David Daneshgar Founder of Whippy, Co-Founder of BloomNation, and Poker Champion

Interview on the Jason Hennessey Podcast 07-20-2022 - Episode 33
David Daneshgar

How Poker Champ David Daneshgar Flushes Risky Business

Ranked as the #2 poker player in the world in 2006, World Series of Poker champ turned entrepreneur, David Daneshgar, always knew he was destined for more.
Join us as Jason chats with the Berkeley grad about his love for soccer & the Lakers, being a math whiz, and a self-proclaimed nerd. Jason gets to the bottom of why David’s fascinated with statistics and probability, and how betting with friends in high school set him up for later in life.
David will share his journey to success starting with collecting baseball cards which later turned into playing cards at casinos around the globe, and eventually pushing him to gamble on a couple companies: BloomNation and Whippy.
Tune in to today’s engaging episode as Jason’s curiosity leads David to spill how he convinced Lakers’ owner, the late Jerry Buss, to write him a recommendation letter to business school, what it truly takes to be a great poker player, a better business owner, and even better person.
Please press the play button above and follow along below. Thanks for listening to The Jason Hennessey Podcast.

In this Episode

[01:30] Jason introduces World Series of Poker champion, David Daneshgar. David clarifies the pronunciation of his surname, shares a bit about his Persian heritage, his family, and how he became interested in betting as a kid.

[07:02] David discloses the career path he would’ve taken if he hadn’t found a passion for collecting baseball cards during high school. Jason recalls a friend who took a similar path from collecting cards to gambling.

[10:03] David talks about going to UC Berkeley and the lessons he learned while lecturing a “Probability and Statistics of Gaming” DeCal class. Jason and David also describe how “Black Friday” disrupted their participation in the online poker industry.

[19:09] David tells the story of his mom catching him sneaking in at 3 a.m. with $15,000 in his pocket, shortly after graduating from college. He also details how he was close to folding from poker altogether at a tournament in Barcelona.

[27:38] Jason is interested in how David qualified for the World Series of Poker. David traces his rise and fall in rankings from 2006 to 2007, respectively, and resurgence by winning the championship bracelet in 2008.

[31:58] David recounts the story of playing a one-on-one poker tournament with the late Jerry Buss, who helped him segue into business school at the University of Chicago.

[36:50] David outlines how he and his friends founded, funded, marketed, and blossomed BloomNation while attending school. Jason remembers pitching his wedding marketplace idea to the Zappos founders while BloomNation was sprouting.

[50:16] David divulges the reasons for terminating his tenure as CRO of BloomNation, now known as The Promenade Group, and his desire to build another company. Jason mentions how his desire for growth is transforming his role at Hennessey Digital.

[57:52] David takes us through the process of starting Whippy with Co-Founder Jack Kennedy during COVID lockdowns. He lays out its purpose utilizing automation and AI to help businesses become more efficient, and how the venture got its name.

[01:10:24] Jason learns about David’s trilingualism, how he and his mom use Whippy for fun, his most disappointing moment, what he’d like to contribute to the world, plus much more in our signature “Hennessey Heart-to-Heart” segment.

[01:19:17] Jason and David wrap today’s episode. David invites listeners to keep in touch with him and Whippy by messaging him at david@whippy.co.

Transcript

Jason Hennessey: David, “Dah-nesh-gar”? Did I say that right?

David Daneshgar: Close, close. “Da-neesh-gar,” but it’s close.

“Da-neesh-gar.” What descent is that?

Persian, I mean, really it’s Iranian, but in today’s day and age, we say Persian now.

Persian?

Yeah, but my parents are from Iran.

Okay. So, for those that are tuning in, David and I had met- We both live in LA, but it took us both going to Kentucky to meet.

We were out there for a mutual friend, Bob Simon‘s Bourbon Tour and there was some pretty fascinating people on this bus.

And after getting to know a little bit more about David, your story was just so interesting that I wanted to bring you onto the podcast.

So, thanks for coming up.

For sure.

So, you grew up in LA.

Yeah. So, I grew up in Westlake Village, about 30 miles north of LA between here in Santa Barbara.

Got it. Yup, they call that “the burbs of LA.”

Yeah, exactly.

For those that don’t know, he is a World Series of Poker Champion, which we’re going to get into, right?

And there’s not too many people that just walk around with that title.

And so, I do want to talk a little bit about that, but as a kid, were you a gambler? Where did this come from?

No, no.

So, my parents came from Iran after the revolution. My dad still doesn’t know how to play poker, but they were always very supportive, which was a big deal.

But in Westlake, especially 20-plus years ago, when I was in high school, it wasn’t necessarily the most happening place. So, a lot of us, after school, were interested in statistics and probability and fun. So, we’d bet a lot.

Statistics and probability. Fun. [laughs]

I think maybe a better way to explain that we’ll know now is we’d bet on sports. And we’d be like, “Hey, if you can do X, Y, and Z, I’ll give you three-times your money.”

So, just for the layman terms, not to glorify it, but we were always interested in making prop bets or always doing things that we thought were fun.

But in the end, when you tell someone, “If you give me $3, if you do it. If not, you give me $1,” you are in a sense guessing risk or probability.

Got it.

But it could be anything.

So, I think just after school, we were bored, is a better way to say that, after high school. And so, I just got into it, and one of those things was poker.

Poker. So, even going back beyond high school, what kid were you like maybe in grade school? Were you into sports? What were you into?

Definitely somewhat nerdy for sure.

Yeah, I mean, I was talkative. I could definitely talk before I could walk, which just helped me in the most recent ventures, but definitely in terms of classes, I hated English and I love math.

Okay, math.

So, I was very close to my family. I was lucky to have very supportive parents, my brother.

I was very close to my family. I was lucky to have very supportive parents, my brother.

I played soccer when I was growing up and in high school, and loved the Lakers, and kind of cliche, so to speak.

I would probably say the first sense of change was when I went to Berkeley. So, I got lucky to go to UC Berkeley, and that was definitely a different experience where I saw a different world.

So, before that, tell me a little bit about your mom and dad. What kind of parents were they?

Very close and still to this day, I’m very close with my parents and they’re very cool. I’ve been very fortunate.

Yesterday, I was calling my mom and we’ll get into Whippy’s text messaging, but we were pranking people on the software.

You and your mom? [laughs]

Yeah. So, I’m lucky that my mom specifically is probably still one of my best friends.

That’s awesome.

And my dad is super supportive, just a very different personality.

My mom is more of the business side. My dad is a gastroenterologist.

Okay.

So, a stomach doctor and very- more of a listener than a talker. So I’d say; that’s closer to my brother.

Sure.

And my mom is closer to me, more of an extrovert.

So, you have just one brother. That’s the two of you. Older brother?

Younger.

Younger brother.

Yeah, the four of us. And very fortunately, we went on vacations together, but we’re very close.

I have a family. I know a lot of my friends are like, “Well, I would do this differently,” but I don’t think anything my parents did-

I mean, I was very fortunate. That lottery ticket, in that sense, I got very lucky.

What’s your brother into?

My brother’s an attorney. He actually does some personal injury stuff, some corporate stuff, but he’s very lucky, and we are, that he recently had a daughter.

And so, it was the first, obviously, grandchild on both sides of the family, but it’s just been pretty awe-inspiring to me to see a baby and get to see the innocence and all of that.

So, it’s been an amazing experience and she just turned 6 months. Sienna is his daughter’s name.

Oh, that’s amazing. So, you get to spoil your niece, you said?

Yes. I hope to have a daughter or son myself, but it’s the best of all worlds, because I get to go during the happy times.

Once in a while, they’ll need me to change her and I’m happy to. So, I got to see that experience, but I get to see the best of it. Yeah.

So, when you were a kid, I think every kid was asked at one point, “What do you want to be when you grow up?”

I’m sure professional poker player when you’re 7 was not in the cards.

Yeah. So, at Westlake High, they actually had a course, I think, where you actually had a cadaver.

So, going through that, I was like, “Should I follow my dad’s footsteps as a doctor?” So, my dad is more the doctor, my mom is more the business side. I wasn’t like, “I’m going to be a firefighter. I’m going to be a movie star.” I thought I’d be a doctor.

But very quickly, I’m sure, I don’t know if some of the people relate to this, but I started getting into baseball cards a lot. Buying them, going to trade shows, selling them, loved to collect them.

And so, I think that and also, I was the same type of kid who lived near a golf course. I’d buy golf balls. I’d go to Costco, buy coffee, mark them up.

I quickly realized in high school, it wasn’t for me.

And so what was, was the entrepreneurial side and being your own boss. So, that’s how I grew up.

So, very quickly in high school when I was looking at the live cadavers and I was seeing people excited and I was just thinking about, “How can I flip my baseball cards to make more money?”

I think that already started to signify the direction I’d go.

That’s so fascinating.

So, a friend of mine, big sports better, goes by “Vegas Dave.” Dave Oancea is his name. He’s going to be a guest on the show here soon too.

He got his start in baseball cards too, right? And he was just doing things that an 11-year-old or 12-year-old would think of, where his dad would take him to where the hotel that the professional teams were playing, right?

Oh, wow.

And so, he’d sit down there waiting with his baseball cards, right?

And then he’d see like Larry Bird walk in, right? And, “Larry,” little young kid, “can you sign this baseball card?” And then from there, obviously, the value of the baseball card goes way back up, right?

And so, it’s so interesting that gambling, the connection, at such a high level today, starts just with an interest in baseball cards.

I will touch on one thing.

So, I think a little bit different than other people that went into professional poker, I never had the illusion that I’d do that forever. And even when I was interested, I was always more interested in the business.

So, I mean, we’ll get to that chapter soon, but I know some people who are doing it and from day one, I thought about it as an interesting challenge, but frankly, more like something that I knew-

Like people who play golf now, you could always do it when you’re retired and you can be a really good player, but I never minced the idea that it would be something that I would do forever.

Got it. Well, it’s a good skill to have, for sure, right, regardless of whatever you do with your life.

For sure.

So, you graduated high school. You said you got into Berkeley and went to Berkeley.

Were there other colleges that you applied for that you got into?

Yeah, but actually, I remember it. I mean, I was from LA. So, the two that I was- really was excited about was UCLA and Berkeley. I didn’t really apply to that many out-of-state schools.

And I think for myself, I was actually more interested in having grown up and my family being in Westwood, and so I ended up getting accepted to Berkeley and not to UCLA.

And I think, for that one day, I was bummed, but then I went to go visit Berkeley’s campus. And then as you’ll learn, it was a phenomenal experience for me. That really changed.

So, now, you’re a freshman in Berkeley. You have an interest in business from growing up and you were doing some poker and stuff in high school.

So, tell me a little bit more about your experience. You taught a class in Berkeley, right?

Yeah.

So, tell me a little bit more about that.

Okay, so, probably rewind until we get to that point, but when I got to Berkeley, I think the cool thing was that it wasn’t just the school, it was a city too. And so, got to meet a lot of interesting people, but the way people thought was different.

And so, one of the things that I caught onto was that there was something called a DeCal class and DeCals were students could teach classes if they could prove that there was educational experience. That’s probably questionable.

So, there was a class on Seinfeld, believe it or not.

A class on Seinfeld?

Yes, but these are student-run classes, so it’s pass, not pass. You know what I mean?

But then I took a class on “Blackjack Card Counting,” believe it or not. Again, this is Berkeley. So, it was very different, but I thought, “Oh, this is awesome. I’m pretty interested in poker. I would love to teach a class on poker.”

So, I went to go to apply and it got rejected. So, probably one of the things you’ll get with everyone is resilience.

So, my last year, I was like, “I’m getting more interested in poker. There was a casino out there and I seem to be doing okay.”

Believe it or not, this is the same quarter that Chris Moneymaker won the World Series of Poker in 2003. He hadn’t won it yet and it just happened to be that the class I was doing was that exact time where poker boomed.

And so, it hadn’t boomed yet.

And so, I was really interested and went back with a bag of bagels and I said, “I’m going to go find a math professor and show them the statistics behind it.”

And luckily, that last quarter before I left the last semester, they approved it.

So, my last semester, I got to teach- It was actually called, “Probability and Statistics of Gaming.” It wasn’t called poker, but yeah, it was there.

And the most important lesson I can tell you about that experience is that you learn quickly when you have to structure things. So, I had all these thoughts, but they weren’t structured. And starting next week, I had to teach a class.

You learn quickly when you have to structure things.

So, very quickly and at that point, it was just VHS. I had to order VHS videos. I had to put my own curriculum together. And by doing that, I actually learned how to structure my thoughts on poker. That helped a lot.

Fascinating.

Funny that it’s okay to have a card counting class, but not a statistics class, right?

So, my president of Hennessey Digital, our agency, went to MIT. Obviously, MIT has the very famous story.

Poker- I’m sorry, blackjack.

Blackjack. Yeah, that’s different, in blackjack. Yeah. I was actually ironically in the movie 21.

No way.

Yeah, I played a DJ. I ended up getting cut out.

So, after spending 8 hours on set and making $50 bucks, I’m thinking, like, “Hey, this is my claim to fame.”

Go to the movie theater, watch it, bring all my friends, and they’re like, “We can’t even see you.”

And so, anyway, that was a big let-down.

But that was pretty fascinating because I think they teach that class in MIT, but then they say that you can’t go and use it at casinos, right? It’s illegal.

Yeah. I mean, I don’t know all the rules, but I know one thing is- So, I mean, I don’t know how it’s illegal.

There’s some rule that says you have an unfair advantage on a casino. I mean, common thought would be like, “Well, you have an unfair advantage when I play every hand.”

Exactly.

So, there’s a lot about that, but I think one of the most interesting cases that you can read about was Phil Ivey recently- They withheld $20 million from hotels because he was playing, I think it was pai gow. It’s a little bit different.

It was basically on the edge of cards, their perforations. And he was with a lady who could memorize those.

Wow.

And they didn’t know because it was a high net wealth individual and he loves to gamble, but I think he’d won something like $20 or $30 million. And it’s in court now.

Is that unfair? It was the casino that put those cards out, not him.

Sure.

So, there’s a lot of stuff on what is considered an unfair advantage.

Interesting.

I thought it was cool and I got to know people when I took that class, but once I was the student, it was pretty quick. I said, “You know what? This is awesome. Maybe I mentioned poker, I can do the same next year.”

I can teach a class.

So, another quick story about poker for me. So, way early on in my career, probably dating back to probably around the same time with the Chris Moneymaker stuff, I was doing SEO for Ultimate Bet.

Ultimate Bet and Poker- I can’t remember the other one. There’s another one.

And so, my whole job was basically keeping us ranking number one for the keyword “online poker,” right?

And there’s some crazy strategies that I think we talked about, even when we were back in Kentucky, but that was so fascinating.

Yeah, Absolute Poker and Ultimate Bet, those were the two, and we had them ranking number one and number two.

And then Phil Ivey’s Poker Stars was the other one.

At the time, there was Phil Ivey’s Full Tilt Poker.

Full Tilt. Okay.

And there was PartyPoker and PokerStars.

PokerStars was the other one. Yeah.

And I remember seeing them and reverse-engineering all their SEO strategies back in the day, because it was such a big difference in profit to be ranking number one on Google for that term.

But then I remember very clearly, I was in Vegas and I woke up one morning, and my text messages were blowing up and every single website, the FBI had seized.

Do you remember that?

Yeah, it was called “Black Friday.”

“Black Friday.”

I think it was after I won the World Series of Poker and I’m thinking about the next thing.

But that totally changed poker because what happened during Black Friday is, you’d have to look this up, but I believe there was, believe it or not, terror bill at the time, something like that.

And someone in Congress or Senate snuck a clause in there that had to do with payments and processing, because it could go to someone that you don’t want to and poker fell under that.

So, it really changed poker, because at that point in time, if you can’t get money into accounts, like the phish, the bad players, they need a quick fix, right? And they can’t get it anymore.

So, it ended up eventually being pros against pros. And then, by the time that momentum ceased, it wasn’t able to catch back up.

So, that whole series where the sites went down really changed, I think, the landscape of poker.

That whole series where the sites went down really changed, I think, the landscape of poker.

Oh, wow. Yeah, no warning, nothing. It was just like, boom. It was shut down.

What do you do?

And that was a big account for me obviously. So, hit me financially at the time, but it hit so many other people. My problems were just so micro compared to everybody else, right?

So, what was one of the most rewarding parts about teaching that class and working with students?

So, going back to a kid, as I said, I wasn’t shy, but definitely, I hadn’t had a platform.

When I go to the future and we talk about companies and teams, I think educating people and finding digestible ways to do that is imperative for anyone. If you want to grow a company, even a customer, right now, as I onboard customers, you have to speak their language.

So, some of them, you may have to be technical. Some of them, you may have to be just like mano-a-mano. But I think I learned that everyone learns at different paces and you have to figure that out.

So, that was very rewarding.

And the other thing that was very rewarding as you’ll tell is that as I actually had to put this stuff and teach people, I was teaching myself.

And at that point in time, there weren’t a lot of people- As the class ended in May, it was that summer that Chris Moneymaker won the World Series.

So, when you have this rush of people, it was fortuitous that right at that same time, I’d already thought through strategies.

So, that ended up becoming very helpful for the next couple years.

And so, you weren’t a professional poker player at that time, were you? Because you’re still in college, right?

No, and it wasn’t after. After college, I graduated and I was like, “What should I do?” And so, I worked at Country Wine, which may have been one of the chips or dominoes in the financial crisis. But I wasn’t really fulfilled.

I was like, “Okay, this is cool,” but I was still thinking about poker.

And so, when I graduated and I was there, I was still going to the casino sometimes at night times. And I just realized one specific day, they had a tournament at Hollywood Park and I went to play it.

And I remember I was out until- I think I was living back home at this point, until 3 at the morning.

And I was like, “Oh, I was playing, I was playing, and I won.”

I mean, obviously, to size well out, but I think at that point, I won what I would’ve got paid 3 or 4 months. You know what I mean? I think I won $15,000 for this tournament.

Wow.

And so, I remember it was 3 in the morning and I just graduated.

So, I was back at home and I remember getting in, and my mom, the business side, goes, “What are you doing at 3 a.m.? What are you doing out?” You know what I mean? “You’re up to no good.”

And she could see I was a little nervous and I said, “Oh, I played a poker tournament.”

And she’s like, “What happened?”

So, I showed her the money and I was waiting to see what happens. And my mom to her credit is like, “So, can you do that again?”

Not the answer you probably were thinking she was going to give you.

Yeah. I think she, in her heart, already knew that it’s something that- I talked to her about what I did at Berkeley and stuff.

And so, when people think of poker, sometimes they confuse it with blackjack or roulette. But you’re playing against other people. You’re not playing against the casino.

That’s true.

And at that time versus now, it could be repeated quite often. People are not playing it correctly.

I see.

So, I think that started the next chapter.

So, I think this is a rhetorical question, because obviously, you taught a class on statistics, but having a math background definitely gives you a competitive advantage on the table.

Yeah. I wasn’t actually a math major. I liked math. I was an econ and business major, but I think there were a couple things that I used to tell people.

So, in poker, knowing the math’s helpful, it’s pretty important. So, that’s the first level.

The second level is psychology because you have to try to think a little bit about, “Why are people doing this?” And so, I think that’s even a more important level.

So, if 100 people can do math, I think 10 people can take it to the next level and understand the psychology behind game theory, or what are they trying to portray? It’s like a story.

And then I think only 1 out of a 100 have the fortitude to do anything about it.

So, it’s difficult because in that moment, your math’s lined up, you’re pretty sure everything’s telling you this person’s going a certain way, but do you have the courage to pull the trigger?

Your math’s lined up, you’re pretty sure everything’s telling you this person’s going a certain way, but do you have the courage to pull the trigger?

It can be a car. So, you have to somehow think of it as Monopoly money.

Yeah. It’s not real money.

Yeah, but I think if you can do all those, at least at my time- So this is 10 years ago. I mean, poker’s changed a lot since then.

I think that was a really good recipe for being successful.

Interesting.

And so, you see these professional poker players, right? There’s a strategy definitely happening within the whole table.

How often, just percentage of the time, did the professionals bluff?

I think that the actual correct answer is it’s depending on the situation.

So, I always like to put this in the real world, but it’s like, “How often does someone exaggerate that they’re going to be there on time?” Maybe just take it to a totally different level.

If they’re a nice person and you’re accepting of it, they’re probably going to do it more. If it was a strict teacher, they did it less. So, it really depends on your audience.

So, the better way to say this is if you’re at a poker table and most people are conservative, you’re going to bluff more. If you’re at a poker table, where everyone’s wild and crazy, you’re actually going to probably bluff less.

So, if you’re playing it correct, there’s no set formula. It’s a dynamic game like life.

Got to read your audience.

That’s true.

David’s revealing some of his personal strategies here on this podcast. I love it.

All right. So, you won your first tournament. All right. Mom gave you the blessing to move forward.

After my bar mitzvah, this was the next blessing.

So, what happens next? You’re hooked.

I mean, I was intrigued.

And so, after a couple more tournaments, I said, “You know what? I didn’t have that much money to my name.” I was just like, “I’m going to go find another job that’s not fulfilling. And in the meanwhile, I’m going to just give this a try to see what can happen.”

And so, what started like that definitely turned into a couple more tournaments where I just thought it couldn’t be chance.

And so, I remember specifically, that same year, to my brother, I was like, “What would be really cool is to go travel and play poker.”

And so, there was a tournament in Barcelona and I said, “Let’s go for it. Let’s go for that tournament.”

And I remember it was a bigger tournament. There was maybe $1,000 dollars, and at that point, the highest I played is $100 or $200 to $300.

And I remember I just kept losing and I kept losing. If you started with $1,000 in chips, I was down to $80. I was demoralized.

And so, in poker, a lot of times for the bigger tournaments, they have dinner breaks. So, I remember telling my brother, “Let’s just get out of Spain. This poker’s not for me. It was a good run, but I really wanted to try it in a bigger tournament.”

And I tried a couple and I was like, “Maybe I’m not that good.”

And I think that’s life. I know we’ll talk about failure and stuff, but I think adversity is a big thing that doesn’t get highlighted as much.

But at that tournament, I came back and I think probably luck more than anything, but things started to turn around and I ended up winning that tournament.

And I remember how much things changed. It’s like a ripple in a pond.

After you told your brother that, “Hey, I’m ready to get out,” you ended up winning it.

Very quickly. I was like, “Okay, we’ll just do this as a hobby.” I ended up winning it.

So, I won a larger sum amount of money at that point, that was very significant to me. We went out for dinner and my brother, Stevie, was there in Barcelona with me.

And I remember coming back and I was like, “Okay, I’m going to really give this a try.”

So, that was one time where I was literally one hand away from probably not being able to continue the path.

That was one time where I was literally one hand away from probably not being able to continue the path.

Yeah, giving up.

Sometimes it’s crazy. It is. Some of it is luck as well.

So, you won that tournament, came back home. Mom said, “Can you do it again?” You’re internationally now a star.

Yes, taking it out to the next level.

And so, you’re like, “Okay, great. I’m just going to pursue this here and see where it takes me.”

And how old are you at the time?

I mean, definitely early 20s. So, I think at this point, probably 22, 23.

But then once I did commit, it was like, “I’m going to do this full-time for a year,” because after Barcelona, I had a decent amount. I remember I came back and won something at Commerce, where, by the way, just to throw a shout out, that’s where I met one of Bob Simon’s best friend’s, Morrow.

So, Morrow, who we’d met on our trip to Kentucky, just showing how long I’ve known him, I was like 23 and Morrow in that thing made the final table.

And still, 17 years later, he’s never made another final table.

Oh, really?

Yeah. So, talk about fate, right?

So, he became one of my best friends. That’s how I actually got connected to personal injury, but yeah. I came back to Commerce and I won that tournament.

And then in 2006, I just had a great run. And at one point, I was ranked number two in the world in poker. And I think at the end of the year in 2006, I was number 5, and I won several tournaments and that was like a life changing year for me, for sure.

So, that’s 2006, you said?

Yeah.

And so, how do you even get to play in the World Series of Poker?

So, I hadn’t won the World Series yet.

2006, I probably played one or two of the tournaments in the World Series and had no luck. So, then I won a big tournament at the Bellagio in Las Vegas.

And then I won a tournament at the Bicycle Casino.

So, I just started going around and putting a bankroll together, meeting a lot of cool people along the way. And that’s when I was like, “Okay, I’m really going to give this a run.”

And that year is when I finished top five.

Top five. Okay. So, that’s 2008 now.

2006.

2006 still. Okay, great.

But when was the first year that you played in the World Series?

Probably that year.

2006?

Yeah.

Okay, and you didn’t end up at the final table that year?

No. And to clarify, the World Series of Poker has a series of different tournaments. So, there’s the main event, which is ginormous, and then there’s several events that led up to that.

So, I think at that year, I had played two of the preliminaries, and then I think that year, I tried the main event as well.

Got it.

But no Final Table.

No Final Table. 2007, had some luck as well?

So, I think this is a good place to talk about adversity, right?

So, 2007, I started playing a little bit poorly, because what ended up happening, as in life, is you have some luck and you don’t adjust and you think you’re invincible.

What ended up happening, as in life, is you have some luck and you don’t adjust and you think you’re invincible.

And so, I definitely had this series of months where I was actually losing, not winning, because I was trying to outplay everyone.

So, it’s like in basketball, someone gets on the court and just starts trying to dribble and not pass.

And so, it’s like fancy play syndrome maybe, which is like I know that you don’t have the best hand, so I’m just going to push all in, but you still call, and you should have folded. So, you are a bad player, but a really good player would know that you wouldn’t have folded anyway.

So, I think there was some fancy play syndrome, which got turned around. But definitely in that year, there were definitely some doubts again. Okay, was I just lucky again?

And so, I think in 2008, that’s when I decided to play the game-

Correctly.

Correctly, back to where I was.

But also, one good thing about 2007, which you have adversity, is I knew that if I do get back to where I want to get back to, poker for me was a great game for networking, great skill to have, but it wasn’t the sell all, be all.

And so, I had already told myself, “Should I go and do something great?”

I had already committed myself to checking that mark off the box and moving onto what I thought was even more interesting, which was business probably a year before it happened.

Okay. And that’s an interesting story too, which I want to come to here, because BloomNation, did that happen before you won the World Series?

Oh no, no. After.

So, that’s after. Okay. So, let’s continue down this journey here.

So, 2008, you have a good year. You’re probably top ranked in the world again, I’d imagine.

Yeah. I wasn’t as ranked as high as I was in 2006, but 2008 is when finally, I won one of the World Series of Poker tournaments.

My family flew out there. My mom flew out there, my brother.

And I think once I won that tournament, it was almost like, “Okay, I now did what I needed to do.”

Yeah. Was that the main event that you went?

No.

It was not the main event.

It was actually the one right before the main event.

Okay. Got it.

So, it was still pretty challenging. I think in my term there was 2,500 people.

Sure.

So, it’s crazy. You’re up against, like, a mini stadium.

Wow.

But that’s when I said, “Okay, I did it.”

And so, I knew that the following year, I was actually going to make a change and still play poker, but you rode that high and leveled off, right?

And it’s interesting just to think about that. A lot of people that have been good at poker, they have leaks, right? They go to play craps. They go to play their stuff. Never. I was ever interested in that, because I didn’t get the same rush that I would in poker like reading someone and analyzing someone.

So, I was fortunate enough to take that next step and not as a result of going south, but as a result of just growing as a person, I guess you could say.

So, it was in 2009, where I was like, “I’m going to figure out what’s next and to take one step back,” which is an interesting segue. In 2007, 2008, I met a lot of cool people in poker, but I happened to play a one-on-one tournament in that year.

And one of the highlights was I got paired up with Jerry Buss who’s the owner of the Lakers who passed away.

And it was a best of three, whoever won best of three. And at that point, he was the owner of the Lakers, and the Lakers were hot.

And you’re a fan your whole life, right?

Yeah, fan my whole life. And he knew me before, but we really got a chance to know each other so I totally slowed the game down.

[laughs]

So, this person next to me is waiting to play the winner and I decided to make the game versus Dr. Buss last 5 hours.

Yeah. [laughs] Because you can do that.

Yeah, I could do it. And I think the reason I mentioned that is after that, I was lucky enough to get invited to the games.

And so, a funny story is when I’m trying to figure out what’s next.

I had asked this gentleman named Ed who was his right hand, “Hey, I want to ask Dr. Buss a question. I want to talk about my future. Can I come have lunch and come to his house?”

And so, they invited me and there was a table. And Jerry Buss is there and I’m there and they’re serving us sandwiches.

And he said, “Well, what’s on your mind?”

And I said, “Look, I love poker. I had a great education, but I think-I’m trying to think of what’s next and I think maybe a path to being the general manager of the Lakers would be a good idea.”

Why not? Go for it, right?

Go for it. Go big or go home.

Okay. So, did he kick you out of his house?

No, no. He liked me in terms of poker too much. So, he was very quick to say that his family was going to probably be doing that, but he’s like, “Was there anything else I can do?”

Because he went to USC and he was big in business. He owned a lot of real estate.

I know there’s a show now actually about it that people are watching, but I was telling him about business school and he agreed to write my letter of recommendation.

Who else do you want to write that letter, right?

So, that segues to the next chapter.

But before BloomNation happened, I decided to go to business school, because what I’d heard from a lot of friends and it’s questionable if it’s worth it. So, I can talk about that later.

But when you come from poker, when you talk about Dr. Buss, or someone at our school was an NFL player, or someone actually went to space, whatever it is, if you want to do a dramatic change, they’ve always mentioned to me that business school and getting your MBA was a good segue.

If you want to do a dramatic change, they’ve always mentioned to me that business school and getting your MBA was a good segue.

And so, that’s when I applied to business school.

Okay. Got it. And so, where’d you go to business school?

Being the poker player I was, I was pretty efficient. I’d actually hired a business school consultant, which was someone who really help you prep, help you take some of the manual work out of the process.

So, I mean they would help me craft my story and really just most importantly, learn my interests and point me to which schools they thought could be the best and tell me to go talk to these professors who are pretty nifty business, but I decided just, if it was going to be worth it, to apply to the best schools.

So, I got waitlisted at Stanford. Stanford’s where I wanted to go, because I was interested in business, but I ended up getting accepted to the University of Chicago.

I was in San Francisco. I was in LA. I was like, “Chicago’s going to be cold,” but it was one of the best business schools. And so, I ended up going to Chicago Booth.

Okay. So, at school, you’re now learning about business at a more advanced level. You’ve never had a business yet up until this point besides your baseball card business back in the day, right?

Yeah. There were some small businesses I’d done in the poker world, but nothing large.

And again, it’s just crazy about adversity. You get back there and you just got from playing a poker game and you’re like, “I’m going to the next level.”

And wow, that first year did I have a crash, because you go from that high to having to learn accounting again, having to learn about stuff. And so, there was definitely a point in the first year when I was talking to people close to me.

So, Chicago’s known to be heavy in finance and consulting. And so, I was surrounded by those people and I’d go visit those companies, and I was getting recruited a lot, given my background for finance companies, but it was semi-depressing to be honest with you. You came from a world where it was your own.

And so, I did contemplate, “Should I drop out of business school?” in that first year, but what kept me going and what I realized is that there was a program like a business school competition.

And at that point in time, a lot of, now, big companies came out of that competition. One was GrubHub, where people order food and other stuff. And so, I stuck with it.

And once they found the entrepreneurial path and one of my best friends growing up who was in LA, he had actually come up with the idea of BloomNation and he was talking to myself and one of his other best friends about, “Hey, this can be a real idea.”

That summer between my first and second year in business school, where most people go volunteer at a bank and sell their soul, so to speak, I was walking around to flower shops to see if it was a viable idea.

And so, that’s when we committed to doing it.

And then that totally changed my direction in business school. You were going to a class that was marketing and you could bring your actual concept there.

And there was a class on how to raise money.

Same with poker, I always thought: If you’re conceptually learning something that you’re not actually executing or implementing, it’s boring. You can read poker books all you want, but if you don’t get on the table, I think you’re wasting your time.

I always thought: If you’re conceptually learning something that you’re not actually executing or implementing, it’s boring.

Same thing with business. Yeah.

Exactly. So, when I was going to business school and most of my friends were doing mock classes, we were talking about raising money. I was going to the professor and be like, “Well, this is my business. And actually, we had interest already. Here’s something about raising money.”

And it just changed how I looked at business school, because I had a real business that we were running through business school.

And so, you have that business school competition and you start with 100 companies, but they give you some money and you get to be in front of investors. And we were one of the winners. I think we were third or second place. We didn’t win first place, but it was enough to kickstart-

The business.

Yeah, the business. Yeah.

Got it. So, you had an MVP, I guess, if you will.

So, that’s a good question. So, normally, you have an MVP, but at this point in time- So, maybe I’ll touch on what BloomNation was.

Yeah, please.

My partner at the time, Farbod, his aunt was a local florist. And he’d come from an investment banking background.

And so, he thought that the way you order flowers is you either call a local florist but you don’t have all these local florists in one place or you have to go through Teleflora or 1-800-FLOWERS and you can’t see what you’re buying.

So, there’s a total misconnection there.

So, if you want to go to one place, like an Airbnb for flowers now or like an Etsy for flowers so you can order anywhere in the country, it didn’t exist.

Teleflora did, but the photos you saw, it was just a broker. You know what I mean?

And so, that started BloomNation as that marketplace for people to go and order from anywhere in the country.

Got it.

And I come from the wedding business myself. I was a DJ for so long, right? I speak at the Wedding MBA every year, right? So, I deal and interact with these florists.

So, you started with the technology first and then from there, you went and got your first florist. Well, I guess it might have been his aunt’s business first, right?

That’s a good question. I can always talk about how we do things differently now at the next venture, but I think we started alongside with florists. So, there’s good and bad in that, but it’s always good to be able to talk-

And that was my job, to go find these florists. And it was a crazy adventure. Back to the poker world, you had no fear in poker. I know there was several times that you have-

To get things done in the beginning, one of my biggest tips in this whole podcast is if you really want to start a big business, you have to do things that are not scalable.

If you really want to start a big business, you have to do things that are not scalable.

So, I went into that shop and the guy said, “No.” I went in again and he said, “Get out of here.” The third time, he said, “I’m calling the police.”

And now, he’s actually one of our best friends…

Is that right?

…and suggests people, but starting a business is not easy.

No.

You have to be pretty-

Tenacious.

Like poker, you can’t get on tilt maybe.

But we went around and we did that and built it alongside some florists, built this marketplace, but that didn’t end up becoming our biggest product.

But we realized we were helping the florists as, “Wow, they need a marketplace.” And this is more your world even, but, “Wow, they need a website. They need marketing tools. They need SEO. They need something that has delivery tracking.”

There was just a whole platform that I think we needed to build. And so, that became BloomNation.
Got it. And so, you started to develop this. It was completely bootstrapped at first.

That’s a good question. So, it was bootstrapped.

I think we were in a fortunate situation where they, my two partners, Gregg and Farbod, they came from banking. So, they had a little cash. And I just came from poker. So, we didn’t start it with an engineer.

So, we started by going to an outsource agency and that presented its own challenges. So, we had to put a lot of money in the beginning, a couple hundred grand together.

But once we started seeing that and we met some investors, we were fortunate enough to meet some really good investors, but we had to start it with hundreds of thousands of dollars.

Which, when I started my next venture right now, I tried it a very different way, which we’ll talk about probably later.

Yeah. So, one of the fascinating stories is how you were able to leverage your poker skills to raise some seed capital for this venture, but then what’s even more brilliant than that is how you then leverage that for publicity and PR.

Again, that was the stuff that I’m like, “I got to have David on my show.”

So, we had to put a couple hundred grand, but back up, we had to start with $30 grand to get the outsourced company to do our proof of concept.

So, we were thinking, “How are we going to do this?”

And I happened to be still in the poker mindset, even back from business school, and I hadn’t played for a while, but I saw Commerce had a tournament that day. It was $1,000 buy in. It was 100 players. First place was $30,000-something dollars.

And I was like, “This makes a lot of sense. Let’s just split this. And if we win, we’re in, so to speak.”

And so, one of my partners was a little conservative and I remembered he was joking. He’s like, “You know what? If they send us a limo,” because we got to work on the way. We’re working.

And so, I knew someone at Commerce and they agreed. So, I was like, “They’re sending a limo.”

So, we sat at a poker table and I started playing, and they were next to me doing the design for the website.

And so, that tournament, 100 down to 80, finally down to 5. Once it was five, they stopped working and they were crowding around.

And when it was down to two people, I remember this vividly, the last hand, we went all in. And I had two pairs and my competitor had one pair, but he didn’t realize it. So, he started celebrating with his crowd.

And I could see them, but they’re like we didn’t have the $30,000 bucks. It was their mentality. We fell short.

And I remember the quote that they took, but what was real is, I said, “Don’t worry boys. It’s flower time.” And so, the guy came back, my competitor, and he basically misread my hand.

And so, that was the first $30,000 and it just kept blossoming from there.

So, cool. And if you Google that story, there’s press all over the place about it, right, because you leveraged that.

Yeah. So, Gregg, at the time, he was more knowledgeable about SEO and we happened to have a publicist, because he was all like, “Backlinks are going to make a difference, high authority backlinks,” all that stuff. And so, the publicist ran with that.

And I remember we had a publicist and she’s like, “We’re going to go to New York.” And I remember my partner at the time, the CFO was like, “She can only go to New York if she gets you several desk-sides.”

So, she’s like, “David, I’ll get it.”

And so, it sounds like a lot, but she booked like 12 desk-sides on one trip. We went to Fox News. We were at People magazine, Time Magazine, Forbes.

And I was like, “Wow, okay. This story really resonates.”

Sure.

And so, it really did make a big difference in terms of getting that story out.

Yeah. And so, for people that are listening that don’t follow SEO, right? So, when you get publicity like that and they link back to bloomnation.com, you get the authority that passes over and that accelerates your Google rankings and your whole business.

So, that’s why I really personally admire that.

So, then from there, then you guys went on and I’m making a longer story short, you then raised real capital then after that, right?

Yes. So, I think, just for people that are viewing, so first $30K came from that. We got the first version of our software.

Obviously, it didn’t do the job, especially back then when there wasn’t as many different platforms, whether they want to call Shopify or all these different stuff. We used Magento.

So then, we put some money ourselves and then we came back. There’s a lot of cool stories.

Actually, I think it was Bill Gurley. He didn’t invest, but he was on Benchmark Capital, the same one that was on the board at Uber, the one where they had that issue, where he was fighting with the CEO.

He walked into our office and he’s like, “This is pretty awesome, but here are the changes I’d make.” And one of them was that you need to give them more tools. You need to put their picture at the front. You need to give them software.

And if you do that, which now we know, because everyone makes their own Shopify store, if you give them the tools to empower themselves, that would be a good business.

And so, we ended up doing that and seeing traction, and we raised a million and a half soon after. We got lucky, really good investors, like Andreeson Horowitz, Spark Capital, big names that I was shocked that were investing in a seed round.

I see.

Back while you were doing that, I had a wedding directory. I had multiple wedding directories.

One was called “Los Angeles Wedding Mall.” I had “Seattle Wedding Mall.” I had “Phoenix Wedding Mall,” right? I had all these directories, right?

And that had a sales team that was dialing for dollars and calling the same floors that you were calling at the time too. And so, I had this vision of building out a massive wedding directory.

And so, at the time, Zappos had just moved from San Francisco, I believe, to Vegas. And so, I’ve seen on the news and so I just randomly sent an email to Tony, right, the CEO of Zappos. Rest in peace.

And he actually responded back to me, right?

And so, like in life, you have to take action to get results, right? Heck, we could be talking right now and you could be the general manager of the Lakers, right?

You took the action, you took the shot, right?

Yeah. You have to.

And so, I just randomly emailed him and he then connected me with a guy named Fred Mossler, who then connected me with Alfred Lin.

And so, they’re like, “Hey, come on down. I’d love to meet with you,” right?

And so, here I am, some young 22-year-old kid with a vision. I got invited down and they gave me this whole VIP treatment. And I was brought into the office with fricking Tony, Fred, and Alfred.

He’s like at Sequoia Capital, right? And so, what are you here for?

And I’m like, “Well, I’ve got this vision, I’ve got this idea.” And so, I messed up because my whole vision was monetizing wedding vendors, right?

And so, my idea is if I can get a florist to pay us $99 bucks a month to advertise here and if I could get a DJ in this market and build out, I was this close away from getting Zappos to invest in the business.

But what they didn’t like is that I didn’t see the opportunity to actually monetize the brides. That wasn’t really my pitch. I was more in tune in trying to monetize all the vendors globally and creating this marketplace.

And so, they politely declined, but the fact that I was able to get there was pretty awesome.

I’m trying to think. Was the winner in that type of world Thumbtack?

Thumbtack was. The Knot was the big one. And then another one came. It was a company called Wedding Wire. They came and they were more of the technology focused company, and then Wedding Wire ended up acquiring The Knot.

So, they actually owned them now. Yeah. So, but anyway, that was my story.

So, then, back to BloomNation, now you raised a couple million dollars and then you just continue to grow.

Were you the CEO or what was your title?

I guess in the beginning, Head of Sales and Business Development, but my role ended up becoming the Chief Revenue Officer, so CRO.

Okay. Got it.

So, we had CEO, Farbod, who I mentioned, thought of the idea and he was more focused just on the product and I guess you’d call the vision of the product.

I was more responsible in terms of getting money, right?

So, whether it was, like, getting people to purchase the software, talking to partners and companies that could potentially integrate with us, probably one of my favorite things was building out a team.

And so, similar maybe to now, you had to go from, I think, 1 to a 100, and how do you build a sales force and how do you build it so everyone’s firing on all cylinders?

So, that was my focus.

Okay. Yeah. It comes down to because you’re going to make a lot of mistakes because you’ve never done it before, right?

Yeah.

And then you just learn from the mistakes and that’s how you grow.

And so, fast forward now, BloomNation, still a business. Do you still have equity in that company?

Yeah. No, it’s very successful. So, I think I actually happened to go to the office.

So, I left the company 2 years ago and I can talk about that too, but I was on the board in the beginning. Now, I guess you just call it a shareholder, maybe friendly advisor. But no, don’t have any real active role.

I still get hit up every day from people with coupon codes or florists, which was great about the relationship like, “I need help here.”

It’s like dating. I mean, I still have a really good relationship with my old partners. That’s my mentality. It’s how I’ve always been.

When you’re in it, you’re in it. When you’re in poker, you’re in poker.

But the second you decide now it’s time for the next, poker gives you that skill, right? Because you have to somehow detach yourself from a loss or a win. You can’t have a win and go crazy. You can’t have a loss and let it drown you.

You can’t have a win and go crazy. You can’t have a loss and let it drown you.

So, I think once you’re in it, you’re in it and you’re hooked. And the second you decide you’re not, it’s almost like you can just detach.

I see.

So, I ended up just becoming, and even currently, just rooting for them. I think they’re probably heading towards 200 people.

Wow.

So, I think 150 people. They rebranded.

So, the company’s actually now called The Promenade Group, because the biggest thing we were trying to tackle towards the end was that we were doing really well with the florist industry.

But once you start raising a lot of money, I think they raised probably north of $25 million, you have to bring your investors a return, a high growth return.

And so, I think they’re now like, “How do we bring the same software to supermarkets, liquor stores, pizza shops, stuff like that?”

Wow. Okay.

So, they’ve rebranded and BloomNation is just one part of that multifaceted SMB approach.

And so, when did you know it was time for you to transition out?

Yeah, so I think in that case, it wasn’t as easy just to leave, but there was definitely parts where I wasn’t- I guess to say this, but you weren’t being challenged. You weren’t giving it your all or you weren’t enjoying yourself as much.

And so, I’m a polarizing person in that sense.

And so, I think there was some adversity we faced actually in 2016, 2017, where the company literally almost went under. And so, I remember there was a point where we raised money and throwing parties.

I mean, definitely not like WeWork, but we had a party, actually probably a smart party, because Gregg always made us have to return more money at a party than we spent. So, it would be like vendor parties. You know what I mean?

And it was all exciting, but eventually, that just fire didn’t burn I guess.

And I think one of the reasons is as we grew and we raised more money and it was 100 people, you didn’t know people by name and more importantly for me, it became a little bit more bureaucratic.

Those wild ones, I guess where it’s like, “I want to get this done,” even though you’ve got to go to this chain of command and that chain of command. I think I just wasn’t running on all cylinders anymore.

And so, I think there was a time where I realized that.

The thing was once I realized that, it was probably a year, if not more, maybe a year and a half until I left, because this is your baby and you have millions of dollars in equity, right? And so, you want to see that through.

So, you’re so incentivized as well. And plus, your best friends are some of the people you started it with.

So, I had to spend a while finding another person that could be the CRO. And once I found that person, I saw and told my partners, but I think once that person was ready and I could see it, it’s almost like you can replace yourself.

And I mean, that’s the biggest thing a founder has to do. They have to make it so that they’re replaceable.

Of course.

And so, you have to pass those relationships and soon you very quickly realize that everyone is better at doing their individual job than you are.

So, the manager was much better at managing people than I was. The individual salespeople were better at selling. Maybe together, you’re pretty good at doing all of them, but I think it was once I saw that and my feelings hadn’t changed that I knew-

And also, with your partners too, we grew up as best friends.

So, once you start like that, sometimes as you’re going through that, the relationship changes a little bit.

And so, I think I realized, there’ll be like a year where it might be like, “Wow, we didn’t expect this,” but very quickly I knew that just give it some time and the relationship will go back to not business.

And I think I was so fortunate to be in that position, because working with my best friends, they were able to tolerate me and everyone has their idiosyncrasies or quirks or the way they work.

And so, I don’t think I would ever be in the tech world if I didn’t start this with people that were starting alongside with me, and were good with that. But I think the biggest thing was like, “How do I grow and how do I take those skills to something else?”

So, there’s a lot that happened in BloomNation we can talk about, but it was just an amazing experience.

The company is doing great. But I think the other thing is from an entrepreneur or financial perspective, when you have two great partners like I did and I think it’s your time, it’s time to put another horse in the race.

Because the way that I look at it is tech companies all have the ability to go billion or bust. And so, it’s like a poker tournament.

And so, I wanted to maybe enjoy the building process and so was excited to do that, but yeah, there’s a lot that went there that was incredibly helpful, because again, take business school.

I was just like, “Wow. Business school is totally just like a classroom exercise.”

I haven’t been sued before. I haven’t had people yell at me. I’ve hadn’t had to fire people. I haven’t seen people cry. I haven’t had that feeling of seeing that bank account and comradery.

So, the real world just excited me.

Well, you touched on something. I think it happens with most entrepreneurs, right?

Because usually, when you’re an entrepreneur, you start with a passion for something, whether you’re, like, solving a problem or you’re just got a real serious interest or passion in something.

And for me, that was SEO, right? I just got into it.

Like I said, I was doing SEO for poker companies. I would geek out over reverse engineering strategies and figuring out, “What can I do differently to have a competitive edge?”

And then from there, one thing leads to another and now, people see that you’re good at this and they want you to do that for them, right? And so, that was the genesis of the agency.

And then next thing you know, now, I’m not spending so much time geeking out over link-building and whatnot.

Now, I’m having to do accounting or HR, right? And then you start to do things and next you know, I’m not a SEO anymore. I’m a CEO.

And so, I don’t know how to be CEO, so what do I do? I get a coach to help me how to be CEO, right?

And so, yeah, there is all of that.

And I think every entrepreneur goes through that, but eventually, if you’re good at it, you end up finding people that are much smarter than you at the specific roles that you’re not really good at or you’re not passionate at.

And that’s the secret for success.

Yeah. I mean, you can’t scale a company yourself.

No. It’s impossible.

Okay. So, BloomNation, now branded as what?

Promenade Group.

Promenade Group. So, you now have a new venture called-

Whippy.

Whippy. Yeah. Okay. I want to know where that name comes from, but I also want to know a little bit more about this venture.

Yeah. So, left BloomNation right as COVID was taking hold and so I think even before I jump into there. That was probably the most adverse year for me.

So, I know a lot of people went through highs and lows during COVID, but when you’re starting a business and you’re looking at a white wall and you were at a company of 100 people and now you’re trying to figure out and you don’t even have the idea.

Just your intuition or gut said, “You just got to start something new.” It’s a pretty trying time.

So, I’m there and trying to figure it out, and we started walking, actually, around to different vendors because that’s just what I knew.

Go talk to a lawyer, go talk to a dentist, try to figure out what they need.

And so, I think I didn’t really have the right idea. I started testing stuff, but it was at that time actually that there was an engineer that was at BloomNation that I was really fond of and we chatted a lot.

He was actually working there. He actually, believe it or not, was from Ireland and happened to come on a one-year program at UCLA.

So, just really was excited with what we were doing.

And so, I remember when I was leaving, his name is Jack Kennedy, he was like, “You know what? I’m finishing my master’s in mechanical engineering, but I just love this entrepreneur stuff. I want to stay.”

I was like, “You don’t want to finish?” because he was just here for one year. “You don’t want to finish what you’re doing?”

And it’s like, “No, I’ll give it up.” He’s just on all cylinders.

And so, I remember thinking about it- Because it happened to be that he wasn’t a full-time. He was just here at UCLA and somehow got paired up with us. He’d seen some job posting.

He was just like, “I want to work for a couple months while I’m here, 6 months.”

And I was like, “I got to be honest with you. If you are doing that for me, I’m actually leaving the company. In 2 months, I’m going to announce it.”

So, he happened to be one of the first people that knew.

And he is like, “No, I actually really wanted to work with you. Even though you are sales and you’re the talkative one and I’m more interested in engineering, I just liked your approach and how you worked with people.”

And so, now during that year, fast forward to the next year where I’d already left BloomNation.

He happened to email me from Ireland and he is like, “I don’t know what you’re doing, but I’m about to graduate this year and love to just especially shoot the shit with you. Just see what you’re up to because once I graduate, there are a lot of people that say this, but I really have the entrepreneurial itch.”

And so, that was in 2020 and happened to be just finding my own purpose, so to speak, you could say, testing different ideas. And so, probably one of the best things that happened to me was that email he sent me.

Whoa, he took action.

He did.

And I tell you something right now, so he’s my partner now. I’ve just never seen someone take action at this level. And he’s 25.

Wow.

So, that segues to the next part.

And so, we started experimenting with ideas. He had graduated that summer of 2020 and he was like, “I’m going to come back to LA.” He loved LA, loved California.

But of course, you just couldn’t at that time talk about it.

So, it was a difficult time, because the person I actually thought like, “Okay, let’s try to start some stuff,” couldn’t come over. I couldn’t go walk into businesses anymore. So, someone who’s an extrovert and loves people, it was difficult being stuck in an apartment and staring at a wall.

Of course.

So, you struggle a lot, to be honest with you, that year.

I tried a couple different ideas. I left my company. It was a different type of wake up. I woke up when I was at BloomNation. I didn’t feel the purpose.

Here, it was just like, “What am I going to do?” You know what I mean? And so, that year probably, the best thing that can happen to me, because all of a sudden, you’d have to figure out your finances.

I was coming from a poker world where there were some times in the poker world where I would wake up and I would realize, “Oh, shit, there was $500 bucks in that pocket in the washing machine.”

So, you had no structure, you know what I mean? And so, BloomNation prepped me for some of that, but I had to take control of everything.

And so, it was probably the hardest year I’ve had that I can remember.

Wow.

But having Jack there, I was going through ideas and this is a good chance for someone to jump ship on you. You know what I mean?

Even if they wanted to work with you and he seemed to be getting more excited.

Motivated.

Motivated. Yeah.

And so, we started looking at stuff like web platforms. We were looking at an on-demand staffing app that we could build. There’s just a bunch of stuff we look at.

So, you didn’t have an idea for a business yet. You guys are just brainstorming.

Well, we were doing what you probably know, which is faking it until you make it.

So, go with an idea and call vendors. This is maybe me honing on the Persian side, pretend you actually have it. So, you have to.

One of the smartest tests someone ever told me in business was someone who I think eventually one of his friends had exited a company very quickly for a couple hundred million bucks.

And it was an eCommerce idea, but to see if it actually worked, he just made a quick Shopify website for $50 bucks.

Sure.

And anyone who purchased, they just said, “Sold out.”

But he just wanted to know if he ran ads, how many people would’ve purchased that theoretical product? He just proved it to himself.

So, I think that first year, we were trying to prove something to ourselves and I mean, we weren’t doing bad. We had one business that was making something that you could pay yourself.

But I left BloomNation to re-energize and to try to make a billion dollar company. That was the thing. You’re hungry for it.

I left BloomNation to re-energize and to try to make a billion dollar company.

So, finally, towards the end of that year, one of my friends, my best friend, the one I mentioned in poker, I went into his office and it was just like a mess. They were not following up with leads. They weren’t tracking things. When someone needed someone, it wasn’t going to the right person.

So, I started looking at that.

And then I had a friend of mine who was actually in staffing and he was using text message, but he wanted to use automation. If someone texted and said, “How do I apply?” Just automatically send them the job link.

Why are my employees manually doing that?

If I need to send it to 1,000 people, I want the software to know who opened the job application link and automatically just remind the ones that didn’t, functional things that people spent a lot of time doing.

So much time.

Automate it.

Again, I was still working on another idea together and he is like, “Hey, I’m just going to try building something.” And it’s been a year, so it’s gone very quick. It’s been a year since we started this.

And now, we have hundreds of customers, which is just awesome. At this point, I know that’s scalable, right? Sell everyone and onboard everyone myself and probably back to working crazy hours again.

But when you didn’t have it and you were just going through what is it, the second you grab something, you’re more likely to just want to go.

And I think if I left BloomNation and I just had that, I would just think I’m a king on a chair. You know what I mean?

And so, you had to fail fast to just get that hunger again.

Sure.

Well, you sound like you’re the person that’s like me. You like agile environments, where you can just quickly shift and change and not have to go through all the bureaucratic red tape every time you want to implement an idea.

And it seems like that drives you a lot more and why you like that world of chaos, I guess, if you will really, right?

For sure. Yeah.

Would you call it just an SMS automation solution? Is that what Whippy is?

I think we’re moving so quick that we don’t know what- So, right now, Whippy is focused on text messaging and a bunch of different use cases.

For the example of the lawyer, the PI lawyer, what did they want? So, I just started watching them and they do a lot of Facebook ads.

So, what they were doing before was having to download a spreadsheet and spend a lot of time.

And so, we’re like, “Okay, let’s integrate this with Facebook ads. Let’s text the person that was in the accident and if they don’t respond, let’s text them this, this, and this.” You know what I mean?

Let’s do things so that your team doesn’t have to.

And then the case of staffing, I went over it. There were even doctors in the cosmetic space, orthodontists, people in plastic surgery that were all about ROI.

So, Whippy is really an automation and it uses some AI. It’s really cool, but specifically in text, but I don’t think that’s the long term vision. I mean, I think there’s so many different communication things like being able to understand how you email people or be able to transcribe calls.

I mean, there’s a lot of different things that in the end, it’s the customer that they’re all getting touched.

And so, I think if you bring that together, it just becomes very powerful but I think we’re lucky enough to find something, to be honest, that people are going to pay for from day one.

So, I think if you’re going to dream big, you can dream big.

If you’re going to dream big, you can dream big.

But unlike BloomNation where we raised 20%, 25%, this one, I decided to bootstrap, because when you do raise a lot of money, it’s awesome.

You get to have an office and I was enamored by that. You make an office, whereas the table, the class conference room.

Physically, our landlord at the time on the promenade was like, “I’m thinking about redoing this anyways. How would you guys want to build it?”

We made our own WeWork.

Oh, wow.

But the downside is that that money is still held or there’s rules or you owe to investors. It’s not like you can just go put that money in your pocket.

And I think now, I’m more hungry to put that in my pocket.

Got it. Got it.

And it’s just you and Jack right now or you have more staff?

So, I started a little bit differently, started off with myself, Jack, and four engineers. So, Jack first, then four engineers.

So, unlike at BloomNation, we outsourced the engineering. You come from a different perspective where it’s all engineers in the beginning.

But now, we have been adding some salespeople, some account managers.

Yeah. And one last question, Whippy, where did that come from?

Yeah. So, I don’t want to say my dog. It was really with my mom and my brother got a whippet.

Have you ever seen a whippet? I actually have it here. It looks like this.

Oh, the dog. Yeah.

Like a little Greyhound.

But the thing about it is that I was literally sitting there, and this is no joke, thinking of ideas. As I was starting with where we’re going, you gotta see this whippet. It’s the fastest dog I’ve ever seen, just like a dart, right?

And I was like, “We have to think of a name.” And I was like, “Whippy, because he is a whippet.” And that guy is straight and fast and just full of energy.

Your idea for a product is to be bigger than just text messaging or in the case of BloomNation, bigger than just flowers.

So, I think Whippy was just a cool name that can really mean anything.

That’s awesome.

Sometimes when you ask the universe, the universe gives back and that happened with me recently.

I wrote a book. It’s called Law Firm SEO, and it’s specifically for lawyers that want to do marketing with digital, right?

But then I wanted to write another book that was catering to everybody else that’s not just lawyers. And so, I couldn’t think. I’m like, “It has to be two words. What could I come up with?”

And I was throwing out names. I’m like, “I don’t like that. I don’t like that.”

And so, I’ve got a couple books and one of them is called Words That Sell. So, I literally opened it up. And the first word that I saw was “honest.”

And I’m like, “That’s exactly what I want,” because there’s so many people that are snake oil salesmen in the world of SEO. I’m like, “I just want honesty and that’s what this book is about.”

And so, now it’s called “Honest SEO.” And so, that book comes out.

But like I said, similar stories, sometimes you just ask the universe and it gives you back, right?

Yeah, for sure.

Well, I think in maybe 3 or 5 years, you’ll come back as maybe a billionaire with this project hopefully. Knock on wood.

But I want to wrap up with something that we call “Hennessey Heart-to-Heart.” It’s where I just ask you questions and then you just rattle off the first thing that comes to mind.

Okay.

It’s simple. What was your favorite subject in school?

I would say math.

Math. That’s what I thought.

Which of the five senses would you say is your strongest?

Probably vision.

Vision. Okay.

I need to see things.

How many languages do you speak?

Questionably three.

What are the three languages?

I speak English.

Farsi.

[speaking Farsi]

So, that’s Persian.

Hablo un poco español.

Español. Okay. Got it. I speak one.

What is your proudest accomplishment?

I think if I was to think recently, actually, probably the first poker tournament I won when I was going through that. I remember actually getting a little emotional.

I mean the World Series of Poker obviously is huge and raising that money and starting a company, but if I was to give you a curveball, probably that first poker tournament.

The first poker tournament where you came home to mom.

Yup.

Got it. What makes you laugh the most?

Prank calling people. Or now, actually, like I told you with my mom, it’s funny.

We all use Whippy to send out these texts to family members. Right now, I’m actually going from here to a rehearsal for my cousin’s wedding.

So, I sent it pretending to be the wedding coordinator.

That is awesome.

You got to share some screenshots so that we can include it in the post like responses.

One of my cousins is pretty sure that the wedding coordinator is hitting on him.

Really? [laughs] That’s awesome. I love it.

How would your friends describe you?

So, I think, to a certain degree, I understand people. So, I asked some of that recently. “What’s the good and what’s the bad?”

And he just said, “When you’re selling people or when you’re connecting with people, I think some degree of emotional intelligence is pretty important.”

So, I think I connect well with people.

Okay. Yeah. I would agree.

Aside from poker, what sport do you watch on TV?

I watch, actually, a lot of soccer. I don’t watch that much poker. I watch it once in a while, but love- I can’t wait for the World Cup.

And again, I’m like everyone else where I watch the YouTube 10-minute version of everything.

The synopsis of the games and stuff. Yeah.

But I love to watch soccer.

What’s your go-to karaoke song?

I can’t even think, but I just remember that when I was rushing a fraternity at Berkeley, we had to sing Cyndi Lauper‘s “Girls Just Want To Have Fun.” So, I really can’t go past that.

If you had all the money you could ever desire, what would you do all day?

I think almost everyone who’s successful and I’m not saying that I’m there yet, but my dad showed me this. My dad is in his mid-70s and he still wants to work.

So, I think even if I had all the money in the world, I would love to find ways to probably give most of that away, but I think I would still want to have purpose.

If I lose that and I’m just like, “Hey, this is awesome. I’m on vacation all the time,” I’ll get depressed, quick.

Of course, anybody would. Yeah.

Sometimes it’s just passing along the wisdom to the younger generation and teach them the way, right?

That’s true.

I learned in poker that if you just step back and you don’t still play the game, you’re not going to be teaching for long.

Sure. Yup.

Do you have any pet peeves?

I think the one in terms of business that I looked at is like poker, you never took anything personal.

We used to relish to go to someone and say like, “How would you play this hand?”

They wouldn’t tell you because they think you’re going to take their money. So, we were always open to feedback because we needed it.

But I think one peeve on the business side was it was just hard to find people that truly were open to taking feedback. And so, I remember in the beginning when I was the manager, and we cut that pretty quick, there’d generally be crying sessions coming out there.

So, we found professional managers who probably could go through the process and had the time.

But even when we had those managers, I had a pet peeve with people that just weren’t open- I wouldn’t say being criticized. That’s not the right way, but on really trying to improve.

And I think this last year taught me, even for myself, how vital self-improvement is.

This last year taught me, even for myself, how vital self-improvement is.

People open to constructive criticism.

Yeah, and I think it starts with yourself. So, I know that’s very cliche. I don’t want to get that vibe going, but I think you have to first look at yourself.

And so, I think that’s a big thing, people that are just not willing to do that.

Oh, it starts from you. Yeah. I totally agree.

Favorite type of ethnic food?

That’s good. I like that. Food we like. I love pizza. I love, like, Thai.

A bunch of my family are vegetarian. So, we’ve gone to some amazing vegan Thai places. I mean, we’re Persian. We like kebab. We love that stuff, but I think recently, Thai’s been one of my favorites, spicy Thai.

I love Persian food, man. Who doesn’t, right? Yup, so good.

Favorite childhood memory?

The first one that comes to mind right now is just we talked about Rolo, who’s a whippet, but when I was a young kid, I had a Great Dane and the Great Dane was larger than me.

And so, I’ve been told, I mean, I don’t really remember it, that I was falling in the pool and that this Great Dane was huge. The Great Dane is seven feet tall but actually grabbed me and my parents came.

Is that right?

Yeah.

Wow.

When were you the most disappointed in yourself?

I don’t know if it’s disappointed, but again, I think this, like last year, year and a half, starting a new company, I actually had a couple other friends who left their companies and they weren’t as fortunate. I think they’re still going through a cycle.

And so, I think maybe the first couple months, trying to- need a little encouragement or whatever, like entrepreneurs don’t need that. Poker players don’t need that.

So, I think there was a little bit of disappointment in maybe things not working out as fast enough, but that’s life. And so, you just have to somehow keep faith.

So, I think that was a big part of it.

Yeah. Sometimes entrepreneurs or people that are perceived to be successful, there’s a lot of things that are going on in the background.

Oh, for sure.

They’re not as vulnerable.

And I think the more successful they are, the more they had to go through shit.

Yeah, because they’ve built up this perception and they have to keep that facade, right? Yeah.

Last question, in what way do you want to contribute to making the world a better place?

That’s a very broad question.

So, I don’t know where to start there, but I think the one place I’ve learned that I just go back to the world is how important respect is for other people.

Same in poker, I’ll use that analogy.

If you don’t respect your opponent, they’re going to crush you. So, you have to be open. I don’t even know where to go with save the world, but I think one really important thing with empathy is to tell myself to continue to be more and more empathetic.

But I think, no matter if it’s your intern, your waiter, or your boss, I think having some ability like in poker and maybe that’s a good way to leave it. You have to put yourself in the other person’s shoes, and actually think of how they’re going to play the hand to outplay them.

And I think more and more people, including myself at times, need to put themselves in someone else’s shoes to really be there. And so, I think that’s something that from a holistic perspective I would implore on other people.

I don’t think that’s gonna-

No, I think it does change the world just because it’s contagious, right?

And if you’re rude to a waiter just because you classify yourself on a different level as them, I mean, that’s not living life, right?

No, no. I think culture in a company as you build it is the most vital thing, because I told you in the end, everyone becomes better than you at that individual thing.

That’s right.

But why should they work or your customers? Why should they refer people? And it ends up being you.

And I think the more and more you start to put yourself in their shoes in every single way, it’s hard to do that, the better you make the people around you.

Yeah, good way to look at life.

Well, David, it’s been awesome having you on this show. I appreciate you coming down here to the studio.

How can my listeners keep up with you and learn more about Whippy?

The more and more you start to put yourself in their shoes in every single way, it’s hard to do that, the better you make the people around you.

Yeah. So, the website’s Whippy, W-H-I-P-P-Y, dot A-I, pretty simple, so Whippy.

And my email is just david@whippy.co. You can just email me there. As I’m saying this, probably added david@whippy.ai. So, I probably will soon.

There you go. If they want to watch any of your poker videos, I’m sure there’s stuff on YouTube too.

Yeah, for sure.

Yeah. Thanks again for stepping by.

Of course. Thank you for having me guys. Enjoyed it.

Important Links

David Daneshgar’s Wikipedia Page

David Daneshgar on LinkedIn

David Daneshgar on Twitter

David Daneshgar on Facebook

Whippy Official Website

David Daneshgar’s World Series of Poker Stats