The Insider - June 2026

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

The softness of resilience

There is a new trend in stormwater management where instead of cities beefing up their drains, pipes, and detention tanks, they’re building parks and other softscapes that can absorb and release rainwater before it overpowers a city’s infrastructure. It turns out that permeable playgrounds can be more effective than steel holding tanks. This is true in other domains, as well. In entrepreneurship, we often think of resilience as something hard—gritty doggedness, unflappable resolve. But I’ve noticed that my own resilience often comes from the softest spaces: when I’ve been kind to myself after a tough day, when I’ve forgiven myself for unforced errors, when I’ve let the mistakes just soak into the ground and dissipate versus letting them pool up in my memory. Perhaps becoming more resilient means softening, not hardening.

Four trends in the world of newsletters

The Future Forest team spends its days immersed in the world of newsletters. Here are four trends that might offer clues into the future.

Less news, more letter. We find that top-performing newsletters are written more as letters between friends than curated news roundups. When AI can generate tidy summaries of the news, some of the best newsletters offer a distinctly human and insider take.
Less scale, more intimacy. Gone are the days of trying to scale your newsletter to reach anyone and everyone. Today, small is beautiful. We have several clients who send their newsletters to fewer than 1,000 people, and a few to less than 100. If you have the right people on a list of 1,000, it can generate a higher ROI than a list of 100,000.
Less digital, more analog. We’re noticing more interest in companies shape-shifting their digital newsletters into premium print publications. It’s not exactly true that there is less digital, but there’s a recognition of the power of small-batch print magazines that attract higher-quality attention.
Less broadcast, more conversation. We are seeing more and more newsletters positioned as conversation starters, aimed at engaging an audience: polls, invitations to IRL events, user-generated content, and Slack channels for superusers.

What are you noticing? I’d love to hear.

Be careful how you define reality

It took me many years to realize that part of the work of leadership is to define reality for your team. Teams can achieve something extraordinary when they believe the stakes are high, the odds are long, or they have to race the clock. Teams need antagonists to do their best work, which is the core idea anchoring the excellent and nuanced newsletter of one of Future Forest’s clients, Brad Abare.

But it’s wise to be careful about what you choose to believe. If your 9am-5pm is defined by productive paranoia, it will take care and attention for your 5pm-9am to be defined by presence and rest. Each of us moves through different realities; the goal should not be to deceive ourselves into thinking they all need to be the same. But it is a skill to move between them, and to be careful about how we define them in the first place. The realities that we define ultimately define us.

AI is making us the same

It is very possible that AI is more of a homogenization technology than an intelligence technology. It can act as a big fishnet, reigning in solo explorations and nudging us into the conforming masses.

In a recent study, researchers found that AI-written fiction didn’t just sound like AI at the surface level, but followed similar underlying narrative patterns. The researchers examined the structure of each story: the plot, the escalation of events into crescendos, the introduction of tension, and the use of irony, flashbacks, and moments of surprise. They found that AI-generated stories were less diverse than those written by humans.
I haven't been able to stop thinking about this Substack post—a book editor observing that manuscripts “polished” by AI all sound identical, regardless of subject. Each author believed they had just used AI to write, and their unique voice was preserved, but the stories were functionally the same.
A study of 370,000 college entrance essays found something similar. After ChatGPT was introduced, students began using more flowery language, but the essays themselves lacked genuine creative diversity. They had become variations on a theme.

The quality of our outputs is dependent on the quality of our inputs. Original ideas don’t materialize magically from unoriginal places. Clear writing is the product of clear thinking. Interesting people do interesting things. Beautiful stories emerge when we're in direct contact with the world's beauty.

Most hiring problems start before the search begins

In the fifteen years that I’ve led hiring processes, I can think of maybe one that didn’t begin in a frenzied rush. As soon as a team realizes they need to hire, they’re racing to get the job description posted and interviews scheduled. For important roles that needed to be filled yesterday, it’s easy to conclude that a good-enough job description is good enough. But too often it is not. It hasn’t been shaped to answer the most fundamental questions that determine whether the hiring process will succeed:

How does this role advance the organization’s most important priorities?
What specific outcomes should this person be accountable for in the first 6–18 months?
What candidate profile is most likely to succeed in this role, at this company, at this stage?
How should the hiring team evaluate candidates against the outcomes and qualities that matter most?

Time spent on strategic role scoping and hiring alignment is worth its weight in gold. A mis-scoped job description can add weeks to a search, sow internal confusion, and increase the chance of a failed hire.

In the last few months, I’ve been doing this work as a consultant for small and mid-size teams in a 2-week sprint: turning an unclear or underdeveloped hiring need into a precise role definition, compelling job description, and practical hiring toolkit, scorecard, and interview process. I think of it as the upstream “pointing” work to ensure that all the downstream time, effort, and money actually pays off. If your team is about to hire for an important role and the scope still feels fuzzy, I’d love to help.

What I am reading

I consider it to be a failure of consumer protection that we’ve allowed prediction markets like Polymarket and Kalshi to tacitly encourage insider trading. This article in GQ considers the implications of a world where we can bet on everything. GQ.
I’m drawn to ethnographic journalism that mixes human stories and striking photography, which is why I loved this very IRL article about the communities along the loneliest road in America. Deseret.
Good writing is a function of good thinking, and Paul Graham is one of the clearest thinkers you’ll find. I loved this article for two reasons: 1) it challenges the idea that wealth is inherently exploitative, and 2) it offers extremely simple advice for entrepreneurs of any age (see the Something Personal section for more). Paul Graham.
This is a very of-the-times essay about “How to end your extremely online era: A somewhat practical guide.” Tommy Dixon.
The 4-day workweek is achieved not by placing the burden on individuals to become faster and more productive, but through getting better at prioritizing and de-prioritizing. Which is why the emergence of AI will not automatically usher in a shorter workweek. In some cases, the workweek will get longer and weirder. The Atlantic.
What makes art great? And why is AI so bad at producing original, delightful writing? By examining the hidden surprises of Shakespeare’s sonnets, this article offers an answer. Nabeel Qureshi.

Something personal

When I was thirteen years old, I got my first job as a new account representative at the Young Americans Bank. It was (and is) a bank for kids that teaches financial literacy and entrepreneurship. Every Saturday morning from 8:30am - 12pm, for $7 / hour, I would help kids open their first savings account. The job had perks, which included 1) your own business cards, 2) co-working with adults, and 3) getting an up-close look at the inside of the bank safe.

Last week I returned to the bank for the first time in 25 years to serve as a volunteer judge for an entrepreneurship competition for 6-11-year-olds. My job was to read the 23 applications from young entrepreneurs across the state and provide feedback and business advice. (The winner received $1,000 to expand their business.) There were lemonade stands and pet-watchers, crocheted animals and Rubik's cube teachers. Every entrepreneur had to submit financials and answer questions about their biggest challenges. One entrepreneur was grappling with balancing homework, sports, theater, and running his lizard-watching business for neighbors who were on vacation. Did he have the capacity to take on more clients, he wondered in his application, before suggesting that maybe he could subcontract future work to his mom if he felt spread too thin. Another confessed that it was discouraging to see some of her crocheted animals not selling. But there was no time to wallow; she had to move inventory so she dropped prices. Another explained that the hardest part was realizing that 9 out of 10 people who passed by were not customers. That felt like a lot of rejection.

As I provided my feedback (yes, he should hire his mother, but only if he could charge the client more than his mom’s day-rate; one must always protect the gross margin), it became clear that the advice a 7-year-old entrepreneur needed to hear was the same advice that most entrepreneurs of any age need to hear: listen to your customers, double down on what’s working, consider raising prices, and don’t let the work get in the way of playing with your friends.

~~~

Signed,

Banks