Co-Founder @withautopilot | Financial Optimizer Points Millionaire

Joined September 2020
37 Photos and videos
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This is EXACTLY why we built @withautopilot - to help consumers get the money they're owed. It works on all major US carriers and hotel brands. It's free until we save you money (then just 25% of the savings). Sign up at withautopilot.com
"The airlines are using AI to get as much money out of us," says @thepointsguy Brian Kelly. "We should be using AI tools to get back at them." cnb.cx/432T4s0
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Ended up on the @British_Airways wrapped Subway this morning!
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Now is a great time to remind people: Spirit going out of business has a tremendous impact on fares. Fare data from @withautopilot: prices are up >21% in the last 7 days. Not all of the increase is due to Spirit (oil, etc), but this is not a good sign for things to come.
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Haiku in memory of Spirit airlines: Yellow A320, Spirit folds its tray table, Final boarding call.
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Hot take: airplane wifi shouldn't be free. Speeds on Viasat-equipped planes have become so much slower now that bandwidth is taken up by kids scrolling TikTok. I'd happily pay for dedicated bandwidth/faster speeds. This isn't the case with Starlink tho.
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This is how airlines are quietly bringing back change fees. For 6 years, free changes were normalized. Now Delta and United are introducing 'Basic' tiers that re-normalize fees. The smart play: raise current prices to Basic, raise Standard and Flex higher. You're paying more for what used to be included.
.@united is rolling out new "basic" premium economy and Polaris Biz Class fares. The new fare structure will give flyers booking more expensive standard or flexible fares access to the Polaris Lounge. Basic fares will be nonfundable, nonchangable, and nonupgradable.
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United launched a new product that no other US airline can copy. @FlyAirNZ patented the Skycouch in 2010. United now has exclusive North American rights. Competitors can't copy it, but they can engineer around the patent, giving United a nice head start.
The entire row is alllllll yours. Welcome to United Relax Row, three adjacent United Economy seats with adjustable leg rests that can each be raised or lowered to create a cozy lie-flat space for stretching out... You'll also get a mattress pad, blanket and two pillows. If you’re traveling with kids, a plushie too! United Relax Row will be available starting next year on more than 200 of our 787s and 777s, each with up to 12 of these brand-new rows. united.com/Elevated
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This is crazy, just over 10,000 extra @JetBlue points to fly JAL Economy -> Business on a 14-hour flight... well worth the upgrade
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SFO TSA isn’t actually run by the government. They’re private contractors (so they still get paid during the shutdown). Thus, almost no lines, and big smiles from the security agents here this morning.
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TIL @JetBlue JFK Terminal 5 DOES have a Priority Pass lounge. Across from gate 507 is Gameway. Incl. is 1 free snack, a N.A. beverage, and an hour of gameplay. The bottle of water and snack alone saved me $15 instead of buying in the terminal.
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Sam Hollander retweeted
13 Oct 2025
First heard about @withautopilot from @pitdesi’s post below and signed up immediately. It’s awesome. I’ve saved over $750 to date with effectively zero work involved.
14 Jan 2025
Cool product! I signed up a few months ago when diligencing it, then forgot about it. It has saved me ~$2,000 on flights already! Called Autopilot (link below) - you link your inbox, it tracks your flights & gets you credit when the price drops. They charge 25% of savings.
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Let’s see if Hold Assist in iOS 26 works for calling airlines. Trying to book an @AlaskaAir partner award. It’s erroring out online (probably phantom space) but I want to call in to see if they can book it manually. Current hold time: 4 hrs and 26 minutes.
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It even shows the transcript of the credit card sales pitch
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If we can get rewards points or cash back on stablecoins, I think it’ll be a no brainer. Even though transaction costs will be lower, it’ll be a tough pill to swallow for consumers to lose points/cash back. Show me the incentive and I’ll show you the outcome.
17 Sep 2025
I made a bet about credit card usage. Today, >50% of American adults use a credit card every month. @BoredElonMusk thinks that number will be <25% in 5 years, replaced by stablecoin rails. I don't see it. Whose side are you on?
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My friend got scammed at airport currency exchange. He got a fake $20 bill. His bank caught it when he tried to deposit. LESSON: Let YOUR bank handle ALL foreign money stuff. Pay in LOCAL currency and let your bank convert. Never let merchants convert to USD for you.
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The most UNDERRATED credit card right now is the new Alaska Airlines Summit Visa card. It comes with a 100k Alaska miles welcome offer. And gets you 3x points on ALL foreign transactions. If you travel, you *need* to get this card.
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Everyone knows that airlines use your browsing activity to bump prices up. Surprisingly, that’s actually not true! An analysis of 1.5 million flight prices shows airlines don’t raise fares based on your search history. Here’s what’s really happening: 👇
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So why do people think airlines track them? Simple: You check at 9:50am ($200), then again at 10:10am ($300). You think they're targeting YOU, but really, the lower priced inventory just sold out or they raised the price at 10am.
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Follow @SamHollander_ for more hacks to save money on travel!
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