StarZero All shows Try the podcast clipper →

Aug 22, 2020 · 17m · top-founders

Ironman Software Hits 1500 Customers, $300k Revenue Selling Powershell Microsoft Tool

Adam Driscoll · 9m spoken Nathan Latka · 6m spoken Eric Yuan · 4s spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

Ironman Software founder Adam Driscoll explains how he bootstrapped an on-premise PowerShell management suite to $300,000–$400,000 in annual revenue across 1,500 enterprise customers with a 1.5-person team.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 39.7% of the talking time here. How this is scored →

Nathan as informed peer 4.0 Guest teaching 3.4 Guest disagreement 1.4 Nathan pushing back 2.6
05100:0010:000:11–4:09 · Nathan as informed peer 3/10 GetLatka Subscription Announcement and Platform Overview Following the subscription intro, Nathan asks beginner-level introductory questions about PowerShell and Ironman Software's products. Adam explains the core technology and how enterprise clients like Harvard use it for internal admin tasks.4:09–8:00 · Nathan as informed peer 5/10 On-Premise Architecture and Server Licensing Model Nathan drills into the on-prem per-server pricing model and pushes Adam to explain how he actually acquired 750k initial downloads rather than just explaining the paywall. Adam details how Microsoft eventually featured the open-source extension directly in Visual Studio.8:00–12:14 · Nathan as informed peer 6/10 First Paywall Launch and Early Pricing Experiments Adam candidly describes his initial underpricing mistakes and low conversion rates. Nathan quickly synthesizes the paid license metrics and revenue shares to calculate the overall annual business run-rate.12:15–15:23 · Nathan as informed peer 4/10 Bootstrapping, Churn Dynamics, and Perpetual Licensing Adam educates Nathan on why churn looks high due to perpetual licensing models rather than active cancellations. Nathan mistakenly assumes PowerShell is Adam's proprietary tool, and Adam clarifies that it is Microsoft's scripting language ecosystem.15:23–16:54 · Nathan as informed peer 2/10 Famous Five Rapid-Fire Questions A standard, friendly Famous Five rapid-fire exchange covering favorite books, CEOs, Ironman race day nutrition, and advice to a younger self.0:11–4:09 · Guest teaching 3/10 GetLatka Subscription Announcement and Platform Overview Following the subscription intro, Nathan asks beginner-level introductory questions about PowerShell and Ironman Software's products. Adam explains the core technology and how enterprise clients like Harvard use it for internal admin tasks.4:09–8:00 · Guest teaching 4/10 On-Premise Architecture and Server Licensing Model Nathan drills into the on-prem per-server pricing model and pushes Adam to explain how he actually acquired 750k initial downloads rather than just explaining the paywall. Adam details how Microsoft eventually featured the open-source extension directly in Visual Studio.8:00–12:14 · Guest teaching 4/10 First Paywall Launch and Early Pricing Experiments Adam candidly describes his initial underpricing mistakes and low conversion rates. Nathan quickly synthesizes the paid license metrics and revenue shares to calculate the overall annual business run-rate.12:15–15:23 · Guest teaching 5/10 Bootstrapping, Churn Dynamics, and Perpetual Licensing Adam educates Nathan on why churn looks high due to perpetual licensing models rather than active cancellations. Nathan mistakenly assumes PowerShell is Adam's proprietary tool, and Adam clarifies that it is Microsoft's scripting language ecosystem.15:23–16:54 · Guest teaching 1/10 Famous Five Rapid-Fire Questions A standard, friendly Famous Five rapid-fire exchange covering favorite books, CEOs, Ironman race day nutrition, and advice to a younger self.0:11–4:09 · Guest disagreement 1/10 GetLatka Subscription Announcement and Platform Overview Following the subscription intro, Nathan asks beginner-level introductory questions about PowerShell and Ironman Software's products. Adam explains the core technology and how enterprise clients like Harvard use it for internal admin tasks.4:09–8:00 · Guest disagreement 2/10 On-Premise Architecture and Server Licensing Model Nathan drills into the on-prem per-server pricing model and pushes Adam to explain how he actually acquired 750k initial downloads rather than just explaining the paywall. Adam details how Microsoft eventually featured the open-source extension directly in Visual Studio.8:00–12:14 · Guest disagreement 1/10 First Paywall Launch and Early Pricing Experiments Adam candidly describes his initial underpricing mistakes and low conversion rates. Nathan quickly synthesizes the paid license metrics and revenue shares to calculate the overall annual business run-rate.12:15–15:23 · Guest disagreement 2/10 Bootstrapping, Churn Dynamics, and Perpetual Licensing Adam educates Nathan on why churn looks high due to perpetual licensing models rather than active cancellations. Nathan mistakenly assumes PowerShell is Adam's proprietary tool, and Adam clarifies that it is Microsoft's scripting language ecosystem.15:23–16:54 · Guest disagreement 1/10 Famous Five Rapid-Fire Questions A standard, friendly Famous Five rapid-fire exchange covering favorite books, CEOs, Ironman race day nutrition, and advice to a younger self.0:11–4:09 · Nathan pushing back 1/10 GetLatka Subscription Announcement and Platform Overview Following the subscription intro, Nathan asks beginner-level introductory questions about PowerShell and Ironman Software's products. Adam explains the core technology and how enterprise clients like Harvard use it for internal admin tasks.4:09–8:00 · Nathan pushing back 5/10 On-Premise Architecture and Server Licensing Model Nathan drills into the on-prem per-server pricing model and pushes Adam to explain how he actually acquired 750k initial downloads rather than just explaining the paywall. Adam details how Microsoft eventually featured the open-source extension directly in Visual Studio.8:00–12:14 · Nathan pushing back 3/10 First Paywall Launch and Early Pricing Experiments Adam candidly describes his initial underpricing mistakes and low conversion rates. Nathan quickly synthesizes the paid license metrics and revenue shares to calculate the overall annual business run-rate.12:15–15:23 · Nathan pushing back 3/10 Bootstrapping, Churn Dynamics, and Perpetual Licensing Adam educates Nathan on why churn looks high due to perpetual licensing models rather than active cancellations. Nathan mistakenly assumes PowerShell is Adam's proprietary tool, and Adam clarifies that it is Microsoft's scripting language ecosystem.15:23–16:54 · Nathan pushing back 1/10 Famous Five Rapid-Fire Questions A standard, friendly Famous Five rapid-fire exchange covering favorite books, CEOs, Ironman race day nutrition, and advice to a younger self.

speaking balance: gold is Nathan, purple is the guest (3 minute bins)

0:00 · Nathan 58.7% · guest 41.3%0:00 · Nathan 58.7% · guest 41.3%3:00 · Nathan 32.6% · guest 67.4%3:00 · Nathan 32.6% · guest 67.4%6:00 · Nathan 28.5% · guest 71.5%6:00 · Nathan 28.5% · guest 71.5%9:00 · Nathan 27% · guest 73%9:00 · Nathan 27% · guest 73%12:00 · Nathan 24.4% · guest 75.6%12:00 · Nathan 24.4% · guest 75.6%15:00 · Nathan 74.7% · guest 25.3%15:00 · Nathan 74.7% · guest 25.3%
Sharpest disagreement ▶ 13:08 Reframing churn under perpetual licensing

Adam pushes back on traditional SaaS churn assumptions, pointing out that customers who do not renew maintenance still actively use the perpetual license software.

 Hardest push from Nathan ▶ 6:58 Pressing on true user acquisition mechanics

Nathan cuts off the paywall explanation to firmly press Adam on how an engineer organically achieved 700,000+ developer downloads.

 Biggest teaching moment ▶ 14:25 Correcting the host on PowerShell ownership

Adam clarifies that PowerShell is Microsoft's foundational scripting language and explains his status as a community MVP rather than the creator of PowerShell itself.

 Nathan holds their own ▶ 11:36 Rapid calculation of total company revenue

Nathan performs on-the-fly financial modeling using product revenue splits and license counts to establish the company's $300k-$400k revenue run rate.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
GetLatka Subscription Announcement and Platform Overview 3311 Following the subscription intro, Nathan asks beginner-level introductory questions about PowerShell and Ironman Software's products. Adam explains the core technology and how enterprise clients like Harvard use it for internal admin tasks.
On-Premise Architecture and Server Licensing Model 5425 Nathan drills into the on-prem per-server pricing model and pushes Adam to explain how he actually acquired 750k initial downloads rather than just explaining the paywall. Adam details how Microsoft eventually featured the open-source extension directly in Visual Studio.
First Paywall Launch and Early Pricing Experiments 6413 Adam candidly describes his initial underpricing mistakes and low conversion rates. Nathan quickly synthesizes the paid license metrics and revenue shares to calculate the overall annual business run-rate.
Bootstrapping, Churn Dynamics, and Perpetual Licensing 4523 Adam educates Nathan on why churn looks high due to perpetual licensing models rather than active cancellations. Nathan mistakenly assumes PowerShell is Adam's proprietary tool, and Adam clarifies that it is Microsoft's scripting language ecosystem.
Famous Five Rapid-Fire Questions 2111 A standard, friendly Famous Five rapid-fire exchange covering favorite books, CEOs, Ironman race day nutrition, and advice to a younger self.

Statements from this episode (13)

Assertion Not checkable as stated
Harvard uses Ironman Software dashboards for internal IT administration
“So Harvard is building primarily like universal dashboard websites with PowerShell, so they're using it to manage their IT systems inside pretty much their, like, back-end stuff, so managing actual directory and that kind of thing. To allow their users who don…”
Adam Driscoll Aug 22, 2020 ▶ 3:25
Disclosure
Ironman Software customers pay an average of $400 per year
“So primarily, I'd say on average, customers are paying us around 400 dollars a year. Our larger customers are paying, you know, anywhere from 2000 dollars a year to some of them are upwards of 6000 dollars a year.”
Adam Driscoll Aug 22, 2020 ▶ 4:47
Assertion Not publicly verifiable
PowerShell Tools for Visual Studio reached 750,000 peak free installs
“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.”
Adam Driscoll Aug 22, 2020 ▶ 6:20
Assertion Supported
Microsoft included Driscoll's open-source tool in the Visual Studio installer
“They got ahold of these guys at Microsoft, and then eventually Microsoft promoted it. Like it was, you know, on their website, and it eventually was in the installer for a little while, that kind of thing. You could actually select a feature and install my pro…”
Adam Driscoll Aug 22, 2020 ▶ 7:40
Assertion Not checkable as stated
Ironman Software generated roughly $15,000 in first-year sales
“My first year I did probably 15,000 dollars of sales.”
Adam Driscoll Aug 22, 2020 ▶ 8:50
Assertion Not checkable as stated
PowerShell Pro Tools sees 1,000 yearly licenses from 400,000 free installs
“PowerShell Pro Tools install base is, it's hovering around 400,000 for the install base of free. I'd say I'm selling about a thousand licenses a year kind of thing right now.”
Adam Driscoll Aug 22, 2020 ▶ 10:07
Assertion Not checkable as stated
PowerShell Universal sees 500 paid installs from 60,000 free installs
“I think we have probably you know, like 500 installs that are paid, sort of thing. and then from there, you know, we have some free features that you can use without it, so it's about 60,000 actually free Free installs of PowerShell Universal.”
Adam Driscoll Aug 22, 2020 ▶ 10:30
Assertion Not checkable as stated
Ironman Software has approximately 1,500 paying customers per year
“I would say I probably have you know, 1500 paying customers per year kind of thing.”
Adam Driscoll Aug 22, 2020 ▶ 11:31
Disclosure
Ironman Software is an entirely bootstrapped business
“Bootstrap.”
Adam Driscoll Aug 22, 2020 ▶ 12:43
Assertion Not checkable as stated
PowerShell Pro Tools sees roughly 25% annual churn
“I honestly couldn't give you a good number, but I would bet that on the PowerShell Pro Tools side, I would say it's probably like 25%.”
Adam Driscoll Aug 22, 2020 ▶ 13:00
Assertion Not checkable as stated
Universal Dashboard and PowerShell Universal see roughly 10% annual churn
“But on the Universal Dashboard and PowerShell Universal side, it's probably more around 10% kind of thing.”
Adam Driscoll Aug 22, 2020 ▶ 13:10
Assertion Supported
Ironman Software sells perpetual licenses instead of subscriptions
“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.”
Adam Driscoll Aug 22, 2020 ▶ 13:17
Disclosure
Ironman Software acquires 99% of its customers organically
“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.”
Adam Driscoll Aug 22, 2020 ▶ 13:51
Made with StarZero

Turn any episode into a week of clips.

This entire site, over 2,600 episodes transcribed, diarized, checked and made playable, runs on the StarZero media pipeline. Drop in your own episode and the podcast clipper finds the moments worth sharing, cuts them, captions them, and reframes them for every feed.

Try the podcast clipper Learn more