Sex sells, but does it raise money?

By Jason Yeh
December 8, 2020
Listen on Apple Podcasts

Episode Summary

Investors like patterns. They’re either explicitly or subconsciously motivated to back businesses that look, sound, or feel familiar and comfortable. That’s why Isharna Walsh, founder of sexual wellness app Coral, had such a daunting task. For her, raising venture capital meant guiding investors through the uncomfortable task of talking about their sex lives and convincing them to back an unfamiliar profile, a minority woman with no ivy league degrees.

Topics Discussed

  • Isharna discusses her background and the moment she had the idea for Coral [3:27]
  • Did Isharna know she needed Coral to be a venture-backed business? [5:19]
  • Describing what Coral is its opportunity to impact the world [9:23]
  • How Isharna tried her best to make her story match more patterns for investors [13:06]
  • Challenges raising money for a business that is risque as a woman [14:52]
  • Talking about the crazy statistics around who controls venture capital dollars in the United States [18:19]
  • Her realization around who would understand her business and be open to funding it [20:55]
  • Meeting her lead investor [22:12]
  • A really crappy meeting [23:44]
  • Describing the moment she found out she found out someone would lead her round [29:51]
  • An important message for underrepresented founders [37:34]
  • The blooper reel that comes from trying to get investors to put money into a company focused on sex [40:08]
  • Debrief with producer Olivia focused on how important pattern matching is to investors [43:53]

Resources Mentioned


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Isharna Walsh
Jason Yeh (host)
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Sex sells, but does it raise money?

Investors like patterns. They’re either explicitly or subconsciously motivated to back businesses that look, sound, or feel familiar and comfortable. That’s why Isharna Walsh, founder of sexual wellness app Coral, had such a daunting task. For her, raising venture capital meant guiding investors through the uncomfortable task of talking about their sex lives and convincing them to back an unfamiliar profile, a minority woman with no ivy league degrees.

Episode Transcript

Isharna: [00:00:00] And I just went home andcried. Like I literally just went home and cried and cried and cried. And I waslike, I don't know if I can keep doing this. And then of course you just likewake up the next day and keep doing it.

Jason(host): [00:00:18]This is Funded. A show where founders who raised millions in venture capitalshare the gritty side of what it actually took to get that money in the bank.I'm Jason Yeh, your host. Not too long ago, I was trying to get my ideasfunded. And once upon a time, I was a VC listening to founders pitch me formoney.

That founderyou heard at the top is Isharna Walsh. Today, she's sitting on millions ininvestment, but back then she was crying because no one wanted to dive intouncharted waters with her. The thing is we all know those water waters well, wejust think they're taboo

I'm talkingabout sex, and that's what she did. She went around to VC after VC talkingabout sex. Until she found a partner willing to back her idea, an app forsexual self-improvement. That app Coral has impressively attracted two roundsof funding, and she got there by getting in the room with mostly white men todiscuss issues in the bedroom.

She saysshe's always been kind of an ear for people which goes back to her childhoodwhen she would listen to our friends for hours on the phone.

Isharna: [00:01:33] I think I've always beensomeone who's really interested in other people and how they feel. So, um, mymom used to say, you know, she's a Sri Lankan mother, very much obsessed withme getting good grades and doing what I should do professionally. Um, I wasmeant to be sort of, you know, I was a bit, I was meant to be a lawyer or adoctor.

Um, ofcourse, as you probably can relate to, um, eh, and you know, I'd spend hours. Iwas on the phone to my friends talking about their feelings, um, and sort ofcounseling people through various things. So I think that was really consistentwith what I'm doing now as a business.

Jason(host): [00:02:14]What about, you know, were you comfortable talking with people like in front ofpeople?

Isharna: [00:02:17] I don't think I've, I don'tthink I've ever been comfortable public speaking. So I've never beencomfortable in situations where it's one to many where sort of I'm the centerof attention, um, where it's not a dialogue. Um, anything where it's amonologue, I've always felt like pretty pretty unsafe.

Jason(host): [00:02:38]What about your relationship with asking for things, asking for favors andmaybe in some future state... asking for money?

Isharna: [00:02:47] Yeah. That, um, that'ssomething I definitely had to develop. So that was not something that camenaturally, um, at all. Yeah.

Jason(host): [00:02:55]That that's, it's always interesting to hear like, Where people came from andthe things that feel super unnatural, um, when you're going around raisingmillions of dollars. So, you know, Coral is, is this something you've thoughtabout for a while or, you know, did it come out, um, because you, you, you readsome book about business opportunities and this is the one.

Isharna: [00:03:16] Yeah, absolutely not. Um,yeah, so I, I think to start a business that has a positive impact for a reallylong time. So, you know, um, when I was at university, I studied economics andlaw. I grew up in Canberra, which is the capital of Australia and it's reallynot a place that fosters entrepreneurship or innovation. It's about government.Um, I always thought I would work for government or for a nonprofit as a lawyer.Um, and I went into those jobs after university. So I, um, I was working at alaw firm. I worked in economic policy for the Australian prime minister. Um,and I realized pretty quickly that that wasn't the way to achieve social impactas quickly as I would have liked.

And so, theidea of somehow combining the profit incentive with social good was reallyappealing to me. Um, but it took me a long time to figure out what that thingwas. And when I had the idea for Coral, I was actually sitting at my kitchentable ideating as I, I do all the time and have done for many years about likedifferent types of businesses I might want to start.

And, uh, hadthe idea for Coral. And it was like a light bulb moment, like all the cogs inmy brain sort of synced. And I was like, Oh, okay. That's it. And I knewstraight away, like, and, and from that moment, I haven't had any doubt thatthis is what I meant to be doing. And that the vision I have for this companyis, is what I want to create.

Jason(host): [00:04:55] Imean, that's, that's an amazing way to hear someone describe their startup. Um,me as an investor may as an adviser, that's, that's. Probably my number onefilter of, of, of what I want to see. Um, but when you think about like finallyrealizing that this is what you wanted to do, Did you know, it would be aventure-backed business or was that something that you had to like discover foryourself?

Isharna: [00:05:19] Um, so I used to be aventure capitalist. I was actually working as a venture capitalist and I hadthis idea and I, um, never wanted to start a venture backed business because ofthat. I kind of knew, um, how hard it was and how generally the outcomes ofbinary. Right. They're either incredibly successful or failure and you, becauseyou're pushing so hard to reach that extreme success. And I know, you know,there are parts of, on that, on that journey, if you're lucky and you get agood acquisition offer, but generally it's that binary outcome.

And so Inever thought, especially given my personal priorities around wellness and andrelationships and family and all that sort of stuff, um, that I would want tostart a venture-backed business. So when I had this idea, I knew it was aventure-backed business, and I knew that venture capital would allow me toreach that scalable social impact of potentially impacting millions of people'slives.

And so, youknow, I was 29 I think, and I was just like, you know what, let's give this ared hot go. I can run at it for three to five years if I can do it now before Ihave kids. Um, and this is really the only window where I'm likely to do this.So, so let's go. And so that's why I made the decision to go for it.

Jason(host): [00:06:52]It's amazing. I mean, uh, we've had other conversations where we bring to light.Um, one of the things great VCs do, which is they actually try to convincepeople not to take venture capital. If it's not for them, you know, you don'ttake venture capital. And so you, having a light bulb moment with a passion,um, and all the inside knowledge of why you, shouldn't, why somebody shouldn'ttake venture capital, right, decide to go do it. Yeah.

Um, veryinteresting transition to me then asking you, once you realized that you, youwanted to do this one, that it was a passion and then two that like. You wantedit to be a venture-backed business to have as much impact as possible that yourmind immediately go to how difficult it would be knowing what you know aboutthe industry.

I don't meanto lead the witness, but I am curious.

Isharna: [00:07:47] It's funny because I just,I reached this point like a year, um, maybe even more than a year and maybe itwas even after I raised my seed round of like, I'm crazy. Like this is crazy.But at the time the, the, I like the idea and like what would doing just feelsright. So obvious and so right.

And like sucha huge opportunity. It's such great market timing that I was more like, whywouldn't people give me money? And I didn't think about like, exactly how hardit was going to be. And I think if I had been, maybe I would've felt lessexcited, but, you know, here we are!

Jason(host): [00:08:28]Totally, totally. And so at this point, I mean, we can. We can give a happy...tease a happy ending. You have raised, um, two rounds of funding. Um, but as Ithink about the methods and the approaches that VCs use to evaluating, um,potential opportunities, you know, it does make me wonder what that journey waslike. So I wonder if you could kind of rewind back and think about, can youshare how much you ended up raising in your seed round?

Isharna: [00:09:00] Um, yeah, so, so we raiseda small pre-seed and then a seed round. Um, and so in total we've raised, um, abit over 3.2 million.

Jason(host): [00:09:10]Talk me through, especially preparing for this last raise, um, what the storywas, you know, what you thought you had and how you would actually convincepeople that this was an opportunity.

Isharna: [00:09:23] Yeah. So, I mean,essentially we're creating. You're trusted guide to a happier, healthier, intimatelife. So we want to be your trusted source of support and inspiration for allthings relating to your sex life. And the way we do that is through, um,learning, teaching you, um, sex-positive pleasure-focused sex ed, the stuffthat you wish, should be taught, but we never are.

Um, Talking.So community providing a safe, positive place where people share morevulnerably, what they're experiencing, which is incredibly normalizing andvalidating because we're not having those conversations publicly. And thenplaying. So guided exercises to help you experience something differently tohow you have before.

Um, so wereally want to become a tool for you to explore the, the extent of what isavailable for you pleasure wise connection wise, intimacy wise, um, eitheralone or with a partner. Um, the way that can turn into a billion dollarbusiness is manifold, right? And the one that's the most obvious is we can lookat other wellness companies like a Headspace or Calm that particularly Calmbeing incredibly successful just with the simple annual subscription contentmodel where people use it as a tool for their mental health and other areas,whether that be anxiety and depression or sleep assistance. Um, so that's theone that's the most straightforward pattern matching.

Um, we havean interesting angle from a data perspective as well because we learn so muchabout our uses. Um, in the way that they engage with the platform. Um, and sothat data set is really unique and were very adamant. Like that's not somethingwe're going to sell, but I think there's things that we can do with that as acompany.

Um, privacyis super important, obviously. So that's kind of the overall broad. Broad brushstory that I went in with

Jason(host): [00:11:37]Coming up, how that story initially flopped and got some much needed help from,well, baby-making.

Most of mydays, one-on-one with founders, helping them understand strategies that make adifference in fundraising. One super important tip. I always stress withfounders is to make sure they send their decks and materials using a documentsharing tool. And for that, I always recommend DocSend. DocSend, lets you knowwhat's happening with your deck after you send it along with real-timeanalytics and notifications.

Did the VCsactually open it? What slides did they spend most time on? And if you think it gotshared with the wrong people or maybe you made a mistake and sent it tooquickly. DocSend lets you control access and make updates to content even aftersending. Sign up for a free two week trial at That's D O CS E N

If youhaven't figured it out, uh, Isharna is the first of something. She's goingwhere no one has gone before, and that can excite some investors. But notbefore turning a lot of them off.

I wonder ifyou could talk a little bit about, um, you know, what you ran up against when,um, starting to pitch your story because. When I think about the easiest thingsand like sort of the cheats that investors use yes. Is around things that theyunderstand or that they know. It's why we have multiple billion dollar valuationsfor note taking apps of all things. Um, and yeah, you just mentioned patternmatching, which, you know, we can lightly describe as, um, investorsessentially investing in what they've seen before, what they've seen besuccessful before. And so maybe you can tell us a little bit about, um, youknow, how difficult that was or some of the difficult times around that.

Isharna: [00:13:54] Um, so for us, I actuallyprobably about halfway through my fundraising process started saying, okay,it's like, as if Calm and Netflix had a baby and that baby was all about sex.Just to like...

Jason(host): [00:14:12]instagram for cats. Like, I use that as a joke, but you know, that's, yourminds are pretty simple. You kind of have to connect the dots for them.

Isharna: [00:14:21] Yeah. Yeah. So that wasdefinitely one. Um, and then there's obviously all the stuff around, like, youknow, I'm a young woman walking into a room talking about sex, so that's awhole other thing as

Jason(host): [00:14:36]well.

Well, yeah, Imean, feel free to steer us in a different direction, but, um, you know, I, Iactually work with, um, a number of underrepresented founders, women, people ofcolor, um, and everyone has a different perspective on what that feels like.

Um, It soundsvery intense what you had to do given obviously you're a woman, but that thetopic and the sort of underlying content of your company in particular, it canmake people uncomfortable. Do you feel like you were surprised at how openpeople were or was it, um, you have bad stories?

Isharna: [00:15:12] [Laughter] As you weresaying that I was like, no, it's probably exactly what I would've expected.

Um, that isfunny. I, so, okay. So. You know, I actually probably feel like I experiencedmore issues as an investor, um, in terms of like sexual harassment type stuffthan I have as a founder, that might be the timing of my experiences because ofthe me too kind of conversation, I think put a lot of investors on their bestbehavior, so that might've been part of it.

Um, but Ialso think in some ways, Having, um, you know, I, you know, you don't get intoa meeting unless someone's seeing your pitch deck, so they already know whatI'm talking about. Um, but I also think having such an explicit subject matteractually disarmed that kind of, um, dynamic from being, being a problem, um,just in terms of harassment, but then.

But thenthere's being a woman and not a white woman either. And I'm not from aprivileged background. Like I don't tick any of those boxes. Um, and then, andthen also having to navigate the nuances of the sensitivity of the investor Iwas pitching to during a pitch about sexuality was quite difficult because it'salso, you know, I think a lot of female investors, I'm sorry, entrepreneurs,um, pitching a product for females, um, or, you know, like women purchasing aproduct for women. Um, Have the issue that the investor doesn't understand theproblem. But when I go into a pitch and I talk about, um, you know, themajority of causes of erectile dysfunction being psychological, and thereforethis is an incredibly powerful and huge product and a huge market to help dealwith an issue that affects, you know, over 40% of men at some point, um, That'sreally interesting from an investor standpoint, if you think about it, but it'salso like...

Jason(host): [00:17:22] IfI agree that's going to be embarrassing if I...

Isharna: [00:17:25] Right.

Jason(host): [00:17:27]No. Wow. That is a mind field for you to navigate.

Isharna: [00:17:31] Yeah.

Jason (host):[00:17:32] Oh, maybe.Why don't, why don't you talk about that a little bit more like, uh, because Ido obviously, like, you know, you have a very unique business, um, But I do runinto a lot of founders who are, you know, come from these backgrounds and needto navigate this idea of like, sort of finding common ground with the personthat they're talking to.

Uh, and thenalso have a product that. Likely the, the investor doesn't know, you know, sohow did you think about that? How did you get people comfortable, um, talkingabout these things and lead them along essentially?

Isharna: [00:18:07] Yeah, so, so, you know, onething was that I had been a venture capitalist and, and, you know, I got thatrole, um, really out of left field.

Like, youknow, I, you know, when I joined the industry, it was 95% men. Um, and, and 40%of people are from Harvard and Stanford, which is also a statistic that isn'tspoken about very often. But I find just as mindblowing, because essentiallyyou have all of this investment capital being controlled by graduates from thetwo most prestigious... TWO. Two most prestigious universities in the country.

Um, when youthink about the level of privilege, it requires to go to that. That kind of,um, school it's kind of astonishing. So I'd already learned a bit about likethe talk and the walk from having been an investor myself and being exposed tothat environment ahead of time. So one way, depending on the investor that Ihandled, it was very much, um, focusing on the business on the business ratherthan the emotionality.

So, you know,this is a huge industry. It's a massive problem. No, one's attacking it the waythat we are, we have this opportunity to become a market leader. Um, all ofthose things like. Really pushing it down that, that path I think, um, was oneway I navigated it. And then the other was, um, you know, I'm very comfortabletalking about sex and sexuality myself.

And so mycomfort with the subject matter often would put the investor at ease. Um, Imean, I make a joke, like I definitely know intimate details about. Manyinvestors sex lives after, after having pitched them because they'recomfortable, you know, certain, certain investors are comfortable sort of openand sharing their experiences.

Or, you know,when I, when I explain what we're trying to do, being like, Oh yeah, you know,like I'm of an age where like, many of my friends are struggling with thesethings and my partner and I struggled with these things and I can totally seehow. This product would be really helpful. Um, so yeah, it depends on the vibein the room a bit as well.

Jason(host): [00:20:24]Well, I I'm glad you brought that up because you know, I'm curious, did youhave to pitch, uh, a lot of VCs to find who would eventually lead you around?Okay. So, yeah, cause you, you know, you did mention. You know, you got someinvestors to open up about their sex lives, which to me was like, wow, that'skind of crazy.

And Iwouldn't have expected that, um, was, was your lead investor, one of those investorswho was very open.

Isharna: [00:20:54] Yeah. So, and that's thething. And I think that was the other thing I realized through this process.And it's part of like, just, it's going to be my journey and I just have to beokay with that is like, Not everyone's going to get this.

So forexample, like I think in a high, like consensus driven foam, where a partnerhas to go in and pitch Coral to their partner group, it is going to be wayharder because that investor has to come in and be like, Hey, you know what Ithink is awesome. A product to help people have better sex. And like intimacyis a real problem.

And this is areally interesting tool for navigating a huge market that is sex. Like a lot ofinvestors are not going to be willing to use their social capital on thatissue. Um, and they're going to be too worried about the way it makesthemselves look. And, and then also there's going to be a lot of all the peoplein that room that might have reactions to.

What I'mtrying to do. So like our lead for our seed just got it. Like, he was justlike, Oh my God, I've been thinking about this vertical life. I've been lookingfor something in this space. Your approach makes total sense. Like I'm ahundred percent on board. That's awesome. Yeah.

Jason(host): [00:22:12]Yeah. I, the up question is where in your process?

You know,rough, rough numbers, broad strokes. Did you meet him like, was it your firstintroduction? Like

Isharna: [00:22:23] So far in, and actually Ihad been introduced to a different partner at the same fund, but she doesn'tusually look at consumer apps. Um, so she was like intrigued, but it was rightbefore summer. And then I didn't follow up because I was told never to followup with someone who else to follow up with me, which I think is actually true.

Cause ifsomeone's really excited, then they will follow up. Um, and so, and thensomeone else was like, Oh no, this is the person you need to speak to at thesame fund, um, later in the process. And so,

Jason(host): [00:22:58] Noway...

Isharna: [00:22:58] Yeah. And so then I cameconnection easily. Right, right. Wow. Yeah. I mean,

Jason(host): [00:23:04] Noso the reason I ask you actually is... that means, you know, 20 first meetingsin your, your you know, you're striking out left and right. Um, what did thatfeel like? What was going through your mind before you, you know, before youactually met this one investor?

Isharna: [00:23:22] Yes. I mean, it was a slog.It was a slog. I don't think, I think so many women struggle to raise money inthe sexuality space. And I was probably like, at least two months in. And itwas probably more than 20 meetings, frankly. Um, and it's so weird, Jason, so Inever lost conviction that I would raise money, but I was exhausted and like, Iremember I had this one clique, like probably the lowest point of thatfundraise I had. Um, I was in San Francisco for like this sixth week in a rowwhere I'd like gotten on a fight, flown up to the bay, um, And I was meant togo for a surf with my friends on a Saturday. And I was like, so looking forwardto just like, not thinking about Coral and fundraising, and this investor waslike, Oh, I can meet you tomorrow at this cafe. And I was like, Oh fuck. Youknow, it's Saturday. Like I should do it.

Um, so I wentand met him and, and it was. One of those meetings where I was like, why didyou even take this meeting? Like I walked in and he was like asking me my likeDAU, WAU, MAU. I was like, I haven't even launched yet. And you know that,like, I've got a beta product. It has about 8,000 users. And actually, youknow, our weekly averages were apparently about on par with Headspace on a betaproduct built by two people.

Like, like Iwas like, This is actually pretty good. Um, and he just drilled me on metrics andI was like, what are we doing here? Like, this is a seed round, right? Like,and I just went home and cried. Like I literally just went home and cried andcried and cried. And I was like, I dunno if I can keep doing this.

And then ofcourse you just like... wake up the next day and keep doing it [ Laughter]

Jason(host): [00:25:29]So, I mean, I mean, I don't know if we can say obviously for you or whatever,but, um, from my vantage point, having spent a lot of time with founders it's,I mean, that is not an unusual situation to go through. Um, did you feelyourself over those 20 meetings?

Being swayedand someone saying, you know, Isharna, uh, do you really want to focus on fullysex? Maybe it can be more like meditation and mental. I mean, did you startgetting buffeted by people's opinions or, or were you pretty strong and, and,and like sort of sticking to your guns?

Isharna: [00:26:05] No, I'm I it's it's again,this is weird.

And I think,um, I don't know. I don't know what it is like to be another entrepreneurial orlike, this is my first venture startup. So like, I've been so clear in ourvision and the whole time and like, through the whole, even as we, it, it waslike, and sometimes I look at a little bit anxious that I'm delusional, like,or like, That it doesn't make sense that I've got this much conviction, buteven through the seed round and it taking a while to raise money, it was morejust like these people are idiots and I need to find the right one more thanlike, am I doing the right thing?

Which maybecrazy, but,

Jason(host): [00:26:52]uh, I'll say this. I almost use the exact same words when I talk toentrepreneurs. So you're you've, you've got it down. Um, Fast forward. So it's,it's been like a difficult 21st meetings. No, one's really getting it. But youdid find...

Isharna: [00:27:08] That was what was reallyhard. So a lot of people got it and I had a lot of cash, soft circled, but nolead.

So I actuallyhad the whole round, like I had enough capital committed, but they was, theywere, no one was willing to lead it. And I, again, I don't know if that was.Being a woman being, uh, not like, not like patern matched founder, uh thesubject matter. Like, I don't know what it was, but like all these people werewilling to write me a check.

Just no onewas willing to like...lead it

Jason(host): [00:27:40]Yeah. I mean, I think the, the tough thing too is it's so easy for someone totell you. Oh yeah. Like I'll, I'll invest as long as you go get a lead.

Isharna: [00:27:49] It's like, they've got likehalf conviction and you're like, cool. Can someone just run me a term sheet?And then this is done

Jason(host): [00:28:00]After the break, what it felt like when she finally got that term sheet inhand.

In my worldas an entrepreneur, data is so important. I check dashboards all the time tomake sure decisions I make are producing the best results for my company. It'skind of why I've always been so frustrated with personal health where my weightand blood pressure are the only metrics available. Because I got really luckywith genes, I could have pizza and a beer or salad and water. And not see anydifference. That's why I've been all over a red hot startup called Levels.

Levels is thefirst bio-wearable that provides real time data on how, what you eat impactsyour health. So now the same way I can see how tweaks to my website affectconversion rates immediately. I can see how that taco I had for lunch isaffecting my health all in real time.

Levelsliterally has a 60,000 person waiting list for their early access program,which is why it's taken me so long to get one. But I'm excited to share thatthey've offered listeners of Funded a chance to skip the line. To get earlyaccess, just visit

Okay. Back tothe show.

Everyoneremembers where they were when they got their first term sheet. It's like yourfirst kiss and hitting a game winning shot all wrapped into one. It's justsomething you don't forget. And with Isharna, it was no exception.

Do youremember finding out that they were going to invest? Do you remember where youwere?

Isharna: [00:29:46] Yes. I remember exactlywhere I was actually at a friend's friend's bachelorette party in Palm Springs,I think were no, we were in Arizona. We were in Arizona, Phoenix, and we'regoing to Sedona and I was sitting at this cafe. Um, and I remember, yeah, Iremember the phone call and I think, I, I think I'd probably cry then too.

And then Icalled my mom,

Jason(host): [00:30:18]You know, unfortunately this is a podcast, not a log or what do you call them?But I sometimes just like asking the question, because when you see someone'swhen a founder's face go. So like, thinking about that time, it's just likethis. This look of pure joy because it is this, I mean, I remember my ownexperience of like, so much anxiety around whether or not it's going to happen.

And then itkind of happens.

Isharna: [00:30:44] I remember trying toexplain to my friends, cause I was at a wedding, um, like a couple months, likein the middle of the fundraise call a couple months earlier. And, and peoplebeing like, Oh, how are you? And I was like, Oh yeah, like, Pretty stressed,like, you know, it's bang on.

And myAustralian friends, like this is so I didn't know what a venture capitalist wastill I was 26. And so like for my friends, it's like such a weird context. Likethey don't really get it. Um, but I tried to explain it to them and I was like,so I am basically having like four intense job interviews... a day, a couple ofdays, a week for weeks on end....

uh, not toget a new job, but to just keep my job and not just to get my job, but also tokeep my team's jobs. And they were like, Oh yeah, like that sounds hard. I waslike, yeah,

Jason(host): [00:31:44]I've, I've never heard it described like that, but it's so good. Um, well Iactually, you know, I wasn't planning on asking you about this, but in order totwist it to something fun, which I always love seeing, um, T tell me what itwas like after you got the term sheet and now you're in the driver's seat.

So yeah, I'massuming you raised X million dollars and your lead decided to take, call it 60to 70% of it. Right. Do you want to talk me through that a little bit?

Isharna: [00:32:13] Yeah. Well, I think that'sthe other thing that, um, people, I mean, I definitely underestimated, I don'tknow if everyone underestimates this, but just like the sheer volume of stuffthat you're meant to do as a founder that you have literally no idea how to doso.

Like even asa VC, I had never like. I'd never actually gone through the full deal processwith an entrepreneur. Um, like, you know, our lawyers handled that in my, likeI had partners at the fund, so they like did the sort of day-to-day back andforth with them found. And so, um, it was just like a bit like, I don't knowwhat I meant to do now.

Like, okay.So I have a term sheet, like my lawyers, I was like asking my lawyers, like,what am I do? And so like, I had to go back to those other people who hadoffered cash and then round that up and then all that coordination and liketrying to close. I didn't, I didn't quite realize there's also a skill set inlike closing a commitment after it's kind of what you mentioned, like the halfcommitment, like yeah.

I'll writeyou a check and then like, actually having to go back to those people and belike, okay, but now you have to write me a check. So all that stuff and likecorralling all that. Um, but then the craziest moment, I guess, is when it, allthe wires come in and then you're like, Oh my God, okay. Now I have a bankaccount with millions of dollars in it.

And, and Imeant to do something like that. Like now I have to do do something.

Jason(host): [00:33:34]Now the thing that I said I'd do. I got to go do that.

Isharna: [00:33:38] That's another thing too.Like talking to my friend, like again, my friends are like, so like, how doesit work now? Do you like get up? Give them a budget and they give you somemoney and I'm like, no, I literally have a bank account with millions of dollarsin it.

Here is thecredit card, like

Jason(host): [00:33:53]That's wild. So you also touched on one other thing I was curious about, um,your ex VC's have a much easier time figuring out the details around this, butas you mentioned, and you know, I, I spent years as a VC as well, but didn'treally learn the details until I got into it.

Um, How didyou, how did you navigate the strategies and the skill sets to like, do thethings that are required to close people out and actually get people to invest?

Isharna: [00:34:25] Honestly, I have no ideaand I don't think I'm particularly good at it. And like, I think I need tolearn. Frankly. Like, I, I mean, I think I, I got through our seed with like alot of determination and like pretty compelling story.

Um, I'm likevery comfortable and articulate when like one-on-one particularly with, withpeople. So like, I think that got me through, could I have been better at it?Like. Absolutely. No doubt. Do I think I need to practice before I raise mynext round? Yeah, probably should invest the time and effort in getting somesort of a coach or mentor to help me get better at particularly selling

Jason(host): [00:35:08]Well, on that point, what do you think some of your biggest mistakes were thatlooking back on it?

Isharna: [00:35:14] This is an awful thing tosay. But I'll say it. Um, I I'm like a super honest, super transparent person.Like it's, it's almost like there's no real filter most of the time. And Idon't. I think that's really good in life. Like I think that, um, it means thatI build really quality, meaningful relationships.

Um, and likeinvestors will tell you that that's good in fundraising, but I don't think it'sgood. I think, I think you need to be very strategic in the way that you havethese conversations and like what information you disclose versus not, um, howyou like numbers can tell so many different stories. So it's like, I think,yeah, I think I was a bit naive about like, like of course this just all makesso much sense.

Of coursepeople are gonna invest in it. Like I think I, yeah, I think there's somethingabout like strategy and psychology and sort of being very conscious about howyou come across and how you paint a picture. Um, so yeah.

Jason(host): [00:36:30]It's interesting to hear you say that because you were a VC. I mean, what, whatI tell people about the fundraising process that's difficult is that it, um, itis like a version of sales, right?

And you werejust talking about getting better at sales and in traditional sales, theyreally teach you. You need to get in the mind of the buyer. Like you need toknow why a certain person needs to buy your product so that when you sell it tothem, you can play on the things that are important. And, um, Yeah.

I mean, it's,it is so difficult. Um, Even for an ex VC that has no filter...

Well, closecousin to that, you know, you have obviously learned a lot through two roundsof fundraising, uh, and everyone learns with practice, but what is, you know,what is one or two lessons that you've learned that you would either tell ayounger version of yourself or when other founders are asking you for advice?

Like, whatare some. Important things you, you share with them?

Isharna: [00:37:28] Um, one thing I would sayto other minority founders, particularly, and founders who don't fit the mold,which I wish I had known going into my, particularly my last round was it'sjust going to be harder for you and. That's just the way it is and it sucks andthat's not how the world should be, and we're going to change the world.

But until wechange the world, it's just the way that it is. And so just accept that. Like Ithink, I think that's one thing I wish, like if I had gone in with theexpectation that like this might just take me a bit longer. This might just bea bit harder. I might get more nos. I might get a low evaluation and like, justaccepting that that's just the status quo right now, because obviously I'mangry about that and I find it frustrating and I want to change it, but we can'tchange it right now.

We can changeit over time and we will. Um, but that I think was one big, one big one that Iwish I could have told myself earlier.

And I thinkthe other thing would be around. Um, I mean, I mean maybe what I justmentioned, like being more strategic and thinking carefully about how you can.Make it as easy as possible for an investor to say yes.

Jason(host): [00:38:55] Sogreat. I meant that, um, I've given that first piece of advice before, and itdoesn't always land the way you want it to be. Which is, it is tough love. Ithink it's tough love, right? Like you, you want people to succeed and you wantthem to know the realities of the world and that we'll all, we're all trying tochange it.

But, um,where we are right now is a difficult position and it's going to require morehonestly, like for you Isharna and other people out there, it's like the factthat you've. Push through this. I mean, you're, you're a part of the change. Ithink other people will be part of the change. So, um, yeah. Kudos to you.

Isharna: [00:39:35] Thank you. I reallyappreciate that. Yeah.

Jason(host): [00:39:38]Um, I've, I've been so excited to follow your career and when you started this,I, you know, kind of knew that this would be an awesome journey for you. Soit's awesome to be able to sit down and hear more of that, this story. I, I,uh, want to ask you some fun things about.

The wholeprocess and things that you've gone through, but obviously, yeah. Right. Maybenot obviously, but what I'm hoping for is that there is a blooper reel in yourhead about the stuff that has come up for like people needing to do diligenceon your part.

Isharna: [00:40:10] I would kind of joke aboutlike how many times can I make an investor blush?

Like, youknow, we're sitting in like a fancy boardroom in a fund in San Francisco. Andlike, I'm like, blah, blah, blah, blah, blah, ORGASM, blah, blah, blah,THREESOME, blah, blah, blah, blah, blah, SEXUAL NOVELTY. I like just sittingthere and like the colors slowly going up their face.

Jason(host): [00:40:34] Ohman. When, when you go out to raise your next round one, I hope you tell me.

So I know incase I have a chance at your round and then two... I want to create a custombingo card for you where it's like, if you can have these things happen duringa pitch.

Isharna: [00:40:51] Yeah. Funny. Yeah. I mean,cause I, that was a part of my calibration process was also like, cause it'sreally difficult. Cause I think also people have all these questions, but theydon't ask them because they feel uncomfortable.

Like, likehow do you actually make sex better? Like even just that, like we have to gointo data, right? Like a lot of people suffer from like all of these sexualdysfunctions or issues, but also a lot of people just want to have better sexand like pleasure. When you stop talking about like experiencing more orgasmsor, um, like more reliable erections or like, you know, mindfulness for desire.

Um, we haveguided blowjobs, guided vulva massage, like when you start talking about thatkind of stuff. Yeah. There you go

Jason(host): [00:41:36]You'rechecking off the bingo card for me.

Isharna: [00:41:40] Cause you want to like,keep color about like what we're actually providing. Um, You know, likelearning blowjob techniques. Sure. You can get that in Cosmos, but then likehaving someone actually guide you through a blowjob while you're doing it toyour partner is actually like a really cool experience and very novel and likerewarding and high impact, especially in the context of a long-termrelationship.

Um, wherepeople are seeking novelty, um, within the context of their relationship.Right? So there's a lot of value in that stuff, but yeah, you have to easilytalk about that. And then there's suddenly thinking about a guided blowjob, soit's like, okay. And

Jason(host): [00:42:24]And then our DAUs are also up,

Isharna: [00:42:27] let's talk about CAC LTV.

Jason(host): [00:42:31] Well,um, like, I, I wish I could have been a fly on your wall throughout the courseof your fundraise, both to see you, um, breakthrough, because I know that musthave been just like you could describe it to slog, but also. Hopefullyhilariously funny experiences.

Isharna: [00:42:48] Yeah. There are some funnyanecdotes.

Jason(host): [00:42:52]Isharna, founder and CEO of Coral, thanks so much for spending time with us andmaking us blush.

Isharna: [00:42:58] Thank you. I've reallyenjoyed chatting

Jason(host): [00:43:05] Asyou just heard, isharna came out on the other side of the end, but had a roughgo at it. And as you might expect, she's not the only one. DocSend recentlypublished a study, which you can check out in our show notes that shows femalefounders raise almost a third, less funding than their male counterparts.

And that'safter talking to almost a quarter more people. So imagine you're Isharna andyou're battling that trend all are pitching an idea that makes investorssquirm. That's what my producer, Olivia wanted to know. How do you convinceinvestors to back an idea that's kind of unprecedented?

Okay. So youwere listening to that whole call. Could you tell how embarrassed I was gettingor did I hide it?

Olivia: [00:43:50] Um, I thought you hit it sowell, you seemed so mature and like competent.

Um, I wasright there with you though. Like, I felt like it was a, it's a hard topic totalk about openly and honestly,

Jason(host): [00:44:07]Yeah, I mean, as she was talking about some of those situations.

I mean, we,we talked about some serious topics, but as you really got into painting thepicture of it w what it was like to pitch this particular business one nightand got a little embarrassed. And then to really, really hit me hard about howdifficult that process was. I mean, it's so much of that, that process, andthat game is about getting people to.

Um, sit downnext to you and really dream alongside of you and think about your product andall the other ways it could be used. And it's an embarrassing topic. Uh,

Olivia: [00:44:47] yeah. It's so complicatedbecause I feel like, um, some of the other founders we've talked to have had ahard time getting people to connect with their idea, or like, to even kind ofunderstand the ballpark they're working in hers is so different becauseeveryone that's like, uh, above fourth grade, like knows about her topic, butthat has its own challenges too, where you're coming into a space that is socharged each individual investors seemed like they had their own complicatedemotions about it.

Jason(host): [00:45:24]Yeah. And it's, you know, one of the things people often make a mistake aroundis assuming that your investor or the investor that you're talking to is thecustomer. And in this case, her point is that most people, most adults shouldbe here, customer. Um, but the, the added layer of complexity on top of that ishow do you get an investor to. Essentially acknowledged embarrassing challengesthat probably everybody has at some point, but, um, yeah, I mean, I, goingthrough that and kind of understanding what she had to overcome was, was prettyimpressive.

Olivia: [00:46:07] Yeah. Ah, that's socomplicated and yeah, I guess one way she did that was by relating it to.Companies, it sounds like she really had to spell it out in terms, in termsthat they would be familiar with.

Jason(host): [00:46:22]Yeah, totally. She is one of a very new breed of companies that is coming outin the sexual wellness, wellness space.

Um, you know,but there is this concept, we refer to a lot, which is pattern matching andit's, it, it essentially means that investors are looking to align what theysee either in the characteristics of the founder or characteristics of thebusiness to something that they've seen before, either as a success or afailure. Yeah. And so when an investor meets an entrepreneur who herselfdoesn't match a lot of the typical patterns, one not being a man into not beingwhite and honestly, three, not being from the United States. If you layer ontop of that, a business within the sexual wellness space, that is certainlydoesn't have a ton of patterns to go after.

It wasdefinitely, um, a challenge for her to really make that. Fit in an investor'smind. So I get the draw to like using analogies. I mean, I referenced it in thecall, but I often make the joke Instagram for cats. Um, but when, when you'retrying, when an, an entrepreneur is trying to, um, activate the heart, thewhole pattern matching response from investors, right.

Dumbing it downand making it simple so that people can be like Netflix content on demand, aswell as Headspace, training of the mind. And then Headspace billion dollars,Netflix, multiple billion dollars that I see, I can see how it would work. So,um, I was, I was really proud of her for coming around to that.

Olivia: [00:48:02] Is that something thatevery founder does in a pitch? Like does every founder do a version of that intheir, in their pitch?

Like relatingit to things that already exist.

Jason(host): [00:48:13] Iwouldn't say every founder. Um, but when there are essentially complexcomponents to a company and a pitch that needs to be communicated reallyquickly, one of the tools or one of the approaches that can be used is matchingwith analogous companies.

So if, ifit's as simple as you know, we have this widget and we're selling this widgetand it solves this problem and it's. Immediately understandable. Um, thenthat's certainly not necessary, but, um, I know if, if you can point to astart-up that has reached unicorn status and say like, well, we're like themexcept for this, then at least.

People canmatch like, Oh, there is a go to market. There was a way to get to customers,um, that exposes you to a billion dollar market. And there is a content type orthere is a product type that similarly can be beloved by users and, um, turnedinto an everyday habit. That is a really great connector, um, for entrepreneursto make within an investor's head.

Olivia: [00:49:18] Okay. Gotcha. It soundslike one of the lessons. She learned was letting people go like knowing who wassellable and who could be convinced and who couldn't.

Jason(host): [00:49:32]Yeah. And I'm glad she spent time on this too, because, um, it's a lesson thatI think a lot of founders need to hear from, from other founders, which isyou're, you're going to get nos.

I mean, we'veheard that a lot, but more specifically. She realized that not everyone wasgoing to get the choral business or the vision that she had. And. If theyweren't with her, if they weren't like, ah, I thought about this problem, or,Oh, I also know this is a big problem and it took too much effort to convincethem no, those aren't the right investors for her.

And, um, youknow, moving on and focusing her efforts on ones that would understand thestory was the right move. And, you know, it's a good segue into this. You know,a second thing that I thought was a really powerful statement for her to make,um, and you know, difficult to. Talk about, but important for all of us tohear, which is that she, she kind of knew and, and found out he found out inreal life that it was just going to be harder for her.

Um, she,herself as an underrepresented founder, not white, not male. And she had adifficult business, uh, you know, one that, you know, made some people blush,um, But with that package and with that, um, set of adversities, it's justknowing that it's going to be a little bit harder and knowing that she's goingto have to keep pushing and knowing to stick to her guns, um, and continuing togo until she found the investor who thought like her, um, which I was reallyimpressed about.

Olivia: [00:51:11] Yeah. It obviously soundslike it was a really hard journey. Of course. And that story she told was justgut wrenching when she, I guess she super wanted to go surfing, um, that onemorning, but then took this last minute meeting where this guy was just likedrilling her on numbers that, um, he probably knew she didn't have, um, yeah,it sounds like it was, it was really hard.

It was all aprocess.

Jason(host): [00:51:38]And, you know, unfortunately, sometimes you run into investors who want to showsome level of superiority or, um, Some handle on metrics and asking difficultquestions. And it's just annoying when, when you run into that, especially as afounder, that at that point probably had gone through 50 meetings, all of thembeing nos and just to get another one where she got into it, where she's like,this is going to be a waste of time.

I mean, thatcan crush someone's spirit. Um, so also, you know, honestly it was also a goodstory to hear, um, Other founders that are going through it, like even the mostsuccessful founders, especially in fundraising go through tough times. And it'sa, it can be spirit crushing to go through this process because you just haveso many people telling you, no, you run into these meetings that.

Literally aredesigned and set up for failure. Um, that one investor probably had no, youknow, no intention of really getting excited about the business based on theway Isharna described it. Um, but it's one of those things that, that foundershave to go through. And so, um, kudos to her for sharing that kudos to her forrealizing that it's a bump in the road and things are difficult, but as long asyou stick to.

You know,kind of what your passion is and what your North star is, as long as you keepfinding more people to talk about, um, and continue to build the businessalongside of that. Um, I think the encouragement is to just keep going andyou'll find an investor who thinks like, yeah,

Olivia: [00:53:16] yeah, no, that seemed likea huge strength for her was her conviction.

Like she knewthat when people, when she was getting knows, like. It sounds like she didn'tlet that, um, make her question, her business idea. Um, it sounds like she justkept going, um, and like made in some ways. I think she made. Her own realitythat way and her own luck, because it is really easy when someone tells you noto believe them, but, um, she would have been wrong because she clearly wasable to make it happen.

So yeah, ittakes a lot of strength not to listen to those nos. Um, but she clearly wasright about,

Jason(host): [00:54:03]yeah. And I think that's kind of the thing that. It would be great to end on,which is like inspiration around strength for founders. And then I'll say itone more time. I like will probably lift out one of her quotes that shedelivered, which essentially it was like, I think everyone in this industry ishere to try to change the way things are.

Um, butthings don't change overnight. And so. Today and tomorrow, and maybe the nextday, it's going to be more difficult for certain people. Um, but it's peoplelike her that keep pushing through that set and example, honestly, she canbecome the pattern that other entrepreneurs after her get to match against.

So that morepeople that look like her, more people that sound like her, more people thatcome from her background end up getting funded, which, uh, you know, I'm justreally excited to see and glad we could find time with her. So, um, we really,really loved the conversation.

Olivia: [00:54:59] Yeah. Yeah. It was awesome.

Jason(host): [00:55:06]Before we go. Listeners, do you remember the last time you had to tell your momsomething uncomfortable? This clip is for you.

Do youremember when you told your mom that, you were starting this company?

Isharna: [00:55:19] Oh God. Yes.

Jason(host): [00:55:24]Thanks a ton for listening. If you have any questions related to today's show,or maybe you're going through your own fundraise and want to bounce somethingoff of me. So shoot me an email at I'd really love tohelp.

Find us onsocial, where we showcase other founders who are in the thick of it.

Now, the showis at funded pod and I'm @jayyeh that's J A Y Y E H. DM us. We'd love tofeature your story.

This episodewas produced by Olivia Reingold.

Isharna: [00:55:56] That's me. Hello.

Jason(host): [00:55:57]Thanks. Also to Jordan Pascasio from Adamant Ventures for his support.

Jordan: [00:56:01] Hey guys.

And shout outto Isharna Walsh for being an amazing guest and for making me blush

One lastthanks to our sponsor., DocSend the most trusted document sharing platform.


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