How Do You Afford This?

#07: This Founder Raised $20M. The Exit Was a Zero

• Ashley Feinstein Gerstley • Season 1 • Episode 7

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0:00 | 47:06

Helaine Knapp is a serial entrepreneur, the author of Making Waves, and the host of the Step Into Next podcast. She founded CityRow, the rowing-based fitness brand that landed in studios across the country and homes around the world, and now splits her life between Austin and New York. In this episode, she breaks down how she affords it, starting with the most honest founder money story we've had on the show.

Helaine and I walk through CityRow with a financial lens: the $0 marketing budget that made it explode, the $12 million she raised in six weeks during COVID, the more than $20 million she raised in total, and the exit that came out to a zero for her investors and for her. Plus, what two years on a GLP-1 has actually cost her, from the $1,000 consults to the surprising ways she’s spending less. 

Helaine reveals the scrappy strategies that fund a life in two cities, what it felt like to be on the Today Show and unable to pay rent, how she handles the awkward money conversations most of us avoid, and what she's working toward affording next.

Download Ashley’s ‘Become Your Own CFO’ bundle (https://www.thefiscalfemme.com/cfo-bundle) for everything you need to manage the money you make in a strategic and financially savvy way.

Subscribe to Helaine's weekly newsletter (https://www.helaineknapp.com/what-im-building) and her Substack (https://helainemknapp.substack.com/)

Get Helaine's book, Making Waves (https://www.helaineknapp.com/making-waves). 

Check out Ashley’s Money Club (https://www.thefiscalfemme.com/money-club) to join a community of women unabashedly going after their money goals. 

Take this quiz to get a personalized Wealth Building Blueprint (https://bit.ly/4v94g2C)

SPEAKER_03

Well, I'm on the today's show and yet I can't pay my rent. I am sought after, I am well respected, I'm doing insanely cool, amazing things, and the dollars don't reflect it all the time.

SPEAKER_00

My guest today is an entrepreneur, author, and founder who raised over 20 million and built one of the fuzziest boutique fitness brands in the country, and then had to figure out who she was without it. And as always, we get into the actual numbers. Helene breaks down the real financial story behind City Row, the zero dollar marketing budget that made it explode, what it actually takes to raise money as a female founder, and the moment the whole thing came crashing down.

SPEAKER_03

We basically just never had enough money at any point in this journey.

SPEAKER_00

She shares how she rebuilt and is rebuilding, and the scrappy money strategies that let her live between Austin and New York without paying for both.

SPEAKER_03

I do not mind renting out my apartment or my car. I just think it's like an asset of mine that I should make money out of all time. I don't say never money.

SPEAKER_00

Plus, why she plans to build her next business in the GLP1 space, what her own two-year journey on Zephbound has actually cost, and why she thinks we'll all eventually be on GLP1.

SPEAKER_03

I took my first Zephound shot and I have not looked back. I understand why I was so resistant to it, and also it was such a beautiful gift that I gave myself to turn off this noise that I've had for my entire adult life.

SPEAKER_00

I'm Ashley, certified financial planner, founder of the Fiscal Fun, and I'm asking the question everyone is already wondering. How do people actually afford their lives? This is how do you afford this? So excited to have you here. You founded multiple businesses, including your current venture until GLP Ones, which I'm very excited to talk about. You're an author, podcast host, you live a fabulous life in Austin and New York. Like, how do you afford this?

SPEAKER_03

I don't know. I'm really scrappy, Ashley. We'll get into it, but I I am as about as scrappy as you can get. I'm always looking for a deal or a barter. And I don't know. I think when you're like in flow, things just happen.

SPEAKER_00

I love that. I see it too. Any like highlight of the scrappiness, like one thing you're like, this defines how scrappy I am.

SPEAKER_03

I do not mind renting out my apartment or my car. And I just think it's like an asset of mine that I should make money on at all times.

SPEAKER_00

Your car and your apartment are earning you money.

SPEAKER_03

Yeah.

SPEAKER_00

When you're out of town.

SPEAKER_03

Yeah, like I'm not, I don't say not of money.

SPEAKER_00

Is it when you're out of town or all the time?

SPEAKER_03

I'll when I'm out of town. I'll intentionally be away from Austin during South by Southwest, also because I have zero interest in that. But peak times of year, over the holidays, like I will make sure that I can get someone in there who's gonna pay top dollar and then it like helps me pay for my trips and my and my plans.

SPEAKER_00

I love that. I love it.

SPEAKER_03

No problem. Someone come in my space, sleep in my bed.

SPEAKER_00

Have you had any bad experiences or so far, so good?

SPEAKER_03

Knock on wood. So far, so good. I love keeping it like one degree friend of a friend. I've had bad experiences where I've rented people's houses, but not when someone has rented mine. I think of a wonderful host.

SPEAKER_00

Where the place wasn't what you expected, or you were a bad guest.

SPEAKER_03

The place was low blow. The place wasn't what I expected. One one was in LA and there was like a crazy bug infestation. And the guy mortified. Like he was like, I thought he was gonna cry, but I also was gonna cry. And like it was horrible. And then one was a short-term rental, and she just clearly had some kind of pet before me, and I was so allergic I had to like leave before the rental.

SPEAKER_00

Less gross, but also very uncomfortable.

SPEAKER_03

Yeah. So not ideal, but you know.

SPEAKER_00

Yes. I think we've had one bad review of us. And I would argue like it was a we were last minute, couldn't find something, and so we put a pillow on the ground, like from the couch. I feel like it was an unfounded bad review, but anyway, otherwise, we've been good guests. So I want to start with GLP ones because everyone's talking about them and the costs are wild. What brought you to the space? And like tell us about what you're building.

SPEAKER_03

Yeah. The space kind of found me. I mean, if I take a bit of a step back, I am obviously I built a company in the fitness space for over a decade, but how I ended up getting there is in part my own personal story. Being an overweight kid, adolescent, teenager, over 200 pounds in college. And then after college, I really kind of found a healthy, balanced lifestyle. I was on Weight Watchers, I was going to the gym, I was doing all of the things. I lost a bunch of weight. I started to feel really good about myself. Boutique fitness became an outlet for me from a physical perspective. And that's how I ended up starting my company, City Row, which is the rowing and strength training concept. Actually, still exists. You want to buy a rower at home. But at the same time, I really could never really shake the last 20 or 30 pounds that I wanted to. So I was like very like my body really liked 190. I like really was quite happy there. And so after City Row, the last couple of years were really, really, really stressful for me. A friend of mine said that they were on a GLP one. And I think I cried because I was so upset that this person who was so close to me would go on a GLP one because it felt like cheating. And I could not fathom the fact that they did that. And I was like, well, that's for celebrities and like the Kardashians, and that's not for like normal people. And then four months later, SR and I was like, uh, what is happening? And then our other friend, we were all kind of cruising at a size 10, 12. And then our other friend's like, oh yeah, I'm gonna get one through hers. And I was like, fuck it, I'm not gonna be left behind. You know, I'm I'm a I'm a trendsetter, actually. I'm also I'm a follower. And these are people that I like deeply love and respect and would like really follow and trust their advice. So one week later, I took my first Zetbound shot and I have not looked back. I understand why I was so resistant to it. And also, it was such a beautiful gift that I gave myself to turn off this noise that I've had for my entire adult life and achieve something with help. I'm not great at asking for help. And so I have been on the journey for almost two years. And as part of thinking about what am I gonna build next, I am I'm a three, five generator, actually. So I'm building from human experience here. And so many people are always coming to me, GLP one curious, or they have a question, or they're nauseous or something, don't want to go up on a dose. And I've always kind of been the person people go to. And so finally I was like, this is such a wild, wild west. The numbers are astronomical. Anytime you go from 5 million to 30 million people entering a category, crazy things are gonna happen. Like I should show up there and not just help people navigate, but like see what's needed. And so that's that's why I'm here.

SPEAKER_00

I actually heard that last week. It's like, if you're trying to figure out what to build, what are your friends texting you like in the group chat? Like, what are you known for? What are people coming to you for help with? And that's exactly like where this is coming from.

SPEAKER_03

Interesting. I haven't heard that. So I feel like that's a nice confirmation of what I'm doing. So honestly, I don't exactly know quote unquote what I'm building yet. I don't have, I'm not building an app, I'm not building a supplement, but I have a lot of hypotheses. And to start, as an entrepreneur, you want to actually start by listening. And what that means for me is actually just showing up in conversation and seeing what percolates and seeing what happens and seeing what comes to me as a result of showing up. And that means I do a weekly newsletter every Tuesday. There's a roundup of the news that you should be paying attention to in this world alongside a deeper dive substack of longer form editorial, some personal, some more research-based stuff. Like, what are the actual effects of this that's not weight loss? And also, like, how do you come off of them? Those types of things.

SPEAKER_00

So I saw your recent one about coming off of them. I thought that was so interesting. And this might be a silly question, but you said, I'll get it through their them. Like when you when your friend was on it, you're like, I'll get it through them. Like, what does that mean?

SPEAKER_03

She was saying that she was gonna sign up for hers.

SPEAKER_00

So hims and hers is funny. Got it, got it. Okay. It was like through her person, through like her dealer.

SPEAKER_03

Like it's not not a dealer.

SPEAKER_00

Yep. Can you walk us through the costs of that journey for you and like what you're paying now? For sure.

SPEAKER_03

And then I'm also happy to talk a little bit about the fact there's a million different ways to think about the cost for this. I think if people are able to get it through insurance, it could be as little as zero dollars. And when I started paying for it, I think the top doses were close to twelve hundred dollars. I chose, again, this is two years ago, which is you know an eternity in the GLP one world. Then I should see. Yeah, I chose to get a fancy endocrinologist on the Upper East Side because my best friend who had started them, I trust her implicitly when it comes to anything medical. She does more research on things than I could ever even fathom considering doing. So I wanted to copy her homework. Went to her endocrinologist, paid a thousand dollars for a session, which was insane. But it's a consult. Yeah, the consult. And they know what they're doing over there. It's also completely out of pocket. It's not covered. The doctor is also not covered with insurance. And I knew that because I also have a very weird Texas insurance, which we don't have to get into, but hashtag entrepreneur life. And I was like, this is a problem that I've been personally trying to solve for my whole life. So that's definitely worth whatever this thing is gonna cost. And then she prescribed me the the like lowest dose of Zetbound, which at the time I was paying $750 for.

SPEAKER_00

And that is monthly, weekly, monthly. Monthly, okay.

SPEAKER_03

It was expensive, a very, very expensive thing in my life. And yet every month I could rationalize it. Not only because you're eating a little bit less, for sure. I mean, that's for sure. The food bill definitely goes down, not by $750, but the value that I'd put on it is worth it for me. Right. And since then, the costs have come down. So the doses that I'm on, like I ended up kind of going up to, you know, two or two doses higher than that. But right now, I pay $450 directly to Eli Lilly. And I've been able to move away from that fancy doctor and get it prescribed through my one medical doctor. So I'm not paying the doctor fee anymore.

SPEAKER_00

I'm just paying for my monthly shot. How often did you have to see the endocrinologist when you were seeing them? Was it like a one-time?

SPEAKER_03

In the beginning, I saw her, and the follow-up sessions were only $500, Ash. But I probably saw her total three times. Yeah. Okay. I probably saw her a total of three times, two follow-up sessions, maybe three follow-up sessions virtually after the first in person. And the first one was kind of worth it. I I didn't know what I was getting myself at. I was really scared. And then afterwards, I was just like, well, this is fantastic. And then it was more just like, am I doing all the right things? Am I thinking about it in the right way? So more like confirmation, but I also know that I was actually like a very, very good candidate for this. Like, have very good habits for the most part. And so this was just like a little bit of a turbocharge on what was already like a pretty healthy baseline lifestyle.

SPEAKER_00

Yes. And you mentioned the costs for other people and how sometimes it can be covered by insurance. Curious on the other, like how that can look, but then also any costs that you didn't expect or like things that are other than the like the GLP one itself.

SPEAKER_03

For me, I think a lot of the costs were already baked into like quote unquote a healthy lifestyle. So I already have protein powder that I was using monthly. And that became a bit more of a staple for me, a bit more of a priority. I already had a subscription to electrolytes. That's evolved over time, but that also became more important to me. I wouldn't say there were any other changes. I also already was seeing a personal trainer. So those costs were baked in. I think it's more the costs are around are you making a full lifestyle shift or are you just adding the pen? If you're just adding the pen, you're actually probably going to be spending less because you're also not interested in drinking alcohol. You're going to be spending a lot less on dinner. What used to be, say you're going out with someone and you're each getting an appetizer and an entree, you're now probably getting like two appetizers, maybe one entree. Like it is a you're actually saving money in some areas. So there's not any like extra cost with taking this shot once a month unless you're layering in more personal training or nutrition coach or something like that.

SPEAKER_00

That's so interesting to the alcohol too, because people you can spend a lot on drinks.

SPEAKER_03

Like I haven't been a big drinker for many years. And when I go to dinner, I'm just like with people that are drinking, I'm truly shocked because that is where all the money is. Like we should get into alcohol, except I do think that we're a downward trend. But it's actually, it's true, it's actually completely insane.

SPEAKER_00

Yes. Whenever people we go out and there's no drinking, we're like, wow, this was so affordable. You know, it's like, that's why.

SPEAKER_03

It is so affordable. It is kind of insane. So, I mean, to your question on what this costs other people, it really depends on if the employer covers this with the insurance plan. That combined with do you have enough of some of the biomarkers and pre like preconditions, like a combination of obesity and PCOS, cardiovascular, sleep apnea, like there's a lot of conditions that you need to have. Ideally, I mean, outside of diabetes or severe obesity to be able to have this covered. Not a lot of employers are covering this. And it's actually decreasing in terms of which employers are covering it because it's so expensive. And there's not any immediate return for the insurer for someone to go on this. Unlike diabetes, right? If they're, if you're not covering someone's insulin, like the cost of them being in a hospital is astronomical and immediate. There's no immediate downside necessarily for someone to go on these drugs. The, the, the, what actually happens as a result of going on these drugs in terms of like massive health benefits, hit when you're on Medicaid, Medicare.

SPEAKER_00

Right. It's like preventative care in a way, where it's like so important, but not immediate.

SPEAKER_03

Incentives are not aligned right now. And I think we're gonna start to see that change. We're also gonna see a lot more drugs coming onto the market. I'm very curious to see what's gonna happen with compound pharmacies. So those that are creating like a slightly different version of it so it doesn't breach the patents that Eli and Nova Nordists have on ozempic or semi-glutide and Zetbound and Terzepatide. So we're gonna see a lot more competition. We're gonna see more things entering. Like there's gonna be a price driving down scenario over the next couple of months and years that we're gonna see a lot over time. And at the same time, we'll get generics, not as soon as we think. So patents run out in 2031 for terzepatide.

SPEAKER_00

I was gonna ask because it's you said we're like a few years in that typically last 10 years first for generics. Wow.

SPEAKER_03

But like my my hope is that there will be more affordable ways to get this for people in a million different capacities, or the cost will just be so low that people will find a way to pay for it. I'm gonna be I'm gonna be honest, I don't actually know how it's gonna happen, but the fact that we're joking about it being in the drinking water, all the research that I am seeing, unless you have strong gastrointestinal issues, this is like everyone should be microdosing for reduction in inflammation. Like uh fluoride.

SPEAKER_00

It's like a little bit goes a long way.

SPEAKER_03

For sure. And we're gonna we're gonna get to monthly shots soon. I think there's like a little bit of controversy in if it needs to be, if it can really be an oral. It can be, it's a little bit different. Uh it's actually more expensive because you have to put more of the actual molecule in an oral because so much of it gets destroyed in the gut. Uh but the actual cost of like these drugs are in the sets.

SPEAKER_00

Wow.

SPEAKER_03

Somehow they become like a thousand dollars.

SPEAKER_00

And typically the shot is weekly?

SPEAKER_03

Yes.

SPEAKER_00

You said, but it might move to monthly, and the the oral is daily. Correct. Okay. Knowing what you know now, like having been on this journey for two years, is there anything you would have done differently if you could do it again? I would have started much earlier.

SPEAKER_03

And I probably wouldn't have cried right before I did the first shot because it's the smallest I've ever seen in your whole life. And I like FaceTime my friend who's like, you know, a nurse, and I was like, let's do it together.

SPEAKER_00

So I mean, I get it, yes, but I'm sure you're such a pro now.

SPEAKER_03

I don't even think about it. And even other people that have started it after me, who I would say are maybe like less of a G in this, like, you know, medical, like, you know, fitness wellness world, they're also like, oh, what shot? Wow. Well, I always tell people if they're afraid of the shot. I hear you, a lot of people are afraid of needles. You can do anything for two seconds. Try this once, and if it's still an issue, never do it again. But try it once. It's it's it's like a true nothing burger.

SPEAKER_00

Yeah. That actually was something I had at like in a workout class. They're like, you can do anything for 30 seconds. That was like how they kept us going from in the workout. Yep. All right. So you mentioned City Row. Let's rewind because it's not your first rodeo. You built and exited City Row. Can you give us like the highlight reel of that process? Lowlights are welcome to, and just share a little bit about the financing journey and if you can share like what the exit looked like for you. Sure. How much time do we have? That's a big question. Yeah. I'm like the queen of the multiple layer question.

SPEAKER_03

I got you. I can I can run through this story with a financial lens. It was a 10-year journey. So there were a lot of aspects to it. And the there was a lot of highs, a lot of lows. The the highs were really, we created something from nothing. I had this idea to create, bring something to market that was high intensity and low impact. I'd never rode before. We hit the market at the right time when there was just actually truly not enough supply for the demand of boutique fitness. We were brand new. I had a knack for media and PR. We hit the influencer game very hard. And the first location did really well with zero marketing. I spent zero dollars on that location. All of the mistakes were in many subsequent years. I had a lot of trouble raising money. I'm a tech founder. I was in the tech world before I opened a brick and mortar location. So I had a very different lens to it. I always knew we would go really, really, really big. Didn't quite have the economics to support a fundraise. We opened our second location on the Upper East Side two years after. Didn't have enough money to open. And so couldn't pay our construction loan. Had to like, you know, wheel and deal a loan that we then couldn't pay over time. Like we basically just never had enough money at any point in this journey. And we ended up, I mean, I had a hundred people on my cap table before we exited. A hundred people because I was very good at raising money from individuals and angels in the 50 to 100 range. When it was looking for institutional, City Row was very different because we had this four-wall business that wasn't mature enough to attract the four-wall investors. But then I launched City Row Go, which was our at-home rower and content and app. So we were think of an orange theory meets a Peloton. That was our ecosystem. And it was genius because people cycle through these things and yet could not find an investor where we fit in there. We didn't fit in a box. We didn't fit in a tech box. We didn't fit in a hardware box, didn't fit in a four-wall box. So fundraising was very, very, very difficult. I did it piecemeal over the first six years, always, always running out of money. There were years I didn't get paid. There were moments where I had to tell my executive team you're not getting paid on Friday. It was brutal. And it felt horrible at every turn. In during when COVID was about to hit, we had just started franchising about a year before. We'd opened our first couple of franchises across the country. We had our first at-home rower in the market. And what COVID did was just throw a tsunami on the business. And so, yeah, I would not say that that was a highlight. I would say that was a the beginning of a low light with some weird, weird peaks because we had this digital thing. And so our studios could kind of leverage that in the early days, and it was fun and creative. And the press that we got was out of control for those first couple of weeks. And then the franchises started to shut down. And then our digital business was booming like crazy because we had an at home product in market already that we were already shipping. And so that summer, as my franchises are basically dying, and these are people that have turned over their 401ks to build on my concept going out of business with SBA loans. We can't actually deliver enough machines for the demand that we have. Peloton was at an $8 billion market cap. And while it took me seven years to figure out how to raise a Series A, I raised $12 million in six weeks.

SPEAKER_02

Wow.

SPEAKER_03

And then six months later, the entire bottom fell out of the fitness category, the connected fitness at home category, because we had pulled forward so much demand there wasn't any left. And so it was COVID was really the beginning of the end with a few little bright spots, or so I thought. I've been driving towards that large fundraise for so long. And then it ended up being one of the things that I think was ultimately quite challenging. And so the last three years were is there a way to land the plane somewhere? A lot of cutting, a lot of firing your friends, a lot of shutting down certain parts of the business, trying to get to profitability and break even. I'm a cockroach. I would keep going. I had a board member, wonderful woman named Sharon, sit me down with a 30-page PowerPoint. But that was basically like, it's time to stop. So then I cried for two weeks. And then I was like, okay, let's try and land the plane. Ran an MA process, no bites. Whole industry is suffering here. The whole industry. Ran it again, got a bid from a competitor who's adjacent. We were in diligence and negotiating for six months, and they pulled out on the closing call. Oh my gosh. I know. After my book, I'd written a book during this about my whole journey, the process, the underbelly. The book had already gone to print. And I had to call my editor and be like, hey, Debbie, I have a material update. And she was like, you need to keep the edits to three pages. And I was like, okay, fine. So we ended up basically giving the business to our senior debt holder, who was our manufacturer, in exchange for their debt. So they had a little over 2 million in debt. And we kind of gave them the assets of the business in exchange for absolving that debt. We also had, we had two other debt holders that we were like, listen, we might get some ERC checks over the next little while, and we'll pay you, you know, maybe 20, 30 cents in the dollar of your debt for that. And then, oh, investors, I raised over $20 million was a zero for them, which also means a zero for me and for everyone on the cap table. And we also didn't get paid for quite some time because we'd run out of money. So it was on paper, it was a zero. I struggle with it for sure. And then every once in a while, you know, I get an email from City Row and it talks about new classes. And I was talking to my, you know, co-founder last week, and we were just like, wow, we actually created something that still exists. And that's that's pretty cool. So yes, I wish there were economics. And also we create something really powerful.

SPEAKER_00

I love that. And also, how did you handle the years where you didn't get paid? Like, what did you do?

SPEAKER_03

Honestly, it was brutal. I had some savings before going into starting City Row. And so I would, I would deplete that pretty aggressively. And I would sometimes I would have to call my family and ask for help.

SPEAKER_00

And they just were, they were supportive.

SPEAKER_03

Incredibly supportive. It was embarrassing and it was hard for me to ask. And yet fortunate that I have a very supportive family. And they definitely saw this as my graduate school. And maybe on some level they got out, you know, better. But incredibly supportive. And luckily they had the means to do so. But as somebody who is like prides themselves on being very successful, and you know, I was very successful before I started this financially. And I remember my dad being like, oh man, this is great. I finally have a kid that's like off the payroll. And then here I am opening a brick and mortar business. So hello. It's a hit. It's a hit to the ego because you're sitting here and you're like, wow, I'm on the Today Show and yet I can't pay my rent.

SPEAKER_00

Entrepreneurship is humbling, if not anything else.

unknown

Right.

SPEAKER_03

It's confusing. You're like, I am sought after, I am well respected. I'm doing insanely cool, amazing things. And the dollars don't reflect it all the time.

SPEAKER_00

It's funny because this leads perfectly. I was gonna ask about taking time to travel afterward, which after hearing that story makes a lot of sense. You wanted to take some time to yourself. Can you share about how you made that decision and what you budgeted for for like the that time?

SPEAKER_03

So as soon as City Road was starting to wind down, I was like, I need to make money. I was like, this is this is killing me. I also need things to do that are not depressing wind down. So I started doing like strategic advisory consulting work as soon as I could, before the ink was dry on that paperwork. I was, I was working. So anything from executive coaching to strategic advisory to short-term projects, helping companies get off the ground and fractional COO work. I started putting myself out there in terms of like contractor for hire, effectively. And so that gave me flexibility, gave me a little bit of income, made me feel useful and valued with some purpose coming out of City Row. And so it's the consulting work and the coaching work and the strategic advisory work that allowed me to have the flexibility to pay my bills, to figure out how to get myself on some of these trips. And a few months after we sold City Row, my book came out, which, you know, hopefully this is not a shock to anybody, but there are not a lot of economics on books. However, it was a relaunch of me that allowed me to kind of help bridge that transition. So the book was like a bit of a guiding, bright North Star for me that I was able to celebrate and then move into another consulting project with a friend of mine at a company called Loop and Tie, which is an unbelievable, sustainable gifting company, supports small makers. And that was a much like meatier consulting project that gave me flexibility and also the ability to like calm down a little bit. And that was the beginning of I'm gonna go to Bali for five weeks, figure out like hopefully that'll fix me. Turns out I came back from Bali being like, whoa, I'm burnt out. Like, and so then I was like, this whole year needs to be more of this. And so that's how I ended up, did a little bit of Europe. I did the Hoffman process, which was incredible. What is the Hoffman process? It's this unbelievable, it's a seven-day retreat, no phone, no connectivity, no working out, no music, no nothing. And you are doing a lot of work on yourself. Think of you know, 50 years of therapy in seven days, and you're unpacking a lot of these inherent unconscious patterns that you got from your parents effectively. You're forgiving your parents, you're kind of figuring out how to show up as your truth, true self in the world.

SPEAKER_02

That's beautiful. That's a sorry man.

SPEAKER_03

It's it's a no for me, dog. The one and only time. Yeah, swing and a miss. But I wanted to try a million things that you really can't do when you're building a business. So that was last year. And then honestly, at the end of last year, things all the consulting started to feel a little empty. And I kept a couple projects and some coaching projects, and I love like strategic advisory work. I'll always do that. But I was like, it's time for me to build. What am I gonna build? It's incredible.

SPEAKER_00

And it sounds like so. From hearing, I'm curious, like when you started writing the book. It sounds like up until the very end, like the story was being written. But did you have a different intention for writing the book than it turned out? What the book like I'm curious from the timeline of that.

SPEAKER_03

So during COVID, one of the women, the women that worked for me had written a book. She's a series, she was a writer. She was like, You have such good stories, Helene. And I do. Like, there's some crazy shit in that book that I just like kind of thought everyone was going through. I don't think that they were in retrospect. But she was like, Can we just can we please write the book? And I was like, I don't think that I have a, I don't think I'm a writer. Like, I don't have a book in me. And she said, You do, let's just start telling the story. And when I was on a I had a big today show clip in 2018, 2019, and I had a bunch of agents reach out, being like, When you're ready to write a book, let me know. And I was like, funny, archive. I started talking to my friend Leanne as I walked the boardwalk in Miami multiple mornings per week. It was so cathartic for me to tell the story of City Row and for someone to listen and ask questions. I felt so heard. I felt like the story was bearing witness, and the business was challenging. But the initial idea was let's tell a story from the perspective of a founder that hasn't won yet, but probably will. Because I kind of had this hypo I knew too many founders that when they actually like exited their business, they hated it for whatever reason. It was tainted. They had golden handcuffs, the deal was challenging, whatever it is. And so I was like, oh, cool, let's tell the story before it's over. That could be interesting. And then as shit started getting really insane and we were firing people and the business was crumbling. I had to call my editor and be like, it's a dark book. It's a dark book. I'm pull I'm pulling the proposal. We're going dark. This is nuclear, and this is actually a tragedy. It's gonna be a tragedy story. I'll find a way to make it inspiring, but it's gonna be a tragedy. I hope you're on board, Debbie.

SPEAKER_00

Debbie's favorite call, I'm sure.

SPEAKER_03

Well, Debbie's terrified of me, but that's oh, that's amazing.

SPEAKER_00

So now I know you don't know exactly what the the business is you're building, but there's a newsletter, there's a podcast, and the podcast is kind of related. Like, tell me about all the projects you're working on.

SPEAKER_03

I think they're all related because they're all really talking into the same demographic of mostly women, call it, you know, late 20s into 50s. Like that's that's who I'm talking to. It's people that are curious, people that are interested. And for me, and I think this is again not that different from City Row, the macro is like taking control of your own, like proactive personal health. And in the podcast, it's like a little bit more, you know, more of on probably like the personal growth side of things of like how do you navigate times of uncertainty, which was something that obviously I've been going through not like being part of City Row anymore, like like kind of having to move through that identity of who I was. I love being a City Row founder. Like you met me there, you know? Like it was a pride, something that I wore every single day when I showed up in a room. And so that transition was very interesting for me and challenging. And I love having conversations with people. And we have an episode out, I think this month on the arrival fallacy of like you'll be happy when, right? Like that is such a thing that like plagues this demographic of people. So it's been fun to kind of pick certain topics, have amazing great guests on that are willing to be vulnerable and share when things weren't perfect and how they navigated that uncertainty. I want to normalize that. And so the podcast called Step Into Next definitely is kind of part of this wider ecosystem. The Substack and the newsletter are right now very specific in the GLP1 space. I also have a couple of other projects that are a little bit different, all in like proactive personal health. I think we're in an era where we're all taking control or we can take control of our personal health if we want to. And I think that a lot of our access to information is quickly eclipsing a lot of the professionals in a lot of day-to-day ways.

SPEAKER_00

Makes so much sense. So we talked about in the past building City Row. Like, what do what are the ways you make money now? Are you still doing the advisory? Is it from subscriptions? Like, how is that working?

SPEAKER_03

Yeah, well, I actually have my first two paid subscribers on Substack, which is fantastic. I actually didn't know that you could be get a become a paid subscriber on Substack. So you didn't really have that set up. My friend Vanessa, who's like this unbelievable, like amazing writer. She's like so fantastic. She sent me a whole note. She's like, I love supporting this, it's amazing. And I was like, wow, thanks, Vanessa. Like, I had no idea I could even do this. So that was a beautiful, unexpected moment. But no, there's there's no massive economics coming through that yet. I believe that when you're when you're like pulled to do something, like I spent a lot of time pushing a boulder up a hill at City Row. I'm not doing that again. I'm ready for like true flow and abundance when it comes to building. And right now, this I feel very pulled here. Like I have a feeling that I have an unfair advantage to do something really big in this space. And the Helene today that's able to kind of walk that like path without knowing where it's going is a very different person from 10 years ago or even five years ago building City Row. And I'm confident that like the economics will come to make money. I do strategic advisory work still. I do all kinds of coaching. I particularly love women in general who are facing some kind of pivot in their life. Andor founders are my jam. We're going through a pivot. We got to figure some stuff out. We need to do some easy, quick fundraising support. I'm I'm all in there.

SPEAKER_00

I'm so excited for you. This is such an exciting chapter. Thank you. Yeah, it's been fun. So, something that you talk about in your book, in your story, like you, as a business owner, we have to navigate awkward money conversations all the time. Curious if you've and you, this is probably like in all your deep work around being your true self, like the Hoffman process. This might have supported that. But like, how do you handle awkward money conversations? I feel like, especially for women, like we sometimes shy away from having them and it really can cost us. So curious. Any uh like, yeah, how do you handle those? Actually, they're still awkward.

SPEAKER_03

I I I think they're very awkward. I actually was with a friend and she was interviewing your rich BFF for her for her book tour, I think, and they talked about this, about how to navigate conversations with friends who have different economic abilities for things. Yeah. And the the one of the questions was around, like, you know, you have a friend who like is like, hey, let's go for sushi, sushi all the time. And you're like, I want to do that, I want to see you, but I can't afford the sushi. And she's like, what actually happens is you keep saying no, and that person gets pushed away. And what you really need to do is say, hey, like, how about you come over for pizza instead? And so it's about like five in those moments. That was something that she said that really stuck with me. But I have a ton of awkward conversations. I'm I'm co-throwing a party here in Austin for a friend in a few weeks. And the person I'm throwing the party with has, how do I say this, unlimited funds? Like unlimited funds would love to throw money at everything. Whereas I actually have some time on my hands, and I'm in like more of a fixed budget as I'm in building right now. And also, even if I had a lot of money, I wouldn't be spending as much money as you think on this thing. And so I had to say to her very directly, like, I gotta be honest with you, like, here's where my budget is. And I'm gonna be honest, her first reaction was like kind of tough for me to hear. She was like, Well, I really want this to be special. And I was like, ooh, that hurts, you know? And then we had she ended up coming around and being so generous. She's like, you know what? Like, I'll pay for whatever I need. Like, you you pay whatever you're comfortable with in that kind of a scenario. But it didn't make me feel good. I didn't love it. I stand by my where I where I was on that. But man, does it suck? And man, do we have to get better at it?

SPEAKER_00

Such a good example. How long did you stew in that stress of the budgeting stuff before you brought up the conversation? And did you prepare? Like what I tried to happen via email.

SPEAKER_03

It didn't work. I'd have a phone call and then it all happened via text. And I think I had my friend write the text for me because I was so nervous. And sometimes that's good because you need like a second opinion, like no emotion to be able to come at it. So ask another friend for help and like gut check it to make sure you're not off base in some capacity. But it's really hard. I mean, I I'm I have I'm with a group of people sometimes that I'm just like, I know we have different budgets. And sometimes you have to, you know, state what you can do, what you can't do. And then also what I think is really beautiful is that sometimes you have friends who are like, yeah, I got this, you know, and then just accept, you know, practice receiving, which is also very difficult. But, you know, I have a friend where let's just say our holiday gifts to each other had like a $900 difference in what they were. And I still feel great about what I was able to do.

SPEAKER_00

And do they know, like, have you spoken about money that yours will be lower because of XYZ or just kind of unspoken and known?

SPEAKER_03

So I don't think in my life it's been super necessary for me to be like, hey, money's really tough right now. I think for me that comes out in, yeah, man, like, you know, as I'm building this thing, like it's really important for me to keep X amount of like consulting advisory work. And, you know, that always ebbs and flows, as you know. Right. And so when I'm in a valley, I'm probably just more communicative about it than normal, or it's not even consciously. And this is like you're asking me this. So I'm thinking about it almost for the first time. Right. But I'm more vocal because it's something stressing me out. And I'm trying to be more transparent with my close people on that.

SPEAKER_00

So then they already have that context.

SPEAKER_03

I think so. Yeah. And then obviously, I think work work money conversations are much easier. I find the boundaries very clear, very easy, easier with a lot of practice. Yeah. Oh, I'm sorry, you think you deserve a raise because you need childcare? That's actually not how this works.

unknown

Right.

SPEAKER_03

Feel free to get another job.

SPEAKER_00

And the and also too, what's cool about showing the friend, right? When you had her help you draft or she drafted the text, is like then you're now having a conversation with that friend that maybe you otherwise wouldn't have. Like you're opening that area of your life. Yes, totally. And you're you're you're being vulnerable.

SPEAKER_02

Mm-hmm.

SPEAKER_00

I know you're in New York City and Austin. Like, what looks different about life financially for you in Austin than in New York?

SPEAKER_03

Okay. Austin's very cheap. Is it? I pay about $3,000 a month for a beautiful one bedroom and like one of the nicest buildings in town.

SPEAKER_02

Wow.

SPEAKER_03

It's it's it's unattainable. And it's one of the reasons I chose to live in Austin, at least for just kind of this in interim period, is that I kind of outgrew the ability to live in a studio or a one bedroom in New York City that was like kind of a piece of shit. And I needed, I needed, I needed greenery, I needed space, I needed a slightly easier life during this like recovery from burnout moment. And so Austin's really, really good for that. And for some reason in New York, like every time I leave my apartment, it feels like I'm spending $500. And I feel like that doesn't happen as often in Austin. Don't get me wrong, like there are plenty of ways to spend money anywhere you want, but it it's a slightly more economic way of living. And one of my other big hacks that is how I do the New York Austin thing is because my parents have an apartment in New York that they vacate in the summer. So you come in the summer.

unknown

Yeah.

SPEAKER_03

I'll pop up like every eight weeks or so, ideally when they're traveling and they have a second bedroom so we can live there together for a couple of days. But they go to their lake house in the summer, and so I move into the apartment. So I didn't realize they lived here. Yeah, so they're on East 23rd, and then they have a house in the Poconos.

SPEAKER_00

Oh, that's wonderful. Okay, so that helps. Then you have a place to stay for your buy, and then you rent out your place.

SPEAKER_03

If I can. Boston in the summer. It's a tough sell. Okay.

SPEAKER_00

So more so it during South by.

SPEAKER_03

Totally. So that's one, that's my big habit on how I'm by coastal or like a young snowbird.

SPEAKER_00

I love it. What's something about your finances people would never guess?

SPEAKER_03

I don't know. I actually don't think I I want to say like I don't think I spend as much money as as people think I do, but that's probably not the case.

SPEAKER_00

No, because I do think like I, of course, follow you. And I, you know, like people live big, it's like you look like you're living a big, fabulous life. So I could see that.

SPEAKER_03

I yeah, I do think I'm like pretty intentional about spending money. And I like, I always think like, what's the phrase, oh my god, I'm gonna butcher it and you're gonna be like Elaine, you can never come on my podcast again.

unknown

Never.

SPEAKER_03

Pennywise pound foolish. Is that it? Yes. Like I really do, I do think about dollars. Like, I'm actually not great at the grocery store. I love a bougie grocery store. Like, that's one of my biggest like splurges. I like to go to Whole Foods or here, there's a place called Central Market, and I like to just not look at anything. Like, that's my luxury that I can get myself. Like, that feels like I'm winning. But, you know, I fly economy, which is also something that a lot of people in my world like could never fathom. But whenever possible, I like to remind myself that that's something that I could get in the future and that I can still handle economy. And I like to always do that. I've even done that on some international flights, and I will continue to. I'm very scrappy with points. I'm very good at credit card point management. I will like, I will like remind everyone, hey guys, it's the end of the Amex Platinum. It's time to get your Lululemon and all your resi discounts if you haven't already.

SPEAKER_00

That's very helpful, friend. That's a very helpful reminder.

SPEAKER_03

I'm a good friend. Yeah.

SPEAKER_00

So we talked a lot about affording like your current life, but what are you working towards affording next?

SPEAKER_03

So I did an exercise a couple of years ago of like, where does the money flow? And then when you like need money, money flows. I think for me, like I'm really looking forward to kind of rebuilding a nest egg that I depleted during my city row time. I think that that's, you know, I feel fortunate enough that I'm able to live my day-to-day lifestyle. It's planning for the like long future and starting to kind of build that wealth that I wasn't that wasn't afforded to me during the City Row time. And that as an entrepreneur is just like, it's a very challenging thing to do. And so that's my goal for this next tenure is to rebuild that nest egg as big as possible and to hustle for it. It's not necessarily that I want to buy X, Y, and Z or do these things. I'd love to invest even more in my health and wellness. There's like, I think there's more and more things that are out of pocket, not covered by insurance health and wellness things that are becoming on my radar that I think I'd like to spend some more and invest in.

SPEAKER_00

What are those? Can you share some of them?

SPEAKER_03

Like there's like, for instance, like there's this like the PRNO machine, this like a $5,000 like full body MRI, you know? Like that's a real expense. And and more, more things like that. There's tons of like other like blood work and screenings, and you know, haven't even done that much work into figuring out which ones are worth it and which ones aren't, but more like proactive personal health. And then, you know, finding a way to get back to New York in a more like intentional way and you know, maybe have my own place somewhere.

SPEAKER_00

Well, thank you so much. Congratulations on everything. I'm so inspired by the way you found your next venture, bigger story. Like you are so scrappy and brilliant. So thank you so much for this behind-the-scenes look into how you ran your businesses, how you afford those GLP ones, where can everyone find you and support your work?

SPEAKER_03

Thank you, Ashley. I am Helene Knapp on LinkedIn, Instagram, and my sub stacks are pretty easy to find as well through those channels.

SPEAKER_00

Amazing. I'll link to them all. Go follow Helene.

SPEAKER_03

Thank you.

SPEAKER_00

Thank you. Thank you so much for listening to How Do You Afford This? If you love this inside look into how people are actually affording their lives, follow and subscribe wherever you get your podcasts. We have new episodes dropping every week, and trust me, you do not want to miss them. And if you're enjoying the show, it would mean the world to me if you left a review. It just takes a minute, and it helps more people find the show, which helps me on my mission to make crafting a wealthy life more accessible, more transparent, and a whole lot more fun. See you next week.