Chit Chat Stocks – “Rebuilding Our Portfolios From Scratch (Stocks We'd Buy Today)”

Hosts: Ryan Henderson & Brett Schaefer
Date: April 8, 2026
Episode Theme:
Ryan and Brett take on a listener’s challenge: if they had to rebuild their portfolios from scratch (10 stocks, 5 each), choosing only companies they've never owned, which would they buy today and why? The episode is packed with candid investment discussion, deep dives into each pick, market perspective, healthy debate, and insights into their investing frameworks.

Main Theme & Purpose

Responding to a great listener prompt, the hosts reconstruct hypothetical 10-stock portfolios using only stocks they do not currently own and have never owned. Each host picks 5 names, showcases their reasoning, market outlook, and personal investing philosophies—prioritizing valuation and business durability, rather than speculative wish lists.

Portfolio Construction Rules & Approach

• Only stocks never owned or currently held.
• Must be BUYABLE right now at current prices (no “great stock, bad price” picks).
• Mix of growth, durability, business models (digital vs. physical), and international exposure.
• Equal weighting: five stocks per host, each 20% of a new portfolio.
• Focus on long-term compounding, not wild speculation.

Key Insight:

“This isn't a list of stocks we wish we owned but are waiting for. It’s what we’d actually buy right now, if building a fresh portfolio.” – Ryan, [02:58]

THE STOCK PICKS: Ten Fresh Names

Ryan’s Picks

1. Wix.com (WIX)

   • Website-building SaaS & growing AI tool (base 44).
   • Deep value—multi-year revenue growth but stock flat, market skeptical about AI disruption.
   • Management just repurchased 32% (!) of shares in a Dutch auction at prices above where shares trade now.
   • “Of all the companies on my list, I'll just go ahead and say this. This is the business model that I like the least...but I think this is a ludicrous valuation.” – Ryan, [12:04]

2. Uber (UBER)

   • Ride-share & food delivery global platform.
   • Focus on competitive resilience, network scale, and questions about autonomous vehicles.
   • Believes Uber’s two-sided network effect and platform scale will still matter (even in AV future).
   • “Every time I think, this is like a pretty phenomenal network...” – Ryan, [21:05]
   • Engages Brett in debate over AV disintermediation, cost dynamics, and international growth.

3. Grupo Aeroportuario del Pacífico (Pacifico Airports)

   • Operator of 14 Mexican airports (inc. Tijuana, Guadalajara, Cabo).
   • Durable, inflation-linked, natural monopoly with strong tourism tailwinds.
   • “I think airports are extremely durable businesses…hard to go wrong owning any of the Mexican airports.” – Ryan, [44:29]

4. Grab Holdings (GRAB)

   • Southeast Asia’s “Uber+DoorDash.”
   • Winner-take-most in its markets, now profitable after years of losses.
   • Network effects, multi-country leadership, and expansion into digital payments.
   • “This is the ideal operating leverage chart…now this last two quarters, trailing 12 months they’ve had GAAP operating profits.” – Ryan, [56:25]

5. American Express (AXP)

   • Well-moated payments & membership business.
   • Brand has broadened from ‘ultra-wealthy only’ to aspirational for millions, with durable pricing power.
   • “They’ve added 40 million new cardholders…while maintaining an aspirational brand…tons of pricing power there.” – Ryan, [63:41]

Brett’s Picks

1. Amazon (AMZN)

   • Everything store + cloud (AWS + many more).
   • Capex “overkill” and ambiguity criticized, but Brett highlights normalized earnings power as undervalued.
   • “If we look at revenue, $717bn in 2025. Grow that…that’s $1.25 trillion in five years. 15% op margin…that’s $190bn in earnings…Feels like you get a decent outcome.” – Brett, [16:48]

2. Nu Holdings (NuBank, NU)

   • Digital bank in Brazil, Mexico, Colombia.

   • 100 million active customers, huge operating leverage, expanding profits, “replacing broken incumbents.”

   • “This combination of poorly operated banks…with smartphone usage and payments adoption…a lollapalooza tailwind. That’s…why NuBank succeeds.” – Brett, [34:32]

3. Grupo Aeroportuario del Sureste (“Southern Airports”)

   • Another Mexican/LatAm airport operator (owns Cancun, San Juan, Medellin).
   • Diversifying beyond Mexico via acquisitions. Trading at “sub-8x forward EBITDA.”
   • “These have been 100-baggers since 2001…2030 could be the same story.” – Brett, [44:34]

4. Leidos (LDOS)

   • Software and solutions for defense, intelligence, government health.
   • Not exciting—“boring company in a niche of a niche”—but massive backlog, stable contracts, consistent buybacks, and shareholder returns.
   • “...I feel like it’s really, really hard to lose with this thing...” – Brett, [59:55]

5. Hagerty (HGTY)

   • Specialty auto insurance for classic cars, enthusiast membership, and auction marketplace.
   • Durable, high growth, monopoly-esque in its niche. Markel partnership shifts all risk and reward to Hagerty (short-term GAAP hit, long-term upside).
   • “Kind of a monopoly player in its niche, I think. And I feel like it’s durable.” – Brett, [68:54]

Notable Debates, Moments & Quotes

• Uber vs. Autonomous Vehicles Debate:

  • [21:05–29:40] Ryan and Brett go back-and-forth on whether Uber’s core value will withstand AV disruption, Waymo’s threat, and whether Uber can remain lowest cost.
  • “Oscillating demand needs flexible supply… Uber solves that.” – Ryan, [22:16]
  • “I think they can easily get a ton of Waymo demand—they own YouTube, Gmail—Alphabet platforms can promote anything.” – Brett, [25:03]

• Amazon – Capex Anxiety:

  • Brett details Amazon’s massive investments in AI, comparing cash burn and ROI to WeWork.
  • “Rightfully being called a financial terrorist by a lot of people online…” – Brett, [13:08]

• NuBank & Emerging Markets Banking Pain:

  • [34:17–40:11] NuBank’s customer growth comes from “terrible customer experiences” with incumbents.
  • “Banco de Colombia just stole my money… (story of lost ATM deposit, endless lines).” – Brett, [40:00]

• Airport Operators as Natural Monopolies:

  • [41:33–44:29] Discussion on why Mexican airports are so robust—structural inflation hedges, regulatory barriers, and unique assets (e.g., Tijuana’s cross-border traffic).

• Leidos – Big Moat, Quiet Niche:

  • “...super boring company that operates in a niche of a niche that no one cares about...but better than market returns.” – Ryan, [59:55]

Rapid Hits & Wrap-Up Questions

• Both agree Mexican airport stocks are perhaps the best combo of safety and upside right now.
• Brett: “Southern airports would be number one. I think the price is pretty good…” [70:23]
• Ryan: “Of my picks, I might go with New Bank. But Grab is up there.” [71:10]
• Cautious about consumer credit risk at NuBank, but acknowledge strong underwriting.

Key Discussion Timestamps

• Intro and Ground Rules: [00:50 – 07:54]
• Wix (Ryan #1): [07:54 – 13:08]
• Amazon (Brett #1): [13:08 – 20:10]
• Uber (Ryan #2, DEBATE): [21:05 – 34:17]
• NuBank (Brett #2): [34:17 – 40:11]
• Pacifico Airports (Ryan #3): [40:38 – 44:29]
• Southern Airports (Brett #3): [44:29 – 51:59]
• Grab Holdings (Ryan #4): [52:06 – 57:20]
• Leidos (Brett #4): [57:20 – 59:55]
• American Express (Ryan #5): [60:29 – 65:58]
• Hagerty (Brett #5): [66:57 – 69:43]
• Final Reflection & Rankings: [69:43 – 72:21]

Language & Tone Highlights

• Candid, occasionally irreverent (“financial terrorist”), but grounded in fundamentals.
• Debate is playful, evidence-based, and pushes each host to refine their arguments.
• Breaths of humor: “Not a soul. It's just a money pit. There's one medical [startup], Zoox...” – Brett on Amazon’s projects, [16:48]
• Willingly admit uncertainties (platform risk, AV threats, international market unknowns).

Summary Table: Portfolio Picks

| Host | Stock (Ticker) | Core Thesis / Value Driver | |-------|------------------------------------------------------|--------------------------------------------------------| | Ryan | Wix (WIX) | Value, misunderstood, management buybacks | | Ryan | Uber (UBER) | Platform scale, network, international growth | | Ryan | Pacifico Airports (PAC) | Natural monopoly, rising travel, inflation hedge | | Ryan | Grab Holdings (GRAB) | Southeast Asia leader, profits inflecting, network | | Ryan | American Express (AXP) | Brand/power, fee growth, full-stack earnings | | Brett | Amazon (AMZN) | Normalizing earnings, diversified revenue, upside | | Brett | Nu Holdings (NU) | Hypergrowth, operating leverage, digital bank moat | | Brett | Southern Airports (ASUR) | Airport monopoly, LatAm expansion, cheap on EBITDA | | Brett | Leidos (LDOS) | Gov. contracts, sticky, cash generator | | Brett | Hagerty (HGTY) | Enthusiast monopoly, insurance + marketplace, growth |

Closing Thoughts

A must-listen for stock enthusiasts interested in compounding, global ideas, and “unloved” industries.
The episode showcases Ryan and Brett’s investor mindset: skeptical, valuation aware, and always hunting for the next durable winner—with just the right amount of banter and humility.

Best Quotes

• “Oscillating demand needs flexible supply. Uber solves that.” — Ryan, [22:16]
• “They’ve added 40 million new [AmEx] cardholders… tons of pricing power there.” — Ryan, [63:41]
• “Banco de Colombia just stole my money… you can see why Mercado Pago and NuBank succeed.” — Brett, [40:00]
• “These are 100-baggers since 2001… 2030 could be the same story.” — Brett, [44:34]

TL;DR:
Smart, long-term investing is about durable business models, not just tech hype. The winners of tomorrow might just be hiding in plain sight—airports, banks, or even classic car insurance!