never ever forgets where she came from. This is Jessica's second time on Dear Found her as today we're celebrating a huge milestone of her own, the acquisition of her company. Jess has been described as a voice of her time by Marianne Williamson and a personal branding expert by Forbes. She's a serial entrepreneur and a three time founder and she recently sold her agency Simply Be, the nation's premier personal branding company. She's also written two books. Her first was a number one bestseller, be a no bullshit guide to increasing your self worth and your net worth by simply being yourself. And her latest release, the Light work, reclaim your feminine power, live your cosmic truth and illuminate the world hit shelves in August 2024 and was named a USA Today Best Seller. Congrats, Jess. She's also the host of a top ranked podcast, the Spiritual Hustler and is a highly sought after speaker for companies like Google and Nike. A leader of a global community of spiritual women and hosts sold out retreats in business, branding and spirituality across the world. I am honored to have Jessica Zweig back on Dear Found her and cannot wait for you to meet her. So let's get this started. Come on in and meet my friend, Jessica Zweig. Welcome back to another episode of Dear Found Her. We have a second time guest here on the show today and that guest and I go back a long ways. We randomly were running parallel businesses back in the city of Chicago. We were creating events. She was creating bar nights out for single women, I was creating dinners for pregnant women. And yet somehow we found each other next to each other at the Apple Genius bar one day with our computers and I was so nervous. I didn't say anything, I didn't say hi. I was like in my head, oh, that is Jessica's wag and she owns that great company and, and we never talked in that moment. And then fast forward years later. We both are founders and we were connected. And since we have been connected, I feel like it's been about three, four years since we first connected. We have never not been connected. And Jessica's wig has become someone that I know I can rely on, I can count on. I call her a friend and she recently sold her business and I'm so fucking proud of her. And I cannot wait to share this story and to dive into this conversation also because Jessica had me on her podcast to talk about selling my business and it was really, I think a fact finding mission. And so now here we are and her business is sold and she has started her 3.0, and I'm so happy to have you back on the show. Welcome back, Jess.
Jessica Zweig
Thanks, babe. I'm so happy to be back. You're amazing. I. I'm a listener of your show. Like, I am a Lindsay Pinchuk fan. Thank you. I never knew that story about the Apple Store, so thanks for sharing. You could have totally said hi to me. And secondly, you are an expander for me. I had you on that show, my podcast, back then, to really dig into how you did it, because I knew I was going to do it at some point. And it's very cool to now call us in the same sort of league, for lack of a better word, of exited female founders. It's a very small percentage of us. And I'm proud to stand next to. To you in this.
Lindsay Pinchuk
And I'm proud to stand next to you. And the interesting thing is, is before I was on your podcast, we had dinner with another mutual friend of ours, Charlie. Charlie Safra. I'm gonna give her a shout out. She was an amazing guest on this show. And we had dinner, and you were asking me a lot of questions at dinner about the sale of my company. And, you know, you. You alluded to one day wanting to sell Simply Be, and you said to me, you know, I really want to do something a little bit more spiritual. I'm just kind of feeling it in my soul. I. But it's not going to be for a while. And that was kind of when we had the idea that I would come on your show and we talk about selling a business and. Cause I was telling you all the good and the bad and the ups and the downs. And I really didn't think in that moment that it was going to happen, as you did not allude to the fact that it was going to be as soon as it was. And so when I saw your post, I woke up one morning to your post that you sold Simply Be to Hawk Media. And I literally fell out of my bed because I was like, fuck, yes. Like, this is amazing. And. And so I'm just. I'm just like, so. I'm so proud of you. And I know this is my second time saying it, but I really am.
Jessica Zweig
And we.
Lindsay Pinchuk
We really have talked about this a lot. So I would love for you to kind of give a smidge. You can go back to your 1.0, like, a little. But they can also listen to our other episode, just a smidge about who you are, how you became a founder and kind of where you are today. And. And how you sold it. We'll get into how you sold the business. Don't tell me how you sold the business, but just give us a little your story.
Jessica Zweig
Well, it's good to be back everyone. Thank you again for having me. I loved our first interview so we can go back and maybe link that in the show notes. But to give you the bridge version, I've I'm a serial entrepreneur at this point. I've started three companies. My first company was started right around the same time Lynn started her company the Bump Club. I ran a magazine called Cheeky Chicago dot com. We were the lifestyle it magazine for young millennial women in the city. While that was a very successful brand and we did great things, it was a hard knock. It was like the hard knocks lesson. Real life MBA of entrepreneurship. Made a lot of mistakes on a lot of levels and ultimately left to go off and start my next thing on my own. I was really ready to spread my wings after seven years of running that from 26 to 33 or whatever. And I got this wild idea to help people build their personal brands with all of the marketing know how I had adopted from working with major brands as our sponsors and advertisers throughout throughout the cheeky chapter and help people get online more authentically and clearly. And I really think that simply be started. While I was really great at what I did, it was also divine timing. It was like striking when the iron was hot. This was 201617 when everyone all of a sudden was like I should be on social media. And my my agency which turned from a one woman consultancy into an agency, full service agency exploded. And we'll talk about that explosion and all the things that came with it ultimately exited it about almost exactly a year ago and I started my third 3.0. I love that lens. I'll steal that. Really just being me as a coach, I'm working with all sorts of female entrepreneurs across masterminds, group coaching, certification programs, retreats one to one blending business everything. I obviously learned about branding, personal branding specifically and spirituality, divine feminine leadership, our feminine identities as women in business. I think it's such an important part of how we do business. That took me a couple years. Learned the hard way the cost of not incorporating my feminine identity and how I was running my agency. And so yeah, here I am today. You know, got a lot, got a lot of war wounds, got a lot of success stories. I guess you could say that. And I'm really here to uplift other founders the way you are.
Lindsay Pinchuk
Lind, you know what I think is so cool when I think about your story, and my story is that, like, they are so parallel, you know, I mean, like, we both were. We both started companies to help the life stage that we were in, and we did it very successfully, both of us. And when we left both of those entities. Yes. You had a little space in between, and I did not. But now we are both really in our own. Helping women to do what we've done in the way that we've done it.
Jessica Zweig
Yeah. I'm telling you, I'm. I'm in love with you. Every time I see. I follow you, I. Your stories pop up because I follow you so much. Right. You're in my algorithm. I just have been watching you blow the F up the last two years. It's unbelievable. And it's.
Lindsay Pinchuk
I mean, the last year, though, specifically the last year, you and I can have a separate conversation about personal branding because I'm having a crisis of my own. But, you know, but it's true, you know, I mean, the last year has been very different. So thank you for saying that. I. I mean, I appreciate it, but I think that, like, the. The thread, though, the common thread, is the fact that, like, you and I both feel so fulfilled just watching others succeed. And. And that's evident in when you watch your social media, when you listen to your podcast. It always has been evident. I mean, the minute someone introduced us, it was Heather Reddish who introduced us. And I didn't say that before. It was Heather Reddish who, like, really made the introduction. And you were so willing, even though you were in the throes of your agency, to hop on a zoom with me and just talk to me, because I had just exited and left, and I was stuck, and I didn't know what I wanted to do. And. And I so appreciate that about you, and I love that you are. You are making that your career move.
Jessica Zweig
Thank you. I really receive that. Thank you. I think there's nothing more important than walking the walk and being a woman for women and really being generous with your time and recognizing that when someone else wins, you win, too. And there's just no better feeling and healing than coming together as female entrepreneurs and having each other's backs and being available and accessible. It just. I believe in reciprocity, generosity, circulation, and, like, it all comes back. And we can't be, you know, platforms that say we support women without actually freaking doing it, like, as. As a job, literally for us, but also as a daily practice in the way we do business life.
Lindsay Pinchuk
Let's go Back, though, to simply be. And to, you know, a few years ago when we were having dinner and you were telling me, you know, I do think one day that I would like to sell my company. And I'm not really sure what that looks like and how did that look like for you? And, you know, we had all those conversations and, you know, you were running a very successful agency that, like you said, blew up. Your husband was in business with you, and which I always thought was amazing, and you had an amazing team. What was it that really kind of was the catalyst that said to you, I'm ready to sell this, I'm ready to move on?
Jessica Zweig
Yeah, you're so intuitive about that dinner, Lindsay, and the podcast, because I was digging for information from you and. And the things you shared with me, by the way, I didn't forget in my transaction. I took notes. Good. So, you know, when I first started the agency, like I said, it was a one woman shop. I left cheeky. I didn't really have a strategy or a client even. I just knew I could help people and was passionate about personal branding. And I hit seven figures in 18 months. Like, it just. It just started really running. And I had a dinner with one of my mentors. This was like in the first two or three years of the agency. And he asked me at that dinner what was my. What's your business plan, Jessica? It's like, what are you talking about? I have a business plan. I read the book Traction. I'm following this model like, I've got this vision. It's working. He goes, no, what is your plan for the entity of the business? Where do you want it to go? Where are you taking it? And I was like, I didn't have the answer. And he said to me in that conversation, I'll never forget it. It changed the course of it all. He said, you have a few options. He goes, you can run it for the rest of your life, make it a lifestyle business, and that's fine. You can eventually close it down, go do something else. I knew my ego would never really let me do that. He said, you can create a session plan and have somebody come in and run it for you while you still own the entity and do whatever else you want, or you can exit it and sell it.
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And I remember in that moment just saying to myself very quietly, like, I didn't really, you know, I was processing his advice. It's like, I think I'm going to want to sell it one day. I think that's really where I wanted to go. Right around that same time, I brought in a very incredible fortuitous, fractional coo. Her name is Amy Schuster. Shout out to Amy Schuster. And I told her I wanted to sell the business. As my executive consultant, she had sold a few businesses herself. And she came in and she did a quarter long analysis. She said, you, if you want to sell this business in the next three to five years, you have four problems with this business. They all start With a letter P. You need to get your people right. I didn't really have an organizational strategy. We had too many, like founder, original kind of mission critical hires that if they got hit by a bus, which God forbid they wouldn't, the whole business would go down. We needed to really staff up, process. We had no process systems to really operationalize the business. Pricing, we needed better profitability. And the last was perception, because she was like, everyone thinks this business is you and you're not for sale. And so that began the kind of internal, quiet, rebrand, repositioning, restructuring of the business. And by the time Hawk Media came knocking, which I'm happy to get into the details of how that whole thing manifested, we were, we were ready. The business was an asset. It was running without me. There were clients that never had met me. My people were a list plus talent. We were operationally efficient, we were profitable. And so all of that was a journey. You know, it took me seven years to be able to say any of that was true. But that seven year mark is when Hawkins called.
Lindsay Pinchuk
So it's interesting because something that you did and that Amy told you to do that. No one told me to do that. I regret, not that I regret. I guess I just didn't know was taking you out of the business. And that's something we talked about too, at great length many times. You know, I think that you're right. You're not for sale. And when Bump Club bought, when Advantage bought Bump Club, a big problem was that I was still the face of this and no one knew how to take me out of it. And it. And it was a hard situation.
Jessica Zweig
I feel that in my body. That's heavy. That's heavy stuff.
Lindsay Pinchuk
And it was tough. But I remember, I really vividly remember, like after our dinner, after I was on the podcast taking better mental notes of what you were doing and watching you come out of the business. Like you had someone else do the podcast with you. I did. You know, you were doing things that were like, you were focused on Jessica Zweig on your Jessica Zweig account on Instagram, and you were focused on Simply Be, and it really wasn't about you at all on Simply Be. And I would say the only kind of thread was when there was news about you and your color. Yellow.
Jessica Zweig
Yeah, yeah.
Lindsay Pinchuk
I mean, that was it. But. But you guys did it very smart. So what happened when Hawkins called? Like, what was that process? Were you trying to sell it? Was it out for sale or was it just like a call that happened and they were like, hey, we're interested.
Jessica Zweig
So Hawk Media called me, reached out to me for the first time in December of 2020. Okay. So I didn't sell to them until July of 2023. So I get an email from this random dude, Hawk Media. They're looking to buy agencies. And I was. So this was two months before my first book B was about to come out. I was, like, deep in the pocket. I was growing it, loving it. Like, no interest in selling it. But I was like, you know what? I'll take this guy's call just to learn, just to get to know.
Lindsay Pinchuk
Always take the call.
Jessica Zweig
What he's. Always take the call either. Absolutely. It's an education. And we talked. He was cool, but I was also. I was a little cocky in a way. I was like, you're gonna want me more in a few years. Like, I'm just about to blow up. And in a way, I did. But, like, there was also a lot of shadow side to that, which we can talk about. And anyway, so Hawk kind of dated me. Like, courted me. Like, that guy didn't leave me alone. His name was Josh. He reached out to me every other quarter, every six months, every four, six months, for two years, three years. And I knew the business was going to grow in its value, and I wasn't ready to sell it. But I kind of kept them on the back burner of my mind. Then flash forward to July of 2023, and we actually had a really. It was a really tough month, actually. And I won't get into the details why. I just found her life. And I was kind of past the point of my burnout. I had been working on my new book, the Light Work. I had hosted that retreat with Charlie Safro. Like, my. My heart was starting to open into the next horizon. But I was still in the business, right? I was still deep in the business. And I remember looking at my husband, Brian, who I hired as my CFO in 2020. I. He worked for me. I hired my own husband. He was my partner. And I looked at Brian and I said to him in July, I think I'm ready to. I think I want to start thinking about an exit now. I was mentally kind of done. And I. Hi, this is my spiritual self. Believe in the power of the universe and everything being divinely orientated. One day or two after the moment where I turned to Brian and said that, two things happened. One, I got an InMail from LinkedIn like you did from the private equity company wanting to buy my company. I was like, wow, that's the universe listening again. Two days after that, Hawk, Hawk Media, hadn't heard from Josh in months. Sent me an email. I actually ended up. Most people don't know this. I had two offers to buy my business in the same month and the same like summer long window. And I evaluated both of them. I had two offers from a PE company that essentially just wanted to take my business, milk it, make it an asset, sell it, and then there was Hawk. And I weighed them both and ended up going with Hawk.
Lindsay Pinchuk
What was it about the offer that made you want to take the Hawk offer?
Jessica Zweig
So Hawk was a strategic buyer, right. And the other company was an equity buyer. So what the equity buyer was attempting to do was create an ecosystem of multiple agencies to blow out into like an enterprise business. And they were buying up small boutique firms to get there. But they were very much equity forward and they were actually really nice guys. They just were, you know, their lens was profit. And with Hawk, what the equity guys were attempting to do, Hawk had already done. Hawk had created this over 10 years of building a 200 person company, amalgamating boutique services to create specialties under one roof. And they weren't looking to milk my business. They were looking to grow my business. And they were willing and able to keep my entire staff. That was a huge prerequisite for me. Whereas I felt like the equity guys were going to come in real quick and cut and clean house and right. Size it and make it super profitable and percentage margins, et cetera. And Hawk was willing, really willing to keep my brands. I set a lot of criteria with, with Hawk from the get go and you know, we went through the due diligence phase and you know, like planning your wedding, it's all fun and roses kind of it's one big dog and pony show of how amazing you both are. And you know, there were some really great green flags throughout that process. And you know, it shifts once the business is no longer yours, which we can talk about. But I just felt like a strategic buyer given where I, how much I had invested in the brand, the reputation, the quality of work, my people. I had 25 W2s. Like I didn't want anyone to go and I had to fight for certain things, of course, but I just knew that strategic buyer for what I had built was better than a PE buyer.
Lindsay Pinchuk
I thank you for sharing that because, you know, I mean, very similar to with Bum Club. I didn't have three offers, but we had three potential buyers. And the one I went with, very similar to you was like, they wanted my whole team, and that was a really big piece of it. And I think that that speaks to you as a person. You know, it wasn't just about the sale of your company or being part of the 1% who has sold. It wasn't about that. It was about making sure that the people who gave to you were being taken care of. And I think that that is so important. And, you know, there's something to be said just about karma and, you know, taking care of your people. And I think that it's important in all aspects of life, but especially in this one.
Jessica Zweig
And I think it's a value that we should celebrate in ourselves as women. I mean, I really led that whole company and culture from a place of genuine love. And I. I don't need a gold star. I'm patting myself on the back, but, like, I put them first always, you know, always.
Lindsay Pinchuk
And you paid them before you paid yourself and. Yes, of course.
Jessica Zweig
And actually, as you're saying, actually would have made more financial sense to me in certain ways to take the deal, but I didn't want my business to become just an asset like I wanted it to remain. The beauty of that brand was the way that we created these client relationships and empowered my team and how my team operated with each other. I was. That was the proudest thing I created, actually, was my team. And, you know, obviously, things shift when it's no longer your business or your culture, but my. Most of my team is still there. And that says a lot.
Lindsay Pinchuk
That does say a lot. Let's talk a little bit about the shift. I mean, you talked about the green flags, so I would love for you, if you can, to weigh in on any of the red flags. And this was something that you asked me when I was on your podcast and I think is very important to talk about because, yes, Jessica sold her business. Yes, she had a successful exit. You know, she's. She's still loosely tied and she's still involved, but we can get into that. But it's not all roses and unicorns. And selling a business is really hard, both physically and mentally, and it's like mental gymnastics. So I would love for you to share what some of those shifts were and some of the red flags were that, yeah, could help another female founder.
Jessica Zweig
Totally, totally. So when it comes to the red flags, I'll say something to your community that you said to me. Get as much in writing as possible, like make sure your asset purchase agreement, your exit agreement, whatever legalese and documentation you will need to have that you put it all in writing. However, there are certain things that go in writing that aren't always. There's can be different interpretations actually of what's in writing. That's something to flag and to note that there are going to be things you can't even think of in that transactional moment that you wished you would have put in writing.
Lindsay Pinchuk
When you're in this moment, anyone can tell you in hindsight, or you can tell yourself in hindsight, but when you are in the moment and you want out and you want to sell the business, there are going to be certain things that you are like, you know what? I don't give a shit.
Jessica Zweig
Right. Right. So, for example, I mean, I'll. Let me just say this actually let me back up and then I'll come back to the. To the transition point. Okay. So I say this to founders who are interested in selling their business that I talk to. I believe that two things really, truly need to be in place in order for you to even get to the point of selling in the first place, which is one, your business has to be an asset in a perfect world that can run without you. And that from just from a pure tactical, operational perspective, your business has to be an asset. No longer a lifestyle business that require you in every single decision. The second is that you as the founder, mentally and emotionally, have to be ready to let go. Like, really let go. And I was in this energy, to be totally honest, where I was like, I'm done, so I'm really ready to let go. Like, that's not an issue. But then the lights go off on your business, and the next day the lights come on and it's not your. It literally was like that. It was like, Cliff, like, December 31st was our last day as an.
Lindsay Pinchuk
Me too.
Jessica Zweig
January 1st, stop.
Lindsay Pinchuk
Yeah, I was like going to New Year's Eve and I had. I got the check even like that, like, and then on the 1st, it was new Year's Day. That's what it dropped on the wire.
Jessica Zweig
Wow. See? Same. That's wild. So we. We actually had to wait a couple weeks to announce it to the. We had a whole strategy and we can talk about that actually as well and how clients and community and how to manage and the news. But back to the internal ops that was going on, like, literally. Lindsay, it was. It was so drastic, the change. Like December 31st, I was the owner of the business, and January 1st, I was an employee. And within a matter of the first business week of the year, I'm not Copied on emails anymore. I'm not included in Slack conversations. I'm not invited to certain meetings.
Lindsay Pinchuk
How did you feel about that? As someone who wanted to let go, how did you feel about that?
Jessica Zweig
Enraged. Like, I. I got over it. Don't get me wrong. I had to remind myself Q1 was rough. Let me just say this of last year, of this big shift, because I was a. I was like. And I had to remind myself all the time, this is what you wanted. This is what you wanted. You have to surrender. This is a gift. Be grateful that you're not in. You're not being copied on these emails. Be grateful that you've been literally cut out of that decision. How can we not be enraged when it's our baby?
Lindsay Pinchuk
It's your baby.
Jessica Zweig
Exactly. So those are the micro things that I didn't think about. Like, could there be a transition, a passing of the baton versus me no longer needing to be in any single leadership meeting and talking about clients or really understanding the distinction. So we're an agency, right? The agency space is very customer focused in my view. It's very white glove, very high touch. I don't think agency life should be transactional. It's a relationship that was a philosophy that we had around at least how we did sales, right? And because of that, the way that simply be was structured, the sales team and the account team were completely intertwined. Like the right hand talked to the left hand every day. Like we brought in a client or a prospective client and we would talk as one team if that client was the right fit. Like, could we really help this client? When was this client able to begin? When did they want to begin versus when we had the capacity to onboard them. Right? Like everything was made together and you come into a bigger company and it doesn't operate like that. They are siloed departments. There is no real left hand, right hand talking. It's like, let's get the money in the door and just deliver the work. And there's no partnership in that capacity. And hey, look, Eric and Hawk, They've built a $50 million company. They're doing something right, you know, and I had no jurisdiction. My opinion didn't matter. Like we had to follow suit.
Lindsay Pinchuk
So the first quarter was. Was rough. Now let's talk about where you are today.
Jessica Zweig
Yeah. So in the first quarter of the year, actually right around that same inflection point, you know, and I had had my horizons now defined. I was very clear that once I sold the agency, I was going to go and launch me. Jessicasweig.com As a coach and a consultant and helping women in all sorts of modalities in person on group online programs, one to one with this new wealth of knowledge that I now have. And I launched that business in March, and it just took off. And I'm very grateful to say that, like, I got clients rebranded my podcast to the Spiritual Hustler. The analytics grew my social.
Lindsay Pinchuk
So did they not buy your podcast? Was that not part of the sale?
Jessica Zweig
Nope. I did not exactly. I, I, they could not have my podcast. That was written in the APA because I knew I was going to rebrand it from simply being.
Lindsay Pinchuk
And you wanted the listeners 100%.
Jessica Zweig
I want to keep my RSS feed with all of those listeners. And the response to that was amazing. The market really similar to what you were saying. You know, you were, you fell off your bed, which I really appreciate when you saw the news, and I was not. I was expecting people to, like, be excited, I guess.
Lindsay Pinchuk
No, everyone gets so excited. Are you kidding?
Jessica Zweig
Yeah, it's so, it's so. It was actually really fun. I was like, wow, people are deeply engaged in this, and all of a sudden you're on everyone's radar. And what are we gonna say?
Lindsay Pinchuk
I was gonna say, oh, no, just keep going.
Jessica Zweig
Keep going. Well, it was something that I, you know, when you sell your business, it's an, it's an asset. It's a story to leverage.
Lindsay Pinchuk
Right?
Jessica Zweig
It's. And you should. It's such an incredible accomplishment, and to do it as a woman is even more amazing.
Lindsay Pinchuk
And you're now an acquired founder. It's part of your story, and it also allows you to do a lot of the things that you're doing today. And that's how I always looked at. It was like, even though it wasn't rainbows and unicorns and I, and I. Things did not always work out the way that I wanted with the sale. It put me in a position to do what I'm doing right now and, and to tell others and teach others and work with others, and that's what I want to be doing. So to your point, it's part of.
Jessica Zweig
Your story, and it's worth it. All that pain, all of it, all that stress, it's so worth it. And so Q1 quickly turned into Q2. And all of a sudden, I was doing me, and it was beautiful. And the stress and gripping and annoyance and grip, like, gripping. Just lessons because I. My attention was being pulled elsewhere into something that was really giving me life. And, you know, I, you know there was some changes they made within the business. And I, I won't go into too much detail that I, I didn't necessarily agree with or didn't make me happy. And I found myself over the course of this last year, I don't want to say caring less because that sounds so harsh, but I noticed a shift in. I really did surrender and it was really freeing.
Lindsay Pinchuk
It's not that you don't care. You let go.
Jessica Zweig
Let go. That's right. I did. I did. And it happened. It took me about six months to fully feel like when I would hear something that happened that I wouldn't. Neutral, Completely neutral.
Lindsay Pinchuk
So now I know, like, you're like loosely tied to the business. Correct? Because people are going to want to know, are you still there? Are you still working there?
Jessica Zweig
Yeah. So basically what I, I am connected to the business forever financially. And I am essentially a sales person, spokesperson for the brand. And any leads that come through the agency, through, through my network, I, I open into the, into hawk. And that's really, it's very reactive. I'm, I'm not going and hunting for business. I do get enough solicitations from my network at, throughout the last year. Can I still hire Simply Be? Yes, I, I facilitate the deal. This is essentially what I do. But I'm not an employee of the company. I'm not a contractor. I just basically am that face and the spokesperson for Simply Be, where and when it makes sense to the market and I bring in business.
Lindsay Pinchuk
And now you're living your best life. And so let's talk about that.
Jessica Zweig
I'm very grateful for where I am because it hasn't always been like, oh.
Lindsay Pinchuk
My God, you are living your best life. And I, I love watching it because I know your story and I know that there were a lot of hardships. And just listen to part one of me and Jessica. I'll link it in the show notes. But I mean, you know, it was not always easy. You were in debt. Like, you, you had issue, like, you had like a lot of things that you had to overcome. And so, you know, I don't want people to be sitting here listening. And I'm saying this because I don't want people to be sitting here listening like, oh, she sold her business, she's got it made. Because you and I both know that that's what a lot of people think when they hear you sell your business. And it was a lot of fucking hard work and hardships to get here. And you deserve it. And I love watching you do what you're meant to be doing.
Jessica Zweig
Thank you.
Lindsay Pinchuk
You know, I mean, so when we had dinner, I remember this very clearly. You said, I have an outline for my new book. And you're like, but it's very different than the other book because it's, you were like, it's very spiritual. And you know, and so then the book came out, like, you know, and I know, like I watched you online, like I watched you on Instagram when you, you went to Costa Rica. I think it was right. Yeah. To write your book and, and whatnot. So you have a new book called the Light Work, which is a USA Today bestseller.
Jessica Zweig
Congrats. Thank you. Thank you.
Lindsay Pinchuk
Tell us a little bit about the book.
Jessica Zweig
The book is one of the, you know, I say this with, again, a lot of humility. It's one of the greatest things I've ever done. Not because I think it's, it's not about me at all. It's really a message for women that just happened to channel through me. You know, it's important to note and I don't know if we touched on this on the other podcast. I don't remember exactly when we recorded that, but at the peak of Simply Be, when I was making the most money, I had the biggest team. I had written my first book, I was winning awards, I was being asked to speak across the world. When I was at the peak of my career was actually when I was the darkest inside. I really wanted to burn it all down. At one point I was burnt out, diagnosed with depression and physically, mentally, emotionally, like actually burnt out. Couldn't leave my house for weeks and months at a time. That level of darkness. And I went on a very profound spiritual pilgrimage to Egypt at the end of that year and got a whole bunch of new information that that trip just fucked up my life in the most beautiful way. I had a real full on identity death in that country which I write about in the book. And I came back from that trip. I've always been spiritual, Lindsay, you know, you know that about me. And I was kind of testing like retreats and sharing certain things on social media. And I just decided to step fully out of the spiritual closet with my beliefs, with my perspective on what's really happening here on this planet and how it relates to us as women. High performing, most likely, probably hyper vigilant, hyper perfectionist women that are conditioned to like diminish their power or work in a certain way or hate themselves because the matrix has told them our bodies aren't beautiful. Like all of it. Is in the book and I launched it this year and the response has been amazing. I feel like women are really seeing themselves in it. I have so many intentions with that book, but one of them is that the reader never feels alone again in her own darkness and have really come out of, you know, the identity as a boss babe, which I am. And I'm very proud of being a good, I'm good at business. It's a superpower, but it's not the whole story. I don't think for any of us. I think we are so much more than what we do. And that's really been the movement of light that this year has been for me. It's been exhausting. I'm. Book launch years are no joke, but I, I needed to pour my whole heart and soul into that launch to get it to where I knew I needed it and wanted it where it deserved to be. And thank you for saying that. I'm living my best life because it's been, it's been dark a lot. And to come out on the other side feeling totally in alignment.
Lindsay Pinchuk
I'm so happy for you.
Jessica Zweig
Thank you.
Lindsay Pinchuk
I am. And I think, you know, a big, a big thing. A big piece of the book launch is, you know, obviously Jessica Zweig is the queen of personal branding and she rebranded herself in 23. This book fits very nicely into the portfolio of work that she's doing, obviously. So in addition to the book, I want you to kind of share with us what you're doing and how you're working with people because it's also been really awesome to watch. I think you just sold out a retreat. Congratulations.
Jessica Zweig
Thank you. Thank you. So essentially it's so much fun, you know, to build a new business and you can call yourself a coach and that can mean a lot of things. And I really, I get super turned on by like business modeling and product suite development. Right. So I have a whole product suite now within my, my new organization and I do one to one coaching, but very selectively. I was doing that predominantly for a time, but it's now scaled up and it's hard to scale a business when it's just you in the one to one capacity. So all that to say I've created and trademarked a school, a business school. It's called the Feminine frequency business school. It's a certification program. So you go through my program and you leave. Certified with an accreditation as a, as a up leveled entrepreneur in the space of consciousness and business at the same time. I have 54 women in my Current cohort which has been incredible.
Lindsay Pinchuk
Amazing.
Jessica Zweig
Yeah, I launched that, I'll be launching that again in February. I have a retreat that I do once a year that's pretty much one of the most amazing productions I've ever done. I've done this now three times and out of my retreats I host a mastermind. So I do a six month mastermind twice a year and I will be converting. I don't know when this goes out but I'm sure it's fine. I'm. I've created an ongoing membership program out of my school for ongoing continued cohorts, office hours, Masterminds, Q&As, many masterminds, that kind of thing. And really I'm just here to help women rise in business while activating their feminine power. My business school teaches for example marketing, branding, sales, products ops team. But we use the goddesses of Egypt every module to talk about how we activate our feminine ancient codes and to show up differently, more embodied in our true identities as female leaders. So it's been so much fun. I have the best little mini team. I have five people that work for me. I'm never going to have more than that and hopefully and it's just been, it's been like I said, I'm an alignment and the women are incredible that I get to support what would be.
Lindsay Pinchuk
Like three lessons that the sale taught you that you're applying now to your business.
Jessica Zweig
Wow, that's good to really follow. Follow your gut, follow your instincts. I feel like when I did have those two offers on the table they both and I have zero regrets either by the way. To really follow my, my gut in every decision and to let my sacral solar power like be the thing that guides me more than my emotions or my mind. To really listen to my body. The second thing I'll say I didn't share this and I'm glad, glad you asked this. When Eric made me the deal, I flew to LA to meet, to meet him in person because I was like I need to meet the human being that's going to buy my company. We had coffee and I told him at that coffee where I was going and what I wanted. I was extremely forthright. It was a little bold. I was like these are, these are my criteria. If you are going to buy my business, you have to keep my people. It has to be at this financial structure. I want to be able to go off and do my own thing with no strings attached to like I want you to help me with the press and the story and the media behind, like I was very, very clear. And I look back on that moment and I'm kind of like proud of that version of me. Like, don't be afraid to ask for exactly what you want. Yes, get it in writing. But the first step is saying what you want and finding the courage within yourself. And I think the third thing is, you know, take your reputation seriously. Like, your reputation is your asset and it doesn't necessarily mean it's your personal brand name. Your reputation comes in the form of the way you treat people, the way that you interface negotiations, how you honor your team, how you communicate with your clients. All of that's your reputation. It is your biggest currency. And to not take anything you do for granted and to have self awareness and to just honor the work that you've put into to building that. Yeah, that's what I would say.
Lindsay Pinchuk
Okay, and then a spin on my last question. Jess, I want you to think back to Jessica Zweig at Cheeky Chicago. She's just getting her business started. What are three actionable steps that you would tell her?
Jessica Zweig
Go to therapy. Do your own work. Start young, Start doing it now. Learn how to be a better communicator. Learn how to take personal responsibility. To be a great leader requires you to be a great person. And to start that journey sooner, it'll just accelerate everything. The second is to know that experience, resume whatever has, like, been on paper. Doesn't matter that you have it inside you to figure it out on your feet and to trust yourself more because no one's going to believe in you unless you believe in yourself. And it's okay to fake it until you make it, because one day you will. And the third thing was, would be, you know, be of service. Like, it's not about you. It's not about your fame or your presence or your money. It's literally the whole game is how can you help people. And if you always come from that place, you will always be successful.
Lindsay Pinchuk
Jessica Zweig, founder of Cheeky Chicago, Simply Be and Jessica Zweig Dot com. Right, right.
Jessica Zweig
Ding, ding. You know, and we're.
Lindsay Pinchuk
Yes, I'll take it back. Thank you so much for being here. I am, I am honored to have a front row seat to your journey. I am honored to be in your orbit. I cannot thank you enough for your support and just I, I know I can rely on you always and it means a lot and your friendship means the world to me. So thank you so much for that and for being here and sharing your story and being so forthcoming. I I love, love you.
Jessica Zweig
I love you to pieces. Lindsay. Thank you for having me back. This was such a treat.
Host: Jessica Zweig
Guest: Lindsay Pinchuk
Release Date: August 26, 2025
This special episode features a deeply honest and behind-the-scenes conversation about what it’s really like to sell your business as a female founder. Jessica Zweig, now a serial entrepreneur and bestselling author, sits down with Lindsay Pinchuk, founder of Dear FoundHER and an exited founder herself, to swap stories, lessons, and the emotional truth behind leaving the companies they created. The episode explores the parallels between their entrepreneurial journeys, the reality behind a “successful exit,” and how embracing the feminine can power and heal women-led businesses. Listeners gain both tactical advice and personal stories from women who have navigated scaling, selling, and letting go.
“We both started companies to help the life stage we were in, and now we’re helping women do what we’ve done, the way we did it.” (Lindsay, 16:18)
Timestamps:
“Everyone thinks this business is you and you’re not for sale.” (Advice from Amy Schuster, relayed by Jessica, 23:25)
“I had to fight for certain things… but I just knew that a strategic buyer for what I had built was better than a PE buyer.” (Jessica, 31:19)
Red Flags & Legal Advice
Preparing Your Business
Quote:
“I came out of the identity as a boss babe, which I am... But it’s not the whole story. We are so much more than what we do.” (Jessica, 44:42)
Advice to Her Younger Self:
Jessica and Lindsay are authentic, unfiltered, and supportive, mixing practical wisdom with heart. Their candor about the pain and power of selling a business stands out, and both champion vulnerability and feminine leadership in today’s entrepreneurial world.
This episode is a must-listen for any woman building, scaling, or considering an exit from her business. With raw honesty, actionable insight, and a deep commitment to community, Jessica and Lindsay model what it looks like to create, let go, and rise again—on your own terms.