Transcript of How to Build Wealth by Founding Companies and Angel Investing with Jaclyn Johnson

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We've all heard of Boomerang employees, but have you heard of Boomerang founders? Hi, it's Tracy Dinenzio. I'm an entrepreneur and investor and I've been your Money Rehab guest host this week while Nicole is on maternity leave. If you've been tuning in, you heard my episode with Nicole, as well as a two-parter with Tim Farris, the opera of audio. Real, real I'm your host, Julie Wainwright, who was my direct competitor in my business. And now today, you're going to hear from my good friend, Jacquelyn Johnson, the founder of Create and Cultivate, who started her company, grew it, sold it, and then bought it back later. We're going to hear from Jacquelyn on why she became a Boomerang founder, and how she's created tons of wealth through both building businesses and and angel investing, and how you can do the same. We also talk about managing the personal side of being an ambitious woman, how we deal with rising money and beauty standards that seem to get higher and higher all the time, And at the end, we play a really fun game of Never Have I Ever. So without further ado, here's my conversation with Jacquelyn Johnson.

Jacquelyn Johnson, welcome to Money Rehab.

I'm so excited to be here.

I'm so excited to have you here. I want to talk about everything with you. But let's start with the company that made you famous and financially free, Create and Cultivate. Will you tell our audience, for anyone who has been living under a rock and doesn't know what Create and Cultivate is when you started it, what it does?

Yeah, it has evolved over time, but essentially, Create and Cultivate is the largest media and events company for ambitious women. We're most well known for our large-scale conferences which we host all across the country and hopefully world, where we bring together CEOs, content creators, and celebrities to talk about business.

Amazing. And I have heard you say... So we've known each other a long time from back when we were both in the trenches. And what I always remember is that when you were building Create and Cultivate, you said, I'm building it to sell it. You don't hear that all the time. A lot of founders say, I just love my business, but you said you were building it to sell it. Why?

I had sold my first company. So I had a company before Create and Cultivate. It was a marketing events and influencer agency. And again, when I started that company, I had no idea about selling companies. I had no idea that company would even be sellable. And so essentially, when an offer came through to acquire that business, it was a whole new world for me. I was trying to figure out what does this look like? What is the financial piece of it, what's due diligence? So I was basically a master class in selling a company and doing it on my own. And after I sold that company, I realized, Oh, this is how you make real money as a founder. Obviously, creating something that someone wants that's valuable to that person. So I got a taste for it. So when I was launching Create and Cultivate, which had already existed pre the acquisition of that company, I realized, wow, this is something that has real opportunity to sell. At the time, most women's media companies were about beauty, fashion, lifestyle, with a sprinkling of career, whereas we were all career. So we had this big opportunity, I thought, to create something that would be very much acquirable.

And around what What year was this that you started it? You had sold your last company.

Yes. Okay. So the timeline is crazy. So the first Create and Cultivate actually happened in 2011. So early, early days, but so small. Truly, I knew everyone that was there. It was maybe 25 women, and it grew organically year over year, I would say, as a new business vehicle for that marketing agency. I really didn't treat it like a business. It was really selfishly to meet cool women and throw cool events. But I would say the turning point was, I would say, 2015 for Create and Cultivate, where it got big enough that I brought on a partner into that company, invested my own capital into it, and was like, this is a serious thing. And then the other business was acquired in 2016, which, again, was another big year for Create and Cultivate. I stayed on I was bored with that company for a year after selling it and did both full-time, which I highly do not recommend. Very brutal. Yes. And so I did that, and then I went full-time at Create and Cultivate after that.

So what made you an ambitious woman?

I think circumstance, really. I had moved to Los Angeles from New York. I'd always worked in corporate, so it was like a corporate girly, and essentially got to LA and got laid off and didn't know anyone. I never knew this about you.

I can't even picture you being a corporate girl.

It's crazy. So I worked for Interactive Corporation. I see. I worked at City Search. I don't know if you remember City Search. Yes, I do. But yeah, so I worked for them, and then basically was laid off after three months. And it was really challenging for me for a number of different reasons. One, I I just moved to a city where I knew no one. Two, LA at the time, this is 2009, was entertainment, and entertainment really only.

It was like pre-tech, pre-urinal adventure capitalist.

Totally. There was really no industries. I obviously had no experience in entertainment coming from New York. Three was my identity was really wrapped up in being a successful career woman. So getting laid off was not part of the narrative I was trying to build. After that, I essentially was applying for jobs, not getting anywhere, and started freelancing for clients. And so built up that roster enough to bring on another employee, ended up getting office space, ended up launching an agency by happenstance.

Just as an aside, you mentioned you got laid off, which can be so painful. Have you ever been on the other side of that? Have you ever had to do a layoff?

Yes. We had to do a small amount of layoffs during COVID, which was awful. I actually was very proud about how many people we kept on being that we were in events business. But yeah, it was awful. But I haven't had to do that in any other circumstance. And I think COVID was a special one for sure. To Not ideal, though, obviously, for anyone.

No, but it's a reality. It's a reality, especially for venture-back companies.

Oh, yeah. We were bootstrapped. So it was, obviously, everything is felt 10 times more, I think, when you're bootstrapped.

So for Create and Cultivate, you through this big events business over time. Did you ever raise capital for it?

No. So I put in, initially, $50,000. My partner put in $250,000 as a loan to the company. We paid ourselves back, actually, within a year serve based on the profits and things like that. That's the only capital that was ever put into the business.

I hear founders ask a lot, struggle with how much to pay themselves. So founder or anyone who starts a business, even if it's a small business, how did you figure out what to pay yourself?

So I'm actually the worst person to ask about this because I paid myself the same salary for truly 10 years. I had the notion, and it's widely known, is the founder never pays themselves a lot. The high paid founder is usually a red flag, depending on what your revenue is, obviously. But for me, I basically... I think I went in at $100,000, and I stayed at $100,000 for truly 10 years. And so I was really just putting everything back into the business, I will say, until I brought a CFO COO on probably in 2018, and she was like, You're grossly underpaid. And she was like, We need to change this. You need to make more money. And so that's when things shifted.

You had already made some money prior to that, right? So were you able to afford to live the lifestyle you wanted even while you were making $100,000 a year?

Yeah. So I had a nice windfall from the first exit. So I used that money to actually buy my first house. So I had equity in the housing market, which was really great. And then I also had a really big windfall from an angel investment I made. Those two things were actually what really propelled me through the next few years. And then we did take distributions occasionally from the company as well.

Okay, so you were profitable, you're making money, and every now and then you'd be like, we're going to hand out some of this money to ourselves to the people who run the company. Exactly. Okay. And so what do you advise for young women starting businesses who maybe haven't had a prior windfall? How do you recommend that they navigate what to pay yourself versus put back in?

Yeah. No, it's such a good question. And now I always tell people, I'm like, you really have to prioritize your own personal wealth when building a company. Do you do that year one? Probably not. But year four, year five, you really need to start thinking through your own What's your personal exit strategy? What does the financial success look like for you? Because I think we often put ourselves on the back burner. So I would say it's typically a ratio of revenue, right? So there's a lot of things online you can read about this, et cetera. But the revenue you're making should be reflective of your salary. So if you're doing a million dollars year one, you can figure out what your salary is of that. 10 % is probably hefty, but maybe realistic for your situation. As you grow your revenue, you should be increasing your salary over time. And again, that doesn't have to necessarily a guaranteed salary. You can bonus yourself, you can create goals for yourself, you can do distributions. There's ways you can get creative when you own the company. Obviously, if you have investors, it's a little different. But I think it's about getting creative in that way.

Totally. Okay, I want to go back to, you said that you sold your first business and you made some money, and then you had an angel investment that also worked out well. How old were you when those things happened?

So great question. I would say I was 26, probably, when I sold the company. And the angel investment, I was probably 29.

So that's huge. You were a very young woman who was creating real wealth. Yeah. That's very unique, right? That doesn't happen all the time.

No, it was new to me, too. I didn't know anything about it. I didn't know about what checking or investing or anything like that as well. So it was a whole new world for me. I will say I've been very lucky in the housing market, and I've been really strategic with real estate, which has also paid off longer term.

You build, create, and cultivate to sell When you sold it, then you sold it. Tell us about what happened when you sold it and what's happened since you sold it.

We actually had two sell opportunities. In 2018, we had a few strategic buyers come to the table, which was early for us, I thought. I think we were $8 million in revenue, a team of eight people. I had no executive team. It was pretty scrappy and small, but growing fast. We went through a process in 2018. We had, I think, four LOIs that came through.

For people listening at home, that's a lot of LOIs. Yes, and they were big money. Loi is a letter of intent. It's a buyer of your company who's saying, I'm informally making you this offer, and as long as your numbers check out, when I do diligence, I'm going to buy the company for this amount.

It essentially means nothing, and that's important for this conversation. It literally means nothing. It's not binding. Because I was like, buy me the yacht.

We're buyers.

Let's go. Yeah, it was exciting. It was a very exciting time. We went through painful diligence with a public company that was interested in buying us, and it ended up falling in the end of the hour, which had nothing to do with us, but was very brutal. And I say that to say because I think a lot of people think selling a company is very easy. And it's like you find the person, you do the thing. It is so challenging. There are so many ups and downs. Majority of deals, I would say, fall through. I don't know if you agree with that.

Vast majority of deals fall through. In my business, we went through three separate sales processes. Each time we had what they call inbound, we had a buyer who came to us. And then it's incumbent upon you to go out and go to all the other buyers. Shopping around. I was like, Hey, are you all so interested? See if we can get higher bids. And we did that three times. The third time, it culminated in a sale. But the first two times, I was sleeping under my coffee table. Truly. The stress.

And I wish I had known that most deals fall through because I think I was so emotionally connected to this deal. It crushed me when it fell apart. Because especially when we had done nothing wrong, I was like, No, it's like the markets had shifted. And so that was devastating for me and really challenging. I literally picked out my office space, had told employees. It was bad, bad, but again, it was a very hard and expensive lesson. And then so cut to, I basically was like, back to the drawing board. We need to focus on building up the C-suite and really growing. Had a banner year, 2019, top of money, absolutely crushed at Q1. And then we all know COVID hit. And luckily, we actually had a good story coming out of COVID despite being bootstrapped and-Being an event business.

And being an event business.

And being an event business.

Let me jump in. It's mind-blowing.

No, it is mind-blowing. I I think I just... I thoroughly threw my entire body and mind into that experience. I think most entrepreneurs were one or the other. They either completely shut down, which is understandable, or they were fight or flight mode and just went insane. I was definitely the person that went insane and was just like, Ideas, move fast, go, go. So we moved very quickly. We pivoted to digital. We luckily had a membership in place that we were able to monetize quickly. We retained 90% of our sponsors, did minimal layoff. Groups. We were very lucky. We were able to pivot very quickly and took a revenue hit but actually maintained EBITDA, which was really exciting for us. It was a good story for potential buyers. Now, what had happened was all the strategic buyers that were interested, obviously had struggled during COVID or had lost a lot of money and were not in acquisition mode. But private equity was booming during that time. They were sitting on a ton of cash and were interested in buying companies that had done well during COVID. So we ended up doing a deal with private equity.

Okay, for people who don't know what private equity is, can you sum it up in a nutshell?

So essentially, the goal of private equity is to find companies that are highly profitable, high revenue, and have a lot of potential to grow to then do a secondary sale. So essentially, the goal of private equity is to come in, provide infrastructure and expertise as well as cash to basically pour fuel on the fire of an already existing company that's doing well, to then sell it for a higher price in 2-5 years. Yes. That's essentially the goal.

So when private equity works, it's amazing. You get all these smart new partners, they take a majority interest in your business, they help you grow it. And then you as the founder, you get some money, you keep some stock. And then in a few years, you guys sell it together again to another buyer, and you make even more money. And that's the good story of private equity. The bad story of private equity and the reputation that private equity gets when it doesn't work among founders is that a bunch of guys in suits come in and they start squeezing the margins of your business and taking the heart and soul out of it. And instead of making it more valuable, they make it less valuable because they don't understand the founder mindset and the growth mindset. And you can end up then with an asset that's less valuable. And so you do see in some circles of founders, an eye roll happen when you talk about private equity. And when you see that, it's because people have had that experience. Yeah.

And really similar to venture in a way, is they're basically I'm going to invest in 20 companies and hope one succeeds. That's their model. When they go into it, failure is not even failure for them. It's just another write off or write down. Whereas you, the founder, is like, This is my company, this is my baby. It's just a different mentality. And there's actually a really good episode of Freakonomics on private equity that you should list too, if you haven't yet. It talks a lot about the breakdown of what it's doing, why it's not great for some businesses, but great for other businesses. It's really interesting.

Okay, I'll check that out. Because ventures, they know nine of 10 businesses are going to fail. Exactly. They're gambling hard. Yes. Private equity is gambling a little less hard, but still hard, right? They can have-Agreed.

And also, venture is not as involved in your business, depending, obviously, but usually they're pretty hands-off or maybe a little bit involved on the board, whereas private equity is very much in your business.

Okay, so you sold to private equity?

Yes, sold to private equity. Okay. It was a really interesting time. It was end of 2020, 2021. Obviously, the world was recovering, trying to figure things out. At the time, obviously, we were making a hard push into digital and into membership. At the time, I was like, I'm not the right CEO to run a digital media business. I'm an experiential person. I obviously love community. That's where I really thrive. I also had run the business for 10 plus years. I was exhausted, I was tired. It was well known amongst the private equity firm and the team that I was going to step down as CEO when we found a replacement. We found a replacement who was amazing. She came in, she had that exact experience in the digital media world. And I took a step back for probably two years and was on the board, obviously retained a little equity, but really was not involved in the company, which is, as you know, it can be very bizarro. What did you do? It was really odd. It's so weird to do something for so long and then to wake up one day and not do it.

It's the strangest feeling in the world. But I Basically, I bought a house in Napa. I started gardening, I started cooking, I started getting my sommelier accreditation. I started just doing hobbies, I think what normal people do, working out, just enjoying life for a little bit. And then I got a little antsy, as you do. And so I ended up going to run a $20 million fund for a family office.

Wait, can you explain what that means? What's the family office?

Family offices are typically high net worth individuals or families that create their own essentially like little mini venture fund where they invest in different companies. Office, and oftentimes they're involved in their passion projects, things like that. People who want to create more wealth amongst their family, they'll create a family office. This family office was based out of Chicago, and they really wanted to get into the female founder space, which obviously is my Was it out of heart that they wanted to get into it, or did they have a theory that female-led companies were going to outperform? I think it was a combo of both. I think they typically had been in less sexy industries, insurance industry, blah, blah, blah, and technology done extremely well. But they wanted to tap into the consumer space a little bit more, learn more about it. For them, this was perfect for me, and so I was able to bring a lot of deal flow in. Also being on the venture side was really interesting. I learned a ton about diligence because they obviously had a best-in-class team that was doing all their diligence for all their projects, got to work with really incredible analysts and really understand what it takes to diligence a deal and what to look for and all those things.

That was really fun. So I did that for a little bit and then ended up launching the Blueprint, which is a mastermind with Ali Webb and Marina Middleton after much convincing from Marina because I was like, I don't know if I want to get back into coaching and events and things like that. And she basically convinced me to do it. And so that was what I was doing when things took a turn and changed. So end of last year, I'm doing the blueprint. Essentially, it comes to light that there's an interest in selling, creating, cultivate again. So this was way quicker than we had ever imagined. And it was a surprise, I think, to everyone on the team, on the board, et cetera. And so initially, my reaction was, okay, who can we sell this to? That makes sense. That's going to give it a good home. Obviously, I know a lot of amazing, centric media companies have a lot of relationships there. And also there was a lot of people interested in buying us. So that's where my brain went immediately. And then essentially, as things were happening, I went back to Marina, who was my partner on the blueprint, who is very young, very hungry, did an amazing job with the blueprint year one.

We were able to do seven figures year one. It was amazing. And I called her and I was like, this is what's happening. I want to throw this out to you. And this might be crazy, but what if we bought Create and Cultivate? She was like, in. I'm in it. Immediately, yes. And I was like, no, I need you to think about this because I don't want to go back and be the CEO. But I I know there's so much value there, and I think we could put our own spin on it, looking at what we've done with the blueprint. I feel like there's a major opportunity for smaller, more intimate events. And she was like, no, 100 % of me. At that point, I send this email out. Essentially, that's like, I'm interested in buying it back, which It sparked a lot of different emotions amongst the private equity firm, and then, of course, our lender, and then the existing CEO. And so honestly, over two months of just like, negotiations back and forth, it falling through, it coming back, all the things that happen when you're in the midst of an M&A What were the negotiations like?

Private equity never likes to sell back to the founder.

Really? I didn't know that. Why?

Because typically, I think it's considered a failure on their end. When you think about going back to the fact, it doesn't exactly make sense. I'm sure in some scenarios it might, but I think for them, it doesn't look good to their LPs. It can be perceived as the optics aren't great. Also, there was a want to sell it to a bigger media company and things like that, which obviously makes sense, too. I was supportive of the best possible outcome. I wasn't gunning to mess up any deals that they might have had, but I also was like, I do feel very strongly that I'm the best person to take this back because of a few different things. One, to your point, it's a community-centric business. Yes, on paper, There's a PnL, and there's a PnL and there's revenue and there's this. At the end of the day, there's people, and people related to that business, in part because of me and my journey in building it. And so I think it's really hard, whether it's a strategic acquisition or a private equity acquisition or any type of acquisition. It's very challenging when you're so connected to a brand that was built around you and your vision and your story to then sell it.

It's just hard. It's a hard business to then grow and build separate of that person. Totally. I think they didn't realize that, or maybe they thought, because we were going more digital, but then events came back, or is that going to go into it? Basically, through the negotiations, finally, it became clear that it would basically come back to me, which It was very exciting.

Wow. When you said, We should buy this business back, did it feel like something from your gut coming up and being like, Get me my baby.

Totally. It was weird because it was like, again, I had already started another company, Cherup, which we'll talk about. So I would... And Blueprint. And so I was like, this feels crazy, but it weirdly feels timely. I am a big believer in everything happens for a reason. And I think meeting Marina, launching the blueprint, all those things led that moment, because truly, if Marina was not in the equation, I wouldn't have done it.

Yeah. So she's the CEO now.

She's the CEO now. Yeah. So basically, it was this kismet reality that I think happened for the right reasons.

So, Jacquelyn, when you sold your business, can you tell us how much you sold it for? But not just that. Can you tell us how much of it you owned when it was sold?

Yeah. So basically, we exited for $22 million. That was the valuation that we exited at, which is amazing. I'm very proud of it. However, our valuation should have been much higher. But due to COVID, basically, they did a blended EBITDA for the years. So it was a little different in that way. Typically, I would say most event businesses would have exited based on a $4 million EBITDA in 2019 for 40 to $70 million, depending. Very happy with the way it ended. I owned a majority stake, but I can't tell you the full amount. But I owned a majority stake because obviously, we had no investors outside of myself and my partners.

Do you hear... That's Amazing. Congratulations. And it's interesting, because $22 million is a lot of money. But you often hear about exits that are for $200 million or $2 billion, but the founders don't make money.

Yeah, they're only 1% of the company.

So what's different about that versus what you did?

Yeah. So it's just a totally different strategy. So selling a business... Yes, I talk about this all the time, $22 million is like, I'm going to get the majority of that cash in that transaction because I own the majority because I didn't give up equity while raising money. Whereas founders, again, who are going to have these billion dollar exits need a lot of money to get to that mark in general. So they'll raise a lot of venture capital and therefore dilute themselves. So there's different ways to view equity, and there's different ways to build businesses, and there's different ways to exit businesses. I actually have a good friend who I think her exit was like 500 million, maybe 450 million, and we ended up making around the same amount of money. Is there any right or wrong way to do it? No, not necessarily. It really just depends on the type of business you want to build.

So my business was in a category that was very capital-intensive. All of the competitors were raising hundreds of millions of dollars. I raised $150 million, which meant $22 million would have been a failure. We had to sell for much more. But I also had a single-digit % ownership in my business by the time we sold. It's very, very different. So when you hear the headlines about how much someone sold a business for, is it really even related to how much the founder make?

No, it's not at all. And also it typically is you don't know if it's cash, you don't know if it's equity, you don't have to roll equity. There's earnouts as part of it. And mine had all three. It's interesting because a lot of people were like, Wow, congrats on making $22 million. And you're like, No, not really. And again, after taxes, it's even more. But I feel really happy with where I'm at. As I mentioned, the sale of Crane Coldvate was by far my biggest windfall and obviously has set me up for a life that I never thought I could have and is amazing. However, it was the decisions I made leading up to that that also has increased my networth over time. And that's the real estate, the angel investing, obviously bringing on a wealth advisor. All those things are making my money work for me. So it was not just, yes, I had a lot of eggs in that basket, but I also diversified along the way, which I think is important.

It's also really noteworthy. Your story is not uncommon. I know so many founders who made X from their business and then some random thing that they did on the side.

That is my story. I hope that continues to be my story. Yeah, I hope so, too.

When you bought back, created cultivate and cultivate from the private equity firm that had purchased it, how much did you buy it back for?

I can't tell you that.

Okay, you can't say.

I feel really good with where I'm at. I think financial security is so important to me. I think I've worked so hard for this moment in my life, and I do feel very fortunate. My life didn't change so drastically. My real estate changed, maybe the car I drove changed, the trips I take changed, but nothing was so overnight completely drastic for me that it feels really good.

Hold on to your wallet. Money Rehab will be right back. And now for some more Money Rehab.

I'm so excited for the next chapter of Create and Cultivate. What's going to be different in B2?

Our new philosophy is around launch to legacy. And I think the reality is we've been speaking to the launch side of the business for a very long time, which is starting a business growing a business. But we've never really done the full circle of, how do you exit a business? What's your legacy look like? What's leadership look like? It was really all about just getting it off the ground. So now we're taking this launch legacy approach, and we do that through a couple of different ways. One is through masterminds, where it's really that intimate one-on-one style training with experts, whether it's me or Ali Webb, et cetera. We also have retreats for seven, eight, nine-figure founders, where you're really in the room with people who are at your level, which I think for me, early days of create and cultivate, it was all about the speakers on the stage, right? And you're sitting in the audience and you're listening to amazing people, which is great. It's inspirational. It's awesome. What I didn't really factor in was all the women in the room, where with Blueprint, with our retreats, all the women in the room have a lot of value to add.

And so it really becomes this mind meld or what they say, mastermind of women coming together and giving advice. I learn from people in the room, which is awesome, like something that I never had experienced. So that's part of it as well. So all these intimate style, specific events. On the flip side, we're also launching what we're calling Coachella for Career Women, the largest festival for ambitious women next summer here in Los Angeles.

That sounds like so much fun. And so that's for all founders, early stage Are you thinking about getting something lunch? It's funny. I hadn't told you this, but I met a woman who has an amazing business, $20 million of revenue, and she told me that she's going to one of your events. And I think it makes sense. You've got the top of the funnel, which is everyone who's thinking about starting and trying to get it off the ground. And then it gets fewer and fewer of us as we move on. Until when you're at the point where you're a woman with a business doing 20 million or $100 million, it's a bit lonely.

It is. And it's totally different problems and issues than when you're starting out. And I think that's the thing that was really challenging. Being at the seven-figure founder retreat was really interesting where people were like, What's my exit plan? How do I find the right number two? What does this look like? And how do I grow my personal wealth? Those are the things you're worried about at that level. Where six-figure, you're like, How do I get to seven figures in revenue? How do I do this out on a ball on a budget? It's a totally different set of problems that require different solutions.

Yeah. I always tell women that your best mentors are one or two steps ahead of you. Because someone who's just sold their business can be really helpful to someone who's got a Series C or a very mature business, et cetera. Interestingly, so seven-figure problems are their own thing, eight-figure problems, nine-figure problems. Let's switch a little bit to personal life. Yeah. What are the... Again, same thing. We know that being a woman with financial freedom, a wealthy woman at a young age is mostly great. What are some of the things on the personal side that are difficult?

I think to your point, one is you get fewer and fewer. So people that can understand what you're going through as you're building become very small. I feel really lucky that I had a really great coach while I was growing the business. So important. I was like, I don't know about coach. I was a little on the fence, and I truly, thank goodness, because I think a lot of people tend to just talk to their therapist about business stuff. You need a coach.

You need both.

No, totally. You do need both. That's right.

No. I'm like, why? When I was running my company and it was really big. I was like, How am I spending three hours a week being helped? No. But really, in hindsight, it could have been more At a minimum.

But so many things go to the wayside when you're building your health, fitness, friendships. I missed weddings. You You miss a lot. There's things like that that you're definitely giving up along the way. Then I think it's really challenging. I was married for a long time. I'm now divorced. Obviously, I think being married was helpful while building my career. Then now being divorced and being successful, it's insane to date. It feels actually crazy because I think there's a lot of, not jealousy, but a lot of insecurity, I think is the right word. There's a lot of insecurity about successful women, even if the men that you're talking to have the best intentions and are like, I love women. I'm so excited for the Balance is really hard and tricky to navigate.

What do you think it is? Is it the masculine-feminine energy cycle gets disrupted?

I think there's also just hetero norms of wanting to pay for things. I think it gets really complicated around, specifically, vacations in real estate.

Oh, my God. It's so true. These are the two things. Vacations. It's really vacations. Because if you take a...

I want to take a nice vacation. Me, too. We spend on travel, right? This is something we spend on. And so as a partner, they can never surprise you with a trip because it's not going to be on the level. Then you feel bad because you're like, I don't want to make you spend on this type of thing because I know you can't. So that's when things get tricky. And same with real estate, where it's like you move in together, they can't possibly pay the mortgage or whatever. It becomes this challenging thing. And then you can be like, You do 20 %, I'll do this, and then it gets unsexy and not fun.

Were you in my relationship, Jacqueline? It's not cute. It's not cute. Wait, so do you have the answer?

You have to find the right partner, I think, who really either is on your level or is nowhere near... It's one or the other. I think that's right. Someone told me once, and I don't know if this is true, but they were like, You either need a date really young or really old, really rich or really poor. It was like, What or the other?

I love that because I think that's true. If you're, let's say, dating another founder who's a few steps behind you and their business is struggling and you're booming or you've already had a lot of success, it just introduces a lot of opportunity for weird tension that doesn't work in a romantic relationship. But if you date someone who's in a blue-collar job and they're just like, Check out my girl. She's so cool.

She's really rich and successful. Or just starting out in their career where the advice doesn't feel condescending. It feels exciting for them because they're just starting out. Whereas they're not on year five trying to make it work, and it becomes a whole thing. And again, I don't know if that's the answer. I still don't know. I've not found out what the secret sauce is.

Okay, but you just said you're solo, so you're single and you're dating.

Yes, trying. Okay.

Are you planning on going young or old, richer or poorer?

Gosh, I don't know. I'm trying to just get a date. I feel like I have taken a back seat lately. I was early days on the apps, doing the thing, trying it all. After your divorce. After the divorce. Yeah. You're trying to get back into it. And then you start to realize how much of your time it's taking up. And I just had this moment earlier this year where I was like, I just want to get off the apps or limit to one app and barely use it and engage here and there. But I also just want to live my life. And I know that's tough because I think truly one of the only ways to meet people is being on the app. That's just a reality, especially for me. I travel a lot, but I travel for work.

And you go to events for women. I run events for women.

Truly, even I think back, I'm like, I don't think I met a man in the last 10 years. Private equity was the only time I ever worked with men. I was like, never happens. But I don't go out a lot. If I do, it's like my close friends, we get dinner. I don't organically meet people that often. However, I feel like I've been challenging myself to, when I travel or I meet a friend for dinner, try to go a little early, try to sit at the bar, try to be more open to meeting people. This is my new... I think- Like IRL at the bar I'm at the bar. Just like, chopping it up. Can't even Google them? No, totally. I try to just be in the world a little bit more than I would be normally. But I'm trying not to do the app thing. I think it's just disappointing and really challenging I'm too time consuming. I don't want to be on my screen all day.

Would you ever do a matchmaker?

Yes. So I hired a matchmaker. I don't know, girl. I feel like it's also disappointing.

It's also really hard. Jacquelyn, I need... Listen, we're counting on you. I need you to figure this out.

Listen, if I have a success, you will hear about it, trust and believe. But yeah. I also don't think my person, and this is a broad statement, is in Los Angeles. So I think that's- Oh, that's interesting. Also hard, right?

Did you tell your matchmaker to cast Annette far-wide? Travel for love?

We'll travel for Love. So I don't know. We'll see.

I hope it works out. I'll give you updates. You have trailblazed so many things for women, for ambitious women. Hopefully, it's this as well. Can you please trailblaze this? We are counting on you. What about friendships? Have you been able to keep the same friendships over the years as your career has taken off?

Yeah. Actually, it's one of the things I'm most proud about is most of my friends are 10 years plus, have been in it since the beginning, have known me when I was struggling, have known me when I'm successful. We all don't live in the same place. We all find each other and travel and things like that. So I'm really proud of that. There's been friendships that have grown apart. Obviously, as time goes on, I think that's normal and natural. But yeah, I'm really proud of the friend group I have.

Do you feel like it's complicated to navigate the same types of things, like vacations, et cetera, with friends, or is it easier?

I think it's easier. I think it's just this weird inherent thing where it's sometimes I'll treat my friends. We all are just like, even Steven, life's going to work out. And I'm like, Yeah, one day you'll be rich. I think women just have that natural...

It It's so much easier. It's so different.

I know. It's so different.

I do know people who have weirdness with their friends, but I always think they're weird. I'm around my friends, then they're weird with money. I'm like, Why are we weird with money with your friends? There's no stakes at all.

No, no, no.

You can just buy me a piece of chicken.

Yeah, totally. The stakes are low, but I think that comes with longevity. I think newer friends, that's maybe a little trickier to navigate.

Hold on to your wallets. Money Rehab will be right back. And now for some more money rehab.

Okay, one more thing on the personal living life as a successful woman side. This might just be LA, but I don't think it is. I feel like it's spread everywhere I go now. Most of the women I know who are successful, myself included, are being sucked into a world of constant esthetic treatments that are expensive and time consuming and risky. But it's like the The bar keeps moving for what's-Yes. How do you deal with that?

It's really interesting. I've definitely been grappling with this a lot. I think with the dawn of the TikTok disclosures of all the things we're getting, all the work I'm getting done, all these things. Because I'm 39, I'm turning 40 next year. I'm definitely in that phase of, do I need to get all this stuff? There's this really funny TikTok of this girl who's basically like, lip tape, buckle fat. Oh, yeah. Like, mouth tape, buckle fat. She just starts naming all these things like, spray tan, pilates. I'm like, women are so fucked. The amount of stuff that we have to do to just exist in the world in the narrative is actually crazy. And I think for me, I've taken the approach of, one is I take care of myself in a way that makes me feel good, but I try not to buy into trends or fads. I'm also like such a baby. I'm so scared of everything. For the pain and everything. Yes. For the pain, for something going wrong. I don't have a lot of... I'm not a risky type person. I have friends who are like, Oh, Morpheus, whatever. I'll get that.

I'll get this. I'll get that. And they look amazing, and it goes So I'm like, Do I? But I think for me, I'm a little attached to the idea of aging gracefully and also just wanting to look different. I think a lot of women are just starting to look very similar.

It's wild, right? It's beautiful. It's like the same face. It does look good, but it's the same face.

It's the same face, and I miss little quirks, that people character. I'm holding on to that. Now, that being said, talk to me in 10 years.

Totally, because it gets real.

I might be getting a facelift and I will report back.

I always felt I felt when I had my company and I had a lot of women in my community, customers and employees, I felt like this obligation to resist the pull to all of that stuff. But then I would go on TV to promote the business and be like, Oh, I don't look good next to all these people who've had all this stuff done. And so it's really tricky.

I definitely get down on myself. I definitely look at photos. I try to also remind myself, you're a human being. This is what you look. I don't know. It's tough. I'm the same way. I'm guilty of looking at photos and being like, Oh, please don't post that. Or, I I hate this. I filmed something the other day and I got my arm fat in the back. I was like, Oh, my God. So we're so hard on ourselves. We're the hardest. And I think for me, it's really just about being as healthy as possible. I feel really good right now because I feel really healthy. I work out, I eat well, I have fun, I drink, whatever I have a good time. I'm not limiting myself into a place where I'm just constant deprivation. I want to live a full fun life. I love food. I love going out. I think it's finding that balance for yourself and feeling good and being who you are.

Yeah. And I hope more women start to resist the pull so that there are more examples of people who are just aging a little bit. That said, we're all striking the balance. Okay, you mentioned that in between selling Create and Cultivate and buying it back, you were working for a family office. You started investing. You got to be on the venture side. Tell me a little bit about creating wealth through... Tell me about angel investing. What is angel investing?

Totally. So angel investing is really when you invest in the private sector, right? So And you personally as an individual, or maybe you have a little family office or whatever it is. And angel investing, I think people are like, Oh, I need to invest hundreds of thousands of dollars. It's not the reality. Typically, you can invest 5K, 10K, 15K. And if it's an SPV, or a special purpose vehicle, sometimes you can invest as low as $1,000.

Or on platforms, various platforms.

Yeah, exactly. So I actually launched a company, and I'll tell you the origin story, but it's called Cherib. It connects angel investors and entrepreneurs using dating app mechanics. As an entrepreneur, you can go on, build your beautiful data room, tell your story, obviously put what you're looking for in angel investors, your check size, all that good stuff. On the angel investor side, you can join and talk about what are your mandates, what you're looking for, your personal expertise, and what you can be helpful with when it comes to supporting a founder, and then we'll match you based on that criteria. Since we've launched, over $2 million has been deployed to founders from chair of angel investors, which is amazing. I started angel investing in 2011, maybe a little earlier. So writing my first checks into different female-founded companies, and since I've grown my portfolio to 25 companies. So one of the companies that I invested in was a $10,000 check that early, early, friends and family round. And that company ended up becoming a unicorn, which, again, not normal. One in a billion chance.

So what was it valued at when you invested?

So I want to say the valuation was 10 million, something around that. And so basically, the company actually didn't exit. I got a tender offer from investors.

To buy your stock from you, even though there wasn't like a sale of the business.

Exactly. So sometimes when companies are prepping for IPO, they'll do a tender offer where they'll be like, We're going to give you a good price for your shares because they think they're going to get more, but it dilutes your risk. This was 2019 when that happened, and I ended up exiting for seven figures, which was amazing. I know. Jacquelyn. Super exciting. So that bought my second house in terms of the real estate. But I remember everyone being like, Crain Cultivate must be doing so well. And I was like, no. I mean, yes, but this is actually from an angel investment. But no liquidity yet. Yeah. So it was funny because I've had a few different exits now, not at that level. Thank God, not thank goodness. Please bring it on. But not at that level. But it's been really fun and really rewarding. And the way this happened was I am a well-known angel investor, so I get pitched all the time for investment. But I also do a lot of mentoring. I'm on intro and things like that. And all these founders are like, I need angel investors. Where are the angel investors? And I'm like, LinkedIn?

I don't know. I know people, but it's this insular world. But the And the bet that we're taking at Chareb is that there's actually a lot of angel investors out there that would invest. They just aren't getting deal flow. And so my co founder, Angeline, was that person. She works at a YC back company that was acquired by a larger company and then went public three months later. She had a great wind all did really well for herself, and was like, I would love to angel invest, but no one comes to me. So there was problems on both sides. We're like, Let's create something to solve this. So the way we're thinking about Chareb is the way I think Coinbase thought about crypto. Crypto, previous to Coinbase, really hard find, really difficult to buy, hard to know what's right or what's good or what's bad. And then Coinbase comes in and connect your PayPal and you can buy Bitcoin.

Like even transaction mechanics. Exactly. Are like, weird with angel.

Exactly. It's complicated. There's a million different places you're storing stuff. You're on Doxon, you're on Dropbox, you're on Carta. You're like, Oh, my God, this is crazy. So basically, that's how I see Cherib is really democratizing the angel investing process, making it really smooth, really easy, and also giving you the education for newer angels. So So one of our goals for the platform is to increase the TAM of first-time angel investors. So it's been really exciting. Of the $2 million, 40 % was their first check, and these are accredited angel investors.

Okay. I'm going to go on the record and say, I predict this is going to be your biggest success yet. I'm so excited about this, having been on both sides. I raised angel funding for my company a million years ago, and it was such a painstaking hackney process of just trying to hear the name of someone who had money to invest and hunt them down and take a million meetings. So streamlining it for the founders is great. But on the other side, what you just said about having made a $10,000 investment and then. Seven-figure Isaac. Yeah. So That opportunity should be available to more people. Exactly. Bringing angel investing to more people, to more women, as a wealth creation tool. Now, of course, it's super high risk.

It's super high risk. Yeah. Cherib is for everyone, men and women. Everyone always thinks it's just for win. But it is true. But actually, there's been a massive increase in women angel investing in the last five years, which is awesome. But yeah, it's inherently risky. But also buying crypto is inherently risky. Diversification is inherently risky. Yes, you can put money in. And I think diversification is the spice of life. You definitely want to be in the stock market. You definitely want to buy a house. You definitely want to do all the different things. You don't want to over index on anything, but you should diversify. And especially if you believe in a founder, you provide a specific expertise or value to that founder, they're more likely to successful.

Totally. And like you said, you have 25 angel investments. So when you come in really early and you invest, and you can, I write 5 and $10,000 checks too. I just feel like it's fine. And I don't have to put pressure on the founder then. I don't have to worry so I'm not going to say much about my outcome. And when you invest like that, you have to invest across a lot of categories.

Categories and companies.

What are your favorite categories right now?

I love food and beverage. I do think there'll be a lot of consolidation further down the line. My last investment I made was into intro which is a platform where you can book people like us on the app. And really, that was because I'm a user of the app. I'm on as an expert. I've had such a good experience with it. I've met so many amazing people. I truly believe in the product. The founder is awesome. I just felt compelled to be an investor in their future.

If you were going to start a company right now, other than all the companies you are starting, for anyone listening who's, I've got the appetite of it, but what are the right ideas and sectors right now?

Ai, I think, is the big We have a lot of AI on the platform, and they get a ton of investment. I think anything in terms of workflow, I think we're entering a new era of working from home, working remotely. Any tools that help with that side of the productivity, I think, are doing extremely well. If you look at something like a Canva that just completely disrupted the graphic design space, the deck creation space. Unbelievable, right? So things like that where you're taking something that actually can be made much better using tools like AI, I think that's a home run.

Okay. Ai productivity tools. That's what's going to get everybody their 100X return. Perfect. Yes. And we'll find those deals on Cherub. Yeah, perfect. And Cherub is open to everyone.

Just go to investwithcherub. Com.

Amazing, Jacquelyn. Okay, before you go, do you want to play a game of Never Have I Ever? Yes, let's do it. Never Have I Ever lent money to a friend. You have. Yeah. Okay. Did it go okay? Yeah. Okay. Good. Never Have I ever treated myself to a six-figure gift?

Car.

Oh, what car?

I got, post-divorce, I got a black Range Rover, sexy, baddy.

All blacked out. All black on black, yeah. Okay, good. I like that for I do. Okay. Never have I ever had money stolen.

Mm-hmm. Oh. Yeah. You can read about that in my book, WorkParty. It's my first business, but it's a long time ago.

Okay. Check out the details in Workparty. I. Never have I ever signed a prenup.

Oh, you did?

You had one? Yeah. Okay.

Took me a minute to think about that.

It's good that you didn't even remember. Do you advise that everyone get a prenup? I think so. Yeah. Okay, cool. Never have I ever paid on a first date?

I think I probably have because I didn't want a second date.

I was like, I got this. I see. Totally. I feel like it's the same for me. I don't have to count.

I just wanted it I just wanted it to end.

Yeah, totally. I just wanted it to end. Is that a signal to men that if you pick up the check- Probably not.

They're probably like, She really likes me.

Well, if it comes from us, it's a sign that we're not.

Yeah, I think just in general, though, it's a bad sign. It's not good.

That was fun. Okay, Jacquelyn, we end Money Rehab episodes by asking our guests for one tip that listeners can take straight to the bank. It can be anything personal, fine. What is your big money tip for our audience?

I think I said it earlier, but diversification is the spice of life. I think always be diversified in your investments, some risky, some less risky.

Amazing. Jacquelyn Johnson, thank you so much for coming to Money Rehab. Thank you.

That was so fun. This was awesome.

And that is the end of my last guest Hosting episode, at least for now. Next week, be sure to tune in when Peter Tuckman, a broker at the New York Stock Exchange and host of M&N podcast Trade Like Einstein, will be guest hosting Money Rehab. But I'll be back maybe as a guest host, maybe as a guest, all depending on what Nicole and her baby daughter need. Thank you all for giving me your ears this week. It's been a lot of fun, and I look forward to seeing you again soon.

My Money Rehab is a production of Money News Network. I'm your host, Nicole Lappin. Money Rehab's executive producer is Morgan Lavoy. Our researcher is Emily Holmes. Do you need some money rehab? And let's be honest, we all do. So email us your moneyquestions, moneyrehab@moneyrehab. Com. To potentially have your questions answered on the show or even have a one-on-one intervention with me. And follow us on Instagram @moneynews and TikTok @moneynewsnetwork for exclusive video content. And lastly, thank you. No, seriously, thank you. Thank you for listening and for investing in yourself, which is the most important investment you can make.