Overview of Points & Miles in 2026: What's New, What's Dying & What's Next (with Brian M)
Chris Hutchins interviews Brian M about the current state and near-future of the points & miles world. They cover recent industry shakeups (Bilt’s big relaunch, Mesa’s abrupt shutdown), what that means for cardholders, how to think about keeping or cancelling cards, practical trip‑planning strategies to preserve flexibility, and predictions for 2026 (startups, debit co‑brands, tooling + AI). The conversation mixes high‑level strategy with concrete examples and a useful deep dive into how Bilt’s new “built cash” mechanic actually changes effective earning rates.
Key takeaways
- Bilt relaunched with three new cards and a new “built cash” layer; the changes add complexity but aim for sustainability. Many implementation details remain unclear (redemption mechanics, caps, eligibility).
- Mesa’s rapid shutdown is a cautionary tale about startup-run transferable points programs; Mesa did cash out balances as statement credits, but the incident highlights risk.
- Startups and third‑party platforms (Ascenda, Silo, etc.) are enabling more transferable‑points programs — more opportunity but also more counterparty risk.
- For trip planning, prioritize booking flexibility, define who/what/when/why/how, book at schedule open when possible, and continuously monitor/garden reservations.
- Practical card management rules: don’t cancel in the first year; value credits realistically; ask for retention offers; consider downgrading to preserve account age; manage issuer-specific approval/credit allocation rules.
News & context
Bilt relaunch (three new cards; built cash mechanic)
- Bilt moved off Wells Fargo and partnered with Cardless; launched three cards:
- No-fee card — 1x rewards on everything (plus built cash).
- Mid-tier (Obsidian-ish) — 3x on dining OR groceries (you choose), 2x travel, 1x everything; caps apply on some categories.
- Palladium — 2x on everyday spend; comes with a yearly built cash credit (~$200) and higher annual fee.
- New mechanic: you earn “built cash” (4% on some spending) and can convert built cash into points for rent/mortgage: $30 built cash = 1,000 points.
- Open questions (at time of interview): How freely can built cash be redeemed (genuine cash vs monthly credits), whether converted/welcome bonuses will be available to current cardholders, exact exclusions (tax, business, marketplace transactions), and category caps.
Bilt insight (calculation example)
- If your annual rent/mortgage = $10,000, unlocking 10,000 points on those payments requires $300 built cash.
- At 4% built cash earnings, you must spend $7,500 on the card to generate $300 built cash. So:
- Required spend ≈ 0.75 × annual rent/mortgage (quick formula).
- That $7,500 spend also earns base card points → the effective multiplier can be much higher than the marketed 1x/2x when you include unlocked rent points. Example: a 1x card + built cash unlock can behave like ~2.33x up to the mortgage amount; Palladium (2x + built cash) can approach ~3.33x up to the cap.
- Caveat: caps, exclusions, and exact built cash redemption details will materially change valuation.
Mesa shutdown
- Mesa (startup card with generous categories and mortgage earning) shut down abruptly; points were redeemed as statement credits rather than transferred to partners.
- Lesson: transferable points programs from startups can be lucrative but risky; consider point custody and exit options.
New players & mechanics
- Ascenda and similar third parties let startups spin up transferable currencies quickly.
- Silo (brokerage-based program) is testing ongoing brokerage bonuses in transferable points — another emerging model that mixes financial products and loyalty currencies.
How Brian thinks about cards, annual fees, and retention
Rules of thumb
- Never cancel within the first 12 months (capture the year’s benefits and avoid hurting history).
- When an annual fee is due:
- Calculate the real value you’ll use from credits (face value often overstates usefulness).
- Ask the issuer about retention offers (especially Amex historically, though offers feel less generous now).
- Consider downgrading to a no-fee product to preserve account age/history.
- If you choose to cancel, do it after the fee posts and within the refund/window you can get it back if needed.
- Preserve long‑open accounts where possible (average age of accounts matters for credit score).
- If you can’t get a new issuer approval, consider reallocating credit lines or asking issuer to move limits (issuer rules vary widely).
Business vs personal cards
- Employers commonly reimburse employee personal spending for business expenses — in practice many people use personal cards for business travel and vice versa, but check issuer terms: some card programs exclude certain transactions (gift cards, person‑to‑person payments, taxes, marketplace payments, business transactions) from earning rewards.
Approvals strategy
- Denials are common and issuer‑specific. Strategies:
- Reconsideration calls.
- Reduce/unallocate existing limits with the issuer before applying.
- Apply to different issuers with different standards.
- Understand issuer‑specific rules around reallocating credit between business and personal lines.
Trip planning: Brian’s process & practical booking tips
Start with constraints: Who / Where / When / Why / How
- Who: party size, special needs (aisle seat, accessibility), number of award seats required.
- Where & When: is the destination fixed (e.g., specific resort) or flexible? School calendars restrict many families.
- Why & How: specific purpose (ski, family visit, all‑inclusive), nonstop vs connections, driving vs flying.
Booking principles
- Value flexibility highly — pandemic-era flexible cancellation and award policies matter.
- Book the best available option you're willing to take, then “garden” (monitor and rebook better options as they appear).
- For highly flexible travel windows, book early at schedule open (≈11–13 months out) to capture award space (especially for families of 3–4).
- Set alerts (Seats.Aero, PointsPath, Google Flights, award trackers) for fare drops and partner availability.
- Evaluate elite benefits: lounge access, extra legroom, guest rules — sometimes splitting reservations or leveraging different people’s status can be valuable.
- Changing award destination or open‑jaw rules vary by program; many programs restrict destination changes unless impacted by a schedule change or waiver.
Hotels, connecting rooms & suites
- Decide if you need space: suite, connecting rooms, or vacation rental.
- Hyatt suite upgrade awards (and some certs) can confirm suites at booking — useful for families.
- Hyatt family plan / Hilton confirmed connecting rooms can be useful but availability varies and often requires phone agent assistance.
- Timeshares (Marriott/Hilton/Hyatt/Wyndham) can be a good hybrid between resorts and vacation rentals — often strong value for larger units.
Monitoring & rebooking
- Keep searching after booking — award space and paid fares change.
- If better options appear that materially improve the trip, rebook if the award rules/taxes/refund profile justify it.
Tools recommended
- PointsPath (good domestic + Google Flights integration)
- Seats.Aero (international award searching)
- Traditional brute‑force search engines and issuer sites (sometimes issuer‑specific discounts are not visible elsewhere)
Predictions & 2026 trends
- More startups will launch transferable points/currencies using third‑party engines (good opportunity + counterparty risk).
- Co‑branded debit cards and more alternative loyalty inflows (brokerage bonuses, fintech offers).
- Elite benefits will shift toward non‑travel perks and partner options (milestone awards, points usable beyond seat upgrades).
- Continued evolution in airline product mix (premium economy/premium domestic seating is growing).
- AI and tooling will improve award searching, automated re‑shopping, and agent‑like booking assistants — eventually enabling software to manage bookings and changes on your behalf.
- Regulatory ideas (e.g., a temporary credit card interest cap) get proposed but are unlikely to pass; second‑order effects would be complicated if they did.
Notable insights / quotes
- “I value booking flexibility higher than most.” — Brian on why he books flexible award options and gardens bookings.
- “If a friend asked me to buy an Oura ring with my hotel credit and I’d get $50, I’d probably say yes.” — a practical reminder that face value of credits often overstates personal utility.
- Quick formula for Bilt built cash planning: required spend ≈ 0.75 × annual rent/mortgage to unlock equivalent points.
Actionable checklist (for listeners)
- If you have Bilt:
- Decide convert vs reapply (consider approval odds, signup bonus possibility, whether conversion + signup is allowed — check the latest Bilt communications).
- Use the 0.75 × rent formula to estimate how much card spend you’d need to fully unlock rent points.
- Watch Bilt AMAs and T&Cs for built cash redemption mechanics and exclusions.
- If you hold cards with big annual fees:
- Don’t cancel within the first year.
- Tally realistic value of credits you will actually use.
- Ask for retention offers before deciding; consider downgrading to a no‑fee product to preserve age.
- For upcoming trips:
- Define constraints (who/where/when/why/how) before hunting awards.
- Book acceptable options early, set alerts, and garden bookings.
- Use tools like PointsPath and Seats.Aero and be mindful of issuer‑only discounts.
- If applying for cards and getting denials:
- Consider reallocating credit, reducing limits, calling reconsideration, or applying to alternative issuers with different approval policies.
Final thought
The points & miles space in 2026 looks like a mix of more creative startup offerings and more complexity from incumbent issuers. That creates opportunity (new transferable currencies, better tooling, novel co‑brands) but also more need for cautious, rules‑aware strategy: value credits realistically, prioritize flexibility, monitor bookings, and treat startup points like a higher‑risk asset.