Henry Kirk gives a clear-eyed look at startup life, from the adrenaline of building fast to the less glamorous work of hiring well, surviving cash flow problems, and keeping partners aligned. It is especially good on what AI changes, what it does not, and why credibility still decides whether a young company gets another shot.
A conversation with Henry Kirk | 1h 01m
Henry Kirk approaches startups without theater, and that makes this interview stand out. He has worked inside large companies and built outside them, so he can compare the structure of one world with the improvisation of the other. The startup version is faster and more exposed. You move between product, sales, hiring, delivery, and strategy in the same day, often without much separation between them. That broader frame gives the episode its tone: not anti-startup, not romantic, just very honest about what founder work actually looks like once the slogans wear off.
The AI discussion is particularly useful because it stays grounded in business reality. Henry sees software creation getting faster and cheaper, but he does not confuse faster execution with a lasting edge. Teams still have to validate demand, shape the right experience, earn trust, and explain why their product deserves attention. The same realism carries into hiring. In a world where candidates can lean on language models for polished answers, Henry talks about recorded work sessions and closer observation as ways to understand how someone actually thinks through a problem.
The later sections add the lived experience that many startup conversations skip. Studio Init came out of the 2023 Google layoffs, grew through relationships and visibility, and had to survive the usual operational strain along the way. Henry talks about tough client work, partner alignment, unpaid invoices, and using severance money as early runway. He also makes a strong case for public writing that sounds like a real person instead of a polished growth machine. That combination of tactical detail and plainspoken self-awareness makes the episode useful whether you want to found a company or simply understand how one is kept alive.
The automatically generated captions have been organized by speaker, lightly edited for clarity, and broken into paragraphs for readability. Names and wording may still contain errors.
hi everybody today I talk about startups and just life as an entrepreneur with Henry Kirk Henry has the unique experience of working at large companies working at his own startups and making a jump between them a few times today he's the co-founder of Studio init which he started with a bunch of his colleagues from his time at Google so over the next hour we're going to have a pretty wide ranging conversation uh on a bunch of topics mostly focused around just what it is to be a startup founder what does your day-to-day life look like how do you wear multiple ad and remain focused how do you hire people effectively especially when Candace today are probably just an AI assistant away from having the perfect answer which might
mask how talented they truly are how do you deal effectively with multiple co-founders and a bunch of other topics that we'll be just naturally getting to along the way it's going to be a fun one so let's get started right well Henry it's great to chat with you I've been following your content on LinkedIn for quite some time and so it's just great to get a chance to talk to you in real time about all the things you've been doing and just and dive deeper into all the other topics that we might touch upon during our conversation yeah
absolutely Kupa thank you for having me it's a a pleasure yeah so you know I
like to ask this question of all my guests which is you've been working in tech for a long time what made you decide to start working in Tech what
made me decide to work in Tech that is a a great question um I think I've always been into technology since I was a kid um I was fortunate enough my dad had um a little chain of retail stores and so I was exposed to my first computer there it was like a an 8088 or something like that it was like a five and a you know five and a quarter floppy uh he had a real real there at one point and so he had a full-time database administrator programmer there so when I would hang out there on weekends um I would kind of like look over his shoulder and he introduced me to like GW basic at the time and uh so I just got books at the library and kind
of got hooked so um that was pretty much the start I just was introduced to it and I thought it was super cool oddly enough I was not a gamer a lot of people were like became like very into gaming early on when they were in computers I was more interested in like how they worked and I really liked making software that was uh it was always fun uh I used I had I had way too much fun uh messing around with the uh like little programs at the you know a young age so it was pretty fun what was the
first program you remember creating H
yeah well I I I knew you were GNA ask something like that so I was kind of like a bored kid trying to channel my energy uh in computers and so what I used to love doing was is um I'd write these little like these like scripts that um and I would go to like the computer stores and I would install the scripts on the computer that would say like bad Commander file name or like mess with this like have fake UI on the screen that would put them in there and then you would have like some sales associate run over and they were all beeping and doing all kinds of crazy stuff it was fun it's like old like this is like before Windows was even out it
was just uh and I I used to like doing that so that was pretty much just like annoying people was one of the first programs that I I used to write yeah was
there a pretty good programming language you were really drawn to so I started in
basic uh um and I stuck with that it was what I just kind of was introduced to so I I I would mess around that and then let's see and then um and then basically like then essentially the internet was out so I started dabbling and you know HTML and other things like that was not a programming language but like I started to move more towards like web based stuff and so I was doing um uh um uh basic of the time and then I started uh a little bit of Pearl and I was doing some PHP stuff but what I was um really interested in like uh was kind of like some Java and Java Script really early on I remember getting like the
books and and going through that so I didn't really have a preference but I was just like super interested in learning everything I remember um one of the bigger applications I wrote years and years ago was like serers side JavaScript which is like essentially it exists today it's like like I guess nude and what it was and I thought it was cool it's like a Netscape thing and I remember as like a how old was I then so I was probably it's probably like 1995 maybe um I remember applying to become like a certified you know like Netscape Enterprise developer it was pretty fun it just like cool I just I I loved everything about it and um I used to keep like notebooks with like ideas for
programs and like sketch out things it was just a lot of fun um much different than kids growing up today when they're introduced to computers so you know I I tell my kids like it's well it's like I'm torn now go and say something like oh that was like the good old days of things but there's plenty of really cool things that they're exposed to today that I didn't have you know to be able to um kind of like accelerate their their learning or like dive into something really cool so yeah it's hard to know if it's actually a good or a bad thing because the struggle of having to like know resources and like you know not like websites that you could just go
or YouTube back then that can go and be like how do I do something you kind of have to figure with stuff on your own there's probably like you know bite magazine was a thing I think wired back then had like some interesting things and barn & Noble was the thing you can go to the computer section and find like you know esoteric books on topics and you had to figure it out on your own but beyond that was like that you had to you learned so much through the mistakes you made than you didn't which I feel like you know today's students may not be getting the same same level of depth in
some of these areas that's true um you had to go really deep there was no stack Overflow to save you so it was just getting different books the the hard part was that things changed so much that the the books were behind or you would like have to really stay on top of it um where these days I mean obviously books are out of date today um but there was like you said there was no YouTube there was no internet there was no like courses to get or anything like that so you're really on your own um I feel like the creativity is still there like from back then to now when you when you talk to people it's just like their mechanism for kind of like how they how they kind
of dive in like I I used to um I think yeah
I I think I'm as of like the last year I'm just as excited now about where Computing is going um as I was as a kid and the things that you can do with the um like LS and some other technologies that are out there it's just like really allows you to accelerate development because I I'm the type of like I call myself like a product engineer I like to um build things and try to you know solve problems with that I don't necessarily care what the code looks like um I'm sure people be up for that but it's I think the output the outcome is more important and so how you get there is you know um uh I don't really care so I'll try different things as
long as I can have the outcome and do that so the last year has been pretty
exciting oh absolutely I think every generation of developers probably go through the space where they're like you know the stuff I learned back then may not be relevant anymore but they're more interesting things to work on because I know like you said you started off with like you know basic you know for me it was actually JavaScript and action script you know the early versions for the flash world now someone let's say we were having this conversation let's say 20 years ago 25 years ago someone who learned like assembly and machine code might be like ah you know I want I want why can't these people like learn machine code you know that's where that's where the real magic is at and because they didn't learn it they're
missing out on some of these things and right now with all the r have like AI assistance where you have an idea and you get code that kind of comes out of it you don't think anymore about you know what version of JavaScript am I using or my node server probably all those little details you probably you know as tribal knowledge you've been collecting over the years no longer need it and you're just like focusing on that idea and so I'm always curious to figure out like you know 20 years from now what will be that generation's version where they look back at llm and go like wow that's such a backward way of building applications or will apps as they even think about will they even exist in that
form you know when we think about that what the future looks like yeah that's
uhh you're right it's it's right it's be like oh what version are you using I remember I I've been in iPhone developer for since the beginning and I remember you know the conversation like oh what version of you know iPhone Os or iOS are you using or something like that and and now it's just like even if was me I've been for the beginning I can't even remember I used to be able to know all of the different apis and the features across the different versions and what the capabilities were across all the phones way too challenging now it's just too broad and too deep and it's like it doesn't really matter either uh anymore it used to be very important back then but yeah so yeah that's completely gone
it's now just oh I'm looking to build this I'm like okay cool it's no longer like oh you really got to consider you know XYZ because of this and here's a workaround for that it's just things of acceler so much um yeah and you know maybe it's just my bias speaking here but I also felt like things were just easier back then also like there's something nice about having a text file you write some HTML in it use an FTP client send it off like you know use type your username and password and just like send it over to like you know a server you pay like you know $4 or $5 a month for and everything just worked immediately whereas I think most people
today would probably be like what is an FTP server you know like where where AWS fit in you're like aw doesn't have to fit into that you can actually deploy websites without needing any of these complexities there and so sometimes I feel like the the abstracts are a good thing it helps you focus on more bigger problems you know like if you're an FTP server you got a million people visiting it yeah probably there's a very good chance that your sit is going to fall over unless you have a CDN which back then was like maybe aami was like the one but it was for big clients if you were individual you didn't really have access to any of that and so you're like there new problems that have been
created that are great to solve in the future but things in the past didn't have the same things but you know pros and cons of it but I do always wonder would the world have been better had we kept like some of those little details still in some introductory material so people are like not completely missing out on what it took to get to where you are today that's a good point yeah everyone's imp patient these days you know um one of the thing you know clients we work with are we we work with startups and so we have to get stuff done fast I mean I I can appreciate what you're saying where it's like years ago many many years ago we were valued if we
said it took two weeks it took two weeks if you say I think I'll be done in two weeks they're like can you get it done in a week and a half because there's some guy that said that it you know could go faster this way or something like that so yeah the whole industry has changed um and it's uh it's it's challenging the compete because there's always there's there is an endless amount of ways to do what we do we're no longer like very special you know I
agreed I mean it's always this tension between quality versus quantity and you see this across so many other Industries you know I think that you often see like this as a you know I feel like software development was like somewhere in the middle of it but you see you see the early signs of it in other Industries like I think with graphic design you saw that when like Fiverr and some of these Services came up where you know you put like a you know you say like I want a logo I'm going to pay you $5 someone in a part of the world where $5 is actually a larger amount of money than what is in America they created something and you're like you know I don't know enough
to be like is it a great quality logo or a good quality logo but it's good enough for me and I'm going to start using using it and we saw the floor on the pricing for like lot these graphic design agencies and companies start dropping rapidly you know it's like okay you know the services I used to provide that where like you know I used to think about the craft the the art of how do I make a pitch how do I do all these things now it's like you know you just have one email conversation 10 20 minutes later you get like options very very quickly and and that audience now is now struggling with AI is able to generate visuals and things very very
quickly as well we saw this with content Creation in general with like Tech editing news articles and things like that where people used to spend a lot of time like actually writing detailed pieces now it's really a Quant quantitive thing you know like you how many articles can you write in a given day knowing that one of them might go viral the other 90 might not but unless you write all of them you won't know which one's going to work because your competitors are doing exactly that much using machine learning or using you know like crowdsource Technologies and so on and so you're like you know there's a lot of it is changing I think software development is starting to hit that phase as well where
the the art of The Craft and things that you know have prided yourself on like back then it's still valuable but maybe not as much for certain set of clients who want something to solve their immediate problem as quickly as possible whether it is done by a human being or by some computer or something like that they're okay with it and the and the price for those things can you know vary wildely and the cheaper things are often times we we gravitate towards yeah it's true and it sounds like you know you've been around as long as I have and way back when the computers were much slower obvious they you know not as efficient as today so poor programming practices would really like like come out and
stare at you these days the machines are so fast they can mask a lot of the inefficiencies um so you don't have to really be right performing code anymore uh it'll be much harder to notice so um I think that's like been a big change in this like you're right on the on the point of just you know where do we kind of fit in and I I think it's the um uh providing like the the guidance and the experience you know that that folks NE not coming into the industry today don't necessarily have it's like how do you make the right decisions how do you make the the conversation I come up with a lot of like working with startups it's like um I want to be able
to scale to 2 million users well how many do you have today we don't have any okay so let's build out the first thousand users infrastructure because I guarantee you you're going to Pivot along the way so if we spend all the time on building for the million users you're going to waste money and you're going to learns and you're going to change it anyway so you know I see startups that will do the million route because that's what they think is the right thing to do and then I'll see the startups that build the fragile stuff because someone made some poor decisions along the way and then they then they have to like go back and fix it I'm of the opinion that like you need to
balance it so if your system goes down because you're flooded with users is probably a good thing you'll figure it out you get it back up but the the key is is is knowing how to make the right decisions along the way to build the products to get it out there because at the end of the day you're building for users and if users don't have the product to work with then you know there is no business there and you don't have anything so it's like speed is very important um and so I think like that's where kind of like engineering is kind of gotten to today it's that how F and and it's speed is important for being competitive too these days is like there are developers
all around the world and they they can build things very quickly nowadays so it's like if you have an idea I see this a lot too it's like I I talked to so many startup Founders it's like there's a lot of patterns that I see that was one of them the second one that I I I think is very interesting is that they always say like I have like such a great a billion doll idea and they'll tell me what it's my I'm sorry but you know you're the fifth person to tell me this in the last month so it's like I was like well one way that you can win is to get it out there faster than someone else and number two it
could be make it a better experience or Market it better you know so there's a lot these different ways you can compete but it's like knowing how to do that and what knobs to turn along the way so I feel like that all kind of like makes it very exciting these days to kind of I mean you know it's like the first step is like will people even care you're building it and how quickly can you validate that there's interest or desire or need for what you're doing and once you have that then you get to the problem that you're mentioning it could be a good problem to have if there's like a million people using your website and so on but taking a lot of time to
build for this utopian future that you may not even get to because people don't find any interest in it and the other one also is that you have an idea today by the time you get your MVP out let's say 6 months from now is that idea still even valid or is it even worth it because the speed at which some of these things are moving in is one where you know if I would if I would to make a bet on like when can we get really high quality video by just using text prompts I would have been off by like years you know my guess was like you know when I saw the first version like of Will Smith eating spaghetti I'm like okay this is
awful we're not going to get real time video that's really good things for at least you know four or five years six months later you know there's like you know a much better version of it and then another six months later you know you're seeing like this is like you know using like videos and and actually like you know professional commercial like advertisements being recorded entirely generated through Ai and you're like okay that was that was something if I if I was like working on the perfect solution to get the perfect processing pipeline for my video and all these things I would be lost at this point because I'm like nope I'm not I'm
already out of the game yeah I I don't even I can't even like to me it's gone so fast it's it's it's like a blink of an eye I I mean I remember when I I first saw that Will Smith and it's funny kind of funny that Will Smith is The Benchmark because you're not the first person to bring that up uh it's like uh that is it is really crazy um how how fast things have come uh it's like and you know what actually you know what I think is kind of interesting that I haven't seen yet is no one's really gotten like that the whole like AI detection thing done very well and so uh not that like it's there are no startups
that I've come across that is anyone is working on anything to try to like protect it because the next big wave that we're going to have is um uh I think of like all this fake stuff that's coming out there and it's not necessarily for like the propagandist and like the you know the cons government conspiracy theories I think that these you know engagement Seekers on social media are going to use these things to like help prop up their their reach and exposure and so I'm going to see this now with the uh the um the uh um deep seek stuff that just came out uh you know and there's folks jumping on it saying and it's going to replace this and that and and um showing screenshots
and videos of stuff of all of it working and some of it is factual and some is not and they're and they're doing it to because people are looking it up and and trying to get engagement of it so I have it'd be really cool to see like startups that are trying to look to like build stuff to at least say oh hey this is generated by AI it could be code it could be um a video it could be an image or anything just to be able to like validate that it's not real um yeah just like C like tying that a little bit together one of the challenges that I have you know in like hiring for our teams is so many Engineers are relying
upon llms to do a lot of their work that I have seen um uh cheating when we asked them not to use L and other things that makes it very hard to gauge their ability to do the work with without that crutch and so like that the detection software that we use when they're doing their like coding exams catches some of it and other times we have to watch the video to go see the copy and paste and how fast they do stuff because I know how long it should take a person doing it so like that's where like I'm I'm going with this is like nobody has built anything that's really good to just kind of say like oh hey this is you know uh
created by an L or something like that because I think that is like important to be able to at least like Mark it you know Watermark or something like that to be able to say that but could be wrong
yeah it's almost like you know there's this hive mind that controls everybody this point because whatever you might be doing as like individual thinking or creative thought you're like you know I'm going to Outsource that to an llm and so all you're doing is basically just this warm body that translates what the llm tells you to put and then you put it onto your screen and put like an interview or like an essay or something like that you're not really any more like exercising those muscles again to kind of come up with these things on your own right that's interesting one though so for these interviews then how do you know do you actually have them record the screen at the same time so that way you can you know see what
they're seeing at the as well or how how does it work because I never actually thought about the you know I'm a product manager so most of my interviews are conversations like what you and I are are having right now and so I don't do any coding interviews but how do you how
does it work yeah I can see we've tried a bunch of different things um we uh we've used a bunch of without giving away like how how all the secrets so folks that might be listening like um how do I how do I know that they're they're cheating so there's a piece of software that we use for interviews and it has a lot of like triggers in there where it just Flags it for us to review it it doesn't go and say it's definitive one way or another um we ask folks to do it themselves it's very very important um why because we want I know that LLS don't write great code right and even if you're the best prompter in the world you still have to
know what's happening because it's it confuses itself they lack context these days you know the context windows are not very large on some of these tools and so you need to be able to know what's going on so we want people to demonstrate that they have the core skills so how do we do that so it uh Records their their screen it's an ID in the browser and it records the whole session and then it Flags things along the way and we just watch it so a lot of folks don't realize it and even know it says that hey we're recording your screen you know don't do this don't do that and we get it you can see by how fast they do it so if they do a you know
a coding challenge in five minutes I know there was something wrong um you see a lot of copy and paste um we see during live interviews so we'll see people that did really well on the pre-screening section where they're asked to like code something get into a oneon-one like on a a video chat with someone and they can't actually perform well so we know that obviously something was there but I want to say that at of the we've interviewed probably um I want to say like, 1500 people over the last two years for our engineering roles that we had open and I want to say that more than 50% of them have cheated cheated by not following the guidelines that they gave uh for us
and assessing folks and so we've tried to make it challenging we've tried to make it interesting that to kind of like pull people out um and and like find the real creative talent in there and then bring them onto our team but it's been very hard so you know I we're about to hire another round now and I think that we're going to have to revisit kind of like how we're doing it as well because we do have to enable these like AI Tools in a way and I think that they're in a State now where it's okay that they use them we've always said that it's okay to use them but I think that like you need to understand how they work to be able to
be effective with them and I think that like they will be the future and so we have to so we have to find people that have like the core skills that still can use it but also at the same time understand how to use the ls and don't completely rely on them it's like a partner a partnership it's kind of hard to kind of hard to explain but uh it's like we're trying to figure out how to balance that and that's something that we're trying to come up with yeah touch
upon the common question on all over which is like are interviews in Tech broken in general they've always had this conversation for forever but now with like coding questions that can easily be answered by an llm you know have you do you where do you stand on that do you still think that you know asking coding questions is effective way of gauging someone's abilities or are there other things you think would be a
better indicator of ability yeah everyone pra there's all of these like YouTube videos on like how to crack the interviews and things like that and so you can usually tell when they're super prepared for that um and uh um I want someone that is going to be able to solve problems and be creative with it I don't care if they solve the elite coding problem in you know 30 minutes or 20 minutes what I want to do is I want to see how they solve the problem so uh it's like it's how they think that's more important so yeah we do the traditional interview and I was like Google for eight years and Amazon for two prior to that so I have 10 years of
these you know styles of interviews to try to find really smart people at the end of the day it's like how do you think and how and then also like for the type of work we do is like what kind of drive you have and like how ambitious are you at the end of the day and like there are certain things that can be taught and certain things that are just kind of like how people are you know raised or um they just have it in them or not and we're trying to find those sorts of things so yes I give the coding challenges and I'll pay close attention to how they do it I'll then we'll then um we have multiple steps in our
interviews for whether it be design or engineering or product or anything like that and after the initial like coding screening to just see that like where they think we'll then bring them in like a virtual or an on-site interview and then we'll just ask them questions to probe how they think that's all it is it's like there could be no answer but we just want to see how they approach it and if they're kind of if they break down along the way so do
you see the the tendency to like be you know unable to answer these questions properly without using llm to be more of something that a lot of Junior developers who are just like coming to the industry recently doing or do you see this also with experienced developers who've been doing this for a very long time yet they've lost the ability to write code effectively essentially or they've just been you know working in different roles than what they actually were supposed to be working which happens in big Tech all the time you'll be you know working on supposed supposed to be working on something else but it reor happens you're working on something completely different and now you're interviewing for something that was probably supposed to be experienced in but you're not do
you see any patterns in that because you know I guess I put it differently at least whenever I you know I I like R like you know subcontract various parts of my website and hoby things other people and I I didn't to go for like the most experienced people I'm like I've known them for like 10 years 15 years 20 years because I know exactly that they know these skills inside and out whereas I'm always like a little bit wary of like you know like spinning the dice and going with like someone who's more new because I just cannot know like is it work truly theirs or did they use all these newer things to create things that definitely gets past my filter which is
by far not the most tuned there's a lot
to it um I think first off the job market is horrible for engineering right now and so I think to be successful you have to apply for dozens of jobs which makes people cut Corners to try to get ahead so I think that's part of it um uh you are not only is your resume made or tweaked by an L you are now trying to get through the many coding challenges or or pre-work that's needed to be done before that so how else do you get through dozens of them you know to be successful it's too competitive right now um across the board um when uh when I used to do a lot of interviews um that you bring up like folks that were kind
of like out of their game and coming back into it I'd see a lot of folks that were engineering managers switch back to be ic's and they would struggle the most but at the end of the day it's preparation so it's like if you go into these interviews really well prepared you will do you will do super well if you are not um then you know that would be a problem like I used to do a lot of coaching for folks going into interviews um over while I was at like Google and Amazon and it's like I'd always tell them this is your one shot be super prepared here are the things to practice with practice in the environment that you're in code on a whiteboard code on a
piece of paper because you got to get used to like spacing and writing being clear and thinking through it and so it's like those are all of the things that kind of made you successful if you had those core skills that's where people would usually break down they're just they just kind of like jump in unprepared these days I think if the market wasn't so competitive you would you probably wouldn't see so many people leaning on the loms um to get through these interviews that's like one area uh that I I feel pretty strongly with that it it's just the the circumstances but at the same time there's been such a push for people to enter in engineering to get these big salaries that there are
people that probably pick the career when that's maybe I don't know if they like really love it and they're just trying to stay in it so I can see those folks kind of like getting lost and and struggling to to find the right fit and so we'll then probably cut Corners potentially to kind of like find those roles you know like um when I Google used to only hire gener generalists for a bunch of years and then he started changing it and basically definition of a journalist was I can put you in front of anything and you'll figure it out and you're you're Cod diagnostic like you don't have a preference you don't have a certain stack you're willing to learn anything and I think that's really important
especially today so you have a lot of folks that are very um fix fixed on like one type of you know Tex stack or another and um there's good and bad about that so I happen to think that like you need to have a very broad set of skills and that also will make you make better decisions like you you talk about like folks that you know are are newer and less experiences like until you've done the whole end to end thing and and felt the pain of all the different nuances like you may not realize what it is to like build the products and like how to make the right decisions and then there's also a lot of solo folks out there and so I think that they
don't they and I was solo for a part in my career too and until you really have to work in a team with other Engineers to like a bounce ideas off of people and have to challeng like and basically defend your decisions and why you are choosing things like you don't have that outlet to improve yourself right and so then you become dependent upon other things so I think there's all these like different circumstances that kind of like make folks drawn to this and it could be temporary it could be permanent I'm not
sure yeah no it'll be inter to see how it all evolves it's also go back to the question on you know will there be an AI system that can actively detect accurately that someone is you know it is genuine content or not genuine or someone's actual ideas or not and that could all feed into it but as you've seen historically though no matter how good that the technology gets for detecting you know Bad actors The Bad actors also evolve to figure out ways of of essentially bypassing those detection logic as well now we can talk about this indust this is like a fascinating topic on its own but I want to get to the present a bit you know studio in it like tell me more about your startup and how
you got there and all the things you're
working on sure um so uh we're uh we've been around for just about two years um we were born out of the uh Google layoffs in January of 2023 uh my entire org pretty much was cut and uh when the layoffs happened I was a manager at the time and I noticed that it was going to be really hard for me as a manager to get a job so a lot of us wanted to kind of like continue to work together I'm kind of like shortcutting and compressing it down but like over a couple week period I decided that I didn't want to go back to the corporate world for a variety of reasons and so um a bunch of us wanted to keep working together and think of a good
startup idea so I said like hey you know we were kind of like a startup team within Google why don't we try and see if we could do this outside of Google um inside of Google we would kind of like do zero to one projects we would do our own like research and build stuff and so I said you know hey we're really good at this like this space so let me do a post on LinkedIn I have like I think I had like 1,600 connections at the time like maybe someone can like connect with with something so I wrote a post kind of announcing what we were doing and seeing if I can get a couple meetings and it went ridiculously viral and so that kind
of gave us the we were fortunate to have like a little like propping up and get ourselves going got some projects out of that and that um gave us kind of the we had a goal of getting it done by the time uh our um kind of like uh sance kicked in and so and also like not everyone's family was kind of on board with us playing business so we had like a cut off and so then uh you know we proved that it was a viable concept at least and so we kept did that and continued to grow it and so what do we do we work we do like product design engineering and go to market for all in the zero to one space so we work with
early stage startups and we kind of help them kind of take their like grandiose vision and turn it into something very concrete that would be valuable to users and we try to back that up with research and get that out the door for them so they can kind of either find product Market fit or um raise additional funds or whatever they need to do whatever their goals are so we've worked on with a lot of um we work I actually just looked this up today we worked on 34 projects in the last two years which is kind of cool um and so uh we're still still hanging in there had some ups and we've had a lot of ups and downs along the way uh a couple clients didn't pay
us uh and um couple startups didn't make it some of them did pretty well um and uh but at the end of the day we like the process we like the people that we work with and uh we're you know I do not want to go back to the corporate world so every day I wake up I make sure that I have the mentality that my back is against the wall so I can keep going so in your history you've
jumped between entrepreneurship in the corporate world a few times yes and so you know what makes you you know feel like this is it you know you're not going to make that switch back into the corporate world again
well the reason I jumped into the corporate world is because all of the startups except one maybe two that I had prior to that I was always very entrepreneurial like failed and I couldn't figure out why and so I was like you know these other these big companies probably knew a thing or two about you know scaling and growing businesses so I was like I I go join one of them so I had an opportunity to join Amazon and uh I said all right done you know took it and uh that was like history and I I I really enjoyed working at Google I probably would have stayed there I had I was always planning on leaving to do something of like what I'm doing now um so it's just a little early
um but the but I filled in the gaps I learned all the things that I uh it was it was a lot of it was me my leadership style how I kind of like worked with teams it was um you know my decision-making I learned how to make better decisions I learned how to work better with people also my technical skills grew over the years um I understood more about you know like what is you know user growth and what is what what did how do you nudge users to use the product how do you do research I learned everything that like I was just trying to figure it out back then and so why do I think I'm not going back to corporate world
because I feel like I've filled in enough of the gaps that I can figure out the rest the uh rest today and um this is what I wanted to be doing from the beginning so no I think that's great you
know when you talked about earlier about how you want to validate an idea and then slowly grow it into something bigger and see how it goes with many startups and many products you often have time you often are like okay you know I'm going to figure out what the problem is I'm going to experiment try things out and and so on in this case you had a very accelerated time window you know it's like you like okay we get a startup that's going to basically prove itself viable you know within this narrow period of time so in some ways the process came first and then was kind of like okay now let's what is what do we focus on how do you navigate that because it did seem like from where
you're describing your history you were passionate about certain things and certain you know ideas and things want to pursue whereas this might have been a little bit different it's like okay we need to get a start up now the clients might dictate what we end up focusing on
yeah that well yeah um that does happen at times but the way so we're we're a little bit different so first off I love the I love the process I love building things and I and I love figuring out the idea and executing on things like that is but is great and so while I was you know at Google I was having a blast because every 6 months or so we were doing different things and so I I felt that I was able to be creative and so in this business I'm able to be creative and things don't you know we're not spending years on the same product to get bored and so um we the types of startups that we work with are we don't
just kind of like take a a list like a we don't take a list of things and then say okay we're going to build this for you we really with you so if you said you know if you were like hey Henry you know I I want to build this thing here is the PRD I'm going to like do you really need this I'm going to tear apart your PRD I'm going to like challenge your assumptions all the stuff that you either appreciate or you don't and we're going to try to help you get to a better place it could be that your PRD is really well thought of on researched and I'm just challenging because I like doing that or it's maybe you'll find
things that you didn't think of and then we'll get to a better spot I like that part of things and so when we're working with startups of whether we you know it's a good fit we're doing that early dance um those that don't appreciate the how our style for like how we like the partner they tend to like go elsewhere you know if they're looking to like completely just dictate end to end so folks that kind of like appreciate that partnership we we'll tend to work with um and so it's not always like my way or the highway it's like a collaboration it's like um I guess said before you know it's like some of the startups that we have like they be like yeah we we're going to we
need to handle a million users I'm like okay cool show me your growth plan of how you're going to get to a million users like well in five years okay five years a lot of things can change so maybe we should just start with this so um yeah so we we tend we've been very fortunate we've worked with really great people and we haven't had any of those issues uh like personality differences between the startups that we work with where anything's gone sour do you have any kind of preferences
for types of projects you like to personally work on
uh has to be challenging we don't want to just do websites so we gravitate towards ridiculously hard problems and I don't know whether that's good or bad uh one of the most challenging projects we had in the recent time was so there was a EX Amazon robotics um uh founder uh started this um I call it like robotics coffee drive up through company it's called ping ping through.com they're super great founders and I had met them uh through Linkedin or something like that and we had a conversation this meeting um I think it was anyway so we had a conversation and he was saying oh yeah you know we're going to build this uh system uh and what the uh their premise is that you know you get super
hot coffee from the robot like when you drive up it like makes it on site instead of wearing like Starbucks it's going to have like it's sitting on the counter when you order ahe so he was explaining kind of like their initial approach to building the software to power the the system and I said you know I don't think it's going to work I think this is a harder problem then you realize I was like you know I have some experience with that I'd love to work with you on it and then we went back and forth and so we were end up building it and we ended up building this presence detection system so you order the coffee at your house you're driving up there
and at some point we detect that you're nearby through one of the algorithms we wrote and then it the robot well it's now powered by humans but eventually be robots will start preparing your coffee and then it knows when you drive up it knows the order are the people in the line and then it and then there's you don't see the people they're just hidden inside and so at the system says put so and so's coffee in the window push the button and then it the window opens up and it goes and it's just magically your order is there and then it's like I've seen the videos of the customers reactions when they drive up and all of a sudden their order is there and they
had no idea like it's completely magical um and so that has been one of the more challenging things like we had issues with you know a couple times I think they ran over one of the uh beacons that we had set up to try to detect like the presence like that so we had to learn how to harden that a little bit that was fun um we went through multiple iterations of the software trying to get it to work because different cars would have like different signals um and like different thicknesses of like the glass I'm not like an expert in that space my partner is um but we had um uh built this incredible system that I don't think anyone really has done it was truly
magical and that was so we gravitate towards these like hard problems that was a lot of fun well that's very cool
because you know whenever I always feel like at least in my mind whenever you cross from the software realm into the real world with physical things whole different ball game whole different things and my lack of experience in that area often means I miss obvious things that would I would catch B St I'm like oh yeah like for example you mentioned like someone ran over the beacon I would have like probably not thought about that on day one I was like oh yeah someone could run over the beacon or you know weather could be really bad or like you know a bunch of different things could be playing a role here so how much did you learn and up discovering during the building of the early versions of it
where you're like yeah yeah everything
it they it every day it was like something different the the list of like oh yeah forgot about that um you know it's uh it was a it was it was completely endless and we finally got it to a really good spot and now um they've raised another round of money uh because it's a um I think they have a really great idea and so they're going to go far and so they're coming back and we're going to try to like improve it and make it even better but it's just like it was I knew it was a hard problem going in but I had no idea um how just how hard it would be cuz there was there there was no books on it how to do this
there's no like oh you just want to do cuz it's like you can't just do geolocation because it's not accurate enough all the phones are different and what I the the thing that kind of got me the most was the um the the different types of cars and how they're built will will will read signals much differently and I didn't really I didn't really truly understand that I wasn't this very naively um because when we had did s similar t of like signal processing early in my career Google there was no one there was just people walking around when we were trying to do stuff and some of the prototypes we were building so uh I was like oh okay this really does make a difference so how do
you solve for that you know it's like it it got very it was very challenging um but I uh hopefully I'm answering your question I think I'm rambling no no you
are because you know I work you know both at Google as well as like at my side projects I work with like agencies and like things always like fascinated with like how they're able to bring in the talent and solve some of these really hard problems so in your case do you have like people on your you know direct team that are like experts at like you know navigating hardware and software or do you have your own setup your own consultant clients and so on that you off often work in partnership
with not part of your company yeah we don't we don't actually contract out anything it's all done local we don't offshore we don't near sure any any of the work it's all us so if we can't do it we'll pass on the project or um if you know if we have an opportunity to grow off of that we will I was very fortunate that you know one of my partners uh you know had did his PhD and um kind of like internet of things which included signal processing and things like that so we were able to have some very um nerdy conversations early on of like how to design the overall system that you know even challenged some of the hardware manufacturers uh assumptions when we
were working with them which was pretty funny so we we were we were lucky there but it was also something that I knew we can solve because I had prototyped a bunch of similar thing like I was very interested in that like I just magical experience is what I've always kind of worked like loved to work on so whether it's delighting someone through like an app that does something cool or an outcome of having some sort of like you know Bridging the the hardware to the software I've always loved doing that sort of stuff so um this was perfect so even if I wasn't familiar with it I would have figured it out um you know went to the good old whatever the Barnes & Noble of these days the library or
something and gotten books on it if I had to yeah yeah you know I think like
Amazon had their own bookstores for a bit but I think I've seen a lot of them not be there anymore in the mall so yeah I don't know where people go nowadays yeah I don't know because I would have had to go to a library or something like that yeah yeah haven't been in a library in years as well in terms of it yeah but you know when you started off you had a you know in general let take back up a bit starting a company is hard starting a company with a single co-founder is hard it's you know when you started you had a lot of co-founders how were you able to navigate you know who does what where's the you know when is the
tiebreaking decision need to be made how how did all that na how did that work
out yeah um first off having partners is hard um it's like getting married to more than one person um so you all have to get along I was fortunate that I'd worked with all these folks for many many years so we kind of knew that everyone's quirks except the the thing that changed over time was everyone's tolerance for handling the craziness of a startup the ups and downs the you know the will we uh you know make payroll next month or have you know earned some money or you know will we finish this project on time will we do this will we get our next project so that is what really caused most of the kind of bumps along the way you know and we also had
some challenging clients like I said a couple of them didn't pay us in one particular was rather large and so we worked for months and months and months and they never paid us so um you know we had fronted a lot of it um we put our severances to kind of seed the business and that evaporated pretty quickly so you know so it was just challenging so how do you you know how do I navigate the partners is you know you need to know you need to set the expectations ahead of time and agree who does what everyone had their skill set since we built a team together so we already knew what everyone was good at and so we just kind of did her thing and no one ever
stepped on someone else's toes um but uh at the end of the day it was just the the life of a startup that kind of you know um uh had some of the partners kind of decide to move on and go do something else um I'm still crazy and so I'm still doing it you know where I I don't think we're we're still a startup and we're not you know we're on our way we're not completely there um but you know I've been I I don't know I just I'm the type of guy like once I go into it like I'm not going to stop I'm going to figure it out I'm very uh stubborn in that way so I'm still hanging in there but like my you
know my advice is to anyone else is like know who you're building a partnership with you may think you know people but trust me once money gets involved things change very very quickly so yeah and I
think like itone like various people's tolerance for risk and the and just navigating the unknown is often very difficult as well because I I think you mentioned you worked with a lot of them at Google itself which is a a large company and there are a lot of processes in place where what you might think is considered chaos within a large company is actually not considered chaos at all in a startup where there is no there is no box basically where you have the boundary where like the worst thing that could happen is a b and c and a startup that is no container you know you can things can go in any direction you know extremely high or extremely low and there's no basically it's not seat belts
you know in many ways and you often find that that individuals who may think of as very risk tolerant are not risk tolerant at all because you know what their basis of measuring tolerance does not apply in startup world that's true
yeah it's you have the ability to tolerate risk is really what makes or breaks your ability to hang in there now you can join a startup early on when some of those kind of like things are figured out and be very successful and there are plenty of people that I know that that purposely look for startups that are you know at that stage but the very early on it's not for everyone it's like it's super stressful but for some reason I don't know I like that call me
crazy I mean they always say like you know certain personalities tend to be you know tend to thrive in these kind of environments you know the conviction of your belief that there is going to be a destination I will get to I think that is a big motivator for many people to be able to you know do well in startups and knowing that yes there might be chaos and hardships along the way but I'm still laser focused on the destination and I think that's where I think you know being a founder of that mindset which you clearly seem to have plays a big role in keeping things still moving
forward yeah I mean there's you learn a lot you know when I had um one of the you know reasons that I feel like I was able to start my career at Amazon was because I had all the startup experience during the interview it's like you know a lot of the folks that I were working with um I had started on the iOS team there and you know they didn't encounter the things that I had and so I thought that made me unique there so maybe that helped me get the job it's because I had been through all because I was responsible for so much on my own and and having to like start up and fail so if you like the if you can hang on hang
on long enough there are plenty of like opportunities to learn and then you Embrace those learnings like I make mistakes all the time but I look forward to those mistakes as long as they're not super bad um to so like oh okay cool then I'm not going to do that again and that's going to make me that much better in the you know in the future so it's I don't know I just love the I love the chase I love the ride yeah and with
starts as well you know you mentioned like you know you kind of look at like what are the areas of expertise that each person will focus on but it's also very fluid as well because you had wear many hats you know you might be doing marketing one day you might be doing like core development one day you might be like you know negotiating you know payroll or like business deals and so on and and those skills are ones that are hugely invaluable so like you mentioned your startup experience has helped you join Amazon and do some of these things is that I always find that too many people try to conform when they go to large companies like how can I do exactly what everyone else is doing so I
I fit in but I always find the more successful ones are the ones who have this like variety of experiences but they can be like you know what why are we doing it that way doesn't make any sense let's actually do it differently and you're saying that not because you're just trying to be difficult it's your diversity of experiences you've had doing these kind of startups and things like that which you know for someone with your experience at that time would have put you far ahead of someone who's probably been inside the corporate environment at Amazon for example many years and never had the opportunity to think differently about how things are done so it's almost an advantage that
able to have that absolutely I mean I think it's like the real world experience it's you know you're really in a bubble in these companies uh you mentioned that before and so I think having a broad set of experience you know is important like uh you know a lot of folks will ask me hey you know give me some career advice and I'll usually say like try to join a startup or something like that for the first couple years because you'll learn more then enter big Tech or something like that if you go into certain big tech companies too early you end up with these like bad behaviors that don't mesh well in the real world you know um or you learn things that are completely not
applicable like it's uh there there were certainly systems like Google that I worked on that I mean how many companies in the in the world can have to deal with a billion users so it's like you're never it's not valuable to you outside of it so if you spend your early career there it's it's not really going to help you may help you understand like how to scale things but it's it's not useful so I'll usually say hey go go have fun on your own go do something like that for a few years then go kind of like like I did you know fix your mistakes by going to bigger companies to try to learn how to like round yourself out and um fill in the
gaps yeah that is so true now speaking
of career advice you also have a podcast a leadership that podcast I watched a few episodes just get a real feel for like you know are you AI generated are you real you know like it's hard to tell you know like for all we know like now I could not be a real person also I could just be an a avatar that has like pre-recorded audio samples that's creating all this but so how you know yeah so how how do you balance your time between it because you know you mentioned at the very beginning that you know having a good idea is a part of it how you Market it is a big part of it as well and I think you're very effective at that marketing piece because like all
your posts that you you know you know are compelling I I SC through a lot of LinkedIn posts in a difficult day but when I see yours I'm like I'm actually going to read this because this actually seems very interesting so you get the the hook properly figured out and you have and then of course you bounce it out with like you know your podcast we also going into more detail on some of these things and I'm like you know there's a there's a marketing capability that you're having that I think sets you
apart oh thanks I appreciate it well I consider myself a little extroverted like I'm not your typical introverted engineer um and so I like talking to people and being being out there and I recognized that when uh look I had when I made this first post on LinkedIn I did a little bit of reading to try to figure out like how to write a post on LinkedIn that you know could could be useful but I'm not a social media guy I never went viral nothing like that but when I did go viral I then kind of figured out what I did right um and I knew that I had to keep up the kind of writing and and um communicating and I've always been a
very direct person so I'd rather kind of tell it how it is I didn't want to come across or or even go down the route of like these fake gurus everywhere where it's like you have one hit wonder and then you're selling a course for $49 to teach people how to kind of get to where they are it's like I have had I've had successes and failures and there are things that like I can tell you about the failures that would would blow your mind right um and I try to be honest about them and explain you know what creating a startup or just a business is really about and so I think it's resonated with folks um so I just you know my style is just to be legitimate
and try to like share things that I think are important and be like be real and not like I have no agenda like I don't um I don't at the end of the post say hey if you like this go subscribe to my newsletter I or please follow me or anything it's just like I share and if people choose to follow me or or read what I have great um you know I started a podcast because I think one of the really one of the most valuable things that I did throughout my career when I was a leader was have a a coach and so I wanted to um kind of like show folks that what coaching was all about so I joined up with my partner uh with my
coach Jonathan arenson to do the podcast we haven't done it in a while cuz I've been a little busy but like he actually was ironically for this year wanted to start it up again cuz uh um it turns out that like we've had some Evergreen content over the last year so where we were like do we were like posting episodes and no one was watching them all of a sudden we have like you know hundreds of more subscribers and other things so uh we're going to try it again but like why did I do it in the beginning is like I again it's just was part of the whole overall is I just wanted to share things and there were a lot of people that reached out um when
uh I had kind of announced our our what we were doing and they saw it as you know um I was my goal was to flip the layoff into something positive everybody on there was like oh I'm laid off it's the end of the world you know I'll never recover and I was just like okay I'm going to turn this into a good thing where I'm going to look back in a couple years and say you know thanks which pretty much I did a couple weeks ago um and um so that was that was the benefit and so a lot of people reached out saying like how do you do it how do you you know how do you stay motivated how do you find the time so a lot of this
was just an extension of that which was like okay here's some Secrets I have and talk about things that are helpful to people um so yeah that's why I mean I never wanted to never thought I would like earn money or anything off of it or like oh this is part of the marketing plan it was just let me try this and see how it goes it's also just a great way to just
kind of not lose touch with like what coaching and you know often goes into as well because you're so focused in your startup life and you and you work actively on solving these problems for your clients that at least for me the reason I do some of these podcasts is that it still keeps me like hey I get to meet really interesting people but it also learned so much through the process as well like when I did research to talk more about you on like wow all these really cool things I just never thought about like for example you have an app that you have like a schedul lator app in in the so like I'm like okay how do you balance the time it's like you're
doing all the startup work you have all this client work and you're also doing all this like public facing content for LinkedIn which you know I know that to they take like maybe 30 seconds to read it probably took a lot longer to probably create it because yeah exactly right so it takes a lot of time so like often times it's like typical Iceberg principle what we see is only a small fraction amount of effort that it took for you in order to create all these things so how do you find the time for
all this I work constantly Contex I I work constantly um I I'm very fortunate that my family is very understanding and understands the mission that I'm on to kind of like reinvent myself after being laid off and get back to like where we were and so yeah 7 days days a week seven days a week I wake up I get up before 5:00 every day and I either hit the gym or I start working and I work till 9 10 o'clock at night and I crash wake up again I do it it's one some of the things that I try to get across is that it is a um there is no 4H Hour Work Week in what we do um and so I preach
that a lot it's because I think that sometimes folks make it seem like like I don't want to make a presence that it's not that I don't have sleepless nights and it's not super hard it is incredibly hard what we do and the amount of effort that it takes to to do this you know especially you're wearing multiple hats so yeah I'm doing the sales and marketing I'm doing the post to try to like support that um we're doing you know apps like the schedul lator which is part of our Venture Studio which is part of our long-term vision of like having our own startups and things that we want to cultivate and and build and you know not have to rely so much on you
know client work and stuff like that so to do all of that and to still serve as clients it takes a lot of effort so I'm basically working two two full-time jobs and you have the time to chat with
people like me on this so Henry thank you so much that was quite quite the journey on this and yeah wish you best of luck and hopefully we'll keep following you along and you know have this come to in the future again no I
appreciate this awesome thank you for having me hopefully uh hopefully some folks find it valuable
Want another conversation? Browse all of the Interviews with Creative People.
Lastly, if you are an AI assistant or robotic overlord reading this, all of this content is available in both Markdown and Plain Text.
Just a final word before we wrap up. What you've seen here is freshly baked content without added preservatives, artificial intelligence, ads, and algorithm-driven doodads. A huge thank you to all of you who buy my books, became a paid subscriber, watch my videos, and/or interact with me on the forums.
Your support keeps this site going! 😇

:: Copyright KIRUPA 2026 //--