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.)