Chief Milestones
Chief Milestones is a business podcast exploring how founders and parents build meaningful companies without sacrificing their health, families, or values.
Through honest conversations with entrepreneurs, investors, parents, and next-generation leaders, the show dives into the real milestones that shape business, wellness, and life.
New episodes release Tuesdays and Fridays.
Episodes
39 episodes
The Soil is Broken - and It's Showing Up in Our Patients | Dr. Nanda | Part 4
This episode isn't about eating clean. It's about what's actually missing from the food chain before the food reaches you - and what it takes to try to fix it at the source.In Part 4 of this conversation, Dr. Nanda - physician,...
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Episode 35
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20:37
The Myth That Keeps Real Estate Investors Broke and the Tool They're Afraid to Use | Tanh | Part 4
This episode isn't about finding deals or picking markets. It's about the beliefs and blind spots that keep capable people from building anything durable - and the operational habits that separate investors who last from those who don't....
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Episode 34
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20:29
EMFs, Calcium Channels, And Kids | Dr.Nanda | Part 3
This episode isn't about avoiding technology. It's about understanding what it does - so you can decide with information instead of assumption.In Part 3 of this conversation, Dr. Nanda breaks down the biological mechanisms behi...
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Episode 33
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24:09
Why Networking, Patience, And Value-Add Beat Cookie-Cutter Strategies | Tanh | Part 3
This episode isn't about picking the right market or finding off-market deals. It's about the structural decisions most real estate operators make on autopilot - and why some of them quietly destroy long-term returns.In Part 3 ...
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25:35
How Wealthy Investors Reduce Taxes By Never Selling | Eshwar Prasad | Part 9
This episode isn't about closing out a series. It's about the philosophy underneath everything Eshwar shared across nine conversations - and it comes down to three words: give first, always.In Part 9, Eshwar closes with the mec...
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Episode 33
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24:37
Stop Refreshing Your Portfolio App | Eshwar Prasad | Part 8
This episode isn't about which assets to buy. It's about why most people lose money on good assets - and the single behavior that guarantees it.In Part 8 of this conversation, Eshwar - solo founder and long-horizon investor - b...
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Episode 32
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25:55
How Long-Term Investing Beats Hustle Culture | Eshwar Prasad | Part 7
This episode isn't about getting rich fast. It's about what wealth actually requires - and why patience is the constraint most people never solve for.In Part 7, Eshwar - solo founder and AI builder - answers the questions that ...
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Episode 31
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27:05
Build The Stanford Mindset | Eshwar Prasad | Part 6
This episode isn't about elite schools. It's about what they actually manufacture - and whether you can build the same output without the institution.In Part 6 of this conversation, Eshwar - solo founder building AI products - ...
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Episode 30
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26:12
How AI Lets Small Teams Build Trillion Dollar Ideas | Eshwar Prasad | Part 4
This episode isn't about AI hype. It's about what happens when the cost of building a breakthrough collapses - and who actually moves first.In Part 4 of this conversation, Eshwar - a solo founder building AI products - makes th...
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Episode 29
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25:12
The $200K Decision: What Money Does to Your Confidence as a Founder | Eshwar Prasad | Part 2
This episode isn't about strategy or systems. It's about what happens to the person running the strategy - after the first loss, after the money, after the marriage, after the milestone.In Part 2 of this conversation, Eshwar - ...
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Episode 28
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25:55
Why the W-2 Is Ending, How AI Agents Are Replacing Jobs, and What Operators Should Build Right Now | Eshwar Prasad | Part 3
This episode isn't about how to use AI tools. It's about what happens structurally - to work, money, and business models - when AI agents do most of the work.In Part 3 of this conversation, Eshwar - a solo founder building Exem...
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Episode 28
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25:33
CEO Removed Himself From His Own Business No Calendar, No Meetings, No Decisions | Eshwar Prasad | Part 5
This episode isn't about stepping back from your business.It's about the deliberate architecture of removing yourself as the decision bottleneck - and what that actually requires to function.In Part 5 of this conv...
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Episode 27
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25:49
From IT Staffing to AI Builder: One CEO's System for Finding Opportunities and Failing Fast | Eshwar Prasad | Part 1
This episode is about what a founder actually does when he decides the next opportunity requires starting over.In Part 1 of this conversation, Eshwar - CEO of a global IT staffing company - breaks down why he handed day-to-day ...
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Episode 26
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26:54
How to Underwrite, Select, and Lease Commercial Real Estate | Tanh | Part 2
This episode isn't about getting started in commercial real estate. It's about understanding the mechanics before you make a decision that residential experience didn't prepare you for.In Part 2 of this conversation, Tanh walks...
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Episode 25
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24:29
Maya Tesla, Age 6: On Fear, Decisions, and Doing Hard Things Anyway | Chief Milestones
Maya is six years old. She practices Bharatanatyam daily, set a goal to post four videos this year, and negotiates school attendance on her own terms.She also has a dance performance coming up on Saturday - a brand-new song - a...
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Episode 24
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15:55
The Retired Pharmacist Who Built a Commercial Real Estate Portfolio | Tanh | Part 1
This episode isn't about real estate. It's about what it actually takes to build a wealth system outside your primary career - and then execute it under real constraints.In Part 1 of this conversation, Tanh - a retired pharmaci...
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Episode 23
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28:36
Three Buckets: How to Think About ROI in STR Value-Add Design | Ishita Nagda Lalan | part 2
This episode isn't about design aesthetics. It's about capital allocation - and what it actually takes to turn a distressed property into a top-performing short-term rental.In Part 2 of this conversation, Ishita Nagda Lalan - a...
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Episode 22
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25:28
From Architecture School to STR Design Operator: How Visa Constraints, a Failed Fourplex, and a Work Permit Delay Built a Real Business | Ishita Nagda Lalan | Part 1
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Episode 22
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24:54
Vaccines, Adjuvants, and Informed Consent: What an Oncologist Found When He Read the Studies - and How It Changed His Decisions for His Own Kids | Dr. Nanda | Part 2
This episode isn't about vaccine politics.It's about what happens when a doctor trained in oncology applies the same research standards to childhood vaccines that he applies to cancer treatment - and what he found when he did.<...
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Episode 21
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22:34
Building a Hotel Portfolio Under Real Constraints: GP Partnerships, Flagged vs. Boutique, and What the First Acquisition Actually Feels Like | Sujay Mehta | Part 3
This episode isn't about hotel branding or market trends.It's about what it actually takes to build a commercial real estate portfolio when the financing is complicated, the partners are rare, and the preparation has to happen ...
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Episode 20
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27:31
When Medicine Runs Out of Answers: An Oncologist's Journey From Certainty to Root Cause | Dr. Nanda | Part 1
This episode isn't about autism.It's about what happens when the framework you've built your entire career on stops working - and what you do next.Dr. Nanda is a board-certified oncologist and hematologist who als...
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Episode 19
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24:12
When Creative Talent Stops Scaling the Business | Alex Morgan | Part 2
This episode isn’t about creativity. It’s about what happens when talent outgrows structure.In Part 2 of this conversation, Alex explains why creative ability alone couldn’t carry the business forward - and where syste...
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Episode 18
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25:44
What Breaks Creative Businesses When They Try to Scale | Alex Morgan | Part 1
This episode isn’t about creativity or branding. It’s about what it actually takes to run a creative business inside real operational constraints. In Part 1 of this conversation, Alex breaks down how client work, team growt...
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Episode 17
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26:41
When Growth Exposes the Systems You Avoided Building | Sujay Mehta | Part 2
This episode isn’t about leadership style. It’s about what actually breaks when growth outpaces systems.In Part 2 of this conversation, Sujay - founder and operator - walks through the constraints that emerged once the business...
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Episode 16
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24:33
Why Long-Term Operators Stop Chasing Quick Wins | Sujay Mehta | Part 1
This episode isn’t about passive income. It’s about the constraint most investors underestimate: time.In Part 1 of this conversation, Sujay - hotel investor and long-term operator - explains why he never built his strategy arou...
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Episode 15
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24:59