A private practice for high-spend operators.
Chartered Strategy is a private credit card and rewards advisory practice. We work with a small group of high-spend operators to capture the maximum return from spend they are already making, then convert that return into premium travel, cashback, and other tangible outcomes.
The founder
Chartered Strategy was founded by Christopher Gapstur, PhD, PE, a PhD engineer and a Professional Engineer licensed in Florida.
He has spent over 15 years personally redeeming millions of points and miles for luxury hotels, business class, and first class travel across six continents. He currently holds more than 50 credit cards and has held hundreds of cards across every major US issuer over the years. He has run quarterly portfolio reviews on his own spend through multiple economic cycles, optimized signup bonus stacking across every issuer's rule set, and watched the points game evolve through award devaluations, transfer-partner changes, and the rise of premium-cabin scarcity.
The work that Chartered Strategy does for clients is the same work Dr. Chris has been doing for himself, his family, and a small group of close friends for over a decade and a half. The methodology is built on an engineer's analytical training: measure the inputs, model the outcomes, optimize the variables that actually move the needle, and discard the rest.
What "Chartered" means
The name carries two intentional meanings. The first is methodological: chartered as in deliberately designed, carefully structured, and engineered to a plan. The second is destinational: chartered as in chartered private aviation, chartered yachts, and chartered luxury experiences. Both meanings point to the same outcome. Premium travel, engineered.
Chartered Strategy is not affiliated with the CFA Institute, the American College of Financial Services, the Engineering Council UK, or any other professional body that issues a "Chartered" designation. The word in our brand name is descriptive of our methodology and our outcomes, not a regulated credential.
Who we serve
Chartered Strategy is built for the high-spend operator. Our clients include business owners running significant card spend through their companies, high-earning professionals (surgeons, attorneys, engineers, contractors, entrepreneurs, inventors, fund managers), and family principals managing complex household and business expense streams across multiple cards.
How we work
Every engagement starts with a complimentary 30-minute Discovery Call. We confirm fit, your spend volume, your card history, and your travel goals.
If we are a fit, we book a 90-minute working session. We review your current card stack, your spend pattern, your credit profile, your household and business mix, and your target trips. Within 5 business days of that session we deliver three written documents: a custom card stack plan, a 12-month signup bonus sequence mapped to your cash flow, and a redemption playbook calibrated to up to 2 target trips.
From there, we provide 6 months of email implementation support for card applications, approval questions, and category-bonus questions, with a 5-business-day response standard. For 6 months after engagement start, we proactively monitor award space for your target trips. When sweet-spot award space opens, we notify you exactly which awards to book, which transfer partner to use, and when. You or your office executes the booking.
Clients who want continuous optimization year-over-year engage Chartered Strategy as a Chartered Strategist retainer with quarterly portfolio reviews, monthly card-move recommendations, up to 6 redemption notifications per year, a 2-business-day priority response standard, and an annual strategy refresh.
What we are not
Chartered Strategy is not a financial advisor, a credit counselor, a tax professional, or a licensed travel agency. We do not manage your money. We do not file your taxes. We do not book your travel directly. We engineer the strategy, run the playbook, and tell you exactly what to execute and when. You or your office make the booking calls. We do the thinking so you do not have to.
Editorial and recommendation standards
Chartered Strategy earns commissions on certain credit card applications and other product referrals. These affiliate relationships do not influence our recommendations. We recommend cards and products based on client fit, not commission structure. When an affiliate-linked product is genuinely not the best option for a client, we say so and direct them to the better option, even when no commission is available to us.
Contact
Email: [email protected]
Chartered Strategy is a DBA of Canvas Ethos LLC, a Florida limited liability company.