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TIP773: How Systems and Simple Math Shape Better Investing w/ Kyle Grieve

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TIP773: How Systems and Simple Math Shape Better Investing w/ Kyle Grieve

We Study Billionaires - The Investor’s Podcast Network

2025/11/30
We Study Billionaires - The Investor’s Podcast Network

We Study Billionaires - The Investor’s Podcast Network

2025/11/30
OverviewShownoteHighlightsTranscriptChaptersPins

Shownote

On today’s episode, Kyle Grieve discusses powerful mental models from systems thinking and mathematics and applies them directly to investing and life. He breaks down concepts like feedback loops, kill criteria, scale, compounding, randomness, and regressi...

Highlights

In this episode, Kyle Grieve dives into the power of mental models drawn from systems thinking and mathematics to enhance decision-making in investing and life. He explores how timeless principles can clarify complex realities, improve judgment under uncertainty, and help investors build resilient portfolios through disciplined frameworks rather than reactive choices.
08:45
Deteriorating customer credit quality poses a significant risk to Sezzle's success
10:20
Kill criteria help close long feedback loops in investing by setting objective conditions for exiting a position
14:13
Positions with narrower cones of uncertainty should receive larger capital allocations.
17:34
A business can crumble under the weight of scale if not managed properly.
27:47
Community-adjusted EBITDA is a farcical metric that ignored actual profitability
32:58
A 27% cash flow compounding rate can increase value 11x over 10 years
38:22
A $5,000 credit card balance at 20% annual interest has a hidden catch most are unaware of.
40:05
One can be wrong 50% of the time and still make great returns
43:16
A small number of positions account for most portfolio returns
59:18
Extreme performance regresses to the mean; base rates matter more than outliers

Chapters

Intro
00:00
How feedback loops stabilize or reinforce outcomes in investing
03:23
How kill criteria help you make predetermined decisions in a noisy world
10:11
Why the cone of uncertainty is useful for evaluating conviction and position sizing
14:09
How scale changes the behavior, costs, and risks of a growing business
17:33
How algorithms clarify which inputs drive the conclusions you rely on
25:06
How to evaluate a company’s ability to reach critical mass and become self-sustaining
30:20
The hidden forms of compounding that are just as powerful as the visible ones
35:35
Why power laws should influence your portfolio concentration
40:02
How randomness shapes investing outcomes, and how to take advantage of it
43:12
Why regression to the mean matters during periods of strong or weak performance
51:24

Transcript

Speaker 2: You're listening to TIP. Kyle Grieve: Did you know that over long periods, just a handful of stocks will account for the vast majority of a portfolio's return? And that's even if half of your investments fail. The winners can still make up for ...