I started the How to Sell Yourself cohort series when, independently and within weeks of each other, two friends asked me for advice and mentorship on self-promotion. I’m not an extraordinary salesman or self-promoter, so I declined “mentorship” but suggested we get on a Zoom call to discuss and share ideas about selling.

That single Zoom call led to more, and eventually to me compiling the curriculum for How to Sell Yourself. Since the beginning of the year, I’ve run two 10-week cohorts through the program.

We’re a few weeks into the current How to Sell Yourself cohort, and last week I changed the curriculum on the fly.

I start the workshop with a segment on “Sales as Service,” drawing on Danny Meyer’s reinvention of restaurant service with Setting the Table, Will Guidara’s recent sensation Unreasonable Hospitality, and my own restaurant experience.

I start with redefining sales as service because it’s an unusual place to start a discussion about selling. Service is the opposite of stereotypical selling and one of the big differentiators in how I approach sales.

The second week is about the attitude of a great salesperson, which I encourage everyone to define for themselves, but for me includes love, presence, and acceptance. Instead, we spent the second week of this cohort discussing habits and behavior change!

Behavior change applies to sales in two ways:

• Our own behavior – if we can develop better habits and change our behavior, we’ll learn faster and thus sell more.
• Others’ behavior – when we understand behavior change, we’re more likely to sell in ways conducive to getting what we want.

Every sale is an effort to change behavior – whether your customer’s or your own. Predominantly, though, I focused on habits and behavior change in order to help my students become better learners. As reluctant salespeople, we learn more quickly and are more likely to keep improving.

I asked cohort members to watch this TEDx talk by Stanford behavior designer BJ Fogg. BJ articulates the two things necessary to adopt a new habit:

• Make the habit tiny
• Celebrate your successes

(Now, if only change were as easy as that sounds…)

Make It Tiny

Common advice about habits is that if you want to run more, leave your running shoes out ahead of time. That makes it easier to start by changing the environment around the desired behavior, but it doesn’t make the success of the habit smaller. What if we called success just stepping outside the door? Or running just the length of the block? What if success was sending one email?

There are always ways to set your objectives smaller. This isn’t a lack of ambition. Doing so makes success easier, and thus easier to repeat.

Celebrate Your Successes

I’ve written previously on the unexpected benefits of celebration. BJ describes a handful of different celebrations like doing a little dance or pumping your fist in the air. Celebration is uncomfortable; we have a cultural bias towards self-critique.

As with dog clicker training, the key is that your celebration has to immediately follow your behavior. You don’t trigger the dopamine of positive reinforcement if you wait a few hours and reward yourself with a nice dessert.

Tiny Habits of a Great Salesperson

I left it to my cohort members to apply these two principles of behavior change to their own work in sales, but here are a few suggestions:

Make It Tiny:

Most reluctant salespeople don’t sell because they make their metric of success too big. While selling rewards persistence, most people define success to mean something so far from where they are that they never get started.

Instead, tiny selling can mean:

• Make one clean ask per week.
• Write one short email.
• Send one “thank-you” note or follow-up after a conversation.

Celebrate:

Traditional salespeople are actually quite good at celebrating. At Zander Media, we have a Slack channel that notifies my team when we sell a ticket to Responsive Conference.

The problem is that most sales teams celebrate only a successful sale or meeting their quotas – not the small steps along the way.

Instead, celebrate the little things:

• Physically celebrate (smile, exhale, fist pump) after every phone call.
• Pat yourself on the back after a single difficult client conversation.
• Say out loud, “That was a good ask!” every time you ask for anything.

One of my students, an HR executive-turned-coach, shared that she’s begun celebrating herself after meetings where her only focus is on helping the person she’s with – even if they don’t turn out to be a good fit for her practice. She found herself enjoying meetings, as a result.

As an added benefit to the practice of celebrating, the group now sweetly celebrates others throughout our Zoom with fist pumps and rocketship emojis.

Behavior Change – and Sales

Across the 100 or so books I’ve read about sales and persuasion, there isn’t much about about habits and behavior change. That’s an oversight.

I’m coming to believe that anytime anyone is teaching anything, they ought to start with a segment or two about learning. When we can help people become better learners, they’ll learn more of what they’re there to practice.

This last week was the first time I’ve applied two principles of behavior change to the topic of sales, and this article just scratches the surface. But, at a minimum, anytime we make our habits smaller and celebrate successes, we’re more likely to succeed.

A few months ago, I started collecting Snafu articles into categories, and was surprised by how many taught the tactics of doing something very specific: fasting, buying a used car, raising a puppy, or buying a house.

None of these experiments was a sure thing. In fact, nearly all of them began with the same phrase: “This might work.”

That phrase is the title of my new book. It’s an invitation.

We’re living in a dichotomous era – of unprecedented change and uncertainty. Of leaders promising guaranteed outcomes and “ten steps to anything.”

This Might Work is a record of experiments – of trying things without knowing how they’ll turn out, and what I’ve learned along the way.

Each essay began as an attempt to figure something out: how to tell a great story, how to curate a conference, how to change someone you love.

The through line isn’t expertise – it’s curiosity.

If there’s one thing I’ve learned from them, it’s that progress begins when we stop waiting for certainty. This Might Work is my attempt to compile those lessons in one place – and to invite you to try your own. Because the only way to know if something will work is to start.

Download “This Might Work” here for free:

https://download.filekitcdn.com/d/c7gqh8rbyNUQGR6tynkbna/nYxsYdXjpap6yAD8osSsPb

I went on a fly fishing trip last weekend in Montana with several work colleagues.

When it comes to fishing, I’m a bit out of my element. A trail run through the mountains, a mountain to climb, snowshoeing, or a ski resort – these are all outdoor adventures I know well. But fishing is entirely new to me. Fortunately, two of our party were avid fly fishermen and eager to teach me.

I ended up catching one fish (it was two feet long, I promise), but that’s scarcely relevant. I do understand why people fall in love with fishing. It’s quiet, peaceful, meditative – and a really deep rabbit hole.

Where in the river the fish are. The time of day and year; so many factors determine whether the fish are biting. How you throw the line matters, as well as where it is in the water. Whether your bait is underwater or floats on the surface. I could write an article on “A Beginner’s Guide to Fly fishing” just from the single day I spent on the river.

On the first day in Montana we took a boat down the Madison River and my friends gave me pointers. It helped, of course, that our guide was endlessly patient, rowed our boat, and replaced my flies anytime I got my line tangled in the trees! (As with learning anything, it helps to have someone else take care of the more tedious parts.)

Sitting on a boat on the river, casting and recasting my line – while trying not to get distracted by the bald eagle overhead and the snow-capped mountains in the background – was not a bad way to spend the day.

Even Great Salespeople

Everyone in our party was in sales. Whether an entrepreneur like me who sells to clients, someone managing a startup’s sales team, or as a relationship-driven salesman for an enterprise company, all of us are in sales.

As we were waiting to board our plane, I got to chatting about the Snafu Conference. One of our party said that the best salespeople don’t think of themselves as salespeople. He went on: “We are relationship builders, community builders. What we do is provide value. But we don’t consider ourselves salesmen.”

The best salespeople don’t call themselves salespeople because the word doesn’t describe the way they operate. It turns out that even salesmen don’t care much for salesmen!

Why We Avoid The Label “Salesman”

As I discussed in The Taboo of Sales, just the term “selling” feels manipulative or self-serving. We associate sales with greed, pressure, and rejection.

No one wants to be perceived as a persistent telemarketer among their friends!

There’s cultural shame around sales, even among people who are good at building a network and at persuasion. And understandably so: humans are hardwired to avoid rejection because rejection from the tribe meant death to prehistoric humans. As a species, we crave the approval and support of our peers.

But this results in the ironic twist that while everyone is selling something – ideas, trust, reputation or their love of fly fishing – even the best salespeople resist the identity.

Great Sales Isn’t About Force

As my friend pointed out at the airport, great salespeople bring value to other people. My friends who brought me fly fishing shared with me their love of the sport. I went to Montana! I saw a bald eagle! I caught a fish!

Those friends invited me to join them, encouraged me to try. They provided enough support that I learned something new.

They weren’t trying to win. They didn’t waste breath on why I should enjoy fishing. They just gave me an experience that would – they hoped – show me why they love it.

Great sales is voluntary. It respects the other person’s agency. Had my friends kept saying “See! See! This is why fishing is great!” or had they used pressure, I would have walked away.

Great sales replaces force with service and connection.

What Great Sales Looks Like

My friend didn’t have time to elaborate on what great salespeople do because we were boarding the plane. But I thought about it a lot on the plane ride home. Here are a few of my ideas.

Great Salespeople Are Empathetic

Empathy means the ability to understand the feelings of another. I always think it’s useful to define empathy in contrast to sympathy, which means to feel pity or sorrow for someone else’s misfortune.

Great salespeople pay enough attention that they can relate to or understand what another person is feeling.

Great Salespeople Provide Value

The trip to Montana was orchestrated by my friend Jesse. He planned out where we would fish, where we would stay, and even some local live music on our last night in town.

Providing value is a much-overused concept – especially when you listen to Internet marketers. Everyone’s advice is “provide more value.”

What does that mean, especially when it comes to selling?

I think providing value means trying to help people. We never get to control if we are actually being helpful, but the effort of trying is often enough.

Great Salespeople Connect

I recently got engaged, and two men in our party have been married for years. Throughout the trip, they shared specifics from their marriages that related to my own inexperience.

There’s a delicate balance between offering advice without being condescending. They did an excellent job and only offered feedback when I asked.

When we walked by a jewelry store, and I mentioned the challenges of sourcing an engagement ring, they shared their experiences. When I mentioned that my partner would like a gift from the trip, they offered sage advice on what to bring home.

Great salespeople connect with where someone else is.

Great Salespeople Listen

Jesse spoke at Responsive Conference 2025, and is excited for the Snafu Conference in 2026. While we waited for the rest of our party one morning, he asked questions and listened closely to my thoughts about who the Snafu Conference is for, why I’ve gone to the trouble to start an entirely new conference, and what I’m hoping to accomplish as a result.

At the end of the conversation, we had several new ideas for Snafu and how the conference might benefit his community, which could benefit us both.

He listened carefully and thoughtfully to what I had to say. Great salespeople listen before anything else.

Great Salespeople Have Good Timing

One of our party had taken the entire week in Montana, and I asked him how that influenced his day job and client relationships. He shared that closing clients on a project came down to timing, and that he’s learned over twenty years in the industry that timing is everything.

In a two-minute discussion, he outlined how clients will always take the time they need to make a purchasing decision. They can’t be rushed. I’ve experienced the same with selling tickets to Responsive Conference. No matter what I do, 50% of attendees always want to purchase in the last few weeks.

In taking time off, my friend wasn’t sacrificing relationships with those clients. Instead, he was giving his clients the space they needed to make their purchasing decision.

Great salespeople have good timing. They know when to follow up. They also know when to give space and let someone take time to make a final decision.

Great Salespeople Say No

One member of our party does a lot of paid sponsorship, and sponsored Responsive Conference 2024. They didn’t sponsor Responsive Conference 2025 because they didn’t find the return on investment sufficient. In short, they said “No” to sponsoring the conference for a second year.

Great salespeople know when to say no – to opportunities and to clients who aren’t a good fit. They can be relentless chasing the right opportunities, but only by first saying no to things that aren’t good for their business.

Great Salespeople Help People

There was a pool table at our Airbnb, and while I’ve played pool before, I’m a long way from being a pool shark. After dinner, the four of us teamed up and played five games of pool. (Of course, my team won.)

My partner owns a pool table, and spent much of the games giving me pointers. He saw that I was interested and offered to help.

Great salespeople help people do more of what they already want to do!

You’re Not Alone In Avoiding The Label

I had a great time in Montana, and am tempted to make a very regular habit of fly fishing in the future. But more than the joys of spending several days in the mountains, or even in learning something new that I’d previously known nothing about, I learned something new about selling.

If you don’t think of yourself as a salesperson, you’re in good company! Most of the best salespeople don’t, either. They just do things that help people, and sometimes collect money in return.

The title doesn’t matter; the behavior does.

Whenever I curate a conference, I think about how people are feeling when they arrive and how they are feeling when they walk away.

When it came to Responsive Conference 2025, most people – regardless of political ideology – were coming in with some degree of apprehension. Whether anxious about politics, AI, or the accelerating rate of change in the world, most people I talked to throughout 2025 were nervous. The next question was to decide how I wanted them to feel at the end.

My word was “excited.” I wanted them to feel excited for their ability to contribute. Hopeful. Ready to roll up their sleeves. My work was to curate an experience that helped people move from apprehensive to excited through the course of the 2-day conference.

I wrote a few weeks ago about my concerns that people were having too good an experience, and the accompanying need to let go of the outcome. The outcome that I curated – almost without knowing it – revolved around purpose.

Simone Stolzoff debuted a new talk based on his forthcoming book How to Not Know. Many attendees came up to me afterwards and talked about how much his talk on uncertainty shaped their experience of the conference. I loved the stories he told about choreographer Twyla Tharp, whose book The Creative Habit is a must-read.

On Day 1, I facilitated A Funder’s Fishbowl with three venture capitalists about investing in startups amidst uncertainty. Perhaps the highest praise I received about that session was each of the VCs approaching me afterwards to share that they intend to use the fishbowl format in the future.

My former boss Vivienne Ming opened on Day 2 with a talk about How to Robot-Proof Your Kids – about how technology can make us better humans (and not replace us). As always happens, Vivienne’s talk ended with a long line of people who want to ask her questions and share ideas. Vivienne’s got “riz.“

I got on stage alongside Suzy Welch, author of Becoming You, and entrepreneur Shelby Wolpa, for a session on values and purpose in an age of AI. Suzy said that most people don’t even know what their values are. As a professor of management practice at NYU Stern School of Business who has studied values for decades, Suzy pointed out that values determine much of our lives, but aren’t taught, or well understood.

To close the conference, Eldra Jackson III brought the audience to tears with a talk about the importance of maintaining our humanity amidst constant change. Eldra was incarcerated for two decades and has dedicated his life to helping people inside the penitentiary system get and stay out. He brought gravitas and provided a perfect end to the show.

As we’ve collected feedback from attendees over the month since, conducted our internal After-Action Review, and considered what we want to do differently at Responsive Conference 2026, I’ve had no regrets. That was new to me.

Ten years ago, producing Responsive Conference was about logistics, ambition, and survival. This year’s conference was fundamentally different. I was calmer and well-resourced. The shift I experienced mirrors my attendees’ experience: moving from apprehension to excitement.

I wasn’t just running a conference. This year, I knew why it existed. That clarity wasn’t only professional – it came from the alignment in my personal life (I’m newly engaged. I bought a house. I’m happier than I’ve ever been.) And when purpose aligns across personal and professional work, execution is much easier. I’ve gone through the same transformation – from apprehension to clarity of purpose.

Attendees arrived at Responsive Conference anxious about politics, AI, and the pace of change. Through talks, workshops, un-conferences, and plenty of time to reflect (and play with animals), they rediscovered what they care about and what they can control. The conference itself was a live demonstration of moving from uncertainty to purpose.

The experience of Responsive Conference – or any great event – isn’t just about content. It’s about remembering why we do what we do, and how to do it better. Without purpose, everything is difficult. With purpose, everything gets easier. The antidote to chaos is purpose.

My mother has been a practicing artist for fifty years. She makes mezzotints, which are something of a lost art. Her curriculum vitae is impressive and her work has been presented in some of the most famous museums in the world.

But my mother lacks salesmanship: the ability to promote herself, share her story, and get people to buy her work.

She is a reluctant salesperson – and she isn’t alone. Most of us have some fear of self-promotion.

We fear rejection, or what people will say about us when we promote our work. We don’t want to be seen as selfish or self-serving.

Part of this is cultural. We’re taught to value generosity and service. Most of us are not raised with an emphasis on self-advocacy. We associate selling with the threat to belonging within our community, to being authentically known, even to being loved.

The cultural taboo

There are only a few cultural taboos – of which sex, death, and money are the most significant. Our boundaries around taboo topics have shifted and the Overton window continues to expand. Once-private, shame-filled topics are now more openly discussed, but sales still carries a charge.

The taboo of sales exists for good reason. From LinkedIn cold pitches to multi-level marketing schemes, there are lots of examples of sales gone wrong. Given the choice, most of us would rather discuss death over dinner than ask someone to buy our work.

The paradox

The irony is that the taboo of sales blinds us to how deeply human persuasion really is. Even though we stigmatize selling, everyone does it daily.

Daniel Pink argues in To Sell Is Human that most people aren’t in direct sales. Instead, Pink describes “non-sales selling” as any activity that requires persuasion and influence. When you convince your team to try a new process, or ask your partner where to go for dinner, you’re selling.

We pretend selling is something only other people do – even while we are all constantly selling.

The cost of a taboo

When we avoid selling, we also avoid clarity. We don’t acknowledge what we want and don’t ask for it.

Meanwhile, a small subset of people do the opposite. These are the salespeople who ask – obnoxiously, incessantly, and without apology.

When we avoid sales, we avoid the clean embodiment of an inherently human behavior.

Redefining the act

The solution isn’t to sell harder but to redefine what selling means. Done well, selling isn’t about convincing. It’s about being clear what’s true for you and inviting others to see that, too.

As my mother begins to tell her story — to share why she fell in love with mezzotints and what they reveal about the world — people won’t just buy her art. They’ll buy into her love for it, as well.
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Sales isn’t something we avoid by pretending it doesn’t exist. When we refuse to speak up, we’re just leaving room for someone else to fill the silence – someone louder, less careful, and perhaps even less honest.

Homework

The sales taboo dissolves the moment we treat sales as service. Sales is a way of being honest about what we want to give and what we need in return.

Make one offer this week. Not a pitch. Not a plea. Just one clean, explicit offer for something you believe in. Say what it is. Name your price. And then stop talking.

The night before Day 2 of Responsive Conference, I spent an hour agonizing over how enthusiastic everyone was. I was worried the conference hadn’t struck the right balance of existential dread and optimism for the future – given that I feel a fair bit of existential dread myself!

But after stressing over my attendees’ experience for an hour, I looked back at the agenda I’d curated for Day 2 – starting with my old boss Vivienne Ming and ending with Eldra Jackson III – and realized that the program I’d created would provide attendees the experience I wanted them to have: real, raw, but not pessimistic.

One of the things I like most about live events – whether as an MC, speaker, or athlete – is that once the show begins, we have to let go of the outcome. As much as we’ve practiced our lines, rehearsed our talks, or reviewed our notes, once the show begins, there’s nothing to do but continue.

One of my early teachers, Feldenkrais-disciple Anat Baniel, described this idea as “flexible goals.” In the subsequent eight years I spent working with autistic kids, maintaining flexible goals was the only path forward! A myopic focus on hypothetical outcomes, like “I want my child to be neurotypical,” would impede progress.

Maintaining flexible goals, or letting go of the outcome, doesn’t mean that you don’t have an outcome in mind. When I am trying to sell tickets to Responsive Conference or a client on behalf of Zander Media, I want them to buy! But that’s only one of a handful of goals I hold simultaneously – including to be of service. Maybe there is someone I can introduce, a book I’ve read, or something else that would make a difference in their lives.

Let go of the outcome

Anytime I find myself feeling urgency or anxiety, I remind myself “Let go of the outcome.”

In the case of my attendees’ experience of Responsive Conference Day 2, the solution was simple. I’d already curated an excellent experience that didn’t shy away from difficult topics. From our opening and closing keynotes to topics ranging from AI to politics to the Safari animals who joined us at lunch, the experience of Day 2 provided my attendees with a rich and varied experience. I’d already done the hundreds of hours of preparation necessary. All I had to do was let them enjoy the experience.

Letting go of the outcome is a mental act. It is more about coming up with a half dozen ways in which other outcomes – in addition to your goal – could be just as good.

In the case of Responsive Conference 2025, if my attendees have too good an experience, is that a bad thing? So, they feel optimistic leaving the conference – and only afterwards are confronted by the realities of our rapidly changing world. There’s nothing wrong with providing a bit of escapism.

But if I’m trying to sell something specific or my mortgage depends on a certain level of earnings, it can be difficult to stay flexible. I have to deliberately make a list of alternative outcomes:

• If someone doesn’t buy from me, they’re looking out for their best interests.
• Maybe I haven’t done enough preparation? Maybe I’m not telling a compelling story?
• Or perhaps what I’m selling doesn’t fill a pre-existing need.

In the months leading up to Responsive Conference 2025, one reminder I had to give myself was to “Be less entitled.” As salespeople, we are not entitled to someone else’s attention – not to mention their money! If I was asking for help from colleagues to promote the conference, it was my responsibility to make it easy for them to promote. And when someone bought a ticket, take a moment to celebrate that small victory – instead of immediately calculating how much farther I still had to go.

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Homework

What are you trying to accomplish? List out 5 alternatives, beyond your primary objective.

Even with your primary objective in mind, can you make one of these secondary goals as big or bigger than the first? Can you want more for the person you’re talking to than for yourself?

It helps to write out then goals, and then write an explanation for each.

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.