My girlfriend and I are in the process of buying a house just north of San Francisco. Over the last six weeks, I’ve spent 500 hours immersing myself in real estate.

I’ve scoured the property, met with County officials, received bids from seven different contractors and conducted inspections with engineers, architects, roofers, plumbers, electricians, and pool servicemen.

This recent immersion into real estate isn’t only a personal rabbit hole; it has highlighted a larger problem that we’re all about to face. When rapidly accelerating technology meets slow-moving bureaucracy, the inevitable result is chaos. We urgently need a better way forward.

Accelerated learning through AI

The single most important tool for my learning about real estate has been AI – ChatGPT, Perplexity, Gemini, and others. I use ChatGPT “Deep Research” a dozen times a day to learn about random factors like the cost of rebuilding a private lane or how sound travels across marsh wetlands.

Of course, AI occasionally hallucinates. But even if 5% of what it provides is incorrect, these tools have exponentially accelerated my learning.

Despite my rapid learning and progress, all that speed hits a wall when confronted with real estate bureaucracy. Throughout this process, I’ve been confronted by an antiquated, bureaucratic, and slow-moving system.

BWOP – Building without a permit

One of the many challenges with our current property is that more than half of the house was built without a permit – BWOP. It’s as entertaining to say as it is painful to remedy!

To remedy BWOP, you either have to pay fines, retroactively obtain permits, and bring everything up to code, or demolish all of the work that was done! Unfortunately, this makes sense: without consequences, nobody would bother with permits.

Even more confusing is the fact that county officials can’t tell me exactly what qualifies for a BWOP. When you own a home, a certain amount of “exploratory work” is fine. But past a certain point, home improvements require a permit – and extensive fines if you’re caught out.

How much home improvement can be conducted without a permit? Nobody can tell me.

The rate of change is accelerating

It is onerous and time-consuming to navigate the complex bureaucracy even to answer simple questions. Meanwhile, my AI agents allow me to research more and play out more scenarios than if I had a full-time PhD-trained research assistant doing the same work.

As the authors of Responsive.org wrote back in 2015, “The rate of change continues to accelerate” and “The future is increasingly hard to predict.”

What do we get when we mix the bureaucracy of generations of humans overlapping their systems with technological innovation that is progressing more rapidly than thought? Uncertainty, and chaos. This is echoed on a global scale.

Just this week, the Trump Administration applied sweeping tariffs on every US trading partner, the stock and bond market plummeted, and days later the tariffs were reversed.

Tilting at windmills

When faced with rigid bureaucracy, most of us react with frustration – for the most part ineffectively. We complain that the “system is out to get us” or that real estate policy “just shouldn’t be this way.”

And while I agree that many of these systems we need are broken, this “tilting at windmills” – purposelessly attacking something that a single person can’t change – is worse than useless.

It generates more anger and frustration.

What we need to do, instead, is work where we can. In real estate, that means accelerating my learning and communication as much as technology allows, while still talking to humans and slowly working my way through the tangled bureaucracy until I can understand what will be required.

The way forward

The collision between AI acceleration and human inertia isn’t going away. So we have a choice: proactively design responsive systems, or continue stumbling through chaos. And this friction isn’t unique to real estate. It is symptomatic of a much broader issue affecting industries and institutions everywhere.

My only advice is to consider where in your life or business you can blend technology with the patient navigation of bureaucracy.

Instead of fighting unwinnable battles, our solutions need to be incremental. Learn faster, then communicate clearly, persistently, and compassionately with the slow-moving human systems we all depend on.

For many years now, I’ve repeated a phrase to myself: “Fear is my north star.”

Fear is often misunderstood as a negative emotion – as something to be avoided. Instead, it is a useful guide for action.

Some of the most significant moments in my life came as a result of moving towards fear.

I’m currently at one of those crossroads in my life, so in today’s Snafu article I’ll spell out my approach to fear.

The fear of opening Robin’s Cafe

I will never forget a pivotal moment in April 2016 outside of what became Robin’s Cafe.

I was on the phone with my friend Ronda, discussing all the reasons why opening my little restaurant might be a bad idea.

Ronda asked me a question that has guided me ever since: “Robin, is there any reason not to open up Robin’s Cafe besides your fear?”

I paused for a moment, answered definitively “no,” and from that moment was committed.

What fear has to teach

Fear is one of those topics that we think we understand, but most of us never study. We see someone doing an act of bravery – a firefighter running into a burning building or
Alex Honnold freeclimbing El Capitan – and call that courageous.

But what do those things have to do with our day-to-day, and what is fear even for?

Fear is a signal that something important is going on. That’s it. It is a spotlight that focuses attention on a moment, a decision or a significant act.

When we attend to that fear, and examine it instead of running away from it, we give ourselves the opportunity to accomplish something more.

Fear as a compass

There’s another kind of fear worth mentioning: fear of true danger.

If I were to try to free climb El Capitan, I’d be terrified. I’m an experienced mountaineer, but have zero experience free climbing technical routes. About ten feet up, I’d be sweating.

Inexperience or fear of the unknown – even a child’s fear of the “monsters under the bed” – might fall into this category.

But that’s different from informed, and constructive fear – fear that comes from uncertainty and vulnerability, which can serve as a guide.

Whenever I feel fear about something that isn’t imminently life-threatening – starting a business, making a big investment, or entering a new relationship – that’s a sign that I’m on the right track.

The fear of buying a house

I’m at another crux right now. Last week my girlfriend and I signed and put earnest money down on a house just north of San Francisco.

The house is a “fixer,” being sold by a bank because the previous owner died. We’ll need to do substantial work just to make it habitable.

We’ve run the numbers, paid thousands of dollars to have it inspected, and I’m in a moment of trying to decide if there are enough reasons not to buy the house, or if I’m just afraid.

How to use fear as your north star

Here are some useful tools in assessing fear that I’ve found myself using a lot in the last few weeks.

Name your fear

In real estate, I’ve been listing all of the potential outcomes that I’m afraid of. Seeing them written out on a page makes the fear more tangible.

Assess your fear

In business and now in real estate, I try to plan for the worst case scenarios.

What would happen if the housing market crashed? If we needed a new roof? If we couldn’t cover our mortgage?

It’s easy to be positive and hopeful about things going well. Planning for the absolute worst-case scenarios helps alleviate potential negative outcomes if the worst does happen.

Take small, incremental steps towards your fear

We’ve run countless competitive market analyses for this neighborhood. I’ve had five roofers out to inspect our roof and provide quotes. I’ve crawled through all of the attics to inspect the insulation.

Each of these was a single, small step towards a specific fear.

Courage is action despite fear

I define courage as action in the face of fear.

When I opened Robin’s Cafe, I was afraid, but I had outlined all of the potential downsides I could think of. I don’t know what will happen with our housing purchase. We may not get it, and we may decide to walk away.

But I do know that facing this fear – assessing it directly, breaking down the component pieces, and taking small steps – is a victory in itself.

Fear isn’t something to avoid. It is a compass pointing you towards your growth edges and where you need to go.

Last week, I hit an inflection point – a shift in perspective that altered how I see AI, and will shape everything I do going forward.

My history with tech waves

I came of age amidst the rise of the internet and social media.

In middle school I was on AIM chat rooms. (Don’t tell my parents, but I regularly snuck into the “mature” chat rooms when nobody was watching.)

Facebook arrived on my college campus during freshman year. I joined right away, but was hesitant to share my face online.

In 2007, when a college friend showed me his first iPhone, I was skeptical. It didn’t have a keyboard and felt flimsy in my hand.

When I moved to San Francisco in 2008, the world was reeling from the real estate crash. An industry that I’d been told my entire life was stable, bedrock, had dropped precipitously.

When I was training gymnastics at Stanford University in 2012, several of the guys I practiced with were in crypto and tried to encourage me to buy. I’ve since seen three crypto boom and bust cycles.

Pattern recognition

I started Responsive Conference out of my own desire to explore the future of work, and many of these trends.

I’ve met world experts on trends that became commonplace just a few years later – remote and distributed work, diversity & inclusion, blockchain, and more.

We talked about AI on stage back in 2019! But something is different now.

Casual early adoption

I’ve been using AI in my daily work for several years.

Ten years ago in video you had to manually transcribe an interview before editing. Now our transcriptions at Zander Media can be done in seconds.

I ask ChatGPT to review my articles for structure, grammar, and semantics. I nearly always search on ChatGPT instead of Google.

I’ve known AI is important, but not taken it more seriously than I did the rise of blockchain and crypto, social media, or even AOL chatrooms.

My philosophy has been that of a casual early adopter, “Oh, look! The world’s changed again. And I still need to go train my handstands.”

This one is different

Last week, I hit an inflection point, which happened for two reasons.

My girlfriend is a data scientist and through her daily work she already knows that AI is a tectonic shift.

Then, I listened to this conversation with Tyler Cowen, which I highlighted in Snafu last week.

In the interview, Tyler talked about the significance of AI, the differences between the major LLMs, and how he uses each of them. I was struck by how much I didn’t know.

I was chatting with my father over the weekend, and casually mentioned that AI was going to be the next electricity. He said, reservedly, that he might agree. I’ve since come to believe that AI represents the biggest disruption any of us have ever witnessed.

Bigger than the printing press

I believe AI is going to be bigger than social media, the internet, electricity, or the printing press.

A basic premise of Responsive.org is that the rate of change is accelerating. But just like humans aren’t very good at understanding compound interest or logarithmic growth, we aren’t good at comprehending what it means when a growth curve goes nearly straight up.

I’m not an engineer. I don’t understand machine learning, deep learning, or the math behind LLMs. And I’ve never been caught up in a hype cycle before. I wasn’t all-in on social media, even though I was there at the beginning, or crypto, even though I knew people who were.

But as a lifelong lover of books, I’ve always said that I wished I was there for the advent of the printing press. This is that moment.

My commitment

In a world that is on the verge of disaster – climate, socio-political unrest, and more – AI has the potential to be the collaborator we need to solve these issues. Equally, these tools have the potential to manipulate and destroy us.

My new commitment is to use these tools every day. In my current research of real estate, I’ve 10x my rate of learning by treating ChatGPT as a thought partner. While everything I write in Snafu will continue to be my own, I’m using these tools to hone my craft.

At Responsive Conference, people have been talking about AI on stage since 2019. But in 2025 I want to give attendees a direct taste of these tools as part of the conference experience.

We’re at the beginning of a new era. One that has the potential to be both awe-inspiring and terrifying. We’re not just building new tools – we’re building something smarter than ourselves.

How do we want to participate? How do we reinvent ourselves even faster than the tools that are learning from us? That remains for all of us to decide.

Three weeks ago, my girlfriend and I were looking at rentals just south of San Francisco. Over the course of a long afternoon, we looked at seven different properties.

The next evening, she messaged me a new Zillow listing – this time for a property for sale.

I walked over and wrote her a note: “Fuck it, let’s buy!”

What followed were weeks of going deep down a new rabbit hole. I spoke to hundreds of people, interviewed friends and family about real estate, and we put in four offers on a house.

The world is too loud

In a world rife with distraction, falling down a new rabbit hole isn’t always escapism. Sometimes it’s how we survive.

The allure of breaking news, the infinite scroll of a social feed… Amidst the chaos of modern life, the ability to go deep – to immerse yourself completely in something new – isn’t just useful. It can be a source of sanity.

The sanity of obsession

When the world is chaotic, most of us turn to distraction – even when those distractions leave us feeling worse.

Early in the COVID-19 pandemic, I watched some of the Netflix Documentary Tiger King. While it was a welcome distraction, I came away feeling buzzed and empty.

By contrast, a true rabbit hole – one with structure, challenge, and stakes – isn’t escapism.

My world view changed when I walked into a gymnastics gym at 17 years old and began to learn gymnastics. That rabbit hole has consumed me ever since. Similarly, when I studied ballet obsessively for a year, founded Responsive Conference to study the future of work, or started Zander Media to practice storytelling.

Deep learning is a way to regain control over your attention and expand your world view.

Learning is often conflated with speed, with getting more done in less time. I have studied speed reading, memory palace memorization, and other learning “hacks,” but what interests me more is depth, breadth, and languor.

But my goal with real estate wasn’t just speed. It was depth. Amidst the chaos of the world, it was restorative to spend a few hundred hours researching with ChatGPT, calling dozens of realtors and brokers, interviewing friends, and immersing myself in a new discipline.

Finding your rabbit hole…

Here are three questions I’ve been finding it useful to consider when embarking on a new learning journey.

Why this?

My girlfriend and I were ready to buy our first home. There was a specific house that we were interested in. And, as a friend said to us, “You have to live somewhere.”

Why are you studying this domain right now? That will guide your rabbit hole learning journey.

Why now?

With real estate, we had a very clear rationale.

There were several options available to us – including renting for a year, a short term rental, or finding a house very near term that we wanted to buy.

Why are you interested in doing this journey, and why now?

What’s your deadline?

I’m a proponent of external deadlines. Without deadlines, I will put off until next month something that I could equally accomplish this afternoon.

But when I have a deadline – a person I’m accountable to, a place that I want to live – I’m capable of more than I’d previously have thought possible.

Why rabbit holes matter

The world is chaotic. There’s more distraction and noise on the front page of any news outlet or social media platform than any of us should be consuming.

Deep learning forces us to focus on depth – on something that actually matters. And in a world that’s only getting noisier, that kind of focus is how we stay sane.

I was at dinner with my parents and my girlfriend last weekend. For some reason, Robin’s Cafe came up in conversation.

Anyway, I got on my soap box and said: “I opened Robin’s Cafe on 3 weeks notice and…” Before I could finish the sentence, my father said “And you sold it on Craigslist. We know! We’ve all heard that story many times before.”

My girlfriend, who has recently been subjected to me repeating the story on Zoom calls many times a day, doubled over laughing.

I’m proud of having started and sold Robin’s Cafe. But that also happened nine and five years ago, respectively. I’ve lived through several life changing experiences since then. Relationships and breakups, a car crash, the death of a family member, my best friend’s cancer, and a couple new businesses.

But because Robin’s Cafe was a formative experience – and doubtless because I’ve told the story a few too many times – that narrative has become part of my identity.

We don’t talk enough about identity

Identity isn’t fixed. It is malleable. Our “residual self-image,” to quote The Matrix, should change and adapt over time.

When big life experiences happen, those moments shape us. As they should! But it is up to us to decide for how long and to what extent we want to refer to them forever after.

When she laughed

When my girlfriend burst out laughing (and, to be fair, we’ve both been laughing about that moment ever since), I was forced to reconsider the story and the identity I’ve tied to it.

I’ve reiterated it so many times now that it’s become ossified. And instead of tackling something new, I’m referencing something that took place nearly a decade ago.

Because my girlfriend loves me, her laughter allowed me to laugh at myself. At the ridiculousness of continuing to reference something that, in my life, might as well be ancient history. Her laughter allowed me to see myself through a new perspective and shake up a longstanding identity – that of the person who did those things.

Hold fewer identities

One of my goals in life is to remain resilient. And one of the best ways to maintain resilience is to hold fewer identities, and hold them loosely.

We all know a former high school athlete who recalls their peak performance on the high school football team instead of going to gym today. Or the political stickler who can’t see a perspective other than their own.

I’m an athlete, a son, a partner, a dog dad, and an entrepreneur. And, apparently, I used to be a coffee shop owner.

Moving beyond Robin’s Cafe

Of course, I’ll reference Robin’s Cafe again. I’ll probably even tell the story of opening and selling it to someone new. But my Dad’s joke, which landed so poignantly because of my girlfriend’s good humor, highlighted that I still hold that specific identity too firmly.

It’s time to let it go, so that I can go and do something new.