Why bootstrap after raising $25M from VCs?

it really is that question where it's like if you ask someone for advice they give you Capital if you ask them for Capital they give you advice welcome to fundraising demystify the podcast where we uncover The Untold Stories of successful Founders who have raised Venture Capital to bring their Visions to life join me Jason Kirby your host as we dive into the Hidden Truths of the fundraising game we'll explore different strategies tactics lessons learned from these entrepreneurs who have figured out how to win the fundraising game in their own way whether you're a budding entrepreneur just getting started or an established founder looking to scale your business this podcast equips you with the knowledge and inspiration to conquer the fundraising landscape episode 8 . today we have David Dennis all in one kitchen platform for teams and they've decided to not raise venture capital and rather bootstrap the business based on their prior experience of raising over 20 million for a company called Bloom nation that was backed by a16z in this episode David shares his advice on why he bootstrapped and what it's been like scaling would be to over 2 million in ARR let's get started hey everyone this is Jason Kirby again with thunder.vc and your host of the fundraising demystified podcast today we have David daneshkar with us from whitby.ai and we're excited to be having you to the show David thank you Jason thank you for having me excited to talk about my two stories and and any information I can pardon people that are are looking to either raise raise capital or not raise Capital excited to speak today awesome now we're excited to have you and you're excited to have you kind of share your story you have an interesting background having played professional poker and then gone on to race metric capital and now starting a bootstrap business so it'd be great for you to kind of just share your founder journey and kind of what led you to where you are today yeah yeah um thinking about how far back I can go but uh well I mean I guess I'll I'll try to be quick here but yeah I went to to UC UC Berkeley and they are actually somehow taught a course on poker at that point this is right in the Heyday of when Chris Moneymaker won so I'm dating myself but we taught statistics in public gaming so that got me super interested after I went on to be a professional poker player and ended up winning one of the World Series of Poker events um in 2008 and was interested in you know the business side of stuff and so became very interested and and I actually became friends with the owner of the Lakers his name is Jerry Buss and wanted to be a general manager at the Lakers but ultimately ended up getting his letter of recommendation to go to business school I went to the University of Chicago and that's where myself and some of my buddies from from college started uh Bloom nation which started as a Marketplace for local floors think of like Airbnb for flowers teleflorn 100 flowers they were a broker so we weren't getting delivered what we thought we were getting but it ended up becoming a back-end software so the florists actually kind of had their own shopifying this is early on this is probably 10 years ago where they can make their own websites their own marketing tools um so that was and we grew that through a lot of outbound sales um but to start that and I know that's something you mentioned one of the first things we did when we got the MVP was go back to play poker tournament won a 30k poker tournament I know a lot of people it's not as dramatic as it sounds like we weren't not going to move forward if we didn't but that did make it easier for us to hire our first outshore Dev team was that bloom Nation up until a couple years ago and decided to take a little break and one of the engineers that was there um uh his name was Jack Kennedy he also left around the time I was leaving he actually wanted to stay there and forego finishing his Masters he was at UCLA doing his Masters and came to me and I said well I'm actually just going to take a sabbatical and so he went back to finish his Masters in Ireland where he was coming from and then we we linked up two years ago and we're really interested in like communication automation one of the biggest things that I learned at the nation which was obviously as I mentioned venture-backed was how big like the addressable Market size was or how important is to build infrastructure to kind of scale so we're so focused on local florists and that's what investors were telling us at the time you have to be the best in x but I think at Whitby um we realized that a lot of people needed AI based communication or they needed email and SMS automation or they needed deep Integrations with a database or a CRM that they weren't getting from that so that was harder to focus on it opened up a lot more doors as we as we scale and so um as I mentioned two years ago started uh Whitby and now small team I think we're 13 full-time and I've never raised any Capital so very different to my story of Illumination where I think in total uh we've raised over 20 25 million yeah so you raised 25 million for Bloom Nation but for whippy you've completely bootstrapped correct completely I think yeah I mean I think maybe and this just shows you it's possible I think maybe in the beginning I issued myself in terms of uh a loan to the company but a very small loan and part of that actually which pushed me to do that was that I hadn't exited uh Bloom Nation so I think it's a little bit different and I know in your own story you've had some exits I think if you do get this big exit I I think I've learned that sometimes you not to say you'll start things irresponsibly but like you're not looking at all the little things that may drive a company because it's not life or death and here we had to start something else well I still had a lot of equity in another company where I didn't have I wasn't sitting on a huge amount of like a capital exit so that made us get crafty and I think it's really true like the saying that people give you which is you just find ways to do it even if you can't and so I think being bootstrapped and also having that experience I found crafty ways to make sure that like directly or indirectly every decision you made like had good unit economics had because in the end of the day it's it's that there's nothing else but Revenue that drives the company if that makes sense there's no other external source of capital yeah and honestly that's that's in fashion these days you know I think uh after the big bubble adventure Capital over the last couple years in 2020 2021 you know we're seeing uh a refocus and a realignment on VCS actually wanting to back more bootstrap businesses people that had to get Scrappy that were more sustainable that had actually figured out their unit economics before raising Venture Capital so that when they put in a dollar they get three dollars back or ten dollars whatever the you know metrics are and uh so I think it's interesting to hear that story and also like you know probably a lot of Founders would think oh he probably made so much money on Bloom nation and it's so easy for him but like you know here you are like sharing your side um of the experience of like no you you still had to to kind of bootstrap you still kind of how to make things where it get Scrappy um so I'd love for you to kind of share your experience in the the you know from Bloom nation in terms of why you raise capital I believe a16 a16z was uh your seed investor uh and then you went on a raise subsequential rounds um so kind of walk us through you know a little bit about that history and how you guys want to go about raising money and now all these years later reflecting back on what you would have done differently yeah and I appreciate this podcast I think sometimes like you said you only hear I don't know how many times I go on LinkedIn even between Ventures when I was starting again it's hard to start because you see all these success stories but I do think you know that that that little poster where there's this huge Iceberg and a little tip on the top where you you see the success how much goes underneath so I'm hoping some of that would be you shed here with your other other speakers um in regards to Blue Nation was it was a cool you know I went to a cool fun story uh I went to the University of Chicago and in the University my two co-founders at the time were playing with this idea of the marketplace like tele floor and 1-800 Flowers wasn't servicing them when they were sending to their girlfriends and so it first of all made my experience at the University of Chicago much better um but when I went on so just you know the first actual round or first amount of capital was the school because the school had their own like business competition backslash minor incubator and so I think we won the school competition and that's a great program by the way like GrubHub Braintree a bunch of big companies have come out of that same University of Chicago um University of Chicago um program so that's been that's been a big feeder um we came here and then really quickly we did get actually start start doing some fundraising and I think the main reason why which is very different is we had Revenue in a lot of customers like again we were hustling and we had I think at that point hundreds of florists using us um and and some nominal Revenue now before that the story that you know um to get the MVP none of us were technical Whitby my co-founders technical has made a huge difference in terms of like balance and responsibilities and being an expert but we had to go out to an outsourced agency which created technical data and problems but also at the same point in time like maybe at that point in time versus now we couldn't get up and running it now there's so much no code in all these these Solutions so yeah we got Bloom Nation up and running um we had some traction going we had floors that were signing up and then I think yeah it was Chris Dixon actually who was a seed investor who wasn't at Andrews and Horowitz yet who had then moved over who brought us and introduced us to Jeff Jordan we became very good friends with an investor in in Andrew Parker who I think at the time was at spark capital um and then and then mucker Labs we went through we decided to go through the incubator mucker um and they invest in us as well and they've been very successful and so that's how we kind of raise that Capital we raised the one and a half seed at the time and then a five and a half million dollar round about a year year and a half later where where Ronnie uh Conway Jr came in and so that that was all good I mean Johnson was really fun and all the stuff that you say makes the whole process a little more sexy I think where it turned was when we realized that we were kind of like in today's world where we realized we were running out of Runway and we actually had to have a recap so that's a very different process and some of the things that people will experience now which maybe no one experienced back then it was in 2016 where there was this one period of time where it was a little bit difficult at fundraising I remember going into like a a board meeting or a visit and we're like oh by the way we have X amount of Runway and the investor there was like what the hell you know what I mean and so we went through that experience which happy to talk about I don't know if people here know about a recap but essentially we had to go to our current investors and be like where where this is a situation we are a good business but like cash flow wise there's going to be an issue and yeah I think it's kind of like called like pay to play where the investors you'd have to follow on or forfeit some of their ownership so so that was also a little bit of a messy time and it did give at least myself and some of you know my co-founders and stuff I would say a little bit more of a hardest steel because we had to go through that heart attack where I think that's what's happening to people now if I'm not mistaken they're going through those type of Recaps so we went through that in in 2016. so I think it did that did Forge some of the mentality that I now have on like never wanting to go back there again uh I think it's uh you hit it on the nail that's what a lot of I would say like series people that were expecting a quick series B after raising a a frothy a series a we're in for you know an even like seriously like we're in for a rude awakening and having to deal with Recaps because it just everyone thought money the money train would keep coming and everyone told them to burn all like at all costs you know grow at all cost and uh you know now just PCS change their mind and they're like no we don't want that anymore we want profitability sustainability unit economic like important things to have but it just wasn't the part of the conversation I think ours was a unique unique company too by the way start interrupt you but like we were actually doing good Revenue then so I don't think we've ever from historically from elimination and I think that has to do with the address while Market size gotten like a really good multiple like whenever we're raising money like we were we were also producing everything but you're right what ended up happening is her expenses were higher than the revenue so the recap actually made us think okay like how in in two months does our Revenue stay here but our expenses go here and therefore we are like carrying our head over water but we were today when I see a lot of companies it's pretty strange because they go through a recap but like there there is no plan there was no necessary revenue does that make sense and here the recap to me was almost like a float because we just need to adjust some things and we were not to say we were fine but but we had that luxury that I think other companies didn't because at Blue nation's principle it was built the right way it was built with that in mind and so there was a huge Dimension I mean if we had like something like pipe or some type of like forward your subscription software now we would probably have been been okay but it was a result of of that and just timing yeah revenue-based financing is one of the amazing there's a lot of debt solutions right now that have become very popular to kind of if you were smart in this market to kind of manage and generate revenue and you just really need some time to get to break even like it's a great kind of stop Gap and yeah it'd be great to kind of share you know and hear from your side of just kind of like what happened after that that recap because you know as far as it looks like it looks like elimination is still actively running and hasn't been acquired or hasn't been a no you know exit um so what was your kind of what happened after that recap and then what's kind of been your exit Journey out of the Your Role there yeah so I mean I think everything was great before that but I think the recap was actually a good thing because it made us act more like an internal private Equity company right like we sat on our own like and that was cool like especially for myself my other co-founder my the one that was a CFO was more prepared for this but I think for us it made us understand like how to look at a p l and like like I said like how do we actually like let's say we're buying this as a an equator an asset now like how would we restructure this so that was really cool because I didn't pay attention to those classes in business school so the real world actually prepared me much quicker um I mean in our time it was a little bit messy in the sense that like uh everyone kind of had to take down instrument equity and the new stakeholders got it probably I would call it a deal and then what happened is everyone that was currently at the company had to like they would actually reclassify you shares to kind of get back to where you were so as a Founder one of the things that kind of sucked is um you know how you actually have this I know it's called qualified small business stock but you basically you you go and you file and you follow C Corp you follow it 83b election I don't exactly know if that's it but like yeah for five years yeah you get five years right that was one of the things I'm Persian so we don't like to pay taxes so it was one of the things I would tell my parents they were very excited but like things like that meant that we had to actually redo that like we had to get ourselves to back we issue stock to ourselves because we got watered down and we had to earn it back out for a lot of the former employees not their current employees or former shareholders that couldn't play to pay or early investors a lot of them lost a lot of equity so that kind of obviously sucked as a founder where do we go from there I think we got very fiscally responsible um Bloom nation is is humming now I mean I know they raised I left in the start of 2020 and I think in 2020 2021 they did raise another round uh because there was a huge shift right where people were starting to go more online and so all these e-commerce platforms saw boom um you know I don't know exactly where they are now but the company it's I think when I left it was like 60 and I think went up to 120 and I think heading back down maybe to 80 or 90 as people get more fiscally responsible I know they've tried to double down on some of the stuff I touched on earlier which was how do we increase our adjustable Market size so I think they're trying to become a platform for the liquor shop the butcher whoever uses other platforms um like like they're looking at fragmented fragmented the carpet cleaner I don't exactly know but um yeah I mean the company is still there and I'm still an equity holder in it I think when I thought back when I left and like the traditional again this is a great podcast it's not always what the movie says I thought okay I'm gonna leave and here's my big track and on to the next but I think that would have also done a disservice because I don't think I would have been as Snappy or as an operator most people that run through that just can't get into the grind again and I was hitting the cold calls again why because I had to but I think that created a culture for us now at whippy which um is is kind of the way like it's like someone plays football or and you have a chip on your shoulder you really haven't won the Super Bowl you gotten close and maybe you know that that will happen and so I think that did create a drive in us and yeah the company's going going well there's actually some crossover some of our my old customers that are floors actually use my new new platform but it's totally been where I was all in or or not and and I was on the board for a little while and then gave up my board seat and I think that opened a new door where in the beginning uh myself and jack it was just like trying to figure out you know product Market fit and testing things out and seeing what people wanted and who would pay for contracts before a software's out and that type of stuff but yeah I mean that was a little bit of my experience there and happy to share anything else and give any other questions no I think that's an amazing story especially because you know the the ups and downs you went through with illumination and then you know basically electing to start over again even though like blue nation is stable and growing and humming you know you kind of chose to to start over because it was the right decision for you and um you know you didn't get a big payday no hopefully you know maybe down the road or however things work out that that happens for your secondary options down the road but yeah I'm cheering for them that's for sure but yeah I'm also ensuring I'm cheering also for myself and I think that's one thing I can answer for other people that are even Founders I kind of think of like poker because I know we can talk about that too but I play professional poker at one point been like this is way back 2006 2007 one of the top top holding tournament Players I think you need a couple horses in the race and I think if one's going well but you also don't think personally maybe you add as much value as you can or you may want to go somewhere else like it's also good because that's going well this is going well and you want a bunch of I mean not to gamified but a bunch of horses in the race you want to have a different different options or outcomes um and I think that's kind of what we're doing here with Whitby we did see some things at least me personally whether it's from fundraising whether it's on the adjustable Market whether it's the customer base that I wanted to kind of how would I say that take those learnings and kind of try it like I mean classic things to like when you're a SAS company you have an account management you don't want to skill linearly with customer service right so we're kind of used to x amount of counts add another person and we want to know how to whether it's automate or documentation or or certain things that like you know even you could even Outsource some of that and so I think there were things like that around the fundraising and mainly we'll talk about around bootstrapping and having your own destiny be your own decision which were some of the things that I was intrigued in trying in my premise with Jack for the next company was we just wanted something that could touch so many clients if it worked out and and that was hard because it was so broad that it's the opposite of what Venture companies would tell you to do which is like focus focus focus on being the best in one thing and one virtual yeah I saw that on your website you know you kind of list a couple different verticals you have a whole separate pitch for you know whether it's insurance companies or real estate agents or whatever it might be and kind of tailoring your message across each vertical but giving you you know your Tech can technically be applicable to multiple verticals it's just a matter of positioning and making sure that that particular customer Persona recognizes the value uh and again like yeah VCS typically wants you to be perfect and down one lane but the beauty of bootstrapping is you get to make the right decision for your business the way you want to run it and you don't necessarily have to work worry about the Venture Capital you know game as much and if it works for you then you're gonna you may already have like PCS throwing you're like hey do you want to chat you know uh you know if you figure it out and you kind of get Off to the Races um so I guess you know give us a little bit more context on whippy and kind of you know what stage you guys are at and kind of how you've you know kind of structured your team and you know what would be you know well I'll ask more questions later I don't want to Stack questions on you no no it's all good so I mean I can get more into illumination but when I left uh you know it's somewhere around 100 people my my actual title there was more of a cro here as a CEO uh I didn't even know what a cro is I probably still don't but what mainly I was responsible for is revenue like getting it and keeping it and scaling it so and I like the you know I always hear these things now about are you sales LED product LED and I think they kind of intersect but I was someone who enjoyed the prospecting or hunting um so so with whippy I mean I think I alluded to it a little bit earlier but you know we I would almost say that we acted as a as a Tech consultant or something so what happened is there was like a personal injury lawyer and like hey what's your problem and and basically all these could be solved in text or email but like oh I get these leads that come on you know Facebook and they fill out a form for an ad and my team takes too long to get to them and qualify them cool oh I have a bunch of clients and I want to know if they're going to leave me for another attorney okay cool we could send out this messaging via a mass message oh if they ever say the word Uber I want to automatically assign it to my key sales person because that's a huge case and so you need some automation or AI for question and answers it's very functional then a staffing companies started using us and they need to send jobs to thousands and one of the things that we started building was the back end software on on message I would say delivering throughput a lot of the SMS providers like we would look up the phone care of the recipient and there's something called a brand Square which is like hey you're failing at T we're only going to give you this much amount of messages and we could basically throttle it based on these kind of more complex formulas so that they could get more deliverability when they were sending out uh jobs and stuff like that so there was some of that as well but it really kind of started as an SMS platform and then we started realizing like oh they need to automate these workflows and so they use zapier Insurance stuff so hey if we could build automations inside ours so hey if you ask someone how was your experience one through five on your job yesterday and they say a five automatically send them a Google review link if they don't open the Google link and we detect that automatically send it again and since they gave us a good score three and ten days later ask them for a referral that's what those companies were having people do and we realized hey if we do a lot of that automatic quickly and then surface of things to people wow would that be more efficient so I I kind of kind of like functional Ai and so those different use cases are saying those are us just getting paired up with someone where someone tells someone or we go out there and send out cold emails and someone's like like I'm a pharmaceutical I'm a compound pharmacy and what I need my problem is to increase my refills and reminders and stuff like that and my serum doesn't do that and that's where we'll bring in like a product expert in Whitby who does two things they're almost like an entrepreneur Co in Residence at Whitby they'll look at like what are the needs and what's the market size like oh and they'll make a pitch internally if we build one two and three we could get this many pharmacies that use this many crms what ends up happening I would almost call it notion like is we just create blocks like there's automations there's campaigns there's these different things but then people can actually kind of customize it themselves where Partnerships has become a big thing like even marketing agencies that want to use our software or our API to enhance their own let's say software stack because they don't want to build a lot of this so so whippy is a communication platform focused on SMS adding email down the road voice um that utilizes a lot of Automation and Ai and it's being used to fill a lot of the gaps that maybe their CRM or their current workflows aren't doing um and again just to double down on how important that is we would go out to people and figure out how much will they pay will they forward us that money if we build this do you know what I mean so we almost acted like a tech agency in the beginning just because we were bootstrapped which actually means you can't take fluff you can't take someone who's like oh I will pay you this which is what you hear a lot of startups doing and what investors may say like in in the bootstrap World versus the world like money is the lifeblood of it so you have to actually do your best to pitch something that they'll pay for in advance right and then you just have to justify yourself are there thousands of others people that would utilize that yeah you say something so magical there like I was just talking to a founder and they were so sad on like giving away their service for free to get a logo you know like you know get a brand that says they're going to use their service you know when they start charging and you know they're trying to basically use VC money to subsidize customer acquisition and that just doesn't float anymore you know VCS kind of see through that and you know recognize like if you can't convince them to pay you then you don't you probably shouldn't exist um and so I think it's smart of you to just gonna go in there and it's like you're there's no BS you're going after customers that are actually paying you for the value that you're delivering and it's not like trying to manufacture or fabricate a story that will convince an investor to give you money to then you know then build a product that maybe the customer will use you know you're kind of going straight in for that that customer value proposition right away and listening to your to your customers you're putting yourself out there and kind of seeing what comes in and albeit it can sometimes first it depends on the business you know your check seems pretty you know scalable across initiative you know different uh Industries but I think that's something that Founders really need to kind of analyze and think about of you know how are they going to Market and getting their those kind of first customers and do they even need to raise money if they get uh you know they charge if you're charging the right amount and you're maximizing the the value because also you know with your website and you know I've seen a lot of kind of chat Solutions and you know Marketing Solutions and they usually start off like pretty inexpensive it's per user model and yeah I think you guys are kind of like in the you know mid-range and a couple hundred bucks a month and it's probably you know because you have that like you're replacing a human in some cases or you know augmented yeah I I would say it's pretty wide I mean you don't see it there are people that pass 10 or 20 grand a month so but there are people that pay us you know 99 a month it is it is and that's another thing I'll just tell you we focus with the potential to make this more Enterprise ready so not just doing things like HIPAA and Shock 2 and and those type of things but how do you support multiple users in multiple locations and multiple products that we can replace um how do you build some custom things for for larger clients um that can open the door for others whether it's like an integration or an adjustment to the product but no I think I would say that like you know on the the SMB side like if you think of some of the flower shops I used to work work with they'll use it for something it'll be at the lower price but then we'll get to a large firm that needs it from multiple locations and like uh to replace certain workflows as you said that people are manually doing and that and you want to build something where um and that's a big thing like I I want to continue to build where you can get 100K 1 million I mean whatever you can go uh AR contracts but yeah I mean that's been huge because we went to Market I would say last year so what is it 2022 and and yeah it's helped a lot like for us we have I mean you can do the math but we have we're a profitable company we have 12 full-time people um uh we have uh a bunch of contractors and we may intend to be profitable but what I will tell you is like we would go and like if it was like a if it was like a 100K contract or a 50k or 20 gig contract the first thing me and my partner would say is like oh that will enable us to get this type of candidate so it was Revenue that would get us to like it's like like electric double down on on the company which is really good because when you talk about exits and exit directions you know for Bloom Nation if you raise a certain amount of uh whether it's um you know debt-based revenue-based financing or or raise capital you know you have people on your cap table that have certain rights and can can kind of gear you to the direction you also they need to return something to their LPS right so here it's like if if we see the momentum going we can just keep doubling down and make our own version of a I don't want a good story of a like a zapier or something where people are able to kind of like their only money their rate is on secondaries if you decide to be like a 5 10 million error company right and like that's good cash flow for you that's still that's still a solid solid world if you want to and a nice exit so but I think you just kind of leave those options open and I don't want to sit here and profess like I know exactly where it's going as you said that was a story we had to pitch to investors I think right now we're enjoying the journey and like really driving well with our customers we just got back from a trip from Dallas where we did take one of the old playbooks added Bloom nation and throw an event in a city bring our customers in there invite new customers right like what better cold call is there to be like hey we're having an event at a pizza place and your competitors are coming can you come great you're going to be interested can you not come well this is a good reason to get on the demo so a lot of that we still are maintaining some of that localized sales strategies and B2B strategies but yeah I mean that that's uh kind of where we're at now uh with with Whitby so yeah and I think really and I've talked to a lot of you know bootstrap bounders that you know get to millions of dollars in revenue and just just by recognizing how to connect and better sell their customers and really putting all their effort on that as opposed to you know raising capital and like you know and here I am like I specialize in helping Founders raise Venture Capital but like you know trust me if like if you don't need it don't get it you know it's like one of the the things I try to encourage Founders to recognize if you don't need Venture Capital find a way to not need venture capital and ironically The Venture Capital will come to you you know I could very much see VCS reaching out to you and being like Oh you know would you be interested in having a chat you know yeah like as you kind of continue to get with it so I think one of your questions that you mentioned before I don't remember which one but advice or like how to raise Capital what I learned um it really is that question where it's like if you ask someone for advice they give you Capital if you ask them for Capital they give you advice so I think that is actually really true saying and I think it's almost like I mean anything in dating right if you're too aggressive or other people like oh and if you're not and you're offending someone someone's like why aren't they asking me out are they not interested so I think that same psychology I mean probably 10x it for the The Venture crowd and I think you'll probably get like what that formula looks like but I think you're right I mean we ourselves you know just crossed where we we just started and then now about just crossing around 2 million in AR and for us if you look back like a year and a half ago the truth is I would have told you that's only possible if we raise money um I think now actually it's really interesting when you do the math and like you know you grow and you have that type of cash flow it's almost like you raised a four or five million dollar um series a or seed um you have those logos but I do think that by forcing yourself to kind of do that you'll tell yourself this is real or not and one thing I can impart on the listeners here is is the worst thing to do is be in a gray place I mean it's always good to find out like is this viable or not as soon as possible because we only have one life to live you know what I mean and so like if this isn't it I know so many people started 10 companies that was the 11th or the fifth but the thing to do is convince yourself that it is when it's not and your best friends it's hard for them to tell you but your customers will people that pay money they pay for opinions with the green cash so I think that is something that is at some point something that people don't want to do because they may not want to get the truth or they're not ready for it yeah no I would uh completely agree I have Founders myself included like pivoting pivoting pivoting because not getting that that signal from customers of like yes and you know like oh yes please take my money and more and if you're not getting that signal like clearly it's not hitting you know product Market fit but I still see Founders like that are able to raise despite and you know trying to throw money at the problem when they haven't even found the real problem they're trying to to solve and you know one of my close friends out here in New York is you know I think he was on his ninth pivot with him and his co-founder like over the last two and a half years like just nothing but pivoting pivoting pivoting they only raise I think a quarter million for one of their ideas and or maybe a half a million or something like that they kept at it in their most recent business in the AI space because they were like Trend hopping and they just hit half a million a month in uh mrr in like six months just went from like zero dollars in monetization to half a million a month and you're just like all right that's product Market fit you're good to go and they had term sheets flying at them before they even really went to Market um and it's just it just goes to show like listening to customers and kind of listening and you know being willing to to kind of pivot and kind of make the decisions that um it leads you to customer satisfaction and revenue as opposed to kind of giving things away for free and subsidizing it with uh with outside Capital um so I appreciate you bringing up that that point so one thing we didn't talk too much about I think would be a you know fun is to kind of tap in a little bit more in terms of what you leverage from your poker experience I know it was years ago when you were you know active I'm not sure if you're still playing in any you know capacity but you know what are some of the lessons that you've leveraged or you know skills that you leverage from your poker history to kind of build your company raise capital and get to where you are yeah I mean that's that's a good question hmm I mean I think one thing about poker I always tell you that I've learned in business first of all so poker is a little bit like a timed game you can't sit there and think forever and you have to have a lot of muscle memory like I've seen this before but you have to decide quick and I think that's kind of indicative of what I've seen Founders be successful which is like and something that I'm always working on myself which is like quick decision making I think one of the things I think for myself to some capacity as Bloom nation grew but also at much bigger companies there becomes this level I want to say bureaucracy because that may be something but like you get in meetings I think what you're seeing now people are letting go of a lot of what do they call it middle managers because there's meetings on meetings on meetings I think there's so much to be said about something that just makes a decision and then even if it fails they move quick that would be like poker versus a meeting like you can't go to a poker and say time out and like here's a meeting and timeout guys this is the meeting about the meeting about this hand and like I'm back in you have to decide quick on live and die with it and a lot of times you're wrong but I think that's been helpful my partner Jack's done a fabulous job of of that as well on the technical side of stuff so I think that's one part um that's pretty I think another one that I'm currently working on as well but it's like tilt I think to a certain capacity in poker I don't know if you play poker yourself Jason do you yeah yeah it's been a while but I was pretty active back in 2006 as well you know playing online about friends all the time I mean we see it in business especially wearing a bootstraps and there's gonna be a lot of volatility and it's it's a good example of bootstrapping because you're a bankroll so poker players go under a lot of stress because they have a certain amount of bankroll and if they're out they're out they have to go back to getting a real job so I think in that world like if something knocks you off your feet in poker the best players when you think of the Phil Ivey's of the world they're like very even keeled like they're somehow able to like get through them I've seen that with a lot of Founders too especially when you have other people on your team because it's like if you don't do that and they start to see you kind of shy away or lose confidence or believe me there are mornings I wake up I'm like oh what am I going to do today how am I going to solve this but I think that's something that like the founders may have to harnessed and you need to make sure you kind of lead by example and so I think that ability to not get on to tilt as we said in poker is something that's pretty viable from from the poker world as well um as I mentioned and yeah I mean I think if I mean there's that whole cliche about reading people uh there was an example even the implementation that we raised an extra million dollars from just like making a read off someone and saying hey this is our last and final I think here whether it's negotiation or people um I do think there's a certain capacity to reading people but I do think in the end just like the execution and the variants those are things that go really well with the founders yeah no I I think that's a valuable to look at I think everyone's kind of looking for that like how do you read read people and kind of read situations but you're kind of quick decision making and kind of sticking with that decision uh I think is something that as a Founder like you just can't like I think some of the worst Founders have run into or no I don't say words but like what they struggle the most is you know paralysis by analysis and and that's kind of what you're eliminating with your background and your experience is not kind of falling into that trap where uh you kind of just make the decision make it quick and and take it to the decide another decision point where it's either worked or hasn't worked um you know so I appreciate you sharing that that insight and from you know I guess from from here kind of where do you see the the future of Whitby you know kind of what's next for you in this journey do you ever foresee yourself ever considering you know Venture Capital are you going to kind of stay the course keep it uh uh bootstrapped I think say the course I mean I think I mean this may motivate other Founders but the next round I want to raise is a secondary like I don't want my in in our world especially we've done something again I've maybe put myself in this situation as well but like as you want to have a family or you want to buy a house or stuff like that like I'm not under the illusion of like hey let me raise and let me do this and in 10 years like I actually have a lot of respect I mean obviously for for that path but also for like what our parents did or you know people that had to like you know to drive stuff now so I think I'll stay down that path um I'm very excited about the product my partner and the team I think we've done a really good job of creating a core team that I would take against anyone anywhere like I think that's been culturally a big thing and they've all kind of subscribed to where we're going we're adding other product Suite so I mentioned email voice going into other Industries we just launched an API so for a lot of these other systems that don't want to build off twilio or just like there's a lot of Dev resources to build something that they can build off our platform as well um I think I think that and just I mean honestly just maintain a high level of profitability and you know I I think focus on being a good company but also I think focus on making uh the right decisions and making money I mean I think as someone and I'm sure some of the people on this Podcast May listen to and I think you mentioned it there's a right time and there's you know if I had a company that needed a certain amount of capital and luck and I had proof points there but I just couldn't get to it without that like I don't know if I'm building a hardware or a software I'm not sure like those are things that are needed or if there's a real race with a incumbent and it's like a market grab winner take all type thing but I think for most businesses I think you said well if they start on this path what's the worst that's going to happen they're going to make the right decisions if anything investors are going to come knocked on their door and they can have that decision but here's the key thing they can dictate the terms not the investor when we had conversations before and you're going out to people the the powers in their hands and here if we do this correctly and that door did ever open it would be more that we were the ones that would um be dictating those terms because if not we were fine the way we were you know what I mean yeah and I find that uh that's going to be I think our our probably next two years of venture the companies that are getting funded are the ones that are more positioned like yourselves and those are the ones that we're taking on as clients are the ones that you know are hitting a point of profitability or break even have solid Union economics because you know the the math equation changes now for ventures of course they want their 100x return but they also want to see a clear path so like I give you a dollar you turn that into a ten dollar like they want to see the the equation and it's it's a much easier equation to build if you've already gotten a market have customers have you know profitable business uh I think I'll I'll throw a curveball in here okay I'll I'll throw a curveball for you guys already I think one path that actually doesn't get spoken a lot especially early Venture his Strategic investment like there was a situation or there will be where they're like big companies using our platform or CRM companies with our platform that to me could make sense especially like a secondary world where it's a win-win where you only get money but you're locking up contracts you know what I mean no I think uh that is something that is often overlooked and I think a lot of Founders are scared because like oh I'm gonna give up my IP at the show them what I'm doing and they kind of get hot caught up into not wanting to share and afraid of competition um but in reality it's like if it's that easy to steal you know you probably you're probably not doing it right uh that's something I always kind of you know rest on was like you should be able to present to competitors or to not competitive like uh strategics and feel confident that you built a product or a solution that is not easily replicable and that would be worth having and if that's the case like you're again setting yourself up for success to um like in your situation like lock down a strategic both as an equity partner to potentially help you scale or bring you you know basically be a customer so they're bringing revenue and cash um which could be a win-win across the board um and as you described more of a secondary so it's cash in your pocket not necessarily into the business so it's a nice little win for you um well David it's been amazing having you on the show where can our listeners find you or follow you or you'll learn more about whippy I think if um I mean they can go to LinkedIn it's uh they can go to Instagram they can go to Twitter it's either under Whitby or Whitby AI or you can uh check out our website there's contact information there as well I definitely think if there's someone listening and and they they think of a use case for them or a company or portfolio company that that is um uh you can also in you can email us at info info at uh whippy w-h-i-p-p-y dot Co or info hellowippy.com h-e-l-l-o-whipy dot c-o-m or find us on any of these social measures and happy to uh if there are other people that have questions about they're going down that path um always I think this is a great conversation as you pointed when we start it's just I do really like to myself listen to some of these podcasts that that do kind of show other sides of the the the story and yeah love to if anyone has any questions they can feel free to reach out to me direct awesome appreciate that we'll make sure to include those uh those links in the show notes uh for people to to learn more and to reach out but you know any any final parting words that you would like to share with the audience before we we part ways no I mean I think that this was a super um basically two side in terms of the conversation I think the main thing is there's not a there's not a right way to do anything I think based on the company based on the Tailwinds based on the industry I mean I think they're both I think that's the key thing I would just keep an open mind for both and really try to figure out but I would force yourself in the beginning and especially for the next couple years it sounds like to do this because I I feel like it's harder in the beginning it's harder in the beginning but once you do a lot more doors or a lot more control becomes um available to yourself as a founder no I agree especially in that bootstrappers we see World decision but David it's been an absolute pleasure having you thank you so much for for being on the podcast and I would look forward to just sharing your story to our to our audience thank you