Marcos Rivera

Most B2B SaaS leaders build value.
But forget to capture it.

Let me guess:

- You’re guessing your price
- You’re losing revenue
- Scaling feels stuck

What if pricing could drive growth?

Here’s what I help you do:

→ Capture more value
→ Make pricing your edge
→ Build pricing confidence

Why should you trust me?

- 25+ years in tech pricing
- Ex–Head of Pricing at Vista Equity
- Priced 400+ SaaS products
- Author of *Street Pricing*
- Trusted by MBAs and SaaS CEOs

Beyond coaching, 

I’m an:

→ Investor 
→ Speaker
→ Entrepreneur 

passionate about helping businesses unlock their full revenue potential.

Ready to take control of your most powerful growth lever—pricing?

Checkout my featured section.

Founder and CEO

We help growth-stage B2B SaaS companies design the right pricing model to scale up

Ready to shift your pricing from guesswork to framework?

For the first time in my career, I lowered our growth forecast.

A few weeks into 2026, and I made a decision that felt counterintuitive: we're going to grow less this year. On purpose.

Here's my thinking.

I've been watching F1 lately, there's a scene in the new movie where Brad Pitt tells the pit crew: "Slow is smooth, and smooth is fast."

That line stuck with me.

What got us to 25 people and on the way to $10M bootstrapped isn't going to get us to the next stage. 

We're about to launch our first product. 
We're shifting from pure services to technology-enabled transformation.

That's a pivot. And you can't pivot at full speed.
The sports analogy holds up everywhere. 
Tennis, basketball, skiing, you have to slow down before you change direction. 

Get your balance underneath you. 
Build momentum. 
Then move.

Business is no different.

Here's what slowing down actually looks like for us:
→ Keeping quality at 98% satisfaction instead of chasing volume.
→ Reducing the number of engagement types. Fewer SKUs, less variability.
→ Saying no to projects that don't fit the middle of our fairway, even when the money's good.

Why? Because it's way harder to recover from a quality drop than a revenue dip. 
One bad quarter of delivery can undo years of reputation.

If you're considering a similar move, here's my framework:

1/ Identify the pivot. 
2/ Reduce variability first. 
3/ Protect what got you here. 
4/ Get alignment before you announce. 

The target is lower now. 
Less ambitious. 
But it's more achievable, and it sets us up for what's actually coming.

Sometimes slowing down is the most aggressive move you can make.

What's a decision you've made that felt counterintuitive but turned out right?

CEO of Pricing I/O • Award-Winning Author • Sought after Slayer of Bad Pricing

Everyone told me I was crazy to leave.

High-paying role at a PE firm. 
Direct access to a billionaire's inner circle. 
I was flying to portfolio companies on 24 hours notice, promising boards 18% revenue increase, and delivering.

But I was hitting airline status in two months flat, with a 4-year-old at home and a daughter on the way.

So I walked away and started Pricing I/O with a credit card and my savings.

That was the beginning. 

We're 25 people now, approaching $10M, and I still get a little stunned when I see how many seats we fill at team get-togethers.

I sat down with Mark Osborne, MBA, CEPA® on the B2B Growth Blueprint podcast and got into the full journey—the leap, how we actually scaled, and the leadership framework I use to run the business today.

Watch the full conversation:
→ https://skd.so/kPle2t

Most SaaS companies are pricing blind.

They copy competitors who are also guessing. 

They slap "AI-powered" on the pricing page and hope it justifies a premium. 

They build credit systems because everyone else is doing it, without understanding why credits work for Audible but might destroy their business.

And then they wonder why sales cycles drag, why customers push back on renewals, why the board keeps asking uncomfortable questions about unit economics.

We all have seen this pattern. Right?

→ The CEO who approved a "usage-based transformation" only to watch churn spike 40% because customers couldn't predict their bills.

→ The VP of Product who spent 6 months building an AI feature, then gave it away for free because nobody knew how to price it.

→ The founder who copied HubSpot's model without realizing HubSpot has 15 years of pricing iteration behind every decision.

Here's what I've learned: pricing isn't a simple math problem. 
It's a strategy problem disguised as a spreadsheet.

Is to understand the psychology behind why customers say yes, and structure their pricing to remove friction, not add complexity.

That's why I built this playbook.

A single page with the frameworks we actually use when we're in the trenches with B2B SaaS clients.

It's dense, but I can send you the high-res version. 
Comment "playbook" ↓

Today Satya Nadella leads a $3 trillion company with 228,000 employees.
But when he took over in 2014, Microsoft was stuck.

Losing mobile. 
Windows-obsessed. 
Falling behind Amazon in cloud. 
→ Market cap at $300 billion while competitors lapped them.

Most people expected a safe, incremental CEO.
Instead, Satya rewired the culture without burning it down.

Killed the stack-ranking system that turned teams against each other. 

Replaced "know-it-all" with "learn-it-all." 
Bet everything on cloud when Azure was still a distant second to AWS.

That bet alone now generates $75B+ in annual revenue.

But what I admire most isn't the strategy.

Technical depth. Emotional intelligence. Business instinct. 
Most leaders I've worked with have one, maybe two. Satya has all three, and deploys them quietly.

No theatrics. No ego. 
Just calm, steady decisions at a scale most of us can't comprehend.

He turned a legacy software company into the world's second-most valuable business by doing what every great leader must: read the room, commit to the shift, and bring the whole organization with you.

That last part, bringing people with you, is the hardest part of any transformation. Pricing, product, culture, doesn't matter.

I've seen it across hundreds of companies. 
The team leading the change matters more than the change itself.

A decade of selling B2B SaaS to PE firms teaches you something most pricing strategists never learn firsthand.

James joined us as a Pricing Strategist after years on the other side of the table.

If you've ever sold to PE, you know, they understand value as well as anyone, and they're ruthless about ROI.

That experience shaped how James thinks about pricing: always tie it back to quantifiable business outcomes. Never be vague about value drivers. Surface the trade-offs so clients can make better decisions, not just hear what they want to hear.

That mindset is exactly why we wanted him here.

What surprised him most about joining?
"We're a lean organization that punches well above its weight. Everyone on the team is incredibly sharp and moves fast."

He also mentioned being staffed on two client projects in his first week. That's not an accident, it's a vote of confidence in what a sales background brings to strategy work.

His mindset says it all.
Sales and product team alignment is the most crucial step in executing any pricing strategy.

Simple. True. And something most companies underestimate until it's too late.

Oh, and his karaoke song is "Escape (The Piña Colada Song)."

Make of that what you will.

Glad to have you on the team, James.

"Claude, let's code this SaaS, try not to hallucinate this time."

Honestly? We're getting there.

Recently we watched founders spin up products in weeks that used to take engineering teams 18 months.

→ Claude writes the code
→ Cursor ships the features
→ Bolt scaffolds the whole thing

But then the product is live, and someone asks: 
"What do we charge for this?"

That's where the vibe coding stops.
Because pricing isn't a code problem.

It's a "which metric scales with their success" problem.
It's a "what does your customer actually value" problem.
It's a "what does your board need this to say about your business" problem.

I've worked with 400+ SaaS companies. 
I've never seen a model spit out the right answer to those questions.

Not because AI isn't smart enough.

Because the answer lives in your customers, your data, your market, and someone who's seen enough patterns to know the difference between a pricing model and a pricing strategy.

That's still a human job.

If the pricing conversation is already giving you a headache, that's exactly what we do at Pricing I/O.

Let's talk.

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$285 billion wiped from software stocks in 48 hours.
The reason? Investors finally realized what we've been saying for 2 years, per-seat pricing breaks when AI agents replace human users.

Salesforce lost 7% in a day. ServiceNow, Adobe, Workday, all hit.

But here's what's wild: most SaaS companies I talk to are STILL running per-seat models with zero backup plan.

The "SaaSpocalypse" wasn't a surprise. 
It was a pricing model catching up with reality.

If your revenue model depends on headcount growth, and AI is shrinking headcount, and just like that: you have a monetization crisis.

"Rapid pricing experimentation" is dangerous advice.

I keep seeing the same pitch from billing platforms and entitlement tools: configure your pricing, launch a test, learn fast, iterate, repeat.

Sounds great in theory.

If you're selling a $9/month product to 100,000 users? Sure. 

Test away. Change that $9 to $9.99 and see what happens. 
You've got statistical significance and low stakes.

But if you're negotiating a $150K deal with a CFO at a Fortune 500?

→ Try explaining that your quote from last week was "just a test."
→ Try telling your sales reps that pricing changed again—third time this quarter.
→ Try building credibility when the prospect remembers seeing different prices six months ago.

Expertise over experimentation. 
That's my stance.

I'm not against testing. 
Testing is essential. 

But blind, rapid iteration creates more problems than it solves: internal confusion, external credibility risk, sales teams who don't know what to sell, and customers who don't know what to trust.

The answer isn't more speed. 
It's more intention.

Informed. Measured. Deliberate.

If your team is about to make a pricing decision too fast, that's exactly what we work through at Pricing I/O. Drop a comment or DM me.

Most SaaS companies blame product for churn.
But the data usually points somewhere else: pricing.

3 steps. 10 minutes. 
You'll know if churn is pricing-driven or product-driven.

Segment by cohort. Compare NRR vs. LTV. 
Read churn surveys for the real signals.

If customers say "can't justify cost", that's not a product problem.

2026 is the year the pack separates.
Not with a dramatic crash, more of a slow exposure.

On one side: companies that are deliberate about AI integration, honest about their metrics, and strategic about pricing.

On the other: the copycats. The aimless AI adopters. The ones chasing "Wishful Thinking ARR" with creative revenue definitions and 50x valuations.

The fallout we expected in 2025? 
I think it shows up in 2026. 

Here's why:
→ AI scrutiny goes up (budgets need justification now)
→ Differentiation pressure increases (the checkbox AI gets exposed)
→ Companies under pressure make desperate pricing moves

And here's the opportunity: the smart operators will start picking up technology AND talent from the companies that couldn't adapt.

Acqui-hiring in 2026 is going to be massive.

The question is: which side of the separation are you building for?

The best pricing leaders are readers.
And these are the 12 books every SaaS pricing expert should read.

Save this one to read later ↓

→ Month 1:
Monetizing Innovation
The Pricing Roadmap

→ Month 2:
Street Pricing
Blue Ocean Strategy

→ Month 3:
The Cold Start Problem
Hooked

→ Month 4:
The Go-To Market Handbook
The Lean Startup

→ Month 5:
Influence
Predictably Irrational

→ Month 6:
The Art of Pricing
The Subscription Boom

If you want to go deeper than books, this is what we work on every day at Pricing I/O.
Drop a DM and let's talk.

After working with 400+ SaaS companies, I see three types when it comes to AI integration, and only one of them survives the next 2 years.

Most companies say they're using AI.
Very few can explain why.

The difference isn't budget. It's not talent either.
It's whether AI is a checkbox or a strategy.

Some companies know exactly where AI fits in their pricing, packaging, and go-to-market. 

They've mapped the ROI. 
They've planned the process change.

Others bolted AI onto a roadmap with no monetization strategy behind it, and their boards are starting to notice.

Where does your company fall on this spectrum?

I almost lost myself to AI news last year.
Every day there was something new. 

OpenAI did this. Anthropic launched that. Google's catching up. Startups raising at 50x revenue.

I was reading everything. 
Trying to understand every perspective. 
Watching every announcement.

And then I noticed something: 
I was paying less attention to my team.

The conversations were shorter. 
The check-ins were surface-level. 

I was physically present but mentally somewhere else, chasing the next headline, the next hot take, the next "you need to know this" thread.

FOMO was pulling me away from the work that actually matters.

Here's what I've been obsessing over instead: clarity.

Not mission statements. Not OKRs. 
Actual clarity, where your team can articulate what they're doing, why they're doing it, and how it connects to where you're going.

It sounds simple. 
It's brutally hard.

I've started asking my direct reports one question:
"Do you understand what we're doing and why?"

If they have a different point of view, I want to hear it. 
If they're confused, I need to know. 

A 10-second answer tells me everything: 
"Yes, I get it, I think we're going the right direction." 

Great. But more often, that question opens a door to something I was missing.

Here's my test:
→ If you have 5 direct reports and all 5 say the same thing about your direction—high five, you're leading well.
→ If all 5 have completely different views of what you're trying to do? That's not a them problem. That's a you problem.

People can feel when you're paying attention. 
They can also feel when you're not.

Forget FOMO. Focus.

2026 isn't the year SaaS dies.

It's the year people finally realize AI needs SaaS as much as SaaS needs AI.

Distribution, data, workflows, customer trust, none of that disappears because ChatGPT exists. 

But the SaaS companies scrambling to slap "AI-powered" on their pricing page without rethinking what they actually deliver? Those are the ones in trouble.

We've watched this play out across hundreds of companies.

Companies treating AI like a feature are missing the real forcing function, the question they've been avoiding for years: what outcome are we actually selling?

Seat-based pricing made sense when humans were the unit of consumption. 

When AI agents are doing the work, you're not selling seats anymore, you're selling results, throughput, outcomes that scale beyond headcount.

Most SaaS companies haven't touched their pricing model in years. 
AI just made that procrastination expensive. 

→ Boards are asking harder questions. 
→ Valuations are getting squeezed. 
→ And every month without a clear answer is revenue left on the table.

To surf the hype in 2026, get deliberate about monetizing what AI actually delivers.

That's what we spend every day working on at Pricing I/O, and the urgency we're hearing from founders and boards right now is unlike anything from the last few years.

The window to get ahead of this is open. It won't be for long.

I had to look in the mirror and ask myself a hard question.
Am I drinking my own Kool-Aid?

I've sat in rooms with founders who had their goggles on. 
Convinced they're smarter than everyone. 
Convinced the market is theirs for the taking.

And I've watched them fail.

Smart. Ambitious. Dedicated. Motivated.
Still failed.

So when I started building our new product, I made myself three promises:

1/ Assume there won't be a warm reception.
2/ Assume my assumptions are wrong.
3/ Assume this is a longer journey than I think.

Mike Tyson said it best: 
"No plan survives the first punch in the face."

We're going to get punched in the face. 
Every product does.

The question isn't whether it happens. It's how we react.

So instead of chasing a blowout launch, I'm building systems. 

Feedback loops. 
Prioritization frameworks. 
Quick cycles to learn and pivot.

How do I figure out how to figure out stuff?

That's the real question.

If we get a blowout launch? Hallelujah.

But I'm planning for the worst and hoping for the best.

Building something new is freaking hard. 
And it's full of trapdoors.

What's one assumption you're making about your business that might be wrong?

I think Mark Benioff is overrated.
I'll say it out loud.

Look, Salesforce is the godfather of SaaS. 
Many people give it that title, and it's earned. 

They pioneered cloud software. Built a $40B+ company.

But I think that was more Mark's team and the great people he had around him than Mark himself.

He's good at sales. He makes smart decisions. He’s a pioneer.  
I'm not saying he's bad.

But I lost a lot of respect for him when he said AI would be easy. 
That he could sell the world on his AI overnight.

That's obnoxious.

AI isn't easy. Anyone who's actually building with it knows that. 
Anyone who's helping companies integrate it knows the complexity, the change management, the friction.

Saying "AI is easy" tells me you're selling, not building.

I'd rather follow leaders who are thoughtful than leaders who are loud.
Give me Satya Nadella's calm over Benioff's bravado any day.

Pricing for the wrong thing is one of the most expensive mistakes I see.
(And still most companies miss this completely)

In a PLG motion, pricing does the heavy lifting early. 
→ It's the packaging, the free tier boundary, the upgrade trigger that converts users before a human ever gets involved.

In a sales-led motion, pricing shows up late. 
→ It's a negotiation lever, a discounting battlefield, and often an afterthought bolted onto whatever the rep promised on the call.

I've seen 400+ SaaS companies try to use the same pricing playbook for both motions. 

It doesn't work, because the moment where pricing creates or destroys value is fundamentally different.

The consequences cascade:
→ Your packaging
Does it need to sell itself on a webpage, or does it need to survive a 6-month procurement process?

→ Your discounting exposure
PLG has almost none. Sales-led can hemorrhage 20-40% if there are no guardrails.

→ Your expansion path
PLG expands through usage and upgrades. Sales-led expands through rep-driven upsell conversations.

→ Your pricing team's focus
Optimizing conversion rates vs. optimizing deal structures.

Neither is wrong. 

Your go-to-market motion dictates where your pricing has leverage.

If you're not sure your pricing is built for your motion, that's the first thing we diagnose at Pricing I/O. 

To book a free discovery call drop me a DM.

Most companies wait until something breaks to revisit pricing. 
Here are the 7 signals it's time to take a closer look.

In this video I'll talk you through:
→ Triggers that indicate pricing needs attention
→ Why "not the right time" is costing you money
→ Common patterns from 400+ SaaS companies

#saas #pricing

When people ask who I'm being inspired by, I don't have a good answer.

I never looked for figures to follow.
No heroes. No role models I'm trying to copy.

Just me, trying to make more good decisions than bad decisions. 

Keep learning forward. 
Treat people right.

That's it. That's the whole philosophy.

I like outside perspective. I get inspired by others. But what works for them doesn't necessarily work for me.

And I think that's okay.

Not everyone needs a leader to chase.

Some of us just need to stay honest with ourselves about where we're strong and where we're not.

Be introspective. 
Be blunt with yourself. 
Make trade-offs intentionally.

In the end, business is all about getting people to do stuff for you. 

→ Engineers to build for you
→ Employees to work for you
→ Customers to buy from you

Once you figure out how to do that, there's really no limit to what you can do.

No heroes required.

SaaS Founder: Stop copying competitor pricing pages.

That pricing page you're copying was built for a completely different business.

Here's how to fix it.

Watch more pricing insights here https://skd.so/E9ur5M

Jerry Macnamara

Helping CEOs Scale without Stress | Franchise 500 (2x), Inc500 (2x) & Biz Journal Fast 50 (3x) + Trend Best Places to Work | Ultimate CEO | Proving Good Guys Finish 1st since 1974 | Host "Best Places to Lead"

Your business is working, but can it do more?
 
Like most business leaders, you've likely spent sleepless nights obsessing over your company's future. You’ve closed your office door, scratched your head, and wondered what to do next.

You're anxious about losing your best employees while regretting not letting go of underperformers sooner.

Does this sound at all familiar?
Feel Trapped: You lack a clear execution plan and are overwhelmed by daily crises, running from fire to fire.

Employee Frustrations: Miscommunication and unclear directions leave you shouldering the burden alone.

Unmanageable Growth: Scaling your business feels impossible without the right systems and processes.

Fear Over Joy: Constant fear paralyzes and frustrates you, stealing the joy from your work.

It doesn't have to be this way. With a proven track record leading award-winning companies across multiple industries, I’ve developed a system that drives success. 

Here are some of the results I’ve produced:

Franchise Growth: I helped grow a franchise company from $5MM to $15MM in just 18 months, earning a spot in the Franchise 500 (2x).

Manufacturing Excellence: I transformed a forty-year-old manufacturing company to achieve a 98% on-time delivery rate.

Successful Exit: I started, scaled, and successfully sold an internet business.

Construction Leadership: I led a construction company from $7MM to $30MM in three years, making it to the Inc 500 (2x) and Best Places to Work.

Here’s the truth…
Your product doesn’t matter. 
Your service doesn’t matter. 
Your industry doesn’t matter. 
Your channel doesn’t matter. 

Your business is widgets, plain and simple…  and the only thing that matters is your leadership approach.

However, on-the-job training is stressful and costly, eating away at your opportunities and profits.
If you want to scale without stress, join our exclusive mastermind of high-growth B2B CEOs. Learn from my experience and avoid the pitfalls that can derail your progress.

Book a call: https://calendly.com/jerrymacnamara/25-minute-zoom

Business is not only the economic engine of the world, but it is also the engine of cultural change. Our mission is to positively impact a healthier, happier world where people live life on their terms, with intention, because of better business. By equipping our CEOs with frameworks to lead and a support system to help, businesses will fulfill the promise to their customers, vendors, and employees.

ProvenChaos. Weird company name, right? 

Let me explain because you’ve probably experienced it yourself.

You’ve Proven there is a pain point you can solve in the market, but you feel in Chaos because your systems, people or processes haven’t kept up. Or, maybe you feel in chaos personally because the business is stealing all your energy and time away from your family, so there is a lack of fulfillment despite your success.

That’s ProvenChaos.

Have you ever had that ProvenChaos feeling? I bet you have.

Learn how we can help at ProvenChaos.com

“I’m basically doing half their job. And, I’m rewriting the other half.”

I recently spoke with a CEO who was at their breaking point. They weren't dealing with a "bad" person, but they were dealing with a misplaced leader. This leader, let’s call them a VP of Operations, was checking the boxes, but the output was mediocre at best. The "strategic plans" were clearly just copy-pasted prompts from a chatbot. The judgment calls were consistently off. The team had stopped looking to them for guidance.

The CEO was exhausted. Every evening was spent "fixing" things that should have been handled in the first place.

This is the High Cost of Mediocrity.

As leaders, we often fall into a classic trap: we mistake conflict avoidance for employee development. We tell ourselves:

"Maybe if I just give them one more framework..."
"I haven't coached them enough on this specific task..."
"I don't know how the rest of the team will react if I let them go..."

But while you’re "developing" someone who isn't a fit, you are paying a massive "Tax" on your entire system.

1. The Trust Tax
When a key leader loses the organization's trust, the CEO loses it too. If the team sees you tolerating low-effort, AI-generated slop or poor judgment, they don't blame the underperformer. They question your standards.

2. The Velocity Tax
If you have to micromanage a senior leader, you aren't a CEO anymore; you’re a high-priced editor. Every hour you spend fixing their work is an hour you aren't spending on the company's future. You unwittingly become the bottleneck.

3. The Peter Principle Trap
Sometimes, you’ve promoted someone to their level of incompetence. It’s not a moral failing on their part, but it is a leadership failing on yours to keep them there. You cannot "coach" someone into having the fundamental judgment required for a high-level role.

👉 The Hard Truth: Coaching is for people with the right DNA who need new skills. It is NOT a rescue mission for a lack of discipline or poor instincts.

If you find yourself dreading a Senior Leader’s updates or "double-checking" every single thing they touch, the decision has already been made. You’re just waiting for the "courage" to catch up to the "reality."

Stop being an expensive safety net. Give yourself permission to act. The rest of your high-performers are waiting for you to do it.

In fact, you owe it to them to act quickly and decisively now that you see it.

You teach your kids to be kind. 

Then you walk into work and reward the loudest voice in the room.

🪞 We all know the speech. "Be kind. Be sweet. Add joy to the world." We rehearse it at dinner tables. We repeat it at drop-off. We deeply believe it when we say it.

Then Monday morning hits. Someone sends a passive-aggressive email to the whole team. Someone throws a colleague under the bus on a call. Someone gets promoted because they "drive results," even though half the department dreads working with them. 

And nobody says a word.

We've built a world where you can call someone an ahole without ever looking them in the eye. Hide behind a screen. Hide behind a Slack message. Hide behind "just being direct." From my seat, the distance between what we say matters and what we actually tolerate has never been wider. 

🙋‍♂️ Guilty. Working on it.

This isn't a society problem. This is a leadership problem. Every company has values on the wall. Most don't enforce those values when it COSTS something. When the top performer is also the most toxic person on the team, you find out what a company actually believes. Not what it says it believes. What it funds. What it promotes. What it lets slide.

I've watched CEOs agonize over teaching their ten-year-old about accountability while simultaneously avoiding a hard conversation with their VP of Sales. Same person. Same week. The gap isn't ignorance. It's exhaustion. It feels naive to hold the line when the world around you seems to reward people who don't.

That weariness is real. I get it. But it's also the trap.

🔥 The moment you stop living your values because "that's not how the game works," you become the thing you're complaining about. Your kids don't learn values from your words. They learn them from watching what you do when it's inconvenient. Your team works the same way.

Civility isn't soft. It's a standard. And standards only exist if someone is willing to hold them when it's expensive.

This week, find the one place where your behavior doesn't match what you'd teach a twelve-year-old. Fix that one thing. Not because the world deserves it. Because your team is watching the same way your kids are.

PS - I'm talking to my kids this week about one of my favorite words, "contribute." There are a million ways to contribute if you pay attention and stay aware - and don't expect more from others than you expect from yourself. 

PPS - Same for my team.

I spent most of my 20s trying to be the smartest person in the room. 

It almost killed me.

This flawed approach is one of the major reasons I ended up on a hospital gurney at 26. High growth. Raising capital. Enormous stress. I realized my thinking was ego-driven, not sustainable, and unhealthy for the business.

🤯 Yet, it felt good. #weird

I didn’t have to know it all. But that was my view as a leader. I had to have a point of view, stay curious as all get out, and move from feigned “knowing” to “voracious” learning. Curiosity is a superpower.

The change I adopted?

Stop presenting. Start proposing.

Instead of always handing down a "finished" document, I’d stay humble and say:

"Here is what I’m thinking. I know it’s about 60% there. Where am I wrong?"

When you treat your people as smart thought collaborators, you elevate engagement, reduce stress, and devise better approaches. The people closest to the problem almost always have better ideas.

But you have to go first to create gravity for the topic… as the leader, you have to keep your head above the business landscape.

My earliest mentor drove the second part of this strategy into me:

✍️ It doesn't exist if it's not in writing.

If a strategy, decision or process is not written, it cannot be examined, challenged, aligned to, or executed consistently. Clarity requires explicit articulation. Otherwise, it's an elusive illusion.

Tribal knowledge is the enemy of scale. It’s okay to publish Work in Process. It’s not okay to leave a meeting with lots of tribal knowledge and ideas that weren’t captured.

Clarity demands a pen. It accelerates the iteration process. 

Favor clear(er) trajectory over theoretical completeness. Give direction so teams can act decisively…and learn. Waiting for perfect information to write the strategy creates paralysis and erodes momentum.

Learn from my mistakes. I made them for you.

#15Forward Don't sleep on this one.

Time is the atomic unit of productivity.

Your whole life comes down to how you spend your time. 

Most people float like a leaf in the wind

Then wonder why success is always out of reach.

Here's what you need to do differently to align your week and drive productivity with #15Forward: 

1️⃣ Dedicate 15 Minutes on Sunday: Set aside just a quarter of an hour every Sunday. This small investment of time can revolutionize your week.

2️⃣ Look 15 Days Ahead: Scan your calendar for the next two weeks. This foresight allows you to anticipate and prepare, rather than react.

3️⃣ Align with Your Goals: Scrutinize each appointment and task. Does it align with your North Star and your ultimate goals and vision? If not, eliminate it. Period.

4️⃣ Confirm, Cancel, Create: Confirm essential meetings, cancel what’s no longer relevant, and create white space for strategic thinking. This is where the magic happens. Make space for the innovation and problem-solving you create.

By implementing #15Forward, you're not just planning your week; you're strategically aligning your time with your most significant objectives. It's about making every hour count towards your success. 

Try it this Sunday and feel the difference. Friday's success will thank you!

Leaders should always look for unfair advantages.

Becoming successful doesn't just happen. It is a design choice.

An unfair advantage in my work is brain.fm. It's a science-backed app that uses AI-generated, functional music to alter brain states for enhanced focus, relaxation, meditation, or sleep.

Here are the 3 ways I create leverage in my work:

1️⃣ During the morning, I use the meditation function. Off to a gold medal start.

2️⃣ During the day, I flip on the focus mode to slip into deep work where time evaporates and ideas come spilling out of my fingertips.

3️⃣ At night, I turn on Deep Sleep. If you know me, I don't require much sleep. And, I can pretty much fall asleep anywhere. Yes, anywhere. (✅ NFL Stadiums. ✅ House parties. ✅ Bars. ✅ Movie theaters. ✅ Middle of a conversation) But there is something about the neural beats from brain.fm that gives me deep, restful sleep.

I've been using Brain.fm for years now. It's part of my secret-weapon arsenal that gives me an unfair advantage. 

You should check it out.

A slow "maybe" does far more damage than a fast "no" ever will.

Most leaders think they're being thoughtful. Careful. Measured. They sit on decisions for weeks. They ask for one more data point. They table it for the next meeting. Then the next one. They think delay is diligence.

It's not. It's cowardice wearing a suit.

🔥 The real cost nobody measures

I was coaching a CEO last year. Her VP of Sales had proposed a new comp structure. Good proposal. Clear thinking. The CEO said, "Let me think about it." That was in March. By June, nothing. No "yes." No "no." Just silence. That VP stopped bringing ideas. Stopped pushing. Started updating his resume. He was gone by August.

The CEO didn't reject his idea. She did something worse. She made him wait in a room with no door.

That's what a long maybe does. It doesn't just stall a decision. It stalls a person. It tells your best people that their energy doesn't matter enough to warrant a response.

⚡ Fast "Nos" are a gift

When you say "no" quickly, your team grieves for about 15 minutes. Then they redirect. They find another path. They move. A fast no is clean. It respects the person enough to tell them the truth. It frees up their brain to solve the next problem.

A long maybe? That keeps them checking their email. Rethinking their pitch. Wondering if they did something wrong. You haven't saved their feelings. You've trapped them in limbo and called it kindness.

I've watched this pattern at dozens of companies. The leaders who move fast, even when the answer is no, have teams that bring more ideas, not fewer. The leaders who sit on decisions have teams that stop asking.

🎯 Pick a lane today

Pull up your open list right now. Find every open request that has been sitting for more than 2 weeks. Every proposal you haven't responded to. Every "let me get back to you" that you never got back to.

Say "yes" or say "no." Today. Not next week.

Your team doesn't need you to be right every time. They need you to be clear. Speed of decision reflects trust. 

And a long maybe is just a no that hasn't found its spine yet.

Your team went home last night and told their families they had a good day at work.

They have no idea if that's true.

🎯 Here's what "good day" actually means to most employees.

It means nobody yelled at them. It means their boss seemed in a decent mood. It means they got through eight hours without conflict. That's the bar. That's what they're measuring against.

Not outcomes. Not targets. Not contribution. Just the absence of bad feelings.

I call this “The Good Day Fallacy.” And it's running your company right now.

Someone goes home tonight and looks out back up the waterway. Their spouse asks the question we all get asked. "How was your day?" They say great. What they actually mean is: I was treated with respect today. Nobody made me uncomfortable. The meeting wasn't awkward.

What they are NOT saying is: I needed to produce four widgets today and I put out six. I crushed it for the company.

They can't say that. Because you never gave them a number of what good looks like.

🔍 This is the blind spot most leaders miss completely.
Your culture feels pleasant. People seem happy. Turnover looks manageable. So you assume things are working.

But pleasant is not a performance driven culture. And happy without a scoreboard is just comfortable.

When your people define a good day by social temperature instead of measurable output, you have a performance problem dressed up as a culture win. Nobody is losing. But nobody is winning either. They literally cannot tell the difference.

That's not their fault. That's yours.

🔧 The fix is simple
Every role needs a number, so your people know if they’re winning and contributing. Not a vague responsibility. Not hours in a seat. A number. Something your people can count at 5pm and know, without asking anyone, whether they won the day.

Four widgets. Six calls. Two proposals out the door. Whatever it is for that role in your business.

When the standard is clear, "good day" changes meaning overnight. It stops being "nobody was mean to me" and starts being "I performed. And, it’s meaningful and matters. I'm valuable."

Right now, pick one role on your team. Define what winning looks like for that person. Not a feeling. A count.

If you can't do that in 60 seconds, your whole team is going home tonight, calling it a good day. And you have zero idea if it actually was. 

But, your Profit & Loss statement will…

PS - It's not "one or the other." It's both. There should be a kind culture. And, there should be clear performance standards. Don't confuse the message.

Most people are still planning when they should already be failing.

I have a client who is writing a book. An early reviewer noted that the proposed work schedule from the book isn’t feasible. Says it's unrealistic. Says not everyone can operate like that. Fair enough. But then you dig in, ask a few more questions, and realize he's not rejecting the schedule. He's rejecting the reps. He wants the outcome without the awkward, ugly, inefficient phase where you don't know what you're doing and it shows.

Everything is messy early stage. What did you expect? Lean into it.

Every day you don't know something in your business, you're paying a tax. Call it the ignorance tax. You're paying it in bad hires, slow decisions, missed margin, rework. The only way to stop paying it is to shorten the distance between not knowing and knowing. And that distance is measured in reps, not in thinking.

I watched this play out on a fishing boat. My friend had never fished before. Lost his bait over and over…like 32 times in a row. The captain was making fun of him. Didn't matter. He kept saying the same thing. "Fellas, I just need more reps." No frustration. No existential crisis. No putting the pole down. By the afternoon, he was catching fish like he'd been doing it for years. That's the craftsman's mentality. It’s expecting to get your teeth bashed in because you lack the skill or the context to do better. Not talent. Not strategy. Just a willingness to be bad at something long enough to get good at it.

The objection is always the same. "That pace isn't realistic for me." And the answer is always the same. Fine. You can take longer. But understand what you're choosing. You're choosing to pay the ignorance tax for more months. The reps don't shrink. The timeline just stretches.

All choices have consequences: good or bad.

This isn't about grinding yourself into dust. Keep climbing at the gym. Mow your lawn if you love it. But stop confusing comfort with readiness. You don't think your way to competence. You act your way there. And the people who resist that aren't protecting their well-being.

They're protecting their ego from the early phase, where they look like they don't know what they're doing.

Because they don't…yet.

10% improvement per week. 📈

Jason Calacanis reports that's the current rate of improvement he's seeing in OpenClaw. For context, a high-performing human employee aims for 10% per year.

Pretty mind-blowing.

The Citrini Research report dropped a bombshell this week, predicting that this "Velocity of Capability" could lead to massive white-collar displacement and market instability.

I told Rachel Barnes, "From my seat, I think they're right."

We are seeing AI that: 
✅ Acts without constant direction (OpenClaw). 
✅ Codes its own future (OpenAI Codex). 
✅ Solves real-world tasks autonomously.

The Window of Opportunity: There is still a massive amount of leverage available to the "little guy." But you have to move. Luck favors the bold.

Attack previously "unsolvable" problems.
Pivot away from old patterns and ignore sunk costs.
Break down silos with improved dialogue to improve creativity.

The leverage is there. Grab it before it becomes a constraint.

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The Battle

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