Premium travel, engineered
from the spend you're already making.

For high-net-worth professionals and business owners spending $250K+ a year on credit cards. Maximum cashback, points, and miles. Premium cabin and 5-star redemptions as the upside.

[ HEADSHOT ]
Christopher Gapstur, PhD, PE
PhD Engineer · Licensed PE (Florida) · 15+ years engineering points strategy
15+
Years optimizing points,
miles & cashback
$1M+
Premium travel value
redeemed
100+
Countries reached
on award travel
PhD · PE
Doctorate in Engineering,
Licensed Professional Engineer
10M+
Points & miles redeemed
across self, family & associates
100+
Credit cards optimized
across decades
100+
Credit card signup
bonuses captured
5+
Marquee first-class
cabins flown
The Problem

If you're spending $250,000 a year on credit cards and capturing less than 10% of that value back, you're being robbed.

Most business owners and high earners we meet are running a $40,000 to $60,000 a month spend through a single 1% cashback card. They get the lounge. They get the travel insurance. They feel productive. They are also leaving twenty to thirty thousand dollars a year on the table in cashback, points, and signup bonuses, every year, for the same exact spending they were going to do anyway.

The fix is not complicated. It is just specific. It takes a card stack matched to your spend categories, signup bonuses captured on a deliberate cadence, redemptions made through transfer partners rather than bank portals, and points burned within twelve months instead of compounding into the asset's silent devaluation. None of this requires manufactured spending, churning, or any of the games the banks are quietly killing.

What it requires is somebody whose entire job is to know it cold, build it for your specific situation, and keep it running while you focus on what you're actually paid to do.

The Approach

A strategist's framework, not a blogger's checklist.

01 · DISCOVERY

Review your current spend.

We start with a structured review of your personal and business card spend across categories, current annual fees, point balances, and unused credits. By the end of the discovery call we have a quantified picture of exactly how much value you are leaving on the table this year.

02 · STRATEGY

Engineer the card stack.

We design a card stack matched to your specific spend categories, your tax structure, your travel patterns, and your tolerance for annual fees. You get a written implementation plan with card-by-card sequencing, signup bonus capture timing, and a quarterly review cadence to keep it current.

03 · EXECUTION

Burn the points strategically.

The points are the easy part to earn and the hardest part to spend well. We handle the award searches, the transfer partner pairings, the multi-cabin family bookings, and the late-availability sweet spots. You get premium cabin travel at three to seven cents per point in value, on dates that actually work for your calendar.

Recent Outcomes

Real redemptions. Verified value.

[ Park Hyatt St Kitts ]
Park Hyatt St Kitts
Dual room upgrade secured, family stay early 2027
Cash Value
~$TBD
Points Cost
~TBD Hyatt
[ Family of 6 to Europe ]
Family of 6 to Europe, Summer 2026
Round-trip business class · Condor outbound + Virgin Atlantic return
Cash Value
~$60K+
Points Cost
Multi-program
[ Europe Trip · Summer 2025 ]
Air France & Park Hyatt Europe, Summer 2025
6 RT Air France business · Presidential Suite at Hyatt Barcelona · Suite & connecting room at Park Hyatt Zurich
Cash Value
~$75K+
Points Cost
Multi-program

Verified redemptions from the founder's own travel. Outcomes vary by award availability, transfer bonus timing, and program changes. We do not guarantee specific point valuations or availability for future client bookings.

Engagement

Two ways to work together, one tier for one-off trips.

One-Time Engagement

Strategy Charter

$897
one-time
FOUNDING CLIENT PRICING: $697 · first 10 clients
For owner-operators who want a one-time, complete card stack review and 12-month implementation plan.
  • 30-minute Discovery Call (complimentary)
  • 90-minute working session
  • Three written deliverables: card stack plan, 12-month signup bonus sequence, redemption playbook for up to 2 target trips
  • 6 months of email implementation support (5-business-day response)
  • 6-month award-space notification window for your target trips
Apply →
Annual Retainer

Chartered Strategist

$5,997
/year or $597/mo
For operators and family principals who want their points strategy continuously run, year over year.
  • Everything in the Strategy Charter
  • Quarterly portfolio reviews (4×/yr)
  • Monthly card-move recommendations
  • Up to 6 redemption notifications per year
  • 2-business-day priority response standard
  • Annual full strategy refresh
Apply →

Engagement is by application. All inquiries held in confidence. Standalone Redemption Strategy ($300-$600 per trip) available for non-clients with specific bookings; inquire.

[ EDITORIAL PORTRAIT
placeholder ]
The Founder

Why a PhD engineer built a credit card strategy firm.

I have been quietly running this analysis for myself, my family, and the people closest to me for over fifteen years. Six continents reached on points and miles. Five marquee first class cabins flown. Multiple seven-figure point balances earned, redeemed, and reinvested. A family routinely traveling at the front of the plane on spend that was already happening.

The reason almost no one in your peer group has any of this set up is that it sits in an uncomfortable middle: too technical for the average financial advisor, too niche for the average travel agent, too high-touch for any software product, and too unglamorous to be a sexy podcast topic.

"The most valuable line item in your business spend is the one you haven't engineered yet."

Chartered Strategy exists to do this work for the small group of operators and professionals who recognize the leverage and would rather have an engineer hold the wrench than learn to use it themselves.

Read the full About page →

Credentials & Affiliations
PhD · Engineering
Professional Engineer · PE (Florida)
15+ Years in Points & Miles
Canvas Ethos LLC
Client Voice

What clients are saying.

Testimonial section is reserved for verified client quotes. Three named clients will appear here after the first cohort of founding clients completes their engagement. Until then this section remains intentionally empty rather than populated with manufactured social proof.
Frequently Asked

Questions we get from prospective clients.

What does a credit card and points consultant actually do?+

A credit card and points consultant audits a client's spending and credit card portfolio, builds a custom card stack to maximize earned points, and tells the client which redemption options convert those points into the highest dollar-equivalent value. The consultant handles strategy; the client executes simple parts like card applications and booking.

Who is Chartered Strategy built for?+

Chartered Strategy serves high-spend operators putting significant annual spend on credit cards. Typical clients include business owners running corporate spend through cards, surgeons, attorneys, engineers, contractors, entrepreneurs, inventors, fund managers, and family principals managing complex household and business expense streams. We do not serve cashback-only DIY enthusiasts or first-time card holders.

How much annual yield can a $250K+/yr operator realistically capture?+

A properly optimized $250K+/yr spend portfolio can realistically capture $50,000 or more in annual yield in many cases. This comes from stacking 10 to 15 or more signup bonuses worth 100K+ points each, redeemed at 2 to 7 cents per point on luxury hotels and premium-cabin flights, plus category multipliers on the underlying spend. Actual results vary; see our yield methodology for the full math.

Do you book travel for clients?+

No. Chartered Strategy is not a licensed travel agency. We tell clients exactly which award seats to book, which transfer partner to use, and when to act. The client or the client's office executes the booking. We engineer the redemption strategy; the client carries out the transaction.

Are you a financial advisor or fiduciary?+

No. Chartered Strategy is not a registered investment advisor, fiduciary, or financial advisor. We are not regulated by the SEC, FINRA, or any state securities regulator. We provide consulting services on credit card and rewards strategy only. Clients should consult licensed financial, tax, and legal professionals for advice in those domains.

How are affiliate relationships disclosed?+

Chartered Strategy earns commissions on certain credit card applications and product referrals. These relationships are disclosed in our footer, on our Affiliate Disclosure page, and within client deliverables. Affiliate relationships do not influence recommendations. When an affiliate-linked card is not the best option, we direct clients to the better one.

What does an engagement cost?+

Strategy Charter engagements are $897 one-time (or $697 founding-client pricing for the first 10 clients in exchange for a named testimonial). Includes a written card stack plan, 12-month signup bonus sequence, and a redemption playbook for up to 2 target trips. Chartered Strategist annual retainer is $5,997 per year or $597 per month for quarterly reviews, monthly card-move recommendations, and up to 6 redemption notifications per year. Standalone Redemption Strategy is $300 to $600 per trip.

How is Chartered Strategy different from a travel agent or a content site like The Points Guy?+

A travel agent books trips. A content site like The Points Guy publishes general advice for a broad audience. Chartered Strategy operates as a private one-to-one advisory practice. We audit your specific spend portfolio, build your custom strategy, and tell you exactly which redemptions to execute and when. Done-for-you, not DIY.

Insights

The Chartered Letter.

A weekly note for operators and professionals serious about engineering their spend. One sweet-spot redemption. One card move. One field report. No fluff. No affiliate dump. Friday morning, free.

By subscribing you agree to receive emails from Chartered Strategy. Unsubscribe at any time. Canvas Ethos LLC, Florida.