Chief Milestones
How real operators build durable businesses under real constraints; capital, regulation, systems, and life.
Chief Milestones is a video podcast breaking down the decisions, trade-offs, and structures behind businesses that actually last, told by people who’ve had to run them, not just start them.
This isn’t about shortcuts or hype.
It’s about how businesses are really built when real life is involved.
Chief Milestones
Most doctors, when their training fails them, double down on the training.
Dr. Nanda did the opposite.
When his son was diagnosed with autism in 2015, he was a working oncologist - an expert in blood and cancer medicine. And he had no answers.
What happened next wasn't just a health journey. It was a full deconstruction of how he thought about disease, causation, and what medicine can and can't prove.
New episode is live. This is Part 1 of our conversation with Dr. Nanda - and it goes places most medical conversations won't.
1 day ago | [YT] | 0
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Chief Milestones
Not Every Business Starts With Inspiration.
Some Start With Exclusion.
This Episode Examines:
• Toxic Work Environments
• Structural Isolation
• Building Alternative Systems
Some People Don’t Fit The System - So They Build One.
Watch The Full Conversation → Alex Morgan Part 1
#ChiefMilestones #SystemDesign #Entrepreneurship #WorkplaceCulture #Operators
1 week ago | [YT] | 0
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Chief Milestones
Most People Think The Spreadsheet Is The Skill.
It’s Not.
The Skill Is Turning Risk Into Leverage Through:
• Knowledge
• Operations
• Systems
• Repetition
This Episode Explains Why Experienced Operators Can Underwrite What Others Avoid.
Watch Sujay Part 2 For The Full Breakdown.
#ChiefMilestones #DecisionQuality #Operators #RiskManagement #SystemsThinking
1 week ago | [YT] | 0
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Chief Milestones
This episode isn’t for kids. It’s for founders who forgot where their people-pleasing instincts started.
An 8-year-old explains why he says yes when he doesn’t want to - and it’s more operational than you think.
Watch the full conversation.
2 weeks ago (edited) | [YT] | 1
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Chief Milestones
Some conversations aren’t for discovery.They’re for alignment.
This clip closes Episode 5 by reframing: success, capital, and the moment real change happens.
If you haven’t watched David Part 1 to 4, that’s the entry point.
3 weeks ago | [YT] | 0
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Chief Milestones
Most people treat structure like a morality test: “If I had more discipline, I’d be fine.”
Wrong frame. Energy is finite. Life is variable. So systems exist to protect capacity.
#CapacityThesis #StructureIsProtection #EnergyIsFinite #SystemsOverWillpower #SustainableSuccess #ChiefMilestones
4 weeks ago | [YT] | 0
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Chief Milestones
Content doesn’t fail because people lack motivation. It fails because they ignore capacity.
David Part 3 breaks down why content only works once it’s treated like a system - not a grind.
1 month ago | [YT] | 0
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Chief Milestones
If motivation were enough, consistency wouldn’t be the hardest part.
This clip explains why systems - not grit - are what actually survive over time.
1 month ago | [YT] | 0
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Chief Milestones
Scale doesn’t break above ground. It breaks below it.
This episode shows why infrastructure - not deals - determines how far a business can actually grow.
1 month ago | [YT] | 0
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Chief Milestones
Most real estate advice assumes buying is the hard part.
This episode shows what happens when buying stops working - and the model has to change.
Part 1 of David Graber’s series is live.
1 month ago | [YT] | 0
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