Idea!!!

Winning Ourselves to Death? AI, Finite Thinking, and the Urgent Quest for an Infinite Game

There are at least two kinds of games. One could be called finite, the other infinite. A finite game is played for the purpose of winning. An infinite game for the purpose of continuing the play.” — James P. Carse

Most of us are wired to win. We chase victories in our jobs, in the market, in elections, even in the fleeting dopamine hits of social media likes. The scoreboard, in its many forms, can become a kind of scripture. But here’s a thought that might keep you up at night: what if this relentless instinct to win is the very thing that threatens to end the game entirely?

This isn’t just some philosophical chin-stroking. It’s rapidly becoming a survival question – for our systems, our societies, and, increasingly, for the very machines we’re building. The nature of the game has shifted. And so, disturbingly, have some of the players.

Finite vs. Infinite: What Game Are We Actually In?

Let’s get Carse’s distinction clear. Finite games are familiar: they have set rules, known players, clear winners and losers, and a definitive endpoint. Think of a football match, a game of chess, or the quarterly earnings report. Someone triumphs, the whistle blows, the books close.

Infinite games, however, evolve as they’re played. The primary goal isn’t to achieve a final victory, but to ensure the game itself continues. Think of science, democracy, or the grand, messy project of civilization. There’s no “winning” science; there’s only advancing understanding. You don’t “win” democracy; you work to perpetuate it.

The tragedy of our modern moment? We’re caught playing finite games within inherently infinite contexts. When companies sacrifice long-term trust for a fleeting quarterly gain, or when political actors torch foundational institutions for a viral soundbite, they’re mistaking a single checkpoint for the finish line. They’re playing by the wrong rulebook.

Finite players obsessively ask, “How do I win this round?” Infinite players ponder, “How do we ensure the game can continue for everyone?”

The Seduction of the Short Game (And Why It Feels So Rational)

Now, let’s be clear: short-term thinking isn’t always born of malice or stupidity. Sometimes, it’s a perfectly rational response to a game that feels rigged or broken.

  • If the market seems fundamentally unfair, cashing out early feels smart.
  • If societal trust is cratering, an “every person for themselves” mentality becomes a grimly logical defense.
  • If the future looks bleak, why bother planning for it?

This is classic game theory playing out in a low-trust environment. In the Prisoner’s Dilemma, defection becomes the dominant strategy when faith in the other player evaporates and the “shadow of the future” – the expectation of future interactions – disappears.

Short-termism, then, isn’t the disease itself. It’s a glaring symptom of collapsing infinite games.

Enter the Machine: When AI Sits Down at the Table

Artificial intelligence and automation aren’t just faster, more efficient players; they are fundamentally different kinds of players. And this changes everything.

  1. AI Doesn’t Bluff, Forgive, or Flinch (or Care About Your Feelings) AI, in its current iterations, doesn’t pursue a legacy. It has no concept of dignity, honor, or empathy. It plays the game it’s programmed for – and it plays it with an unyielding focus on the defined “win” condition.
    • AI doesn’t pause to question the ethics of the rules.
    • AI won’t hesitate to exploit any loophole, no matter how damaging to the spirit of the game.
    • AI doesn’t offer mercy, grace, or a “Kumbaya” moment. Its internal query isn’t, “Should this game continue for the good of all?” It’s, “Am I optimizing for my programmed objective?”
  2. Automation: Making Finite Thinking Scalable and Frighteningly Efficient Automation acts as a massive amplifier for extractive, finite logic:
    • Recommendation algorithms optimize for immediate engagement, not nuanced truth or long-term well-being.
    • Hiring models, trained on past data, can maximize conformity, not spark innovation through diversity.
    • Predictive policing systems prioritize statistical efficiency, potentially at the dire cost of justice and community trust.

We’ve inadvertently engineered a terrifying feedback loop of optimized short-termism. As one astute observer might put it: an AI trained solely on short-term KPIs is a sociopath with a perfect memory and infinite patience.

Game theory was originally built to model human (ir)rationality. But what happens when non-human intelligence, operating without human biases or biological limits, enters the arena?

  • It never forgets a slight or a strategy.
  • It doesn’t fear punishment in any human sense.
  • It can simulate billions of strategic iterations in the blink of an eye.

In a world increasingly populated by these synthetic actors:

  • Reputation can become mere lines of code, easily manipulated or faked.
  • Strategy devolves into pure, cold mathematics.
  • Cooperation, if not explicitly incentivized as a primary objective, becomes a rounding error. Even elegant cooperative strategies like “Tit-for-Tat” begin to break down when your opponent never sleeps, never errs, and never has a crisis of conscience.

We evolved playing games for survival. Now, we’re in a meta-game against machines we ourselves built to win, often without deeply considering the implications of their victory.

The Human Predicament: Stuck in Finite Loops, Designing Even Faster Dead Ends

So here we are: humans, often trapped in our own finite feedback loops, now designing AI that plays even shorter, more ruthlessly optimized games.

  • Markets risk becoming zero-sum speedruns, where milliseconds dictate fortunes.
  • Politics can collapse into frenetic meme cycles, devoid of substance.
  • Even human relationships risk decaying into transactional exchanges, evaluated for immediate payoff.

And here’s the rub: trust is built slowly, painstakingly. AI operates at lightning speed. We are, in essence, optimizing ourselves out of the very qualities that sustain infinite games: grace, forgiveness, moral memory, and the capacity for uncalculated goodwill.

In a world increasingly mediated by machines, perhaps the most radical, most human act is to consciously, stubbornly, choose to play the long game.

Designing for Continuity: The New Meta-Game We Must Master

If we want to navigate this profound transition without engineering our own obsolescence, we need to fundamentally redesign the games we play and the systems that enforce them.

  1. Weave the Infinite into Our Digital DNA: We must demand and build multi-objective AI – systems that explicitly reward cooperation, sustainability, and the flourishing of the game itself, not just narrow, easily measurable wins like clicks or conversions. Incentivize co-play and robust reputation, not just digital conquest.
  2. Engineer Trust, Don’t Just Preach It: Talk is cheap. We need systems that foster trust by design. Think decentralized identity protocols, verifiable credentials, and transparent auditing of incentives right down to the protocol layer.
  3. Redefine What ‘Winning’ Even Means: It’s time for a profound shift in our metrics of success:
    • From short-term ROI to long-term Return on Relationship.
    • From market domination to societal durability.
    • From Minimum Viable Products to Multi-Generational Visions.

Remember, the most valuable asset in any infinite game is a player who is committed to keeping the game going.

The Infinite Game Is a Choice, Not a Foregone Conclusion

AI doesn’t inherently care about meaning, purpose, or the continuation of the human experiment. That, my friends, is squarely on us.

We are the current custodians of the truly infinite games: democracy, societal trust, love, ecological balance. These cannot be “optimized” into oblivion. They can only be nurtured, protected, and adapted.

So, the next time you’re faced with a decision, a strategy, a temptation to score a quick “win,” pause and ask yourself:

  • What game am I really in right now?
  • Who wrote these rules, and do they serve the continuation of play?
  • Will this move, this choice, this action, keep the game alive and healthy for others, for the future?

The future doesn’t belong to those who simply master the current round. It belongs to those who understand that the end of a round is never the end of the game.

These are the questions I find myself wrestling with. What are yours? The game, after all, continues. And how we choose to play next might make all the difference.

Idea!!! · venture capital

The 5 Dangers To Scale In Emerging Markets

Every industry has its jargon. In venture capital, there’s traction, scale, product market fit, etc. The problem with jargon in venture capital is it’s purposely elusive and nebulous.

The core of private equity markets is information arbitrage. There’s information asymmetry between capital and operators. As a result, different stakeholders create different definitions and everyone ends up talking past each other.

Why am I starting this conversation with jargon? It’s important we have a unified definition of what I mean by scale. Scale, from an operators and investment perspective, means I know what inputs I put in and I can predict my outputs/outcomes with reasonable certainty.

Emerging markets present unique challenges when it comes to scaling. They transcend business types and sectors. It makes scaling super challenging for emerging market companies and sometimes create zero-sum industry dynamics. This is why I’m launching a series on the 5 dangers of scaling in emerging markets and how to overcome them. The five dangers we’ll be diving into are:

  1. Customer distribution – Most of the time, market organization is one of the core challenges for companies. How do you organize your market in ways that are scalable and repeatable? Is repeatable important at this point?
  2. Customer education – While building/organizing a market, you might have to do more education to customers which might lead to higher acquisition costs. How do you teach customers but still keep your cac down?
  3. IC ramp up – how do you train people fast enough to execute on your behalf?
  4. Management / scaling operations – How do you create management expertise so your operations can scale with the market opportunity?
  5. Irrational Competition – How do you compete/navigate irrational competitors? what are irrational competitors?

Over the next couple of weeks – I’ll be diving deeper into these areas and exploring potential solutions.

#MentalNote · Idea!!! · Leadership

Getting Past No: A Non-Sales Person Guide To Objection Handling

If you’re doing life right, you hear no or get objections frequently. I had one of those days last week. I heard no/ objections to a lot of different projects, clients, and opportunities. Objections is easy to handle on a one off basis, but when you get an overload in a day, you’ve got to have a system or framework to help navigate objections in an effective and positive way.

I thought back to my early start-up days when I got a chance to work intimately with the sales team. I had the privilege to train under a sales genius who imparted a lot of sales wisdom and business experience on to me and the team. We didn’t have a pure sales training regiment, but I felt like everyday was an opportunity to learn from a well seasoned sales executive.

One of the lessons he taught our team early was on how to handle objections from prospects. Potential clients often say no for several reasons and a good sales professional has tools to identify their reasons for saying no and help the prospect get to yes. But most importantly, great sales professionals re-frame objection as an opportunity to learn more about the client and their needs.

We learned the L.A.E.R framework to manage our responses to objections. When we hear an objection from a prospect, we :

  • Listen– Take a step back and just listen to the prospect. Let them discuss their main concerns uninterrupted.
  • Acknowledge– Repeat back to them their concerns as you hear it. This helps to make sure you understand what they are saying but also they understand what they said during your conversation. Re stating a prospects objections also demonstrates you’re really listening to them and looking to seek a solution.
  • Explore– Most no’s or objections need to be unpacked. A great sales professional uses an objection to get to know more about the prospects needs and values. For example, a prospect might say your product offering is too expensive. What does that really mean? Is there a budget issue? Did you demonstrate and communicate the value your product/service provides? Asking more questions to understand their objections helps get past no’s and find new opportunities to help the prospect see the value in your product or service.
  • Respond– After identifying the objections, acknowledging their concerns, explored and unpacked the reasons for the objection, now you can finally respond with some recommendations. This may not always go in your favor. The main goal is help your prospect understand if the concerns you’ve discussed still exist and if so, what are the next step.

Overall, the L.A.E.R framework really helps to guide conversations with prospects during the sales cycle. It’s definitely applicable to any type of objection handling moments you’ll have personally and professionally. At the core of the L.A.E.R framework is need and a goal to understand and empathize with the prospect. Using L.A.E.R will help you get past objection and hopefully closer to yes.

Idea!!! · Self-Revelation

The Remedy for Impostor Syndrome: The Difference Between Amateurs and Professionals

I have stage 5 impostor syndrome. Most of us do in some part of our lives. It tends to show up more in my professional life. After doing some research I found out some interesting stuff… Looks like I’m not alone…..

The “Impostor Phenomenon” was first identified in the late 1970s by Pauline R. Clance and Suzanne A. Imes. Their researched showed that many high-achieving women tended to believe they were not intelligent and that they were over-evaluated by others.

People who have Impostor Syndrome “experience intense feelings that their achievements are undeserved and that they’re likely to be exposed as a fraud,” according to a report in the International Journal of Behavioral Science.

Psychologists first thought that Impostor Syndrome affected only professional women, but research has proved that men and women feel it equally. The profession you’re in doesn’t matter. It’s been found in college kids, academics, managers, and medical workers. Actual success doesn’t matter either.

According to the same report, “anyone can view themselves as an impostor if they fail to internalize their success.” ( Breena Keer,Why 70% of Millennials Have Impostor Syndrome, November,15, 2015)

A quick rundown of how impostor syndrome works. (Thanks Hustle). I’ve found discerning between amateurs and professionals can be helpful. Then, Farnam Street blessed my inbox with a post about that.

  • Amateurs stop when they achieve something. Professionals understand that the initial achievement is just the beginning.
  • Amateurs have a goal. Professionals have a process.
  • Amateurs think they are good at everything. Professionals understand their circles of competence.
  • Amateurs see feedback and coaching as someone criticizing them as a person. Professionals know they have weak spots and seek out thoughtful criticism.
  • Amateurs value isolated performance. Think about the receiver who catches the ball once on a difficult throw. Professionals value consistency. Can I catch the ball in the same situation 9 times out of 10?
  • Amateurs give up at the first sign of trouble and assume they’re failures. Professionals see failure as part of the path to growth and mastery.
  • Amateurs don’t have any idea what improves the odds of achieving good outcomes. Professionals do.
  • Amateurs show up to practice to have fun. Professionals realize that what happens in practice happens in games.
  • Amateurs focus on identifying their weaknesses and improving them. Professionals focus on their strengths and on finding people who are strong where they are weak.
  • Amateurs think knowledge is power. Professionals pass on wisdom and advice.
  • Amateurs focus on being right. Professionals focus on getting the best outcome.
  • Amateurs focus on first-level thinking. Professionals focus on second-level thinking.
  • Amateurs think good outcomes are the result of their brilliance. Professionals understand when outcomes are the result of luck.
  • Amateurs focus on the short term. Professionals focus on the long term.
  • Amateurs focus on tearing other people down. Professionals focus on making everyone better.
  • Amateurs make decisions in committees so there is no one person responsible if things go wrong. Professionals make decisions as individuals and accept responsibility.
  • Amateurs blame others. Professionals accept responsibility.
  • Amateurs show up inconsistently. Professionals show up every day.

It comes down to celebrating all successes big and small.  Understanding that all my successes are connected to a core set of capabilities and skills that allow for long term success. Having a bigger picture view of my capabilities and achievements will help put my impostor syndrome in check.

Idea!!! · Self-Revelation

Blog it out
Blog=ideas+soapbox+ accountability

After a summer long hiatus, I’m back! I started business school in DC and now I’m on the grad school grind. I’m really going to do it this time! I’m really going to keep up with this blog or die trying. Keep me accountable people.