$0 to $4M: Inside the Bootstrapped Rise of Whippy with David Daneshgar

I think when you're growing a company in general, like you have to be able to execute. And the way that I see that is sometimes you have to fake it till you make it. Sometimes you have to tell someone you have a product and that's how you scale, by the way. You tell them, hey, I have this product and they purchase it. And you know what you say? Guess what? We actually aren't ready. We'll give you 20% back, but then we should build it.

Why business school? Like, why is that the logical path for you? You're like, I'm crushing it in poker right now. Buy that.

So I always thought of it like, it's not that I'm going to leave. It's just not gonna be my primary modal to making money. Yeah, it's actually gonna be my disconnect. I mean, there was a lot of good in business school, but also probably another thing is I could have just said, you know what, I'm just gonna start a company.

What was helpful on the sales side? What makes you a good salesperson?

I don't know if this is gonna be good or bad, but I compared to dating a lot. I think the World Series of Poker helped a lot and just poker in general. And I still play it here and there. You have to have a gut for certain things. And gut to me is like you see pattern recognition, you see certain things and you calculating, that's analytical. Yeah, we do, I think, have the best platform for texting, texting automation, texting chatbots, you know, all that stuff around that. I remember at Bloom Nation, when we got to a million, we celebrated.

Did you?

Yeah, I remember here we didn't even think about it. I think the worst thing you can do culturally is have someone that can be somewhat cancerous to the company. That doesn't matter how much revenue they bring, that's a disaster. And this is one of the takeaways I'll tell, tell the people listening, you have to have no backup plan.

Welcome to Just Go Grind. I'm your host, Justin Gordon. Today's episode is sponsored by Ro, the all-in-one finance platform built for startups and high-growth businesses. With Ro, founders get a single pane of glass they can use to run and scale their business— bank accounts, corporate cards, expense management, bill pay automation, and accounting— to help them move as fast as they scale. Ro is trusted by thousands of companies, from 2-person YC startups to brands like Perplexity, Cal.com, Splitwise, and more. The big thing with Ro— every customer has a person at Ro. 24/7 customer support— that's phone, text, email. They will be with you at every critical milestone in your startup's journey. To learn more about why startups choose Ro, visit ro.co today. That's R-H-O dot C-O today. David, welcome to the show.

Thank you for having me.

There's a lot to talk about with your background, with all things poker and multiple startups and everything like that. But for people who don't know Whippy right now, what is this company doing today in 2025?

Yeah, so we're, we're think of an omnichannel SMS, email, voice.

Yep.

A lot of what's going on right now are these AI agents. So a recruiting firm may use us when someone actually applies for an application. to like screen and then put it back into their system. A pharmacist may use this to verify refills. So a lot of it is built off of this movement in AI agents, but also we have a VoIP, a dialer, a text. So some people use us just because we're integrated to softwares like HubSpot or industry-specific softwares. And then we have another part that's automated so people can build workflows. We have a workflow builder as well. And so it's being used in a bunch of different industries. We're industry agnostic. And a lot of that came, and we'll talk about this, from working in a company prior that had a small TAM or addressable market. And so this time we decided to shoot for the stars.

Yeah, I want to get into all that. There's so much to talk about with that. So let's take a step back. So even before starting Whippy, obviously you're at Bloom Nation before, for people who don't know, venture-backed startup. And poker was in like, what year was that? 2006, roughly?

Yeah.

Okay, 2006. Why the change from poker to then the startup world in general?

Yeah, so the interesting thing is actually The story is pretty interesting. I don't know, are you a basketball fan?

Yeah, definitely.

Okay, so I mean, the short of it is I was friends with the owner of the Lakers, who was Jerry Buss, who passed away, who was like the all-time best owner. He used to play a lot of poker with us, um, and I would play with him in heads-up games. And I remember once or twice I would actually go to his house, which was, uh, not far from LMU, and we just chit-chat. So, and it was cool because he enjoyed poker, I enjoyed picking his, his brain. But I think he was the first one that kind of got me started and like, hey, poker is a good side hustle, but if you really want to play a big game, there are much bigger games outside of poker. And so that kind of got me riled up. I was always a big Laker fan, like Kobe and before Nick Van Exel, Eddie Jones. So like I took that to heart and they helped me actually, believe it or not, like the LA Lakers actually wrote my letter of recommendation. So I was on Laker paperhead. So that was awesome. And I ended up going to Chicago. For business school, which I can tell you was business school worth it or not, that's another conversation. Yeah, but that was just kind of the moment where I was just like, you know what, if you love the thrill here, the thrill is so much bigger in a bigger felt that's not just green and surrounded by 10 people. And so that's where I made my kind of move to business.

How long were you playing poker before you became like a World Series champ? Obviously there's different tournaments they have for that, but how long were you playing before that even?

Yeah, so I think, I mean, probably I could surmise it down to 5 years because the last year when I was at Cal Uh, that was 2003. That's the year that Chris Moneymaker won the World Series and where it all exploded. And it happened to be the same year that I was teaching poker at Cal. And so what I mean by that is they let you teach courses.

Okay.

Pass, not pass. Like, you couldn't like flunk anyone out. Uh, mine was called the Statistics and Probability of Gaming. And so that got me really excited about poker. That was 2003. And then I went and had a job, probably the only job I've had in my life, real job. I mean, I think these are real jobs, Was about a year, and then in 2005 I started going pro. 2006 is when I was ranked top five, so that was like my big year. But I still didn't have the bracelet, and I won in 2008. And right after I won it, I started applying to business school. What?

Why business school? Like, why is that the logical path for you? You're like, "I'm I'm crushing it in poker right now." Yes. Why that?

I think I'd already decided that. So like this summer, now that Whippy's growing and I have some great people on my team, I'm gonna go play the World Series of Poker. So I always thought of it like. It's not that I'm going to leave. It's just not going to be my primary model to making money.

Yeah.

It's actually going to be my disconnect. Business school, that's actually a good point. I don't know, thinking back in time, I mean, there was a lot of good in business school, but also probably another thing is I could have just said, you know what, I'm just going to start a company.

Yeah.

But it's hard with poker because what ends up happening is people have a bad day in a company, a bad week, a bad month, and they just go back to the tables.

Yeah.

And I realized to be successful as an entrepreneur, and this is one of the takeaways I'll tell all the people listening, You have to have no backup plan.

It's funny, I talked to Chris Lee, who's also a poker player in LA. I don't know if you know him or not.

I've ever heard of him.

Yeah. So like I interviewed him and same thing. He went from poker to business school at USC. That's how I knew him. I don't know what the connection is here between why people do that. They just think like maybe business. I guess it's a good fallback because like regardless, it's like, OK, a job opportunity would be there. You'll learn some different skills. For you, what'd you take out of that experience?

Yeah, no, that's a good question. So. I learned pretty quickly in business school that the direction I want to go is not necessarily like everyone else. So in business school, for anyone that's thinking about it, I mean, I think it's really good if you want to completely change careers and you can't get into it otherwise. So like an example of that would be someone who's doing poker and wants to go into venture capital or investment banking or consulting at like a big firm.

Yeah.

But I pretty quickly realized that's not for me. So then the whole point is like, well, what am I going to do with the rest of school? And that's actually where Bloom Nation came in. A friend of mine, my former co-founder at Bloom Nation, he had this idea about connecting people to florists, kind of like what happens with Airbnb. You type in an address and you can see the apartments. Some of them are hotels. Some of them are actually like, you know, at home you couldn't discover anywhere else. And he saw the same issue with flowers. And so I think I piggyback off that the second I realized investment banking is not for me. Okay. And that's kind of where Bloom Nation was kind of born as well. And that's kind of where we scaled it in business school. And it made school much more fun. Like, to be honest with you, it made it more practical. So like the first year, I was like in investment banks, going to networking. They called them crop circles where they like surround you. And I just, it just wasn't for me. I would just tell you it wasn't for me. Where some other people, they may make that switch from poker and it's great. It just wasn't for me. I realized quickly. So when, his name was Farbod, when he and Greg, who are my 2 co-founders, former co-founders at Bloom Nation, Mentioned, hey, we're thinking about doing this. Do you want to jump on board? I was looking for something different in business school. So that's kind of where—

You're like, perfect.

Perfect, perfect, perfect. And that's where it was born. And I think that motion and that rhythm of figuring out how to scale sales orgs and go-to-market kind of has been helpful ever since.

I want to go into the early days of BloomNation, because it changed name as well, people who don't know already. But it changed names after— at some point. I don't know. What year was that?

Right after I left.

Right after you left. OK, so right after, literally right after. Early days, getting customers, figuring out what this product was going to be. Take me through more of that, BloomNation, because you guys also raised venture capital, which is a whole juxtaposition from what you did now with Whippy. Take me through the early days of getting BloomNation off the ground, at least.

And that's a good conversation, like venture versus no venture.

Yeah.

So there's actually an interesting story that's true. So when we were starting BloomNation, I was at business school, and none of us are technical, so we needed $50 grand to get the first MVP going. And that's actually where I went to Commerce Casino.

Amazing.

We're just sitting at my apartment mocking things up, and I just like looked on the Poker Digest tournament at Commerce, first place, $50 grand. So it's a little bit like a movie.

Perfect.

And, and that actually ended up becoming a blessing because not only did we get the $50 grand, that's been a huge thing for just like picking up the story, press, getting— of course, getting that out there. Um, so that was Bloom Nation, and then I think Like, what did that look like? I think I'll just tell you, I had no playbook.

Hmm.

Like, I ran sales. One of my other partners ran product, one ran operations. I'll just tell you, we just hustled. So like, and that's something that I think here, and I think that's like a lost art. So there weren't a lot of SaaS companies back then. So it kind of like predates us, but that was 2007, 2008. 12, 13 that we started it. Yeah. So at that point, that's a decade ago. Like actually at that point, SaaS companies didn't have as high a multiple as marketplace companies. That just shows you how far back it was. And we got lucky. We got some customers. The one takeaway I learned from there is we went B2C, which means, you know, we're like trying to push bloomnation.com, this like marketplace, but we realized there's more money in B2B sales.

Of course.

Which is like, while we're talking to the florists, oh, you need new websites, you need new marketing tools, you need, That stuff, and that was more my my strong suit. I wasn't ever like a huge growth marketer. I wasn't the best at at brand, but I was really good at calling people and convincing them to do stuff. And so that's when the venture companies came in, and it was lucky we had like some really good companies like Andreessen Horowitz and Spark Capital, and we scaled that. And as you said, we scaled it, and then as we as I left. Which was 4 years ago, a little over 4 years ago, they rebranded to the Promenade Group because what they wanted to do is do Bloom Nation but in a whole bunch of verticals. Like, they want to do it in liquor and in restaurants, but that became crowded because there were other players there. And so that is a learning I took to Whippy. When Jack Kennedy, who's my co-founder there, we started this, he was an engineer at Bloom Nation. I think we had like this insecurity that like we didn't want to be a company that that we got to this point where growth was capped.

Yeah.

And so, and we'll talk about that, we did the opposite. We decided to just go for something that's so vague and so broad that there was a different problem there. It was just like defining your messaging and your market, but that's what kind of excited us.

With Bloom Nation in the early days especially, you mentioned the sales side of it, you were good at the sales side, and that's something every founder obviously has to learn, or they either have to find someone who's that side of it if they're a technical founder as well. What can you say about the sales side of startups, things that are helpful for you in those early days of Bloom Nation? We can talk about Whippy after this as well, but like, What was helpful on the sales side? What makes you a good salesperson?

Well, I mean, I don't know if I'm good. That's like a different conversation. But I mean, I don't know if this is gonna be good or bad, but I compare it to dating a lot. And like, you don't have to have the best car, the best clothes. Like, that's not the person that's usually the most successful going out. It's the person that just has the most conversations, like who's not afraid of rejection. Who actually thinks of themselves in a certain way that others may not think about, and that carries off. And so I think in sales, I mean, we had a good product. I think we were able to make really good connections. And I think the other thing that we're really good at doing at both companies was leveraging those contacts for more. So we were never good at like, oh cool, your customer thinks. We're always like, hey, do you know other florists? And at BloomNation, or, and in BloomNation, we scaled actually by going one level up, the wholesalers. We made, I was able to make relationships with all these wholesalers that sold them flowers. And I convinced the wholesalers around the country to do these joint events with us to say, you know, what's good for your customer is good for us and good for you. And that helped actually speed go-to-market.

Oh, interesting. I just talked to Everett Cook, the CEO of Ro recently. They're a sponsor of the show as well. Thank you, guys. And like in the early days, especially, they did so many events as part of their growth strategy. It's like, how do you stand out? How do you build brand in something like, business banking, and they're like, we're gonna go host events, we're gonna have just kind of boots on the ground style. I could see where you can easily partner up with all the other service providers who want the same customers. Yes, it's like jointly beneficial. So very helpful in that way too.

And I think a good example of this, just to tell you, and I don't know if this will just show you in this world, we, we just sponsored a show, a trade show. Yeah. And I think it cost me like $50 grand. I'll have to look at what it was. We got a booth and it was great, great great event. There was someone else who had sponsored the prior, uh, booths, and he didn't. He just went— it was in Miami at the Fontainebleau.

Yep.

He just ended up getting a cabana at the pool and a penthouse.

Yep.

And he'd just go in the lobby and invite people. And I think he paid— I don't know what he paid.

Let's just say a fraction of what I paid for the suite or whatever it was. Yeah.

And he had like his own conversations, intimate conversations. And I was like, wow, that's pretty hustle.

Yeah.

So I agree. Like, one of the things I was thinking at the show, like, I'm a basketball fan, a sports fan.

Yeah.

Is should we just call like the largest prospects and then just invite them to a box at a sports game? Like, and if we do 10 of those, maybe that's the same cost as a trade show. And I think I'm gonna measure and I can come back and tell you which one gives you more return. But my gut is those high-touch kind of events with larger prospects might actually You know, prove more fruit.

Yeah, especially depends on like what your lifetime value of a customer is, right?

Yes, yes.

And like, that's a huge part of it. I looked at even from a perspective of finding sponsors for the show, it's like, okay, who has a high LTV? Because then obviously they're willing to spend on sponsorship.

Yes.

But also it's like their customers are just worth way more.

Yes.

They take more shots on goal, everything. And to the point of like showing up, not even having like the trade show booth, it's like the Tim Ferriss thing in the early days of 4-Hour Workweek.

I loved it.

It was just like South by Southwest. He was just at the like bars and stuff talking to people, not even in the show.

I love it.

I love it.

Amazing. I was even on my reps. We took a bunch of reps. We only had a certain amount of passes, but I still took the other reps in the lobby. And I was like, I noticed there were more people there and deeper conversations at the bar over whiskey, right?

Yep.

So I do think that is hustle, by the way. That is hustle. If someone's thinking about starting a company and let's say it's in the podcast world, just go to the show. Like, if you can't— I mean, this is probably not good if you can't sneak in, right? And I did see people sneaking into this one and I didn't rat them out 'cause I was like, that's hustle. You're asking how to start a company. But then go start at the bar, sit down there, open a bar tab, buy someone a drink, ask them questions. Like that to me is like one sign of hustle. Yeah.

With Bloom Nation, so obviously you raised from really good investors like A16Z and stuff like that. Like what was the progression in terms of as you guys started to grow, what was fueling that growth? How did it like evolve or change over time?

Yeah, so the big thing is, I mean, we really, I always believe in revenue as a, Growth. Like, there are a lot of people that I know that have really good ideas, and I always tell them the same thing. Like, you know, I'm Persian, right? And so many of the last generation said they should have come up with Uber. My brother-in-law's father says that too. But it's all about execution, and the only way to execute is will people pay this and can you execute? And so many people have these ideas. Ideas 1%, execution is 99%. So I think when you're growing a company in general, like, you have to be able to execute. And the way that I see that is sometimes you have to fake it till you make it. Sometimes you have to tell someone you have a product, and that's how you scale, by the way. You tell them, hey, I have this product, and they purchase it. And you know what you say? Guess what? We actually aren't ready. We'll give you 20% back, but then we should build it. And money is what guides you. And so at Bloom Nation and here at Whippy, more than anything, It's actual contracts that people sign and willing to pay, even to your viewers, if you have to refund their credit card and tell them, you know what, I was just joking. Yeah, but that's true product-market fit to me.

Yeah, because I don't want— everyone kind of bullshits if they like have a waitlist.

Their friends are always going to tell them it's great. But tell your friend, tell your friend it charged our Amex $30 grand. Yeah, and then you'll see if you have a real idea. So to the question with Bloom Nation and scaling, yeah, and here with Whippy too, it's like— and it's even harder because you're bootstrapped now. We make sure that we're building the products that actually will drive ARR growth.

Yeah, that makes sense. Otherwise, it's like, what are you doing?

And you're right, dude. So many people I know that I talk to are like, well, my friend said, or the customer said this. But I really believe you got to charge the AmEx.

Yeah, I think charging is the only way to actually have a true, a true grasp of if a customer will be a customer. Because you see the waitlist of like tens of thousands of people on this waitlist for this product. And how many of them convert? And it's always a fraction of the amount. And people get super hyped, like, we have this waitlist. OK, how many customers do you have? Paying customers do you have? Which is really what matters at the end of the day. Going from Bloom Nation. So when did you— 2020, roughly? Yeah.

OK. Right around COVID is when I took like an actual go-find-me trip. I went to Asia for 2 months. Oh, I love that. I came back. Just happened to be at the same time, which is, well, right before.

Crazy timing.

Crazy timing. Came back. And, uh, this engineer that worked close with me at Bloom Nation had gone to Shutterstock. Um, and we always kept in touch and we had a good bond. And he said, when I left, I'd love to work with you. And, you know, a lot of people say that, but again, it's execution. He actually followed up, which is rare. I've learned just like actual follow-up is rare.

Yeah.

And so I took it seriously and we just started brainstorming ideas. And we started by building actually more of like a consulting firm, like a web agency, so to speak, to see real pain.

Yeah.

And that's where we started to discover like these people aren't getting back to leads, they're not calling, like they're not following up, like their communication isn't seamless or integrated, they have 6 different softwares. And so the idea— and it wasn't, it wasn't like an overnight thing. Yeah. Even to today, it still kind of adds products and ideates just a touch, but we build on top of the core problem that we see our users have, which is just communication.

I want— I can't just like gloss over that couple months of you finding yourself or whatever you want to say, getting away. Just take me through that because I know a bunch of founders who have done the same thing. I know a friend right now who's like trying to exit one of his companies to start a different company that he's like interested in. What were you even doing in that time? You're just like trying not to think about work? Or you're like— take me through that for a second.

So, it's actually interesting. Another friend of mine who used to work at Bloom Nation, I was like, I decided probably 4, maybe 6 months before I left, maybe even a year that I was heading in that direction. So, I had to find my replacement. And so, when I decided to leave, I was like, just like, let's start something else. I want to start something else. And a friend of mine kind of talked me off of that ledge and said like, just, just like, don't think. And I think being the poker player, I'm so analytical and I overthink a lot. And so the only thing I did is I just bought a one-way ticket to Tokyo. That was it. And I was like, oh, I'm going to go for 2 weeks. I ended up going for like 2 months and I traveled around Asia. But there was— the surprising thing is, although I had some thoughts, I didn't go deep in thoughts. I, I think it was just like, honestly, just like to recharge.

Yeah, it's funny. It's the same thing that Sam Altman talked about after I think one. I think his first company where he took a. He's like basically saying if you can take a year off in between something and like actually think about the idea you want to start and spend way more time on, it's worth it. Yes. Obviously did a bunch of different stuff since then. YC as well as OpenAI and stuff. Yes. But at what point in that time period, that two months then, were you like itching to do something else? Or like how did that progress?

Well, here's the thing. I think one thing. in my case that's unique is I was itching to get back and just do it because Bloom Nation hadn't exited, right? So it wasn't like I could say, hey— and I think that's a— was it look like, uh, something where I was like, oh man, but it ended up becoming a blessing because it— going back to you have to have your back against the wall. No—

Yeah.

No backup. Like, I had to make this next thing work. Um, and so I think it was like within a couple months of getting back where we started— honestly, the only thing I really had going for me was Jack, who was my partner, and we just decided we enjoyed working with each other. We didn't know what we're gonna work on.

Yeah.

And some could even attest that we still don't know what we want to work on, but we just knew that we wanted to work together. And he took more of a sales-driven engineering approach. Like, he would jump on calls, he'd talk to people, and that's such a blessing. And I think that's also another thing that's been very helpful, like with Bloom Nation. I couldn't be more thankful to the co-founders I had there because they dealt with my insanity, right? Like, like you're coming as a poker player. But I also think not having an engineering background— and I'm no engineer, I don't, I don't have a line of code in me— but I think understanding like roadmaps and, and prioritizing products on my end and working with someone who is a true engineer and understands architecture and like investment, like that is probably the ideal partnership for starting a company moving forward in today's world.

Yeah, that makes sense. So for Whippy then, in the early days especially, you raised a decent amount of money for Bloom Nation, like $20, $25 million, something like that, from top investors. How did you even think about that for Whippy?

I mean, we just day one said, again, going back to the fact that we hadn't exited, we had these— I had these own personal securities. And like, in the end of the day, I think there is something to be said about the startup fairy tale, which is like, oh, you see these people that cash for billions of dollars and that's the only thing you look at. And it's like poker tournaments, only thinking about winning, which I was lucky enough to do, win a World Series of Poker event.

Yeah.

When there are 3,000 people. But I think also looking at other outcomes that can change your life is super helpful. So the common thing that kind of just got me thinking is like, you know, if you raise venture, anyone does here, and you raise all these rounds of funding, you have multiple people, and you bring in managers, like, you end up— even if you sell for like a, let's say, a billion dollars, in the end, these founders are— and believe me, I'm not complaining— they're walking around like $50 million, which is awesome.

Phenomenal, yeah.

I'm not saying it's not, but the odds of that, if you want to be like a poker player, are very low. But if you bootstrap something, you drive it, like, can you get acquired for $80, $100 million? Like, that's a sweet spot, and you just own the company, or you and your partner own the company. That's a much more realistic outcome to get to that.

Yeah.

And I'm actually not saying that's where you'll end up, but if you start to think like that from the beginning and build that type of mentality, you probably are going to get to $1 billion regardless.

Yeah.

But because at that point you can raise a little capital to get you going and stuff like that, but the choices are yours. No one owns you.

Oh yeah.

By, by the you-know-what. And I think we did see certain things when we structured the deal that I learned, like we had to recap our cap table. There were certain things where investors had certain rights And I think ultimately, you make incorrect decisions. So like, I think when someone gives you— and this happened to us, like someone gave us $5 million. And I do agree, the events are one thing, but we went crazy on thinking about getting an office and the office furniture and all that allure. And I think when you start the company bootstrap, you think like, I'm just going to make this your dad's generation. And you think about someone who started a business and all they care about profitability, and it changes the way you think and make decisions. And I actually, to be honest with you, I prefer it and it kind of Kind of makes you start to have a lot more respect for people in private equity, because you think about, like, how they restructure companies and how profitability is the most important. And I think that has been one thing that when I was in BloomNation, all I was enamored by is venture capital.

Yeah.

And I think now all I think about is more like the private equity world. And that's the distinction I have between those 2 worlds.

I feel very lucky to have a taste of kind of all of it in terms of what I've seen, having been at a venture firm, having interviewed 350-some founders now. Like, even yesterday. So, at the time of this recording, let's see here. So, yesterday, as of this recording time, I interviewed Tim Hueskamp from 1440 and he's a former PE guy. 1440 is doing $21 million in revenue with 21 employees.

Yeah.

Like, more than $21 million in revenue.

Yes.

And like, he comes from PE world. He's like, we're going to bootstrap this thing.

Yeah.

They raised— he put some of his own money in, I think like $125K maybe to start with.

Yeah.

And he raised some debt instruments and a little tiny equity kicker. So, he owns now like 90+% of the company and doing $21 million in revenue and they just keep reinvesting in the flywheel of growth.

That's the dream. That's the dream.

Yeah. So, like, when you're doing that with Whippy, tell me, like, how long was— a timeframe was it between like having this idea for the company and bringing in money, capital, like in terms of like revenue? Like, what was that timeframe?

Oh, very—

Product to market. Yeah.

So, that's a good question. So, I mean, we put— maybe I put a little bit of my money in.

Yeah.

very little. Revenue is almost immediate because, I mean, here's the caveat. That's why I think the founders and their skill set makes a difference. So I wasn't getting paid in the beginning and Jack wasn't getting paid. And I would assume if we were to work at a big company, I mean, probably with his skill set and mine, probably in terms of salary, at least a couple hundred grand each, if not more.

Of course.

You're right. So that's what we're forgoing, I think, for the first year. And we're both on the same page. I think that's really like what I would call like our sacrifice. Like we, as a result of that, we were looking— it's back to what I'm saying. Like we were not building stuff. We actually probably were. And to Jack's— a lot of respect for Jack in this sense. He'd be on calls and he knows the technical infrastructure and he's the opposite of the engineers that I've known in the past. Like someone would ask for something and we'd see how much they want to pay and Jack would say, yep, They'll be ready in a couple of weeks. And he'd just go on an island and just do it. So, I'm lucky to have a partner like that, I would say.

Yeah.

So, that helped as well. So, like, when we figure out real pain points, even right now when we do, like, when we see that it's going to drive revenue, we just go into total execution mode. Jack, especially more than myself. And I think that combination of us foregoing a little bit of salary in the beginning and doing that got us to profitability very quickly.

Yeah. Who did you hire then as your first kind of couple hires?

That's a good question. So the first— OK, the first couple hires were 1 or 2 engineers. And then once we started really getting sales going, like, I was doing sales. I was doing a bunch of stuff, but like sales and then obviously like implementation. So the next thing was like, I'll continue to do sales, but let's get someone to do implementation and customer success. So that's— and that's the same at BloomNation. It was almost those same hires. Like, we didn't actually— We hired a customer support success person before we hired another salesperson, because for me, I was doing both. And I'm like, which one is more important to give up first, to delegate out?

Yeah, that makes sense. So with that company then, so with Whippy, I'm trying to think of like, you have this idea for it. Was the initial product— you offer a lot of things now with the product. Obviously, it evolves over time.

Yeah.

I heard, I think, some podcast, it was like just a text. Text was the focus? SMS was the focus? Or what was the original?

Yeah, that was. It wasn't the original. The vision, we knew where we were going. But the question is what what people pay for now. And what we realized is on the paradigm of email, voice, and text, if we added some pretty cool features, the people we're talking to are willing to pay right now for text. And also the other reason why texting worked well for us, and I don't want to get into all the details, but, but there's this regulation that changed with the carriers called 10DLC, and that made texting price go up.

Mm-hmm.

And so if you're gonna pay more, you want a better software. So that kind of was like a good thing to happen to us and to double down in texting. Because I think we, we do, I think, have the best platform for texting, texting automation, texting chatbots, you know, all that stuff around that. And so that change in US regulation actually helped us capitalize on the SMS— I would call it chaos.

Hmm.

And then when we got customers in just for texting in the beginning, we're just— we would, we'd work, and I've been saying like hundreds, right? We'd figure out what are the other pain points that we could kind of address that texting would work well with. So when we build products, even though we look like we're insane, like we have texting and then we have a product called Voice AI that will call you and you train it.

Yeah.

And then we have VoIP, which is phones, but we realized having them all in one was more powerful than having them separated. And so that's kind of been the principle that guides us to make products.

With that too, so did you nail the customers right away in terms of like the actual, the ICP that ends up being what you have today? Did you nail it right away? Because you're always optimizing for whatever's gonna bring in money because you're bootstrapped, right?

Yeah, yeah.

Was it the same customers then or has it evolved?

So I think the answer, that's a good question as well. I think the answer to that question is for me, I take chaos as the CEO. So like, I still today had 4 demos myself and we're like, you know, let's say 40 people. And they were just totally different personas. And what I'm trying to do is fish for something that actually is a real pain that I think we can scale.

Yeah.

I still don't hand it off. I try to get the next 10 customers myself. But at that point, we like create like an ICP and a persona and like document it.

Yeah.

And then I go to a really good rep and I say, you take it from here and I'm going to go fishing. And that's again, going back to Bloom Nation and their name being Promenade Group. They wanted to do that, but it was probably later in the game where they wanted to— And so when we do things now, we try to create stuff and like this one vertical and this next vertical and this next vertical. And that's right now. That's my job. My job is to take calls back to back to back. Sometimes have nothing to do with it and try to read through the BS and see who is a real product market fit and how much will they pay and what can we build? And then and then create some process that's somewhat repeatable and pass that to a smart person.

How much of that is from Bloom Nation and like? that experience learning and how much of that's from your poker background and you're just, yeah, always analytical on things anyways?

Yeah, I think, I mean, honestly, probably even going farther back. Like, you're in LA, so you get this. I don't know where the viewership is, but like, we're Persian, right? I'm out here and Persians out here hustling and they're out there and they're selling when they're kids and, yeah, and they're competitive. And, you know, so for me, even before all that stuff, like, I used to buy baseball cards. I used to go to the trade shows and see how I could trade up cards and And I actually even had— very quickly I started having a booth at the trade shows.

Amazing.

And I was selling, and you know what I mean? And so like that world has always been kind of part of me. I think the World Series of Poker helped a lot, and just poker in general. And I still play it here and there because you just— you have to have a gut for certain things. And gut to me is like you see pattern recognition, you see certain things and you calculate, and that's analytical.

Yeah.

So I think it's a combination, but I don't know. I mean, I've been trying to think about this myself. Is that something you can train? And I think to a degree you can take it from like 1 to 10, it's very hard to take them from 0 to 1. I think that person kind of has to have a little bit of it for you to take it to the next level.

Yeah, it's funny how many entrepreneurs have that type of experience, being a kid selling something, whether it be baseball cards trading or the lemonade stand classic thing. So many. I write these deep dives on world-class founders, probably done like 60 or 70. And so many of them have had something as a little kid they're selling already. It's like that experience gets taught early and you kind of just carry that over when you learn other skills to layer on top of that. So then you kind of become unstoppable in many ways.

And I think, to be honest with you, like, Kudos to you here. Like the questions you're asking are great questions, right? And like you didn't just come here right now. I'm assuming. I don't know. Chatbot or genius. Yeah. And you prepared because you're taking this seriously. It's not saying I could train in you. Like you came here because this is what you're passionate about. Maybe you had to do a little more work than you wanted to, but you're asking the questions here that are super impressive. And like that makes me want to tell my friends about that. That makes me want to invite other guests to tell them to talk to you. So I think Again, we can get there, but you have something in this world that you're bringing here to this podcast that I just probably couldn't give you if you didn't have it.

Yeah, and everyone has obviously something with that in terms of their skill set. And it's a mixture of like, what's the self-awareness on your end to know what you should be doing? Or within a company itself, what should you be doing? Which company should you be building? It's all these different like layers upon that. And then it's like, okay, for me, it's always curiosity. So curiosity drives kind of everything. That's why the podcasting world is perfect because I'm like, I could ask questions for like 8 hours and not get tired of it. And also combining curiosity with business, I'm like, those are the passions. So then you're like, oh wait, all these things combined make it work. And then I talk to these crazy chaotic founders, which is a perfect mix of all these things, and that's what I love. With you guys, with Whippy, so when I got the email, I was like, hearing about you guys, I think you were doing like millions in revenue already.

Yes.

This is 4 years in or something. How long did it take to get to the first million in revenue? And what was that feeling of like, we bootstrapped this thing, To getting to that point, knowing that we have a much bigger vision, obviously.

Yeah. We— I remember at Bloom Nation, when we got to a million, we celebrated.

Did you? Yeah.

I remember here, we didn't even think about it.

Like, all right, on to the next one.

Didn't think about it. Like, we didn't even think about it when it— in our Stripe account, it passed. So, you know, I can't even tell you the moment it did, but I realized when it did, I don't even think Jack and I talked.

Hmm.

I think how we got there, is, so someone at Bloom Nation and to anyone that's starting a company, you probably have to get lucky and hit a big fish somewhere out there. So in both Bloom Nation, here with Whippy, we've always been lucky to get like an early client. And that's why I'm saying I still take those calls that you never know. Think about like, imagine there's a, I'll just take this, like a podcast studio that needs automation or whatever. And all of a sudden you start vetting them. You're like, wow, this company is huge.

Yeah.

And they're interested in what we're doing. You generally need to, and the only way to get there is just lots of conversations. And by the way, the big fish that we hit here, so to speak, was a cold email I sent out to a bunch of people. So you still need to hustle. You still need to cold call. You still need to email. You still need to jump on demos. And I think one thing that Jack and I do a good job of here, that I wasn't doing as good a job at BloomNation when I left, is we still do those actions ourselves.

Yeah.

And if we can make a call, if we can make an email, if we can go to a trade show and talk, if we can still sell, Then no one else can think that they're above that.

Yeah, that makes sense. With Whippy, what do you want this company to be? Because you've done the venture thing already with Bloom Nation. You bootstrapped this from the beginning, maybe some of your own money a little bit just to kind of survive. But where are you trying to get to with this company?

So, I think, I mean, I think we can get to $10 million pretty quick.

Yeah.

But I think when most people start comp— and that's what I'm saying, like, I don't know what that number is. You know better than me. But like, when it's $10 or $20 million, you have good growth, you have a big addressable market, you have good net retention, those stats that people care about. Like you finally get in that breath of conversation where you can get closer to that potential exit. But I don't think that's what we want. I mean, it's just good to have that option.

Yeah.

I think Jack and I want to just continue to work with each other. And as we build more and more products within this ecosystem, we think, you know, it can be a $100 million or a billion-dollar AR company if we execute correctly. When we talk, the two of us, we don't actually ask if that's a possibility. We're just like, will we execute on— because someone will.

Yeah.

And so I think that's the direction we want. And the way we set it up is to do that, because even if it doesn't, guess what? That second option is probably not gonna be that bad.

Yeah.

But we do think like that. But I've convincingly learned myself that you don't need as much venture as you might to get there. And this is a hard company, by the way. Like, it is like we have VoIP, we have email marketing, we have email sequencing, we have SMS, we have AI chatbots. Like, I would never have thought we could all build all of that without raising venture.

Yeah.

There are things that we've done that are very creative. And that's why I'm saying, like, I've pretty much built and trained a success team that's based in Argentina, who I love. And I call and it's like, we talk about football, we talk about poker.

Love it.

But I had to do that because I just couldn't afford to actually do that here.

Oh, I totally get it.

So there's stuff like that that we realized that we had to do. To get to this point.

Yeah.

But I think that just made us better.

We can't just gloss over that, because I think it's important for any entrepreneur trying to be scrappy as well. It's like, what other creative ways have you grown this company? Because I feel like you want to share how much revenue you're doing today.

Probably we're doing— I think we're somehow probably close to probably somewhere in the $4 to $5 million.

So $4 to $5 million in revenue in like 4-ish years.

Yeah, and I think it was probably slow. It was probably like, you can think about it, half, then 1.5, then— 2.6, then 4.3, something like that.

Which is phenomenal for any company, especially a bootstrap company. I mean, obviously, depending how much a company raises is going to dictate. But like, someone trying to get to a seed round, they're at maybe a quarter million in revenue. If they're trying to get to a Series A, now it's $1, $2, maybe $3 million in revenue. And that might be 18 months in, 2 years in, if they've gotten some traction before that. But I'm always curious about that because like, this company can get much bigger, obviously. Are you ever going to raise money? Are you going to continue to bootstrap?

Well, I'm convinced we should have had— we should have been farther along without money as well. Like, there are probably things that I think we could do to actually grow that faster and that money isn't a constraint.

What are the things then?

I think on the sales go-to-market side, I think as you scale, you know, you always have those scaling problems. But I think it could be training. It could be like more documentation that we should have kind of put together, probably doing partnerships earlier. I think from our sales side, I think honestly, like still being a little scrappier. Like I'm telling you, like, and I just talked to the reps today, we were at a show in Miami and I said, hey guys, how can someone walk by you with a badge that says they're a prospect and you just let them walk by?

Yeah.

If, and this is, I was like, if we were back in the day and we're at a club and someone walks by, that's never going to happen. You can't sit at my table. And I know that's, that's an effed up way to think about it. So, you know, it's kind of—

What are you, a founder or something?

Yeah. But I'm just saying like, that to me is money and they're walking by and we have a really good product. And it comes more from the sense of like me thinking 2 or 3 years ago, we had none of this stuff and we still got revenue. So, and I think also on the customer success side, like getting cross-selling, like there's a whole bunch of worlds. We don't even have a marketing team, right? SEO, it's all outbound. So inbound. So there's so much more I think we could do. To your question about raising money, there might come a time. I mean, it will always be about 2 things as a founder. One, the expected value. Like, that's a poker thing, right?

Oh, of course.

So like, if we actually took money and that could supercharge or probably help us buy a company that would do that, that makes total sense. And then the second thing is optionality. Like, does it increase our optionality? Does it decrease it? Right. What are the terms on the term sheet? So I think all those conversations are real conversations to think about, but I think you raise when you really have to, to supercharge the business, not just when you want to or when you think it's cool.

Yeah. Supercharging the business. And also depending on the market and situation, do you need to do this for a certain opportunistic reason? And if that aligns with what you're trying to build and what you're okay with. It's like, I just talked to Sean Sheikh from Pivot Seed. So, formerly Pivot CMO, now he's managing partner at Atli. They've done $300 million in deals. They've acquired 13 companies since 2021 when you guys started as well. And talking to him, like, I was like, what do you want now? He's like, I'm optimizing for freedom. Like, he was on the cusp of buying a winery and just chilling out. And instead, like, a deal came through and like, fine, we'll do it. We'll do this deal. Which then him and his business partner were like, should we do more of these deals? That was fun. And that's how it kind of grew. But he's optimizing for freedom. You talk to like, like very polarizing. Elon's not optimizing for freedom, obviously.

Yes.

But like, there's a whole spectrum in between that.

Yes.

What are you optimizing for? What do you care about as you're building Whippy?

I think, I think it's probably a combination of the two, right? Like, I don't want to not work. So, like, I work a lot. Jack works a lot. Our team works a lot. Like, that's what you subscribe when you come to work with us. Not to the point where you go crazy, right? So I think my dad said it best. Like, my dad's a doctor, he's a gastroenterologist, he's, uh, just getting to his 80s. And I even said like, oh, if we could just, you know, retire, would you? He said no. So I, I do think that like that's not what I'm interested in right now. Yeah, like even if some— if we did get $50 or $100 million, we bought a house and stuff like that, I'd probably get bored as shit.

Then what?

Yeah. So I don't think that's it. I think it is kind of pushing towards a vision. And I think again, just like simplicity is like the people I work with, I enjoy, like we're in a good place. I think it would be cool to have a little bit of balance at some point, right?

Sure.

So that you can think about a family or you can think about other things that are important or spending time. So I think like a touch of freedom, but I also think I just want to continue to scale this, I would say.

Yeah, and with the people side of it, you mentioned before, like, Okay, if someone's at a trade show, walks by their potential customer, you don't want— don't let them just go by without saying something. How do you vet for hiring that person?

I think what I learned— so it's hard to, and I feel for those. I feel for our reps. Yeah, because I come from a sales background and I just believe in just straight beasts, right? And by the way, like, it's not even necessarily— I think like some of the best reps I've ever had are females who have a good sense of just going up and knowing that. Yeah, I think It doesn't matter. I think in the end, it's hard to vet for that. What I did do this time that was really cool is I decided on someone's first day that we're hiring just to bring them to the show. And that was awesome because we actually noticed they had as good conversations as like anyone there. Like, they didn't know as much about the software.

Sure.

But I would look over and I would be like, dude, he— I don't know if he knows or doesn't know, but he definitely is portraying that he knows. And people are listening, right?

Yeah.

And you could see the conversations and people are laughing. And, you know, I come from poker where you can understand that world and body language. And like, that was a good first test, I would say. So one of the things I've been thinking about since then is if we have any type of event, just bring a rep there. The second thing that we do at Whippy as well, which, you know, some people do, some people don't, is that now we start a lot of people on contracts. So like, there's a new sales rep we just hired, I think yesterday. He's got a 1-month contract just to see and just to make sure like, hey, is this a good fit for him and for us?

Yeah.

All the engineers we have start on a trial on a project.

Love it.

So that's another way that we try to like find, find that out. I think, I think it's difficult, but you generally tell right away. Like, I've had some hires where in the first week I was like, Jack, oh my God, this is gonna be amazing. And I've had some hires where in the first couple of weeks I was like, wow, there's so many red flags. I'm like, but you can't, you have to be better at hiring, but you can't be afraid to let people go and move on. And that's something I think we've learned. You have to kick yourself because you're the one that hired them. So that ultimately falls on you and you have to ideate. But I think the worst thing you can do culturally, and I'd seen that before at our old company, is have someone that can be somewhat cancerous to the company. It doesn't matter how much revenue they bring. That's a disaster.

Yeah, that makes sense. So one thing you said before too, your team is distributed. So what's the makeup? Is it in US, in LA versus Latin America? Yes, it is. Because actually, I hired a writer for the first time for Just Go Grind, and she's in Buenos Aires. And she's phenomenal. And I'm like, this is insane. Why didn't I think about this earlier?

Yes.

And more companies are probably thinking about that. How are you thinking about that with Whoopi?

Well, first of all, just to show you, just talk about Buenos Aires. There's a girl on our team. She actually had to come to the US. We flew out her. So today, just 2 hours before I met her for the first time.

Oh, wow.

She's from our team in Buenos Aires. I'm going to Buenos Aires next month for 2 weeks. I mean, you have to invest, I would say. Of course. And and there are other people in Latin America. So a lot of our supports in Latin America, a lot of our engineering actually all our engineering is in Europe. It's it's it's it's mainly because my co-founder Jack's Irish and he's in Ireland. So when we started this, he was like, "Oh, I'm gonna live in LA," and then he's out there living with his girlfriend now fiancée. So congrats to congrats to him as well. And so that's where the engineering and then the sales usually. And some of the C-levels are usually— they're here in the US. I would say my dream would be to have an office, even though we're distributed. And some founders are here saying, hey, um, I love the distributed work, you get better talent, which is true. I think that is one advantage we had at Bloom Nation, like sitting there and being able to talk to people and see people, I think is something that's super valuable. So at least with sales, I do think sales is huge. Like, you're getting rejected, you don't want to be like By yourself, getting those cold calls—that's miserable. Yeah. So I think for sales, it does make sense. Hopefully, in due time, to have an office out here, or maybe one or two offices in the U.S.

where people sit next to each other. That makes sense. Yeah. There's so many opinions on that. It's like whatever works for your company. Because I mean, like I said, I just talked to Everett from Roe, and like they're very much in person. Like they love that culture. Then I talked to Tyler Dank a couple years ago from Beehive. They're very much so remote.

Yeah.

And he just like loves that. I think he's in like Colombia or something. So, like, you see that difference. There's no right answer, I guess.

But my caveat to that would be what we're doing, which is good, is like we decided instead of distributing in Latin America, we have an office in Buenos Aires and there are 8 people there and they work together. And instead of distributing, sales and engineering is, for example, based in Ireland. So, even though there are pockets of like 6 people.

Yeah.

So, I think it's like more of like a hybrid. If I had a dream, if you told me, hey, we could have all these companies sitting in LA with me, I would choose that over anything else.

Yeah, I agree.

Like, I don't want to BS you. But if not, I think it'd still be good to have these pockets because it helps. Like, it helps not only for a CEO, it helps not only for that culture, but it helps because you get some of your senior people to be like, you know what, this person's an all-star. I'm seeing them go out of their way. This person is— I'm just seeing in person, they're just not picking things up. So I do think even just having little pods makes things more transparent.

Today, so you're like 4-ish years into Whippy. Obviously done, you know, $4 or $5 million in revenue at this point. What's the biggest challenge that's like next for you in terms of building this company? The AI has taken off over the last few years, obviously. Like, I don't know if that has a tie-in to it, but like, what's the biggest challenge you're thinking about today?

So I think the $4 or $5 million actually surprisingly, we just debuted our AI agents. We just debuted VoIP right now. Like, we haven't even charged for it because of our clients. So I think the first thing we have to do is take that $5 to $10 within our own client base. Like that we should. Like we're putting all this stuff out, we're just coming out with it. So I think upselling current customers and making sure the product's stickier and gives them more value is a quick way to get to 10 million. Yeah. Without ever selling a new person. I think the other thing is just like marketing and messaging. When you're doing VoIP, when you're doing workflow automation, when you're doing these AI agents and you're doing them in other industries, you— I think you have to get really good about messaging and marketing, which is not something I've done a great job of. And I think a lot of that will come from some branding and like honestly just getting to these trade shows, putting in more face, listening to your customers. And then I think scaling kind of unit economics of sales is going to be something that we have to get really good at. So for those that don't know what that means, I mean, you want to add 10 people, but you don't want to just get, you know, if you want to double your sales, you just don't want to get 30% more Revenue. Yeah. So I think those will be challenges that we face, but I'm excited. And I think again, that multi-product pronged approach actually really gets us jazzed because we realize in one industry you need to have— and this is a cool, cool thing I think about— you need to have like the sexy object. So in one industry, it's actually SMS. It's crazy. In another industry, it's like integrated VoIP with transcriptions and call recording. And another one, it's AI agents. And all you need is one to get them in the platform, and then you do the rest. You upsell them inside. And it's been so awesome to have these different products. I've heard of it before. Like, someone's called it like compound startups, where you have these different products. I think Rippling is the one where Rippling has HR and device management. And when we saw that, a lot of investors said that's a bad way to go. You need to be focused. You need to be really good at one vertical, one product.

Okay.

Like, that, that's the way that At least investors thought a couple of years ago and back to when Bloom Nation. And I think Jack and I just like shrugged that off and we said, we're going to do a whole bunch of products well. And if we do this correctly, it's going to be dream for scaling. And so I think we're in that position now. And again, I have to take my own advice. It's all about execution. Yeah.

Which is everything. Yeah. Obviously, the Uber idea you talked about before. It's funny because having— so I went to USC for business school. Yes. And met some very interesting guest speakers. Yes. One of them is Travis Kalanick. Oh, wow. And so it was like, And I've seen the shows and all that, and I just get excited because I think he's like a tremendous executor.

Yes.

And if people see how he executed with Uber going city by city, the strategy involved in all of that, you're like, you could never build Uber. Like, someone else could never have done the same thing.

That would have been hard. So, I want to throw a shout out to Joseph Amin, who's my brother's father-in-law. I just think it was going to be hard for him to keep up with someone like Travis, right?

Yeah.

So, but they have the idea. But no, I think the execute, it's just insane. I think at the end of the day, when these people exit, Yeah. And they're sitting there. No one else. It's like that iceberg thing where you see that one little piece, but there's all this stuff. The iceberg is probably much deeper than that poster shows you.

Yeah. No, I agree completely. One thing I'm curious about with having built this company after Bloom Nation and playing poker before, like, how do you learn today in terms of, like, becoming a better founder? Like, is it— do you have a peer group? Do you— are you— is it books? You're a voracious reader. Like, just how are you learning, growing? What is that for you?

I think that's a place where I need improvement. So I've heard—I wouldn't say I've taken advantage of—but I've heard a lot of people who have like career coaches or executive coaches. That's helpful. I mean, my best way—and I know it's hard—is just having these one-on-ones or these quarterly meetings where it's all about them giving me feedback. And the questions really are that I ask are like this in my you know assessment one-on-ones. It's just like where are you at one through ten with the company as a whole? And they're like I'm at a six. Okay, last time you're at an eight. What's working well? And they'll tell me, but I'm like, how do we get you to a 10? And that just unleashes things. Well, if I'm gonna get a 10, I need this, this, this, this, this. And that helps because that's an easy way for me to get real feedback. I think the second thing is you have to be approachable. And like, maybe this is where poker makes you not too emotional, but when they give you that feedback, you have to just like take it in and actually show that you'll, you'll, you'll actually implement it.

Yeah.

And I think when you do implement it, and like someone recently was like, we need someone in this position, I'm sinking underwater, and we did it. Other people are like, oh man, if I actually say what's going on, there's actually going to be a founder that's actually going to help. Through that channel of transparency, they tell you where you're effing up and where you're not. They help you. So that's been the closest way I've gotten to probably improving as a founder. I probably could do a lot more.

I mean, there's always more to do, right? Yeah. There's always more to do. Everyone has a different approach. That's why I'm curious. Like, I think— so if I look at like Patrick Collison from Stripe, I look at Christina Cacioppo from Vanta, some of these people are like, Very much voracious readers, learning from history. That's just about they're wired though. They've been wired that way from like birth, it seems. Yes. So like, but everyone's not wired that way. Some people are; it's more of like they want feedback constantly. Other people, they have peer groups, whether an actual peer group or they just have their homies who are founders, you know? Yeah. There's no right way. I'm always just curious how people are approaching it.

I think the other thing I do just naturally in the sales world is I talk a lot. So if I have questions, I always call people up. I'll always ask people to dinner. I'll, and I think that's a big thing. Like if anyone. You know, you've heard this. I think I even saw it on one of the podcasts you did. You know, when you ask for advice, they give you money. When you ask for money, they give advice. I think that was one of yours I watched. So, like, I just think if you go out there and ask someone and just talk to them, things are going to happen. Yeah. Like, people don't know, like, how important that is to just have real conversations and not be pushy and ask people for advice. And I think that's something where I'm good at, where just like I'm used to just like picking up the phone and dialing. And that's one of the core values I would say at Whippy. that I've implored, even though we're an AI automation company.

Yeah.

Human touch is really important. And from our support to sales, I always tell people when they have a question, whatever, like pick up a phone and ask someone. And so I think on this side, you know, one thing that we, you know, people do to kind of get that feedback loop going and just get more information is just calling someone and actually just talking to them, which sounds insane. And I think for me, when I look for guidance and help, I'll just, sometimes I call former employees of mine. Like this weekend I was redoing our comp structure and I was like, what do you think about this? What do you think about that?

That works.

It helps me.

Yeah, well, especially having been in the game before, you can rely on that. You've been in it, you've raised money, like, like you've done enough where you have that cachet to be able to do that.

But the, the thing is, in poker there's so many books, by the way. Yeah, I really only read one or two.

What'd you read?

I think I read at that point, like, there was like Doyle Brunson's Super System books and there was like one other Like, I learned by going to the poker table and then just asking people incessantly, well, I'll buy you coffee, will you tell me how you played this hand? So I could have read 100 books, and I think that's how some people operate best. I think mine is like, you know, just you got to put a little bit of money and a little bit of skin in the game right there, and you'll learn by doing.

Yeah, I mean, there's so many ways to go about it, obviously, um, in terms of learning and growing. It's ultimately like, what is the company growing like? But how do you prepare yourself for like that next step of the company. 'Cause every company, as you progress, it's a new company. You have new people, but also new challenges, new customers. Everything's changed. One of the last things I'm curious about with your company, given this environment, AI and everything, how do you stay on top of all that? Like, how do you think about the developments in AI and how fast everything's moving as this company? I'm just curious about that.

Yeah, yeah. I think our principle has been pretty simple. Build things that are functionally relevant and are low-hanging fruit. So I agree, like there's some wild things going on in AI. I mean, when we were sitting here right now and we're chatting, yeah, yeah, the gentleman helping us, you know, put this together was telling me how you can like feed podcasts and AI agents and it edits and creates real— there's so much wild stuff going on.

Crazy. Yeah.

For me, I just look at my customer base and I'm just like, what is the lowest hanging fruit of something that we can build that will cut that 30 or 40% of time that's just so obvious and transparent and can be verticalized to other industries. So like a lot of times it's simply like in staffing, it's just like, how do you automate the interview questions I have and fill in my system?

Yeah.

Data entry. So when we think of AI, I know it's gonna go to wild places, but I call it functional AI. There's this wild perception of AI and it's gonna take over the world. I'm only concerned with what can actually take away 50% of your workload that even you would agree Is just dumb for me to do.

Yeah.

And that's the place that I think we focus right now.

Yeah, that makes sense. Like, useful applications.

That's it.

For your current customer. It's funny because I talked to—

Going back to the Amex, will you pay for it? Well, right.

And like, I talked to my former boss, Gayle, at Vitalize, and that's like, she always is preaching that. It's like, she sees AI companies all the time. Obviously, she's an investor. It's like, does this help someone? Does like, are they going to pay for it? Like, there's so many things that people get like, oh, but it can do this. And it's like, Okay, and?

And I think it's funny, maybe I'm wrong, what's Gail's last name? Wilkinson. So she actually was a classmate of mine at Booth. Really? I think so. I think Gail was. That's hilarious. I think we'll have to look that up.

Oh my God, yeah. Well, that's the thing with AI and these things though, the practicality of that is super interesting to say, okay. And we see it now, 'cause if you're on Twitter at all, you can see all the things being built that you see the outliers, right? Yes. So some things like take off and get to $20 million revenue like 3 months or something. Yeah. Crazy, right? If they solve a problem and a need.

What are your thoughts? No, no. So I'm seeing this. I don't know if people watch it. I'm seeing this revolution now with these like AI SDR softwares. Yeah. And those are the ones where I think, and I'd like to speed ours up. I'd like to go 5 to 10 to 20 really quickly. But those are the ones that like in 8 months are at like 20. But what I've seen at least is the retention of a lot of those softwares isn't great. Yeah.

Which is a whole other discussion with AI. Yes, it is. And also as it's progressing, everyone used to think like, what's the moat within AI? And it was like, oh, like OpenAI's models and stuff, like they're gonna crush 'cause of that. And then it was like, well, I think DeepSeek came along and people were like, well, maybe it's not that. Maybe these wrappers are okay. They actually are useful applications of it. It's so crazy to think about with that. I know we're outta time. With Whippy though, I'm just curious, who is it for today? What's the pitch today of Whippy?

Yeah, I mean, I think any small business that, I mean, right now the main use cases are staffing, pharmacy, insurance, financial companies. They're more businesses in person, I would say. So less so like SaaS companies. Those are people that have issues with SMS communication. And we have, we're like modularized, almost like Notion, we have building blocks.

Yeah.

And in most industries we're scaling, we've already figured out the perfect use case. But yeah, we continue to see people come in, and I think the real thing is more a consultative approach. So if you're coming in and you're an insurance company, your biggest thing is people are not opting into their insurance in time. We'll generally sit with them, understand the problem, and like put a little A/B testing and see if we can figure out, you know, how can we actually get the results they want? And then we'll just like blow that out of the water. But I think anyone in those, those, those worlds, like even my crazy enough, even my dad is GI center. He now uses Whippy for a certain certain workflow.

Crazy.

But usually companies, I would say, you want companies that have multiple, a good amount of users, because it's a team-based software. So that's one. I think real-world businesses. So when you think roofing, HVAC, that's the world we're kind of in now.

Yeah.

Still not in that world of like the Fortune 500 and stuff like that, like true enterprise. And that's where we're at now. But we built a fully open API. So if someone has a homegrown system, they're a much larger company, we can take those same best practices and workflows to bigger companies.

Love it. Where do people go to learn more about it? Also connect with you if they want to.

Yeah, so, um, www.whippy.ai. We called it Whippy, um, because I have 2 Whippets that are these fast dogs. Yep. So whippy.ai, and you can find me on, uh, LinkedIn or Instagram or whatnot. But, uh, David Daneshgar. But the best way is just to go to whippy.ai. Check us out. Cool. Thanks for your time, man. Yeah, thanks. Enjoyed it. Have a good day. Thanks.