How Ironmansoftware CEO Adam Driscoll grew Ironmansoftware to $3M revenue and 1.5K customers in 2024.

hello everyone my guest today is adam driscoll he's a solo founder microsoft mvp and longer time open source contributor his software is used by hundreds of thousands of people worldwide when he's not working he's an outdoor enthusiast long distance endurance endurance athlete and beer lover adam you're ready to take us to the top yeah definitely are you an ipa kind of guy or what oh definitely big ipa gay nice very cool and you do that before or after the iron man run uh definitely after i've tried that before it doesn't work out so well i hear i hear that doesn't work so well all right so so what are you working on at ironmansoftware.com what's the technology do sure so uh we kind of have two different products or um our two products are powershell universal which is a platform for building web-based it tools so the idea there is that people that kind of know powershell and kind of want to like integrate with other technology in their environment they can use powershell universal to build websites and apis and automations on top of their powershell scripts so um that's cool because a lot of you know devops i.t guys don't really have the chops necessarily to build a website or build up an api like that but this kind of gives them the ability to do so um and then our other product is powershell pro tools that's kind of been along around for a long time um and it is a bunch of different uh tools that we have for powershell to kind of build or like on-prem or desktop tools using uh powershell scripts and and for those of us that are not technical what it helps understand what powershell is give us an analogy sure so powershell is a scripting language um that microsoft developed and it pretty much is used for integrating with uh both microsoft's on-prem windows systems uh as well as like their azure technology and they've kind of brought it into the uh cross-platform world now so you can manage linux and that kind of thing so harvard uses you how does harvard use you so uh harvard is building primarily uh like uh universal dashboard websites with powershell so they're using it to manage their i.t systems inside uh pretty much they're like back end stuff so managing actual directory and that kind of thing um to allow their users who don't know how to run powershell scripts to like unlock user accounts or reset passwords that kind of thing so it's more sort of internal admin a harvard student's never going to go to like the scholar.com website and see sort of like in their course builder your tool is powering the course builder at harvard it's more like back and admin stuff yep exactly so primarily people are building like tools to yeah administer stuff inside environments interesting okay and help me understand pricing here is this a pure play sas business or mix uh it's actually mostly on-prem right now so uh we our technology is kind of built in terms of in a way that we could make it a sas business so we we aren't doing that right now but uh primarily people are installing this on their uh you know internal environments and then uh we're licensing that based on uh like kind of the per server licensing model so okay and on average sort of obviously you have to calculate how many servers per customer but on average what's the customer paying you per year or per month to use this uh so primarily i'd say on average customers are paying us around 400 a year um well our larger customers are paying you know anywhere from two thousand dollars a year to um some of them are upwards of six thousand dollars a year so it just kind of depends on how many servers they're rolling out so if i'm paying you 400 bucks a year how many servers do i probably have with you oh that's just one server so one server got it yeah but you kind of get all the features all the features of the product um at that price point so and is there literally like you obviously don't you don't sell the hardware do you no no yeah yeah yeah okay so if i had one of these servers in a cool little room in my home office here with air conditioning and blue lights in the background and fans and spinners and cables if i had that installed i could essentially buy your software 400 bucks a year install it on my on-prem server for security purposes and then run these integrations you talked about on the back end yep exactly interesting when'd you launch the company what year uh started fall of 2017. so um we were actually i actually released the powershell pro tools first that was kind of like a freemium model of one of the open source projects that i had been doing for a long time so i decided that it was really popular and that i needed to kind of monetize it so you launched a freemium version in 2017 of that of that tool yeah yep how did you get the first 100 like freemium downloads uh well actually the open source project that i had running was powerful tools for visual studio so visual studio is microsoft's development environment i added i added the powershell language support to that and uh prior to me actually making it into a freemium tool it was a free tool and that had i think at its peak about 750 000 installs so i realized that that was like a i probably should like try to sell something in there so yeah that's what i did is i i added some features that uh you know people could buy um so it was more or less like that that install base just it automatically updates and then they kind of saw my new features that they could purchase and then from there i kind of set up a website and people could buy buy elections but that's adam let's go back though so before you launch the paid features and people see the paid pop-up i get that and there's a conversion rate from free and result to paid i get that but take me back to the beginning they're like where were you actually so i understand you built you said you built this for visual basic uh visual studio visual studio but how did you get 700 000 downloads it's not easy were you like ranked really high in like the app store or on a subreddit form somewhere or sub stack or how did you get the downloads uh so it was uh internally i was working at a large like fortune 100 software company kind of thing and i built it in my free time and then we had some guys there that had some i don't know uh friends at microsoft sort of thing um so when they saw that i built that open source tool they got a hold of these guys at microsoft and then eventually microsoft promoted it like it was you know on their website and um it eventually was in the installer for a little while that kind of thing you could actually select a feature and install my product oh wow yeah so that's pretty cool okay so that makes sense all right so you launched some new paid features now when did you launch that paid that pay while for the first time uh that was like september 2017. okay guys september 2017. and so walk me through you're an engineer so i always like asking engineers how you think about pricing because it's like toxic to you so yeah how did you think about what price point to put on the new features oh man i was like way low you know i was like uh people you know i i have 750 i did like the math i have like i have 750 000 installs or whatever right i'm going to charge 25 bucks a year for you know this paid feature kind of thing and um from there it was kind of like oh yeah okay easy millionaire sort of thing but uh you know like 99.9 of people didn't buy even at that price point and how was it buy i think my first like my first year i did probably fifteen thousand dollars with the sales so it was it was okay like 600 700 people purchased something like that yeah something like that so uh i think by the end of 2018 i had at least doubled or tripled the price that i was charging kind of thing so um yeah so uh that continues to be a pretty a pretty good seller for me actually it's probably about 40 of my business still oh wow interesting okay that's great and that is the sort of one time or actually no it's you know the annual 25 per year sort of upsell yeah so that's actually a hundred dollars per year so i actually i've i've increased it a little bit because i've added a lot more features and that kind of thing but um yeah it's uh it's still doing pretty well that's not that's fantastic so is it just you i mean there's just you on the team you're the one doing all the updates uh yep uh for that product i am i do have a contractor in israel that's helping me on the partial universal side of things doing some of the front-end development about 20 20 hours a week sort of thing so um but mostly it's just me and how many people are now paying for that and what's the new install base including free uh so let's see powershell pro tools install bases it's hovering around uh 400 000 for the install base of free um i'd say i'm selling about a thousand licenses a year kind of thing right now so uh that's doing pretty well and then um for powershell universal the install base is a lot smaller i think we have probably uh you know like 500 uh installs uh that are paid sort of thing yeah um and then uh from there you know we have some free features that you can use without it so it's about 60 000 actually um free free installs of powershell universal so yep yep uh interesting and up so you're adding in terms of growth on powershell pro a thousand new licenses per year but i imagine i mean you started selling things back in 2018 so you should have people like paying for multiple years at this point like if you just take a snapshot of like today how many paid accounts do you have uh honestly i don't have that number on hand kind of thing but that's okay i would say uh my churn rate's a little high for that because it's very much a one-off tool i've found that people will like purchase it use it for like the specific thing they want to do and then not renew kind of things the longevity isn't quite there with that product and that's one of the reasons i started using powershell universal but i would say i probably have um you know 500 paying customers per year kind of thing so i see i see okay got it so that part of the business sort of does like 150 grand a year or something like that got it and that's 40 to your business so all together these other products you've launched your cost say 300 400 000 a year sort of business so your instant millionaire is happening it's just it's a couple years later yeah right yeah it's taking a while so yeah um but it's getting to the point where uh it's i'm comfortable enough where now i can kind of start to grow the business it's been it's been fun being the solar entrepreneur and doing all the things but i'm looking forward to kind of like uh taking some of that cash and reinvesting it and hiring some people kind of thing so what is the next tire or who is the next hire uh that's a really good question i think i need some help on the business side sort of thing i'm very bad at pricing i'm very good at marketing i'm very bad at like that kind of thing i could use uh use some help there i'm a very much tech savvy guy i like building the software i like doing that kind of thing so i'm going to start looking into either marketing and kind of the business side or i need some help with support so that's kind of where i'm looking and have you bootstrapped the company or raised uh bootstrap i love that that's great yeah and the team today is just two of you guys right uh yeah one and a half i'd say yeah one and a half no no no sales no marketing no nothing yet right yeah i love that okay and and talk to me you mean you mentioned annual churn is pretty high what is it i honestly couldn't give you a good number but i would i would bet that on the powershell pro tools side i would say it's probably like 25 churn annually yeah yeah um but on the universal dashboard and powershell universal side it's probably more around 10 kind of things so they're still pretty high but um one of the things is that both of the licenses are perpetual licensed right now so it's not like a subscription based or anything like that so if people decide not to upgrade or pay for maintenance then they don't have to continue to pay me sort of thing so if they're happy happy with the you know the version they have that kind of thing then there's no need to upgrade so they could technically still be using my software just they're not paying for a license so but they paid once like three years ago 100 bucks exactly i see i see interesting okay any paid marketing spend like do you have cac for these new customers or it's all organic uh it's i'd say it's 99 organic i've probably spent like a thousand dollars on some paid marketing here and there but it really hasn't panned out i i realized i probably need to spend a lot more to actually see that but well what so what is the i mean how are people finding you today because it's not via like your website and seo there's not a lot of traffic going there so i'm assuming you're built into some app exchanges or something yeah so there's the visual studio marketplace which is one big uh place that people are finding me and then there's this partial gallery where people can like download powershell extensions that kind of air modules and uh they'll find me through that oh powershell is not your thing that's another tool that you sort of built on top of yeah so powershell is scripting and shell language by microsoft so they actually yeah there's a whole ecosystem there around that and you know i have you know i have an mvp a microsoft mvp in the powershell space so i kind of have like a voice inside that i guess domain um so that's kind of the other way i do that when microsoft hosts a power shell user conference you're like a freaking celebrity yeah exactly it's like the only time i like i'm walking around and feel like it's adam driscoll you know that's hysterical i love that you know what they they say in my side of the world sales and marketing they say there's riches in the niches so you know you're it's it's not bad to be hyper focused like that and super popular in a hyper focused spot uh very cool okay got it so bootstrap company two folks looking to sort of scale today mainly organic you're getting it through the visual studio sort of exchanging the powershell galleries um very cool let's uh let's wrap up here with the famous five item number one what's your favorite business book that's a really good question um i like the four-hour work week i don't know if you count that as a business book necessarily but i kind of like some of the concepts in there sort of thing um it just got me thinking a little bit differently about my business number two is there a ceo you're following or studying um i am reading satya nadel's book right now actually um i am really fond of him just seeing the way he transformed microsoft so i really like that number three i usually ask what's your favorite online tool for building your company but i want to change because i'm seeing the awards hanging behind you on your clothes rack which i believe are iron man awards so my question for you is actually a little bit different if if today you're running an iron man in like three hours what are you putting in your body three hours prior to an ironman what are you eating uh let's see i'm drinking a lot of water and every morning before like an iron man i eat a donut okay so that you don't have like some like nootropic weird herb weird concoction you blend together it's just a donut dunkin donuts donut what kind of fully glazed sprinkles or no uh glaze no sprinkles all right number four how many hours i sleep to eat every night uh i'd say seven on average and what's your situation married single kids uh married any kiddos no kids okay how old are you uh 34. 34. last question what do you wish your 20 year old self knew ooh don't give everything away for free guys there you have it iron man software playing in a microsoft scripting scripting language called powershell he built this inside of a fortune 100 company but now has and does between 300 and 400 000 a year in revenue selling a combination of one time or actual perpetual licenses plus a maintenance contract but really trying to work towards this more sort of subscription recurring revenue he's got about 1500 companies today paying sort of 20 to 30 bucks per uh per month which is 340 per year per server install essentially so he does have sort of a way to scale this we'll see what happens next doing it all bootstrapped has full flexibility just a team of two adam thanks for taking us to the top yeah thanks again