01
AI didn't kill servant leadership alone — the end of free money did, and AI finished it
The 12-year zero-interest-rate 'bull run' made 'hire great people and get out of their way' viable; when capital tightened and revenue-per-FTE became the North Star, passive leadership was already on the ropes. AI delivered the final blow: if agentic systems execute with no emotions or career aspirations, 'who are we serving?'
Why it matters: Stop optimizing for team comfort at the expense of output and re-anchor leadership on accountability, speed, and outcomes.
FoundersSales LeadersRevOps Leaders
02
Replace servant leadership with 'active leadership' — lead from the front, no job too small
Active leadership means embodying the work rather than delegating away from it. Michael throws away the stray coffee cup at the event his team runs, and builds custom GPTs himself because he holds the most company context. The natural career path toward people-management pulls you away from the work; AI is a chance to come back to it.
Why it matters: Senior leaders create more value doing high-context work than managing politics — get back onto the field.
FoundersSales LeadersMarketing Leaders
03
Treat every company as peacetime or wartime — and know we're at war
Borrowing Ben Horowitz's peacetime/wartime CEO idea, Michael argues the last 12 years were peacetime (stable, predictable, growth-at-all-costs) and today is wartime — speed, precision, and survival. Free-money multiples and easy acquisitions are gone; only the most productive, profitable companies make it to the next level.
Why it matters: Wartime demands smaller, faster teams, tighter priorities, and a bias to ship over polish.
FoundersRevenue Executives
04
Build AI-first teams with a change-management ritual, then flatten
Michael has everyone put a Post-it on their monitor: 'How can AI help me do what I'm about to do?' Retraining individuals lets the team shrink and simplify — people who would have been people-leaders three years ago now do the work at high velocity, which he finds more fulfilling.
Why it matters: AI adoption is a behavior-change problem first; the org-design payoff (flatter, leaner) follows the habit.
RevOps LeadersMarketing LeadersFounders
05
Be micro-interested, not micromanaging
Credit to Rippling COO Ian McInnis. There's a middle ground between smothering and absent: get close to a work stream to build context and coach, then step back and grant autonomy once you see consistency. More face-time signals concern, not favoritism — and Michael tells his team so explicitly.
Why it matters: Name the behavior openly so proximity reads as investment and coaching, not surveillance.
Sales LeadersMarketing LeadersRevOps Leaders
06
Trust is consistency over time — so coach your best performers, not your strugglers
Michael's equation is 'consistency over time equals trust.' And counter to instinct, strength-based orgs invest in top performers — like a coach who spends the most time with the best athlete — rather than pouring hours into someone who is simply a poor fit for the role.
Why it matters: Audit where your coaching hours go; you get more leverage 5x-ing a top performer than extracting 10% from the wrong seat.
Sales LeadersMarketing LeadersRevOps Leaders
07
Get the right people on the bus, in the right seats — and design the right seats
Michael loves Good to Great's bus metaphor but says the missing piece is designing the seats themselves — the actual jobs — which is changing fast as AI absorbs execution roles. He also warns that a flat performer a year later is below the line because the company improved; you have to out-improve the business to keep your seat.
Why it matters: Revisit role design, not just staffing, and set the expectation that standing still is falling behind.
FoundersSales LeadersRevOps Leaders
08
Make your people decisions inside the first ~120 days — then own the outcome, kindly
A mentor's rule: you have about 100–120 days in a new role to make your people and structure changes; after that the output is your fault or your benefit. Do it early, thoughtfully, and humanely — bake severance into the budget, be a great reference. Most people know when they're doing a medium job and feel relieved.
Why it matters: Delaying hard people calls forfeits your right to complain about the team you built.
FoundersSales LeadersRevenue Executives
09
The junior-execution layer is evaporating — protect the on-ramp and build taste
AI is absorbing the entry-level roles where people once learned skills, found mentors, and made economic sense. That breaks the talent pipeline and, for mid-career leaders, the connection to what's 'cool.' Michael's hedge is taste — the judgment to know whether AI's output is good — because AI takes prompts, it doesn't have taste.
Why it matters: Deliberately recreate junior on-ramps (often via agencies) and treat taste as a durable, teachable competitive edge.
FoundersMarketing LeadersRevOps Leaders
10
Agencies are the new junior on-ramp — and should sell customer-focused, not solution-focused
Well-defined, 'wrapped present' work can go to junior talent at agencies; ambiguous 'plate of spaghetti' work stays in-house. In the 'new lean startup,' zero-to-$10M companies with tiny teams will outsource heavily. Winning agencies pick a customer and stack solutions (LeanScale's approach), compounding trust into an easy button the buyer can just press.
Why it matters: If you run or buy from agencies, optimize for a trusted, expanding partnership over one-off project bids.
FoundersMarketing Leaders
11
Chase 'career market fit' and know the neighborhood, not the destination
Michael doesn't call himself a marketer, but the market does — that's career market fit, and ignoring it would be silly. Early on he chased brand logos (Starbucks, Nike) to build perceived credibility. His rule: know the neighborhood you're heading toward and take any avenue pointed that way; don't wait tables for the straight line.
Why it matters: Optimize for direction and reputation-building work — and follow Munger: the best way to get new work is to focus on the work on your desk.
FoundersSales LeadersMarketing Leaders
12
Run a quarterly-sprint-monthly cadence — and let the snow melt from the edges
Three frameworks: quarterly OKRs with an above/below-the-line priority cut and built-in slack time (so you can say no with kindness and yes to the CEO's fire drill); two-week to-do/doing/done sprints with review, retro, and a Friday 20% block; and a monthly company-wide all-hands that forces public shipping. Push decisions to those closest to the work — 'the snow melts first from the edges.'
Why it matters: A lightweight operating system plus edge-empowered autonomy delivers predictable velocity without heavy management overhead.
RevOps LeadersSales LeadersMarketing Leaders