Hello, everyone and welcome back to a brand new episode of The Financial Confessions.

I am your host, founder and CEO of The Financial Diet, Chelsea Fagan. I'm also someone who absolutely loves talking about money in all its forms.

And today I am here with someone who works in a similar capacity to myself, who has achieved all kinds of incredibly impressive levels of success in her professional life, also has an amazing home that I frequently stalk on Instagram. She is herself a founder and CEO of a company you've probably heard of. She is also the host of a podcast, Work Party.

She is a dog mom of two, and she was kind enough to join today for a talk on all things being a female CEO, founder, entrepreneur, all of those great things. So without further ado, please welcome my guest, Jaclyn Johnson. Thank you for having me.

I'm excited to be here. And before we get started, I want to thank Avast for supporting today's episode of The Financial Confessions. Avast's new all-in-one solution, Avast One, helps you take control of your safety and privacy online.

Learn more about Avast One at Avast.com. Founder and CEO of what? Create and Cultivate.

So Create and Cultivate, if you don't know, we are an online platform and offline event series for women looking to create and cultivate the career of their dreams. So everything we do just ties back to career, whether you're a founder, CEO, entrepreneur, trying to climb the corporate ladder, we want to provide real talk advice to get you to the places you want to go. I love that.

And you-- so two things kind of stuck out to me when we were just talking right before the camera was on. You founded it yourself and the company, up through its acquisition, which was this year, majority acquisition, which we'll talk about later, was self-financed. Yes.

So talk to me about how you founded it by yourself, what that meant in practice and what it meant to be self-financed. Yeah. So it's interesting.

So I actually had a company before Create and Cultivate. So my first company I ever founded, I was 23 when I started it. I had no idea what I was doing, stumbled into entrepreneurship, and it was like a marketing and events agency.

That also was self-funded. But that business, which I had for about six years, was such a learning kind of playground of launching a business, truly not knowing anything, going into it making all the mistakes that you make when you launch your first company. So when I started Create and Cultivate, it was kind of nice because it was like my second time around, where I had learned from my mistakes in many ways, and still made many more in the future.

But I knew I wanted to be a solo founder. I had business partners in the company that were more silent partners that helped with the growth and strategy and things like that, so they held equity in the business but weren't day to day, like, they had their own companies and things like that, so more like advisors and things of that nature. In your first company.

In Create and Cultivate. Oh, in Create and Cultivate. And I wish I would have done that in my first company.

I was the solo, solo, solo in my first company, owned 100% of the business. And that was acquired by Small Girls PR. Who we used to, fun fact, when I worked at Thought Catalog many years ago in Williamsburg, Brooklyn, Small Girls PR was in the office across the hall from us.

Yes, I've been to that office. Yes, that's amazing. So yeah.

So they are a female-owned PR agency crushing it in Brooklyn. They acquired my agency in Los Angeles. That was my first time going through an acquisition process, which in itself is a whole other job, but then started Create and Cultivate after that.

So had a new lens, had a new focus, had made some mistakes, had learned from them, and then basically started Create and Cultivate. Got it. So the other partners that you had in starting Create and Cultivate, they owned some equity stake.

They weren't actively working in the company. Did they provide money, capital? No, so services really only.

So WE basically myself and one of the partners, put in around-- I put in $50,000 of my own money. She put in $250,000 of her own money. We were able to pay ourselves back within a year so that it was 100% debt-free.

The company itself was completely self-financed, and that's the only money that's ever been put into the company. Got it. But really, it was more for strategic kind of services.

The women that I had as part of the company had their own expertise in different areas. Whether it was celebrity relations or talent, they were able to leverage their network and expertise. And they obviously had skin in the game to help grow the business alongside me, which traditionally is what you would call it advisor.

You're giving them equity, they would like help you out in strategic ways. It was a little bit more in depth than an advisor, I would say, the relationships, but it was crucial to the growth of the business at the beginning of the business, I would say. Obviously, over time we had grown and had a lot of C-suite in place and 25 plus employees, it was less crucial to the business, but definitely in the early days.

Got it. And so it was a $300,000 startup little seed that then you reimbursed within a year. Yes, exactly.

Got it. And if it's not indiscreet, so at that time, you had how many other partners with you? So none.

It was just me in that one partner. Just you and that one partner. Yeah.

And you owned the majority. Yeah, and that was for the first, I would say, five years of the company. It was just me and her.

Maybe four years, something like that. So in that first, let's say, two to three years, where you were first paying down that initial investment and then I assume probably just breaking even and whatnot, how fast did you grow in terms of employees that you hired, expenses like having an office, all of that kind of stuff? Yeah.

So the thing about Create and Cultivate was it was insanely profitable from the beginning. It just skyrocketed. So what we started as a test kind of case study was, all right, let's do-- basically, my partner was like, I see these events you're doing.

They're really cool. I have a lot of access to talent. Let's team up and do this together type deal.

I can help you and support you. And I was like, I don't know. This is a side project.

It wasn't making money for a long time. I still had my other business. It kind of was in this weird gray area.

And then I was like, OK, well, I guess let's do one together and see how it goes. So we through our first conference. It was in Los Angeles.

I want to say in 2015, but I could be wrong on that date. And it was insane. We had 300 plus tickets sell out almost immediately.

We had sponsors like Bare Minerals involved. It was a disaster, don't get me wrong. I had no idea what I was doing throwing a conference that big, and it was one of those things.

I think we ran out of water, like, 4 hours in. It was just a mess. But it was great energy and people were so excited to be there.

And again, this was 2015, so no one was doing this. So it got a lot of momentum early on and it started really as a conference business, twice a year, different cities, different speakers, different vibes in each city. The staffing was small.

So the money that we put into the company went into the team. We brought on pretty much immediately an editorial director who would be able to take care of the website, manage all the blog content, things of that nature, an event producer, obviously, because we were doing events, and a social media manager. And those were the three employees for a very long time, and myself, obviously.

And everyone else was contractors. Everyone else was freelancers, contractors, things like that. And then we grew up to eight employees, I would say, year 2, and we kind of stayed at 8 to 10 for too long.

I crippled that. That was definitely my-- I just was so nervous to grow a team, I think, because I'd never gotten past the 8 to 10 mark in my first business. We were crushing it at 8 to 10 people.

Truly, we were profitable, we were making money, we were killing it. But things just kept coming in and I just kept adding freelancers because I was like, I don't know, what if it stops. What if all the interest stops.

There's that fear of growth, up until my partner was like, you need to hire. You're making money. You need to hire.

You're too bogged down in like what's happening and not thinking about how you're going to scale and grow. And you're doing everything and you're making a lot of money, which is great, but this will never sustain. So after that, I made a really key hire, and it was our COO/CFO who came on board, and she really game changed our business.

She made it institutionalized, she put everyone on different platforms, she added operations to the business, an HR element, and from there that's when we really scaled up to 20 and then 25 people. And now you have 25 employees. 25 employees. OK, got it.

So I imagine COVID really hit your business super hard as an events business. It was a true nightmare. I just remember so vividly in-- we, thank goodness, had our LA conference Feb 24, thousands of people, massive, massive event, which we were so lucky to get in under the wire from a financial perspective.

In March, we had our [INAUDIBLE] activation. We had over $2 million in sponsorship for that event, 7,000 RSVPs, talent booked, plane tickets booked. It was a done event.

And when Austin pulled the plug or the City of Austin basically held this press conference, we were all watching in our offices and it just was like, we're shutting it down. I was like, oh my God, oh my God. I knew at that moment, me, my GM, and my COO/CFO all got in a room.

We were like, all right. This is bad. We need to war room this entire experience.

But also what is this looking like three months, six months, a year? And I was, like the optimist. I was like, I feel like we'll be fine by summer.

It will be good by summer. It's fine. Let's just get through this.

And our GM was like, I think it's going to be, like, a year until we have events again. And we kind of-- everyone kind of danced around it, didn't know. We had to unpack that entire event.

We're very lucky that our sponsors stuck with us and transitioned to digital things. We moved very quickly into digital because I knew that's where everything was going to go. When everyone was going live every 10 seconds on Instagram, I was like, OK, we got to get on this.

But it was terrifying. I don't think anyone was prepared for it. I think I went into adrenaline mode and just was kind of like that duck above water, trying to act calm, but paddling so hard under the water.

And yeah, Q2, Q3 were really, really challenging. And we were lucky that by the end of Q3, I think most brands were like, OK, we got to spend money. We have to get out there again, and we were able to have a good upswing for Q4.

And we still ended the year profitably. Did you take a hit revenue-wise overall? Exactly.

Yeah. So we did $13 million in 2019. We were on track for $16.

We did $9 during COVID, which, obviously, brutal. But we were able to maintain the same levels of profitability because digital is very profitable, whereas events are very expensive. So it kind of opened our eyes to a whole new revenue stream and way of operating for the business, which was the blessing, I guess, in disguise, but also was challenging because we had, early in 2020, had a lot of acquisition offers and were coming off a really hot year, had a really strong Q1, and it was kind of devastating to then be like, oh, we're not buying an event business in COVID to be like, oh, great.

So that was a little rough. But that's when the deal flow started to come back by the end of the year last year, in different ways, shapes, and forms. I think everyone was scrambling.

A lot of media companies were scrambling last year to buy up things and put SPACs together and go public or whatever everyone was trying to do. And we were a little bit in that mix and then we decided to go the route of private equity. And were you-- so you were explicitly wanting to find a buyer?

Yeah. We were ready for the next echelon of growth. Basically, we were kind of at this point where we were like, we can go raise money easily, but that opens up a whole new can of worms in terms of the way your business runs, the type of activations you would need to do, how you would sort of double down, and what your revenue would look like.

And that would be to grow a massive company, essentially, and be up there with the likes of like a PopSugar or Refinery29 or something like that and understanding that side of that business. On the flip side, we didn't really need money. We were profitable, we were doing well.

Obviously, you can always use money, but we really just needed an active partner that would help us get it to the next level. And so we looked at strategic investors and partners that would make sense, so being acquired by a larger media company. But of course, every media company took a hit last year, so it was off the table in that way.

But basically, what we ended up doing was going the private equity route, meaning we cleared our cap table, besides myself, brought-- Can you, for the audience, clarify what that means? Yeah. So basically, the private equity firm bought out all of our partners that were on the cap table.

So if someone had equity, they were bought out, essentially. I was reduced in equity. I still retain a large part of the business.

But basically, this partner has expertise in growing, scaling, and building membership-centric businesses and events. So it's perfect for us. They've acquired companies like us in the past.

They've grown them, they've built them into $100 million businesses, sold some of them like further down the line in a secondary sale, and are highly active in our business and understood all of our pain points that were kind of stagnating the growth, and are now able to help us restructure, rebuild, and of course, finance things when we need them to, to help us grow into an even bigger and better business. So for us, we were at this inflection point where we just had so much demand, couldn't grow fast enough. Obviously, we're making money, but had a lot of people in the cap table that had to take distributions and-- Capitalization table-- Yes, sorry. --for those at home.

Sorry. It's like a little-- as you would see in Google Sheets, but it basically just shows a chart of the ownership of the company. Exactly.

Yeah. And the way you structure your business it depends on how you make distributions or tax distributions or how you run your business. It's very complicated, and as your business is getting bigger and bigger it gets even more complicated.

And so I think for us it was the right decision for the business coming out of 2020, too-- 2020 also-- but it was one of those things that for me personally, as a founder, having done it all on my own, it was nice to be able to have that partnership going into the next stage of the business. And so they have majority ownership, but you're still the CEO? Yes.

And so in terms of the decision making, I don't know if you-- we don't have to get into the super nitty gritty, but in terms of the level of decision making power and influence you still have over the company, where are you? Yeah, so they're very much-- their expertise is not my expertise, which is a good thing. I am the creative, the programming, the talent.

I love doing that stuff, coming up with the ideas, launching the events, doing all that stuff. The good news is, they don't like doing any of that stuff. They're like, great.

But what they can do is really operationalize and institutionalize the business from a internal standpoint, where they can bring in expertise on a financial level, on an operational level, on a strategic partnership level. They can also give us capital to test things, which when you're self-funded, not the easiest thing to do when you're like, let's just throw some cash at this and see how it goes. It's a little-- a lot scarier when it's your own money.

So they're able to really kind of double down on our instincts and gut and say, test it out, see how it goes. And they also know how to create recurring revenue, which is really, if you know anything about private equity, all they care about is recurring revenue. Where is the money coming from?

Is it consistent and how long has it been consistent for? And we have really strong recurring revenue, but it could be much stronger. And once we grow and build that side of the business, then we're able to go up for a secondary sale in which they will get a return on their investment later on.

So that's kind of where it's at. But day to day, luckily, my life hasn't changed that much. The business and the company and the structure has changed a lot in a good way, where everyone is much more streamlined, there's a lot more accountability, and the things that as a CEO I wasn't great at.

So that's kind of the biggest difference, I would say. Got it. Now I want to take a pivot to the philosophical because I do feel like a lot of times these types of conversations can be very focused on not just the really big numbers and sort of the shiny objects in that regard, but also very focused on the executives.

And I am personally very interested in a really holistic view of business and why we do it and the relationships we have with our teams, et cetera. So my first question in that regard is, what is your motivation for wanting to grow, create, and cultivate to that extent if, by your own admission, you were in a place where you were profitable, you were having a good-- the team was happy, you were doing good work. What's the motivation to grow well beyond that?

Yeah. I think for me, Create and Cultivate took on a life of its own more than I could ever have imagined it would ever get, which is really rewarding because I started it as a way to be like, do other people feel this way? Do other people want to kind of network and talk to each other and figure out and navigate this world of entrepreneurship?

And it turns out there was a lot of women who wanted to do that, which is very validating. Create and Cultivate is such an interesting company in that it is extremely profitable and an amazing business, but it also has a lot of meaning behind it and a lot of mission. I tried to describe what it's like after conferences to get cards from women who send me letters about how they negotiated a raise or found their business partner at Create and Cultivate, or whatever it is.

And that side of the business is so important to me. But I also think, as a woman in business who self-funded two companies, who sees the way the media sort of shapes the narrative of female entrepreneurs, and kind of has seen behind the curtain a little bit, I think it's really important to provide that peek in that insight into what it actually takes and demystify what success looks like because I think a lot of the things I read when I was in my first company and 23 and reading about all these women, I was like, oh, I want to be like her. I want to be on that Forbes list.

I want to whatever it is. Now that I know a lot of those women and I the way that things work, I'm like, oh, there's kind of a formula here and there's kind of a way to figure these things out. And we can't be kind of creating these smoke and mirrors to keep people at bay from being successful.

So that's something that's really important to me and keeps me motivated, as I love meeting founders and startups. I'm an angel investor in 15 plus companies. I love it because I can give them that lens and insight of expertise I didn't have in my first business and that I got in my second business by having partners who had done it.

So I would say that's definitely the motivating factor. And just continuing to provide really fun, really great experiences online and offline is something I'm really passionate about. I love doing it.

I love thinking about the experience from start to finish. So I think I'm really inspired and passionate about the business for myself and what I'm doing, but also for the people who are tuning in, and creating these really one of a kind experiences is really fun for me. But I'll also say, I think there is a lot of stigma around women and money.

And obviously, this is, like, your entire business. But I think when it comes to looking back on things, I never I put myself first when it came to the business and businesses, I should say, that I've run. I was just die hard make the business successful, make sure everyone can get paid, make sure all the consumers are happy.

But I would say one of the bigger mistakes I have made or made is that I didn't think about liquidity for myself until it was a little too late. Can you say more about that, liquidity for yourself? Yeah.

So I think when you're starting a company, for the most part, typically you pay yourself nothing. You're starting the business, you've got to get the team on board, you have to build the company, invest in the company, and all those things, especially if you're self-funded. So I did that for years and years and years, and I didn't really, until our COO/CFO came on and was like, your salary is laughable, and I get that you're dedicated to the business and want to grow and do all these different things, but you have to think about your path to liquidity.

You've been doing this a long time, you built a successful business, it's doing really well. What does your exit look like or path to exit look like? You mean your liquidity for your personal finance?

Personal finances. And I don't think women-- and in talking to a lot of people, founders have gone through this process now, and things like that. It's very similar conversation where it kind of comes last when you're building a company, and I think it's just really important to think about it.

Even if you're just starting out and you're like, great, in what world am I thinking about liquidity, I just started. But just thinking about what you want your end game to be because I think it's very easy to get wrapped up in all the sort of-- you treat your business like your baby and you care so much, and then it's hard to sort of let go. So I think that was something that I learned a little late in my second business but I'm happy that I was able to do that.

And I want to take a quick pause and once again thank today's episode sponsor, Avast. As a digital first media company, and as you can tell from today's episode, digital safety is incredibly necessary in all forms and is something very important to us here at TFD. Today's sponsor, Avast, has been a global leader in cybersecurity for more than 30 years and is trusted by over 435 million users.

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Learn more about Avast One at Avast.com. And now let's get back to our chat with Jaclyn Johnson. That's actually really fascinating.

I probably am from an ideological-- or not ideological, but just my philosophy on the issue is probably pretty opposite in the sense that, similar to you, for the first couple of years-- and I have two partners that you guys have met if you've watched the channel, but two other women who work at the company. So we're all together. But early on my co-founder and I-- have a third partner, came on later.

But we, to your point, paid ourselves almost nothing. And that, we slowly scaled it up as the company did. Now, to be fair, the company is much smaller.

It's only 12 employees. But I earn less than about half the employees, but that's a choice that I make actively. And we were actually, without getting into too much detail, speaking to potential investors earlier this year.

They got to the point of-- we went very far in the process. They were interviewing all the staff, this, that, and the other. And I heard the exact same thing, your salary is laughable on the market, this, that, and the other.

And that was, frankly, part of the reason I didn't want to do it, because I do feel a strong sense that, although what I do is incredibly important for the company, and I'm a unique case, similar to yourself, where I'm also actually part of the product, which is unusual for a CEO, I don't think that my work is many, many times more valuable than a lot of other members on the team. And so my question is, when it comes to-- and I agree we shouldn't be putting ourselves in a position where we can't pay our bills, we're not able to own a home or do basic things in life, we're not able to be comparable to at least what we'd get at a normal job, how do you mitigate the really big power differential you have as the CEO and deciding what is the chasm or the differential between what I'm earning and what my employees are earning? Yeah.

And I don't think it necessarily has to be your salary per se. It depends on the size of your company, too. For me, my salary didn't increase exponentially, but it increased to a place that was standard, where I wasn't earning less than pretty much everyone at the company for a long time.

But where I really saw the bigger picture value was in the how do I cash in this equity that I've worked so hard to build and grow, and what does that look like, whether you're raising money and you're going to take some of that money off the table, whether you go into an acquisition phase, whether you just sell some of your equity, whatever. There's a million different ways you can do it, but it's just thinking about that as a priority. But I think for the most part, CEO salaries, unless you're running like a 100 plus person or Fortune 500 company, that's when you're like, wait, they make $1.7 million.

And you're like, what? That's on the low end. Yeah, on the low end.

You're like, how is this possible? But that's where stock plays a huge thing. But I don't think it necessarily needs to reflect in your salary.

I think it's just figuring out how to get yourself up every year, or how to get yourself to a place where it's reflected because it's interesting because that came up in diligence for us as well, and there is a weird respectability thing that happens when you're in the room with those types of people, the venture bros, for lack of a better word, or the private equity guys or whatever, where they're like, wait, what? Because men never do that. No, they don't Men rarely underpay themselves.

No. So it's just an interesting thing that kind of stuck with me. And I think that's true right, but I think that also represents different schools of thought.

And I think that for a long time-- I think we're out of it now-- bless-- but the girlboss era of feminism, I think, looking back at it, to me, its worst excesses were-- its worst excesses were Elizabeth Holmes, who's literally a con artist. But the worst excesses to me were a framing that-- because I totally agree with you that there is a condescension there in these boys clubs rooms. There is a perception that their way of doing things is the only way.

They've, as you say, never question they're paying themselves or whatever it might be or how they treat their workers. I mean, how many companies out there treat their employees horribly? And I do think that in its worst iteration, a lot of the girlboss stuff to me was sort of an example of women achieving power parity with men to recreate the same systems.

And I do think, as women-- and I don't want to get too gender essentialist here, but as women, I think there are a lot of qualities that we do have that are often downplayed in work environments-- being empathetic, collaborative, listening, being more community-oriented, treating people with a higher level of humanity. And we're often taught to sort of tamp down those things and imitate men. And so I do think the question philosophically becomes, is the goal to operate the way men do and feel entitled to that?

Or is the goal to totally shift how we view bosses entirely and business entirely? I think it's the latter. And I think for me it's so funny because I just haven't worked with men in so long.

It's actually shocking when I see men-- I remember the first time I went to WME for a meeting. I was like, oh my God, there's so many guys here. It was so disarming because I've just worked with women for, like, 15-- like, that's all I know.

So it's interesting because I think, for me, the way I'm a leader I think definitely leans more into the feminine of the way it sort of works. But I'm able to, I think, financially being able to flex that muscle-- and again, it doesn't have to be masculine per se, but where going into that room what you want and what you deserve, I think that's really important as well. But to your point, I agree.

But I think there is a dismantling of the old venture capital way of doing things, which is really exciting for me. And I also think, as a self-funded business, it's impossible to get press. No one cares about your business, is it successful or profitable.

They're like, cool, what's your valuation? You're like, we're doing really well. But how much money did you raise?

And it's all these people who raise all this money, who are on the cover of magazines. It's just not the reality of what business is and should be and what the majority of business is. It's such a small percent of businesses.

And so I think there's been this kind of shift in awakening into the small business culture, which I'm really excited about because I think there's just so many amazing small businesses that women are starting out there, that are just getting maybe a friends and family round, or whatever it is, and being successful in their own right. I think that era of the girlboss era, in a way, what you're talking about, where it's cover of magazines, billion dollars, millions of whatever, anything at all costs, that's going away for sure. And I think for the best.

And I think also, not to break this to macro, but there is also the question of infinite scale. Capitalism's ultimate paradigm is a concept of infinite scale. And when you take that down to the more micro level and you look at the very concept of capital injections of strategic investments in a company, essentially they're only going to be-- it's not charity.

They're investing in you with an idea that you're going to increase profits, you're going to become essentially a more valuable entity, and that they'll probably be able to pass you off to someone else for more money. Or if we look at the case of publicly traded companies, what is the primary driver of that stock value? It's the profitability of the company.

And there's two kind of issues there that I think we have to look at from a more sort of foundational level. One is that you can't infinitely scale. Even if Create and Cultivate was killing it, you can't bring more than 9 billion people to an event.

You just can't. Exactly, yeah. So eventually that hockey stick is going to start to taper off.

And right now, the way we often frame it that is inherently a failure or an indictment of the model to some extent. I think that's problem 1. And problem 2 is that you can work it to some extent, but for the most part, profitability after a certain point is going to be at cross-purposes with things like employee benefits, salaries, investment in the pure resources of what you're creating, quality, editorial quality.

Things like that are always going to be weighed very unfavorably against profitability. So how do you correct for those things? Yeah, and profitability is what you get valued off of.

So it's really challenging to run a business profitably, to get that valuation, to get that exit, and make everything run smoothly and great and top quality for your team, the business in itself, and all that stuff. So it is like a paradigm. They're two oxymorons, kind of like, that have to run against each other.

But I think-- it's hard because I do think there's something in understanding what you want out of your business. And I think when people start saying, I want to run a business. I want to break even.

I want work-life balance, I want to be able to do this. I never want to grow past five employees. I think that's really admirable.

I think that's totally respectable and makes sense. And that's how a lot of businesses operate. Having a strong business, having the clientele you know and love.

I think there's this insane pressure to grow, scale, build, be as successful as possible. And I think that's really damaging because I think people assume they're failures if they're not doing that. And that's just not the case.

There's so many great businesses out there that are doing incredible work and making maybe $500,000 in revenue a year, and everyone's paid fairly and happy and it's going well. And maybe they'll grow a little bit, maybe they won't. That's OK.

And I think that narrative of the types of small businesses has kind of gone by the wayside, where it's just-- I always jokingly say that we're more like a Greek diner than a media company because we're actively not trying to scale at a really fast pace. I mean, we are not opposed to scaling at all, but that's definitely not the goal. We're explicitly not trying to maximize profits.

And we've actually several times explored the idea of becoming a non-profit. There's a lot of problems in that. I can do a whole video about that later.

But it does sometimes feel, unfortunately, that-- so we do have paradigms like that, a restaurant, a shop, there are certain small businesses that we sort of mentally can put into a box of they're there to make a product they love, pay everyone a fair wage, go home at the end of the day. And then we have businesses in other categories, media being a good example, where the paradigm and the model really only is that chasing of infinite scale. Right.

And I think they're too far apart. There has to be a middle of the road and there has to be sort of different strategic exits for all of those people that make sense. And I just think that we've gotten so-- and I'm a victim of it too.

I've gotten ate up in, I have to be doing this, I have to be making this happen, I have to grow, just because if you're in that mix, it's how it goes. And you start feeling bad about yourself. I would have times where I'd go to my friends like, we need to raise money.

And they were like, we make money. And I was like, yeah, I know but everyone's-- we should just go do it. And it was like, no.

There's that pressure to go out and raise and do the whole thing. And it's just-- some businesses absolutely need it, but just run a good company and enjoy that. How many hours a week do you work?

Oh my God. Well, it's kind of funny because it's definitely-- It's starting to ramp up again, but it definitely decreased during COVID. It was kind of crazy because I traveled all the time.

I was always on a plane, always going to the next big event, nights, weekends, whatever. So previous, I was probably clocking 100-hour weeks for the most part, which is-- That's so many. It's so many.

I worked all the time. On Sunday, I would work eight-hour days every Sunday, for forever. Oh, no, girl.

It was a lot, but I was so in it. And I honestly enjoyed it. I always try to tell people.

Someone's like, ugh. I'm like, yeah, but I was building, growing, building, doing the thing and I really enjoyed it. When COVID hit, it was very strange for me because it was like, one, all of our events got canceled.

We were transitioning and doing a bunch of stuff on digital, but that doesn't require building sets and heavy lifts and traveling, all these different things. So I had so much time, which was nice. I started working out.

I started integrating things into my life that I never had time for that I really love doing and that I'll bring back with me when we get back to normal. But I would say now, probably 50 to 60 hours a week, I would say. Maybe if I'm lucky, 40 on the norm scale.

But I get up early. I wake up really early and work before anyone-- like, 3 hours. I work from like 6:00 to 9:00, just because I feel like I get a lot done in those hours.

But I will clock at 5:30, 6:00. I'm, like, done. We are very-- our big thing this year is we're doing a four-day work week and we're very passionate about it.

I feel like, maybe challenge yourself to try it for a little bit. I know. I feel like I should.

I think working from home, it's just been so different. It's funny because it was always a struggle when pre-COVID because we traveled a lot, everyone wanted to work from home. But then we had comp days, so if you worked a weekend, you get a day off, whatever.

But it was getting so complicated with the amount of people because it'd be like, we have 25 comp days we have to put in. So it's like, the whole company is out for essentially a month. Figuring out the staggering of that and the work from home thing, it was such a nightmare and we couldn't get it right because it was just too challenging to be in that hands-on of an environment with events and have people working-- and no one was zooming at that time.

There was no language everyone spoke. So it's fascinating now like that we've been able to do it so successfully. And we're going back to flexible work.

We're having option to be in the office, things like that, which I'm really excited about. But I'm so much more productive at home. It's really interesting.

So even with this new thing, I was like, at least three days a week I'll be working from home, which to me feels like a nice-- That is nice. But I love an idea of a four-day work week. I think it's awesome.

It's so funny. We had been throwing around the idea of doing it for a while because we always did summer Fridays. And although we technically work till 12:00, we basically didn't work much on Fridays.

And it was kind of useless to even have that day for the most part because nothing productive was happening on it. And we had several staff members who, when we were holding the initial meeting, were like, I don't think I'll be able to do it. I really don't.

And interestingly, we just recently did our first follow-up and survey and everything, and everyone universally is like, I'll check my email here and there. I'll occasionally like send something out if I have to, but I'm pretty much not at all working on Fridays and I get everything done. And I think-- I mean, there are a lot of sociological studies that show that in a given 40-hour workweek, people are only actually working a very small amount of time.

And a lot of that is just taken up-- you browse your phone, you make a call, you have a snack, you watch a video. And when you don't do all of that stuff, I think, you really do realize that we're all much more productive than we think. We are we're just stretching ourselves out over this, frankly, quite arbitrary schedule.

It was only, like, 100 years ago I think that they instituted the five-day workweek, and it was really built around industrial work. We're now working with computers at desks that can be done from anywhere. Do we need to have the exact same model?

Yeah, no, I think it's going to flip after COVID. I'm curious to see-- there's been a lot of articles I'm sure you've seen about the great resignation, where everyone's going to start leaving their jobs that either go back to the office or go back to whatever type of thing, or they're like, wait, I can actually work-- people can hire remotely. We started hiring people remotely during COVID that worked not in Los Angeles, and they were amazing.

And it's like, you can now live anywhere, work for anyone. It's going to fundamentally shift the way work is done, I'm convinced. I just curious to see the way big companies react, small companies react, because it's kind of been interesting to see everyone sort of be like, OK, we're doing it.

Are we doing-- are we going back? We're going back. And then you have the one guy-- I forget who it was that was like, if I'm here, you're here.

The CEO of-- I think was Morgan Stanley, I don't know. But I was like, God, this is going to get-- but he was like, we can't pay New York salaries if you don't live in New York, basically it's what he was saying. Which I have real problems with.

I really don't think that should be as acceptable as it is because ultimately, if you're paying someone based on the value of their labor and based fairly upon their qualifications, that should be their rate regardless of where they live. Also, if they're not in office, that represents a huge savings for you as a business owner. You don't have to pay for their office space.

So one of the last things I wanted to talk to you about, and this was something that you guys asked about as well. So the relationship between being a founder, CEO, having this very not necessarily dominant, because I'm sure we both have other hobbies and interest, but a professional life that really takes up a lot of our space and energy and identity and having a family. I think, again, similar to moving on from girlboss, we've also moved on from having it all as a paradigm, and I think there are a lot more nuanced conversations now about professional family sort of dynamics and how they can be navigated.

And I'm curious to know what your thoughts on it are. Yeah, absolutely. So I'm married.

I don't have any kids. I'm 36. And I think-- my husband's 42, and he definitely wants kids.

We've definitely talked about it. I have felt like in the past, if I had kids, it would have held me back in my career, which is depressing. But just by nature of the fact that I am the breadwinner in our household.

I am the one running the company, previous to this completely on my own. And that pressure is debilitating in a lot of ways. And I see women do it all the time.

I think it's amazing. But I think I have so many friends that have kids that are incredibly successful entrepreneurs, and I see the real struggle of how it works. And I think there's definitely now an unveiling of that honesty, which I think is starting to happen, which I think is really important.

But I think it's, for me personally, it's been a difficult decision. I think it's something that I've put off for a very long time and I'm not really sure where I'll land on it. And it's a weird feeling in that way.

But I think that we as women put so much pressure on ourselves to do everything 100%, and I think when it comes to something like this, to your point, it's not the look at me, I'm doing it all, it's how am I doing it, who's here to support me, and how do I create that village mentality to get myself through this, because I think a lot of women I have suffered from postpartum depression, have had to go back to work too early, or whatever it might be. And I think, like those issues aren't getting talked about openly as well. What about you?

Well, I'm child-free by choice, baby. Everyone who's listened to this show knows I am that CBC. And some of you guys are like, Chelsea has two topics, child-free by choice and pay transparency.

And I'm like, listen, this is my show. Tune out if you don't like it. Anyway.

I have a lot of friends that way as well. And a majority, I would say, of my friends are in that boat. I go back and forth still of maybe, I don't know.

But I have so much respect for people that are just like this is my choice and this is the path I'm going. But yeah, I think there's no wrong way to do it. There's no right way to do it.

There's not. I do think for an internal litmus test-- and certainly this is not a therapy session. You don't have to answer this question in real time.

Let's do this, yeah. But I do think an interesting thing for my husband and I have been over the past 18 months a lot of people around us have gotten pregnant or started having kids. We've become aunts and uncles for the first time, this has all happened.

And I think a really good gut check for us has been, what is your feeling when that happens because every time, and increasingly so with each couple that this happens with, our feeling is, we are so happy for you. We cannot wait to spoil this baby rotten. Thank God this is not us, not in a, oh my God, it's the worst thing possible, but this is so not our journey.

And in that being so clearly not our journey, we feel even more happy for those people and even more like, I want to support you in any way that I can because I know it's going to be tough for you. And we're going to have a lot of freedom and privilege, and we want to be there for you. Totally.

My sister just had a kid. She's two years older. I was just down there for her birthday.

And I think it's like, especially when you see someone close to you like that go through it, you're like, oh wow, seeing the reality of it all. But I think that is a good way to put it. I think it's always just like, where does this fit into my life?

What do I want long-term? I'm also just-- I feel like I'm in an interesting place in my life because I've just been so head down building a company for eight plus years to actually have space to breathe, and COVID kind of accidentally provided that for me, to think about the future and what you want and a new chapter of-- all these things are kind of new to me, so I'm slightly overwhelmed, honestly, of like, who am I? Post-COVID, we almost died.

What do we want out of life, kind of having those like existential moments, and kids is definitely on the list of what's happening. So we'll see. That is really interesting.

Out of curiosity, so you probably have enough money personally now that you could retire if you wanted to. Is that fair to say? Yeah.

What motivates you financially? I think, for me, I love working. I'm addicted to working, in a good way, I would say.

I love putting output, creative output. When I look at my life and what gives me joy and what makes me feel value, it's relationships, friendships of course, but a large chunk of that is work. And I love it.

And so I think for me, what keeps me motivated from a financial perspective is really seeing other women make money. I think it's really something I've been especially motivated by in the last couple of years, not only angel investing in companies, but really just supporting women on their journey to get to a place where they can have that generational wealth that they maybe didn't have before that can really change their life, and then helping them put that money to good use. It's so fascinating because after the Create and Cultivate acquisition, I got probably around 15 emails from different female founders, some of which run companies you've definitely heard of, some of which are smaller that were just like, how did you do it?

How do we do this? How do we get to a place where we can do that? And I was like, yes, let's have these conversations and let's get you paid for the hard, work and let's make this happen because I just think women, from my experience, invest in other women.

Even from Create and Cultivate and me personally, I hire female florists, female caterers. When we're doing all these different events, I hire as much women-owned businesses as possible. When I decorated my house, I had majority women-owned brands in my house.

I always am trying to be cognizant of that. And I think women who have done the work and made their money are also like that. So I do think from a larger power structure, more women making that larger amount of money, being able to pay it forward to other women is how we'll actually see real change in a workplace setting, in a dynamic, is by having women have generational wealth, not just white men.

I think it's just really important. And so for me, that's what motivates me. That's what's exciting.

I love people who are just starting their businesses, in the nascent stages, and how I can help and grow and build alongside them. Well, to your earlier point, one area where I think that men would have the right to own it and you are not necessarily given that grace is I think men are very societally able to say, I love my job. My passion is my work, my passion is what I create professionally, and that's where my interest and validation and motivation lie.

And people would say, well, that's OK. That's enough. And I think for women, it's often like, OK, but you still want to be a wife and mom, right?

Yeah, it's selfish. And you still want to have all of these other interests that we put on to women. And not saying that you don't want them, but it's a woman who says, this is what I want and not these other things, I think is really pushed back against.

And I do think it's interesting when it comes to having it all, a lot of-- you were saying, at a time you were working 100 hours a week, which is your choice. And you said you were fulfilled in that. And honestly, work.

If you want to work 100 hours a week, you totally should. And a man in that space I think would never have even been pushed to consider whether or not, for example, he should also be a father while working 100 hours a week. I think you probably had the wherewithal to be like, this would be unfair to a kid, but men often don't.

And I think what we often underestimate is that people who grew up with fathers that worked 100 hours a week, and many people did, that wasn't good either. That is the paradigm that I think we need to shift is-- Shift, 100%. --if you are someone who is truly motivated by work and that is where your interests lie and that is where you're dedicating your time and effort, cool. But you can't do that and five other things, and we have to be OK to say, that's my thing.

Yeah, and that's my thing. And yeah, it's fascinating having gone into these meetings to talk about funding or acquisition or whatever, the amount of times I got asked when I was going to have kids was shocking. Are we getting into lawsuit territory?

Oh my God. What are we doing here? Because that is borderline lawsuit.

No, for sure. It was crazy. And our CFO, when she started coming to me, it was like, my jaw is on the floor.

It's insane. And one of the reasons why I actually love the private equity firm we went with is they were super respectful of the process but also very-- our CFO gave birth literally during the deal. And some people were like-- I'm just picturing her in the room, sorry, giving birth.

Truly, it was crazy. But it was like, no, we need to give her her time. And I've heard stories where similarly someone had to give birth during the deal, and they were like, no, we need her to sign this.

She needs to get on the call. People were pushing, and it was the most insane-- so disrespectful. That's barbaric.

Finding good people that aren't monsters. 100%. And the number of Boomer men business people that I have interacted with who proudly talk about working 100-hour weeks or whatever have four kids. I'm like, cool job, Dad.

And the thing is that, listen, I work 32 hours a week. I just don't want kids because I'm a selfish heathen. But I will say that truly it takes, I think, a strong person to be like, I love this and this is what I want.

So to finish up, we have, as you guys know, our rapid fire questions. It's whatever comes to the dome, no right or wrong answers. Feel free to pass.

Just pulling them up. Give me a second. Where are they?

Here we are. What is the big financial secret of your industry. And if we could talk venture capital, I think that would be very interesting.

Big financial secret. I would say, only take as much money as you need. I think people get caught up in taking as much money as they can get.

And I think that's a bad financial decision. I love that. What do you invest in versus what are you cheap about?

Oh, man. Real estate. I'm on Zillow and Redfin every day of my life investing in real estate.

I'm cheap about probably clothes, honestly. Where's that t-shirt from? Zara.

What? Yes! I was like, I thought that was some fancy designer.

This is what I'm saying. It's not like I-- but it's funny. Every now and then, I'll be like, I'm going to up level.

This is it. I'm going to buy that $1,000 dress. And then I get it.

And then it's like, you wear it once and it kind of falls apart. And it's the most depressing-- I can't get behind it. Yeah, no, me either.

So clothes. What has been your best investment and why? I mean, back to real estate, but definitely my first house.

So I bought that house right after the acquisition from Small Girls, and it was obviously a big investment. I was very nervous about it. I put a lot of money down in Los Angeles, and it's, like, doubled in value.

And that's the house you currently live in? No, it's the first house I bought. And it was just in a really-- it was so funny because my aunt's a real estate broker and she was like, get it.

Do it. And I was like, oh, no. It's a terrifying decision that you can make very quickly.

And it ended being an incredibly smart investment. And you what-- can you give us a percentage what you made in return? Yeah.

Well, so we bought it for $895,000. We put about, I would say, $150,000 into it, and it's worth, like, $1.8 now. Wow.

And you sold it or you held on? No, we still have it, yeah. We're going to hope it sells soon.

Damn. What do you do with it? We're renting it.

So yeah. Duh. Income property.

It's just sitting there. It's just their second residence that they go hang out in. I would do that if I could.

What has been your biggest money mistake and why? I think probably not putting my money in a money market or a money making account early on, in my 20s, I think. And it's funny how many people I talk to that are like, wait, what do you mean?

I'm like, no, you put your money in an account that earns interest and you grow it over time. I think I just learned that a long-- later in life, and I wish I would have done it earlier, compound interest. That's true.

What is your biggest current money insecurity? I mean, COVID, I guess, in the sense of things aren't-- things were normal for so long and I think we really took that for granted in terms of financials. And of course, you get up and you go and you work and you do this and that.

And that just leveled everything that we knew about money and how it works. So I think still rebounding from that a little bit, it's making me nervous. What has been the financial habit that has helped you the most?

I think getting alerts on my credit card charges. I get them sent to my phone, and I feel like it's always helpful because it's so easy to just like swipe and swipe and swipe and swipe and swipe. And then all of a sudden, you're like, oh yeah, that thing.

And also it's just disturbing how much Postmates I order. It's really upsetting. I wish I could say that I didn't relate to that.

And lastly, when did you first feel successful and what does that word mean to you? I think I first felt successful when I was on the Forbes 30 Under 30 list. It was a huge-- You were one of those gals.

I was one of those. I was 29. I was holding on.

I was like, this is it. But it was nice to be recognized by a business publication. I think I'd gotten press in fashion and beauty and blah blah, blah.

And I think it was just a really big moment for me, and yeah, that was great. Was there a second question? Wait.

What does the word "success" mean to you? Oh, success. I think being happy when you wake up and what you do every day.

I think if you wake up and dread that meeting or that whatever it might be, it's like, you got to just switch it up. Love that. Well, it has been such a pleasure.

I have truly really appreciated your candor, and I think few CEOs and founders speak as thoughtfully and honestly as you do about these things. Oh, thank you. It's been a pleasure.

And if people want to learn more about you and what you do, where do they go? Yeah. So you can follow us on Instagram @CreateCultivate. @WorkParty is our podcast, and I'm at @JaclynRJohnson or CreateCultivate.com.

Go look at that house. My goodness, my goodness. All right, guys.

Thank you for tuning in and I will see you next Monday on an all-new episode of The Financial Confessions. Goodbye. [MUSIC PLAYING]