How Whippy Doubled to a $4M Run Rate Bootstrapped After Leaving a VC-Backed Startup

Guys, David in two thousand and eight, nine, ten, eleven was the height of actually his poker career. One, the world's poker in 2008, which was great. Use that money. So I'm gonna go to business school, sharpen up here, then launched a company called BloomNation in 2012, stayed there until about 2020. They raised a bunch of money. There were three founders. They got really diluted. The three founders owned about, caught under 50% of the company when

he left and ultimately launched Whippy AI, which is now helping folks like doctors offices, right, do better marketing, also use the platform for operational experience. He's currently got about 600 customers paying an average $600 a month, but Clear Enterprise Motion built in area already has customers that are paying more than $100,000 per year. He's hoping to expand in that market and drive revenue growth this year in 2024 of over 75%. They're at about 4,000,000 run rate

today, from 2,000,000 a year ago and about a million before that. So good growth, all bootstrapped, which we love. Hey folks, if we haven't met yet, my name is Nathan Latka. I launched and sold my first software company back in 2015 and went on to write a book about it, which you guys made a Wall Street Journal bestseller purchasing over 30,000 copies. Thank you so much for that. After the book, I launched this show and one...

Went on to create founderpath.com. I raised a large fund to do non dilutive deals with b to b software founders. So far, we've invested in over 400 software founders totaling a $150,000,000. Here in 2024, we're doing three to four new deals per week. So if you're looking for capital and don't wanna give up equity, go sign up at founderpath.com for free to get your offer. Alright. Let's jump into the interview. Hey, folks. My guest today is

David Daneshgar. He's a former WSOP champ, cofounder of BloomNation, and today, cofounder of Whippy. David, you already takes the top?

Yeah. Yeah. Go for

Well, I did not know you played poker. What year did you play?

Yeah. I was a professional poker player between 2,005 and 2008. And then in 2006, I was ranked top five. In 2008, I won the World Series of Poker, so it was super fun. Couple of years.

How much is skill and how much is luck?

I I think it's, like, classic, like, everything else. The short term, it's a lot more skill dominated. It's hard to see the variance. But... Sorry. Short term is more skill based... Luck based. Sorry. Today's not a long day. But long term, yeah, skill based. Like, to see a poker player win millions over a long term over a certain long number of hands is definitely very skill based, and It was a fun fun time actually.

That's great. Alright. So let's get into Whippy. Maybe tell us what the product does, maybe through the eyes of a customer that uses you today.

Yeah. So it's being used... Basically, a lot of businesses are looking for AI and automation, and I call it functional. They're using, like, CRMs that are not the most savvy. So they have, basically, these databases, and they can't run automation. So we'll integrate and be able to run automation, text automations, voice automations, email automations, workflow automations, basically. But we started with text, recently added email, now adding voice, Voice AI. An example could be like a staffing

company where an applicant comes on Indeed and they need to qualify them and ask questions, but a person can get them right away. And before they apply to a 100 other staffing companies, the text, email, voice will come in to collect all that information and add it to their database. So that would be a good example of how how Whippy works.

And so are you are you working specifically with, like, see Bodyprof Chiropractic. Are these physical... These are physical office dentists, things like that?

Yeah. Most of them, at least in the early end, are... You would think of it as, lawyers, dentists, pharmacies, insurance companies. You're correct. Like, the old old school world meets new school technology.

Mhmm. Mhmm. And and what got you into this? I mean, you, in between poker hands, run a legal practice or a dentist shop or something?

No. No. But I think the one experience I had is after poker and before this, we started a company. This one we bootstrapped, but the last one we raised about 20,000,000 from Andreessen, Spark, Ronnie Conway, a bunch of people, and it was helping local florists. So I think there, when I looked at how they communicate and how they can be more efficient, retention, stuff like that, I noticed just things were really manual. And we... Our first foray was in text messaging because just that's where you get the leads quicker. That's where you get action quicker. That was, like, the lowest hanging fruit.

Mhmm. Interesting. And I guess close out the Bloomation story before we dive deeper into Whippy. So how much did you raise there, and what what was the end story there? What happened?

Yeah. So we raised about 20,000,000. I actually departed. I was a cofounder and CRO, and I think just decided after six or seven years wanted to start something else. So I left. Both my cofounders are there. I think they raised around after I left. So, yeah, it's still there. It's still intact. I believe it's about a 100 people, employees when I last checked. But I think the one thing for me is I wanted to build something

a little bit differently, bootstrapped. There was two things I wanted to do, not raise money so I could decide my own fate and how I wanted to do stuff. And secondly, the addressable market size. I think we were really specialized in the florists, and I think BloomNation, as I was leaving or after, was trying to get in other industries, but that was difficult. I think here we started with something super broad, like communication, and then we

narrowly define the use case, which was challenging in itself to start, but I think allows it to scale scale user without like hitting hitting roofs or hitting a small small industry. But, yeah, the company is still there and excited to see them continue to grow.

I'm not asking you to throw the VC investors under the bus, but I do think that founders, you know, VC money is I think the best marketed money in the world. And for every one that raises, there's a thousand that are profitable, happily bootstrapping at 5,000,000 run rate. You have the foresight or just the site in general to basically have both. You've seen both worlds. What advice would you give to someone today looking at raising versus not?

I think the best thing I've ever heard someone say is optionality. So it's like if you don't raise, you have the option. You can do it on your terms. You don't look needy. So I compare it a lot to going to a bar and talk to... You don't need to meet anyone. And, generally, things come to you.

Like, right now, I think I've had three or four emails in the last day just on family offices. I've had... Like, just looking. And when you don't need it, they want you more. I think that's that's part of it. I think this... The second thing is just, I think, you need to make poor decisions. I don't wanna throw them under the bus, as you said. But when someone starts a company, if someone gives them $5,000,000, I

think they make poor decisions. If the only way to hire people is through customers paying you on contracts, means that you have to actually build something that people want. You have to get a credit card, and they have to pay you. So it's much more difficult to start. But I think once you get to, like, the... As you said, like, the 3 to 5,000,000 AR and you scale, you build product better. You make better decisions. You're

much more comfortable. Like, even on sales and acquisition, you look at payback and you look at things that matter. You look at your p and l a lot. It's it's... You you actually act like someone like your dad, how he ran a business. Right? But actually with new age technology. And if you can do the both and scale and get past that chasm, I think it's just lights off. I mean, you can do whatever you want.

Well, yeah, forgive me for putting on the spot and doing this analysis live. I'm gonna make some sweeping generalizations generalizations here so the audience can learn with us. I mean, three co founders, right? Let's just, you know, twenty ten you found it. Let's assume just for the sake of argument, split up maybe 33 each, which maybe you didn't, but let's say you did. And then you do the seed series a, maybe a pre seed. I mean, pre seed is 20% dilution, Series a is

I can tell you. Yeah. I can tell you about it. Tell me the details.

What happens is you freaking burn out, and that's what happened to you. Six years.

Yeah. Yeah.

Wanna go start something new.

Yeah. The the three of us when I left, I mean, cumulatively owned less than half.

Mhmm.

And I think what it was is... I can just tell you kind of the path without getting too much details. Like, the first thing we did is as we're raising money, we went to Mucker Labs, which is like... I don't know if you're familiar with Mucker, but it's similar to, yeah. It... It's a local incubator that's done well, actually. Like, they had service Titan Honey, etcetera, come out of there. So they've done quite well, the owners

there. But, like, there was a small percentage we gave for base capital, you know, just just the incubator world. Then we raised raised a c seed, series a, and I I I don't know if I would call it a plus or b as well. So you're right. Like, at the end of the day, just the process is daunting. Like, at that point, the CEO has spent a crazy amount of time. I think just the hardest part

is actually decision making. Like if you wanna change your path, like if you don't grow, you don't get money. Like I hate to say it, but it's like someone who has the carrot, so to speak. And I I just... I think at this point we can scale how we want to and we don't have to worry about like, oh, if we don't have certain growth metrics or stuff like that. Oh no, we can't get capital. If

we don't have capital, we can't sustain our burn rate. So I think, but that was our path. It was like you said, getting chopped, chopped, chopped. I think there are paths for that. I think what I'm just learning about is to give advice to your audience is we don't realize that we can do it without it when our backs are against the wall. Like, you're if you're creating, like, hardcore, like, AI hardware or, I don't know,

certain stuff, you you may need it. But I think for the majority of software companies, if they ask a little frugal and a little bit of difficulty in the beginning, they're better off long term. And then there's things that I learned even now that I'm like shooting myself for. Like by bootstrapping the company, I'm sure you know about like things like the eighty three election or where you can get a certain amount back. Like, by bootstrapping

it, or you can get 10 x what is that that price when you do go to to, like, a c corp. So there are things I'm learning that are other advantages for being a bootstrap company. I think just most importantly, you don't have to waste that time. And they come to you. So that's kind of been my realization. It's harder to start. Mhmm. Mhmm.

How much of those initial, the Mucker Labs, then the seeds, how much of that was you guys, I mean, you maybe look back and say, know, it would have taken us longer, but we could have done it at Bootstrap. But a lot of, in my opinion, raising money, the reason that especially first time founders do it is it's actually just, it makes them feel better. It makes them feel like they're doing the right thing. They can convince people to give them money, then they sometimes stick in a bad idea for too much time.

Yeah. So I think the main reason we did it, the cardinal sin there, is none of the three founders were technical, which by the way, like 10 ago when I came out of the University of Chicago and we started out of there and, like, Grubhub or Etsy were just starting and you're building a marketplace business, there weren't as many no code and API tools as there are now. So it's harder to start. So you had agencies.

You had... So I think there was maybe some reason for that. But I think if we were starting that now, there's probably no reason with all the tools. Also, my co founder now at this company was someone that worked at my last company and is highly technical. So the skills are completely different. So I think that was part of the reason why we we raised the capital. And I think you're right. Like, the last thing... And

I can see you smiling. But the last thing is I think it was just more like that's what we were told or that's what we saw was sexy. And I think now... Again, I don't wanna throw them under the bus because there are definite reasons why. But I think there are better reasons to try to figure that out with contracts, with p and l, like doing it that way. Because I think when you finally unlock something

real and you really need to scale on capitals at your disposal, you're giving less dilution. Everything is really clear in terms of how you're gonna scale that money really is the necessary fuel, and it might not be at that point either.

Yeah. I mean, all disclosure. I mean, you're not buying a 100 wind turbines you have to go install to start helping florists run their companies better. So it's not like it's capital intensive. I don't think so unless I'm gonna know about capital intensive at the start. But look, lessons learned makes a lot of sense. I guess, what year did you leave? Was it 2016?

No. No. No. I was... So my kind of path... I'll just give you my path in a nutshell. It was, like, 2008, I won the World Series of Poker. Two thousand ten to twelve, I went to the University of Chicago for my MBA, and then we started it in 2013. I left in right right during COVID. So I'd been there, by the way. The company's been there. Company's actually been there for now for, like, ten years. So...

But I left in two thousand twenty two twenty nineteen, twenty twenty, and started this kind of in the midst of COVID with some again. And when we started, it wasn't exactly this idea. Myself and my partner were testing different ideas, but I think this really took hold at the end of twenty twenty, twenty twenty one.

Mhmm. Mhmm. That that makes a lot of sense. Okay. So going back into HelloWhippy today, describe to me how you guys charge. Right? So what's the average customer pay you per month or per year?

Yeah. Yeah. Sure. So even though the... My email is that the company is now gone gone to Whippy. So it's Whippy. The domain is whippy.ai. I would say right now we're moving more upmarket. So average MRR for a customer probably is around $600 a month. So $7.07... I know between five and ten k hours. I'd call that SMB. But we are starting to have customers that are are are north of 6 figures ARR. So basically moving up more enterprise market. What's the

way we do land on deal? So some of do have customers paying more than a 100,000 per year because you've got them paying for what API cost. What's the utility base you're saying you sell?

Not API cost, but what happens is when... So the SMB, it's like, why should you use our platform over another texting or automation platform? For them, it's developer cost. So, like, if they were to build off Twilio, they would have to build a communication plan... Twilio build certain features, certain stats, and, like, then it becomes, like, can your... And the developers, even, you know, a team of 10 and a big company couldn't really build this and

get this off. So if they have a specific pain point, that's where I think our our our API comes in. And then we also have... Happen to be integrated to all the different, what's called aggregators, so, like, we can increase deliverability to a certain degree. So when you put those two together and you're a large company, it's just not worth... It's better to buy than build, I would say.

That makes sense. And you started onboarding customers in what year? When did you... How'd you get your first customer?

Yeah. So the actual real first customers, and I don't know if they have the best use case for people, but it was just my old customers. So floors were some of the first. You look at retention. Retention wasn't great, and I think the reason we realized is they were using it just for marketing. We saw high retention of people that use this for operations. Like, if the platform came down, we'd get messages within one minute. Like,

I can't communicate with customers. So I think that started to happen about two two years ago, two and a half years ago, and the hardest part was just finding the use case. It was depressing. Like, I I come from a sales background, so making cold calls, walking into people. But eventually, I think it was a couple of cold emails and sequences, getting databases, sending out sequences, looking at open rates, getting on demos, and then honestly just customizing the software a little bit for that use case. That that helped a lot. And then when you do that

But how do you even know which data... You had to do something to say, wanna go get a database of lawyers or a database of whatever happened.

I I looked at competitors. Got it. So it it rather than... The the simple thing is rather than go to actual industries, I went to use case. I went to someone who uses this software. I pulled that from, like, built with or just different databases, put them into... I think we use Apollo now, but I think then it was, like, Outreach. So Apollo sequences look at open rates, adjust subject lines to see, you know, like, the the hustle hustle type stuff.

Well, me what you've searched in BuildWit to get a result of all the sites that that JavaScript was in... It was installed on. Just give me the name. Come on.

No. I think the the thing is for anyone here, like, BuildWit's a great tool. And and other tools like Apollo, like, there's obviously... There's also right now, like, a lot of intent based tools. Right? Like, you could look up intent for SMS communication. But for a... For for... I mean, I just go find a competitor's name. I'd find a competitor's Well, I I think... Yeah. So I'll give you one example. Because I think two years ago,

example would be Zipwhip. Zipwhip was bought by Twilio and went out of business. So there was a feast for all the customers. And, like, we just started this. So I was able to pull a list from Zipwhip and then feed that to someone on Upwork to, like, get deeper into the data. Because I didn't have Apollo back then. And then just, like, blast them. And then they Upwork.

You gave that list to Upwork to get emails attached to all the customers.

Yeah. I think now, obviously, Apollo and stuff, but I I had them do the hardcore. I went on Upwork and had them even fill out their web forms. Right?

Oh, got it. Got it. I see.

I see. Anything. Anything. No. No. Everything. I would text their their landline number, go on their web forms, put them in email sequences, and the Upwork person would use their own tactics, I would say. But now I think they were probably

Top title were you targeting? Was it, like, the CRO?

Well, at the point in time, because they were smaller, remember I started started with, like, five k, it wasn't difficult. Like, if you're going after a lawyer or whatever. If you're going after a staffing person, it was operations. If you're going after a lawyer, you're managing partner. So so I I'd kind of... Yeah. I mean, but those... Most of those companies weren't... They were, like, 10 to 50.

10 to 50 employees?

In the beginning. Yeah.

Yeah. Yep. That makes sense. Okay. And then fast forward today, how many customers are you working with?

I think we're getting close to a thousand. So probably right now, neighborhood of 600 to 700. So you can do the math on the ARR, but somewhere between three to four. About two x what it was a year ago.

That's where you're on to 600 customers at $600 a month is what? Seven point... What does that put you at? 3.6?

Yeah, somewhere between three and four right now would be ours as well.

Bootstrapped, right? I mean, is... You're in such more of a powerful position today than you were two years in at BloomNation.

I think they're both different experiences because I think it's... I've I've gone and spoke on on both of them. Probably was a better place for me to learn there on someone else's dime, to be honest with you. So that was also not a bad ex, you know, time as well. Yeah. I mean, you have to do the math, but I think you make a good point. Like, if you if you were to do a venture backed

company and you raise and you have, you know, multiple founders and multiple... Like, your cap table is this big. Right? Yeah. You're like, at the end when these companies exit, you you don't realize, but I think the math thing is really a good one. It's like... They exit, like, five or 10% of... Let's even say, like, a $300,000,000 exit. Like, that's not actually huge. Whereas if you're getting a $6,070,000,000 dollar exit, which seems like that's much more attainable, a 100 with private equity and all these buyers, and you have 50%, that's a lot more.

You're a poker player. Would you agree with the statement that if you want to, in the least risk way possible, build $5,000,000 of personal net worth, you should bootstrap?

I think so. Yeah. I mean, I have my own net wealth calculator that I put now ever since I started this. Like, I put my stocks, I put this just so I understand. Think so... And I think

You want... You were pretty wealthy early. I mean, I think in o eight, that price was 625 k. And in, I think, 2011, what did you earn? Like, 2,400,000 on poker back... How old were you then? Twenty eleven?

Yeah. So I think I was... Basically, when I was at the height of poker, I was in my twenties, and I and I did have a 7 figure bank account from poker. So that was really helpful.

I mean, as long as you say... As long as you don't go, you know, spend it on the yachts and all that crazy stuff, you think it's great.

Yeah. But I think to answer your question, like, I think the answer is yes. I think the harder part is you shouldn't fool yourself. So I think the hardest part... That's why the bootstrap idea I like, because it's the truth quick. Right? It's truth serum. The mistake I think most people make, and I was telling this to someone yesterday, is it's like how do you price and find product market fit? If you go to someone and

you ask, hey. Would you use this? 99% of them are not gonna offend you. They're gonna say yes. I mean, who's not gonna tell you that at that dinner if they're your friends or something? But then if you go to someone, you're like, okay, I built this at the end of the call. Okay. Cool. Like, here's the Stripe link. It's 6,000. Do you wanna put in your credit card? Like, the truth really hurts or or you see that. And so I think with the bootstrap thing, the other thing is you just don't have a lot of time to waste. You have to get to the truth quick because your cash flow, your cash statement is the ultimate sayer of if you exist or not.

Nailed it. Talk to me as we wrap up here quickly about growth. You're at about 4,000,000 run rate today. Where were... Sorry, revenue today. Where were you about a year ago?

It was about half. So we we we doubled in the last twelve months. I think kind of on our our roadmap is probably, I would say, think about 70 to 75% this year and maybe 50 the next. But you know, within the next twenty four months, definitely, we wanna be at 10,000,000 in ARR bootstrapped as well.

So... And so I guess you broke the 1,000,000 run rate in 2022? Yeah. That makes sense. Real quick. How do you drive 75%? People say you can't bootstrap and also drive crazy good growth. What do you... How are you gonna drive 75% growth? I

think that's that's a good question because in December, I presented this company. I think it's just different channels. So here's my first question for most of the listening, but it's like, what what is the channel that people use? Let's just call for b two b sales. We started with outbound, which is different from a lot of people. Like, we started because of BloomNation. Again, a blessing of BloomNation, like cold calling, cold emailing, like, as true SDR,

and I was the AE. I think now we're starting to see inbound, but I think with our API, partnerships, trade shows, outside sales, like inbound, like those channels that most people rely on in the beginning are things that we haven't even tapped yet. So I think partnerships will be a big thing. Because as we go to different systems and we have mutual customers and they're missing stuff in their system. Right? If you're a accounting

CRM and you don't have this, this, and this, you can now use our API. You push people to us. There there could be like an affiliate rev share there. That and white labeling, stuff like that, I think, would be a big part of the growth over the next twenty four months.

Alright. Good stuff here. Let's wrap up, David, with the famous five. Number one, your favorite book?

My favorite book? I think the the... I mean, the... I'll just say the the Shoe Dog one. Nike is actually a solid book.

Number two, is there a CEO you're following or studying?

I think I'm always, for better or for worse, looking at what Elon says. I think it's pretty amazing what he's done.

Number three, what's your favorite online tool for building Whippy besides your own?

My favorite online tool.

Well, yes... For example, haven't done inbound. So yesterday, we just started looking at SEMrush, which was pretty insightful.

Yep. Yep. We... Shameless plug. We'll have Eugene, the president of SEMrush speaking at SaaS Open on March 28. You guys wanna meet him in person? Number four, David, how many hours of sleep do get every night?

When we started this, like, four to five, but I think now it's more six to seven.

Alright. And what's your situation? Married, single, kids?

Single, and my parents are worried.

That's amazing. They shouldn't be worried. That's great. And how old are you?

40.

40. Last question. Something you wish you knew back when you were 20 years old.

I think my biggest thing that I think about a lot is probably just spending more time learning about real estate. And I think recently, more and more recently, spending more and more time with my family.

With your family?

Parents, my brother. He just had a niece. I just had a niece. Sorry. He has a daughter. So just in general, with people that are more important to you, I would say.

Makes sense. Guys, David in two thousand eight, nine, ten, eleven was the height of actually his poker career. Won the world's poker in 2008, which was great. Used that money, said, okay. I'm gonna go to business school, sharpen up here, then launched called BloomNation in 2012, stayed there until about 2020. They raised a bunch of money. There were three founders. They got really diluted. The three founders owned about, caught under 50% of the company when

he left and ultimately launched Whippy AI, which is now helping folks like doctors offices, right, do better marketing, also use the platform for operational experience. He's currently got about 600 customers paying an average $600 a month, but Clear Enterprise Motion built in Erie already has customers that are paying more than a $100,000 per year. He's hoping to expand in that market and drive revenue growth this year in 2024 of over 75%. They're at about 4,000,000 run

rate today, up from 2,000,000 a year ago and about a million before that. So good growth, all bootstrapped, which we love. Check it out at whippy.ai. David, thanks for taking us to the top.

Awesome. Thanks for your time. Appreciate it.