What is keeping founders locked up... and what unlocks it.

Before we begin, there's three little presents for you:

1) I had my first call this week with a prospect who had done months of strategy work with Claude to come to the point where he realized he needed an experienced hand moving through a growth ceiling. I'm sure it won't be my last. I've been leading firms through my TrustForge process for the last year, and we're opening it up again this July. It's six weeks to make your offer ready to break through your current revenue ceilingng. Only 15 spots. Lynn, who has been applying the TrustForge training to her business said, "Nick's presence and coaching directly contributed to $18,000 in new opportunities and a year 3x my previous ceiling."

2) Not a workshop person? You're in luck. I work through the same topics in my leadership advisory sprints. I have three open vacancies right now to work with founders, not as a traditional coach, but as a second brain on helping you get through your next growth ceiling. Just reply to this email if you're interested in finding out more.

3) Podcast Hiatus coming - You have spoken and I have heard you! While the "skinny episodes" covering direct application topics to growing trust in ventures are appreciated, it's a little like drinking from a firehose. Good news for catching up - Damns Given: The Podcast is about to go on a three week hiatus to return with a newly refined (and a little more spacious) schedule starting in July. If you missed them, here are three episodes designed to give you clear action right now:

• Consulting is a Little Bit F'ed about how service offerings need to improve to meet client expectations and needs now on Apple, YouTube, and Spotify
• Only Two Ways to Grow Now, Pick One about the rising cost of algorithm dependency for companies and an alternate more fulfilling, more cost manageable way to grow that's hiding in plain sight on Apple, YouTube, and Spotify
• Revenue Models, The Hidden OS of your business about intentionally designing a monetization strategy for your business that keeps it grow and integrous at the same time on Apple, YouTube, and Spotify

Now for the heart of it this week - What's keeping leaders out of the arena?

Two weeks ago, I had the most successful newsletter I've ever sent. Private messages and responses came in. One-on-one meetings were set. A 4000-word post that essentially said, "everything that you are struggling with right now—it's up to you to fix" that hit people right where they were.

As a follow-on, I offered people who responded directly the invitation to do a self-reflection on their readiness for transformational leadership - the only thing capable of breaking the pressurized stalemate our economy and society are in.

Here's what I took away from it... and how the right questions are leading us to better answers.

What Keeps People from Being Ready to Lead Boldly

All the usual caveats apply here - small sample size, non-scientific study, non-representative pool of respondents. But perhaps all the non-conformity of it, the abject weirdness of saying something true on the internet with no reasonable gain to be had in saying it, is why there's so much truth here.

In particularly, these themes are not just from the reflection itself, but from the many conversations I'm having across the ecosystem. The theme: leaders are having a very hard time. Perhaps underestimated even by my "it all comes back to the leader" essay from last week. So much so, that I am realizing I've got to pivot some of my own work this year. Too much is at state.

1. Support systems have failed and everyone thinks they are the only one screwing up. I am seeing this in the client work too. Leaders are deeply isolated. Buried in the Shit LOAD (loneliness, overwhelm, anxiety, and distrust). Industry organizations are extractive and serve only to accelerate capital, not leaders. "Masterminds" are gobledy-gook hamster wheels chasing best practices in the absence of authentic connection. Coaching programs depend on leaders knowing what they want—who can know it when we are overrun by fear of our mistakes? Free money is gone but the sky-high valuation expectations have stayed--exacerbating the crisis of confidence.
   Leaders accept mediocrity and stasis because they believe they don't have what it takes to rise above our current milieu. Missing the point that making hard decisions in the midst of chronic uncertainty is what leaders have always done. It's just no one told them, in their 20 years of technical management experience.
2. We are having existential crises about value that often look like something else (like "leads"). Leaders are unsure about what they offer, what it's value is, who should use it, whether its as valuable as it used to be, and what the longevity of their current offering is. Mostly this is manifesting as anxiety about "leads" or "scale" or growth opportunities. We have been trained by the extraction systems of the internet to chase "leads" with "offers" and judge those offers by "attention" and "engagement." Lies all the way up and down.
   The deep fear about the ability to grow the business is being fed by systemic dependencies that have completely broken down with no new systems rising to meet the gap. This is the definition of an interregnum, of which I laid out five concurrent interregna in the last post.
   What is harder to address is that we are simply ill-equipped to think about, organize, and boldly deliver value to a marketplace sorely needs it and will buy from it, when we are stuck in the Taylorist micro-engineering of every aspect of the business, all in hopes that more technology will make us less afraid.
   (Spoiler alert: it won't.)
3. Money is on the Mind. Everyone, to some degree, is worried about money. Now you could argue this is a chronic condition, but even so, chronic conditions enflame under stress, and we are at peak inflammation. Leaders are worried about sales, payrolls, locking in clients, investors, and of course, inflation. The general sentiment is that money is tight and only going to get tighter. Whether that sentiment is earned or the result of being overly online, is a worthy debate, but it doesn't matter.
   Unfortunately, leaders make some of their worst decisions (both by freezing and by over-extending) when they are making those decisions about money. Ventures work the best when money is understood in its accurate way: as a lagging indicator of long-tail decisions. If we want money to work for us and not against us, we have to make different decisions with an awareness of varying time horizons.
   Leaders label money as the primary reason (by some margin) that they aren't getting the support they need. Which (and let me be gentle here as I can) the more vulnerable truth is that the number one reason is more likely fear.
4. Everybody knows what to do. We're just not doing it. In a previous survey I asked leaders when they've been at peak performance in the past. The answer, almost without exception was when they were working side-by-side with others who share their values and vision. In this most recent survey, respondents by-and-large said that their best experience of their own growth was in well-lead peer groups where they were rolling up their sleeves together. Only one person said that's how they were getting support now.
   Loneliness (the "L" of our Shit LOAD) is a solvable problem. But it isn't solved how we think. It isn't solved by having more meetings. Or even more 1:1s. It isn't solved by chatting more on a-sync message boards in Discord or Slack. Loneliness is solved by being seen in the context of shared belief. And that is the subject of our essay today.

So how do we breakthrough these old patterns?

I'm not going to win the internet this week by making the bold claim that our technology, our habits, even our communities, are built in ways to keep us isolated and afraid. No kidding, Captain Obvious. But I will go one step further and say that we completely understand why these systems were so effective at isolating us, and keeping us from (see above) the exact behaviors we know will empower our leadership in these fog-ridden times.

Turning humans into isolated nodes of commerce that are nudged here and there by addiction-coded algorithms designed to extract every last bit of dollar and sense from you is... old news. We know we should be off Instagram. We know vertical video is how the world ends. We know LinkedIn is a trash hole.

What is more insidious is how these platforms pulled us into self-cremating little fires everywhere, barely lit and yet being consumed day by day. How did we move from consumer to consumed?

The required element is cynicism. Sure I mean cynicism of the general internet variety. The "Everything's fine" World-on-Fire LOLs that are so tired they're comatose. But more so, I mean the subtle and slow-building belief that the thing we've been told to strive for is either not attainable or not worth having. The exit valuation that is a fantasy. The financial security that is now comedy fodder. A business that we actually enjoy doing with people we enjoy doing it with. A world where our children can thrive and create and build for the next generation and the next generation after that.

None of us were emotionally prepared for a world where it was considered gauche to believe in anything at all. And it's killing us. One SMH shrug at a time. We are left with the fruitless options of sell out wholesale to the extractive system, let some VC with a lot of money and a big attitude tell you how to run your business so you can cross-your-fingers cash out at the end. Or play to the smallest most incremental hope--survival. And inch along one year to another until something outside you changes enough to make changing yourself worth doing.

These are, on the face of them, very terrible options. Both cynical in their own ways. Yet, when we believe that they are our only options, who wouldn't waste an hour scrolling YouTube shorts? I would. (And have.)

What is required is a subset of leaders, what I have started referring to as the Quorum, who still believe that there is a world to make and our actions are multiplicative in making that world. That the job of a leader is to decide in the face of uncertainty. The job of a manager is to follow a program. There are no reliable programs left. So all the managers are getting laid off and replaced with AI. Leaving a massive gap for the Quorum of leaders who have fallen in love with uncertainty.

Uncertainty is Where Beliefs Come Alive

• I believe every venture is a reflection of the leader's self-ownership.
• I believe fear is the predominant 2020s emotion but masquerades as a million other things because we are even too afraid to say we are afraid.
• I believe we have the power and the responsibility to build for the next hundred years, even with and because of the uncertainty that time frame implies.
• I believe AI is not a disruptor but a validator of our 20 year disruption of human value with algorithmic extraction.
• I believe we are made by our attachments and connections.
• I believe networks exist and funnels don't.
• I believe every growth challenge has fast and slow solutions and you need both or neither will work.

A good leader loves uncertainty because it gives them the necessary space to act. Certainty is a manager's game, where incremental decisions produce tiny margins. Where bureaucrats and opinion-addicts rule. Uncertainty is for the doers.

In my former field of wealth management, uncertainty should have produced a generation of courageous leaders, building a infrastructure for wealth creation unseen in human history.

Instead, it's created a contracting field of copycat firms run by Xer0x-grade investment firms mass producing sameness so they can more easily consolidate it and sell it to the highest bidder. All run through the homogenization machine of conferences and industry media. For a brief moment, hands were wrung about the lack of leadership development of the second generation of firm executives. Then it got shrugged off with a "let's just give them technology and a private equity playbook instead."

Thankfully, for the few who have access and awareness of them, there exists a counterculture, a Quorum of a a few firms run by leaders. People who eschew the self-congratulatory circles, and believe the work is in the creation of the next thing, not in the stabilization of the last. Leaders who cringe and the performance of client-centricity and obsess over the operation of it at the ground level.

You could swap out "wealth management" in the above with "marketing agencies," "media companies," "tax firms," "software" and many others. Industries are being collapsed into themselves by people thrilled by the absence of belief. Everyone reading this should be obsessed with find the 3-5% of firms in any of the above industries that are thrilled by the creative (not compression) opportunity of uncertainty.

Leaders love to move into spaces undefined by the past because it gives them an opportunity to do what leaders love to do: believe.

Who we are together is made by why we are together

What does all this have to do with loneliness? Of course, everything. When we commune for the purposes of "synergies" and "efficiency" and what is fundamentally tech shopping and M&A scouting, there is no organizing belief, other than mutual survival. It is mass-produced cynicism lubricated by an open bar.

When we gather with authenticity, a little fear, more questions than answers, but with the sincere belief that making something together that has never been made is worth doing, we can come out of hiding.

The partnerships and relationships I am building now, with clients, with an expanding team of CultureCraft affiliates, and with my larger community is built around the expectation of courage. I am asking myself how much courage I can bring. Every time I feel a new twinge of fear (which is daily), I ask myself: do I have more courage to bring to this?

Sometimes the answer is no. Then I know that I need recovery. A centering silence. A round of raucous laughter with my sons. A good book with no application is required. And then the tanks refill, and courage is there, at the ready.

But some times, and more and more lately, the answer is yes. We live and work in systems intent on saying no to anything that doesn't directly serve 7-8 companies. But leading from "yes", first to your own expansion as a leader and what that will cost you, then "yes" to leading without cynicism and seeing where our courage goes.

Remember reply to this email to talk about one of those three leadership advisory slots. They'll go fast.

Forward, forward,

Nick