This episode features Matt Senter, co-founder and CTO of Lolli, discussing his path from an early startup called Cosmic Cart to building a bitcoin rewards shopping platform. Senter recounts first hearing about bitcoin in 2013 through a contractor, initially dismissing it, then returning to cryptocurrency in 2016 after selling Cosmic Cart, experimenting with Ethereum smart contracts before fully committing to bitcoin. He explains how he and co-founder Alex Adelman built Lolli using retail relationships from their prior venture, designing the product for consumer accessibility rather than crypto enthusiasts. The conversation covers Lolli's technical evolution, from a Chrome extension to supporting withdrawals to wallets and cash, the philosophy of onboarding non-bitcoiners through familiar shopping habits, and why Lolli avoids maximalism toward technologies like Ethereum and Lightning. Senter also addresses skepticism about government bans on bitcoin, arguing confiscation is impractical given self-custody and seed phrases. The episode closes touching on international expansion challenges tied to retailer and regulatory complexity.
Lolli co-founder Matt Senter explains how shopping rewards quietly turn everyday spenders into bitcoin holders.
How did you first learn about bitcoin?
A contractor on my first startup, Cosmic Cart, brought it up around 2013 in Minneapolis and kept telling me to get into it. I kept asking questions but didn't really understand it at the time. We were in the middle of that startup and it wasn't bitcoin related, so I didn't pursue it until later.
What was Cosmic Cart and how does it relate to Lolli?
Cosmic Cart was a universal shopping cart and enterprise commerce gateway that let you buy a product anywhere you saw it, like a Target item on ShopStyle, by powering the pipes between retailers and publishers. It was more B2B enterprise work. Lolli is consumer facing, which I actually enjoy more since you interact directly with the community using your product.
What made you and Alex fully commit to building a bitcoin business?
I was playing with Ethereum smart contracts for a healthcare idea but couldn't see a path to monetization. Alex came back with the shopping rewards idea, which seemed like an easy way to get people into bitcoin using our existing retail relationships from Cosmic Cart. It made sense given our e-commerce background, so I abandoned Ethereum and joined the Lolli idea.
Why won't governments be able to shut down or confiscate bitcoin like they did with gold?
It's a distributed system, hard to stop short of something like an EMP taking out global electricity. If someone memorizes their seed phrase, there's no physical place to seize their bitcoin, and legally you can't be coerced to reveal private information like that. I think critics saying it'll never be allowed are either bitter they missed out or positioning themselves to get in later.
How do you view Ethereum after experimenting with it early on?
I try to avoid maximalism of any kind. Ethereum has value as a distributed computer, though I'm skeptical when people call ether money the way bitcoin is money. I haven't touched it since 2016 or 2017, so I don't know its current maturity, but I don't hate it like some bitcoiners do.
What approach did you take designing Lolli compared to other crypto rewards attempts?
We didn't approach it from the crypto side, we approached it from a consumer design standpoint. We looked at existing bitcoin and Ethereum apps and found the user experience horrible and inaccessible to non-technical people. Our focus was building a product for our siblings and parents who aren't crypto savvy, converting rewards to bitcoin on the back end rather than leading with the technology.
How does a first time user experience Lolli, and why would someone sign up without knowing bitcoin?
We capitalize on bull markets for marketing since bitcoin is already in the news. We tell easy stories, like early users effectively getting free goods since their rewards multiplied in value. Many users get their first ever bitcoin through us, then we educate them further, helping wean them off fiat over time once they're hooked.
What did the first version of the Lolli product look like technically?
We launched with Chrome and Safari extensions plus a website you could shop through directly. The extension showed a banner with your cash back percentage, redirected you to the retailer, and tracked your session so purchases got rewarded in bitcoin. Shortly after launch we had to quickly add the ability to transfer bitcoin off site since advanced crypto users wanted that option immediately.
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