Table of Contents
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| 029 | 2026-09-15 | prep | Engineer the Business | Thinking Like an Engineer About the Whole Business with Marc Sherwood | The IT Guy Show 029 | Marc Sherwood joins me to talk about applying engineering thinking to the parts of a business nobody optimizes, the revenue cliff open source companies hit, and building your own tools to get unstuck. | Marc Sherwood and I get into what happens when you point engineering thinking at the business itself, not just the product. | Marc Sherwood | Media, live events, and GTM strategy for open source |
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Abstract
Most of us who came up technical learned to optimize one thing: the system in front of us. Find the bottleneck, measure it, fix it, repeat. Then we look at how the rest of the business runs, at the manual handoffs and the spreadsheet somebody rebuilds every Monday and the process nobody has questioned in four years, and we just accept it. That is somebody else's department.
Marc Sherwood does not accept it. He works on media, live events, and go-to-market strategy for open source organizations, which means he spends his time on the side of the house engineers usually shrug at. His pitch is simple and a little confrontational: think like an engineer about the entire business, and optimize all the time.
He also walks it. While we were talking, he built a tool to fix his own job-application process, shipped it, took my feedback, and pushed a fix to production the same afternoon. This episode is about that instinct, where the real roadblocks in a business actually sit, and the revenue cliff that open source companies keep walking off.
Hook
Engineers spend all day optimizing systems and then walk past a business process that has been broken for four years. Marc Sherwood thinks that is a failure of imagination, and today he is going to make the case.
Agenda
Introductions
- Who are you?
- What do you do?
- What do you do for fun?
- How did you end up on the business side of open source rather than the engineering side?
1. Think Like an Engineer About the Whole Business
- Unpack the thesis: what does it actually mean to point engineering thinking at a business?
- The engineering habits that transfer: measure before you change, find the real bottleneck, automate the boring part, make it repeatable
- The habits that do not transfer, and where engineers get it wrong when they try
- "Optimize all the time" sounds exhausting. How do you keep that from becoming churn for its own sake?
2. Creative Uses of Tech to Solve Real Roadblocks
- The tool you built for your own job applications. What was the roadblock, and why build rather than buy?
- Shipping to production the same day you spot the gap. What does that cadence buy you?
- Where does someone non-technical realistically start? What is the smallest useful thing to automate?
- Where do people over-engineer, and when is a spreadsheet actually the right answer?
3. The Open Source Revenue Cliff
- What is the revenue cliff, and why do open source organizations keep hitting it?
- Where the community-to-customer handoff usually breaks
- What engineers at open source companies should understand about how the money actually works
- What GTM people get wrong about technical audiences, and what technical folks get wrong about GTM
4. Media and Live Events
- Why events still matter in a remote-first world
- What actually converts, and what is just theater
- Content as infrastructure: what does a repeatable content system look like?
5. For the Practitioner
- How does an admin or an engineer make a business case that lands with people holding the budget?
- Translating technical work into terms leadership acts on
- What would you tell someone technical who wants more influence over how their company runs?
Wrap Up
- Where to find Marc
- Final thoughts and key takeaways
Closing
- Like / Subscribe
- Next:
- Sign-off: on behalf of my guest, Marc Sherwood, and myself, Eric the IT Guy Hendricks
Keywords
Marc Sherwood, open source business, open source revenue cliff, go to market, GTM strategy, open source monetization, engineering mindset, process optimization, automation, build versus buy, continuous deployment, developer relations, live events, content strategy, technical marketing, IT career
Links
- Linktree: https://linktr.ee/itguyeric
- Marc on LinkedIn: https://www.linkedin.com/in/marcsherwood/
Blog Post
Draft. Rewrite from the transcript after recording.
We will spend a whole afternoon shaving thirty seconds off a build, then walk past a business process that has been broken since before we got hired and think nothing of it. Marc Sherwood thinks that is backwards, and he made the case to me.
{{< episode >}}
A few things worth carrying away from this one:
- The engineering mindset transfers further than we give it credit for. Measure first, find the real bottleneck, automate the boring part. None of that is specific to code.
- Build the small thing. Marc needed a better job application workflow, so he built one, shipped it, and had a fix in production the same day I gave him feedback. That instinct is the whole episode in miniature.
- The revenue cliff is real. We got into why open source organizations keep hitting it and where the handoff from community to customer usually breaks.
Social Posts
Draft. Rewrite after recording.
We will spend an afternoon shaving thirty seconds off a build, then walk past a business process that has been broken for four years and think nothing of it.
For episode 029 I talked with Marc Sherwood, who works on media, live events, and go-to-market for open source organizations. His pitch is that you should think like an engineer about the entire business, not just the part that compiles.
A few things you'll pick up:
- Which engineering habits actually transfer to the business side, and which ones backfire
- Why he built his own tool instead of buying one, and shipped a fix the same day
- What the open source revenue cliff is and why companies keep walking off it
- How to make a technical business case that people holding the budget actually act on
[PASTE YOUTUBE URL]
#OpenSource #DevOps #GTM #Automation #ITCareers
Twitter/X
Draft. Rewrite after recording.
We'll spend an afternoon shaving 30 seconds off a build, then ignore a business process broken since 2022. For 029 Marc Sherwood makes the case for pointing engineering thinking at the whole business, plus the open source revenue cliff. [PASTE YOUTUBE URL] #OpenSource #DevOps
Bluesky / Mastodon
Draft. Rewrite after recording.
We will spend an afternoon shaving thirty seconds off a build and then walk right past a business process that has been broken for years. For 029 I talked with Marc Sherwood about thinking like an engineer about the entire business, building your own tools, and the revenue cliff open source companies keep hitting.
[PASTE YOUTUBE URL]
#OpenSource #DevOps #Automation
YouTube Ad
- Final URL: [PASTE YOUTUBE URL]
- Display path 1: IT-Guy-Show
- Display path 2: Open-Source
- Short headline: The IT Guy Show
- Long headline: You Optimize Systems All Day. Why Not The Business Around Them?
- Description: Linux, homelabs, and open source for the people who actually run the infrastructure.
- CTA: Watch Now
Production Notes
- Marc said yes on 2026-07-17 ("For sure! Anytime") and Eric promised an episode guide that never went out. Lead the outreach by acknowledging the delay.
- His stated topic, verbatim: "mostly around creative uses of tech, to solve existing roadblocks. Think like an Engineer about the entire business. Optimize all the time."
- Concrete example already in hand: the markdown-based resume and job-application tool he built, which flags gaps in an application. Eric gave feedback on the missing markdown-to-PDF export and Marc shipped it the same afternoon. That story is the best opener for section 2.
- Marc also made the Docker introduction for Eric in May, so the relationship is warm.
- Recording after the Linux Prepper interview.