Co-Founder @withautopilot | Financial Optimizer + Points Millionaire

New York, USA
Joined September 2020
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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Does anyone know if there's a way to ticket @AlaskaAir AS 65 (northbound Milk Run) on one day on one reservation? It looks like I'll have to split it up.
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Sam Hollander retweeted
Fun fact: I put all my family’s flights into my Autopilot account and surprise them with credits all the time. Used to take me hours each week to go through a long spreadsheet. Now it’s automated.
I just saved $1,200 on my flight using @withautopilot. This app is literally free money. Put in your flights and get $ back. @SamHollander_ was my roommate. I watched him start from nothing and build this into a huge biz, saving ppl thousands a day. Not using this is stupid.
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I've been the 'travel friend' for as long as I can remember. I built @withautopilot 3 years ago to save money on my own flights. It feels incredible to put money back in our customers' pockets. You're LOSING MONEY if you don't travel @withautopilot
I just saved $1,200 on my flight using @withautopilot. This app is literally free money. Put in your flights and get $ back. @SamHollander_ was my roommate. I watched him start from nothing and build this into a huge biz, saving ppl thousands a day. Not using this is stupid.
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Sam Hollander retweeted
I just saved $1,200 on my flight using @withautopilot. This app is literally free money. Put in your flights and get $ back. @SamHollander_ was my roommate. I watched him start from nothing and build this into a huge biz, saving ppl thousands a day. Not using this is stupid.
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It's like an inverse pricing chart @VirginAtlantic
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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
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.
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.
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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