The Artist, The Architect, and The Scrappy Dog
School Bulletin #22 — Rethinking leadership in a post-playbook world
What kind of leadership survives when the old playbooks burn?
In a post-growth-at-all-costs, productivity-maxed world, we need a new archetype, one that blends creativity, vision, and hustle. Not just to adapt, but to build what comes next.
I had two conversations last month that have stuck with me.
One was with a LP at a venture-focused fund-of-funds. The other is a mid-career leader in corporate innovation. Very different people. Very different contexts. But both pointed to the same shift:
We’re in a post-playbook era.
The systems that made sense in venture, in corporate strategy, in career progression are getting scorched. The growth-at-all-costs era gave way to productivity-at-all-costs. And now even that has begun to crack. The pace of change isn’t slowing. The tools are getting sharper. The margins for error are thinner. And beneath it all, we’re facing a deeper question:
What kind of leadership is needed now?
Essay 1: The Artist, The Architect, and The Scrappy Dog
Venture used to be a smaller world (for those that are in “control” that still may be the case). Fewer firms, fewer dollars, fewer spotlights. It was a niche corner of finance and tech. But then the ZIRP era hit. The flywheels spun fast. Capital flooded in. Firms multiplied. Everyone started playing the role of founder, fund manager, operator, or LP. Relationships got confused with familiarity. Expertise got confused with personal brand.
Now the noise is deafening.
Everyone looks good on paper. Everyone has a track record. Everyone has deal flow. But what we’re learning, especially in this market, is that the questions have changed.
Not just, are you adding value?
But:
Can you adapt under pressure?
Can your team survive?
Can you think clearly when the tools and trends change weekly?
Can you collaborate at the speed of complexity?
Can you learn faster than your context is shifting?
I’ve been thinking about a new archetype of leadership. One that doesn’t rely on pedigree or playbook. One that doesn’t see the job as just execution or analysis.
It takes three forms:
1. The Artist
The Artist doesn’t just consume insights. They create. They connect dots others don’t see. They aren’t afraid to experiment, remix, or dream beyond the frame. They use story, metaphor, and intuition as real strategic tools.
2. The Architect
The Architect sees systems. They bring structure to ambiguity. They ask not just, Does this work? But will this scale? And what do we want this to become? They design for durability. They blueprint the new.
3. The Scrappy Dog
The Scrappy Dog finds the edge. They ask the questions no one else does. They knock on side doors. They have hustle, not just ambition. They execute with humility and curiosity. They’re allergic to entitlement.
The best operators, founders, and investors (and knowledge workers or any industry) today will blend all three.
Marc Andreessen, a few months ago, said the founders of the future won’t be deep experts in one thing. They’ll be good at six or eight. They’ll know how to go deep when the moment demands it. Like decathletes, trained across disciplines, built for situational intensity.
That’s not a tech skill. That’s a mindset shift.
We Are Moving From Knowledge Work to Wisdom Work
The shift isn’t just about tools. It’s about identity. We’re moving from a world defined by knowledge workers to one that demands wisdom workers. People who can:
Navigate nuance
Build trust across silos
Ask better questions
Construct adaptive strategies
Spot what’s missing, not just what’s present
This applies to every layer of the system:
Fund managers: Are you building a durable firm, not just a Fund I?
LPs: Are your filters built for what’s next, or just what succeeded before?
Corporate innovators: Are you training architects and artists? Or just playbook builders?
Mid-career professionals: Are you standing on the shoulders of the old game, or designing your own ruleset?
The Playbooks Are Burning. What Do We Build Now?
We are watching one world die and another take its place. That’s unsettling. It creates real fear. But it also creates the chance to build something more honest, more resilient, more aligned with the future.
In a world being automated, what can’t be templated is:
Trust
Taste
Teaming
Artists, Architects, and Scrappy Dogs will build the firms and institutions that matter in the next decade.
Because this next era isn’t just about surviving disruption. It’s about leading through it. Remember, the early AI world won’t resemble the mature AI world.
As we shift from knowledge work to wisdom work, how are you re-training yourself? What are you doing to cultivate artists, architects, and scrappy dogs in your firm, your partnerships, and your future?
Essay 2: The Metrics of the Unmeasurable
The Founder Traits You Can't Spreadsheet—But Have to Spot
In a recent Swimming with Allocators recording, Benedikt Langer asked a question that’s still ringing in my head.
"Everyone says they look for grit, vision, resilience. But how do you quantify that?"
Great question. Which usually means: hard to answer.
But it got me thinking. The best founders I’ve backed have one thing in common:
They can metabolize tension.
They don’t avoid chaos. They turn it into clarity.
Whether it’s conflicting feedback, internal friction, or market confusion, they learn through it, not in spite of it.
And over time, I’ve found a few tensions that I look for:
Vision vs. Coachability: Can they hold strong beliefs loosely?
Resilience vs. Curiosity: Can they keep moving and keep questioning?
Individual Drive vs. Team Magnetism: Can they attract Exceptions (exceptional talent)?
Bridge Fluency: Have they crossed different worlds personally (a jock who took AP courses or immigrated into the US) or professionally (worked across many industries or functions)?
Signal vs. Noise: Can they name the pain their customers haven’t yet articulated?
Comfort vs. Conflict: Can they metabolize disagreement into a stronger culture?
None of these live in a spreadsheet.
But I try to observe them. And that’s the key word: observe.
Here are some of my lenses:
Backchannel Consistency: Do customers, teammates, and investors tell the same story around the company vision?
The Office Vibe Test: (Pre-pandemic) I could feel if a team was alive or just surviving.
The Question Quotient: Are they asking the questions that unlock new thinking?
The Exception Ecosystem: Are they surrounded by stars who could be CEOs?
The Code Switch Delta: Have they crossed social or sectoral lines with grace and grit?
The Learning Metabolism: What feedback have they integrated in the last 90 days?
This isn’t about founder pattern recognition.
It’s about Exception recognition.
Because the way you evaluate founders?
It’s the way you build your firm.
If you can't explain your gut checks without buzzwords, you're not investing. You're guessing.
So here's the question I'm asking myself:
What am I really measuring?
And here's the one I’ll ask you:
Are you building a firm to catch trends, or to recognize Exceptions?
Closing: With Gratitude
If this newsletter gives you language for what you’re building or the season you’re navigating, that means the world to me.
The School Bulletin was never meant to go viral. It’s meant to go deep.
And now that Groundwork is live and the Swimming with Allocators flywheel is spinning, we’re finally building the kind of insight loop that scales trust, not just exposure.
If you want to sponsor, collaborate, or help spotlight the Artists, Architects, and Scrappy Dogs building what comes next, I’m ready.
Let’s build something that lasts.
With gratitude,
Earnest Sweat
General Partner, Stresswood