Cash Rules Every AI Around Me

I debated whether I should join the fray of technologists talking about AI but, as an elder millennial, I think there’s an angle to this story that isn’t really being discussed — and it has a lot to do with money. Or rather, the tenuous balance between innovation and profit.

Right now, everyone’s talking about how AI is our future and will deeply transform the way we live and work — this has already begun and I don’t think it’s far fetched to believe that we still don’t quite yet know the ways in which this will fully change us until we are living in the change. However, it’s also true that all the large operators in this space are desperately seeking profitability more than they are the lofty ideal of artificial general intelligence. And the need for a return on investment, especially with valuations reaching the trillions for some, will ultimately create winners and losers.

I think back to the early days of the internet — at least as I knew it. When I was an adolescent, we got a personal computer in our home and a subscription to America Online would routinely tie up the telephone line (pre cell phones!). In that time is when I started learning how to code by seeing HTML side by side with the website I was creating. And it was incredibly accessible to get started; whether it was HyperMart, Geocities, or AngelFire, you could very easily spin up a website for free, no ads.

With age and hindsight being 20/20 and all, I now realize what was happening. All that was free to us wasn’t actually free, we were a generation being poked, prodded and tested. Giving it all away for free was incentivizing us to get hooked on the internet which, after the dotcom bust, certainly resulted in some learning for the winners — they had to somehow shift consumer behavior, or tap into it, to drive profitability. We were all hooked on search engines, so that became the next logical place to put ads and a whole economy was born. And then we adapted: we went from the internet not being a valid source for school papers to Wikipedia — the internet’s encyclopedia — becoming a highly authoritative source of truth.

Now thinking about where we are in 2026, we’ve again been given free tools to play with and ultimately get hooked on. Remember when everyone was posting photos of themselves in classic paintings? Congrats, you were helping train the LLMs we have today. And, to be clear, you don’t actually have to pay for any subscription to get fairly decent outputs from Claude so my prediction is get ready to wait through ads (unless you are on a paid subscription)!

Why am I writing all this now?

When you look around, it all can look and sound fairly bleak — but I think that’s always been the case, even in the early days of the internet which we look back on as the halcyon days. In those times, there were strangers talking to a minor like me in chat rooms telling me their age / sex / location which was likely completely fabricated. There were no terms of service to agree to, no privacy policy. Yes, you could be creating a website or blog about your favorite TV or, you could easily be creating disinformation. It was truly a wild west time: lots of innovation, limited regulation, and a healthy amount of fear that this could all go terribly wrong.

We are seemingly back in the wild west period where we have a handful or so of top companies driving the innovation, limited appetite to strongly regulate (to help drive the innovation vs stifle it) and fear that we are effectively ceding all our agency to robots (building the SkyNet that existed in the Terminator film franchise).

Much like the early days of the internet, I think there will be a lot of promise fulfilled but not exactly the way we imagined. I remember thinking the personal computer would let me watch my favorite TV shows on demand — which eventually happened, all for the cost of a streaming service or two (or 5…). I also remember video being so friggin janky in those early days and now we assume video content should be relatively easy to stream from devices that fit in our pockets. And there are so many ways in which the internet has democratized access in really positive ways: ensuring stories are told from frontlines around the world, providing more accessible solutions to the impaired, creating a career path for yours truly, and everything else in between.

I’d like to believe that, when the dust settles, “artificial intelligence” (the blanket term we apply to all kinds of compute-heavy disciplines from natural language processing to computer vision) will hopefully stop being over-used as a term and we can really begin to see this innovation as assistive technology that augments human potential versus destroying it. And, instead of AI taking jobs (a convenient scapegoat to blame when you’ve over-hired and underperformed as a management team), my hope is these tools will just make up the standard issue workplace technology in the same way a mobile device / “bring your own device” is now a standard in most workplaces with appropriate safeguards in place.

I say all this also hoping that the impact of this technology on communities and natural resources is mitigated. With the high cost of compute and my imaging that consumers would be reluctant to pay for multiple LLMs (unlike streaming services), I imagine model providers will be required to optimize their most frequently used models to reduce their overhead and/or ensure the cost passed along to the customer is reasonable for them to bear — as, after all, it’s all about the money!

How to Decide When to Get in the Weeds

I’ve been having trouble even starting to write about this topic because it’s such an interesting topic and something I’ve learned quite a bit about over the years — and continue to grow and learn about as I take on new teams!

As I’ve advanced in my career, I’ve gone from feeling like I need to learn every new technology or programming language (and getting overwhelmed and feeling inferior by the impossible feat) to realizing it’s impossible to know everything well. In the spirit of ruthless prioritization, I have to prioritize what it is I choose to know deeply (where I get in the weeds) and what I choose to only know at a surface level (usually relying on or deferring to the expertise of someone else who is in the weeds).

This approach to staying on the surface works really well when you can to defer to a colleague who you respect as an expert on their work (e.g. I understand we use XYZ technology but for any additional detail, talk to my colleague Jane in Engineering). And often times, a colleague will see this for what it is: trust that you will mind your own business because they’ve got their area under control!

It gets much more difficult when you need to do this with people who might report directly into you. Stay at surface and don’t know enough about their work? You seem out of touch (and isn’t it their job to “manage up” anyway?). Get in the weeds about everything they are working on? Now you are the dreaded micro-manager.

So how do you decide when to go deeper? There are tactics I’ve employed over the years that can help.

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Flavors of Agile

Many years into my career in software development, I was introduced to the concept of “agility” and specifically leveraging the “scrum” methodology. We were trained up over the course of a couple of days which included silly activities to prove a point like making paper boats. I learned about 2 week sprints, sprint ceremonies (like sprint planning, daily stand-up and retrospectives), and best practices around estimation.

At the time, I was on a very lean team responsible for operating a platform that was licensed to a competitor for what I understood was a large sum of money. Our product was important to the bottom-line so consistently delivering value was the name of the game. I enjoyed the structure that sprinting offered and the constant tangible value delivery to our customer appealed to the dopamine receptors in my brain that get excited when I check something off my “to do” list.

During that time, I also learned about the “agile manifesto” and that there was a real career path for people like me who enjoyed solving human-centered problems. And since then, I’ve worked with a number of different large enterprises that employ various flavors of agile.

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Unwritten Rules of Management: Managing Up

A while back, I worked for a leader whose management style I didn’t understand or appreciate until years later. I perceived his tactics as borderline micromanagement and I didn’t like the way he publicly challenged the team.

At the time, my direct manager gave me some tips for how to best manage the situation, especially given my future success at the company would depend on his blessing. In reflecting back on that time, I realize my manager had given me the gift of learning how to “manage up.”

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Unwritten Rules of Management: Air Cover

Recently I was discussing something fairly innocuous with a member of my team. Given there was a very small financial outlay for what I was planning, I mentioned I’d take it up with our manager just to confirm it’s not a big deal.

At that moment my direct report joked, “You can just do it and if anyone bristles, you can blame me.” I told him the first “rule” of being a decent manager is to not throw your team under the bus!

And this got me thinking that there are so many of these unwritten rules that I should share given it took me over 15 years of work experience to learn them!

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Transitioning from Peer to Manager

Early on in my career, I was given the opportunity for a promotion to lead the team I was on; this meant becoming senior to folks who had been my peers. While I was appreciative of the opportunity and others recognized my work ethic merited the offer, no one prepared me for the awkwardness of this transition. So. Very. Awkward.

Recently, I was approached by someone going through a similar transition and wanted some of my advice. I am sure I’m not the first to give this kind of advice and, obviously, your mileage may vary, but there are some basics that everyone going through this kind of thing should know.

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Gifting at Work: How Do You Handle the Holidays?

The holidays seem to be filled with societal pressures that push us toward consumerism. That said, there’s something really nice about receiving a gift, especially when it comes from a source you don’t usually expect: work!

There are some unspoken rules and general best practices to keep in mind to navigate this appropriately in most situations.

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What Do People Say When You Aren’t in the Room?

Recently, I was in a meeting where I mentioned that we’d need to recruit someone to help test. When I mentioned a particular colleague’s name, everyone’s faces lit up; she’d be the perfect person to help on this effort! This reminded me of something that is so simple but yet alludes many when it comes to work: if half the battle is showing up, the other half is how you show up.

But what exactly does that mean?

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Evaluating a Job Offer: How to Assess Culture Fit?

Recently, I was asked about how to assess the culture of a new organization before you join. As I mentioned in a prior post, it’s really hard to figure out whether you are joining a place where you’ll thrive and grow or if you are joining an organization with a toxic culture.

Here are some tips I use and recommend when assessing a potential company to work for.
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When to Say Goodbye: Do You Need to Stay 2 Years at Every Job?

A former colleague reached out to me earlier this year with a situation. She found herself in a position at a company that didn’t quite measure up to her expectations in terms of work/life balance and culture. It’s really hard to assess these things upfront and especially difficult for folks early in their careers with less ability / means to be choosy when job hunting.

Her question for me was: do I really need to stay at this position for 2 years to make this look good on my resume? Or can I start looking for a new position now?

My response to this question is nuanced because life isn’t quite so black and white.
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