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Artwork for Skippy and Doogles Talk Investing

Skippy and Doogles Talk Investing

Skippy and Doogles
Openai
Spacex
Artificial Intelligence
Private Credit
Private Equity
Deckers Outdoor Corporation
Deckers Outdoor
Ugg
Teva
Warren Buffett
Polymarket
Oracle
Tax Policy
Gamestop
Pinterest
Japan
Novo Nordisk
Time Warner Discovery
Youth Sports
Anthropic

For years, two of the world's greatest investing minds, Skippy and Doogles, have debated their investing philosophies. They started recording their phone calls to bring that stock market wisdom to the masses. Buckle up, because you never know where these conversations might go, and what kind of priceless investment knowledge will soon hit your mentals.

PublishesWeeklyEpisodes283Founded5 years ago
Number of ListenersCategories
EntrepreneurshipInvestingBusiness

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Artwork for Skippy and Doogles Talk Investing

Latest Episodes

Seed valuations have officially gone off the rails. Skippy and Doogles break down why brand-new startups are raising massive rounds at eye-popping prices. Then, they head to Costco, where a longtime cashier has become a millionaire the old-fashioned ... more

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Doogles covers Polymarket’s alleged influencer ad mess, including fake bets and fake wins. Then they crack open SoftBank’s shareholder deck, featuring golden eggs, goose value, and possibly the most bizarre visual explanation of alpha ever presented ... more

YouTube

This is a quick-hit episode that connects World Cup Taco Bell tourism, inheritance drama, remote work rage, Syracuse’s enrollment problem, Dave Ramsey’s questionable credit card math, and why everyone feels broke while the stock market keeps minting ... more

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We break down the math behind a $400K college decision, comparing Ivy League prestige, flagship state schools, trade school, and the emotional pull of “dream school” thinking. Along the way, we hit SpaceX IPO mania, wild price-to-sales ratios, US soc... more

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Key Facts

Contact Information
Podcast Host
Number of Listeners
Find out how many people listen to this podcast per episode and each month.

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Recent Guests

Jessica Riedel
Expert on tax policy, described as Republican conservative
Tax policy expert (Republican-leaning)
Episode: What's a Little Tax Lie Between Friends?
Jeff Horning
Founding partner at Inside Partners
Inside Partners
Episode: Is Software Dead or Just On Sale?
Lee Roach
Author of The Value Road Substack; investing writer
The Value Road
Episode: Finding Value Where No One Is Looking w/Lee Roach (author of The Value Road Substack)
Jim Simons
Prominent investor discussed via clip
Renaissance Technologies (referenced in story)
Episode: How the NFL Prints Money, and Why College Tuition Just Crashed
Seth Klarman
Investor, founder of Baupost Group; discussed in an interview segment
Baupost Group
Episode: Michael Mauboussin, PE Ratios & The Art of Future Value

Hosts

Skippy
Host of the show; primary speaker and strategist; co-presenter with investing banter and analysis
Doogles
Co-host; investing discussant; engages in debates and analysis with Skippy

Reviews

5.0 out of 5 stars from 55 ratings
  • Great advice, great speakers

    Worth listening for smart investment advice.

    Apple Podcasts
    5
    sidbyn
    Canada4 years ago
  • Laugh & Learn

    I’ve just recently become a listener of this weekly pod and guarantee you’ll laugh while learning about the world of investing. These two are fun and Cracker Jack smart with some varying strategies that don’t always align with one another. They obviously share a deep and respectful friendship. You may even learn a tip or two on how to honestly communicate from differing vantage points and life experiences. Look for gold nuggets as you listen.

    Apple Podcasts
    5
    Malarke
    United States4 years ago
  • They read and are smarter than your friends

    Well worth the listen for these reasons: 1. They read all the things you don’t have time for and provide succinct cliff notes with critical analysis. B) Skippy and Doogles let you in to the conversation you wish you could have with your own friends, but unfortunately your own friends are just not that intelligent. 3. Relevant topics, entertaining, and very easy to listen to. Keep it up gentlemen, great show.

    Apple Podcasts
    5
    DonaldKent
    Canada5 years ago
  • Ton of fun

    These podcasts are a great mix of all things investing; history of, political influence on, economics, real-world experience, data & insights from the industry. And oh yea, banter.

    Apple Podcasts
    5
    J Tarr
    United States5 years ago
  • Great Insight

    Very intelligent yet digestible content for the common stock market enthusiast. I always appreciate the simple breakdowns of more complex ideas and scenarios. Can’t wait for more great content! Good work!

    Apple Podcasts
    5
    #1 Reimtime
    United States5 years ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Clear, entertaining takes on investing with smart banter.
Charming mix of humor and rigorous analysis that keeps listeners coming back.
Accessible yet deep; they make complex topics feel approachable.
Great chemistry; discussions feel authentic and high-signal for investors.

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Prof G Markets
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NerdWallet's Smart Money Podcast
NerdWallet's Smart Money PodcastNerdWallet Personal Finance

Talking Points

Recent interactions between the hosts and their guests.

Finding Value Where No One Is Looking w/Lee Roach (author of The Value Road Substack)
Q: What sparked your interest in deep value, and how did you start translating your ideas into writings for others?
Lee discusses moving from first bad investments into a value-oriented framework, influenced by mentors and peers, leading to regular writing and feedback from readers that sharpened his tactics.
Finding Value Where No One Is Looking w/Lee Roach (author of The Value Road Substack)
Q: Can you tell us a little bit about your journey to becoming an investing writer and quitting your job to focus on The Value Road?
Lee explains he left his factory job after building enough consistent income from his writing and subscriptions, then describes learning from dense economics and investing books and moving from Seeking Alpha to deeper value investing.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

Listeners per Episode
Gender Skew
Location
Interests
Professions
Age Range
Household Income
Social Media Reach

Frequently Asked Questions About Skippy and Doogles Talk Investing

What is Skippy and Doogles Talk Investing about and what kind of topics does it cover?

Two seasoned investing minds trade sharp, entertaining analysis on value, growth, and market psychology, mixing data-driven critique with playful banter. Episodes cover high-level valuations, IPO dynamics, private markets, AI disruption, and long-horizon strategy, often contrasting conviction with discipline. Guests are rare, but the hosts' chemistry and approachable, hypothesis-driven debate make complex topics feel actionable for retail and professional investors alike. Noteworthy is a consistent emphasis on staying skeptical of hype, balancing quantitative rigor with real-world anecdotes, and weaving pop culture into Investment conversations. Potential listeners who enjoy rigorous yet informal stock discussions, contrarian takes, and pra... more

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Which podcasts are similar to Skippy and Doogles Talk Investing?

These podcasts share a similar audience with Skippy and Doogles Talk Investing:

1. Pod Save America
2. Prof G Markets
3. Odd Lots
4. The Daily
5. Motley Fool Hidden Gems Investing

How many episodes of Skippy and Doogles Talk Investing are there?

Skippy and Doogles Talk Investing launched 5 years ago and published 283 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on Skippy and Doogles Talk Investing?

Recent guests on Skippy and Doogles Talk Investing include:

1. Jessica Riedel
2. Jeff Horning
3. Lee Roach
4. Jim Simons
5. Seth Klarman

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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