Building Blackbird with Ben Leventhal

13 Jan 2025 · 58:32

a16z crypto general partner Arianna Simpson interviews Ben Leventhal, founder of Eater, Resy, and now Blackbird, about two decades building hospitality technology. The conversation covers his path from media to tech entrepreneurship, advice for early-stage founders, and how web3 infrastructure underpins Blackbird's restaurant platform.

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[Music] we're excited to welcome Ariana back who's GNA have a conversation with uh Ben lenthal uh so Ben was co-founder and CEO of resi which he sold to AMX in uh back in 2019 uh I think we've all used it uh and then uh prior to that founded uh one of the uh early food media called eater uh in the in the uh early to mids and is now uh working on Blackbird which uh you're going to hear more about today so please join me in welcoming Ben and Ariana well thanks so much for joining me here very excited for this conversation so Ben you've been like a huge part of shaping not just the New

York City Food scene but kind of the the tech intersection with food um for decades really and um I'm curious to kind of go back to the origin story of that and all the way back to the early eater days in the uh early 2000s you said 2005 right 2005 yeah what prompted you to kind of want to play in this landscape and and uh what led you to kind of the beginning of the story I think this group will relate but I think part of it is uh it sort of felt inevitable that I was going to be uh an entrepreneur and do my own things I think objectively a little bit of an authority problem objectively I'm

unemployable and so I it's a good thing I figured it out um no I think look I I am really lucky that a passion turned into a career it felt like the things that we wanted to talk about when we started eater weren't really out there in the world so I think we sort of felt like all right there's a lane here um we can do something new in food media it it feels like um there might be an opportunity here and more than anything else we just started doing it from their execution persistence and um and somehow it turned into what it was mhm and so um eer started out as sort of a a magazine

early blog really yeah what was the journey from that into like a full-fledged tech company like um you mean resi or just yeah well I think so well I mean feel free to talk about kind of the the Journey of eer and then into resi I think in hindsight one of the things that we did with eer and resi and so the common ground is that I've always sort of felt like restaurants are much more of a an entertainment category than they maybe get credit for I guess today things are a little bit different and you know we talk about restaurants differently than we did 20 years ago but 20 years ago there were five celebrity chefs and otherwise restaurants were just sort of places you read about at on City search or is a gat and I always

sort of felt like there's much more to restaurants they're much more exciting than I think we are letting on from a sort of coverage standpoint and and so we just started talking about them in a totally different way and we basically used the technology that was available to us at the time which is to say online publishing and we sort of pointed it at the restaurant industry and so something similar happened with resi where we said you know consumers are using mobile they're not on desktop anymore there's a bunch of obvious things from a technology standpoint that restaurants could make use of especially as it relates to marketing and connecting with consumers so we're going to kind of point the technology at at restaurants again and see what happens and I think

that in many ways is sort of the the commonality between them and I think you know obviously resi was much more of a full-fledged technology company we had our own Engineers we invested in our own product in Tech and we used mostly off-the-shelf stuff with eer but I think sort of thinking about technology pointing it at this industry where we had a unique Insight was was how one thing one sort of lets the other mhm and when did you start thinking about kind of what would become Blackbird and the whole you know that whole resi to Blackbird hop yeah I mean I think similarly you know as I was winding down my time at AMX and um thinking about I should have thought taking more time off

but I didn't um think about is that a piece of advice maybe again it was this idea well you know there's really interesting stuff happening on chain and uh not all this blockchain stuff as it was in existence in 2020 and 2021 is going to ultimately see the the consumer light of day but there's some really good stuff here there's some really interesting technology and some really interesting Concepts and what if we did point this at restaurants and what would that look like and it started with in two observations one is in terms of cryptocurrencies restaurants felt big enough to have their own currency as a category as a category it's a trillion

dollar in the US and two is when I looked at the some of the early nft projects those felt a lot like restaurants from a community standpoint oh interesting when you when you sort of think about Crypt punks or some of the other stuff that um was like popping you know it was just like or communities organized around a passion around a sort of a thematic thing or or um you know a brand or whatever it was and and a lot of great restaurants are kind of the same thing it's a bunch of people who have a similar affinity for something and it's not nfts but it's just a physical space in a menu but I felt like there was some real Common Ground there and so those were the things that I just sort of started thinking about which

ultimately uh led to Blackbird and I guess how would you sort of crystallize the main benefit for restaurants that blackbird brings compared to like you know some maybe some of the well we've talked about this at length but like maybe some of the issues that other technology platforms have had when interacting with restaurants the fundamental connectivity between restaurants and their guests is broken restaurants don't know who their guests are they don't have good access to data around their guests they don't understand how to think about the lifetime value of their guests so that's those are all symptoms of the technology e ecosystem that exists in restaurants the credit card processing rails uh the the Legacy rails when it comes to

admittedly things like reservations and certainly POS and and so that's really in the end what we're focusing on is giving restaurants simple tools to connect directly with their consumers and in the long run giving them access to data and um and tools to turn them into regulars and I've also heard you articulate kind of the the ownership piece right it seems like many of the existing um technology platforms have in some ways been extractive of value from restaurants as opposed to additive and the restaurants don't you know don't necessarily have a stake in those businesses where is in the network here that changes Pie in the Sky here is we're creating a restaurant economy of the future Blackbird and our native token fly is going to be the global

currency for restaurants and the whole Enterprise is going to be co-owned by the restaurant industry so we're shifting everything that that exists today and everything that restaurants are used to uh in terms of how they they relate and interact with their Partners especially their technology partners and in the end we do want it to be co-owned by the industry so resi has become like synonymous with making a reservation and you know you you were able to create kind of not just an app that was widely used but almost like a a new behavior um Blackbird in in a short amount of time has established it as well I think I'm biased but uh definitely one of the most recognizable and um and well-designed consumer experiences in crypto so I'm

curious like how did you do that with both resi and Blackbird and what are kind of the elements that you that come to mind when you're thinking about establishing a new brand for a company I think the important things are to understand who you're com customer is uh and from and maybe you could share the feedback yeah so I got some prep materials for today and included um descriptions of all the companies that you all are working to build and I think that you wrote those descriptions and I don't think there was a single one that included who you were building your product for um it was a lot of like we're building you know this piece of infrastructure period what was missing from all of them was the comma after

whatever you wrote and the language for consumers or for developers of blockchain solutions or for whatever and um so you all should add that as soon as you can as soon as you know um but it's super important when you talk about brand building you have to know who your audience is you have to have that person in mind or that uh group in mind um or wh whomever it is um otherwise you're sort of going to ultimately be r rudderless i to me the other piece of brand building is storytelling I think um every good brand that's ever been created ultimately tells stories and

ultimately you understand what their values are you understand where where they're coming from you understand what as a brand they get excited about there's adjectives you can associate with the brand um and those things are so important and you can't expect people to understand what it is that your brand is and uh what it represents unless you are communicating in those in that way um what your brand is and how do you think about you know I think um brand recognition can be both very tangible you know everybody knows it when they see it but also a little bit amorphous like are there particular ways that you think about measuring that or sort of how do you assess the progress that

you're making in that direction and if any course correction is needed along the way how should how do you and maybe how should folks um think about that to be honest with you I think it's sort of somewhat hard to measure especially in the early days I mean I think uh I guess I would say this if if brand is not one of your superpowers then you need to get somebody around the table fast that that does understand brand and that knows how to build brands or knows how to help you build a brand I luckily I I branding and brand building and storytelling especially because I have a background in content is something I think that I do I do pretty well and and is something that I bring to the table for the business but I

think part of it is you got to have somebody with that expertise if that's what you want to do and build a brand um and win on brand you you got have that expertise it's not a universal thing that people know like if you're not good at it don't try to be good at it it's not going to work focus on the things that you're good at um so it's easy enough to get those kinds of people around the table in terms of measurement you know I think a lot of it does like come out in just like your basic kpis like I think you know when you see da heading in the right direction I do think like you can connect that to Brand obviously when you're thinking about content as a as a way of expressing a brand in particular that's a fairly easy

thing to recognize and to measure you know it shows up in NPS it shows up in anecdotal ways as you're growing a brand you're going to there's going to be a moment in the in the journey where somebody in your ecosystem says something to you about the company and says oh yeah I S you know I saw you guys um or somebody mentioned it to me you know I saw Blackbird at this place I go to all the time in Williamsburg that's going to start to happen I I think that's like a strong signal of brand one of the things um that happened with with with eer uh is we knew we had something when the people we were writing about were

started reading the site and we started getting feedback from them they started directly emailing us the first chef who ever did this was a woman named Patricia Yao I think her her last name was and she um she had a place Park Avenue South and we wrote about it and she wrote back to us to say hey I just wanted you to know you know I think she was sort of wanting to somewhat correct something we had said but mean someone's paying attention somebody's paying attention exactly so you'll you'll feel it it's some things you can measure some things you can feel and and I think that's just sort of like the nature of of brand building um maybe double clicking on the

measurement piece because I you know know a lot about Blackbird and I I think you guys have some of the more um sophisticated ways of thinking about metrics and sort of looking at data of companies in our portfolio which is great and I think that's something from the consumer background that that you really bring to the table and maybe would you know a lot of folks in the web three space would benefit from from adopting some of that as well um so just curious like when you're when you're thinking about an app like what are the key things that you're um focused on like the way we think about this generally is we're a a VC backed startup and in order to keep the lights on you

know we have to keep getting through Gates and those Gates tend to be fundraising Milestones so you know there's seed and series a and series B and series C and and on and on and and uh one of your jobs is to understand exactly what the deliverables are at that gate like if you do nothing else and you know nothing else about your business you have to know that otherwise the lights are going to go off at some point and that's going to be the end of it and I I have to say I mean this is I've done this a couple times I've had some reps I've this is learn Behavior so um it's not necessarily something you're going to do naturally um but in terms of kpis like that's how we think about them like we know generally up and to the right is good up

and to the right is good but actually um up and to the right is you know you can always get the charts and always get the metrics to go up and to the right you need to make sure that like the signal behind that is the right signal and you need to make sure you're measuring the right things um so for us as you know tpv and da are fundamental da daily active tpv is processing volume because ultimately um we want to be in the flow of transactions and be a payments company but yeah I mean I think I think it's important to understand what they are and they're different for every business and by the way to go back to the the my point about like who's your business for like if you got to know the four to know what your what

Your KP kpis are and then you got to start tracking them right so so when you understand like who's a business for what is success and on that basis how do I think about success then the kpis come a little bit more easily from there um so you know as I said for us tpv da um and then there's a bunch of stuff that are just fundamental like retention matters like retention matters because if you're not retaining your customers the Eon the unit economics of growth are never going to work so some of it's you know the stuff that you could read any VC blog on the planet will tell you and other is is specific

to the business yeah makes sense um cool so shifting gears into kind of more leadership and and um your particular brand of it um you know you have a pretty laidback demeanor um but I have definitely seen you know bits of of wartime CEO mode uh start to emerge in certain context which I personally enjoy very much um and so I think that's you know not necessarily something that would be evident at first glance with you so I'm curious like how you think about um wartime versus peacetime CEO um how you would characterize yourself and sort of of how that plays into your personal brand of leadership this has evolved for me over time I think walk us

through the Journey well um I mean I'm I'm a fairly uh I'm I'm both straightforward and direct and I have a very poor poker face so I have to be direct and um I also bring a lot of intensity to what I do because I I think there's a lot of passion there and there's a lot of belief in in what we're doing and and belief in the importance of it and um I generally am you know a fairly passionate guy you have to strike a balance like I think I think uh two things not only you have to strike a balance um and you don't really want to go into that mode of intensity certainly if the situation doesn't call for it but

also if you don't have to but I think alongside that I found something else that's really important is that I think you really need your lead the people around you to really like fundamentally know where you're coming from like you really need your team the broader team for sure but certainly your leadership team the folks that like are going to be with you you know communicating the vision in many ways like your front line of execution like they got to know they got to trust you they got to trust that like you've got their back and they've got to trust that like when you turn up the intensity it's cuz it matters and and it's coming from the

right place and I think that that's the most important thing of all and it's really like if you bring the intensity um and you bring that wartime mentality without your team knowing where you're coming from you're going to kind of get they're going to get caught off guard and it's going to get kind of DIY yeah I'm curious kind of traveling back in time again what were some of the hardest parts of building resi and um were there any learnings from that that you've been able to use to really accelerate the timeline uh with Blackbird one is you know you're really all about your team um you you have to like team building is a

superpower and uh and you have to develop that actually and you know you got to like think of this as a lot of this day in and day out like it's kind of like a trustfall like you've got to let your team do stuff and you've got to let your you've got to like communicate what you want and ask your team like what what they think of that and like be super collaborative in terms of communicating iterating on establishing a North star whether that's for the business or for that's a project and then there's trust Falls like it's got to happen without you in the long run otherwise it's not going to be a

scalable business so that was one one thing that I thought was that I think I'm doing differently this time around that um that that I did learn um to some extent the hard way with resi and do you feel that you were not yet in a position where you could necessarily recruit the best people or you like more of a um you know question of of just focusing on that versus many other priorities maybe a little bit of both maybe a little bit of both I think if somebody had said like dude you're not you're spending all your time on you know willing things into existence and none of your time on team building and and you've got to fix that I I I don't

know hopefully I would have taken that to heart hopefully I would taken that view but it actually lead so the next thing that I would I wanted to highlight here is just um you know boards matter a lot and I think you can you've heard me say this a couple times now it's I'm going to use the word superpower again and I'll take a half step back and say the only way you're going to be successful is if you have superpowers you know what they are and you lean aggressively into them that's how that's how startups turn into real businesses so your your board can be a superpower I really think and um but you have to be very purposeful and thoughtful about board construction

and understanding how that how that all kind of works and um and really and how do you think about that one is is you want to think about like what are the areas of strategic leverage and expertise this business is going to need to to work like what are the things that we don't know today or uh that we don't uh have inous but we're going to need so I think that one thing to think about is like okay so for Blackbird you know um we we got to know we got to be on The Cutting Edge of blockchain like we have

to be you know not only do we have to be thought leaders and innovators there but we got to know like what is best practice and this and as as we all know here like this is changing fast so like we got to know can't buy a book on it no so that's like as an example for Blackbird like it's got we got to be cutting edge there um so you got I think you have to think about those things I think you also from a personality standpoint have to think about okay who do I want to put around me that's going to complement me um and then overall the chemistry and the Dynamics of the board matter a lot like you got to have you know a group of five people or seven people like who actually enjoy spending three hours at a time um having really

interesting but often like nuanced and challenging conversations and uh what's your take on inperson versus remote boards extremely uh important I think to have in person I really I knew the answer to that one I mean I contact and like sitting next to somebody it's I don't think you can get it on video conferencing yeah so what parting advice do you have for the folks in the room who are uh at the beginning of their entrepreneurial Journeys um take seriously the blocking and TCT of being an entrepreneur which is to say know the

know the fundraising Gates uh get in the weeds there like have that stuff and take it very seriously there's not a lot of Art in terms of that part of this um really understand the VC math that's on the other side of the table you can't like charm your way out of that math no slide no chart no nothing is ever going to sort of like mitigate the fundamentals on the other side of the table I don't think um so one job you have is to know that math really well and to be sober about it and to be realistic about it the second thing I've mentioned which is

know your superpowers and lean into those and obviously know what you're not good at and make sure you're solving for that and then I think the last thing is like you you got to keep going like this is really uh pretty gruesome work that we do and uh you got to keep going like a really good day is like two steps forward one step back like that's a 10 out of 10 um and a lot of days are going to be like man we are and uh it is kind of lonely because like there's not a lot of people you can really say uh I think it's all

kind of I think we're done here like I don't think this is going to work but you're going to have days like that you're going to be like there's no way through this and um you have to you have to will the next day uh into existence and that's really that's the job in the end amazing so I think we're going to open it up for Q&A now oh look at that a plethora of hands already very good hi um I'm Claudia uh you talked about how your performance at resi was capped by your team um I went through a pivot and laid everyone off and I had made a lot more hiring mistakes before that as well um I feel that my standards have risen

over the past couple years just like it sounds like yours did but I'm worried that they may not be high enough and do you have any tips for how you can accelerate picking like your own ability to pick and attract and then lead the right people like what would you have told yourself earlier on at resi to make sure that you had picked a better team earlier cuz for us it's it's a rush right now yeah that's a good question um I mean I think one tactical thing is I I actually believe way more in recruiters now than I did in the past I think good recruiters actually do matter a ton and not just because they're going to go and do a better job at um combing through Linkedin profiles than you are but you're they're going to be an important kind of sounding board as you think

about talent I also think another big one is uh I like to have people around who have been in the in past jobs like in cultures where there's been Excellence where they're they're Elite like engineering teams that I know to be elite teams like you want like uber you know at a in a period of time like those guys were absolute assassins so like it's not that you need to necessarily hire an Uber VP of engineering but like you want an engineer who understands what an culture looks like and can help you you know bring that to fruition so I think that that that matters a ton and then obviously like chemistry but I

think actually recruiting and like picking from the right places goes a long way Benny here good to meet you Ben um we hear a lot about hand toand combat um with you know going door Todo talking to restaurant owners like love to hear a little bit more about that like whether or not it was like strategic alliances with restaurant tours or you're not knocking on the doors of everybody like what started to work really well for Blackbird are you working with restaurants are you doing something with restaurants no oh for um I was curious competitors and no no um what the question is what worked from a sales standpoint yeah I mean you could tell your story better than anyone else so like you better be knocking on doors

like you're definitely the VP head of sales maybe start even with with eer or resi because I'm sure I mean I know for a fact things have been a lot easier with Blackbird because you like have all the people's phone numbers and so you just call them as opposed to before I mean I was the head of sales or resi I wasn't on paper the head of sales or resi but uh you know I was spending half of my time on sales at resi I still spend a ton of time on sales it's super important like um build builds credibility for the business like nobody's going to tell the story better I would think about that as your job Ju Just to f up do you have like a huge sales team sales reps SDR like well I mean now we do now we do and um and

again I mean we're a couple we're a couple of ticks out in terms of fundraising in terms of resources um so the answer is we do now and and there's real in whatever your industry is there's best practice and so you know you don't really have to reinvent the wheel when it comes to sales like you can you can tune it you can do things better than other folks you can understand like all right this is the best practice this is what we think works for the business it's not it's not that it's ultimately sales is an execution thing um you got to tell your you got to tell your story you got to make sure that the team has the right language you got to kind of like look at the dials and be like all right our close rate against this pitch isn't very

good so let's stop doing that but yeah say like there's you and you're the you're the best you're the head Storyteller for the company and so you should be knocking on the most important doors and you should be make sure that you're in the most important sales meetings certainly um the ones where they can have a meaningful impact on the business but really you should just sort of H be in a lot of sales meetings um by the way one reason obviously is because the person on the other side of the table it matters but also if you take a sales meeting with your seller and they see you selling the business they're going to get better at it right so it sort of has dual has little a second layer of upside to it so um you know on the team

building point how much was it just that people didn't have the culture coming into the team um how much was it that you just didn't spend the time to build it how is it possible to teach somebody how to be excellent you know how do you think about that yeah I so actually one thing I would I forgot to mention around this that I think is really important that we're doing with Blackbird and and I'm really excited about this work is you have to be intentional about what per what success looks like like you you shouldn't assume anyone understands what Elite Performance is you know I think when we look at this in the world there's a bunch of different versions of it like um once we sold resi to AMX I was there for 18 months and a

full half of your performance at at MX is basically like does your team like you like it's half it's it's half now arguably one of the things MX does better than anyone else is it builds internal superstars like if you've been at the CEO of AMX been there for 30 years like the next I remember that LinkedIn is really really wild the next CEO of AMX will be well it's I he start as like an intern or something like that I mean it's yeah the wild career progression they are really good at developing internal Talent like the guys at the top the men and women at the top of that organization like they just know what it means to be successful at AMX it's not for every company so the point

is I think a big part of that team building and that culture thing is just be really intentional about what success looks like and be honest with people like if if you want an if you want a team of people that are just going to run through a wall every day and like you want the intensity in an eight and that's like what it means to work for your company you just have to hire for that and you have to be honest with people that maybe like are Legacy hires and say like this might be not be the right place for you you know I think it I think we tend to not want to um not want to churn people once they're in the seat like you you

sort of are scared of losing people and I think that that's reasonable and you should be and um retention matters a ton but like I we're going through this process right now um of just articulating from a performance standpoint like what are we what do we value more than anything else and so you know for us it's are you Elite relative to everyone else who does your job are you more productive and are you helping your team become better uh oh sorry and are you are you do you have passion for what we're doing and that's that's what works for us it may not work for you but I think whatever it is you have to be um explicit and intentional about saying this is what we value in our people so related to Ben's sales question earlier

uh I'm assuming that a lot of the uh clients or prospective clients restaurants that you talk to they have limited if any knowledge of web 3 um so I guess I'm just curious about like what's your sales pitch there like with respect to to that part of the blockchain yeah we don't even mention it what difference does it make I mean I know some of you all are building blockchain infrastructure companies and to be honest with you some of the the nuan some of the te more technical um ideas are way way above my pay grade we are building a consumer product we are building a tool to help restaurants

connect with their customers I mean we don't talk about AWS we don't talk about the fact that our credit cards are vaulted with checkout.com we don't talk about that flies on on base it doesn't matter it just creates confusion it just creates uncertainty and it doesn't well it does matter but it doesn't it matters to us it doesn't matter to the rest of us right they just just explain the benefit rather than getting into we say you want credit card processing at 2% okay cool yeah makes sense thank you I understand how your like product Market fit is working with the restaurants but consumers are so fickle um how did you guys get that and I would love if you could talk about both the people that

made it happen the process they went through to figure it out and then the behavioral hooks for like the hooks and the Moes that you guys eventually figured out to get it right and get consumers not turning I don't think we're declaring Victory quite yet on product Market fit I think we feel like we're sniffing it out and and we feel pretty good about where we're headed but I mean I think a lot of it is in the that's in the measurement of that's in the instrumentation like you can be anecdotally excited about your business all day long you can be like we just did this crazy event it was awesome people loved it that's part that's the brand part the product Market fit part is like okay what's the retention numbers look like like how easy is it for us to acquire new customers like

product Market fit for me is the question is ultimately are you in control of your own destiny right so that that's going to be different for every business but I think you can sort of say okay you can check that box when no matter what like if if Ariana says like all right you guys have to be 25% up in three weeks like we could do it if we really wanted to and I think we're getting there for the record I'm not in the habit of coming out with like random asks like that but you understand the point but you understand the point like totally you that's product Market fit like is it clicking do we know how all the dials work so the other way to think about is like um and this I can't take credit for this this is out of this is

um Albert and Fred at USV but like they think about startups one analogy they use is like video games like you know you just keep you you you play level one for a while you got a master level one then you play level two for a while you got a master level two so you know it's it's all about like so product Market fits like level one like you just got to and I'm is probably an unsatisfying answer because I'm not giving you very specific um like a specific sort of checklist but you've got to look at you've got to understand the kpis that matter for your business for product Market fit and then you've got to see them work I I I think you you mentioned um a couple of things earlier on that I

wanted to double click on the first was that you have some I don't know if I'm uh in a position to phrase it as regret but I will just put it as that anyway about how you uh constructed the team in the previous Venture yeah that one really resonated yeah yeah yeah yeah it really does because I think that that one of the things that like I I don't know this is my third time being a founder and one of the regrets that I have in the past is I had this sort of blind loyalty towards the first 10 people that I hired and it sort of like found myself lowering the standard of Excellence of the organization to meet that loyalty need and uh it's not something that I want to repeat again and so it's one of those things is you

know organization's needs for the first 10 versus the next 90 and how many of those first 10 actually stay and how do you stay on top of that um and the second one was you said something about VC math so what exactly do you mean by the VC math um so is the first question like how to think about those first 10 well absolutely uh because do you just fill in gaps willy-nilly cuz you have like a ticking Time Bomb of I only have this much money and if I don't get something out the gate and then how do you equilibri that with quality so I would say I think the first 10 they definitely have to be people that are passionate about what you're doing these are not folks that are

coming in punching in a clock and getting a paycheck these are people that um will help you figure it out no matter what because they so they believe so deeply in what you're doing and they and they get it in in the same way that you do I guess I feel like you want to you do need some generalists in the early days uh cuz there's going to be things that come up that you can't really anticipate and you know you're going to find like your CS function like you need more you need more of that like sooner than you thought so like you're going to need somebody who's just like passionate and a good writer and a good communicator like they can start they can start to help you tree our Cs

and um some things are more as in Customer Support not computer science customer support um I I I don't think generalists in in specific areas like necessarily product and certainly not engineering make any sense I think you need that to me is where even in the first 10 like you need to be thinking about pulling people out of elite places and hiring real killers like don't hire a generalist who has a passion for product to to be your product person I don't think that will work similarly I think you need like your first couple Engineers have to be fantastic Engineers um if you can get them um and

then I think after that you know articulating values the sooner you can articulate your your talent values the better if you can do those on day Zero and you can hire right out of the gate great even if you don't and you start to articulate your values six months a year in as long as you're explicit about them people are not dumb right like people will identify in and out of those values and sort of it's not that hard if somebody's like you know I really am not I didn't sign up for this that's cool like we can still be friends what was the second part of the question VC math oh VC math um yeah I mean these guys have to make

money look at all this um every VC is different but it's based on fund size it's based on uh you know stage of fund but like they're going to put money in they're looking at your Tam they're saying if I own 15 20% of this after this amount of time it's going to get me X and does that return the fund that's the that's more or less what it is like it's not going to be like well this one's not going to be that big but it's going to be awesome so will do it it doesn't it's not going to happen like so I guess in the end like the math is a little bit different in

each fund and each stage and when I say VC math what I'm saying is you need to understand what the math is on the other side of the table you need to be sober about your Tam and you need to be sober about what you're selling to them because the other part of VC math is like when they put the money in they want to when they ask you like what are you going to do with the money they're saying like what's your plan to get to the next fundraise it's not like let's have a conversation about all your fun ideas it's like if I put in 2 million bucks today or 10 million bucks or 50 million bucks like am I going to get to mark this up in two years that's the VC business right I mean more or less got to make money like

it's it's fairly straightforward right so I don't I just don't think and again I do I think this is reps like you're not necessarily supposed to know this going in but hopefully a the benefit of a couple of my reps will help you guys like I think it's just what that math is what it is and that's why Tam matters and that's when they say when you talk about use of funds like that's what it's not a conversation it's like are you going to get me to the markup that I need to keep being excited about your business like these guys have investors too like they have they have to report out on each of the fund performance to their investors and like they need to Mark those things up to keep getting

money yeah I think it also comes down to knowing um you know somebody earlier asked the question like what are the expectations around a c deal versus a series a deal versus a b like understanding okay when the company is at X Milestone and you expect to raise insert dollar amount what investor is going to want to see at that point in time and knowing that well well well in advance and sometimes that means asking your exist investors hey what would you want to see and you know triangulating with the feedback that you get and also what you think is realistic from your projections but making sure that you clearly understand that in advance because it often will happen that you

know a company will will think oh well I just need to get the product you know done but if you want to raise a $20 million round and you don't have a single customer yet investors are going to say well we want to see that there's some actual willingness to pay for this thing for example um and so just understanding like where you need to get to and planning appropriately so that you have the right timelines the right amount of cash you don't run out um before you get to those Milestones I think is is really important in what you're saying 100% I mean that's that that's the lights on thing right like you you they Ariana has her math your math your job is from evaluation standpoint to back into it like they're

all things are tied together if you raise at 100 today that means the next round's got to be a 200 00 what does 200 in your business look like from a kpi standpoint and if you raise 10 you better use that 10 to get to the 200 right and this is what's dangerous and risky about startups is if you don't then you're then you maybe the lights go off and I think that that's it's it's just you know it's your kpis it's the VC's kpis it's the Milestones checkpoints and you as the as the Entre rur your job is to say you know a lot of this is common like Comm like resource allocation right that's the essence of

it okay I have $10 million I'm burning 600 Grand a month am I going to be good or am I yeah and I would just add one more thing on that which is that you need to understand like sort of what those Milestones are and how to get there in the right amount of time but then you also need to understand like well in s want to see that you can map out where you're going and that you actually hit the things that you say approximately at the time that you say you're going to hit them because I think there's nothing more uh discouraging to an investor than seeing Oh hey we had these like great plans it all sounded good we said we'd be excited to fund the

company at you know X milestones and then you're totally off those Milestones because then the investor is like well how am I supposed to trust any thing that you forecast from here so making sure that you're in a position where you can really um you know set digestible goals and actually hit those at approximately the right time 100% so I wanted to understand more on the board construction uh that you said so like how do you see the difference between board members versus just advisers and like do you actually want to give people to have a w on on on saying I mean advisers are some are people you know who you're G to get like an hour from a

month and you're going to be able to kind of like get some like really good expertise from them and you can kind of ask them for like a connection or two like can you make this intro For Me Maybe um I would say that advisers you know kind of come and go the other kind of adviser is one that would signal something of some kind of legitimacy for the business like we bring in restaurants sometimes as advisers not because we think they're going to um necessarily like help us strategically like in terms of operating Tactical tactically for the business but having them on our roster matters um I mean the board's like your core team like your the board is like like these are folks you're talking if

you're not talking to your board a lot talk to them more not that you have to have lots of structured conversations I mean our Cadence with Blackbird is quarterly board meeting we just fired up a monthly kpi email um and and a lot of texting and a lot of texting a lot of ad hoc stuff but like they're your core team you're not you can't I would say I can't call Ariana up and say like I think we're but I can say like we have a really thorny problem I need I need you to help me think this [Laughter] through if you don't have if those are not the people that you have on your

board you need different board members and by the way you actually could call me and say hey we're and it would be okay because we have that Cadence but what is not okay is having a quarterly board meeting communicating not at all and then coming to the board meeting and announcing oh um because then you're you're not even opening the door for your investors or board members to help you along the way which is quite frankly infuriating because you know we want to help we're obviously incentive aligned um and so I think having that Cadence of communication makes it so that if there is a problem you can nip it in the buttt earlier and you're not just letting it spiral into this gigantic monster that then is is harder to wrap your head around and by the way

also if you're thinking about you know if you ever find yourself in a position where you need an emergency cash infusion from your investor I can tell you for sure that those conversations are going to go a lot better if you've kept them apprised and they've given you advice and you've taken that advice rather than you disappear into a hole you feel a little bit of shame because things aren't as well as you'd like and then you call them up at the 11th hour and you say oh you know oops what do we do now can you please give me money like those conversations are not going to go well so the more you're communicating and the more you're keeping them in the loop about the good the bad you know and everything in between the better those conversations are going to go even if

the problem ends up being substantial yeah so I'll give you here's here's some transparent honest uh recent experience with our board so we uh recently did something that I think in the long run is going to be super high leverage for the business strategically um but it came out of us really kind of like hitting a little bit of a of a road I wouldn't say roadblock but like a serious speed bump with a potential partner and we went through this at our last board meeting and to some extent I had gotten a little too far into the problem solving without bringing the board in and I got that feedback like you know it's cool that you solved this problem and this is a pretty good

solution but like a call three week three weeks ago would have been great um and so I do think like the more you bring your board in and the more you communicate and overc communicate the more they're going to be with you it's sort of like I guess that's in the end what it is like the board will give you what you give them I think um and the more you're bringing them in and the more you're bringing them in CER strategically tactically you're they're not going to do your work like don't get them in the Weeds on like the sales deck necessarily but like building the business the more you bring them in the more that you're going to they're going

to be your core team and by the way I think that applies to the board but it also applies to your investors any folks like that whether or not they're officially on the board yeah qu question on uh you kind of a both Ruth resi and Blackbird we building a two-sided Marketplace between the restaurants and the consumers how much effort uh do you spend on each of those do you focus purely on supply side and building up the restaurants are you trying to get uh consumers to take interest and to kind of bring it to restaurants do do you kind of balance across both or you focused kind of on one or the other more uh well there's a very smart and recent partner who wrote a book on this on two sided marketplaces and uh in that book the thing that resonates more than

anything for me is like in marketplac there's an easy side and a hard side and uh that's not the challenge the challenge is in knowing which one it is which one is which um and so uh for resi the hard side was restaurants because they had they were actually quite risk averse when it come when it came to adopting new reservation software I think we probably think that in this business the restaurants are the easy side it's a super clear value prop it's light it's low lift in terms of implementation so in this business the hard side is the consumer is consumers um I don't know we'll see we'll see if we're right we'll keep we'll watch it closely to make sure that

we're making the right assumptions there but so I think the answer to your question is for us with Blackbird we're focusing on doing things on the consumer side um where we can sort of be confident in product Market fit and understand that we're controlling our own destiny because we know how to grow that side of the business although I think I mean this is kind of the copout answer but like you you have to think about both because like example in the in the early days once you had just launched we were looking at retention numbers and I was like oh you know I think the reason why these aren't yet where we want them is because there's not enough restaurants yet like I want to use Blackbird every night but there were at the time like only a few dozen restaurants and so it still enough right

right but I mean it's a lot more now and it's continuing to grow but at the time especially I was like I I am so incentivized to use this all the time and I just literally cannot get reservation at enough Blackbird restaurants to keep my usage numbers high and so I think you know there's always going to be an interplay between the two totally I think that as a for a consumer application like the dream is that you know um the everyday consumer is like replacing an English word with the name of your company right um obviously that's happened for resi how much of that was like intentional how much is that you like just saw something leaned into it super hard is there like a way that you would think about that you know in blackbird for how to recreate that sort of success I mean

it's intentional in that I want to create big globall lasting Brands like I don't really want to do something if it's not going to exist in 10 years like I don't know you know for me that's I we don't around we for me what's the point if it's just going to like nobody's going to know about it or no everyone's going to forget about it so yeah I mean I think that's part of the mindset you want to build generational things I mean if if you're asking like how to how do you think how does that sort of yeah how does that trickle down into your framework of thinking like for Branding for like um you know thinking about even like how to name the company maybe as an example like I wish I could give you a more satisfying answer to this question because I do think some of

it is I mean for me there's some feel to it you have to have some brands in your mind that are Northstar brands for you like brand not necessarily in your category but it's helpful for me when I think about Blackbird or when I think about resi or eer like it's help for for me to say this is a brand that's kind of where I want to get where I want to go with this this is this is a brand that's doing things in a way that I think is interesting so you know I see you're wearing an a Outdoor Research hat right that's a cool that's a very specific Cool brand and they do things a certain way and um and then

actually a super a brand that I love um and it's an example of it's not exactly the right fit for Blackberry but it's just an example like there's brands that are Brands that's one of them you know if you're like if you're into running and running clubs which apparently everyone in New York is right now like Bandit satisfy like those are Brands like they're doing stuff and you can kind of feel how they're not just building not just like making apparel but they're building Brands they're telling stories they're like giving you a way to think about and feel about their brand so whatever you're doing you I I do think you have to have some comps and some like points of inspiration I've been using EA resi and now Blackboard for a while so thank for all that um you

asked something in the beginning where you were like we're building an economy for restaurants and f as the currency and then you were mentioning that you know to restaurants you talk more about how you save One credit card fees I guess like in that like Vision to like you know longterm versus what's uh achievable now like what where and I also know that you offis skate the uh the blockchain part but like what really resonates with the with the restaurants you're trying to get and also like what is your story uh like like Bandit for runners what is your story for for for me like to to use this the consumer yeah be rewarded for your loyalty like you're rewarded for your loyalty in other categories like when you fly on an

airplane you get points and those points acrw and become valuable when you use your credit card you acrw points those become valuable but being a regular at a restaurant you don't really get rewarded for today like maybe you get access but maybe not and maybe the matrid changes and then you're back at square one so be rewarded for being a regular and what about the U like the longterm Vision rest economy what mov the today I would say that's the hardest part about building this business is like we really know where we really know where we want to get with this thing like the North Star we see it it's awesome it's like the promised land of a restaurant Global Restaurant economy where restaurants

have their own currency and they're can control their own destiny yeah the Tactical stuff is a lot harder and I think we are focused on understanding how to drive value at restaurants day-to-day I mean in the in the on a day-to-day basis a lot of that is like helping them put customers in seats uh you know one thing we've discovered is we talked we had an assumption that we could like really lean into like credit card processing fees and what you're saving with Blackbird but in but I think we've actually kind of learned like that's something we want we need to we're going to grow into because it's just not that much money that they're saving in in in total in in dollar terms so we have

discovered we can be much more impactful day-to-day about putting people in seats and helping them stay open so yeah I mean I think you got it's it's about understanding your customer like it's that comma for like who's your customer what is there what is it what can you do today for that person for that business for that entity you have to do something immediately like they're not going to just be along for the ride just to be along for the ride so it just depends in my time being a Founder I've learned it's very easy to be distracted and one habit I've learned to do is to just wake up every day look at my Northstar metrics and make sure I'm spending my time to impact it I'd be curious if you have like other strategies you've learned over the years and how to stay

focused well it's very handy Ben only thinks about restaurant Tex it's very helpful um the focus of the last 20 years yeah um I guess I I would say I I actually have my own um like to-do list format um which I have sort of like the Tactical things of today and also the things like that I want to do this week I try a lot of times unsuccessfully but I try to be more oriented in terms of my productivity around my calendar versus my inbox um some days at work some days I get distracted by the Inbox and uh I

sort of feel like more than anything else like if you can only move the ball forward on one thing like figure out what that is and make sure you do it like that's you got to move the one ball forward every day like something you've got to finish a little bit ahead on one thing and that will compound you know like that's progress they will compound over time but to be honest with you I'm not the best organized person I'm still figuring that part out that's what I that's how I try to think about it all right well thank you Ben absolutely thank you [Music]