Points & miles 101 with Ross Alcorn: Turn your credit card rewards into free travel
When we met Ross Alcorn — CEO and founder of Itinerary Boss — at FinCon this past September, we immediately asked him to be a guest on The Finance Girlies. He's spent years mastering the art of using points and miles to travel for free, something we’re very much still learning how to do.
Here's what we loved about talking with Ross: He doesn't gatekeep this information. He doesn't make you feel dumb for not knowing transfer partners from award availability. Instead, he breaks down exactly how to build a points strategy that actually works for your life — whether you're taking one big trip a year or planning constant getaways.
So if you’ve ever seen someone brag about their free business class trip and wondered how they pulled it off, this episode is for you.
⏰ Episode Timestamps
[3:00] Ross's origin story — how he discovered travel rewards
[5:00] Building your foundation: Why budgeting comes first
[8:00] Choosing your first credit card & debunking the annual fee myth
[14:00] Cash back vs. points: Why points absolutely win for travel
[17:00] Transferring points 101
[25:00] Is learning points and miles worth it if you don't travel constantly?
[28:00] Planning ahead: how to strategize big purchases for bonus points
[35:00] Stretching your points for maximum flexibility
[38:00] Ross's dream honeymoon in Thailand & Bali
Building your foundation: Budgeting comes first
Before you even think about optimizing your rewards, you need to get your budget in order.
Ross is clear on this: budgeting comes first. Don't spend more than you make. Only after you have that foundation in place should you layer in a rewards strategy.
Because here's the thing — rewards aren't magic. They're a bonus on spending you're already doing. If you're overspending just to chase them, you've completely defeated the purpose.
Choosing your first credit card (and why you should stop worrying about annual fees)
Ross has about 15 credit cards — but he recommends starting with just one. You don't need a wallet full of cards to win at this game. Get the hang of redeeming points and miles first, then upgrade your strategy with additional cards if you want to.
Not sure where to start? Ross says the key to choosing the right card is matching it to your spending habits. If you're single and travel constantly, a travel-focused card makes sense. If you're married with kids and groceries are your biggest expense, a flat 2x points card might be smarter. If you know a big expense is coming (moving, wedding, home renovation), that's the perfect time to grab a card with a juicy welcome bonus that aligns with that spending.
Here are a few of Ross’s favorite cards he recommends to beginners:
Capital One Venture X — $395 annual fee (includes $300 travel credit + 10,000 anniversary points). Great for frequent travelers who want straightforward earning.
Chase Sapphire Preferred — $95 annual fee with solid travel protections and good earning rates on travel and dining. A solid middle ground for beginners.
About those annual fees...
One of the biggest misconceptions? That annual fees are deal-breakers. They're not.
Ross breaks down the math: his $95 annual fee card comes with a $300 travel credit and 10,000 anniversary points. When you factor in those benefits, the fee essentially pays for itself. A $395 annual fee sounds expensive until you realize it comes with a $300 travel credit, $120 in streaming credits, and 10,000 bonus points—suddenly that fee is working for you, not against you.
Cash back vs. points: Why points win for travel
One question Ross gets often is, “But what about cash back?”
And honestly, we were also wondering how cash back plays a role in travel hacking. Turns out, it doesn’t. Here’s why:
If you're getting 2% cash back, that sounds good. But 2x points can turn into 2, 3, 4, 5—even 7x their value when redeemed strategically.
Ross used 25,000 Capital One miles for a $600 flight. That's nearly 3x the value. With business class or luxury hotels? The multiplier gets even crazier.
"When you start to redeem them for 2, 3, 4, 5, 6, 7 times, that's where [points] outweigh cash back significantly," he says.
Caveat: If you're not interested in traveling, cash back might be the better move—it's simpler and doesn't require learning all this stuff.
Transferring points: It's simpler than you think
Booking through the credit card portal feels easy. But it’s (usually) not the best move. The portal is just where you move your points — the actual booking should happen with the airline or hotel directly.
Here’s why: Through the portal, your points are worth 1-1.25 cents each. Transfer them to a partner? You can get 2-7x the value. That $700 flight costs 70,000 points through the portal, but those same 70,000 points could book a $3,000-$4,000 business class flight.
Here’s how it works:
Log into your rewards portal, find "Transfer Rewards to Partners," and pick where you want your points to go based on where you're traveling.
Pro tip: Know your hub. If you're in Minneapolis, you're Delta. Charlotte? American. Understanding your airline alliance makes finding good availability way easier.
Plan ahead and stack bonuses
One of the smartest moves you can make is to align big expenses with credit card bonuses.
Ross and his wife got married and knew they'd have tons of wedding expenses. They got a hotel card with a welcome bonus (if they spent $5,000 in 90 days, which they'd hit no problem) and earned five free hotel nights — plus 26x points on every dollar spent at their wedding hotel.
You don't need to constantly open new cards. Just think strategically about when big expenses are coming and pick cards with bonuses that match that timing.
Are points and miles actually worth your time?
Here's the real question: if you're not traveling constantly, is it worth learning these strategies?
According to Ross, absolutely. Even if you only take one or two trips a year, you can likely cover most (or all) of your flights and hotels with strategic earning and redemption.
"If you're taking a few trips, even for long weekends and just one big trip — this is worth your time because there's ways you can offset every single flight cost, every single hotel cost," Ross explains.
The people who benefit most? Those with a few big expenses coming up or one major trip a year. Plan ahead, get the right card, and watch your points stretch.
TL;DR
Points don’t have to be complicated — credit card companies just make them seem that way.
Start with a solid budget and simple card that matches your spending.
Don’t shy away from cards with annual fees. They can easily pay for themselves, many times over. Ross recommends the Chase Sapphire Preferred and the Capital One Venture X.
2x cash back can be worth 2-7x points when redeemed strategically. Only settle for cash back if you’re not interested in maximizing free travel.
Never book through the credit card portal — always transfer to partners first for maximum value.
Plan ahead and align big expenses with welcome bonuses to maximize points earning
Even casual travelers (1-2 trips per year) can cover most or all travel costs with these strategies.
Want to dive deeper? Grab Ross's free Points & Miles Cheat Sheet and follow him @itineraryboss.
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