How York IE CEO Kyle York grew to $12.9M revenue and 25 customers in 2024.

hello everyone my guest today is kyle york he's the co-founder ceo and managing partner at york ie where he sets the company's vision of building a hybrid strategic advisory investment and operational growth firm he works closely with entrepreneurs and investors to help them realize their shared ambition to build great communities new jobs grow general wealth and impact the world investing in over 75 startups over the past decade kyle is also a co-founder and board member of a for third generation family business called york athletics mfg an e-commerce footwear brand based in boston and is also a board member of cams ascent compliance cloud up and forcivity kyle you ready to take it to the top absolutely all right so how should people think about this is this a fund and and york is a platform you just invest through or what is york yeah so sure so thanks for having me david it's really exciting to be here and talk to you yes so i've had a long career operating uh sas businesses startups um you know claim to fame help build a company called dine uh that we built to 100 million ar and sold the oracle uh back in 2016. and in parallel what was the problem jeremy wouldn't tell me the price i had him on my show and i go jeremy what was the price the press says 500 i'm like it's it's enough remove now it's enough years in the past where you could just slip up and there'd be no lawsuit i mean i just say it's a rumored 600 million that's what i like you know so yeah i mean but we had a great success um jeremy and the team we had around us you know we all built just a really fun company and we did it in our hometown in manchester new hampshire and in parallel to that i had been angel investing uh like many of the other dying early executives and doing advising and boards and by the time i ended up staying at oracle spent three years as the general manager of the business unit ran cloud strategy for oracle and you know i kept feeling like the traditional venture capital industry or the conventional sort of way of operating businesses were were binary decisions so i thought i wonder if york ie could enable me to invest but also advise consult build our own sas platform sort of build this kind of vertically integrated uh next generation companies that's really what york ie is a sas business it's a advising consulting business and it's an investment business focused on uh early stage technology setups so let's talk about the sas component first what is the customer paying you for on the sas side so we actually haven't even launched it publicly yet um the uh sas platform is called fuel um we've publicly announced it because it's actually it's a market competitive intelligence platform so it's how we build our investments practice how we do market track day uh tracking uh proactive discovery market thesis um it's also we've today launched um it's sas uh subscription model we've launched three services modules that are almost managed services on top of the sas platform market product strategy business growth strategy and marcom services and so those services start at 3k a month and they scale up from there we basically productize and modularize uh these services using our technology capabilities so they can be hyper scalable uh really uh margin friendly uh and and then over time the idea is it will then open up the sas platform to the market once we build up a bunch of captive uh demanding customers on top of the managed services practice in the investments business so what is the native services practice you mentioned there's there's technology there right yeah so the services practice uh think of it like a private company database um think of it uh you know almost an operator uh version of like traxxan or pitchbook uh that are more based or built for venture funds or private equity funds what we're trying to do um is basically have the most accurate and connected data sets on companies and markets and then we're building a capability called smart notebooks which is really like smart automated templates for things like market research or strength or share of voice collaboration or marketing competitive um sizing and things like that uh company pitch decks they're really like operator tools on top of the data sets to uh scale businesses and we think disrupt markets how many companies you have listed in your private company database currently uh currently um gee that's a great question it's a lot of internet scraping i think the current database is about 800 000 but last i checked uh just this past friday release it's uh we're recording this on a monday uh in mid-october they um we we added the capability to script another three million um companies through our data sets why so many why go so wide instead of deep on a specific specific sector yeah i think it's um you need to get a broad enough cross section of startups in the sort of uh startup community i mean most of the companies think of it like a private company bloomberg portal um there's so many small companies the ability for these companies to get bigger and bigger and bigger um you know it's just a long tail to the startup market right so to be able to cover all the disruptors all the innovations all the features capabilities you need to have a pretty long tail on the market uh we think a lot of the big use case of the technology i mean a lot of it was built on the backs at dying people don't know this we actually acquired 11 companies and and we spun out four different technologies that we sold to other companies and then at oracle my team we had i had hundreds of people who work for me but we had a dedicated 35 strategic development team which is basically marketing competitive intelligence and it was a lot of manual automated research market sizing uh doing proactive market theses um took a lot of human bodies to basically scrape the internet without technology so to do this really well and keep an eye on the ankle biters and also the kind of heavily funded fast growth pre-ipo startups you just need automation and you need a wide a widespread database but but i mean so so i mean you look at what sort of what mattermark did right they tried this they tried selling it to founders and investors and then eventually sales teams and it just failed miserably in the long run and a lot of people when you talk to ex-employees they say the big mistake was danielle gave essentially a thesis that we need to have you know 30 million companies indexed by x date and a lot of people say the mistake that was made is the data was so wide it wasn't differentiated you could just go to pitch book or crunch so so you either have to have a differentiated data set and then go wide and have a data point per each company that other people don't currently have or you say super super focused and go really deep on a specific cohort you're going wide what data point are you going to have on all companies that they can't get elsewhere yeah so i think a lot of those companies just mentioned matamar crunchbase pitchbook they're relying on lots of uh point solutions and point data sets as partners and integrators like an hour built with or and a lot of these i was an investor and shareholder and board member of data knives i was a founding investor who sold the zoom info a lot of these companies are good little companies but they're never going to be venture backed big companies right so a lot of the capabilities that are being integrated into the crunch basis and others from these point products we're actually building ourselves and integrating in the other reason why matter mark wasn't a successful company because they fundraised too much um the entire thesis of my investment firm is take less capital i mean the best part of the dine story is that we didn't raise a dollar of outside capital until we were 30 million ar i'm in the fortunate position to sell self-fund york ie and self-fund our fuel platform so i can actually uh control our destiny control our fate control our cap table and not be beholden uh to investors definition of success or failure so i think it's those two things i mean it's building a lot of the ip ourselves um i think it's launching our services and investments practice on top of the platform ourselves so that we can hone the product the capabilities the automated levers of the cab of the of the platform and then over time decide what parts of it uh to offer to the market i think what you'll see with us is we're building our smart notebooks is really more around automated workflows and uh doing a lot of education and training on how to do market research how to do better amplification how to curate better content um and i think those types of things that we build in as more workflows will also help us not just be a company a tool that you think flow of the user of the operator and that's not always the case so so crowd the revenue model there again sas we know what sas is it hasn't launched yet your strategy and services practice which includes the database it includes smart notebooks that's 3k a month and higher sorry it's breaking up a little bit i don't know if it's is that on your side too or is it just i hear you clearly so what i was saying was you've got three different product lines we know what sas is you talked about strategy and services 3k a month that includes your private company database and smart notebooks is that accurate yeah and then your third pro you know product line is capital you're you're investing correct exactly right walk us through that and so now we focus on how many investments have you made and what's the fun size yeah so we don't run a traditional uh venture fund um we operate an evergreen syndicate so back in 2014 i co-founded the sas syndicate on angelus which remains the largest sas specific uh syndicate on the platform um i co-founded that with gil pensina uh who's a good friend of mine from the industry and um back when i was leaving oracle uh we took that over from gil and we thought at first we just invest our own capital and then leverage the angeles syndicate pretty quickly what we started to learn is that a lot of high net worth individuals and family offices were looking for an alternative in alternative investments from traditional kiss the ring venture funds so what we basically created is a master series vehicle a high net worth individuals and family offices invest alongside our capital there's no traditional management fee and there's no traditional fund economics we get a five-year commitment from our investors to give an annual amount per year uh and they get a percentage of every single deal we do every year and then the economics the york iear we take a carried interest on a deal by deal basis not on a fund-wide basis so we pass through no management fees no uh deal fees uh and we just make money on the economics on the deal by deal carrying interest so it's just a different model it's a little bit more fluid our backers tend to be leveraging our infrastructure sending us their deal flow using us for reporting and tracking um they'll be some of the first outside beta customers of our of our fuel platform um they're bringing a lot of their portfolio for consulting advisory uh to us and it's great and so we've done since we launched actually we just wired a deal today um we've done 17 investments we've deployed right around six and a half million dollars we average about a 500 k check size now because it's evergreen our average check size is going up every year as we bring on more of a capital pool and so we're up to about six and a half million dollars per year to deploy all going into early stage b2b sas businesses because of our heritage you know we have a lot of experience in infrastructure devops dev tools cyber security but we'll go all the way up the stack into vertical uh sas opportunities in tech laggard industries and you know again we lean in you know we're involved it has to be the right mutual pairing you know a lot of vcs say they help and they have operational expertise but we've tr we're truly investing you know we've got a 15-person team ex operators active operators uh we're trying to really be an operational extension from mcgregor so talk to me about on fleet i see them listed on the york ie profile on angellist we just had khaled on the show last week he talked about they're about to break 10 million dollars in revenue obviously covet has been impactful for them considering its last mile delivery they've exploded how are you helping khalid yeah so khalid was actually we've done multiple so khalid's a a i call it a legacy or investment so it was part of our ageless sas syndicate while i was still working at dine and oracle so we actually led one of his early seed rounds and then participated in a couple different seed rounds through angela syndicate and then i was a personal angel investor uh with khalid and the on flip team um we've actually been actively talking to them recently about our marcom services module built on top of our fuel platform um you know a lot of tech startups don't like the minimums of the edelman of the edelmans and the you know pr shops they don't like the siloed nature of media relations in pr and our we call it drum beat marketing it's really more around content marketing means followership content meets media and analyst relations and more of a flywheel approach and a high velocity high urgency approach to content curation getting your market points of view to the world so we've been talking to him a lot uh he's in our prospect pipeline i'll send him this when you post the uh nudge nudge wink wink uh to bring about it okay so it sounds like and so try and quantify this for me so when did you officially launch york ie what year yeah so we launched yorkai last september uh 2019 um we left oracle in the summer of last year after our near three-year run there um but again we brought you know 75 plus angel investments and boards and advisor work that we had been doing me and my two partners joe and adam um to bear so we brought that kind of into the mix so we had a sort of a captive starting point but we we started writing checks last september and you know really really aggressively going we didn't launch our server advisory services practice until this past may um we hired kate campbell out of pan communications what we learned about ourselves as operators as we knew how to operate and we had a lot of know-how but managing accounts and making sure we had processes and and we were more pro programmatic and we could actually account manage really well and do better reporting um we hired someone who came from the services spectrum she's a vp for us who uh who who helps run that practice and she started in may and we launched the service and so how many people are now paying for the services product yeah we have about 25 outside uh clients you know average tickets paying around seven brand a month um for the services so you know we've got ourselves upwards of you know with our with um some of our other project working things we've done we've got ourselves right around a million and a half arr in the first year um and you know we have pretty clear line of sight to continue to grow with this kind of managed services um hybrid model and we plan on launching our sas solution self-serve e-commerce uh team inside sales uh i mean the most successful sas companies always come out i mean from what i've seen at least a glaring pattern is a successful agency spins out successful tech because they've got a built-in base you guys brought a built-in base you join atom with 75 deals you're bringing in you're now selling consulting essentially or managed services and then the sas product higher margin fuel hopefully you onboard those go folks there build a great sas business yeah just it's more automation right it's more streamlined and the way i like to picture it over time is that we'll put out all the content york ie you know we're a top startup blog already in the last 12 months in the world i think we're currently ranked like number 30 in the world for our content we're putting out tons of education tons of curriculum for sas businesses on growth we'll then try to convert users to you know give us their emails or sign up for fuel free paid team etc and then we'll layer on advisory and consulting where right now they're kind of we're getting to that first and then the creamer crop sas businesses early stage sas businesses will invest right so that's the vertically integrated strategy and we launched with that vision it was just faster for us to start investing and then faster for us to launch consulting modules and it takes time to build by ip and emote and technology and and again i think it's what's really cool about it is it really is vertically integrated internally meaning a lot of the road map is for us to be our own first super user both our investments business and kind of our advising consulting business which is an operating extension of these teams so once we eat our own dog food and we're addicted then we'll start opening up to investment partners angel portfolio york ie portfolio direct access for consulting clients and we'll have a minimally viable audience that you know i think will well you know as part of the mix and part of the engagement with york ie we'll find a lot of dogs kyle on that note we're out of time let's wrap up here with the famous five number one what's your favorite business book uh i love thinking number two is their ceo you're following or studying i just follow everything three what's your favorite online tool for building your company besides your own oh that's so good um maybe cloud app i love doing cloud app videos and you know uh uh yeah a little bit cheating but i just want to put that out there okay good and then um how many are sleeping every night oh i see i love that and situation married single kids yeah i'm married to my wife katie who i met at bentley university in college and then i've got three kids henry eight uh teddy five and ev3 so quarantine's been super low that how old are you kyle 38 i'm 38. what am i i'm 37 i turned 38 no i turned 38 that's not but you know a fair fair fair all right 37 today and then take us home here what's something you wishing you when you were 20. oh man i i've always said it now in hindsight but play the long game i mean you can get a lot further along if you play the long game and you set a big big vision and then you work guys doing a 1.5 million run rate right now about 25 customers paying 7 000 per month those customers are founders that are basically paying for managed service strategy and services that joe adam and kyle founded after they left the hugely successful dine they brought 75 deals sort of in with them they're now launching a sas product called fuel to help these founders grow more effectively following automations and playbooks and they're also when they see a company they love making investments they've deployed checks in about 17 deals so far average check size 500 grand they can now deploy about 6.5 million per year via their syndicate on angelus kyle thank you for taking us to the top one more thing before you go we have a brand new show every thursday at 1 pm central it's called shark tank for sas we call it deal or bust one founder comes on three hungry buyers they try and do a deal live and the founder shares back end dashboards their expenses their revenue arpu cac ltv you name it they share it and the buyers try and make a deal live it is fun to watch every thursday 1 pm central additionally remember these recorded founder interviews go live we release them here on youtube every day at 2pm central to make sure you don't miss any of that make sure you click the subscribe button below here on youtube the big red button and then click the little bell notification to make sure you get notifications when we do go live i wouldn't want you to miss breaking news in the sas world whether it's an acquisition a big fundraise a big sale a big profitability statement or something else i don't want you to miss it additionally if you want to take this conversation deeper and further we have by far the largest private slack community for b2b sas founders you want to get in there we've probably talked about your tool if you're running a company or your firm if you're investing you can go in there and quickly search and see what people are saying sign up for that at nathan laca.com forward slash slack in the meantime i'm hanging out with you here on youtube i'll be in the comments for the next 30 minutes feel free to let me know what you thought about this episode if you enjoyed it click the thumbs up we get a lot of haters that are mad at how aggressive i am on these shows but i do it so that we can all learn we have to counter those people we got to push them 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