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...