The Scaling Paradox
Episode Guest – Jhana Li
In this episode of The Scaling Paradox, Jhana Li (Founder of Spyglass Ops) breaks down why most scaling founders are stuck not because they lack grit, but because their strategy is broken. She’s helped over 200 B2B startups and agencies uncover operational debt, simplify strategy, and rebuild margin by fixing what’s upstream.
If you’re stuck in the $50K–$300K MRR stage, constantly solving the same fires, or questioning why growth feels harder, this episode hands you the audit, the framework, and the mindset reset you need.
How to tell if your vision and model are misaligned
The 3-layer framework to fix fragile operations: Strategy → People → Systems
Why your team might be executing chaos (and how to realign them fast)
How to self-diagnose with the Spyglass 5-Point Audit
What to do when profit flatlines despite growth
00:00 – Open
“Most founders are playing business on hard mode.”
01:00 – Jhana’s Journey
From vanlife COO to fixing ops for 200+ founders scaling lean teams.
05:00 – The Pyramid Framework
Strategy: clarity, leverage, outcome alignment
People: org design, leadership layers, trust-building
Systems: automation and support that scale with less
💡 Case: $120K MRR agency with no strategic clarity → 28% margin lift in 90 days.
10:00 – Diagnosing Strategy Failures
Vision Mismatch: you’re building a job, not a business
The Operator Void: founder buried in delivery = no scale
🛠️ Fixes: rewrite the north star, eliminate low-ROI services, place internal operators
25:00 – The Spyglass 5-Point Self-Audit
Rate your business from 1–5 across:
Vision Clarity – Can you explain where you’re going in one sentence?
Leverage Map – What are your three highest-ROI activities?
Role Alignment – Are your A-players in the right seats?
Operational Gravity – What breaks if you take 30 days off?
Strategy Simplicity – If it’s not simple, it won’t scale
"Below 15? You’re scaling on hard mode."
40:00 – Playing Business on Easy Mode
What happens when you remove 40% of your initiatives
The difference between grind culture and leverage culture
Why doing less = scaling more
55:00 – Final Takeaways
Everything breaks without strategy clarity
SOPs and systems won’t fix the wrong business model
Profit hides in the operational gaps you’re not seeing
"Growth feels like quicksand when your strategy's unclear."
"Leverage is a ratio. Most founders are stuck chasing volume."
"If your systems break when you step away, they weren’t systems. They were duct tape."
B2B founders scaling
Agency owners stuck in team chaos or delivery
Leaders trying to fix margin problems with tools or talent (not strategy)
Founders overwhelmed by growth that doesn’t feel sustainable
Keywords - scaling a business, strategy audit, operations framework, founder bottlenecks, business leverage, operational debt, agency growth, systems thinking, team alignment, MRR plateau, margin growth, time freedom
Calm Scaling. Founder Burnout. Agency Growth. Leadership Breakdown. Culture Reset. Operational Excellence.
In this Episode -
Dee Dang talks about scaling to 120 people before burning out and being forced to rebuild.
What you'll learn:
• How to find your ideal pace
• How to run time and energy audits
• How to rebuild culture and ownership
• How to scale without breaking yourself or your team
Scaling a business often looks like success from the outside. Revenue climbs. Headcount grows. Client wins stack up. But inside the mind of a founder, the path upward can feel like suffocation. This episode of The Scaling Paradox dives into the truth few leaders will ever admit publicly. Scaling does not break a company. Scaling exposes what is already broken. And for Dee Dang, co founder of the performance growth agency Right Hook, the moment of reckoning came fast and hard.
In this deep dive conversation, Dee shares how he scaled his agency from early Facebook ads work into a full service DTC growth partner supporting seven and eight figure brands. At its peak, the agency hit 120 employees. The demand was real. The growth was real. The pressure was real. Then the cracks appeared. Quality dipped. Middle management bloated. Systems fractured. Culture drifted. And a failed delivery in front of Shopify’s president exposed the underlying truth. The “sauce” that made the agency great had diluted.
This episode is a full founder level masterclass on rebuilding after scaling too fast. Dee dismantles the myth that more hustle is the answer. Instead he introduces the Calm Scaling framework. A leadership philosophy rooted in flow state fundamentals, Lean thinking from Toyota, continuous improvement, OKRs, time and energy audits, and the idea that pace is a strategic lever not a badge of honor. If founders do not define intensity, intensity will define them.
You will learn how Dee cut his team from 120 to 60 without killing morale. How he rebuilt culture through a single person at a time instead of town halls. How he used Slack threads to spotlight learning, not punish failure. How he restored ownership by pushing teams to share public learnings and sunshine failed projects. How he used Lean tools like A3 thinking, Gemba style observation, constraint mapping, and operational diagnostics to restore organizational clarity and flow.
You will hear what burnout looked like from the inside. How cortisol spikes, guilt, and performance decline created a loop of overwork. How the gym bro analogy explains why founders confuse intensity with identity. How to audit your time and energy to discover the work that drains versus work that drives outcomes. And how to calibrate your personal pace with your organization’s actual capacity. Dee explains why founders lose themselves when scaling and how to reclaim direction, joy, and clarity.
The episode dives into talent density, cultural reset tactics, Dunbar’s number, psychological safety, recognition loops, internal influence mapping, and how to build viral adoption for new behaviors. Dee shares why ownership must replace process worship. Why outcomes must sit above frameworks. Why great leaders do not mimic pace, they architect it. And why scaling sustainably means training like an athlete. Push with intention. Recover with intention. Build an engine for the long run.
If you are a founder, COO, agency owner, or operator scaling from 1M to 30M, this episode is essential listening. It will challenge your assumptions about growth, intensity, leadership, team design, and cultural alignment. It will give you practical tools for diagnosing problems, setting pace, and rebuilding organizational systems without burning out your team or yourself. And it will remind you that calm is not the opposite of ambition. Calm is the multiplier of ambition.
You’re scaling. Revenue’s up. The team is growing.
But instead of momentum, you’re feeling drag.
What gives?
Here’s the truth most founders miss: your biggest scaling bottleneck is people — not systems, not strategy, not market conditions.
And the longer you avoid it, the more it costs: in momentum, morale, and margin.
🎙️ In this episode of The Scaling Paradox, we sit down with Angelina Galindo former enterprise exec turned leadership coach — to uncover what’s really breaking companies at $80K–$150K MRR and beyond.
With decades of experience in billion-dollar B2B deals, Angelina now coaches founders through the invisible breakdowns that stall growth:
Mis-hires and weak onboarding
Late firing decisions
Burnout from over-functioning leadership
Confusion between loyalty and competence
💥 What we cover:
• Why hiring too slow kills growth — and how to fix your hiring process
• The 1:1 framework that transforms updates into ownership
• How to identify misaligned team members early
• The right way to fire someone without guilt or delay
• How to coach mid-level leaders to make decisions without you
• Angelina’s 3 founder rules to scale sustainably (and stay sane)
🔊 Standout Clip:
“You already know who needs to go.”
It’s not just a gut feeling — it’s your unspoken data.
Ignoring it? That’s how teams stagnate and founders spiral.
🧠 Full Episode Breakdown
ACT I — The Spark
Angelina dominates in enterprise sales, then walks away to rebuild life on her own terms. From scuba diving to spirituality, she learns the deeper game: scaling is always about people.
ACT II — The Break
Coaching founders, she sees the same trap: over-functioning CEOs, loyal but ineffective teams, and no one taking ownership. Leadership debt builds. Growth slows.
ACT III — The Shift
She lays out her leadership operating system:
Create success paths
Shift 1:1s from status to strategy
Exit fast, but with grace
This isn’t theory — it’s the manager reset every founder needs.
ACT IV — The Wisdom
Burnout doesn’t come from doing too much. It comes from staying misaligned.
Angelina’s 3 rules:
Always show up.
Always upgrade.
Get over it.
Because growth doesn’t care how you feel — but your team reflects it.
🎧 Listen if you’re a founder who:
• Feels friction in your leadership team
• Is stuck in the weeds and can’t let go
• Needs to fix culture without slowing down
• Is scaling a SaaS, agency, or service business past $100K MRR
This isn’t a playbook.
It’s a mirror.
🔥 Tap play on “People Problems: The #1 Scaling Bottleneck Nobody Prepares You For”
with Angelina Galindo — and start building a team that actually scales with you.
👇
Follow the show. Rate it. Share it with a founder stuck in team chaos.
You don’t need more hires, you need sharper ops.
Jai Dolwani scaled 3 businesses without a single full-time employee. In this episode, he breaks down how.
You’ll leave with:
• The 3-question freelancer test
• Roles you should never outsource
• Why most hiring advice leads to bloat
This isn’t theory, it’s the lean ops playbook.
You scaled. You built the thing.
But now… you’re not the same person anymore.
Andreas Pettersson has reinvented himself more times than most dare:
• Factory line → CEO of 150• Burnout → mission-led founder
In this episode, we unpack what most founders ignore:
You can’t scale your company if you never reinvent yourself.
You’ll leave with:• 3 founder reinvention patterns• How ADHD became his edge• The habit that changes everything
Mitch Barham scaled his agency to $1M ARR in 12 months, then nearly burned it down.
In this episode, we unpack burnout, bottlenecks, and “Brad,” the alter ego of self-sabotage that almost wrecked it all.
You’ll learn:
• When to hire a COO• How to spot burnout early• Why 80% from someone else is enough to scale
You’re scaling. Revenue’s solid. But something feels… off.
Executive coach Michele Jewett has helped 100s of founders break the burnout-success paradox. She shares tactical tools to realign your vision, reclaim your joy, and lead without losing yourself.
Leave with: a “joy meter” audit, the “second arrow” reframe, and AI prompts to uncover your true values.
For founders scaling fast and feeling stuck anyway.
Chris Lang scaled Fresh Chile to $10M+ on Shopify. Then he realized he was the bottleneck.
In this episode, he breaks down how he rebuilt everything around three core levers: consistency, communication, and creativity.
You’ll learn:
How to spot when you're the bottleneck (and what to do about it)
The 3C framework Chris uses across brand, SaaS, and agency
How to delegate without losing visibility or control
Why narrative isn't just brand, it’s an ops weapon
Listen now if you're scaling and still too deep in the weeds.
Phoenix Ha on Doubling Revenue by Cutting 80% of Her Users
What if the thing breaking your growth… is the customer you’re trying to serve?
Phoenix Ha, co-founder of AdBeacon, hit a revenue plateau. The product worked. The users were active. But something wasn’t clicking.
In this episode, Phoenix shares the ruthless pivot that unlocked their next stage of growth: killing the free trial, cutting off 80% of users, and going all-in on the 20% who actually mattered.
You’ll hear:
Why free trials are ego traps (and what to do instead)
How picking the wrong ICP nearly stalled momentum
The quiet cost of building a brand that no longer reflects you
This is what happens when a founder stops chasing growth hacks—and starts building for the customer who actually drives value.