Month: September 2025

Years ago I was in a conversation with someone who was asking some curious, albeit weighted questions around the subject of using the Office365 product suite over GSuite. It was a decision made in this organization prior to my coming on-board, but honestly I felt it was a good decision and supported it. One train of questioning was about some feature set related to cloud first solutions and collaboration features. The unfortunate part of the conversation is that, unless there’s a genuine intellectual curiosity about the subject, going into all the ins and outs of cost analysis and directionality is generally useless since it won’t be heard well.

It didn’t matter that the year was 2016, Satya Nadella had just started 2 years prior, the consent agreement that constrained much of their product development had ended only 5 years previously, and they were consistently retooling towards a cloud first posture. It didn’t even matter that the O365 was, even then, a greater ROI in terms of cost/feature comparable to GSuite. The person did not understand the market situations that led up to that moment and were just trying to get through their job.

It makes sense. So many times i’m in the same boat and judge a tool harshly without knowing further context into the whys and hows.

Obviously, we’re in a different world now. Not saying Microsoft is THE way, that very much depends on individual use cases. It is A way, and their innovation chops have been proven over the past decade. Full disclosure on my cards, in terms of use i’m at a 50/50 split. There are 2 organizations I work in that use GSuite and 2 that use O365. There are specific reasons you would use one or the other but none of those reasons are that one is better than the other.

Here’s the big idea: judging a product maker without a further understanding of the market dynamics that drove their product in one direction or another doesn’t help you understand something in a nuanced way where you can capitalize on it for greater returns. At the end of the day, a hard stance on a product isn’t the job. Making good decisions and understanding the nuance of those decisions in order to produce value for an organization is.

I’m interested in who else has run into this problem. Is there a “succesful” tool (good TAM, SOM, SAM) you look at that you think is THE WORST that you might need to re-underwrite?

Something I’ve noticed in some conversations is when a person tells me something is complex and difficult to explain it has become a red flag for me. I try to go by the napkin rule. If I can’t draw it out on a diner napkin over lunch with someone then it’s possible I don’t really understand the first principles of the subject.

To be clear, there are some things that truly are complex. Any discrete structures and algorithms class will teach you that is true. Even so, that same subject can be broken down to foundational elements that can be explained.

W2 multiple is a great example of this. I’ve seen very odd calculations of this. Things where someone looked at all the time a person was putting that was billable and non-billable, etc. The measures i’ve seen this way and their use case made sense because the term was being used as a descriptor of how hard someone was working. The thing is, that is not a W2 multiple.

Simply put W2 multiple is how much revenue you get per W2 payout. e.g. if you earn $120,000 and you pay out $60,000 then your W2 multiple is 2 because $120,000/$60,000=2. If you use any other calculation and call it W2 multiple then you’re saying the wrong thing and there is a high potential that others are hearing the wrong thing.

I’m using W2 multiple as the example, but we can say the same thing about many areas like this. When you say EBITDA, don’t say “community adjusted EBITDA” because that’s not a thing <cough>WeWork</cough>. If you’re “full stack”, please understand hardware too. Containerization is needed but it’s not the full stack.

With industry standard terms it helps to use the industry standard definition. If you don’t know how to define some of those things then it’s possible you don’t know your job as well as you think you do. I’m still there many times. What’s the goal then? Not to not discuss, the goal is to be aware, curious, and questioning. As questions and approach as a learner not as a learned. For me this has to stay true. My current thing i’m learning is containerization so I can increase my BS meter when talking to devs. Let’s all stay curious.

What about you? Please comment, what are you learning?

Had a conversation with a friend the other day who works for a municipality. There is a software that they use, basically every county uses it. There’s one vendor for everyone. It’s a monopoly. Support is bad (days for the initial response), product is bad (still requiring windows 10 and haven’t began testing for deployment in windows 11), and prices are high (no market competition = high prices). The issue is anytime a new company begins to disrupt they buy them.

To be clear, i’m not against monopolies if you got there through innovation. I’m not even against M&A as that is a solid strategy that fuels startup funding and what folks like Lina Khan are doing is showing how little some understand about the free markets and game theory. However, in this instance it’s a clear case of anti-competitive behavior and the reason it hasn’t become a case is because the acquisitions aren’t large enough to garner attention.

Back to the conversation with my friends, one was saying they didn’t know how to code this. My case to him was that it was unnecessary. He had the right knowledge.
1) problem set
2) deliverables and requirements
3) understanding of current constraints
4) industry experience and relationships

In this case, the issue would be the why to build. If the real core why is to disrupt by adding competition, there are risks there and they’re all surmountable. Just have to be clear enough on the why to not sell when the money is a high multiple and look for a better exit with good partners to keep the competition alive.

Given the state of tech today, it’s the easiest time to build a company with $0 in funding so long as you’re willing to put in the work. What about you? Feeling the itch to innovate? What’s stopping you from starting as an intrepreneur where you’re at? Whats stopping you from starting as an entrepreneur and launching out? Now that you know what’s stopping you, you’re a very powerful person so what’s the plan to remove those obstacles?