Jason Kirby: Hey everyone, this is Jason Kirby again with Thunder.VC and your host of the Fundraising Demystified podcast. Today we have David Daneshgar with us from Whippy.ai and we're excited to be having you to the show, David.

David Daneshgar: Thank you, Jason. Thank you for having me. Excited to talk about my two stories and any information I can pardon people that are looking to either raise capital or not raise capital. Excited to speak to that.

Jason Kirby: Awesome. Now we're excited to have you and excited to have you kind of share your story. You have an interesting background having played professional poker and then gone on to raise venture capital and now starting a bootstrap business. So it'd be great for you to kind of just share your founder journey and kind of what led you to where you are today.

David Daneshgar: Yeah, yeah. Thinking about how far back I can go, but, well, I mean, I guess I'll try to be quick here, but yeah, I went to UC Berkeley and they actually somehow taught a course on poker. At that point, this is right in the heyday of when Chris Moneymaker won, so I'm dating myself. But we taught statistics and probability of gaming, so that got me super interested after I went on to be a professional poker player.

David Daneshgar: I ended up winning one of the World Series of Poker events in 2008 and was interested in the business side of stuff. So I became very interested in... I actually became friends with the owner of the Lakers. His name is Jerry Buss and wanted to be a general manager at the Lakers, but ultimately ended up getting his letter of recommendation to go to business school. I went to the University of Chicago and that's where myself and some of my buddies from...

David Daneshgar: from college started a Bloom Nation, which started as a marketplace for local florists. Think of like Airbnb for flowers, Tello floor and 100 flowers, they were a broker. So we weren't getting delivered what we thought we were getting, but it ended up becoming a backend software. So the florists actually kind of had their own Shopify and this is early on. This is probably 10 years ago where they can make their own websites, their own marketing tools. So that was, and we grew that through

David Daneshgar: a lot of outbound sales. But to start that, and I know that's something you mentioned, one of the first things we did when we got the MVP was go back to play poker tournament, won a 30K poker tournament. I know a lot of people, it's not as dramatic as it sounds like, we weren't not gonna move forward if we didn't, but that did make it easier for us to hire our first outsource dev team. Was at Bloom Nation up until a couple years ago and decided to take a little break. And one of the engineers that was there,

David Daneshgar: His name was Jack Kennedy. He also left around the time I was leaving. He actually wanted to stay there and forego finishing his masters. He was at UCLA doing his masters and came to me and I said, well, I'm actually just gonna take a sabbatical. And so he went back to finish his masters in Ireland where he was coming from and then we we linked up two years ago and we're really interested in like communication automation. One of the biggest things that I learned at Plum Nation, which was obviously as I mentioned venture back

David Daneshgar: was how big like the addressable market size was, or how important it is to build infrastructure to kind of scale. So we're so focused on local florists, and that's what investors were telling us at this time. You have to be the best in X. But I think at WIPI, we realized that a lot of people needed AI-based communication, or they needed email and SMS automation, or they needed deep integrations with a database or a CRM that they weren't getting from that. So that was harder to focus on. It opened up a lot more doors as we scale. And so,

David Daneshgar: As I mentioned two years ago started Whitby and now small team, I think we're 13 full time and I've never raised any capital. So very different to my story at Bluemation where I think in total we've raised over 20, 25 million.

Jason Kirby: Yeah, so you raised $25 million for Bloom Nation, but for Whippy, you've completely bootstrapped, correct?

David Daneshgar: Completely. I think, I mean, I think maybe, and this just shows you it's possible. I think maybe in the beginning I issued myself in terms of a loan to the company, but a very small loan. And part of that actually, which pushed me to do that was that I hadn't exited a bloom nation. So I think it's a little bit different than I know in your own store, you had some exits. I think if you do get this big exit,

David Daneshgar: I think I've learned that sometimes, not to say you'll start things irresponsibly, but you're not looking at all the little things that may drive a company, because it's not life or death. And here, we had to start something else while I still had a lot of equity in another company where I didn't have, I wasn't sitting on a huge amount of a capital exit. So that made us get crafty. And I think it's really true, the saying that people give you, which is you just find ways to do it, even if you can't. And so I think being bootstrapped and also having that experience.

David Daneshgar: I found crafty ways to make sure that like directly or indirectly every decision you made like had good unit economics had because at the end of the day it's it's that there's nothing else but revenue that drives the company if that makes sense. There's no other external source of capital.

Jason Kirby: Yeah, and honestly that's that's in fashion these days, you know I think after the big bubble in venture capital over the last couple years in 2020 2021 you know, we're seeing a refocus and a realignment on VCs actually wanting to back more bootstrap businesses people that had to get scrappy that were more sustainable That had actually figured out their unit economics before raising venture capital so that when they put in a dollar they get three dollars back or ten dollars, whatever

metrics are. And so I think it's interesting to hear that story. And also, like, you know, probably a lot of founders would think, oh, he probably made so much money on Bloom Nation and it's so easy for him. But like, you know, here you are, like sharing your side of the experience of like, no, you still had to kind of bootstrap, you still kind of had to make things where it gets crappy. So I'd love for you to kind of share your experience in the, you know, from Bloom Nation in terms of why you wrote Raise Capital, I believe A16.

ACX NZ was your seed investor and then you went on to raise subsequent rounds. So kind of walk us through a little bit about that history and how you guys want to go about raising money and now all these years later reflecting back on what you would have done differently.

David Daneshgar: Yeah, and I appreciate this podcast. I think sometimes like you said, you only hear, I don't know how many times I go on LinkedIn, even between ventures when I was starting again, it's hard to start because you see all these success stories. But I do think, you know, that little poster where there's this huge iceberg and that little tip on the top where you see the success, how much goes underneath. So I'm hoping some of that would be shed here with your other speakers. In regards to Blue Nation, it was a cool, I went to a cool, fun story.

David Daneshgar: I went to the University of Chicago and in the university, my two co-founders at the time were playing with this idea of the marketplace, like Teleflor and 1-800 Flowers wasn't servicing them when they were sending to their girlfriends. And so, it first of all made my experience at the University of Chicago much better. But when I went on, so just so you know, the first actual round or first amount of capital was the school, because the school had their own business competition, backslash, minor incubator.

David Daneshgar: And so I think we won the school competition. And that's a great program, by the way, like GrubHub, Braintree, a bunch of the companies have come out of that same University of Chicago, excuse me, University of Chicago program. So that's been a big feeder. We came here and then really quickly, we did get actually start doing some fundraising. And I think the main reason why, which is very different, is we had revenue in a lot of customers. Like again, we were hustling and we had, I think at that point, hundreds of florists using us.

David Daneshgar: and some nominal revenue. Now, before that, the story that you know, to get the MVP, none of us were technical. Whitby and my co-founders technicals made a huge difference in terms of like balance of responsibilities and being an expert. But we had to go out to an outsource agency which created technical debt and problems. But also at the same point in time, like maybe at that point in time versus now, we couldn't get up and running it. Now there's so much no code in all these solutions. So yeah, we got BlueNation up and running.

David Daneshgar: We had some traction going. We had floors that were signing up. And then I think, yeah, it was Chris Dixon actually, who was a seed investor, who wasn't at Andreessen Horowitz yet, who had then moved over, who brought us and introduced us to Jeff Jordan. We became very good friends with an investor in Andrew Parker, who I think at the time was at Spark Capital. And then Mucker Labs, we went through, we decided to go through the incubator, Mucker.

David Daneshgar: And they invest in us as well and they've been very successful. And so that's how we kind of raised that capital. We raised a one and a half seed at the time and then a five and a half million dollar round about a year, year and a half later where Ronnie Conway Jr. came in. And so that was all good. I mean, to be honest, it was really fun and all the stuff that you say makes the whole process a little more sexy. I think where it turned was when we realized that we were kind of like in today's world where we realized we were running out of runway.

David Daneshgar: and we actually had to have a recap. So that's a very different process. And some of the things that people experience now, which maybe no one experienced back then, it was in 2016 where there was this one period of time where it was a little bit difficult to get fundraising. And I remember going into like a board meeting or a visit and we're like, oh, by the way, we have X amount of runway. And the investor there was like, what the hell? You know what I mean? And so we went through that experience, which happened to talk about, I don't know if people here know about a recap, but essentially,

we had to go to our current investors and be like, this is a situation, we are a good business, but cash flow wise, there's gonna be an issue. And I think it's kind of like called like pay to play where the investors you'd have to follow on or forfeit some of their ownership. So that was also a little bit of a messy time. And it did give at least myself and some of my co-founders and stuff, I would say a little bit more of a hardest steal because we had to go through that heart attack where I think that's what's happening to people now, if I'm not mistaken, they're going through those types of recaps.

So we went through that in 2016. So I think that did forge some of the mentality that I now have on like never wanting to go back there again.

Jason Kirby: I think you hit it on the nail. It's what a lot of, I would say like series, people that were expecting a quick series B after raising a frothy series A, were in for, you know, and even like series C, like we're in for a rude awakening and having to deal with recaps because it just, everyone thought money, the money train would keep coming and everyone told them to burn at all costs, you know, grow at all costs. And, you know, now it just, VCs changed their mind and they're like, no, we don't want that anymore. We want profitability, sustainability, unit economic,

important things to have, but it just wasn't the part of the conversation.

David Daneshgar: I think ours was a unique company too, by the way. Sorry to interrupt you, but we were actually doing good revenue then. So I don't think we've ever, historically from implementation, and I think that has to do with the decimal market size, gotten a really good multiple. Whenever we were raising money, we were also producing revenue, but you're right. What ended up happening is our expenses were higher than revenue. So the recap actually made us think, okay, in two months.

There's a revenue stay here, but our expenses go here. And therefore we are like carrying our head over water. But we were today, when I see a lot of companies, it's pretty strange because they go through a recap, but like there is no plan. There was no necessarily revenue. Does that make sense? And here, the recap to me was almost like a float because we just need to adjust some things. And we were not to say we were fine, but what we had that luxury that I think other companies didn't because at Blue Nation's principle.

It was built the right way. It was built with that in mind. And so there was a huge dimension. I mean, if we had like something like Pipe or some type of like for your subscription software now, we would probably have been been OK. But it was a result of of of that and just timing.

Jason Kirby: Yeah, revenue-based financing is one of the amazing, there's a lot of debt solutions right now that have become very popular to kind of, if you were smart in this market to kind of manage and generate revenue and you just really need some time to get to break even like it's a great kind of stopgap and yeah, it'd be great to kind of share, you know, and hear from your side of just kind of like what happened after that, that recap because you know, it's

as far as it looks like, it looks like Blue Nation is still actively running and hasn't been acquired or hasn't been, you know, exit. So what was your, kind of what happened after that recap and then what's kind of been your exit journey out of your role there?

David Daneshgar: Yeah, so I mean, I think everything was great before that, but I think the recap was actually a good thing because it made us act more like an internal private equity company, right? Like we sat in our own, like, and that was cool. Like, especially for myself, my other co-founder, the one that was a CFO was more prepared for this, but I think for us, it made us understand like how to look at a P&L and like, like I said, like how do we actually, like, what's it we're buying this as an equity or an asset now, like how would we restructure this?

Jason Kirby: Thanks for watching!

David Daneshgar: You know how you actually have this, I know it's called a qualified small business stock, but you basically, you go and you file when you file C Corp, you file it 83B election. I don't exactly know if that's it, but like you get five years. Yeah, you get five years, right? And that was one of the things I'm Persian, so we don't like to pay taxes. So that was one of the things I would tell my parents. They're very excited. But like things like that mean that we had to actually redo that. Like we had to get ourselves to that. We issue stock to ourselves because we got watered down and we had to earn it back out.

Jason Kirby: Yeah, it's for QSPS.

David Daneshgar: For a lot of the former employees, not the current employees or former shareholders that couldn't play to pay or early investors, a lot of them lost a lot of equity. So that kind of obviously sucked as a founder. Where do we go from there? I think we got very fiscally responsible. Blue Nation is humming now. I mean, I know they raised, I left in the start of 2020. And I think in 2020, 2021, they did raise another round.

because there was a huge shift where people were starting to go more online, and so all these e-commerce platforms saw a boom. I don't know exactly where they are now, but the company, I think when I left it was like 60, and I think went up to 120, and I think heading back down maybe to 80 or 90 as people get more fiscally responsible. I know they've tried to double down on some of the stuff I touched on earlier, which was how do we increase our addressable market size? So I think...

Jason Kirby: Hehehe

David Daneshgar: they're trying to become a platform for the liquor shop, the butcher, whoever uses other platforms. Like they're looking at fragmented, the carpet cleaner, I don't exactly know. But yeah, I mean, the company is still there and I'm still an equity holder in it. I think when I thought back when I left and like the traditional, again, this is a great podcast. It's not always what the movie says. I thought, okay, I'm gonna leave and here's my big check and onto the next.

Jason Kirby: Hmm.

David Daneshgar: But I think that would have also done a disservice because I don't think I would have been as snappy or as an operator. Most people that run through that just can't get into the grind again. And I was hitting the cold calls again. Why? Because I had to. But I think that created a culture for us now at Whippy, which is kind of the way, like it's like someone who plays football and you have a chip on your shoulder, you really haven't won the Super Bowl. You've gotten close and maybe that will happen. And so I think that did create a drive in us.

Jason Kirby: Mm.

David Daneshgar: And yeah, the company's going well. There's actually some crossover, some of my old customers that are florists actually use my new platform, but it's totally been where I was all in or not. And I was on the board for a little while and then gave up my board seat. And I think that opened a new door where in the beginning, myself and Jack, it was just like trying to figure out, product market fit and testing things out and seeing what people wanted and.

who would pay for contracts before a software is out and that type of stuff. But yeah, I mean, that was a little bit of my experience there and happy to share anything else if you have any other questions.

Jason Kirby: No, I think that's an amazing story, especially because the ups and downs you went through with Blue Nation and then basically electing to start over again, even though Blue Nation is stable and growing and humming, you chose to start over because it was the right decision for you. You didn't get a big payday. Now hopefully maybe down the road or however things work out, that happens for you. There are secondary options down the road. But...

David Daneshgar: Yeah, I'm cheering for them, that's for sure. But I'm also cheering, I'm cheering also for myself. And I think that's one thing I can answer for other people that are even founders. I kind of think of like poker, because I know we can talk about that too, but I played professional poker at one point, been like, this is way back 2006, 2007, one of the top hold them tournament players. I think you need a couple horses in the race. And I think if one's going well, but you also don't think personally, maybe you add as much value as you can, or you may want to go somewhere else.

Jason Kirby: Yeah.

David Daneshgar: Like it's also good because that's going well, this is going well and you want a bunch of, I mean, not to gamify it, but a bunch of horses in the race. You wanna have different options or outcomes. And I think that's kind of what we're doing here with WIPI. We did see some things, at least me personally, whether it's from fundraising, whether it's on the addressable market, whether it's the customer base, that I wanted to kind of, how would I say that? Take those learnings and kind of try it.

Like, I mean, classic things to like when you're a SaaS company, you have an account management, you don't want to scale linearly with customer service, right? So we're kind of used to X amount accounts at another person. And we want to know how to, whether it's automate or documentation or, or certain things that like, you know, even you could even outsource some of that. And so I think there were things like that around the fundraising and mainly we'll talk about around bootstrapping and having your own destiny, be your own decision, which were some of the things that I was intrigued and trying in my premise with Jack for the next company.

was we just wanted something that could touch so many clients if it worked out. And that was hard because it was so broad that it's the opposite of what venture companies would tell you to do, which is like focus, focus, focus on being the best in one thing and one vertical.

Jason Kirby: Yeah, I saw that on your website. You kind of list a couple different verticals. You have a whole separate pitch for whether it's insurance companies or real estate agents or whatever it might be, and kind of tailing your message across each vertical. But giving you your tech can technically be applicable to multiple verticals as just a matter of positioning and making sure that that particular customer persona recognizes the value. And again, like,

Yeah, VCs typically want you to be perfect and down one lane, but the beauty of bootstrapping is you get to make the right decision for your business and the way you want to run it. And you don't necessarily have to worry about the venture capital game as much. And if it works for you, then you may already have VCs throwing, like, hey, do you want to chat? If you figure it out and you kind of get off to the races. So I guess, give us a little bit more context on Whippy and kind of...

what stage you guys are at and kind of how you've kind of structured your team and, you know, what would be, you know, well, I'll ask some more questions later. I don't want to stack questions on you.

David Daneshgar: No, no, it's all good. So I can get more into illumination, but when I left, you know, it's somewhere around 100 people. My actual title there was more of a CRO. Here is a CEO. I didn't even know what a CRO is. I probably still don't. But what mainly I was responsible for is revenue, like getting it and keeping it and scaling it. So

And I like the, you know, I always hear these things now about are you sales led, product led, and I think they kind of intersect, but I was someone who enjoyed the prospecting or hunting. So with Whippy, I mean, I think I alluded to it a little bit earlier, but you know, I would almost say that we acted as a tech consultant or something, so what happened is there was like a personal injury lawyer and like, hey, what's your problem?

And basically all of these could be solved in text or email. But like, oh, I get these leads that come on Facebook and they fill out a form for an ad and my team takes too long to get to them and qualify them. Cool. Oh, I have a bunch of clients and I wanna know if they're gonna leave me for another attorney. Okay, cool, we could send out this messaging via a mass message. Oh, if they ever say the word Uber, I wanna automatically assign it to my key salesperson because that's a huge case. And so you need some automation or AI for question and answers. It's very functional.

then a staffing company started using us and they need to send jobs to thousands. And one of the things that we started building was the backend software on message. I would say delivery and throughput. A lot of the SMS providers, like we would look up the phone care of the recipient and there's something called a brand score, which is like, hey, you're failing AT&T. We're only gonna give you this much amount of messages. And we could basically throttle it based on these kind of more complex formulas so that they could get more deliverability when they were sending out jobs and stuff like that. So there was some of that as well.

But it really kind of started as an SMS platform. And then we started realizing like, oh, they need to automate these workflows. And so they use Zapier and certain stuff. So hey, if we could build automations inside ours. So hey, if you ask someone, how was your experience one through five on your job yesterday? And they say a five, automatically send them a Google review link. If they don't open the Google review link and we detect that, automatically send it again. And since they gave us a good score, three and 10 days later, ask them for a referral. That's what those companies were having people do.

David Daneshgar: and we realized, hey, if we do a lot of that automatically and then surface up things to people, wow, would that be more efficient? So I kind of call it like functional AI. And so those different use cases you're saying, those are us just getting paired up with someone where someone tells someone or we go out there and send out cold emails and someone's like, like I'm a pharmaceutical, I'm a compound pharmacy. And what I need, my problem is to increase my refills and reminders and stuff like that. And my serum doesn't do that. And that's where we'll bring in like a product expert in Whippy.

who does two things, they're almost like an entrepreneur, CEO in residence at Wippy, they'll look at like what are the needs and what's the market size. Like, oh, and they'll make a pitch internally if we build one, two, and three, we could get this many pharmacies that use this many CRMs. What ends up happening, I will almost call it notion-like, is we just create blocks. Like there's automations, there's campaigns, there's these different things, but then people can actually kind of customize it themselves where partnerships has become a big thing.

like even marketing agencies that want to use our software or API to enhance their own, let's say, software stack because they don't want to build a lot of this. So WIPI is a communication platform focused on SMS, adding email down the road voice that utilizes a lot of automation and AI. And it's being used to fill a lot of the gaps that maybe their CRM or their current workflows aren't doing. And again, just to double down on how important that is, we would go out to people and figure out how much will they pay.

Will they forward us that money if we build this? Do you know what I mean? So we almost acted like a tech agency in the beginning, just because we were bootstrapped, which actually means you can't take fluff. You can't take someone who's like, oh, I will pay you this, which is what you hear a lot of startups doing and what investors may say. Like in the bootstrap world versus the other world, like money is the lifeblood of it. So you have to actually do your best to pitch something that they'll pay for in advance, right? And then you just have to justify yourself.

Are there thousands of others people that would utilize that?

Jason Kirby: Yeah, you say something so magical there like I was just talking to a founder and they were so set on like giving away Their service are free to get a logo, you know, like a look, you know get a brand that says they're gonna use their service you know when they start charging and you know, they're so you try to basically use VC money to subsidize customer acquisition and That's just doesn't flow anymore. You know, VCs kind of see through that and you know recognize like if you can't convince them to pay you

then you probably shouldn't exist. And so I think it's smart of you to just gonna go in there and it's like, there's no BS, you're going after customers that are actually paying you for the value that you're delivering. And it's not like trying to manufacture or fabricate a story that will convince an investor to give you money to then build a product that maybe the customer will use.

You're kind of going straight in for that customer value proposition right away. And listening to your customers. Putting yourself out there and kind of seeing what comes in. And albeit it can sometimes, it depends on the business, your tech seems pretty...

scalable across different industries. But I think that's something that founders really need to analyze and think about of how are they going to marketing, getting those first customers, and do they even need to raise money if they get to. If you're charging the right amount and you're maximizing the value. Because also, I went to your website and.

I've seen a lot of kind of chat solutions and marketing solutions and they usually start off like pretty inexpensive and it's per user model. And I think you guys are kind of like in the mid range and a couple hundred bucks a month. And it's probably because you're replacing a human in some cases or augmenting a human.

David Daneshgar: Yeah, I would say it's pretty wide. I mean, you don't see it there. There are people that pay us 10 or 20 grand a month. So, but there are people that pay us, you know, nine, nine a month. It is, it is, and that's another thing I would just tell you. We focus with the potential to make this more enterprise ready. So not just doing things like HIPAA and SOC2 and those types of things, but how do you support multiple users and multiple locations and multiple products that we can replace? How do you build?

some custom things for larger clients that can open the door for others, whether it's like an integration or adjustment to the product. But no, I think I would say that like, you know, on the SMB side, like if you think of some of the flower shops I used to work with, they'll use it for something and be at the lower price. But then we'll get to a large firm that needs it for multiple locations and like to replace certain workflows, as you said.

that people are manually doing. And you want to build something where, and that's a big thing. Like I want to continue to build where you can get 100K, one million, I mean, whatever you can go ARR contracts. But yeah, I mean, that's been huge because we went to market, I would say last year, so it was 2022. And yeah, it's helped a lot. Like for us, we have, I mean, you can do the math, but we have, we're a profitable company, we have 12 full-time people.

David Daneshgar: Um, uh, we have a bunch of, of contractors and we maintain to be profitable. But what I will tell you is like, we would go and like, if it was like a, if it was like a hundred K contractor, a 50 care, 20 K contract, the first thing me and my partner would say is like, Oh, that will enable us to get this type of candidate. So it was revenue that would get us to like, it's like, like blackjack double down on, on the company, which is really good because when you talk about

directions. For Blue Nation, if you raise a certain amount of whether it's debt-based, revenue-based financing or raise capital, you have people on your cap table that have certain rights and can kind of get you to the direction. They also need to return something to their LPs.

David Daneshgar: we can just keep doubling down and make our own version of a good story of like a Zapier or something where people are able to kind of like their only money, their rate is on secondaries. If you decide to be like a five, 10 million error company, right? And like that's good cashflow for you. That's still a solid world if you want to and a nice exit. But I think you just kind of leave those options open. I don't want to sit here and profess like I know exactly where it's going. As you said, that was a story we had to pitch to investors. I think right now we're enjoying the journey.

like really jiving well with our customers. We just got back from a trip from Dallas where we did take one of the old playbooks I had at Blue Nation and throw an event in a city, bring our customers in there, invite new customers, right? Like what better cool call is there to be like, hey, we're having an event at a pizza place and your competitors are coming. Can you come? Great, you're gonna be interested. Can you not come? Well, this is a good reason to get on the demo. So a lot of that, we still are maintaining some of that localized.

sales strategies and B2B strategies. But yeah, I mean, that's kind of where we're at now with Whippy.

Jason Kirby: So yeah, and I think really, you know, I've talked to a lot of, you know, bootstrap founders that, you know, get to millions of dollars in revenue. And just, just by recognizing how to connect and better sell their customers and really putting all their effort on that, as opposed to raising capital. And like, yeah. And here I am, like I specialize in helping founders raise venture capital, but like, you know, trust me if like, if

You don't need it, don't get it. You know, it's like one of the things I try to encourage founders to recognize is if you don't need venture capital, find a way to not need venture capital and ironically the venture capital will come to you. You know, I could very much see VCs reaching out to you and being like, oh, you know, would you be interested in having a chat, you know, coffee, like as you kind of get with me.

David Daneshgar: Yeah, yeah, for sure. So I think one of your questions that you messaged me before, I don't remember which one, but advice, or like how to raise capital, what I learned, it really is that question where it's like, if you ask someone for advice, they give you capital, if you ask them for capital, they give you advice. So I think that is actually a really true saying. And I think it's almost like, I mean, anything in dating, right? If you're too aggressive, everybody will be like, oh.

And if you're not and you're offending someone, someone's like, why aren't they asking me out? Are they not interested? So I think that same psychology, I mean, probably 10 exit for the venture crowd. And I think you'll probably get like what that formula looks like. But I think you're right. I mean, we ourselves, you know, just crossed where we just started. And then now about just crossing around 2 million in ARR. And for us, if you look back like a year, year and a half ago, the truth is I would have told you that's only possible if we raise money.

I think now, actually it's really interesting, when you do the math and you grow and you have that type of cash flow, it's almost like you raised a four or five million dollar Series A or a Seed. You have those logos, but I do think that by forcing yourself to kind of do that, you'll tell yourself if this is real or not. And one thing I can impart on the listeners here is the worst thing to do is be in a great place.

I mean, it's always good to find out like, is this viable or not as soon as possible because we only have one life to live. You know what I mean? And so like, if this isn't it, I know some people that start 10 companies that was the 11th or the fifth. But the thing to do is convince yourself that it is when it's not. And your best friends, it's hard for them to tell you, but your customers will. People that pay money, they pay for opinions with the green cash. So I think that is something that is, at some point, something that people don't wanna do because they may not wanna get the truth or they're not ready for it.

Jason Kirby: Yeah, no, I would completely agree. I have founders, myself included, like, pivoting, pivoting, pivoting, because not getting that.

that signal from customers of like, yes, and, you know, like, oh, yes, please take my money and more. And if you're not getting that signal, like clearly it's not hitting, you know, product market fit, but I still see founders like that are able to raise despite and, you know, trying to throw money at the problem when they haven't even found the real problem they're trying to solve. And, you know, one of my close friends out here in New York, he's, you know, I think he was on his ninth pivot with him and his co-founder.

like over the last two and a half years, like just nothing but pivoting, pivoting, pivoting. They only raised, I think, a quarter million for one of their ideas and maybe a half million or something like that. They kept at it in their most recent business in the AI space because they were like trend hopping and they just hit half a million a month in MRR in like six months. Just went from like zero

dollars in monetization to half a million a month. And you're just like, all right, that's product market fit. You're good to go. And they had term sheets flying at them before they even really went to market. And it just goes to show, like listening to customers and kind of listening and being willing to kind of pivot and kind of make the decisions that.

lead you to customer satisfaction and revenue as opposed to kind of giving things away for free and subsidizing it with outside capital. So I appreciate you bringing up that point. So one thing we didn't talk too much about that I think would be fun is to kind of tap in a little bit more in terms of what you leverage from your poker experience. I know it was years ago when you were active. I'm not sure if you're still playing in any capacity, but what are some of the lessons that you've leveraged or skills that you leveraged from your poker history to kind of build

capital and get to where you are.

David Daneshgar: Yeah, I mean, that's a good question. I mean, I think one thing about poker, I always tell you that I've learned in business. First of all, so poker is a little bit like a timed game. You can't sit there and think forever. And you have to have a lot of muscle memory. Like I've seen this before, but you have to decide quick. And I think that's kind of indicative of what I've seen founders be successful, which is like, and something that I'm always working on myself, which is like quick decision-making. I think one of the things...

I think for myself to some capacity as Bloom Nation grew, but also at much bigger companies, there becomes this level of, I don't want to say bureaucracy because that may be something, but like you get in meetings. I think what you're seeing now, people are letting go of a lot of what do you call it, middle managers, because there's meetings on meetings on meetings. I think there's so much to be said about something that just makes a decision. And then even if it fails, they move quick. That would be like poker versus a meeting. You can't go to a

and say, time out, and like, here's a meeting, and time out, guys, this is the meeting about the meeting about this hand, and like, I'm back in. You have to decide quick and live and die with it, and a lot of times you're wrong. But I think that's been helpful. My partner, Jack's done a fabulous job of that as well on the technical side of stuff. So I think that's one part. That's pretty helpful. I think another one that I'm currently working on as well, but it's like tilt, I think, to a certain capacity in poker, I don't know if you play poker yourself, Jason, do you?

Jason Kirby: Yeah, it's been a while, but I was pretty active back in 2006 as well. Nothing to the skill side of you, but I was playing online, playing with friends all the time.

David Daneshgar: Okay, good.

David Daneshgar: I mean, we see it in business, especially we're going to bootstraps and there's going to be a lot of volatility. And it's a good example of bootstrap because you're a bankroll. So poker players go under a lot of stress because they have a certain amount of bankroll and if they're out, they're out. They have to go back to getting a real job. So I think in that world, like if something knocks you off your feet in poker, the best players, when you think of the Phil Ivies of the world, they're like very even keeled, like they're somehow able to like get through them. And I've seen that with a lot of founders too, especially when you have other people on your team, because it's like, if you don't do that.

and they start to see you kind of shy away or lose confidence or believe me, there are mornings I wake up and I go, shit, what am I gonna do today? How am I gonna solve this? But I think that's something that like the founders may have to harness and you need to make sure you kind of lead by example. And so I think that ability to not get onto tilt, as we said in poker is something that's pretty viable from the poker world as well, as I mentioned. And yeah, I mean, I think if...

I mean, there's that whole cliche about reading people. There was an example even in Blue Nation that we raised an extra million dollars from just like making a read off someone and saying, hey, this is our last and final. I think here, whether it's negotiation or people, I do think there's a certain capacity to reading people, but I do think in the end, just like the execution and the variance, those are things that go really well with the founders.

Jason Kirby: Yeah, no, I think that's a valuable to look at. I think everyone's kind of looking for that. Like how do you read people and kind of read situations, but you're kind of quick decision making and kind of sticking with that decision, I think is something that as a founder, like you just can't like.

I think some of the worst founders I've run into, and I don't want to say worst, but like where they struggle the most is, you know, paralysis by analysis. And that's kind of what you're eliminating with your background and your experience is not kind of falling into that trap where you kind of just make the decision, make it quick and take it to another decision point where it's either worked or hasn't worked.

So I appreciate you sharing that insight. And from here, where do you see the future of Whippy? What's next for you in this journey? Do you ever foresee yourself ever considering venture capital? Are you going to stay the course, keep it bootstrapped?

David Daneshgar: I think stay the course. I mean, I think, I mean, this may motivate other founders, but the next round I want to raise is a secondary round. Like I don't want my, in our world, especially we've done something again, I maybe put myself in this situation as well, but like, as you want to have a family or you want to buy a house or stuff like that, like I'm not under the illusion of like, hey, let me raise and let me do this and in 10 years, like I actually have a lot of respect, I mean, obviously for that path, but also for like what our parents did or.

you know, people that had to like, you know, drive stuff now. So I think I'll stay down that path. I'm very excited about the product, my partner and the team. I think we've done a really good job of creating a core team that I would take against anyone anywhere. Like I think that's been culturally a big thing and they've all kind of subscribed to where we're going. We're adding other product suites. I mentioned email voice going into other industries. We just launched an API. So for a lot of these other.

systems that don't want to build off Twilio or just like there's a lot of dev resources to build some of that they can build off our platform as well. Um, I think, I think that, and just, I mean, honestly, just maintain a high level of profitability and. You know, I think focus on being a good company, but also I think focus on making the right decisions and making money. I mean.

I think as someone, and I'm sure some of the people on this podcast may listen to, and I think you mentioned it, there's a right time and there's, you know, if I had a company that needed a certain amount of capital unlock and I had proof points there, but I just couldn't get to it without that, like I don't know if I'm building hardware or software, I'm not sure. Like, those are things that are needed. Or if there's a real race with an incumbent and it's like a market grab, winner take all type thing. But I think for most businesses,

I think you said it well, if they start on this path, what's the worst that's gonna happen? They're gonna make the right decisions if anything investors are gonna come knocked on their door and they can have that decision. But here's the key thing, they can dictate the terms, not the investor. When we had conversations before and you're going out to people, the power's in their hands. And here, if we do this correctly and that door did ever open, it would be more that we were the ones that would be dictating those terms. Because if not, we were fine the way we were. You know what I mean?

Jason Kirby: Yeah. And I find that, uh, that's going to be, I think our, our probably next two years of venture, the companies that are getting funded are the ones that are more positioned like yourselves. And those are the ones that we're taking on as clients are the ones that, you know, are.

hitting a point of profitability or breakeven, have solid union economics, because the math equation changes now for venture. Of course, they want their 100x return, but they also want to see a clear path. So I give you a dollar, you turn that into a $10. They want to see the equation, and it's a much easier equation to build if you've already gone to market, have customers, have profitable business. But okay. I'm ready.

David Daneshgar: I think I'll throw a curve ball in here. I'll throw a curve ball for you guys. I think one path that actually doesn't get spoken a lot especially in early venture is strategic investment. Like there was a situation or there will be where they're like big companies using our platform or CRM companies using our platform. That to me could make sense, especially in like a secondary world where it's a win-win where you don't only get money, but you're locking up contracts. Do you know what I mean?

Jason Kirby: No, I think that is something that is often overlooked. And I think a lot of founders are scared because like, Oh, I'm going to give up my IP at the show them what I'm doing. And they kind of get hot caught up into not wanting to share and afraid of competition. Um, but in reality it's like, if it's that easy to steal, you know, you probably, you're probably not doing it. Right.

And that's something I always kind of, you know, rest on was like, you should be able to present to competitors or to, not competitors, like, uh, strategic and feel confident that you've built a product or a solution that is not easily replicable and that would be worth having. And that's the case, like you're again setting yourself up for success to, um, like in your situation, like lock down a strategic, both as an equity partner to potentially help you scale or bring you, you know, basically.

be a customer so they're bringing revenue and cash, which could be a win-win across the board, and as you described more of a secondary so it's cash in your pocket not necessarily into the business so it's a nice little win for you. But David it's been amazing having you on the show where can our listeners find you or follow you or you'll learn more about Whippy

David Daneshgar: I think if, I mean, they can go to LinkedIn, they can go to Instagram, they can go to Twitter, it's either under WIPI or WIPI AI, or you can check out our website, there's contact information there as well. I definitely think if there's someone listening and they think of a use case for them or a company or portfolio company that is, you can also, you can email us at info, info.

at whippy.com or info at hello whippy.com or find us on any of these social measures and happy to if there are other people that have questions about going down that path. Always I think this is a great conversation as you pointed when we start. It's just I do really like to myself listen to some of these podcasts that do kind of show other sides of the

the story and yeah, love to if anyone has any questions, they can feel free to reach out to me direct.

Jason Kirby: Awesome, appreciate that. We'll make sure to include those links in the show notes for people to learn more and to reach out. But any final parting words that you would like to share with the audience before we part ways?

David Daneshgar: No, I mean, I think that this was a super, basically two side in terms of the conversation. I think the main thing is there's not a, there's not a right way to do anything. I think based on the company, based on the tailwinds, based on the industry, I mean, I think they're both, I think that's the key thing. I would just keep an open mind for both and really try to figure out, but I would force yourself in the beginning, and especially for the next couple of years, it sounds like, to do this,

I feel like it's harder in the beginning. It's harder in the beginning, but once you do, a lot more doors or a lot more control becomes available to yourself as a founder.

Jason Kirby: No, I agree, especially that bootstrap versus VC world decision. Um, but David, it's been an absolute pleasure having you. Thank you so much for being on the podcast and we look forward to just sharing your story to our, to our audience.

David Daneshgar: Thank you.