Selling My $22M Company Didn’t Fix My Life…It Exposed Everything Wrong With It

23:35It's free to start, has preset templates, and an AI website builder to get your newsletter and website up and running so fast. If you want to give it a try, head to beehive.com slash HSR for 30 % off your first three months, but make sure you enter the code HSR30 at checkout. That's B-E-E-H-I-I-V.com slash HSR with code HSR30. Let's talk about the perfect employee for a second because I think this is going to be really relevant to every single person listening, whether they're a founder or they're actually an employee. It's a really interesting dichotomy because we as founders want to bring on people that are as obsessed as we are, right?

24:16But then the advice that we're giving the people who are employees is like, have a way to mitigate your risk. Have side hustles. When you think about hiring today, like what does that perfect employee look like? It's so hard because that was something we struggled with at Create and Cultivate. We are a business for ambitious women to start companies, and a lot of our employees left and started companies, which I actually think is a good thing. I was like, that means what we're doing is working. We've motivated people to the point where they feel they can go out on their own. A lot of times when I was hiring, what I would say is, what are your goals and ambitions?

24:47Is it to grow within this company? Is it to get experience for a few years in this company and then go somewhere else? What do you want? And obviously they give you the answer you want, which I want to be here forever. And I was like, no, no, no. Just be honest with me. Because if you're going to be here for two years and give me your all for two years and then go somewhere else, I'm fine with that. I just want to know. And I will support you. I will help you. I will write a letter of recommendation. And I think that honesty brings people into a place where they feel like they can actually talk to you about what they're building versus like, I'm going to lie to you so I get this job.

25:20And I think people do that a lot, right? Because they think it's going to be there forever. But that's not the reality of what most people are doing. And the idea of staying in a company for 10 plus years has kind of become irrelevant for a lot of people. And especially in the startup world, we know how hard it is. And people really do typically burn out in two to four years. But for me, what I find now for the perfect employee is someone who is going to come absorb, learn, but also be their own boss. Like I have gotten to the place now where I don't want to micromanage people. I did that for so long where I was like breathing down everyone's neck and I'm sure they hated me, but I was just so relentless.

25:57But I didn't let people maximize their full potential at the positions. And there was a few people I got to trust that ended up doing that towards the end. But now I really want to empower people to be a self-starter and bring ideas to the table and then execute on those ideas and then tell me if it worked and then tell me if it didn't work. I want that kind of fluidity within the company for a few different reasons. One is like, I'm older, right? I'm not going to be on the pulse of what's happening in the 20s, 30s market of like, what's cool, what's trending now. And I don't want to be chronically online.

26:28I was chronically online for a very long time. But these girls are. And so I'm like, talk to me about what's going on in your world. What's interesting? Who do you want to see speak? Who would be like, oh, my God, I can't believe this person's here and being part of it. So really tapping them as like the hive mind of like our company is really important. And I want them to feel collaborative and like they have a piece of the pie. I think now it's a little different because we are venture backed. There is a little bit more breathing room. When you're bootstrapped, you are every dollar counts. You are fighting to build a company that is profitable, lean, where everyone is overstretched, over indexed.

27:03And that's how you have to build in that environment, which is not healthy for anyone. Now it's like we have a bit of breathing room where we can build in a way that we want to. Let's go back a little bit to paint people a picture of the career. So 27-year-old Jacqueline starts Create and Cultivate, sells it at what age? I think I was 36 or 37. 36 or 37. You take off that period of time. Talk to me about what you do once you're ready to get back into things. I launched a fundraising masterclass. So I was doing a lot of consulting, coaching, things like that. And everyone, as you know, was like, I need angel investors.

27:38Where do I find angel investors? Or how do I raise money? What are these things? No one was having these conversations. And I was like, okay, there's a formula. Here's how it goes. Here's what you need to know. Here's the terminology. And it was like every call I was having. And I was like, I'm just going to create a course. So I go and create this course. And I basically like don't market it. I'm like, here guys, here it is if you want it. And it does like well, but I'm just like kind of over it. I'm like, you know, I'll sell it to a few people, whatever. I get a DM from this girl who I'd met at a create and cultivate event, Marina Middleton, who was like, hey, I saw you discounted your masterclass.

28:11Is it not selling well? And I was like, who the fuck is this? Like, get out of here, girl. But then I was like, she's not wrong. So I was like, hey, yeah, actually, like, I was like, I didn't have the engine of create and cultivate behind me, which I'm so used to having. And like, I also am like, not really wanting to be like salesy on the internet and whatever. And she's like, no, no, I do. This is what I do. I do courses. I can definitely help you. Have you ever thought about doing a mastermind? And I was like, no, not really. I was like, I feel like people who do masterminds are not successful or haven't done businesses.

28:41It feels kind of weird. And she's like, no, no, no. I think a mastermind would be amazing with you. We should do one together. And I was like, well, if I can get someone else who's a true entrepreneur, has credibility to do it with us, I'm down. And she's like, I'll run the whole thing, blah, blah, blah. So I call Allie Webb, the founder of Drybar, and I was like, do you want to do this thing with me? And she was like, yeah, let's do it. I love like coaching women and being part of it. So we launch it and Marina runs the entire business and is a beast. And I'm like loving it. I'm like, oh, this girl is like hungry, aggressive, knows what she's doing, is obviously super passionate about it.

29:15And like year one, we do a million dollars. Like it's super successful. I'm like, this is great. And I love it. I get to coach women. It's super fun. All of these things. Parallel path to that, I'm still on the board of Create and Cultivate. So I'm on the board meetings, but I've like definitely taken a step back. I go to the events, but like very loosely involved. The end of 2023, I get a call from the private equity firm, which is rare. I feel like they don't really want to talk to me. And we had just had a board meeting that was basically like, okay, we're good. We're funding through end of year.

29:45Everything's going well. We're all aligned. Great, great, great. And I love the CEO that's running the company. She's great, feeling good. And he basically is like, we've lost faith in the direction of the company, and we're going to go after a secondary sale early. And I was like, wait, what? I was like, we just had this board meeting. I'm so confused. So I'm caught off guard by this entire situation. And so immediately I'm like, okay, who can I, who can I call that would be a good home for this? So that's like my initial reaction is like, okay, let me think about all the strategics that were during COVID that were interested.

30:17Like now we're kind of like have money or back like doing things. And so he basically is like, you have 24 hours and then I'm going to start like making some decisions. And so I'm like reeling, I'm like, what is going on? so he makes the decision i was like i can help like let me try and figure this out like he's like why don't you roadshow and raise money and i was like well i don't want to go raise money on a company i haven't been involved with like i don't know how to speak about this i'm also not like running it and then he's like come back as ceo but they weren't going to pay me the salary i would need to come back so i was like this is feeling like you're kind of trying to make this my fault but it's not my fault and not my problem but i also care a lot about this and i don't want to ever see it go away.

30:55I call Marina and I was like, hi, this is what's happening. I don't know what's about to go down, but if there was a world in which we could buy this back, would you want to run it? Because I knew I wasn't going to go back to being like the day-to-day CEO of building this company. And she, without hesitation, was like, 100 % yes. What do we need to do? And I was like, I don't know. I don't even know if this is possible. I just wanted to have this conversation because what we're doing with Blueprint is working. It's great. We can obviously loop this into create and cultivate. It feels like a natural extension.

31:27And I don't know. I was like, I don't have answers. I don't know. I need to go back and start to see what's happening. So essentially at that point, I went back and was like, if we're going out for a secondary, I would love to throw my hat in the ring to buy the company back. At which point I obviously have to recuse myself from the board and I'm no longer involved in those conversations. I loop in Marina. We start to have these negotiations. They are contentious to say the least and really difficult. because there's a lot of complications now that the company has had debt put on it. It's been acquired.

31:55It's now there's employees. It's like a mess, basically. And we just fought through as much as we could to get this deal done. And it really came down not to the PE firm, but the lender on the business who would be the highest debtor had this not gone through, where they basically said, like, we see if we get this back to you, it's our best chance of getting our money back, essentially. And so we were able to acquire the assets back and you essentially start from zero. So all of the employees are gone, which is really disheartening and very difficult to navigate. Everything's gone. They're like, here's just like the assets.

32:31Good luck. So you're starting from zero. And so we immediately went out and raised from angels because we're like, obviously, this is a very well-known company that requires capital. And then we took like four months to be like, what do we want this to look like? How do we rebuild this? Where do we start? and we put together this strategy. And I had this conversation with Marina where I said, there's two options here. Option one, you and I build this. We take this as our engine for our personal brand. We launch a podcast. We run the blueprint. We do a couple events a year, small. We have maybe two employees.

33:02And we start to build this as a smaller business, but that is for us and we can run. And we have a life. You hang with your son. We have a good life. like, you know, it's very mellow. I was like, option two is we pour fire on this thing. We go big and we sell it for a ton of money. I was like, you have less time with your son. You've never been more stressed in your life. I was like, your marriage, like you're not here. I'm like giving her this dark picture. She's like that one. And I was like, are you sure? She's like, I am 100 % sure. And I was like, okay. I was like, I'll support you either way.

33:35And we went out for venture closed our round very quickly. We're very lucky. And$2.4 million later, we were like, all right, we're building a huge festival. And we did. Why did you not want to go back as CEO? Those years by myself, I very much learned that I am definitely a victim of circumstance. If I'm put into a situation where I can put pedal to the metal and make it happen, I will be obsessive and I will go crazy and I will lose myself because I love building. It's such a deep fire. One of my employees one time was like, what's an adjective you should describe, Jacqueline? And she was like, relentless.

34:15And I actually felt like it was so true. I was like, I am relentless when it comes to those things. And I didn't want to be like that. I'm not in that stage of life anymore where I need to be. And I also want to see someone else feel that and be excited about it and be passionate about it. And it's so hard to find someone like that. So finding Marina was lightning in a bottle on top of this whole thing happening. You want this maybe more than I do. You're hungry, you're smart, you're scrappy. You love this community because you were part of this community. And it felt like the right move where I knew I was like, I don't want anyone to report to me.

34:48I want to be able to, at the drop of a dime, take a trip, do yoga, whatever. I can't live that life anymore because it physically is not good for me. And it was like that with Create and Cultivate. And it was also like that with Cherub. Do you think that some people can metabolize that stress differently? Like for Marina, it's a completely different experience being CEO than it is for you. Totally. And I think a lot has changed since when I was building. Like, you know, I was really coming out of that hustle world mentality. It was like sleep under your desk. That's how you prove yourself. Like that was what I was raised on and worked in.

35:23And then like somewhere around the five to six year mark of building Create and Cultivate, There was that massive shift around work-life balance and people not wanting that kind of relentless, intense boss. And I had to unlearn a lot of that where I was like, oh, this is what I've been taught works and this is what I've seen work. And now I need to find a happy medium between being this very emotionally regulated, balanced life. Like not everyone's going to operate at your intensity. And like we require this intensity to be successful. and finding that middle ground was really important. But I also think we've put in checks and balances to make sure that this time around, we aren't running everyone into the ground.

36:04We aren't doing an obscene amount of events. And I also think that comes with not being bootstrapped. That lifestyle that I had put myself into, and one of my big regrets was not raising money that first round, that first time around. It's so interesting that you're saying that because I think we hear the opposite so often. Do not raise money for your business unless you have to. You have golden handcuffs now to a totally different group of people. You have investors that you have to report to. I would love for you to expand on why you regret not raising venture capital money. I'm glad I didn't do it early.

36:36I would have done it later where I would have had all the control and all the power because we had such a good business. We were 4 million EBITDA growing, doubling year over year, on track to do 25 million, grossly profitable, multiple. I mean, we had product lines in Target. We had our podcast, we had our book, we had a million deals in the pipeline. And so when you're raising, when it's like that, you have a lot of control. So we could have taken on really strategic capital with very little, giving up very little ownership. And that would have changed my life because I was operating so lean and doing so much that I think I would have been able to elevate into a better CEO, a better boss, and build a bigger company longer term.

37:17But at the time, no one was really investing in companies like Create and Cultivate. Like anytime I would meet an investor like, oh, that's so cute that you're building a women's community. It's not how it was today where people are like, oh, wait, that's a huge business. I mean, Hot, Smart, Rich, huge business. Like these are things that can be massive. And we're seeing now that shift where creators now are just getting invested in for being themselves and developing new things. Like that was not the market. It was like, are you a tech platform? Otherwise, we're not interested. And I would say like that was why it was so important for me to sell was because I wanted to show that these businesses are real businesses and they have an immense value and can grow into these monstrosities, media companies, massive.

38:01I wanted to build the Disney for ambitious women. That was my goal and it always was. And I think not raising capital stifled that in a way and again, made my life much harder. You're such a transparent person as it comes to numbers. Like you just said, like 4 million EBITDA, 22 million of revenue. You sold your house for in the New York Post, it was like$4 million. You are very transparent around numbers. Was that learned or that's just because where did that come from? So I feel like women are doing a disservice to themselves to not talk about money. I was someone who really had to learn this stuff on the fly.

38:39I had a business partner in Create and Cultivate. Her name's Rena Panchansky. She started DBA, which was one of the first talent agencies for influencers, highly networked, really successful. And I was very lucky that she was able to really walk me through money, whether it was through the business or personal wealth. Everything from leverage. Leverage is a term that women just don't use. Once you have money, you never spend your money. You just leverage your money to spend other people's money. And that was something that you don't get taught. And so really being able to speak to women who had done it, built it, grown it, sold it, and then made exponentially more money down the line, you have to talk about that because otherwise we're all just stagnation.

39:24We're not doing ourselves any favors. And then talk about this stuff all the time. So for me, I wanted to be as honest as possible because I felt very lucky having met Raina that I got in the room. There's no reason I should be in the rooms I'm in based on how I grew up and who I was. I was, again, relentless in getting in those rooms. And now that I've been in them, my goal is to share as much information and value I can with other women because there are formulas. There are secrets to success. And we're not sharing them because we're so nervous that there's not enough space for everyone, which I understand why.

40:00Historically, that has been the case. But I actually think the more women who have money, the more powerful we become. Women historically invest back into women. For myself, I invest in female founders. I hire female florists, caterers, production companies, whatever it is for the events that we do. We invest back in our own economy. It's proven. So why would I try to stagnate another woman from making money that I know is just going to have more women rise? I love that. I think that's why we've gotten along so well, because we're very cut from the same cloth. Over 50 % of people in this month will make a resolution about better money habits.

40:36Peeling it back to like 25-year-old Jacqueline who hasn't hit liquidity yet and doesn't know about leverage and doesn't have anything to leverage, what are some of the money rules that anyone listening can apply for personal finance to be able to make investments, whether it's in their business or in their schooling or education? What are those basic rules that you still live by today? Yeah, I joke because I grew up in a very nervous about money household. Obviously, they own their own business, my parents. And I joke that I grew up in a mini bar household where I was terrified to open the mini bar and hotel.

41:12My mom was like, do not touch it. Don't get an M &M from it because I was like, that is going to make us bankrupt. I cannot do that. I always had that mentality around money, being very nervous and making sure I always had enough to be okay on my own. That was something that my mom really instilled in my sister and us was like, do not rely on a man. Do not rely on anyone else. You need your own money. I was very, very ingrained in that mentality going into it. My first few jobs, I was very lucky in that like my first job was at a place called Attention PR. Now I'm going to age myself in that they were a word of mouth marketing agency because the word social media did not exist.

41:49Wow. And, and we were like, Instagram had kind of just launched, but we were creating Facebook pages for like Estee Lauder. Like it was so laughable now, but at the time, highly innovative. And I was employee number three. So I was along the two co-founders who were brilliant salesmen, really smart. And I got a bird's eye view into how to run an agency from the ground up and sell to massive Fortune 500 companies. And I was really early to that social media world. I then was able to get poached and go to another job, doubling my salary, which was life-changing at that age. I was like 21 years old.

42:25From there, I was able to grow and bounce and make more money while I was doing that. I also had a blog at the time that was highly successful and was getting brand deals early days. And so essentially for me, I was always putting money away. I was always saving and really trying to spend as little as possible, except for on the things that really mattered to me. And for me, that was like having an apartment like that was livable in New York City and being able to travel. But really, I was just saving money for the longest time and really investing back into my 401k and all those different things.

42:57When I left the working world and I went to start No Subject, one of the things that's interesting about running your own company is that you can really run your life through that business. I mean, that's why they call it a lifestyle business. Your car can be through that company. Your rent, if you're working from home, could be that company. So figuring out how to really maximize that LLC potential was a good way for me to build wealth because all of this was through my company. And as the famous thing, it's a write-off. But it really was a good way for me to build that money over time. But the reality is, we live in this world where everyone's flexing private jets and this and that and whatever.

43:37And you can get caught up in that. And I think it's just important to be really honest with yourself about what you want your life to be. Do you want to live paycheck to paycheck? Do you want to always rent? That's okay if you do. But you have to have a really honest conversation about what you want your life to look like and what makes you feel financially secure. It's so interesting, too, because I think that women and men treat money so differently. Well, I will never forget this, but one of the first female fundraisers at Harvard's Endowment Fund, where they're calling alumni and getting them to invest into Harvard's Endowment Fund.

44:08She was the one that told me this, where she was like, it's so interesting. I'm now 65 years old. I went to Harvard, worked on the Goldman Sachs trading floor, and just seeing the difference between the way that women treat money and men treat money has not changed. Like in this 45 years since I've been in the workforce and she said it was because women think about money in such a finite way. And if you spend, it's like, it's gone. Whereas men think about money in such an infinite way. And if you spend, it's gonna come back to you. Now that you're on the other side of being an angel investor, running a business that is encouraging women to angel invest, have raised money yourself, what are the differences between men and women and how they treat money based on that like risk reward profile?

44:54I couldn't agree with you more. It's so true. And even being on the VC side, when I was getting pitches, men would pitch in such a grandiose fashion. We're going to be 300 million in the next two years. Like we're going to be doing this. Like this company is going to be the biggest thing you've ever seen. Women pitch in realistic goals. Like I will definitely hit a million dollars next year. And I think we'll be, you know, the really steady growth. And I'm going to be such a good steward of your capital. And they are because that's how women think. But we need to think bigger and we need to take bigger swings.

45:24It's like the BDE that everyone talks about. It's so real. Even with Cherub, as we're raising money, I'll send emails that are so something I would not say, but it's just like, are you in you out? Like we're the fastest growing company. Like, and the reaction I get is so positive, you know, because that's what people, especially investors want to see. Whereas women want to hit the goal. Men want to make you think they're going to exceed the goal. And then they always like under deliver for the most part. But like they sell the story, right? They sell the vision. They sell the dream. Whereas we are like, we want to be as practical as possible.

45:57And it's interesting because I feel like I agree when you're raising money. It's like the bigger vision. And I love raising money. Like I love fundraising. And I also then I'm like, but I have to be able to empower and educate and like make sure that the music isn't just going to stop, right? Like we're in this bubble right now, probably with AI, where it's like the amount of money that is getting funneled in there reminds us of like the dot-com bubble, right? Where it's like there will be one to two, three companies that will succeed. Everything else could potentially have really hard ripple effects for where we live and play in.

46:30So I feel like women, it's that double-edged sword, right? Where it's like you want to swing big. And even for myself, when I'm raising money, it's like I don't want to oversell what this could be because oftentimes it's like it works for a few rounds and then the music dies, right? When you think about people that are raising now, people that you're giving money to, like what are tangible takeaways that people listening to this can put into their toolbox when they're raising money from VCs to strike that balance between this isn't a fairy tale, this is real, but it's also big and grandiose and going to get me what I need to move society forward?

47:09I think for me, from an investment philosophy, I invest in things I know about. I think that's a good way to start, especially if you're starting out as an angel investor, because someone can tell me that this AI robotics company is going to be the biggest thing ever. And I have no idea. I'm like, LMM, whatever. What are we talking about? I am not the expert on that. So whatever you're telling me, I'll believe because I'm not involved in that industry. whereas beauty, fashion, community building, all of these things I know and love. So when you're talking to me, I know the reality of the situation and I also can be helpful to your business.

47:43And I'd rather invest in those companies where I understand the potentiality and the possibility versus something I do not understand at all. And I've invested in a few things I do not understand at all. And most of them have failed, to be honest. And I'm not connected to the founder in any real meaningful way. And so for me, I like to invest in things I've tried and tested. and I know will be successful, especially because I know how to help them. 2026 is the year we get hot, smart, and rich. But there is such a thing as being too hot. And that's what happens when you run as hot as I do when you sleep at night.

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49:30We're sent off. If someone wants to diversify their portfolio this year and has a resolution about money, when do they know if private market investing, angel investing is right for them? Right. So there is accreditation around this, right? And this is really a safety net from the government to say like, this is very, very risky. Do not bet your life savings on angel investing, which I agree with. However, I do think the most common misconception with angel investing is that you have to invest a lot of money. I was at a dinner recently with Bullet Pitch and my friend Felix, and I was talking to some of the creators there, and they're like, so how much do we have to invest?

50:06Like$500 ,000? I was like, oh, no, no, no, no. You can invest $10 ,000. You can invest$25 ,000. You can invest$500 ,000. But it really is dependent on what you want to build as a personal portfolio. And I think that's how you have to think about angel investing is every year you put aside a sum of money. Maybe it's$5 ,000,$10 ,000,$100 ,000, whatever that looks like for you. And you can divvy up where that goes into different companies. There's obviously things like SPVs where you can invest a much lower amount of money, lower risk. I think for early angel investors, they're a great opportunity to kind of get your feet wet.

50:38And then you can diversify and say, I want to invest in one CPG business, one food and bed business, and one AI business. And I get to determine what that portfolio looks like. And angel investing is a long game. It is not typically an overnight success story, even though lately we've been seeing some of those. I do think you have to understand that you're in this for the long run. But the other thing I like about angel investing and the reason I started angel investing was social capital. The reason I started investing in female-founded companies was I wanted those relationships with those women.

51:07I obviously believed in them and their businesses. But as I was building Create and Cultivate, those relationships were extremely helpful for me. Whether they were speaking on the stage or introducing me to other women in their network, it created a social capital ripple effect that helped me build my business. And then from that launch a fund because I had a track record. So I think for women, think of it as a small thing that you can step into and grow over time. But also it's important to realize one of your investments will pay for your entire portfolio. That is the goal, right? That will cover all of the cost of all the things that you've invested in over time.

51:40Or maybe you get multiple, which is great, but that's typically not the reality of the situation, which is why I say invest in things you know so that you can be helpful to that business down the line. For women that are listening to this or men and they're thinking about angel investing, what is the through line looking back on your years of investing of what to look for that can spot winners? I'm big on founders because I know really when you were investing, if someone invested in Crate and Cultivate when I was running it, I was going to be the one that was going to drive that to the finish line.

52:08Without me being obsessive about it, it wasn't going to last. So I think one is founder first. I mean, most of my investments early days are friends with like Diana Cohen from Crown Affair. Like we knew each other when she was working at Away, like back in the day. And so when we had kind of grown into each other and understood like our professional lives, when she said she was launching something, that was a no brainer to me. Deepika Kamutyalah, Live Tinted, like invested in her almost immediately. One, because of the community she had built, I knew how to kind of help her with that if need be.

52:36And also obviously it was such an underserved market. Another example now further down the line, intro. I'm an investor in intro because I was on the platform early. I've used it. I've had success with it. I've met so many incredible people through the platform. I believe in it. I love the founder and therefore would want to write a check into that as well. And the goal is obviously to sell, but now for me, it's more to support, I think is really the mission with what I'm doing on the angel investing side. And you can have those different eras of angel investing, obviously for returns, for social capital, and then to support.

53:06What is the smallest check you've ever written and the biggest check you've ever written? Smallest check I've ever written$2 ,500, like pretty small into an SPV and then$150 ,000. Okay. I'll be transparent with you too. My smallest was$2 ,500. My biggest is 50 ,000. And I feel like that is, I'm like, what creator is investing$500 ,000 into a business, Jacqueline? Girl, they are making money. But I think that's also a huge misconception about creators. Like not every single creator is making that type of money. Totally. Yes. But some of them are. And they have a ton of money that they're sitting on, and they don't know how to diversify and invest beyond putting in a high-yield savings account or just giving it to a wealth manager.

53:45So I always tell people that want to get into angel investing, because I actually started by obviously investing other people's money, but I also started doing equity deals for my advisory services. And I actually had an exit two weeks ago from an equity advisory relationship. And I would be so interested hearing from you now who's run multiple businesses, like if someone's listening and really, really, really wants to advise, create and cultivate for equity, let's just say that you're doing that. What is going to catch your attention to give up the most finite resource of your business to have them take equity, provide services for the people that are listening that just don't have the capital to start investing this year?

54:25It's my number one piece of advice I give people who are starting to raise who don't have a lot of credibility in the space yet. get an advisory board. It's so, so, so important and can absolutely game change your business early days. I think for us or like for me, I'm like a few different things. One is like, is this going to help my business grow? Whether it's through raising money, revenue, et cetera. Two, do they have information that I need? Like how have they done what I need to do before? Or three, do they have connections I want access to? Can they introduce me to people? One of the mistakes though is like saying, oh, I want an advisor and here's equity.

54:58You really have to lay out the terms. Like my advisory contracts are intense, you know, a lot of them because they're giving me a lot of equity. It's like, you know, weekly phone calls, introductions to VCs, you know, inclusion and crinkle day, whatever it is. And those things can really game change your entire business. But I'm huge on advisory shares. And I also think oftentimes, if you're investing capital, I always now pretty much do capital and advisory as one. So people have to invest into your company for you to then also give advisory. 100 % I would say we don't have any advisors for create and cultivate currently but like I would say that's important because you need them financially vested as well I was saying for me I also now am investing and also getting advisory shares totally I think back to like me though even five years ago when like I just didn't have the capital right like I really didn't have extra money to be putting away into these companies that are very high risk but also very high return and you don't see that money for five to 10 years.

55:55Totally. It's actually very crazy. Like a LP of mine and an SPV asked to pull out their money the other week. And I was like, I'm not sure if you know, but like you cannot pull out this money. And I think that's really important for people to listen to. But I think that there is value for people that want to get involved in this for all of the reasons we've talked about social capital, expanding your network, understanding how to actually build businesses and maybe spaces that you're really interested in. And I do think there is a world for those people that don't have the capital. It's about like shots on goal.

56:26And it's like that with everything. Like you might not get a yes from Jacqueline Johnson at Create and Cultivate because they need someone to put in capital to be able to get advisory shares. But there will be companies that are happy to take your advising without needing capital there and just start there. Totally. And I actually advise a lot of people to give advisory shares to VPs at companies that they want to be like. So for instance, a lot of my friends that are VPs at Summer Fridays or whatever, those are people you want on your cap table. They're helping them build these massive companies.

56:57You're not maybe going to get Lauren or whatever, but you can get these people who also have that credibility and that inside knowledge to help build your company. And it's a great way for people in corporate to expand their own diversity in terms of investing as well. Okay. So you have three pinned photos on your Instagram. One, we've talked about buying your company back after a$22 million sale. Two, we've talked about building the riot of angel investing. But you recently have pinned a video about your recent breast cancer diagnosis. You were recently diagnosed with breast cancer this past year.

57:33What is the first thought that came to you when you got your diagnosis? I was completely shocked. I did not expect this. Basically, I had gone in for my annual mammogram. It was really interesting. I had moved from Los Angeles to New York, had to restart my whole medical tribe of people I had to put together. My doctor in Los Angeles was like, you need to go get a mammogram. I moved. It was kind of like pinging me every month, like, you got to go do this. So when I went to do it, it was like, no, you actually need to get prescribed this in New York now. So I had to go find another doctor. It was like all these different things that were kind of pushing off this mammogram.

58:08But I kept having an ache in my left breast. It was so weird for whatever reason. I was like, this is so weird. and it kept reminding me to do it. So I finally go, I get it done. I get my mammogram. I leave. Fine. I get an email back that's like, we found calcifications. And so we need you to come back for another mammogram. I had no lump. I had no nothing, no history in my family. And so I'm like, oh, this is, so I obviously like Google it and try to find more information. And basically it's like, oh, this happens with age. So it's like, okay, no big deal. I go back in for that mammogram. The woman's like, do you know what's going to happen?

58:41And I was like, no. And she was like, we're going to basically see if these calcifications are staying apart when we do the mammogram or if they're coming together. If they're coming together, that's a problem and you'll need to get a biopsy. If they're staying apart though, then that's fine. It's benign. I go in, I'm sitting in the waiting room, hours go by. And I'm like, did they forget about me? Like what's going on? So I go to the front. I was like, I just like wanted to check in. They're like, oh no, no, you're fine. Just stay here. And they bring me back into a room and they were like, they're coming together.

59:08So you do need to go get a biopsy. And I was like, okay. But in my head, But again, I'm like, precancerous, whatever. There's no lump. So I'm fine. I go back in for this biopsy. The biopsy is very intense. They essentially vacuum out all the cells from this area. And they put in a little microchip so that if you do need to get surgery, they know where to go. In that meeting with the doctor, she was like, OK, here's what's going to happen. We're going to take these cells. We're going to test them. It's either going to come back as benign or stage zero cancer. and that was the first time I had heard that this is possibly cancer and so I was like okay and she was like I really don't think it's that so I felt good I was like okay she doesn't think it's that I'm fine no big deal I'm in Arizona on a work trip for this Zillow dinner we're doing it with creating cold weights I'm like all by myself in Arizona and they said my results would be up in a week and it had been eight days so I'm calling the like portal company I'm like hey I'm just checking in I'm trying to figure this out and they're like your results are up there do you not see them?

1:00:06I'm like, I don't see them. I'm like refreshing. And I get a call and I assume it's from the portal company being like, oh, this is what it is. And she's like, hi, this is Dr. blah, blah, blah. She's like, are you sitting down? And I was like, yes. And I knew. And she was like, I need you to write everything I'm about to say down. She's like, you've stage zero cancer, DCIS, all of these words I don't know. I'm writing them down. I'm like panicking. I get off the phone. I call my sister immediately. And she's like, okay, okay, we've got this, we've got this. And we're like researching online. And DCIS is really interesting.

1:00:42It's kind of best case, worst case, right? It's the best case of the worst case in the sense that you have cancer, but it hasn't spread yet. And stage one is when it spreads, stage two is when it's gone to your lymph nodes, you know, so on and so forth. So the protocol for this is the next step is you have to go to a specialist, right? And you start to really understand all the nuances of what goes into breast cancer. The number one thing, do you have the genes, the BRCA gene? Now there's more genes they've discovered. So you have to get the genealogy test. Two, does this run in your family? And then three is like, how big is it?

1:01:17How invasive is it? Where is it? All of the different things. And a lot of the mammograms and the research I had done show that you actually don't know until you get the surgery. A lot of people who have been diagnosed with DCIS get the surgery and then they find out they have stage one or stage two. I immediately went in for an MRI, was very relieved to find out it had not spread beyond to my lymph nodes or anything like that. That was great news. I went to MSK, Memorial Sloan Kettering. I cannot say enough about them. They are at the forefront of research around breast cancer and specifically DCIS.

1:01:48I loved my surgeon who basically was like, we need to just get this out of you. That's full stop what we need to do and get the lumpectomy to determine what the next steps are. I say all this to say, I had just moved to New York City. I had just gotten in a new relationship. We had just moved in together. I'm in Arizona by myself. I have to go to a dinner after and interview Tricia Lee from Owning Manhattan and shake hands with everyone. And I was fully disassociating. Everything is running through your head. Like, am I going to die? Do I have to do chemo? What does this look like? I don't have anyone here.

1:02:22How do I tell my boyfriend this? Is he going to be okay? Like, what is his reaction going to be? All of these things that you're trying to just navigate. And I was like, really, really lucky. Obviously, my boyfriend was like, let's go. We've got this became like truly the foremost expert on breast cancer, listening to podcasts, like downloading research papers, like such an angel. And I felt really ready for what was going to come. Sadly, I know a lot of women who have breast cancer. So I can I was able to pick up the phone and call Grace Helbig, who had just gone through this a year earlier, you Daniel Fishel, who was on Dancing with the Stars at the time, texted me and was like, I had DCIS a year ago.

1:02:56Let's hop on a call. The community was so supportive, which is part of the reason why I wanted to post about it. Did it change your relationship with Money and Success at all? Yes. It's expensive to have breast cancer. I'm very fortunate to be in the position I am and obviously have the insurance I have. I can't imagine for anyone else going through this. It's beyond costly. I also felt very attached to this community. Like when everyone kind of started talking to me in that way, I also wanted to slow down. It also became this thing where health is wealth. It doesn't matter how much money you have in the bank.

1:03:30If you don't have your health, you don't have anything. And I really wanted to focus in on living my life, enjoying every single moment, taking the pressure off myself and the situations. I sometimes put a ton of pressure on myself and just understand how fragile life is. Life can change on a dime. I think even it's just about this year in the positive ways. I met my boyfriend who I absolutely love. I moved to New York City. I have been able to do a million different things because of the changes in my life that happened so quickly. And at the same time, they can also have that reverse effect as well.

1:04:05Your life can change overnight. And it's just so important to be on top of it as much as you can be. And I'm very on top of it, I think. And I was lucky that I was able to catch it so early. Did it change anything about your relationship with your body? Absolutely. I've been on a health journey the last three years. When I was growing Create and Cultivate, I was the most unhealthiest version of myself. I didn't have time to work out. I was exhausted. I was truly not eating well at all. I was on the road, as you know, traveling. It's a nightmare. I barely went to the doctor and I came out broken in a lot of ways.

1:04:40And I completely changed my lifestyle after selling the business, working out, eating healthy, whole foods, vitamins, testing, getting tests on every single thing, per nuvo, everything. I was on top of it, but the body keeps the score. And I definitely feel like the years I didn't pay attention to any of that stuff caught up with me in many ways. And so now I'm undoing a lot of that. But also, I think for me, I'm very cognizant of paying attention to my body. The pain in my left boob, this is so weird. It is not a symptom of breast cancer to have pain in your boob. It's just not. It was my body giving me a wake-up call to go get this mammogram.

1:05:17And it's interesting. Few other people, my partner, Cherub, also had breast cancer. She was like, I had aches in my boob too. And I think it's just intuition. You really have to be so aligned with your physical body to be able to notice those nuances because you're just powering through life. You won't notice it. It's such a great time to have this conversation because it's the time that everyone's thinking about tightening up their life, right? It's finances. It's their body. It's the way that they even think about their friendships, how they spend their time. Summing up your life story so far, like what is a piece of advice you have for someone listening to this that could save their life?

1:05:58You have to know your own boundaries. And I really, I mean that in this, like really in an intuitive sense, people would always say with me or say to me, like, you're in your flow. And I wouldn't know what they meant. And I was like, I really don't get that. I feel like I'm just doing what I'm doing. This is fine. When you get out of your flow, that's what you know what it means to be in your flow. And that's a very real thing. A good example of this is I was with a friend in LA and she was visiting and I was like, let's go to this coffee shop. We go to this coffee shop. She runs into an old friend who ends up connecting her to someone she ends up dating.

1:06:29She's like, oh my God, that's so funny. What a random thing that I ran into at this coffee shop and ended up being this person. We go to this bar after and she's like, I'm pretty sure this is the woman that owns this coffee shop that's going to carry my matcha brand. I'm going to walk up to her and introduce myself because she hasn't gone back to me. Walks up, introduced herself, now is carried in all their coffee shops. And I was like, you're exactly where you're meant to be right now. Like everything is working out for you. And I was feeling the opposite at that time. Nothing was working out for me.

1:06:55I felt everything I was doing was having the reverse effect. I wasn't feeling great. Anything I was trying to do wasn't like manifesting in the way I wanted to. And when I picked up and moved to New York, I got right back on my flow. Everything started to work out for me. It was completely different. And I'm sure that's partially mindset, but I think it's really important to pay attention to those nuances physically emotionally in life are things happening for you in the way you feel like they should be or are things not working out and what do you need to shift mentally physically location wise whatever to make that change happen for me I can relate to that like it was changing my environment like being in a new place changing my neuroplasticity like I will never forget this podcast episode of diary of ceo when it was this person talking about if you have the same morning routine, and you go on the same walk every single day, which I was doing before I ended my relationship.

1:07:48If you go to the same grocery store every single week at the same time, if you go to the same Pilates class, if you go to the same coffee shop, you are not increasing your neuroplasticity and you are not allowing for life to happen to you because you're in the same routine. And I remember it was like, if you can't pick up and move and go to New York, like go to a different grocery store, go on a different walk route, even if it means you're walking from where you usually end and that's where you start, like it is those simple, small things that can completely change your environment to a level that I don't think people really appreciate unless you've been on the other side of it.

1:08:22Nothing changes if nothing changes. And I think those are the truest words. You have to go to that event that you're kind of dreading and don't feel like going to. You have to raise your hand and ask that question at the panel you're attending. You have to take those risks and change it up to your point in micro ways, it'll change your life. How do you make sure you don't get back to that place that feels dark when things start to feel comfortable? Yeah, you have to keep pushing your limits. And I think for me, I do that in different ways. It's taking trips and traveling to places I've never been to and like really getting outside my comfort zone.

1:08:53I'm going to Morocco at the top of the year with my three girlfriends. Like we're gonna have this amazing time. I can't, we're camping in the middle of the desert. Like I need to feel alive and out of my day-to-day comfort zone. I would also say like I am getting more comfortable with riskier type investments. Like one of my goals this year is to LP in a fund and really like get into that side of that world because I've done all the other sides. Like this is something I really want to do. And being okay with everything falling apart. Like I think once everything falls apart for you, it becomes much easier to get used to that.

1:09:25Like once you know what it feels like for things to fail, failure doesn't feel so scary. And I think you have to take those big swings. but also for you and like where you're at, go where the momentum is. If work is taking off for you, your personal life is thriving, like lean in to that momentum. And when you feel like a little antsy, then fuck around and find out. But I think like there's also beauty in leaning into what's working and just feeling good in that moment. I am so happy that you came on for one of the first episodes of 2026, Jacqueline. I have some fun rapid fire to finish off, but thank you so much for coming on.

1:09:59Seriously, I had such a good time. Jacqueline Johnson, what is the last thing you put on your credit card? Last possible thing. It was a coffee at Soho House. Love. Okay. Last most expensive thing you put on your credit card. Oh my gosh. So I upgraded my ticket to Morocco. And this was so upsetting because I was about to do it before I went to dinner. I didn't. It was$3 ,500 for first class. And I was like, okay, I'll do that when I get back. $7 ,000 to upgrade to first class, which I was like, I really thought about it. I was like, okay, I need to really think this through. But then I was like, you know what?

1:10:27This back cannot first eight hours in economy. I was like, I got it. I got to do it. I got to do it. But I put that on my credit card. It's very upsetting. But here we are. I love that. Wine or therapy? Both. Depends. I think therapy maybe more over wine. It's going to give you more results. Favorite keynote speech ever at Create and Cultivate? That's such a tough one. But I think for me, Martha Stewart. Iconic. what year was that 2019 okay yeah you can only pick one for the rest of your life couch friends or travel friends travel friends what is your favorite female founded brand that is not yours one kind i don't know if you know them clean skincare uh i'm an advisor i've known the team for a long time madison's awesome and their products are amazing okay love we have to check it out last one if you could title this season of your life what would it be called abundance I think I'm finally in an abundant mentality where I think I was living in a limiting one for a long time.

1:11:30How did you make the switch? I think I started to let go of the outcomes, like just living in the moment and really understanding like you can have whatever million dollars in your bank account, but you don't want that there when you die. Right. Like you have to live your life and spend in ways that will change other people's lives, change your own life, travel, take the trip, do the thing. and just live life to the fullest. I think I was definitely living in a, I need to hold onto this for as long as possible. And now I want to let go. I'm going to buy you the book Die With Zero. Have you read it?

1:12:02Yes, I have. Exactly. Yeah. But that's like the book that's going around, like all these female founder circles. I was talking to Amy Liu yesterday and I was like, what are you doing? And she's like, I'm reading the book Die With Zero. And I was like, literally, I just read that book. So little book to read, like it is all about experiences and giving back and being able to like contribute things, you know, like leave a legacy, not die with a legacy, you know? 100%, like I think it's so important. Again, up to your comfort level, but like it's so important because I think founders just are like always trying to have the most cash possible because you want to be the most successful in all these things.

1:12:35But really like there's so much you can get out of to your point that is going to come back to you in the long run. I love that. Jaclyn Johnson, thank you so much. Where can people find you? They can find me at Jaclyn R. Johnson on Instagram, createcultivate.com and investwithcherub.com. Thank you so much for coming on. Have the best time. Happy 2026. Happy 2026.