The Investing for Beginners Podcast - Your Path to Financial Freedom
By Andrew Sather, Stephen Morris, and Evan Raidt | Stock Market Guide to Buying Stocks

Nieuwste aflevering
742 afleveringen
- The temptation of hitting a 100x return in the stock market often drives investors straight into emotional traps, leading to reckless greed or paralyzing fear. In this episode, Stephen and Andrew dive into the psychology of money, breaking down the true economics behind massive winners, how to manage emotional swings, and why building a disciplined, repeatable process is the only way to safeguard your portfolio over the long term.
What You Will Learn
Why the 100-bagger dream is a trap: How chasing huge wins distorts your decision-making and leads to panic selling or holding onto garbage.
The hidden 3-part math behind 100x stocks: Why massive revenue growth isn't enough without valuation multiple expansion and widening profit margins.
How to eliminate emotional trading: Simple guardrails—like forced 24-hour waiting periods and monthly decision schedules—to stop self-sabotage.
Overcoming the Dunning-Kruger effect: Recognizing beginner’s arrogance before the market humbles your portfolio.
The After-Action Review (AAR) framework: How military-style post-mortems and AI tools can refine your investment thesis and keep you grounded.
Timestamps
00:00 The psychological traps of chasing and managing 100-bagger stocks
02:30 The reality of "100-baggers" and avoiding social media hype
05:00 The three engines of a 100x stock: Valuation, Growth, and Margin Expansion
09:30 Managing big wins: Panic selling vs. systematic profit-taking
14:00 Building psychological buffers (24-hour rules & monthly execution cycles)
21:00 The danger of arrogance: The Dunning-Kruger effect in investing
25:30 Implementing an After-Action Review (AAR) and re-reading old research
31:00 Overcoming a lack of confidence and taking the first step
Resources Mentioned
The Value Spotlight Newsletter: https://einvestingforbeginners.com/value-spotlight-newsletter/
Have questions or want your story featured? Email the show at newsletter@einvestingforbeginners.com or comment below. Your feedback shapes the podcast!
Remember, invest with a margin of safety—emphasis on the safety. Have a great week, and we’ll talk to you next time.
Timestamps are generated by artificial intelligence, and are not 100% accurate depending on the platform used for listening.
Today’s show is sponsored by:
Download the Plynk app today to start building your investing confidence. https://plynkinvest.app.link/IFBpodcast
Download Cash App Today: https://click.cash.app/ui6m/0th4z72y #CashAppPod As a Cash App partner, I may earn a commission when you sign up for a Cash App account. Cash App is a financial services platform, not a bank. Banking services provided by Cash App’s bank partner(s). Bitcoin services provided by Block, Inc. For additional information, see the Bitcoin disclosures.
Shopify: Stop waiting for permission to build something. Your next revenue stream starts for free at shopify.com/beginners
Turn your passion into profit, connect directly with eager buyers, and grow your business by hosting live, interactive auctions at https://whatnot.com/sell
Supercharge your productivity and automate your daily tasks by building custom AI agents in your all-in-one workspace at https://notion.com/investing
The Perfect Jean makes insanely comfortable, great-fitting jeans you can wear all day—check them out at theperfectjean.nyc.
Function Health helps you get ahead of your health with comprehensive lab testing and clear, actionable insights—learn more at functionhealth.com.
Interested in how your company sponsor the show? Reach us at equity@einvestingforbeginners.com
SUBSCRIBE TO THE SHOW Apple | Spotify | YouTube | Amazon | Tunein
Learn more about your ad choices. Visit megaphone.fm/adchoices - This episode is a follow-up to the recent “Money Debates” episode. Evan and Andrew run the format back with new topics: they present both sides of common financial arguments, then share what they personally agree with—sometimes changing their minds mid-discussion.
They debate whether a HELOC (home equity line of credit) can replace a traditional emergency fund, whether paying off a mortgage early is smart or mostly emotional, whether a windfall should be invested as a lump sum or dollar-cost averaged over time, and whether credit card debt should be attacked directly or transferred to lower-interest options first. The recurring theme: math matters, but behavior and personality matter too—the “best” move depends on what you’ll actually follow through on.
What You Will Learn
HELOCs aren’t a replacement for an emergency fund for small emergencies, but can be a realistic tool for large home costs when cash savings aren’t feasible.
HELOC risks: variable rates, fees, and the danger of over-leveraging your home equity. Use a margin of safety.
Mortgage payoff is partly math, partly psychology: paying extra can be a guaranteed return and peace of mind, but investing elsewhere may win mathematically.
Lump sum vs DCA: lump sum usually wins statistically for broad-market investing, but DCA can reduce emotional whiplash—especially for very large amounts or stock picking.
Credit card debt: transferring balances can save real money if you still pay aggressively and don’t re-run the balance back up. For some people, “simpler” beats “optimal.”
Timestamps
0:00 Money Debates Part 2 — format + what’s on the table
1:10 Topic 1: Emergency fund vs HELOC for home emergencies (definitions + framing)
3:00 HELOC downsides: variable rates, fees, and risking your home equity
5:10 When a HELOC can make sense (big-ticket repairs like roofs)
7:10 HELOC vs pulling from retirement: which is the lesser evil?
9:00 The “renovation raises home value” argument—and why it can backfire
11:40 Topic 2: Pay off your mortgage early vs invest instead
13:10 The lender calculator trap: “savings” vs opportunity cost
15:10 Accessibility: home equity vs taxable investing
16:40 Pro-payoff case: peace of mind, lower expenses, guaranteed return
19:20 The real answer: personality + interest rate (Evan shares his stance)
21:20 Topic 3: Lump sum vs dollar-cost averaging (DCA) after a windfall
22:40 Lump sum argument: time in the market > timing the market
24:10 DCA argument: reduce regret + average cost basis over time
26:10 Where they land: amount matters (10k vs 1–2M) + stock picking vs index
28:40 Topic 4: Pay off credit card debt vs transfer it (0% cards / personal loans)
30:10 Transfer argument: save hundreds/thousands in interest if you still pay it down
32:10 Behavior argument: transfers can “feel like progress” and reduce urgency
34:10 The practical middle ground: transfer if disciplined; otherwise automate payoff
Resources Mentioned
The Value Spotlight Newsletter: https://einvestingforbeginners.com/value-spotlight-newsletter/
Free monthly budgeting spreadsheet: https://einvestingforbeginners.com/budget/
Email Evan: evan@einvestingforbeginners.com
Have questions or want your story featured? Email the show at newsletter@einvestingforbeginners.com or comment below. Your feedback shapes the podcast!
Remember, financial freedom is built one smart move at a time. Keep it simple, keep it steady, and at any rate, we’ll see you next time.
Timestamps are generated by artificial intelligence, and are not 100% accurate depending on the platform used for listening.
Today’s show is sponsored by:
Download the Plynk app today to start building your investing confidence. https://plynkinvest.app.link/IFBpodcast
Download Cash App Today: https://click.cash.app/ui6m/0th4z72y #CashAppPod As a Cash App partner, I may earn a commission when you sign up for a Cash App account. Cash App is a financial services platform, not a bank. Banking services provided by Cash App’s bank partner(s). Bitcoin services provided by Block, Inc. For additional information, see the Bitcoin disclosures.
Shopify: Stop waiting for permission to build something. Your next revenue stream starts for free at shopify.com/beginners
Upgrade your wardrobe with Quince to get high-quality, luxury essentials at a fraction of the cost by visiting https://quince.com/beginners
Turn your passion into profit, connect directly with eager buyers, and grow your business by hosting live, interactive auctions at https://whatnot.com/sell
Supercharge your productivity and automate your daily tasks by building custom AI agents in your all-in-one workspace at https://notion.com/investing
Interested in how your company sponsor the show? Reach us at equity@einvestingforbeginners.com
SUBSCRIBE TO THE SHOW Apple | Spotify | YouTube | Amazon | Tunein
Learn more about your ad choices. Visit megaphone.fm/adchoices - In this episode, Andrew interviews Sean Tepper, founder and CEO of Tykr (T-Y-K-R), an investing education and stock analysis platform built for everyday investors who want a clear, repeatable process. Sean shares how he went from running a service business to building a value-investing system inspired by Phil Town—then turning it into software with a simple “stoplight” rating: green (on sale), gray (watch), red (overpriced).
They break down what drives Tykr’s ratings, why Sean avoids technical analysis, and how Tykr uses a combination of financial statement trends and margin of safety to score stocks. You’ll also hear his framework for evaluating companies beyond the numbers (the 4Ms: Math, Meaning, Moat, Management), why controlling emotions is the hardest part of investing, and how to think about building a focused portfolio without over-diversifying.
What You Will Learn
How Tykr’s green/gray/red stoplight system works
The two big inputs behind the rating: financial statement trend score
Why Sean ignores technical analysis
The 4M framework for evaluating a stock beyond the numbers
How “stockpiling” helps investors fight panic and use downturns as buying opportunities
Timestamps
00:00 Meet Sean Tepper (Tykr founder)
00:34 Sean’s origin story: service business → investing → building a scalable system
02:18 Why he ditched influencers/noise and went math-first
03:16 The stoplight system: green/gray/red
05:31 Fundamentals vs technicals
06:53 Why value investing wins long-term
10:03 What makes a stock “green”
15:25 Who Tykr is for and why brokers leave beginners stuck at “now what?”
17:37 Biggest investor mistake: emotions vs. “stockpiling” during downturns
22:07 AI and the 4Ms framework
Resources Mentioned
The Value Spotlight Newsletter: https://einvestingforbeginners.com/value-spotlight-newsletter/
Have questions or want your story featured? Email the show at newsletter@einvestingforbeginners.com or comment below. Your feedback shapes the podcast!
Remember, invest with a margin of safety—emphasis on the safety. Have a great week, and we’ll talk to you next time.
Timestamps are generated by artificial intelligence, and are not 100% accurate depending on the platform used for listening.
Today’s show is sponsored by:
Download the Plynk app today to start building your investing confidence. https://plynkinvest.app.link/IFBpodcast
Download Cash App Today: https://click.cash.app/ui6m/0th4z72y #CashAppPod As a Cash App partner, I may earn a commission when you sign up for a Cash App account. Cash App is a financial services platform, not a bank. Banking services provided by Cash App’s bank partner(s). Bitcoin services provided by Block, Inc. For additional information, see the Bitcoin disclosures.
Shopify: Stop waiting for permission to build something. Your next revenue stream starts for free at shopify.com/beginners
Turn your passion into profit, connect directly with eager buyers, and grow your business by hosting live, interactive auctions at https://whatnot.com/sell
Supercharge your productivity and automate your daily tasks by building custom AI agents in your all-in-one workspace at https://notion.com/investing
The Perfect Jean makes insanely comfortable, great-fitting jeans you can wear all day—check them out at theperfectjean.nyc.
Function Health helps you get ahead of your health with comprehensive lab testing and clear, actionable insights—learn more at functionhealth.com.
Interested in how your company sponsor the show? Reach us at equity@einvestingforbeginners.com
SUBSCRIBE TO THE SHOW Apple | Spotify | YouTube | Amazon | Tunein
Learn more about your ad choices. Visit megaphone.fm/adchoices - Stock screeners can feel intimidating, but they’re really just a fast way to generate starting points—not “buy” signals. In this episode, Stephen and Andrew build a simple screener in Fiscal.ai (growth, ROIC, balance sheet strength, valuation, and anti-dilution rules), then run it live and walk through what shows up.
You’ll hear how they quickly pressure-test businesses like Yelp, LendingTree, Brinker (Chili’s), Yeti, Zoetis, and CarGurus—using basic questions around moats, management quality, cyclicality, and what the financials are actually saying. The big takeaway: keep an open mind, be willing to be wrong, and use the screener to spark curiosity—then do the real research.
What You Will Learn
How to build a “good enough” stock screener without overcomplicating it
Why a screener is a starting point, not an investing answer
The key metrics Andrew screens for (growth, ROIC, leverage, valuation, dilution signals)
How to do a fast first-pass business check
How to think about “cheap” stocks correctly
Timestamps
00:00 What this “live screener” episode is (no prep, show the process)
00:49 How Andrew built the screener and what it’s screening for
00:56 Fiscal.ai and the screener rules (growth, SBC <10%, negative financing cash flow, valuation, leverage, ROIC)
02:36 Run the screener: 43 names + how they’ll pick what to review
02:45 Yelp (YELP): quick overview + “Yelp Assistant” + 90% gross margins
03:46 Yelp moat question: “are people still using Yelp?” + Google/Maps competition
08:18 LendingTree (TREE): not a lender—lead gen marketplace + why research matters
11:20 LendingTree: what happened post-2019 (legal disputes, losses, data breach)
18:06 Brinker (EAT): Chili’s surprise growth + “cheap” means valuation, not share price
22:23 Brinker: same-store sales as the key KPI + why 25% comps is shocking
Resources Mentioned
The Value Spotlight Newsletter: https://einvestingforbeginners.com/value-spotlight-newsletter/
Have questions or want your story featured? Email the show at newsletter@einvestingforbeginners.com or comment below. Your feedback shapes the podcast!
Remember, invest with a margin of safety—emphasis on the safety. Have a great week, and we’ll talk to you next time.
Timestamps are generated by artificial intelligence, and are not 100% accurate depending on the platform used for listening.
Today’s show is sponsored by:
Download the Plynk app today to start building your investing confidence. https://plynkinvest.app.link/IFBpodcast
Download Cash App Today: https://click.cash.app/ui6m/0th4z72y #CashAppPod As a Cash App partner, I may earn a commission when you sign up for a Cash App account. Cash App is a financial services platform, not a bank. Banking services provided by Cash App’s bank partner(s). Bitcoin services provided by Block, Inc. For additional information, see the Bitcoin disclosures.
Shopify: Stop waiting for permission to build something. Your next revenue stream starts for free at shopify.com/beginners
Turn your passion into profit, connect directly with eager buyers, and grow your business by hosting live, interactive auctions at https://whatnot.com/sell
Supercharge your productivity and automate your daily tasks by building custom AI agents in your all-in-one workspace at https://notion.com/investing
The Perfect Jean makes insanely comfortable, great-fitting jeans you can wear all day—check them out at theperfectjean.nyc.
Function Health helps you get ahead of your health with comprehensive lab testing and clear, actionable insights—learn more at functionhealth.com.
Interested in how your company sponsor the show? Reach us at equity@einvestingforbeginners.com
SUBSCRIBE TO THE SHOW Apple | Spotify | YouTube | Amazon | Tunein
Learn more about your ad choices. Visit megaphone.fm/adchoices - In this episode, Evan and Andrew try a fun (and slightly dangerous) format: they each bring real financial decisions from their past, give context, then let the other person interrogate the decision and assign a letter grade. The point isn’t to shame anyone—it’s to show how context changes the “right” answer in personal finance.
They cover Evan’s Tesla purchase, Andrew’s past truck purchase, Evan’s “coffee gear” hobby spending, Andrew’s use of credit cards to float business expenses during a revenue decline, emergency fund sizing, and a final quick win: Andrew buying a MacBook Air on a Prime Day deal.
What You Will Learn
A “bad” decision can become reasonable once you add context
For car buying, the payment-to-income ratio matters more than the raw monthly payment.
Spending on hobbies isn’t automatically irresponsible if you’re avoiding high-interest debt and still funding the important stuff
Business credit cards can become a slow trap when revenue declines gradually
Emergency funds are personal
Timestamps
0:00 The “be judgy” grading format explained (A–F)
2:15 Evan’s decision #1: buying a new Tesla Model 3 (2023) — context + numbers
3:45 Breaking down the real cost
5:05 Interest rate, loan term, and paying it down early with bonuses
6:25 Was it emotional or a good value?
9:25 Why some cars hold value better than others
10:50 Maintenance reality check
12:05 The big test
14:45 Verdict
16:55 Andrew’s decision #1: buying a used truck (2015/2016) after moving
18:30 Payment-to-income
21:10 The emotional driver
24:10 Final grade for the truck decision
26:10 Evan’s decision #2: $3,500 in coffee gear + $50–$60/month beans
28:00 Maintenance + upgrade path + the “no debt” rule
29:55 Verdict
31:20 Andrew’s decision #2: using credit cards to cover business expenses during decline
33:10 The slippery slope
35:10 Why gradual revenue drops delay hard decisions
37:00 Cutting costs in order: software → payroll/income → even retirement funds
39:10 The emotional weight of a business and why “just get another job” isn’t that simple
41:00 Grade
43:40 Evan’s decision #3: shrinking emergency fund from ~10 months to ~5.5–6 months
46:00 Why “too much cash” can feel wasteful
47:10 Verdict: enough is enough
48:50 Andrew’s final decision: Prime Day MacBook Air purchase (deal logic + reality check)
Resources Mentioned
The Value Spotlight Newsletter: https://einvestingforbeginners.com/value-spotlight-newsletter/
Free monthly budgeting spreadsheet: https://einvestingforbeginners.com/budget/
Email Evan: evan@einvestingforbeginners.com
Have questions or want your story featured? Email the show at newsletter@einvestingforbeginners.com or comment below. Your feedback shapes the podcast!
Remember, financial freedom is built one smart move at a time. Keep it simple, keep it steady, and at any rate, we’ll see you next time.
Timestamps are generated by artificial intelligence, and are not 100% accurate depending on the platform used for listening.
Today’s show is sponsored by:
Download the Plynk app today to start building your investing confidence. https://plynkinvest.app.link/IFBpodcast
Download Cash App Today: https://click.cash.app/ui6m/0th4z72y #CashAppPod As a Cash App partner, I may earn a commission when you sign up for a Cash App account. Cash App is a financial services platform, not a bank. Banking services provided by Cash App’s bank partner(s). Bitcoin services provided by Block, Inc. For additional information, see the Bitcoin disclosures.
Shopify: Stop waiting for permission to build something. Your next revenue stream starts for free at shopify.com/beginners
Upgrade your wardrobe with Quince to get high-quality, luxury essentials at a fraction of the cost by visiting https://quince.com/beginners
Turn your passion into profit, connect directly with eager buyers, and grow your business by hosting live, interactive auctions at https://whatnot.com/sell
Supercharge your productivity and automate your daily tasks by building custom AI agents in your all-in-one workspace at https://notion.com/investing
Interested in how your company sponsor the show? Reach us at equity@einvestingforbeginners.com
SUBSCRIBE TO THE SHOW Apple | Spotify | YouTube | Amazon | Tunein
Learn more about your ad choices. Visit megaphone.fm/adchoices
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