Chit Chat Stocks: "Our 5 Best Stocks To Buy TODAY (Plus, Our Personal Portfolio Returns)"

Date: September 17, 2025
Hosts: Ryan Henderson & Brett Schafer

Episode Overview

In their annual special, Ryan and Brett break down their personal investment portfolios, openly sharing returns, major wins and losses, and how their holdings have evolved over the last year. They then reveal their five top stocks to buy right now—both from current portfolio holdings and their watchlists—highlighting the reasoning behind each pick. The episode closes with honest discussion about the stocks they’re considering selling and the new names at the top of their watchlists.

Key Discussion Points & Insights

1. Portfolio Performance: Candid Look at Results & Lessons

Brett Schafer’s Portfolio (02:05–09:00)

• Brokerages: Uses Interactive Brokers for both taxable and Roth IRA accounts, starts tracking using Portcido in July 2024.
• Total Return: Up 22.7% year-to-date in 2025, compared to S&P 500 at 17%.
• Attribution Analysis:
  • Top Contributors (By Value):
    • Coupang
    • Nelnet
    • Interactive Brokers
    • Nintendo
    • Oscar Health
    • Alsea Group (Latin American franchisee for Domino's, Starbucks, Burger King)
    • Grupo Aeroportuario del Centro Norte (OMAB, Mexican airports)
  • Top Detractors:
    • Remitly
    • Portillo’s
    • Harbor Diversified
    • Tesla (short position, ~6% of assets)

Quote:
“Flows may impact performance in the short run, but growth and free cash flow per share will drive performance over a decade.” – Brett (05:20)

Ryan Henderson’s Portfolio (10:01–14:47)

• Transition: Closed Arch Capital fund in 2023, began personal investing December 2023 with Portcido.
• Total Return: 38.7% since Dec 2023, S&P 500 up 67% in same window. Cites a major mistake in Harbor Diversified (down 74%).
• Adjusted Returns: Excluding Harbor Diversified, would have been +91% vs S&P 500’s +67%.
• Past Year: +62% over the last 12 months, beating S&P 500 (+15%).
• Top Winners (By Percentage):
  • Coupang (+88%)
  • Philip Morris (+76%)
  • Autodesk
  • Google
  • British American Tobacco
• Top Losers:
  • Harbor Diversified
  • Semrush
  • Remitly

Quote:
“My returns would have been 50% higher if not for sizing Harbor Diversified so poorly.” – Ryan (11:42)

2. Portfolio Holdings & Position Sizing (15:59–27:11)

Brett’s Top 10 Positions

• Largest Holdings:
  • Nelnet (20%)
  • Coupang (17%)
  • Remitly (14%)
  • (rest under 10%: Oscar Health, TLT, OMAB, Interactive Brokers, Nintendo, Airbnb, Portillo’s)
• Concentration: Top 3 = ~50%, Top 4 = 60%
• Comfortable with concentration? “Sure, yeah.” – Brett (19:02)
• Wishes Interactive Brokers was a bigger position, but is wary of increasing Remitly due to its recent performance.

Ryan’s Top 10 Positions

• Coupang (17%)
• Remitly
• Wise
• Philip Morris
• Google
• Adobe
• OMAB
• Harbor Diversified
• Nelnet (4.4%)
• DR Horton
• Has 20+ stocks, with plan to keep top 10 as 60–70% of portfolio
• Keeps small “tracker” positions to monitor companies closely.

Quote:
“I watch a company’s progress closer if I actually own some shares.” – Ryan (23:42)

3. Recent Trades & Portfolio Changes (27:11–31:13)

Brett’s Major Trades

• Adds: Coupang (averaged up), Remitly, Nelnet, Portillo’s (added after insider buying), Airbnb, Interactive Brokers.
• Sells/Trims: Full exit from Philip Morris into Airbnb and Interactive Brokers, exited GoGo due to competitive concerns.

Ryan’s Major Trades

• Added Most: Wise, Remitly, Google.
• Trimmed: Philip Morris after a strong run, redeployed elsewhere.

4. Best Buys Today: Top 3 Stocks To Buy NOW (32:04–47:54)

1. Remitly Global [Both Hosts]

• Rationale: Leader in digital remittances, rapid customer growth, ongoing product launches, clear uptrend in operating leverage.
• Valuation: Trades at ~3x EV/Gross Profit (Brett).
• Conviction: “When I think about stocks in my portfolio that have the highest possibility of being a 10-bagger, Remitly is probably number one.” – Ryan (34:49)
• Caveats: Already large positions for both; unlikely to add much but would be top choice if building from scratch.
• Growth Fact:
  “They’ve gone from less than a million active customers to eight and a half million in five years. That is astounding growth.” – Ryan (35:19)

2. The Real Brokerage (REAX) [Brett]

• Rationale: Cloud-based residential real estate broker, fastest-growing company covered on show, revenue up 59% YoY.
• Position Sizing: Would make 3-4% due to high risk/small cap.

Quote:
“I called this the fastest growing company we’ve ever covered on the podcast for a reason.” – Brett (39:50)

2. Amazon [Ryan]

• Rationale: Fulfillment and logistics moat, AWS possibly undervalued, trading near its cheapest EV/EBIT ever.
• On Competition:
  “If Amazon stopped investing or improving its own delivery ... I think it would take almost 10 years for any competitor to catch up.” – Ryan (41:42)

3. Airbnb [Brett]

• Rationale: Unique lodging supply (listing-level moat), dominant in US/Canada but room to grow internationally (only 30% of bookings outside Anglophone countries), new product optionality (e.g. experiences), high margin potential, founder-led.
• Valuation: EV/EBIT ~24, with buybacks ongoing.

3. Corporación América Airports [Ryan]

• Rationale: 53 airports globally, mainly South America/Argentina, airport leasing = toll road economics, extending contracts for free with government, reasonable valuation (EV/EBIT <10), expects 10%+ earnings growth.

5. Stocks On The Chopping Block (49:38–58:13)

Portillo’s [Brett]

• Concerns: Cut guidance, declining comp sales, rising costs, margins sliding, debt.
• Positives: Could become a 20% FCF yield play, but “been disappointing.”
• Holding: Reduced to 5%, “not adding,” but could still be a big winner if turnaround materializes.

Harbor Diversified [Both]

• Status: Major drag on Ryan’s returns; hard to trade due to delisting, waiting for liquidity event or value realization.
• Plan: Might set a “leaving an open sell order at $1.50 just to see if someone grabs them.” – Ryan (54:44)

Ally Financial & Semrush [Ryan]

• Ally: Losing edge vs. neobanks, stagnant deposits, competitive pressure from SoFi.
  “I worry about Ally’s long-term outlook.”
• Semrush: Execution issues, missed guidance, founder CEO ousted, shifting upmarket failed.

6. Stocks On Watchlists (58:44–64:45)

Brett’s Picks

• Lululemon: “EV/EBIT of 8 may make me break my never invest in apparel rule.”
• Sprouts Farmers Market: Down 28%, watching for cheaper entry.
• Philip Morris: Sold at $160, would buy back around $130–$140/share.

Ryan’s Picks

• American Express: Premium customer base, strong compounding, EB/EBIT ~17.
• Grab Holdings: Southeast Asia’s “super app” (mobility, food delivery), “great network effect.”
• Monday.com: SaaS business with resilient growth versus peers; “need to do more work, but everyone raves about the software.”

7. Takeaways: Portfolio Updates & Lessons (64:45–67:37)

Brett:

• Holds 3% cash (in SGov ETF for yield).
• Plans to incrementally increase Airbnb position from 5% to possibly up to 10%, citing conviction.
• Emphasizes the importance of proper sizing for high-quality businesses: “Don’t be afraid ... to size up the position a little bit. And you can also do that over time.”

Ryan:

• Admits to neglecting size optimization for holdings like Airbnb, Interactive Brokers, Nelnet.
• Committed to being more intentional about increasing conviction holdings over time.

Memorable Quotes & Moments

• On Harbor Diversified’s drag:
  “My returns would have been 50% higher if not for sizing Harbor Diversified so poorly.” (11:42)
• On portfolio concentration:
  “Your top four positions, I just did the math roughly here, make up 60% of your portfolio ... Do you feel comfortable?”
  “Sure. Yeah.” – Brett (18:53, 19:02)
• Traps & Lessons:
  “You fell for the insider buyers trap.” – Ryan, re: Portillo’s (31:10)
• On Remitly’s growth:
  “They’ve gone from less than a million active customers to eight and a half million in five years.” – Ryan (35:19)
• On learning from position sizing:
  “Don’t be afraid ... to size up the position a little bit.” – Ryan (67:36)

Timestamps for Key Segments

• 02:05 Brett’s returns, contributors/detractors
• 10:01 Ryan’s returns, major lessons
• 15:59 Full portfolio breakdowns
• 27:11 Trade and rebalancing activity
• 32:04 5 best stocks to buy now (main section)
• 49:38 Stocks on the chopping block
• 58:44 Portfolio watchlists
• 64:45 Portfolio changes, lessons, wrap-up

The Episode’s Original Tone & Vibe

Ryan and Brett maintain a candid, data-driven, and often self-deprecating tone, freely discussing their mistakes as well as their wins. They debate position sizing and portfolio concentration, challenge each other on high-conviction picks, and admit where emotions or behavioral finance have influenced them (“the insider buyer’s trap”). Throughout, the show is accessible, pragmatic, and investor-friendly, emphasizing both transparency and flexibility in portfolio management.

For Further Details

• Transcripted quotes and more data: Fiscal AI platform.
• More research, charts, and portfolios: Chit Chat Stocks Substack.
• Feedback, follow-up questions: DM or email as mentioned on-show.

End of summary.