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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 - breaks down the actual mechanics of why markets move, why currency dilution is the engine behind every asset price increase, and why watching your portfolio app is the most expensive habit a retail investor can have.
He also gets specific about his own real estate LP investments - the capital calls, the negative returns, the dead money - and walks through the no-leverage comparison he ran between multifamily real estate and Bitcoin that changed how he allocates capital.
This isn't a bullish Bitcoin pitch. It's a constraint analysis. When you remove leverage from both sides of the comparison and account for property taxes, HOA, capital calls, and systemic fragility, the math changes. He did the math.
In this episode:
- Why Stock Prices Go Up - And What It Actually Has To Do With The Dollar
- How Three Percent Of Shareholders Set The Price For Everyone Else
- Why Real Estate Only Works Through Leverage And What That Risk Profile Actually Looks Like
- His Multifamily Lp Experience And What Passive Investing Really Costs
- The No-Leverage Apples-To-Apples Comparison Between Real Estate And Bitcoin
- 2008 Cascade Mechanics And Why Six Sigma Events Are Becoming More Frequent
- Why Bitcoin Is The Only Asset You Can Carry Across A Border In Your Head
- What Being An Aggressive Investor Actually Means At His Stage
Chief Milestones is a series for operators, founders, and decision-makers navigating real constraints - in business, capital, and the life built around both.
Reach out: [email protected]
Chief Milestones is a video podcast featuring honest conversations with founders, parents, and investors about building real businesses, staying healthy, and raising families.
New episodes release Tuesdays and Fridays.
Youtube: https://www.youtube.com/@ChiefMilestones
Instagram: https://www.instagram.com/chiefmilestones/
Spotify: https://open.spotify.com/show/7HLDAe7SP3GnJSTOgAQqLy?si=6e9ac82be46f413c
Apple Podcasts: https://podcasts.apple.com/us/podcast/chief-milestones/id1861185226
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By Reshma VadlamudiThis 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 - breaks down the actual mechanics of why markets move, why currency dilution is the engine behind every asset price increase, and why watching your portfolio app is the most expensive habit a retail investor can have.
He also gets specific about his own real estate LP investments - the capital calls, the negative returns, the dead money - and walks through the no-leverage comparison he ran between multifamily real estate and Bitcoin that changed how he allocates capital.
This isn't a bullish Bitcoin pitch. It's a constraint analysis. When you remove leverage from both sides of the comparison and account for property taxes, HOA, capital calls, and systemic fragility, the math changes. He did the math.
In this episode:
- Why Stock Prices Go Up - And What It Actually Has To Do With The Dollar
- How Three Percent Of Shareholders Set The Price For Everyone Else
- Why Real Estate Only Works Through Leverage And What That Risk Profile Actually Looks Like
- His Multifamily Lp Experience And What Passive Investing Really Costs
- The No-Leverage Apples-To-Apples Comparison Between Real Estate And Bitcoin
- 2008 Cascade Mechanics And Why Six Sigma Events Are Becoming More Frequent
- Why Bitcoin Is The Only Asset You Can Carry Across A Border In Your Head
- What Being An Aggressive Investor Actually Means At His Stage
Chief Milestones is a series for operators, founders, and decision-makers navigating real constraints - in business, capital, and the life built around both.
Reach out: [email protected]
Chief Milestones is a video podcast featuring honest conversations with founders, parents, and investors about building real businesses, staying healthy, and raising families.
New episodes release Tuesdays and Fridays.
Youtube: https://www.youtube.com/@ChiefMilestones
Instagram: https://www.instagram.com/chiefmilestones/
Spotify: https://open.spotify.com/show/7HLDAe7SP3GnJSTOgAQqLy?si=6e9ac82be46f413c
Apple Podcasts: https://podcasts.apple.com/us/podcast/chief-milestones/id1861185226