589 Insider Advice From A Serial Entrepreneur, Cokie Hasiotis

Welcome to Breaking Banks. The number one, killing it, killing it, killing it. Jason here with another episode of Killing It, the series on entrepreneurial journeys that just don’t always end the way we expected.

One of my biggest fears when shutting down Perk Street was how the friends and family that had invested in us would respond to the news that the potential acquisition fell through and, well, we were shutting down. That’s a delicate way of saying they’d bet on me, and that turned out to be a bad bet. But that’s how I thought they would perceive it.

On this episode of Killing It, Koki Hasiotis, founder of Twally, later turned into Drippy, talks to me about her entrepreneurial journey, the stress of the pivot, and how entrepreneurship changed her, and not necessarily in ways she likes. I may have lost money as one of her investors, but I would gladly bet on her again. I want to start, like, rewind a little bit on a text message I got from you on you had just had made the decision that you were going to be closing Drippy down.

This is on the heels of this is the second company you had founded. Well, yes, we knew it was on, yeah, but the second that you had gone after to create product and had raised money for, as opposed to Lasagna, which we can get into, but it’s, you reached out with a very specific ask of, you’re struggling with this idea of, as a founder, an identity. So let’s start with right now.

How are you feeling right now? Okay, first of all, I don’t remember this text message, and as you were talking, I immediately was like, what did I say? Like, immediately, immediately, what did I say? Yeah, how do I feel right now? A little broken, honestly. Like, I feel like a lot of my natural magic has been zapped from me. I feel like a lot of, I feel a lot of conflicting thoughts about who I used to be versus who I am now.

And I think a lot of that gets tied into the company, but there’s always, you know, a myriad of reasons for everything. And mostly just extremely lost. What do you mean about being lost? Like, post-Perk Street, like, that’s exactly how I felt, right? Like, I had lost my anchor, and I was, like, adrift in the ocean.

I think the lostness for me, and I’m going to talk about this a lot, so if you get annoyed easily, I would suggest you stop listening, because this is going to be the main topic for today. But I think the thing with being lost is a couple of things. The first is, like, my confidence is gone.

Like, all the things, you remember me a few years ago, I’d walk into the room, tell everyone what they thought, and tell them to shut up before they said it. Like, I had a lot of vim and vigor. And now that it’s kind of… Financial services and fintech, right? Like, so you were… One of the reasons I was the backer in one of your previous companies is that combination of energy, intensity, and expertise.

Yeah, you also… Historically, Jason, you like women who are a little rougher around the edges. I have noticed that… My wife doesn’t listen to this podcast. Yeah, I have noticed that.

You tend to respond well when somebody is very mean to you. Fair. Yeah, it’s… I appreciate you saying that, by the way.

That’s very kind. Yeah, the confidence angle, it’s just kind of gone. And then the other thing about being lost is that being lost is a pejorative.

And something I’ve been talking about recently with this group I’ve been working with is, like, maybe lost is just, like, bad PR. Like, because when you say mystery, well, then there’s this feeling of excitement. There’s something to look for.

So maybe we’re just branding it badly, you know? Maybe saying I’m lost is the thing that’s keeping me lost when I could be exploring or trying to solve a mystery. Well, I mean, you could be in stealth. It’s so stealth, not even you know what it is.

You know what? I didn’t think of that, but that’s way better. You’re in stealth mode. I’m in stealth.

So the decision to make either hard changes in direction or to ultimately realize you needed to go find a home, which, congratulations to you, you successfully found the soft landing, which is very hard. Talk to me about the decision-making process. Was it a back and forth? Was there a forcing function? Yes, yes, no, yes, kind of.

So the kind of process, and I’m very happy to be candid about this. We raised money under Twally, which was a crypto business that was brilliant. Honestly, I think that’s probably going to go down in history as the best idea I ever had.

A lot of credit to the people that worked on it, and obviously to Will White, who is a partner in almost every way with that business. So I think that was the best thing that will ever come out of me, maybe. Let’s hope not, but maybe.

It was brilliant, and it was starting to work, but timing was just not on our side. So just to give you a picture of what we were going through, the day we got our term sheets, we got three term sheets for our seed round. The day we got those term sheets was the day Luda happened, which was a major, like, huge crash across the crypto market that had major ramifications through the summer, to the point where our customer profile from June to September went from great to guy in basement, like, very quickly.

And then we were planning to launch, I think it was November, first week of November, maybe second, we were planning to launch the product, and FTX happened that day. So, like, in my opinion, the gods were not all for this. Like, there was some kind of force there.

Can you let me know next time, like, you’re launching some of that stuff, given the timing? I’m just going to go short markets based on… Honestly, there are careers where if you look at them and you match them up against something, that’s the person you should be shorting all the time. I’m hoping that I’m not consistent. So yeah, I’d be happy to.

If it makes you feel any better for a while post-Perk Street, I had, as my screensaver on my phone, one of those makeup of the, like, the opposite of inspirational posters that says, maybe your life’s purpose is to be a lesson to others. And it was a picture of the Titanic sinking. Yeah, I wasn’t depressed at all.

I wasn’t depressed at all. You seemed good. Yeah, you seemed good.

So basically, like, yeah, everything went kind of belly up with Twally. And it was, like, a great business. And if I just stuck with it a few more months, obviously things would have been different.

But I got nervous and I made the difficult decision that it was time to pivot. Because the way I called it was wrong. But what I called was, like, hey, our cycles come in four years.

We’re at the end of a pretty long bull cycle for crypto. We’re at this point, like, I don’t even think… No, at this point, Trump wasn’t running for president. We didn’t know it was coming.

And say what you will, but the man’s great for crypto. But, like, we didn’t know what was coming. We didn’t know the market was going to bounce that quickly.

And we certainly didn’t know that the market was going to bounce that intensely. So at that point, I was like, okay, we can sit on our hands for four years, or we can just go build something else. And I’m energized, like, I want to go do something else.

So we made the decision to pivot into Drippy, which was obviously kind of a talent manager for content creators. And we ended up kind of moving things along and starting that process when Twally was kind of at its weakest, really. It was like, we hadn’t even launched the product.

We’d been doing everything by hand. We had like 50 customers. Things were going pretty well, all things considered.

But our customer profile had dropped dramatically. So once we had done that, we started building Drippy in February. So this is like November to February, we’re ideating.

And everyone’s jumping on our throats telling us we have to build something. And I’m like, why is everyone so uncomfortable in uncertainty? So we started building something at the end of February, and our prototype was out and being tested in April. So we turned Drippy around really, really, really fast.

Then fast forward a year, we’re about to sell. So we basically, to get to the point of like, we need to go was complicated. So at our seed round, we had raised one of those beautiful crypto super rounds, which nobody tells first time founders like, hey, that round is going to be the reason you die.

Until it’s too late. They like mention it, you know, barely. But no one tells you that.

Yeah, well, I think you and I had this conversation, give that word of wisdom, because Frank Rotman, and I’ve had this conversation on the show. So what is the danger of that beautiful, big, beautiful round? Right? Yeah, we can definitely get into that. And Frank and I have actually communicated about this a little bit as well.

Frank Rotman is one of my favorite people to talk to, because he’s just so wonderful. But yeah, I like, so I decided to like kill Twally and birth Drippy. And in order to move on, I threw a, you know, I’m a little morbid and a little bit witchy.

So I threw a funeral for Drippy, or for Twally. I wrote an obituary for it, I gave, I like gave its eulogy. And then I had everyone in my on my team say a few words.

And we threw an actual funeral for Twally, which is very funny. I actually think that’s very healthy. Like that, to me, sounds like a great way to bring closure.

Yeah, I regret not doing it for Drippy, but I guess it’s not too late. And then when it came up to do Drippy’s next round, which was a year later, I immediately, very quickly in the process, I think I talked to like a few people, it was like a week, maybe two weeks at most into the process of raising the next round. That as the kids say, the math wasn’t mapping.

Like we just could not make that work, right? Like we had this crazy valuation. And anything we could do with this next round was going to be a minimum of 50% of a cutback. And like, the dilution alone would have made it totally not worth it for anyone to be a founder and even more not worth it for anyone to work for me.

So I was like, and simultaneously, my personal life was more or less on fire for the last like year and a half of my companies. And like, I just don’t think I had it in me anymore. Like, I just don’t think I had the like, let’s go get it.

Let’s go attack it. Because I was like, my personal life was burning and taking me down with it. Yeah.

I mean, that makes it exceedingly hard, right? If you need a source of strength and solid footing in one spot, because the journey is hard enough. Totally. It’s why it’s why I always get like icky feelings.

I literally was talking to a friend about this yesterday. Why I always get icky feelings when when people criticize Mackenzie Bezos for being like, oh, she didn’t do anything. Are you kidding me? To get all the to get half the money.

Of course, she did something like nobody exists in isolation. And you can’t do this alone. And of course, you needed to be there to be a sport for him to do the whole thing.

Like Amazon doesn’t exist without her being supportive of it in any way that she in all sorts of ways. Those 3am wake up calls with sweats. I think I actually gave you this advice when you were founding quality.

Get ready for the 3am wake up in terror. Yep. And I still have it.

So still with me. Oh, good. You don’t have to start up.

But you still have the terror. Good. Yeah, the terror I think is forever.

But the terror is good for you. It keeps you thin. Yeah.

So talk to me about the so the decision was made the math wasn’t math. Yeah. But again, text message in a conversation the two of us.

So you know, how do you find you the soft landing? I think I was more pessimistic than you was I too pessimistic. I said soft landings rarely happened. You didn’t pull it out.

I was wrong. I admit I was wrong. But I think it’s it’s funny.

Like it happened. I mean, it was luck. I basically had two offers and one of them felt like more work for me.

So I chose the other one. And the offer I had that was like, probably the better offer. The guy kept asking, talking to me like he was doing me a favor.

And I was like, on the one hand you are on the other hand, you can’t build the thing I just built and you want that like, can we stop acting like you’re doing me personally a favor when when we build a product that you are very interested in? And like the vibes? I mean, maybe I sound entitled, but I don’t know, I’m asking for is like a little bit like, stop talking to me like I owe you something, because that’s not going to end well. I don’t know anyone who acquires companies purely as a favor, right? Like there has to be some, which is why it’s hard, right? There always has to be some asset worth paying for. They’re not doing their fiduciary duty.

Yeah. And I mean, sometimes like, I won’t act like we had this big financial component to our exit, right? Like our, what ended up happening as we landed at an InsureTech that liked our payment flow and could have used that and wanted me to run their marketing, which I do sometimes like that. It wasn’t like, I don’t know, it wasn’t this huge asset thing.

It was, it was just like, this makes sense for us. It’s the next step. So decision is made.

You found two soft landings, which is even better, right? Means one of them gets to happen. And now you’re transitioning out. What were the first couple of weeks like? I think, you know, I don’t super remember.

Last summer is a little bit of a blur because every single person I’ve ever met got married last summer. So I was like loosely drunk all summer. Um, which I think was a great numbing mechanism to like, be able to keep going.

All my friends live all over the world. So I kept going to these like really amazing places and partying all weekend. And like, that was the summer.

Um, so it was kind of staving off whatever was going to be next. And I found a little, I think I found a little bit too much comfort in that. Like I was like, yeah, I’ll go back to work in September.

And then September came and I was like, I can barely move. I can really function. Yeah.

So yeah. The first couple of weeks I impulse bought a car, um, for my beautiful, wonderful fiance. He’s been on this.

Hasn’t he? He’s done this. Yeah. Oh yeah.

I think he’s mad. Cause I never listened to it, but in my defense, I listened to him talk all the time. It was a wonderful episode.

Yeah. He’s very, he’s a very good talker and he’s really in touch with his emotions. So I can imagine he was great.

Um, yeah, I bought him a car and then we went to a bunch of weddings and I feel like I didn’t tell anyone. I like didn’t say the words we got bought until maybe the end of the summer. Maybe I would, I don’t know why I just didn’t make it felt false or it felt, yeah, I felt like a fraud and I still do.

But like, yeah, like I think, um, there was a part of me that was like, no one’s going to believe me. No one’s going to believe that actually happened, which is such a weird thing to think. Yeah.

I don’t know if you’ve heard me describe the Perk street exit. Is that like saying we actually did Perk street. We actually did like, you know, playing on fire.

People were on fire, but nobody died, but we exited the plane. Yeah. No fatalities, but the whole thing burned.

Yeah. Yeah. Well, I mean, that is where the name killing it came from was that people would ask Dan and I it’s like, we’re killing it, literally killing it.

So you’ve gotten past that hump. You’ve picked yourself up again. If you reflect on this and I know having a fiance like Matt, he forces you to talk about the feelings of the journey, right? Given that is what he does now, professionally is work with entrepreneurs.

What would you have changed either business-wise or personally about this journey? Oh my God. Oh my God. Okay.

Um, yours for the next hour. Oh my God. Okay.

So I think the first, the first thing is I might not have done it. I don’t know. Like, I think when I look back, it looks very stupid for me to have done any of this at all.

Like lasagna printed money. It was easy. I controlled distribution and I controlled inbound.

I was cleaning up and I was so rich. And on top of it, I was like really healthy. And I constantly had a tan.

Like, what was I looking for? Do you know what I mean? But what were you looking for? Well, um, there’s a lot of things, right? Like I, I got a lot of, um, a lot of criticism. I mean, you remember I was more public as more of a public figure in FinTech at the time. And I got a ton of criticism for being the girl who had never done anything.

And I want it noted for the record. If you’re listening to this, first of all, if you said that, thank you. You’re so polite.

I love you so much. Secondly. Um, I want it noted that I did something that now there’s at least 10 people copying my exact playbook.

Uh, and it works so well. So you’re doing great. I’m really happy for you.

And on top of that, I like, I basically controlled the one source of media we had in FinTech. Then I made the one topic I was interested in the one thing we ever talked about so that every time it came up, it became a bigger deal. So it became everyone, every VC is like hot button that years because I made it that way.

So I don’t know, I, I screwed myself. So I started this company because I got this criticism that like, I’d never done anything. And I think I’ve had this perhaps wrong, but maybe I’m right.

I’ve always had this sense that I was like meant to be something more. Um, maybe it’s ego. Maybe it’s, you know, just like some of us just have this feeling and we’re diluted, whatever it is.

I always felt that. And so I wanted to go start a tech company, um, maybe like to prove something to myself, to my parents, to the industry, to whomever, like, cause I couldn’t really trust myself yet. So I went and did the thing.

Um, so maybe the first thing I would change is not doing it, but you also were doing it at a time. Like you had mentioned that bull run takes so much of the friction of becoming a founder out that you don’t have to do that. Stop and think right.

Money can be raised. I didn’t have that friction that most people would have had anyway, because everyone already knew my name, which is how the first round got done. Like the first round got done because I was a known entity to a certain extent.

And people like Matt Harris, who I’m now marrying no conflict of interest at the time, though, I want that noted. Um, but people like Matt Harris and Aaron Frank would vouch for me to everyone. You did it.

You did it for me. Yeah. I don’t even think I knew what you did when I wired the money.

I don’t think you care. I mean, you had the energy, you had the expertise, right? That was the bet. And even when you explained to me that the blockchain pieces, given it was an angel investment, I was like, I still don’t understand what you do, but I’m happy to back you.

So you’re good for you, buddy. Right. So it’s kind of all it is, right? Not have done it at all.

What else would you potentially change? I, you know, I say that, but now that I like, I’m actually feeling it in my body. No, I had to do it. I think I never would have rested until I did it.

I think I never would have done it. Yeah. Yeah.

Um, I would have offboarded from my previous relationship sooner. I think that was a big one because that, that actually ended up like, I mean, my life was falling apart, right? Like in that, in no small part, because my previous relationship was on fire, but yeah, I probably would have offboarded from that relationship a little faster. Um, knowing you feel like you had the company, you couldn’t just take on any more complexity.

I mean, what else was I going to do? Like, I thought this was the person I was supposed to marry. This is supposed to be everything. And he, um, didn’t necessarily support me in actions only in words.

So he would tell me how like supportive and proud he was of me, but he would never like show me that. And then whenever it came to like serious moments of complexity in the company, he’d be like, why are you complaining? Your job is so easy. You barely do anything, you know, like these little micro things that over time, you’re just like, are you kidding? You know, um, if I had exited that relationship a little sooner, I think that probably would have saved a lot of the emotional turmoil that ended up like exhausting me to the point where I could not perform in the company anymore.

Got it. Hmm. That’s a tough one, right? Like, Oh yeah.

Especially when it’s all you got. Right. Yeah.

I mean, like we launched, okay. We launched the prototype for drippy while I was in surgery, getting my eggs frozen. So I was already crazy from all the meds for two weeks.

Cause I was like better secure my future. So I can have a baby one day, you know, like why was that the moment anyway? Why was that the moment? Nevermind. But we should go back and look at Koki at that time and ask her a simple question of, are you stupid? Um, like why F why was that the moment? Uh, and then when we launched, I was in the process of moving out of the apartment that I shared with the man.

I thought I was going to marry like Koki, what are you doing? Literally, what are you doing? So I had basically like finally like unburned my life down. And then immediately after that, we launched, we had a really busy summer. I was like constantly on the move, constantly working, didn’t sleep at all, but it was fine.

Cause it was kind of fun. And then went into fall, like already really exhausted. And then we, we kind of closed up shop the next spring.

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Thanks for that. For like five minutes. Yeah.

But for those who look at this, because the longer bull versus the bear as of late, not just in crypto, but FinTech kind of writ large, what do you think from a like personal assessment? What are the questions someone should be asking themselves? Well, that’s a really good question. So the first thing I would say is if you’re listening to this podcast and thinking about starting a company, I already have like almost full hope in you. If you’re starting at like, how bad could this go? I have a lot of faith in who you are, that you’re actually doing your due diligence on the experience.

That’s a big one. The next one is, can you at this moment in time live outside your head? Is there, how accessible are your feelings to you? Because mine are not until very recently. I don’t think I’d had one in a while, like mine are not.

And I do find that founders get so locked up in their brain that they never actually have an experience in their body. And when you cut out the experience of your body, you’re cutting out your intuition and your intuition is so, so, so necessary for you to do this well. So be honest with yourself, like talk to your therapist or I don’t know your guru.

I don’t care. I think you actually like first step before starting a company is go get a therapist. Oh yeah.

No. When I elevated my co-founder into that position, Nick, I made him get a therapist. First thing, I don’t think he ever did, but it was part of the deal.

It was part of the deal for sure. All right. So that get in touch with your emotions and make sure you can get out of your Yeah.

Like make sure you have that pathway built out. The next one is be honest with yourself about your superpower. Do you actually know what it is? Like it took me till after the companies were done to realize what mine were, which are, and I don’t mean this in the pejorative, but manipulation and people management.

I’m very, very good at those two things, which is why I’m very, very good at raising money. Um, be really clear on what your superpowers are because you’re going to want to do everything, no matter what, like you gave birth to this thing. You’re going to want to do everything and be intimately involved with every corner of it.

But you have to understand that you’re not good at all of that. So where can you focus? That’s like truly great for you. If you can be honest with yourself about that.

And again, this takes a second party, like you need a mirror. You need someone to reflect this back to you. May I recommend a coach that lives in my house? Um, but you need a mirror.

I got, I got those to take, go, go make him work. Not me. Um, yeah.

If you can, if you can like have someone mirror this back to you, because I think a lot of people get stuck in wanting to do everything or they do everything in the early days and then they don’t know how to let go of it when you really need to again, get back into your body and get back into what you’re truly great at. Well, and if you have a coach, I do think you need to be very careful who you surround yourself with too many people who, you know, yeah, you should have chosen better than surrounding yourself with folks like Dan Rosen and I, but you need people who can honestly reflect back. They’re not just part of the rah, rah, we support you no matter what, you know, you need some of that hard feedback before the market gives it to you.

I do have one more and I don’t really know how to word this. So just come with me on my little word salad. Yeah.

But I, you need to like, I think the best founders are the people who are the best at filtering because everybody’s going to give you advice. Everybody’s going to post on LinkedIn, like these are the top 10 ways to do content marketing. And if you do anything else, you’re a moron.

And like your VCs are going to have certainly a lot of opinions. Your mother and father are going to have a lot of opinions. Your friends from college, like want to feel like they are better than you because you’ve now like stepped into a place that they cannot or will not step.

So they’re going to want to make you feel small by telling you what to do all the time. So you’re going to constantly get this, like blabbing a lot of it from sources where, you know, the intention is actually good in kind, but it’s deeply not serving you. So the best people for this job are people who are really, really, really good at filtering information and not taking it too seriously.

Makes a ton of sense. So what other advice would you give to someone? So they’ve done the personal assessment. They’ve surrounded themselves with people that are good mirrors.

They decided they can get out of their head. They know what their superpower is and they know where they need to stay in their lane. They jump off the cliff.

As they’re falling, what’s your advice for them? It’s a simple one. Every time you interact with somebody, every single time you interact with somebody in a professional context at all, follow the incentives. So if one of your onboarded already VCs is acting weird, there’s usually a pretty clear linear reason why if you just follow how they get paid.

Same with if people want to partner with you, that’s pretty obvious, but go follow their incentives, not your own. Always make sure that whenever you’re dealing with somebody, you know where their incentives lie, because that is the way to not only harness the relationship, but control it for your own good. Because a lot of people are led by these incentives, and then you add ego.

So you add ego to a paycheck, what do you get? You’re dealing with somebody who’s potentially not a rational actor, and it’s now your job to go figure out how to manage that situation. So that’s my big one. And that mismatch of incentives, if you’re not clear on what their incentives are and yours, that can be an obstacle that cannot be overcome.

At best, it’s just a tension between the two directions, or it could become something that kills the company. Definitely. Yeah, that’s a big one.

So what’s next for you? Oh my god, I have no idea. Get married. Yeah, I’m getting married in August, so we’re going to start there.

We’re going to start there. Yeah, I’m just starting to explore that now. Big shout out to the VC formerly known as Shloff, otherwise known to us that love him as Steve Shloffman, who started Downshift.

I’m going through that program right now. It’s basically high achievers who are going through transition, and what that transition feels like, and kind of how to get into that. I’ve so far found it very helpful, but also frustrating and difficult.

And I’m finally accessing some of the things that I was locking up, so I’m a little bit more free, which I’m grateful for. And during this journey, the point is to kind of not even necessarily have a direction coming out of it, but have an idea of how to get to that direction. I will say that I’m not particularly drawn to tech right now, and I don’t know if that’s fear, and fear of rejection, and fear of failure kicking in, or if it’s just not that sexy and interesting to me this year.

It’s hard to say, or does it feel a little played out that, but I’m a little bit more drawn to things that are a little more creative in nature, which is something I think I’ve denied myself for years, and things that are a little bit more cash-oriented in nature, because I love to be rich, and I miss it. Yes. No one gets rich in tech.

Big equity payouts. Well, I mean, in boom cycles, right? It’s just not the guarantee that it once was. Yeah.

No, it’s not. And even the big booms aren’t what they used to be, and it’s 15 years later. Yeah.

Well, thank you for your emotional honesty, and sharing the journey that others can learn from. And thanks for letting me be part of the journey. No, thank you, Jason.

I know I’m not usually nice to you, but I truly probably wouldn’t have taken the step, and I wouldn’t have been so brave if I didn’t know I had people just like you waiting in the wings. And there’s a reason you were one of the first people I texted when everything went to hell. Well, taking it there and back again, my friend.

There and back again. That’s it for another week of the world’s number one fintech podcast and radio show, Breaking Banks. This episode was produced by our U.S.-based production team, including producer Lisbeth Severance, audio engineer Kevin Hirsham, with social media support from Sylvie Johnson.

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