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.
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• 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.
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• Attitude – Being present with your customer is a superpower. If you maintain an attitude of loving-kindness, you’re likely to be well-remembered.
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• Emotional connection – Everything in authentic sales is predicated on establishing a connection between you and your prospect. People buy from people.
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• 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.
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• 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.
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• Two beliefs that are helpful:
  • There is abundance – You don’t need – or want – a sale that isn’t a good fit.
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  • 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?
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• 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.
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• 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.
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• 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.
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• Asking questions – Ask enough questions to learn about your customer’s pain points. They’ll tell you what you need.
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• 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!
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• 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.
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• 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.
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• 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.
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• Start on time – Always start a sales meeting on time. Arrive early and be ready to begin when scheduled.
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• 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.
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• 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.