‘The Points Guy’ Takes Stake In Credit Card Company

Brian Kelly started The Points Guy at just the right moment. At first he searched for a revenue model, selling premium memberships that included consultations with him and selling award booking services (he went by pitbrian on FlyerTalk and was the low cost provider of award booking services). But he hit on credit card affiliate commissions right as that was taking off.

The first big windfall came with a British Airways 100,000 Avios offer before that program massively devalued, when you could include multiple inline stopovers on a single award and premium cabin tickets were far less expensive.

He made the fortuitous decision to change affiliate link providers, and Bankrate wanted him back. They purchased the site a decade ago for a rumored low 8 figures. They staffed it up, while keeping Brian on in the role of CEO. Brian stayed with the company after their acquisition by RedVentures. And RedVentures even extended his contract five years ago, since readers still associated him with the site and assumed that much of what was created there was his doing even though they were up to around 120 employees.

The hockey stick in business success for that site really came in fall 2016, when Chase Sapphire Reserve was first launched – what was at the time a uniquely generous premium credit card paired with a 100,000 point bonus. “TPG” was given exclusivity in the affiliate space with the card launch. Other issuers took that card’s success to be in some measure the result of their favorable coverage, rather than the result of Chase spending way too much to acquire customers with a product that would never earn back the acquisition costs.

Brian no longer runs The Points Guy, but he’s stayed involved in miles and points as an investor. He was an early investor in Bilt Rewards, which has performed incredibly well. He wrote about traveling to the Bilt founder’s family home on Moskito Island a couple of years ago. Bilt was last valued at $1.5 billion, I believe the fastest startup to reach that valuation.

So it was interesting to see that Brian has invested in Cardless.

San Francisco-based financial technology firm, Cardless, Inc. today announced a new debt deal with i80 Group, securing a three-year $75 million credit facility. The deal is a warehouse facility that will enable Cardless to fund customer receivables, growth, and continue its work with large, globally recognized brands.

Concurrently, Cardless has announced that Brian Kelly, founder of The Points Guy has invested and will be an advisor to the company. Brian will join other Cardless angel investors and advisors that include founders of Netflix, Seat Geek, Bonobos, Plaid and more.

A Cardless co-founder was a TPG intern 7 years ago, so the relationship isn’t surprising. Still, this strikes me for two reasons.

  • A headline ‘The Points Guy takes stake in credit card company’ certainly turns the world on its head.

  • Cardless has been moving away from rich travel rewards. They work with niche brands to find customers and believes it can support smaller co-brands than big banks with a tech stack that makes this cheap to do. But LATAM aside they’ve largely been focusing away from rich travel rewards, with less costly retail and non-travel brands.

Brian has received a lot of flak from miles and points enthusiasts over the years. I’ve interpreted much of it as envy by people who consider themselves to know more about miles and travel than he does, but who haven’t monetized their knowledge (there are other criticisms as well). But Brian is hardly alone in making big bucks off of frequent travel. It’s just that people like, say, Hal Brierley don’t have the same profile with a mass audience that Brian has built. (Brierly led D Magazine‘s list of most generous philanthropists in Dallas a decade ago.)

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. He’s an unapproachable person who gives the impression he thinks he’s better than others. In the few times I’ve crossed his path he’s had a prima dona persona who couldn’t care less for the masses unless they inflate his ego or overall financial worth. Why attend a conference but refuse to have a conversation with anyone outside your entourage? Because it’s about image and self-indulgence, that’s why.

    Call it envy if you will. He’s just not someone I’d ever be eager to do business with, let alone know outside of work.

  2. Luck played a huge role in the success of The Points Guy, but there are other factors, such as branding. “The Points Guy” is instantaneously relatable. I won’t say it rolls off the tongue but it sure is more approachable than a lot of other sites like TRAVEL CODEX (lololol) where the author was so smug about his PhD that he booked airline tickets with the honorific of “Dr.” which is obviously meant to be for medical doctors.

    Chase spent a lot of money on Reserve customer acq but it had a halo effect on the brand perception of Chase’s entire card portfolio. So the unprofitability of Reserve itself must be viewed in juxtaposition with the profitability of Chase’s other cards.

    On the topic of monetization, the idea of monetizing something that is meant to be a hobby and to form a community of like minded people, does not sit well with many folks. I understand this blog started out as a more civic-minded place to share news and information of interest to frequent business travelers. Now the quest for ad revenue has debased the author into posting stuff like urinating on seats.

  3. My criticism of the original Points Guy and so many other bloggers is they’re essentially pimps or crack dealers peddling addictive products.

    The reality is most people signing up for these credit cards will never, ever achieve enough points or miles for the kind of bucket list aspirational trips that Kelly and others promote or used to promote.

    It certainly is not JOURNALISM even as TPG purports to be a news outlet.

  4. He’s doing a mini version of what celebs do with brands. Little cash investment on his part, they get to use his name. Not sure it turns ‘the world on its head’ but does get attention of travel media.

    Why not, little cash downside, remaining upside as long as he does the diligence and doesn’t end up in an FTX situation.

    Saw him on a flight just before the expose on his personal life came out, he was downing the cocktail on a short flight with a firm first.

  5. @UAGS

    LOL about the phd

    About Reserve, it probably underwhelmed their long term expectations. There was little follow on after that initial push for the card, vs say Amex that’s followed on with aggressive Plat offers in the last couple years.

  6. Geeze. I do not have a doctoral honorific.
    But you may call me Lord.
    And that still makes me an a**hole.
    Just because I bought a swamp in Scotland.
    Any real estate developers are free to call me.


  7. Never met him, so no personal insights, but given how enamored he seems to be of his lavish lifestyle, it’s amazing how boring and uninspired the website has become. It might as well be written by ChatGPT on tranquilizers. Seems no longer directed at points and miles enthusiasts but for folks who travel occasionally and want some generic guidance in one place rather than doing a few simple Web searches. Zero personality in most of the content, including the reviews. Much prefer Matthew, Lucky, and Gary who come across as smart, interesting people with an eclectic mix of content and a point of view. Affiliate links seem to get everyone’s dander up but there has to be a business model, and at least it’s transparent.

  8. The articles are flavorless with recycled information as if a chatbot wrote them long before anyone knew what a chatbot is. And they’re not interested in improving their writing staff either. Seems like you have to be a human drone to write for TPG.

  9. Despite his physical stature he’s a small guy who needs adulation. Most individuals who have achieved the wealth he obviously has live their lives far differently. He writes as if he’s better than anyone which to me is an obvious attempt to make up for his insecurities.

  10. The sad part was when Summer at MommyPoints went over. I don’t blame her decision, just the results.

  11. Ah yes the classic criticism of someone successful is out of jealously and envy. Another grade A take by Mr. TMZ.

  12. I encountered him couple of times years ago at these FFU events and can confirm that it seemed he was only interacting with his entourage and some schmoozers! Later on he shut down his blog’s comment section after commenters called him “corporate shill” for what I believe it was people accusing him of selling out and defending certain “loyalty” programs after horrid and successive devaluations.

  13. I think it’s great he was able to minimize his work. I wish more people were like Brian. Good for him.

  14. I gave up on TPG on the Marriott/SPG merger. That was a disaster, and there was zero accountability from the CEO at the time. One of TPG’s contributors wrote a piece about how the CEO “was out to lunch” about the impact on customers. It was relatively scathing, but it was also spot on about how long-standing SPG customers actually felt. Hours after the article was published, it was pulled and the contributor was let go… and no such piece ever returned to TPG despite all the other blogs having similar articles out at the time. TPG lost its integrity as a credible source overnight. It’s now just a marketing and sales site for credit cards. I don’t begrudge them that. But they should be upfront and honest about that instead of passing themselves off as a miles and reviews site.

  15. Interesting but not super surprising. My problem with TPG has always been that it’s ALL about the money under the guise of just being a points/miles advice blog. It likely wasn’t even started as a passion or hobby or to help others. It was to make money, period. I don’t know him so I won’t pass judgment beyond the business side. I was also disappointed that Mommy Points went over there. I was worried that Ed Pizza was headed that way but something seems to have stopped him but you can feel the power of the dark side pulling at him on his podcast at times (I’m sure he would smile at that comment). I’m sure it’s some of those personal relationships at TPG. I really don’t blame people for trying to make money and going over to TPG but it takes the personality out of it for sure. Gotta love capitalism, even people on Onlyfans make millions these days.

  16. @Kalboz – I remember he shut down comments when Mommy Points wrote a whiney article about a pro-Trump demonstration & got roasted for it.

  17. @UA GS @ SFO,

    The notion that “Dr. is obviously meant for medical doctors” is incorrect. it applies to Ph.D. holders as well. I’m not familiar with the other site you mention, so don’t have an opinion about the author. But the contention above is not correct. If just your opinion, you’re entitled to that, of course. But, as the statement of fact it appears to be, nope.


  18. TPG is polarizing and I agree they both over inflate point/mile values and blatantly shill card (athough the same could be said for many of the blogs). As you likely know Brian worked on Wall Street and made his money there. He retired and started TPG. It was sold, as noted and he did extremely well. That company was later acquired by Red Ventures (near where I live around the CLT area). They are fully corporate and, of course, will maximize revenue on the site. I have no doubt Brian is a self centered Ahole but frankly he has earned the right to be just that. He had a successful financial career then topped that with what he made on TPG.

    I subscribe to it and find a number of their articles entertaining and informative, I just skip the shilling of credit cards (like I do on OMAAT and VFTW) so see what information I may actually want to read that provides either information or interesting content (like review articles). Doesn’t cost anything so ignore it if you want – your choice.

  19. @AC – you are absolutely wrong. TPG/Brian worked in HR at Morgan Stanley. he was not a banker and did NOT make his money as a banker on Wall Street. While he was at Morgan Stanley he started getting into credit cards and giving people advice. One thing led to another. I’ve listened to a podcast he was on (Jumping off, I think?) where he talked about how he did this, and was very explicit that he was NOT a banker and was pretty poor when he worked at the wall Street firm – and that he made all his money through his site. Better re-check your knowledge.

  20. I started following TPG almost from the beginning. His daily newsletters were a source of reading enjoyment and useful info. I’ll be forever grateful to TPG for allowing me to get out from under AmEx and become a Chase Reserve person. To this day, I’ve not had a single problem with Chase. And of course, Brian IS a celebrity, not based on being a movie star spouting unwanted opinions, but based on what he’s accomplished … if that’s what he wants, why not? He’ll go down in history as one of the first huge success stories of online communication. People who criticize ‘celebrities’ for seeking attention and positive PR … and not wanting to be ‘their friend’ are hopelessly naive. I have great respect for Mr Kelly … based solely on his accomplishments. I don’t give a rip what he does in his spare time, it’s none of my business.

  21. I unsubscribed a few years ago…..now getting emails promoting this new thing.


  22. Re: “Joseph says: May 17, 2023 at 10:18 am I think it’s great he was able to minimize [sic] his work. I wish more people were like Brian. Good for him.” I hope that’s intentional and not a typo, made me smile, reminiscent of Emily Litella (Gilda Radner original 1970’s Saturday Night Live Not Ready for Prime Time Player)

    Commentary (among many others): “What’s all this fuss I hear… about an Eagle Rights Amendment?” (or “busting school children” or …)

    “The editorial was in favor of the Equal Rights Amendment. Not Eagle Rights – Equal Rights.”
    “Never mind!”

  23. I was a former BoardingArea blogger in early 2010s and knew Brian around that time. He always liked the finer things in life and his desire to become famous was probably what helped propel TPG into the mainstream. I don’t think people realize how much travel bloggers make (including Gary and Lucky). Back in 2010 when I was blogging and had affiliate links, Chase paid me between $100 (CSP) to $500 (Chase INK) per a signup! At the peak, I was making $30,000 a month and my blog was one of the smaller blogs.

    A few years ago I did a back-of-the-envelope calculation for TPG based on some comments Brian had made about how much traffic TPG website gets. If he converted just 0.25% of the total monthly TPG readers to sign up for a credit card that paid $100 commission, he is netting around $20,000,000 a year. My guess is that 0.25% conversion is low and it is probably closer to 3.0-5.0%, so easily $50-$100 million a year.

  24. I’ve met Brian twice, and he could not have been nicer. Once at a hotel when we just happened to be staying at the same place (on points) and another time at an event.

    I think just about any reasonable person would say that they wish they had the same level of success in their own profession as Brian has had in his.

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