Category: Random

Last month, I bought a house.

Buying a house is more complicated than nearly anything else I’ve done – besides, perhaps, running a business.

Over the last few weeks, I’ve highlighted some of my most popular articles from the last two years. In doing so, I realized that many of my personal favorites are those I reference repeatedly; they’re evergreen.

But over the course of the eight months leading up to the purchase, I learned a lot. So today I’m sharing the article I wish I’d been able to read when I started.

This is not an argument for or against buying a house. If you want to be talked out of buying a house, read Ramit Sethi. If you want to hear reasons to buy a house, ask a Boomer.

Instead, this is what I wish I’d known about house buying when we got started back in February.

I’ve seen a lot of backward industries:

• I’ve worked in large non-profit arts organizations.
• I’ve worked within family-owned SMBs.
• I had a chef throw a plate at my head in a restaurant.
• I’ve worked in fast-paced, drama-filled tech companies.
• I’ve obtained a myriad of impossible-to-get permits at Robin’s Cafe. San Francisco doesn’t make brick-and-mortar permits easy.

So believe me when I say that I’ve never met as backward, corrupt, and intentionally complicated an industry as real estate. First, let’s define some terms.

The people you’ll meet:

• Buyer – That’s you!
• Seller – The current owner of a property.
• Agent – Agents work for either the seller or the buyer – but actually they work for themselves. Their goal is to get you to buy or sell a house, and serve as a liaison between you (the buyer), the seller’s agent, and the seller. Agents aren’t financially motivated to help you get the best deal because their commission is a percentage of the price of your house. A small price reduction barely affects their fee, even though it matters a lot to you. You are not legally required to have an agent in most states.
• Mortgage broker – These folks help find your mortgage – assuming you aren’t paying all cash. They’re very salesy and eventually sell your mortgage to someone else. The benefit is that they’re available all hours and can get you information very quickly.

The companies you’ll work with:

• Real estate brokerage – Agents work within brokerages, and split income, usually 50/50, with an agent. Brokerages also list houses for sale. There are small, boutique brokerages and also national chains like Compass and Coldwell Banker.
• Mortgage company – The company that ultimately holds your mortgage. If you get a mortgage with a specific bank or credit union, they’re not likely to sell your mortgage to a third party.
• Title company – The company that ensures successful transfer of ownership between the buyer and seller.

The terms you’ll hear:

• Buyer’s agent vs. listing agent – Typically, the Buyer and Seller each have an agent, and agents discourage you from communicating directly with the other party because it keeps them as the middleman.
• Pre-approval vs. pre-qualification – These are terms you’ll hear from your mortgage broker, and represent whether you are qualified for a mortgage. Pre-qual is a soft estimate of how much you’ll be able to borrow. Pre-approval is documented and stronger.
• Foreclosure – When a bank is selling the property, instead of a person. Not for the faint of heart.
• In contract – An agreement between buyer and seller that the buyer will purchase the real estate, assuming specific conditions are met
• Earnest money – Money you put down (usually 3%) to show proof that you are serious about buying a specific property
• Contingencies – The requirements that need to be met before you buy.

Our adventure started in February of 2025. My then-girlfriend and I were planning on renting, when – seemingly out of the blue – she texted me a house for sale. A house we saw that weekend – a dilapidated mansion with spectacular views – became the focus for my learning for the next five months.

The mansion had a lot going for it – great views, extremely quiet, an abundance of indoor and outdoor space, pool, garden, easy rental opportunities, and more.

It was also a completely ridiculous project. It had been a party house, built in the 1970s and then illegally rebuilt, which, we later learned, triggered county requirements like seismic retrofitting and a sprinkler system. There were three levels of decks with incredible views, but they had been poorly built and were on the verge of collapsing. We discovered two nests of bees in the walls – so active in the spring that the buzzing could be heard inside the house!

After five months of research and seven offers on the property, we walked away. More than the repair and reconstruction required, we walked away because of the county requirements. The onus on a new owner to make up for the previous decades of illegal construction was too high.

We bought another house in the same city, which also has views, a pool, and rental opportunities. Our new house isn’t a mansion, and needs only modest repairs – and we’re very happy here. But I learned more about real estate during this months-long sprint than I ever thought possible.

These are some of my biggest takeaways.

Mindset

1. Don’t fall in love until after you buy

It’s really helpful if you don’t fall in love with a single property until after you own it. This is the single biggest purchase most people will ever make, and the decision is usually made emotionally. Instead, try not to get too excited until after you’ve purchased. Obviously, you don’t want regret. Make sure you like the house you’re about to buy! But too often people fall in love and then get into a bidding war out of the desire to win a deal.

2. An entrepreneur’s mindset

The thing that helped me the most through my real estate learning journey was what I’ll call an entrepreneur’s mindset.

We wanted a home, yes. But I also didn’t want to lose money on a project – if anything, I wanted to make money.

Know how to protect your downside and plan for contingencies in case things go wrong.

If your circumstances change and you can no longer afford your mortgage, what are you going to do? What are the ways this property could cash flow, even if you weren’t living in it? Are there cosmetic repairs you could make that would improve the value of your home?

3. They treat you like the product, but actually you have all the power

I’m fascinated by how different industries talk about their customers. At Robin’s Cafe, we had diners. At Zander Media, we have clients. At Responsive Conference, we have attendees. Facebook, OpenAI and most software companies have “users” – which is the same term that drug dealers use to describe their customers.

In real estate, agents call real estate “inventory” and us, the clients, are called “buyers.”

There’s a sense as you begin to get serious about a property that you are a cog in the machine. Agents will push you to bid on a specific property. Mortgage brokers request that you sign before you’re ready.

The most important thing to remember is that you hold all the power. As the buyer, you can walk away at any time. (Though if you wait too long and contingencies are past, you stand the risk of losing your earnest money.)

You always have the power to walk away.

Research

4. Know what you want

We had lots of criteria starting out:

• We wanted a house that was not too far from San Francisco
• That was safe
• And that we could afford
• We wanted within walking distance from an interesting town
• Ideally we wanted open space nearby
• The house should have rental opportunities
• And best case scenario for it to have a pool
• Weirdly, we both had a thing for double front doors just because that felt fancy

However big or small, list out the criteria you want in a house. You’ll have to settle on some of them, but the clearer you can be on what you want, the more likely you are to get it.

5. See lots of houses

The best way to learn about houses is to see lots of houses. Agents are great for this – but don’t commit to working with one agent for a long time, or maybe ever. You can call the listing agent – the person who is showing the house – and ask to see it. I prefer not going to Open Houses because there are other people and a (false) sense of urgency. Even driving by houses for sale is useful to get a sense of regions and neighborhoods

6. Do your research

In this industry more than anything else I’ve ever experienced, it’s essential to do the research. The more thoroughly you get to know a specific region, neighborhood, and even a specific street, before you decide which house to buy, the better off you’ll be. Use ChatGPT to do Deep Research on a variety of topics related to things you see in each house you visit. Ask real estate agents a lot of questions. Talk to people on the street.

7. Get lots of (free) quotes

I’m surprised that home buyers don’t visit homes they are seriously considering with an entourage of contractors, plumbers and electricians.

There are two different types of quotes – those you pay for and those you don’t. If you call a local HVAC company and request a pre-sale quote, they’ll charge you. But, instead, if you say that you are planning to buy this house and just want to plan for your future, they’ll likely come to the house, look around, and send you an estimate of costs.

A lot of the difference depends on whether they write up a multi-page summary of their findings or just a single page with a price. Either one works fine when it comes to negotiating down the price of the house.

But even if you did have to pay for every technician at every house you’re considering, those few hundred dollars would save you tens of thousands in having avoided bad decisions.

8. Talk to the city or county

One of the most under-leveraged aspects of real estate is talking to your local jurisdiction – the city or county within which your property falls. Even just the question “What’s this city/county like to work with?” which any agent or contractor should be able to answer, will help inform your decision about the amount of work you’re willing to tackle and the amount of bureaucracy you are willing to wade through.

The county where the mansion sits is quite a bit easier to work with than the city within which we now reside. But since our new house requires so much less renovation, we decided that trade-off was worth it.

Moreover, the city or county will have some amount of records about the property in their files and some people within the city/county may even be familiar with the property itself.

Talk to your local jurisdiction before you buy!

9. Read the fine print

I’m continually shocked that most people don’t read every bit of fine print in every document. The very first real estate agent who showed us a house requested that I sign an exclusive agreement with him even in order for him to show us the property. Had I not read the contract in advance, we would have been stuck with him without recourse.

The title company who transferred ownership of our new house from the previous owner to us was surprised that I requested the 250 pages of legal documentation in advance of the day of signing. And that we protested that they had only given us one hour to review the documents in person.

Is reading fine print and intentionally obscure legal language a difficult question? Yes, of course it is. And as you go into a hundred thousand dollar project, it is also a necessity.

Never, ever sign without reading the fine print.

Cautions

10. Everyone has something to teach you

Real estate, especially when you’re just starting out, is a matter of talking to a thousand people. And everybody has something to teach you.

In the last seven months, I’ve been on the roof of ten properties with at least a dozen different roofers. Every time I go up, I learn something new about roofs from a casual comment the roofer makes.

Talking to an abundance of people, even if you only learn one new thing from each, will enable you to make better decisions going forward.

11. A false sense of urgency

As with most forms of unethical selling, everyone will try to create for you a false sense of urgency. Agents will tell you to bid now. Mortgage bankers will tell you you have to sign today, or else deadlines won’t be met.

And it is true, especially in a competitive real estate market where time matters. But it rarely matters as much as the people you’re working with will have you believe.

Don’t get swept up in the adrenaline of the rush and lose sight that you are considering among the biggest purchases of your life.

12. Agents are out to get you

There are a lot of good people in the trades. But it has been my experience (and is widely agreed) that people who make their living in real estate – agents, brokers, mortgage brokers, etc. – are out to get you.

But of all of these, real estate agents are my least favorite.

I’m reminded of the Charlie Munger quote, “Show me the incentive and I’ll show you the outcome.” The money circulating around real estate is large. Most of us don’t otherwise handle transactions in the 100s of thousands of dollars. And when someone is compensated purely on a percentage basis of the cost of the home, their incentives are – at best – only loosely aligned with yours.

It’s hard, but not impossible, to buy houses in the United States without an agent. And how to choose an agent – or avoid getting one – is a longer topic than this article will allow. But know, going in, that “your agent” is not on your team.

13. Read How to Buy a Used Car (and then do that for houses)

Last week, I revisited my article, “How to Buy a Used Car.” There are a lot of similarities between buying a used car and buying a house.

14. Read Abundance (and know that’s not the world we live in)

Ezra Klein’s Abundance is a hopeful picture of what the world might look like if we were to build in the United States. And it isn’t the world we live in.

Instead we live in a world where the accelerated rate of change exists in stark contrast to the slow tedium of hundreds of years of bureaucratic process. Even as technology enables us to move and think faster than ever before in human history, the lethargy of governmental bureaucracy stagnates growth.

That’s how it is right now – unfortunately. Plan accordingly.

Conclusion

I’m thrilled with our new home, and the sensation of being a first-time home buyer. But perhaps even more importantly, I’m no longer overwhelmed by an industry that previously felt impenetrable, overwhelming, and ridiculously complex. Hopefully this article is a first step for you to achieve the same.

Last week’s Responsive Conference was the best event I’ve produced. Attendees have been raving about the experience, my team bonded in new ways, and I walked away without the post-conference crash that too often accompanies producing a big event.

One of the things we did especially well this year was to incorporate alternative event formats into the conference format. Specifically, there are three atypical formats that I think every event organizer should incorporate.

Fishbowl

A fishbowl is a panel with 1-3 additional seats on stage. Your audience is encouraged to sit in that seat and join the speakers in conversation.

Why this works:

Fishbowls challenge the audience to stay engaged. Every time there’s a new participant in the hot seat, the audience – even if they weren’t fully engaged before – has the opportunity to reengage with the conversation.

This format also adds variety for the speakers. Most panels fail because panelists talk to each other about pre-planned topics or things they know too well. Regularly adding new people to the conversation changes the dynamic with each new attendee.

Best-case scenarios:

A fishbowl can work with four seats on stage, where one seat is empty for participants. At its best, though, there are five or six seats available, of which two are available to participants or the facilitators.

This session can work in a fixed seating format, but it works even better when the audience is literally sitting around the speakers, while the speakers are facing each other in the middle. A literal fishbowl shape added to the intimacy of the experience for everyone involved.

Considerations:

You need a strong facilitator – The first consideration is that a strong facilitator has to set the context for this format and keep people moving in and out of the hot seat (or seats). This facilitator needs to describe how a fishbowl works and encourage attendees to join in. The facilitator can occupy one of the seats on stage throughout or facilitate from the side.

The audience needs to be engaged – a fishbowl only works if attendees participate. This requires the facilitator to encourage attendees to jump in. Some gentle facilitation may be required to make this happen.

The people on stage need to be engaged – this isn’t an issue for most speakers, but participant speakers should know that this won’t be a typical panel. Most speakers don’t want to phone in the experience – they want to enjoy the experience! But a fishbowl is not a panel, and some speakers may be hesitant.

Interview-in-the-Round

An interview-in-the-round is a session where each speaker interviews the next speaker. It works like this:

• Speaker 1 interviews Speaker 2
• Speaker 2 interviews Speaker 3
• Speaker 3 interviews Speaker 4
• Speaker 4 interviews Speaker 1

​Here’s an example from Responsive Conference 2019.

Why this works:

Attendees want to hear from the speakers. In this format, they get 15 minutes uninterrupted from each speaker (assuming a 60-minute session), with another 15 minutes where that speaker conducts an interview. Assuming good speakers, it is always a good experience for attendees.

Best case scenario:

Speakers have an intimate experience on stage, which then translates into the attendees’ experience of the session. Through intimate one-on-one interviews, they are able to go places that they wouldn’t in a larger group.

Considerations:

Unpredictable outcome – The “outcome” from an interview-in-the-round is unpredictable. There isn’t someone in charge of summarizing the experience for attendees, so event organizers might feel uncomfortable with the experience.

Speaker egos – The problem with this format comes down to speakers’ egos. It isn’t a common format compared to panels, and as a result, speakers feel like they won’t be able to get on stage as much as they expect to. This isn’t factual – in an interview-in-the-round, speakers generally get more stage time than in a typical 4-person panel. But from an appearance perspective, they often feel like they’ll get less limelight.

I’ve never seen attendees dislike this format, but speakers may have to be persuaded.

Unconferences

I define an unconference as any event where the attendees set the agenda. I’ve written a full article on how to run an unconference, so start there.

Why this works:

Unconferences work because there is always more collective intelligence in a group of attendees than in a single person on stage. An unconference makes use of that collective knowledge by allowing the attendees to determine the agenda.

Best case scenario:

The best-case scenario for an unconference is that it channels the focus of an entire group, and everyone walks away reenergized and with several new ideas.

Considerations:

The problem with an unconference by definition is that speakers and facilitators aren’t the highlight. This makes selling tickets against name-brand speakers and brands nearly impossible. An unconference can be a great experience for attendees, but it is much harder to monetize.

Gatherings and events are a competitive advantage in business, especially in an age of AI. Our loneliness epidemic and the enduring popularity of books like The Art of Gathering both demonstrate that humans want to gather in new, interesting, and immersive ways.

Any kind of gathering is better than not, but panels and happy hours need not be the only way we do so, and these three alternative formats provide some welcome variation.

The future is unpredictable

In 2015, the authors of Responsive.org wrote that “the future is becoming increasingly difficult to predict.” Today, with global instability, political partisanship, and a more rapid rate of change than ever before in human history, those words feel prescient.

The tension between organizations optimized for predictability and the unpredictable world we live in has reached a breaking point. Only organizations that adapt to this ever-changing world will survive.

We structure organizations the same way we did in decades and centuries past – built for a time when predictability mattered more than speed of execution.

I’ve had anything but a conventional career path. Across more than two dozen different industries – from circus acrobat to self-taught restaurateur – I’ve witnessed the same bureaucratic practices; the same good people stuck in outdated systems.

And nowhere is that unpredictability more obvious than in live events.

A few small fires

​Responsive Conference 2025 is next week. There have been a few small fires: a team member is in the hospital, a keynote speaker asking to change their call time, and nametags scheduled to arrive a week late.

A friend asked me recently if I was going to propose to my girlfriend on stage at the conference. My answer was – quite obviously – no. And not just because she wouldn’t want that kind of public attention.

Events are an act of service. Great events exist for their attendees, speakers – and only then for the organizing team. To take the spotlight with an engagement proposal defeats the purpose of producing an event. It takes the focus off of them and their experience. When the organizer takes up too much space, they undermine the service the event provides to the community.

The utility of community

On September 16th, the day before Responsive, my friend Jenny is producing the Conference for Conferences, a 1-day event about how to run more immersive and experiential events.

Then, Responsive Conference, which I often describe as a three-ring circus that we always design as an experiment in the very principles we gather to discuss.

Within the curation of Responsive Conference, too, there are sessions that address the intersection of community, change, and AI.

Suzy Welch, PhD is the creator of Becoming You, a popular NYU Stern course and book that helps individuals reinvent their careers. I’ll be interviewing her, alongside startup operator-turned-consultant Shelby Wolpa, about career reinvention.

Jesse Freese is the founder of a 2000-person community called StartupExperts which brings together HR, Operations, and Finance startup leaders. He will be sitting down with Marcus Sawyerr, who runs EQ, a network of executives, to discuss the role of community and how successful leaders leverage collective intelligence to keep pace with change.

Events are a competitive advantage

Running events is a logistical nightmare. From a team member in the hospital to last-minute schedule changes, there is always another fire! The work of producing events – selling tickets, organizing people, managing ambiguity – is largely thankless work. As with any good performance, you only notice when things go poorly.

But the community, trust, and a shared understanding that events create are priceless. In 2016, my producer and a speaker met and got married. I’ve been told “That moment at Responsive Conference changed my life…” dozens of times. Events aren’t just about gathering people — they’re about creating containers where community, trust, and possibility emerge. They create reference points people carry forward.

And running events creates leverage for the organizer. You become the community builder – the person people look to. They build trust much more quickly than singular conversations can.

The thankless work isn’t, in fact, thankless after all. In an age where AI makes everything faster, it’s messy, unpredictable human experiences that give us an edge.

With Responsive Conference only 25 days away, I’ve been thinking back to February 2016, when I ran my very first unconference. That experiment paved the way for the first annual Responsive Conference later that year, and the format has been woven into every Responsive event since.

An unconference flips the traditional model of a conference on its head: instead of a pre-set agenda, the participants themselves decide what gets discussed. It is deceptively simple, but it’s also one of the most powerful ways I know to spark connection and create unexpected breakthroughs.

I’ll be teaching a workshop on “How to Run an Unconference” at the ​Conference for Conferences​ the day before Responsive, and of course, we’ll be running unconferences throughout both days of Responsive Conference 2025.

Don’t have a ticket yet?
​There’s still time!​

What is an unconference

An unconference is any event where the agenda is set by those who attend. The rules of an unconference are simple:

1. Whoever shows up are the right people
2. Whatever happens is fine
3. Whenever it starts is the right time
4. It is over when it’s over

In less flowery language this just means ditch expectation and don’t try to control the experience.

Flow of the Day

After attendees arrive, an empty conference agenda is posted on the wall with time slots and a variety of meeting spaces. Leaders share a theme or question they would like to discuss and post it in a time slot. If you post a topic, it is your responsibility to turn up to that session and introduce your topic or question. If you are not hosting a session, you are free to attend whichever of the sessions you are interested in.

Attendees are encouraged to adopt any of a number of roles:

Leader — who is facilitating each breakout
​Scribe — is someone responsible for taking notes for each group
​Nomads — give attendees permission to move between break-outs

The Law of Two Feet

Everyone at an unconference is encouraged to practice the law of two feet. The law of two feet says that if you become uninterested at any point, you are encouraged to leave and join another session. In an unconference you are also invited to take breaks at any time, with the idea that it is sometimes in the breaks that the ‘A-ha’ moments arrive.

Roles & Responsibilities

There are three main components necessary to a successful event — recruiting, production, and a strong facilitator.

A Word on Recruiting

In my experience, it is helpful to have an extended network to help with recruiting, not just a single person. All other logistics can be handled by a single person.

Production

Among the organizers, someone has to be in charge of logistics, including:

• Venue sourcing and ongoing communication
• Setting the date
• Attendee arrival emails
• Day-of logistics
• Recruiting

Facilitation

A strong facilitator can make or break any event, but especially one with as fluid an agenda as an unconference. On the day of the event, the facilitator plays a crucial role. It is essential to have one strong facilitator overseeing each unconference, to welcome attendees and provide context for the event.

How to Facilitate an Unconference

Here are some tips, most learned the hard way over hundreds of hours of practice in the last two years.

Stay Centered

Despite having spent a fair amount of time on stage, I found myself getting nervous and feeling rushed in the hours leading up to a day-long unconference. My single biggest piece of advice for a facilitator is to arrive with plenty of time to spare so you won’t feel rushed. You are responsible for the framework within which the attendee experience takes place. As such, staying grounded and centered is the single most important thing you can provide, even though in the moment it may feel like it is more important to make sure the space is set up or the coffee is ready.

Don’t Participate

This one might seem odd. It can seem like the entire point of organizing an event is to participate. In my experience, doing so decreases the ease with which I was able to coordinate new sessions, lead an end-of-day wrap-up, and refocus attendees when necessary.

In my view, the facilitator of the unconference is there in service to the attendees. I have found it gets in the way of the attendee experience to actively participate in sessions and workshops that occur throughout the day.

Practice

The facilitator should practice before the beginning of the unconference. Review these guidelines for a successful unconference and be able to describe unconference rules from memory. Practice your welcome speech.

Incorporate movement

I have always found it very useful to incorporate movement into events. When we have short periods of movement interspersed with other kinds of learning, we shortcut the passive sit-and-absorb tendencies we all learned through the education system, and which have carried over into most events. Read this article on the importance of movement within events.

Conclusion

Events are a lot of work, and something I’ve learned to produce of necessity. However, in this hyperactive digital age, I’m convinced of the value of what Tony Hsieh calls “spontaneous collisions” — the value of people spontaneously crossing paths. If you’re considering putting on an event of your own, I encourage you to do so. When we create a container — an event or gathering — we create the opportunity for emergent possibilities to fill the open space.

I’ve been delinquent in writing Snafu this last week, because…

• I bought a house and moved in
• ​Responsive Conference is coming up in 32 days
• There have been some minor family emergencies
• I’ve had several Zander Media film shoots
• The state of the world? ‍♂️

Anyway, I thought I’d take this excuse to look back at some of my favorite essays of the last few years…

​How to run an unconference – I wrote this a decade ago, but still send people to it when they ask how to get started running events. In fact, I’m going to be leading a workshop on this topic at my friend Jenny Sauer-Klein’s the Conference for Conference on September 16th, which is the preamble to Responsive Conference 2025!

​The free pass system – I’ll be sharing this essay with new friends for the next decade. It’s such a simple reframing of boundaries and expectations in friendship, and has already improved mine.

​Some reflections on turning 39 – I got more positive feedback on this article than most. I think the mix of practical reminders and authentic reflection worked.

​Tilting at windmills – Choosing your battles is an essential skill, as is not arguing with reality. But the idea of going to battle against unrealistic odds when you choose to? It’s a little bit crazy, and I kind of love it.

​AI inflection point – One of the unexpected benefits of my foray into housing was this AI inflection point. This technology is transformational, and anyone who isn’t addressing it in their daily lives is going to be left behind.

​How to buy a used car – My girlfriend is buying a used car and I referenced this article to remind myself of what we should look out for. (I think that’s a goal for all great writing: write what you want to read and will reference in the future.)

​How to run a self-experiment – I’ve been running self-experiments since discovering the term from my old professor Allen Neuringer. The idea is to test hypotheses in small ways and on yourself, but to do so as rigorously as possible.

​How to fast – Another reference article and on the habit in my life that is the hardest thing I do. And also, likely, one of the healthiest.

​Discipline isn’t hard – In a world that is convenient and comfortable, we need manageable discomfort in our lives. But it doesn’t have to come through force. Instead, I want a re-definition of “discipline” back to the original meaning of the word.

​Habits for hiring – Hiring and managing people is hard work. And when you find great people, it makes a world of difference. These are some lessons about hiring and management I wish I’d learned a decade sooner.

​How to change someone – This article got me started. It is about my father, published with his grudging permission, and I think about it regularly. You can’t change people, and anyway it is none of your business.

I’ve never thought of myself as a great salesman. But a few months ago, two friends asked me for help with their sales and self-promotion.​

That resulted in teaching a cohort of ten people about sales. And when the 10-week cohort wrapped recently – just two months out from Responsive Conference – I didn’t have the time to run the cohort again.

Instead, I recruited some of my students and a handful of other volunteers to practice sales by selling tickets to Responsive.

I started the workshop by telling my own Responsive story, which goes something like this:

The future of work

In 2015, I was introduced to Responsive.org, a movement started by 6 organizational design nerds to describe the tensions facing organizations in the twenty-first century. As someone who’s worked in dozens of different industries – and seen a lot of the same dysfunctions across silos – I related to the challenges described. Moreover, the manifesto isn’t prescriptive. It doesn’t propose to solve everyone’s challenges.

I asked the authors of Responsive.org what I could do to help, and someone suggested I run an un-conference. I expected 30 people to show up, and instead we had 300 travel from across California for our free 1-day event. Attendees ranged from global CHROs to baristas from an employee-owned, self-managed community kitchen.

I realized there was an appetite for these topics and – never having been to an HR or organizational design conference, but as a longtime circus performer – decided to try my hand at building an event of my own.

7 months later, the first Responsive Conference was a resounding success. Chris Fussell came and gave a talk about “team of teams.” Joel Gascoigne argued that teams should be either fully distributed or entirely in one location, but nothing in between. Tony Hsieh (RIP) sat in the back with his entourage and took copious notes. I got lucky and the ideas espoused in the Responsive.org manifesto had struck a chord.

And those arguments – including “the rate of change continues to accelerate” and “the future is increasingly hard to predict” – have borne out a decade later. Once fringe, those ideas are now commonly accepted. And Responsive Conference continues to serve as an intimate, immersive gathering for founders, executives, and people leaders from around the world to build more resilient work.

What a story does

Having both lived that experience, and told that story a thousand times, I can reiterate with ease. But then comes the essential step of helping other people tell their own stories. Which means, first, we have to reverse engineer my story.

My story does several things:

• It’s entertaining – it shows how a circus performer can end up curating a business conference.
• It’s self-revealing – It helps people know a bit about me with some self-deprecating humor and humility.
• It’s intriguing – it invites the audience to consider learning more about the event or inspires someone to take a risk and start something of their own.

My story isn’t a hard sell. (I despise hard selling.) I don’t conclude with a “please buy a ticket to the conference!”

The goal is to connect, entertain, and leave the audience wanting more.

After sharing my story, I asked the members of our newly christened Sales Squad to draft their own stories about Responsive Conference for review.

If they’ve attended Responsive Conference previously, what impact did it have? If they haven’t, what’s their connection with the future of work that inspires them to participate?

Homework

Everyone has a story. Write a short version of your founding story – whether for a project, business, or personal mission – in less than 300 words.

What led you to start?
What problem were you trying to solve?

In a low-stakes conversation, tell this story to someone new. What questions do they ask? What do they laugh at? What lands?

A few weeks ago, a salesman from an AI lead generation company cold-called me.

I told him I was busy, but invited him to follow up with a short Loom video showing how his product could help Responsive Conference. I promised to watch the Loom and respond if I was interested.

He followed up – without the Loom, and with a generic pitch.
He lost the sale.

I posted about my experience on LinkedIn, with the takeaway that there are two types of selling:

❌ Coercive selling: fast-talking, pushy, ignoring requests to “follow up later.”
✅ Authentic selling: clear, respectful, tailored, and actually helpful.

Coercive selling might get short-term results, but it destroys trust. Authentic persuasion builds relationships. As BJ Fogg, PhD, says, it’s “helping people do things they already want to do.”

What’s surprising about this story is what happened next. My LinkedIn post blew up. A lot of people commiserated with the experience of being pitched but not listened to.

And other people – these are strangers on the Internet! – started lecturing me on the difference between a lead and a qualified customer, and told me that I owed it to the salesman to listen to his pitch.

I don’t think I was sharing a controversial take. I believe that coercive selling ruins trust. If a salesperson doesn’t listen to a simple request during the initial sale, they’re very unlikely to take care of the customer after the sale is closed. Great sales is about taking care of people.

These beliefs aren’t universally held. Apparently, there are angry salesmen on the Internet who are willing to fight about these ideas.

For the first time in my life, my response is: bring it on! I’m delighted to fight with these strangers; to tilt at these windmills.

Because the world needs more people who actually give a damn.

Homework

Find a moment (online or off) where you genuinely disagree with something. Don’t stay silent. Speak up. State your case clearly and calmly. The goal isn’t to win, but to practice not avoiding conflict when you really care.

A few years ago, a friend and I kept trying to make plans. I canceled several times – once due to a car crash – and after the third or fourth reschedule, she told me it wasn’t working for her and that she was going to deprioritize our friendship. I apologized, we talked it through, and agreed I’d take responsibility for reaching out.

I followed up for six months with no response. Eventually, she let me know she was no longer interested in being friends.

I was hurt. We’d had a clear agreement, and she’d gone back on it. That experience stuck with me – and led me to adopt my best friend’s “Free Pass System.”

When you notice someone does something that doesn’t work for you, you are responsible for telling them so. The key is to tell the other person before the issue has become insurmountable.

Tell the person that their behavior won’t work for you going forward, and why. Detail the specifics of what you want to change going forward.

They get a Free Pass up until this point – assuming you still want a relationship with this person. Grant them grace up until this point. That’s only reasonable because you haven’t told them that their behavior doesn’t work for you!

But you have to set clear consequences. Setting consequences is hard because most of us don’t have practice. First, articulate the boundaries for yourself. Then, describe them to the other person.

Consequences aren’t punishment – they’re about clarity. They tell the other person what you will do if the behavior continues, so that you’re not reacting or building resentment, but fostering the relationship that you want.

Here are a few examples:

• If someone is flaky after you’ve communicated that it doesn’t work for you, don’t schedule with them again.
• If someone shares a secret that you shared in confidence, don’t share private information with them in the future.
• If a client doesn’t pay on time, add delinquency fees to the bill.
• Boundaries can be small and nuanced – like the fact I don’t talk to my parents if they sound crabby at the start of a phone call because that’s when our conversations are most likely to go poorly.

To summarize the Free Pass System:

• When someone crosses a boundary, identify the boundary to yourself, and then to the other person.
• If you don’t want them in your life anymore, cut them out of your life.
• Otherwise, give them grace – a Free Pass – up until now.
• Describe to them the clear consequences if they do the unwanted behavior again.
• Then, if they exhibit the behavior again, enact the consequences you’ve communicated.

I don’t bemoan the loss of friendship with that person who wrote me off. As a result, I learned how to set better boundaries.

Whether in friendships, family, or business, the Free Pass System helps you set and hold boundaries. It won’t fix every relationship, but it will improve the ones worth keeping.

Homework

Sit down somewhere quietly for 10 minutes and write out for yourself one behavior that someone in your life does that bothers you. What is it, specifically, that you don’t like?

Then describe the boundary you will set – anything from a timeout to removing them from your life – if that behavior happens again.

Finally, share your Free Pass and its consequences with the person involved.

I just wrapped up ten-week series exploring a different approach to selling. During our last session, each attendee taught one of the topics we’ve spent the last few months discussing. These are a few of the takeaways…

• Sales as service – Sales is best conducted as a service. When we set out to provide an incredible experience for our prospective customer – creating “unreasonable hospitality” to quote Will Guidara – sales feels easy and the right customers feel silly saying no.
  ​
• Believe in what you are selling and who you’re selling it to – If you don’t believe in what you are selling, stop. If you don’t believe the person you’re selling to, stop. Authentic selling comes from trusting the person you are talking to.
  ​
• Attitude – Being present with your customer is a superpower. If you maintain an attitude of loving-kindness, you’re likely to be well-remembered.
  ​
• Emotional connection – Everything in authentic sales is predicated on establishing a connection between you and your prospect. People buy from people.
  ​
• Enthusiasm is a competitive advantage – As Kevin Kelly says, “Optimism is worth 25 IQ points.” When you’re showing up enthusiastic, you’re more believable, more likely to close the sale, and you’ll have more fun.
  ​
• Integrity – It’s useful to define “integrity” for yourself and what you mean when you think of integrity in sales. For me, that means selling and persuading without using force and while keeping my commitments.
  ​
• Two beliefs that are helpful:
  • There is abundance – You don’t need – or want – a sale that isn’t a good fit.
    ​
  • They know best – Your prospective customer always knows what’s best for themselves.
• What’s your founder/origin story – One of the essential ingredients in connecting with a customer is telling your founder’s story. Why are you talking about this topic, and why should someone else care?
  ​
• The four elements of story – There are a million ways to tell a compelling story. But one of the simplest is a four-part structure: setup, change, turning, and resolution.
  ​
• Help them, no matter what – One of the best ways to cultivate a long-term relationship is to help the person achieve their goal, even if that means recommending something outside your offering. Be like Santa in Miracle on 34th Street.
  ​
• Flexible goals – If you’re using pressure, you’re not maintaining flexible goals. If your goal is to help somebody, even over closing a sale, you’re not going to be disappointed if they say no.
  ​
• Asking questions – Ask enough questions to learn about your customer’s pain points. They’ll tell you what you need.
  ​
• How fast you can get to “no.” – Get to know your prospect and their needs as quickly as possible. There are 8 billion people in the world. If the person you are talking to is not a good fit, somebody else will be!
  ​
• The ask – Asking for what you want is usually the hardest part of a sale. But it doesn’t have to be hard with clear boundaries. The pressure most of us feel when we prepare to ask comes from a fear of rejection and being told no.
  ​
• Boundaries – Boundaries can be as simple as time-boxing meetings, arriving on time, or discussing what you say you are going to discuss. They can also be as nuanced – doing what you say you’ll do, not negotiating past your comfort, or saying “no” to a sale that isn’t a good fit.
  ​
• Be respectful of their time – At the start of a sales conversation, be clear about the purpose of the meeting. Clarifying your intentions at the beginning of a conversation makes a huge difference in the other person’s experience and your own comfort.
  ​
• Start on time – Always start a sales meeting on time. Arrive early and be ready to begin when scheduled.
  ​
• Check in at the beginning – At the start of the conversation, make sure now is still a good time. If it’s not, offer to reschedule.
  ​
• Keep your commitments – If you told your prospective buyer that the meeting would last 15 minutes, keep it under 15 minutes. Ideally, end 2 minutes early to demonstrate respect for their time.

The following is an expert from my 2017 book Responsive: What It Takes To Create a Thriving Organization​

Doug Kirkpatrick was one of the earliest employees at The Morning Star Company. Founded in 1990, Morning Star would go on to trailblaze self- management in business. But as might be expected of any start-up, let alone one committed to innovative management, the company’s early days were intense times.

Morning Star is a tomato-ingredients manufacturer based out of Sacramento, California. The agribusiness and food-processing industries are notoriously old-school, known for strict command and control structures and rigid bureaucracies. The small group of employees who initiated the Morning Star project had a six-month window to start up the first factory and had committed to beginning operations on a specified day and even at a specific hour. They were a high-performance group, and Doug describes those initial weeks as a high state of flow, with each person striving cooperatively to bring the new company into existence. The company consisted of seasoned employees, and Doug, at thirty-four, was considered quite young.

Several months before the factory opened, the owner of The Morning Star Company, Chris Rufer, called a leadership meeting. The Morning Star founder and twenty-four members of the team met on the job site. They pulled steel folding chairs into a circle, and Chris passed around a page titled “Morning Star Colleague Principles.”

The sheet included just two points:

• Don’t use force.
• Keep your commitments.

The group spent several hours discussing what these principles meant. Questions cropped up. What happens if you have to fire somebody? What if someone quits? In the end, no one found a reason to reject these ideas, and every person there had reasons to embrace them.

Together, the group concluded that these two points were necessary and sufficient, and they would make up the core of all human interactions at the company. Adopting these principles wouldn’t change the day-to-day operations of the nascent company, but they’d have clear guideposts by which they’d proceed.

What they perhaps didn’t fully process at that moment (and what Doug has spent his career implementing, first at Morning Star and now with companies all over the world) was the far-reaching ramifications of adopting those simple principles. Consider, for example, that “Don’t Use Force” effectively implies:

• No one can require anyone to do anything.
• No one can unilaterally make anyone do anything.
• No one can fire anyone unilaterally.
• Each person has a voice within the company and each voice is protected; no democracy or majority rules.
• Checks and balances will be inherent.

At the time, it didn’t register how profoundly that meeting, and its eventual outcomes, would impact the team, and its members individually. As Doug said, “What we did would end up being very radical—but we were so busy we didn’t necessarily see it since it didn’t seem immediately to impact our day-to-day lives.” More than two decades later, those principles—don’t use force and keep your commitments—continue to serve as the bedrock of a successful, self-managed company.

Shortly before opening, Doug and his colleagues celebrated his thirty-fourth birthday outside the same farmhouse where Chris Rufer had called that fateful leadership meeting. The company has gone on to become a model of self-management and the world’s largest tomato processor, handling between 25% and 30% of U.S. tomato crops.

I don’t run a self-managed business, but those two principles have stuck with me ever since first meeting Doug in 2016. Whether in management, sales, or personal relationships, these two simple statements are deceptively profound.

Management – It is possible to run incredibly efficient and effective companies without force. When you set clear boundaries, and stick to them, business works better for everyone involved.

Sales – One of the biggest reasons most of us avoid selling is a lack of clear boundaries. When you don’t use force in sales and are clear from the beginning that any answer is okay, selling becomes easy.

Personal relationships – The only difference between this and any other kind of selling is that the stakes are higher and it’s even more important to not alienate your “customer.” The best personal relationships are also predicated on these two principles.

Inspired by Ryan Holiday, I’ve made a practice of listing a few things I’ve learned over last year on my birthday. Here’s 37 and 38. And here are a few things I’ve learned in the last year.

Chaos

We’re living amidst more turmoil than any time in several generations. And, despite being relentlessly optimistic, I think things are going to get worse before they get better. I wish that weren’t true – I’d love to build my business and raise my family in peace. But the next decade, and likely the rest of our lives, are going to be chaotic. Assuming that, the question becomes: how do we stay resilient?

AI is here

To paraphrase William Gibson, “It’s just not evenly distributed yet.” I’ve known AI is important for years now. At Responsive Conference, we’ve curated about AI since 2019! But I hit an inflection point this spring and now I’ll talk about the coming AI storm to anyone who will listen. Among my peers, it is trite to say that AI won’t replace people but instead people using AI will replace people. That phrase is true – as far as it goes. But it doesn’t do justice to the amount of change and disruption that I believe is coming.

Adaptability

Fellow entrepreneurs have been asking me how I feel that my business of the last six years, Zander Media, may be replaced by AI. As someone who’s reinvented himself and his career more than a dozen times in the last fifteen years, I’m more prepared than most to adapt to change. That’s what it means to be an entrepreneur – and also a prepper.

Adaptability is among the most important skills in this century.

Optimism is a competitive advantage

If these first two items sound bleak – they are. I don’t think we’re headed into a gentle time in human history. Thus, optimism is even more important than ever. As Kevin Kelly wrote in Excellent Advice for Living: optimism is worth 25 IQ points. When we show up with optimism and enthusiasm, people are more likely to listen, to follow our advice, and to change. (Optimism is actually a secret to selling.)

Durable skills

During my first few months in San Francisco in 2008, a woman asked me what my “hard skills” were – and then had to define the term for me to mean technical skills like software engineering or graphic design. I responded that all of my marketable skills were soft skills – persuasion, storytelling, talking to people, and selling.

Recently, someone introduced me to the term “durable skills” and I like that one better. All my skills are still soft – or durable skills – and I’m good with that.

Sales

There’s a story my dad tells about driving with my grandfather through the Central Valley of California long after my grandfather had retired. My grandpa asked that they stop through a small town and stop by a specific depot. The adult children of the proprietor came out crying, “It’s the candy man! It’s the candy man!” Apparently my grandfather used to bring those kids candy in their youth, as a part of his route as a door-to-door salesman selling tractor hitches..

The ability to sell – not to manipulate, but to persuade – is a superpower. As BJ Fogg says: “Help people do things they already want to do.” Sales and persuasion are going to be important in the years ahead.

The Trades

A friend of mine recently left his senior position at a name-brand technology company, borrowed money, and bought an established plumbing company. An old colleague makes more as an appliance repair man than he ever did as a personal trainer. The Trades, and being able to work, quite practically with your hands, is going to become more important – and more lucrative – in the coming years.

Get into real estate

This one is personal. I don’t think most people should treat real estate as business, even if they want to own property. But I went down a real estate rabbit hole this spring. I’m going to dabble in buying and selling real property for the rest of my life.

Daily habits

I haven’t had my cold plunge available for most of 2025. (The horror!) For a few months, I exercised 45 minutes a day, instead of my more typical two hours. I’ve fallen out of keeping a journal. But my daily habits are so strong, historically, that I’ve been able to build them back with ease. When things are going a bit off the rails, I can easily get back to the basics because they’re well known habits.

Discipline doesn’t have to be punitive

Growing up, I was criticized for not being disciplined. As an adult, people tell me how disciplined I am. No surprise, then, that I’ve always struggled with the idea of discipline.

The word “discipline” originates from the Latin word disciplina, which means “instruction, teaching, knowledge, and learning.” It is derived from the Latin root discere, which means “to learn”. Over time, discipline has come to mean punishment and correction, but the core meaning remains rooted in learning and self-control.

Exercise every day

This isn’t new to me. I’ve been exercising every day since I was 19 years old. I was reminded again this spring – amidst a couple of very challenging weeks – that when I get enough exercise every day, life is better. In particular, I like finding a specific routine (currently: a 5 mile loop through the Oakland hills) and doing that on autopilot. My girlfriend was surprised to hear that I “work” during those runs – mentally processing a lot of loose ends.

Do hard things

I really like doing difficult things. When I’m feeling stuck at work, running a really hard hill makes everything better. When I have a difficult day ahead of me, a few minutes in my cold plunge makes the day easier.

Maybe it’s a study in contrast, but doing hard things really does seem like a secret to success.

Limit social media

I deleted TikTok a few years ago. I haven’t been posting on Instagram almost at all in 2025. For sure, this is to my professional detriment. But my mental health is so much better! Social media is a mixed bag – there are good and bad things about it, for sure – but I’m healthier without it.

Limit screens, generally

I’ve watched two movies so far this year and no television shows. I have a time limit on all of my most-used apps on my phone. When I’m not working or researching real estate, I’m doing my best to avoid screens. And life is better!

Community is strength

When I brought back Responsive Conference after a pandemic-hiatus in 2024, the deciding factor was because I appreciated the value of people gathering in person. For the same reason, I’ve been hosting a monthly potluck to gather people together socially. Humans are meant to operate within a community. Community is strength.

Get a dog (they’ll teach you about presence)

My dog Riley is eight years old. I’m traveling this week, and thinking about her. She’s my best teacher on one important topic: presence.

I’ve done a lot of meditation, and dabbled in a variety of “presence” practices. But nothing has been more useful for practicing presence than having a dog as my daily companion.

I was listening to this Conversation with Tyler with Anthropic co-founder Jack Clark. Tyler asked Jack when we’ll be able to communicate with dogs, and what they’ll have to say. Jack said we probably already know what dogs will say: “Walk!” “Food!” and “I love you!”

Find your rabbit holes

I’ve always been someone who dives deep down rabbit holes. This spring, I spent about a thousand hours on real estate.

As my friend Marie is fond of explaining, the word amateur comes from the Latin “amare” meaning to love. It used to refer to someone who does something purely for the love of it. I think it is really healthy for humans to specialize and to practice out of love.

History > News

Twice over the last year, I’ve developed the bad habit of listening to several political podcasts as I’m waking up in the morning. I’d wake up and immediately start listening to The Daily, followed by other political podcasts. Predictably, I felt depressed for the rest of the day.

I’m learning to limit my consumption. No podcasts or news before 10am or after 6pm. Instead, when I want to think about what’s going on in the world, I turn to history. There’s some comfort in recognizing how much chaos and violence the human race has been through.

Write to think

Writing is hard. Even after writing more than 200,000 words over the last two years, it doesn’t seem to be much easier. But I am a better writer. And my thinking is quite a bit more clear.

Writing isn’t the only way to train critical thinking (BrainHQ is also great), but it is one of the best ways I know.

You know more than you think you do

I’ve been writing Snafu for two years and am always surprised that I have more ideas to write about. Over the last six weeks, I’ve been leading a weekly workshop about a more authentic approach to selling. As I prepare for the workshop each week, I’m consistently surprised by how much I have to say – way more than I can teach in an hour a week! We all know more than we think!

Avoid “Grass is greener on the other side”

I’ve noticed a habit among entrepreneurs to chase a new idea, project, or business when the better course of action is to double down on the current business. I’ve done this a lot across a dozen industries in the last decade!

It is important to avoid sunk cost fallacy! Don’t keep going if you’re just digging the hole deeper. But also don’t jump to something new just because it looks more appealing than the hard work in front of you.

Keep going

Luck accumulates to the persistent. Just keep showing up.

Over the last few weeks, I’ve been teaching a workshop about sales. We get together on Zoom for an hour every week to discuss – and practice – a more authentic approach to selling.

I made my first sales at five years old at Robin’s Pumpkin Patch. Selling is a part of my work today. But I’ve always meant to study sales and persuasion more deliberately, so this workshop format provided me the excuse.

Last week, in a discussion of empathy and connection, I asked the workshop participants a question: “What characteristics make a good therapist?” Or, if you prefer, what makes someone feel like a safe and trusted presence in your life?

It’s not usually their credentials or how convincing they are. It’s how they show up. It’s the way they listen, make space for you to think, and are okay that you don’t have everything figured out. A good therapist isn’t trying to steer you toward a particular outcome, but instead helping you discover what’s true for you.

That same kind of presence is at the heart of my approach to sales.

The most effective salespeople aren’t pushing hard for a yes. They’re not over explaining, and they’re definitely not trying to be impressive. They’re doing something much harder – and much more generous. They’re holding space, asking real questions, and listening closely enough to help someone gain a clearer understanding of what they need.

In that way, sales and therapy aren’t that far apart. Both rely on deep listening, curiosity, and a quiet confidence. They’re about helping people see something they couldn’t quite see on their own – not because someone told them, but because they finally had space to recognize it themselves.

When sales are done this way, it stops being about persuasion. It becomes about partnership. It becomes a conversation that respects the other person’s agency. And when that’s the foundation, a sale – if it happens at all – feels more like a mutual decision than a transaction.

Homework

This week’s homework is to compliment a stranger on the street. Pick out someone in the grocery store or on the sidewalk and compliment them on something trivial – their hairstyle, an article of clothing, the brightness of their eyes.

When I started this habit a few years ago, I was scared. Before I spoke, my heart would beat fast and my palms got sweaty. Today, I compliment strangers with ease. More significantly, I feel more comfortable speaking up in public and I’ve never had someone respond poorly.

Next time you are in public, find something about somebody nearby to compliment and let me know what happens.

I was on a call with a client recently and found myself saying that the human desire to listen to Homer recite The Odyssey is timeless. Even when AI voices become as good as today’s best voice actors, listening to the best in the world tell stories is always going to be worthwhile. Or as Pixar animator Bobby Podesta said to me recently: “Storytelling is a method of value exchange.”

Today’s essay is about taste, an increasingly important skill in our noisy world.

I’ve raved before about Ezra Klein’s new book, Abundance. But I haven’t heard Ezra talk about his craft of writing before listening to a recent interview on the How I Write Podcast. The conversation covered the state of media and the role of AI, but the most interesting topic was the role of an editor. According to Ezra, a good editor is not somebody who makes sure that spelling and sentence structure are correct, but somebody who has taste. Taste, he says, is one of the most valuable skills – in writing and beyond.

I was reminded of a short blog post I read by up-and-coming author Billy Oppenheimer. Before he was a writer, Billy was a ski bum who supported his lifestyle by working part-time as a barista. And he argues that taste – understanding what customers want to drink, how they prefer their lattes, and providing exceptional service – is something that AI can’t replace, even if it does replace his writing career.

I developed taste growing up around my mother’s artwork. From the age of four, she would show me her work, ask for my opinion, and listen carefully to my feedback. I’ve never met a professional artist more open to feedback.

The aesthetic sense I developed as a kid has been a driving force behind my work at Zander Media. I’ve never struggled with a brand direction or critiquing our videos.

In an AI-enabled world, discernment is increasingly important. Creating work that moves people is a valuable skill. Taste is never going away.

My AI avatar logs into Zoom to chat with your AI avatar. Sounds great – fewer meetings! But then what? What happens when AI takes over both our mundane and creative tasks?

This question has been haunting me lately.

If you’ve been following along with the Snafu newsletter, you know that I had an AI inflection point a few months ago amidst attempting to buy my first home.

Even as I was confronted by the painful bureaucracy of trying to buy a house in California, my learning accelerated far beyond anything I’d ever been able to accomplish before. It was a very Responsive.org dichotomy; a tension between traditional bureaucracy and rapid innovation.

Over the course of a few weeks, I realized that AI wasn’t just another important topic, like blockchain, social media, or the Internet. It is much bigger.

Most nights after dinner, my girlfriend and I sit in the sauna. Invariably our conversation turns to AI.

My girlfriend is a data scientist, and has taken the rise of AI for granted for many years. She believes that in the next 18 months we’ll see widespread use of Zoom AI avatars. This led into a conversation about what humans would do instead when our AI avatars take our meetings. And, as someone who talks to people for a living, I’m really not sure.

My only solace is that humans are slow to adapt.

QR codes were developed in 1994, but it wasn’t until the Covid-19 pandemic that we got comfortable ordering food from a QR code taped to a table. And given the option, most of us still prefer a server. Even when we can chat with an AI doctor online, we’ll likely still want to be able to meet with a human doctor, in person.

As the rate of change continues to accelerate, some things are going to be slowed down by humans’ own inertia.

This brings me to a personal decision. I’m doubling down on those things that AI is going to have the most difficulty replacing.

• In-person meetings – even over the convenience of Zoom.
• Educating and selling in-person – instead of through email exchanges.
• In-person gathering – like those that happen at Responsive Conference.

Each of us is going to need to reinvent ourselves over the next decade. The most important skill is going to be adaptability and reinvention.

Today, I’m still taking a majority of my meetings on Zoom. But I’m beginning to default to in-person meetings because they’re harder to replace.

To adapt, we need to lean into work AI can’t easily replicate. But what that work is, I’m not sure.

Last week, I taught the first workshop in a series about selling – because knowing how to influence and persuade are essential skills for navigating chaotic times. I brought together a handful of friends and taught one of the most overlooked elements of selling: being of service.

When we think “sales”, we think of a car salesman trying to persuade you that his junker is just what your family needs. We’ve all received a call from a telemarketer who won’t take no for an answer. That kind of selling gives sales a bad name.

But there’s a growing group of salespeople who are goodhearted, aligned with their audience, and want to create wins for everyone involved. These people know that great selling is about service, not manipulation.

A groundswell

There’s a quiet groundswell of people reclaiming selling.

A son supporting his mother through a cancer diagnosis. A single parent who is struggling, valiantly, to get her daughter to bed on time. A first-time entrepreneur trying to get the world to hear about his new offering.

People taking risks, stepping out on their own, and advocating for what they believe in. This is the approach to selling that we need. And one of the best illustrations of sales as service comes from an unlikely source, a classic movie about Santa Claus.

A Christmas miracle

The example I often give to describe sales as service is the Santa from the 1947 movie “Miracle on 34th Street.” In the movie, an alcoholic Santa Claus is hired to give out candy canes and sell goods for a local Macy’s department store.

The Santa – apparently not caring very much about the job description of “sell things to customers” – answers customers’ questions honestly when they ask him where to buy products that his store doesn’t have in stock. He sends them across the street to the competition!

When the department store manager finds out, he’s furious. How dare this washed out Santa Claus send customers elsewhere, instead of just redirecting them to a different product that they already sell? Until customers begin to return en masse, praising Santa’s good advice and expressing their undying gratitude and loyalty to his store, for guiding them so well.

The department store manager does an about-face, celebrating Santa’s ingenuity.

Enlightened hospitality

Even though we’ve never met, one of my early mentors was restaurateur Danny Meyer, whose thoughtful approach to service has reshaped the hospitality industry.

Danny is the founder of the New York institution Union Square Cafe, and went on to build a variety of other famous restaurants, including Eleven Maddison Park and the global Shake Shack chain.

His approach, often referred to as “Enlightened Hospitality,” emphasizes the importance of caring for employees first, then guests, and then the broader community. If we support our employees, they’ll serve our customers, and the rest will follow.

Inspired by Danny, I designed Robin’s Café to prioritize employees, creating an employee and service-focused environment.

In service to our employees

When I opened Robin’s Café, it was with the clear intention to open a coffee shop in service to our employees who, in turn, would provide great service for our customers.

One night, about six months into running my old restaurant, I came in at closing to pick up some paperwork. The employee who was closing the cafe for the night, turned to me and said, “Robin this is the single best job I have ever had. Thank you for this opportunity.”

This employee worked irregular hours in a small café, serving hundreds of customers every day with no guaranteed minimum of hours. To hear this from him reminded me – and reminds me still – of the reason Danny’s “Enlightened Hospitality” matters. It creates environments in which people will do their best work.

Serving multiple stakeholders

The most skin-crawling sales people sell exclusively for their own betterment. They only serve themselves. A successful salesperson has to at least serve two stakeholders – the salesperson and the customer.

But a sales person who serves a multitude of stakeholders is more likely to succeed. There are more parties invested in their success!

Robin’s Cafe served 5 different stakeholders:

• Employees: in creating a fulfilling, supportive workplace
• Investors: return on investment and pride in supporting a meaningful venture
• Landlord: a vibrant, community-oriented tenant
• Customers: a welcoming, enjoyable “third place,” in addition to good food
• Me: a meaningful, rewarding endeavor, both financially and emotionally

Once you have identified the different parties that benefit from your efforts, it is helpful to delineate how each one benefits from your selling.

Service is selling

When we think of restaurants, we don’t usually think first of a sales environment. But they are.

When the server asks if you’d like dessert after a meal or the sommelier asks if you’d like another bottle of wine with dinner, they are upselling – encouraging you to purchase a more expensive menu item than the one you’d intended to buy.

But what restaurants do differently is sell through the act of serving their customers. By being of service and providing an exceptional experience, they’re creating an environment that we, as patrons, are pleased to pay for.

Whether you’re selling a product, an idea, or simply persuading a friend, selling is about genuine service. When you serve, you don’t just sell. You also create lasting value for everyone.