Hi everyone,​

Welcome to the August edition of the Insider. Do you know someone who would enjoy the Insider? Forward this email to them, and they can subscribe here.​

Pointless pursuits

Maybe it has always been this way—our collective understanding that every minute of our day must be productive. Perhaps generations before have internalized the same lesson: that there should be some purpose, some point, some ROI for everything we do. Even leisure must be justified—our rest enabling us to “sharpen the axe” so we can return to the world ready to slay.

As a father, what message would my son internalize if he (11 months, 22 pounds, 0 words) were fully aware of how I hustled and bustled? Would he see a man who believed that everything must have a point, that every action was a small yet important brick in the masonry of some enormous and never-ending castle? Or would he see his father as someone who just did things for fun, for no commercial interest or productive itch, or—it is dangerous to even say out loud—for no reason at all? Things, it might be explained to him one day on a car trip, one does just because.

Sometimes my entrepreneurial friends will confess to me, after I have made similar confessions to them, that they don’t read fiction anymore. Or they don’t have hobbies like they used to. Or that as a father they feel this overarching paternal duty to be responsible, well-planned, useful. And I tell them the same. I, too, have wondered where my playfulness has gone, and how it’s been replaced with that vague, utilitarian pressure to optimize always and everywhere. 

How do we re-acquaint ourselves with the pointless pursuits and delightful detours, the minor obsessions and major hobbies, the pastimes that are defined by their just because-ness? I don’t know–I’m curious how you do it—but I want my son to know that man, and to see the world as something not to be conquered with his sharpened axe, but something to be inhabited with all his senses.

Open for businesses

Inspired by mentors who have done the same, a few years ago I embarked on a journey to build a small portfolio of lifestyle businesses I plan to hold long term.​

The first is Future Forest. I've given my full attention to Future Forest for the last year, and we’ve built a stable business managing every step of our clients' newsletters. One of the best things I did in the last year was to hire Chris, our general manager. The intention had been to hand the business off to him over time, but Chris proved himself to be a capable operator and leader, and I stepped out of day-to-day operations sooner than planned. Chris has built a team around him, including one of the best hires I ever made during my Uncharted days: Laura Saracho. Now they’re off to the races, and I get to support from the sidelines.​

This is freeing me up to focus on business #2, which hasn’t fully come into view yet. This summer, I’ve launched two pilots of businesses in different markets to validate demand and positioning. I’m also considering buying an existing business.

Whether buy or build, here are a few criteria for business #2:

  • Business models defined more by resilience and durability through change than by reliance on new trends or new technology.
  • Businesses that don’t require outside funding to reach profitability and have an extremely strong LTV:CAC ratio.
  • Businesses that can differentiate on quality, craft, or service.
  • Businesses that can bolt onto existing networks, audiences, or communities (see below on distribution-first entrepreneurship).

If you know of someone who wants to sell their business or have an idea you want to share, I’d love to hear from you.

Distribution-first entrepreneurship

The distribution-first entrepreneurial playbook reverses the conventional order of build first, distribute second. Instead, it focuses on nurturing trusted relationships with a loyal audience or community before selling, then uses that earned distribution to introduce products that meet customer needs.​

In Sydney last month, I saw this playbook up close. Axel Sukianto recognized the need for a community of B2B marketers in Australia/New Zealand. He started a Slack for trading best practices and honest questions. In the first year, 15 people joined. Today, over 1,500 marketers across the region are in the Generate community.

​The natural next step was to build an event where everyone could connect in person. So Axel and his team did. The first Generate Summit was three years ago, and it’s steadily grown into a major production. To members of the community, it feels like a homecoming. Generate is one example among several of the distribution-first entrepreneurial playbook.

  • Gwyneth Paltrow began goop as a free lifestyle newsletter. Now it’s a business worth $500 million.
  • Lenny Rachitsky started with a newsletter and a podcast. But his audience wanted more, and he's following their lead with events, products, and job boards.
  • MrBeast has built a portfolio of distribution-first businesses. Millions of people formed a relationship with him and his content, and he then used that attention to launch merchandise, Feastables, MrBeast Burger, etc.

Earning distribution before plugging in the product is a playbook we’ll see more of: community leaders becoming entrepreneurs, entrepreneurs teaming up with influencers or building joint ventures with existing communities, and micro products designed for micro communities. Everything, it turns out, is downstream of trust.

Rorschach tests

I’m drawn to stories that are Rorschach tests. Encountering a completely different interpretation of the same events is always startling and humbling and slightly maddening. Which is how I’ve felt when following the story of Jason Arday. Is it the story of a fabulist who plagiarized other academics and attempted to squash scrutiny when journalists began asking serious questions? Or is it the story of a victim who was “lynched” by the media (according to Ibram X. Kendi) and tokenized by a historic institution under pressure to rectify its underrepresentation?

It could be all of those stories in one, but litigating the facts matters less than considering what these stories represent. The responsibility before us is to approach such stories with a softness, a grace. Most of the time, Rorschach stories are mirrors trying to tell us something about ourselves.

Can you help?

  • Has it become hard to sustain the quality and consistency of your newsletter? I’d love to connect you to Chris and the team at Future Forest. We make it almost effortless to build trust with the people who matter by sending the best newsletters in your inbox.
  • Are you about to make an important hire? I’m piloting a new business in the hiring space, and I’d love to get feedback from a small group of hiring managers who are about to embark on a hiring process for a senior leader.

What I am reading

  • Food deserts: This article in The New Yorker really made me revisit some foundational assumptions I have about healthy food access and food deserts. Maybe they’re not a thing? The New Yorker.
  • AI hype: In the genre of AI is overhyped, I appreciated this honest reflection from Brad Feld about his experiment with having Claude write his blog, why it went off the rails, and why he’s returning to human writing. On the data side, the Chief Economist of Apollo shared charts recently that pointed out that, so far, AI is not delivering increases in profit margins for any sectors outside of tech. Basically, the AI capex boom is so far only showing up in the sellers’ margins, not the buyers’.
  • Business and investing: This podcast is kind of all over the place, but it touches on some ideas that have lingered with me: what is the purpose of net worth? Is all content just entertainment? What does the future of SaaS look like? Is what you’re working on something you’re looking up at or looking down at? Invest Like The Best.
  • The history of air travel: The Boeing 747 might have been the pinnacle of American engineering excellence. Its retirement signals an end to an era of American culture—and ambition. The Atlantic.

Something personal

Fifteen years after completing my Master’s in Sydney, Australia, I returned last month to speak at a conference about newsletters. We made a family trip out of it—Lisa and Emilio came, too.​

There are certain places in our lives that act as time capsules. When we return to them, we encounter a version of ourselves who has stayed fixed in time. The smell of a street, the look of the sidewalks, the clasps on the windows—to rediscover the small things is to rediscover the physical and emotional texture of a specific chapter of our lives.​

It is to get reacquainted with a younger self—almost as an author outside of time could visit one of their characters inside a story. And so I did; I met that 24-year-old and felt his homesickness, his idealism, his unsureness, his yearning for anchors in his life. And then I reassured him that it would all be okay, that the loneliness would subside, that the chapters ahead would be wonderful and poignant and not always straightforward or easy, but every one necessary.​

To visit one of our time capsules is to pretend, if only for a moment, that we can exist outside of time, that we can look in on the story of our lives as a person would peer into a snowglobe. But then we’ll be suddenly thrust back into this bright, contemporaneous reality, and we’ll realize that we are neither observers nor omniscient authors, but rather protagonists in it. And if we’re lucky, we might be dimly aware that the whole process will repeat one day—that a future self will visit us in this exact moment and say, yes, yes, keep going.

~~~

Signed,

Banks

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