In this monumental episode of Investing Unscripted, Jason and Jeff announce that they are bringing the podcast to an end—just one episode shy of their 200th milestone. This short reflection episode looks back on past guests, topics, and what had the biggest impact.

01:00 Why the Show Is Ending

02:28 Retrospective and Keeping It Light

03:28 Favorite Guests and Surprise Connections

05:40 Jim Gillies and Early Episodes

06:37 First Friday Livestream Memories

08:06 Podcast Community and Crossovers

09:25 Behind the Scenes Editing and Filler Words

10:21 How Podcasting Shaped Investing Views

11:14 Podcast Shapes Investing

13:40 Investor Identity Distilled

16:31 Talking Through Ideas

18:02 Favorite Episode Formats

20:46 Running Toward Fires

26:54 Wrap Up And Thanks

Companies mentioned: BAM, BN, CRWD, MSFT, S

Find where to listen & subscribe, portfolio contests, and contact information at https://investingunscripted.com

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Listen to the Chit Chat Stocks Podcast for discussions on stocks, financial markets, super investors, and more. Follow the show on Spotify, Apple Podcasts, or YouTube

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In this month's mailbag, Jason and Jeff tackle a wide array of listener questions, ranging from the tax efficiency of holding dividend stocks in taxable accounts to the potential risks of the NASDAQ fast-tracking private giants like SpaceX into its indexes. They also weigh in on newlyweds combining finances and choosing between brokerages like Schwab and Fidelity. Finally, the duo breaks down Walker & Dunlop's recent post-earnings stock drop and debates where to safely park your cash after hitting a major savings goal.

03:14 Taxable Dividend Strategy

11:54 Nasdaq Index Rule Changes

20:27 Dividend Bucket Rethink

25:57 Dividend Growth Compounding

26:38 Mastercard Low-Yield Lesson

27:42 Instagram Mailbag Setup

28:50 Consolidating Brokerage Accounts

31:47 Schwab Versus Fidelity

34:22 Combining Finances After Marriage

35:45 Money Talks and Guardrails

40:12 Walker and Dunlop Earnings

42:43 Investing After Saving Goal

45:43 Risk Spectrum and Time Horizon

Companies mentioned: AAPL, BOC, CRM, MA, META, MTH, QQQ, SCHW, WD

Find where to listen & subscribe, portfolio contests, and contact information at https://investingunscripted.com

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To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted

Listen to the Chit Chat Stocks Podcast for discussions on stocks, financial markets, super investors, and more. Follow the show on Spotify, Apple Podcasts, or YouTube

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Jason and Jeff tackle the current wave of market chaos—from oil price spikes and tariffs to the "AI is killing software" narrative. They dive into how they're personally navigating the noise, sharing recent portfolio additions such as Phinia (PHIN) and Clearway Energy that appear insulated from the macroeconomic volatility. They also unpack the AI software scare with deep dives into Toast, ServiceNow, and Procore, and Jason issues a warning about the hidden risks lurking in the booming private credit market.

01:19 AI Tariffs Oil Backdrop

03:38 Housekeeping Mailbag Plug

04:42 Staying the Course

07:18 Markets Recover Before Clarity

12:04 Stock Pick PHIN

19:01 Renewables Reality Check

20:54 Clearway Energy Buy

24:50 Energy Security and Oil Flows

26:36 Oil And Geopolitics

27:29 Krugman On Price Spikes

30:33 Toast Stock Breakdown

35:44 ServiceNow AI Strategy

37:35 Procore Construction Software

42:17 Private Credit Risks

47:38 Staying Invested In Chaos

49:19 Process Over Headlines

Companies mentioned: BAM, BEP, BX, CPNG, CWEN, DASH, ENPH, FOUR, KKR, NOW, ORCL, OWL, PCOR, PHIN, PYPL, SHOP, SQ, TOST

Find where to listen & subscribe, portfolio contests, and contact information at https://investingunscripted.com

*****************************************

To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted

Listen to the Chit Chat Stocks Podcast for discussions on stocks, financial markets, super investors, and more. Follow the show on Spotify, Apple Podcasts, or YouTube

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Subscribe to our portfolio on Savvy Trader

In this slightly belated "First Fridays" live stream, we dive into the current "vibes" of the stock market, check in on the 2026 Portfolio Contest, debate the long-term viability of MercadoLibre's lending business, and talk about Greg Abel’s first annual letter to Berkshire Hathaway shareholders.

01:53 Index Funds Running Joke

04:08 Market Vibes Check

06:28 K Shaped Economy Talk

12:09 Portfolio Contest Update

23:46 QuantumScape Buy Explained

27:59 Donut Labs Battery Debate

30:57 Battery Value Metrics

31:34 Kids Pick Stocks

32:58 Market Moves This Week

36:56 MercadoLibre Discount Debate

44:42 Options Premiums Q&A

47:13 Using Claude for Research

50:27 Greg Abel Letter Take

55:30 Berkshire After Buffett

Companies mentioned: AAPL, AMZN, AXP, BRK.B, ENR, KNSL, KO, MCO, MELI, QS, RKLB, TM

Find where to listen & subscribe, portfolio contests, and contact information at https://investingunscripted.com

*****************************************

To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted

Listen to the Chit Chat Stocks Podcast for discussions on stocks, financial markets, super investors, and more. Follow the show on Spotify, Apple Podcasts, or YouTube

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Ryan Henderson and Brett Schafer from the Chit Chat Stocks podcast join us for a special unscripted episode to track their evolution from college-aged podcasters running a family-and-friends fund to seasoned individual investors. We discuss learning the harsh realities of valuation during the 2022 bear market, the dangers of "analysis paralysis," and whether mastering your own psychology is more important than understanding financial mechanics. We also debate the merits of starter positions, explore Ryan's strict "three-year holding rule," and reveal the current watchlist stocks they are waiting to buy—along with the ones they kick themselves for missing.

02:09 Meet Chit Chat Stocks

04:30 Origin Story

08:56 Early Podcast Lessons

10:26 Valuation Reality Check

12:29 Mistakes Shape Process

14:09 Bear Market Incentives

18:19 Investing In Public

21:30 Overthinking Valuation

24:07 Match Vs Spotify

28:18 Costco One Share Rule

29:18 Owning Through Drawdowns

29:58 Fund Pressure vs Flexibility

32:26 Starter Positions Debate

34:07 Psychology Beats Fundamentals

38:03 Know Your Investing Style

39:57 When Stocks Go Nowhere

44:15 Rules to Avoid Selling

47:35 Build a Personal Framework

51:52 Watchlist Valuation Picks

55:40 Where to Find Their Work

59:14 Final Wrap and Signoff

Companies mentioned: ADYEY, AMZN, AXP, CAVA, COST, CPNG, CSU, HIMS, IBKR, MELI, MNDY, MRNA, MTCH, PYPL, RKLB, ROKU, SPOT, TSLA

Find where to listen & subscribe, portfolio contests, and contact information at https://investingunscripted.com

*****************************************

To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted

Listen to the Chit Chat Stocks Podcast for discussions on stocks, financial markets, super investors, and more. Follow the show on Spotify, Apple Podcasts, or YouTube

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Subscribe to our portfolio on Savvy Trader

Jason and Jeff go completely off-script to discuss what they are actually doing in their portfolios right now. Jeff breaks down why he bought more Datadog on a recent dip and his strategy for adding to Enphase, while Jason explains how he is using options (specifically selling puts) to generate income while waiting for better valuations. Plus, they analyze the risk vs. reward of QuantumScape, debate the new CEO at PayPal, and play a game of "buy or get off the pot" that ends with a live stock purchase.

00:53 Unscripted Earnings Season

04:34 Jeff Did a Thing

06:43 Why Buy Datadog Now

09:14 AI Risks for SaaS

11:34 Selling Puts Strategy

17:06 Market Psychology Chegg

19:41 Market Efficiency Long Term

23:15 Enphase DCA Dilemma

25:46 How to Time Adds

28:08 Quarterly Info Is Noise

28:30 Enphase Through the Cycle

29:49 QuantumScape Solid State Promise

31:50 Timing the Entry Price

33:53 Asymmetric Upside vs Risk

36:24 PayPal CEO Shakeup

38:59 Reframing the PayPal Thesis

44:48 Small Positions to Fix

46:36 Airbnb Growth Proof Points

Companies mentioned: ABNB, ADBE, CHGG, DDOG, ENPH, PYPL, QS, UPST

Find where to listen & subscribe, portfolio contests, and contact information at https://investingunscripted.com

*****************************************

To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted

Listen to the Chit Chat Stocks Podcast for discussions on stocks, financial markets, super investors, and more. Follow the show on Spotify, Apple Podcasts, or YouTube

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Subscribe to our portfolio on Savvy Trader

We open the February 2026 mailbag to answer your questions on how to handle the psychological toll of the "SaaS apocalypse" and when it actually makes sense to buy the dip. We also discuss how to assess relative risk in a portfolio, dive deep into the differences between SentinelOne and CrowdStrike (including thoughts on stock-based compensation), and reveal the "falling knife" software stocks we are most tempted to buy right now, including ServiceNow and Salesforce.

00:51 First Friday Update

02:03 Mailbag Fear in Downturns

03:56 DCA and SaaS Selloff

06:15 Deploying Cash Rules

08:43 Add to Winners Not Losers

15:49 Risk in Portfolios

20:31 Position Sizing Examples

23:28 SentinelOne Profitability Debate

28:35 SentinelOne vs CrowdStrike

30:44 Cybersecurity Basket Strategy

31:42 M&A and Buyout Odds

33:12 CareTrust REIT Update

35:00 Discord Falling Knife Picks

35:35 ServiceNow Case

37:44 PayPal Options and CEO Risk

38:33 Salesforce AI and Valuation

42:50 How We Add Positions

47:28 Enphase and Gut Conviction

50:19 Secular Trends and EV Lesson

52:05 QuantumScape Battery Bet

52:37 Wrap Up and Where to Ask

Companies mentioned: ASML, CRM, CRWD, CTRE, ENPH, NOW, PYPL, QS, S, TSLA, TSM

Find where to listen & subscribe, portfolio contests, and contact information at https://investingunscripted.com

*****************************************

To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted

Listen to the Chit Chat Stocks Podcast for discussions on stocks, financial markets, super investors, and more. Follow the show on Spotify, Apple Podcasts, or YouTube

*****************************************

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Subscribe to our portfolio on Savvy Trader

We discuss the recent market dislocation where SaaS stocks are crashing while the broader market hits all-time highs. We break down the three main fears driving the sell-off and debate which companies—like Adobe and Salesforce—are actually at risk. Finally, we share how we are handling the volatility, with Jeff buying more Shopify and Jason using a "barbell strategy" to stay sane.

02:27 Housekeeping

03:53 Episode Setup

06:37 Three AI Threats to SaaS:

09:23 Is AI Really Different?

12:59 Stock Spotlight: Adobe

18:35 The Real Issue: Moats, Stickiness, Switching Costs, and Resetting SaaS Multiples

23:18 LLMs Aren’t Free

23:49 Why SaaS Stocks Are Selling Off

25:11 Shopify vs. Toast

27:06 Disruption Timelines & Valuation Reratings

29:19 Earnings Season as the Reality Check

31:53 Tactical Moves: Selling Puts for Margin of Safety

33:02 Barbell Portfolio Strategy: Growth on One Side, Dividends on the Other

Companies mentioned: ABNB, ADBE, ASAN, CRM, CRWD, ENPH, EPR, MNDY, MSFT, NOW, O, PYPL, SHOP, SQ, TEAM, TOST, TTD

Find where to listen & subscribe, portfolio contests, and contact information at https://investingunscripted.com

*****************************************

To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted

Listen to the Chit Chat Stocks Podcast for discussions on stocks, financial markets, super investors, and more. Follow the show on Spotify, Apple Podcasts, or YouTube

*****************************************

Join our Patreon
Subscribe to our portfolio on Savvy Trader