A motorcycle can promise freedom and still require an afternoon of paperwork. Before anyone gets to the open road, somebody behind a dealership desk has to find a lender, enter an application, wait for an answer, and perhaps start again somewhere else. Jason Guss built his company around that awkward interval between wanting something and being able to buy it.
The first version of his answer failed. Octane began as an aggregator, connecting powersports dealers with lenders. In Guss’s later account, the founders understood within roughly six weeks of launching that the model would not work. The problem was real. Their position in the transaction needed changing. So they made a considerably larger commitment: they would lend themselves.
That decision gives his career its shape. Guss, Octane’s co-founder and CEO, has spent the years since joining technology to the decidedly less forgiving business of credit. A software problem can sometimes wait for the next release. A loan remains on somebody’s books. The motorcycles supply the glamour; the repayment schedule supplies the plot.
Three questions before a business plan
Guss grew up in Palm Springs, California, and went east to Yale, where he studied political science and government, graduating in 2012. His undergraduate activities included the ski team. Long before powersports became his business, he was already spending time around a sport whose equipment and weather make an excellent case for having a financial plan.
At university, he and his roommates tried an options-trading venture, putting in savings from summer jobs and money from signing bonuses. It was an early attempt to turn an observation about markets into something they could own. After college, Guss joined Capital One’s corporate strategy group, working on problems across auto lending, retail banking, and brokerage.
The founders’ search for a business was unusually practical. They called people and asked about what frustrated them at work, where their industries wasted effort, and what they would pay someone to build. Those questions have a useful lack of romance. They require another person to describe a problem before the entrepreneur gets attached to a solution.
The lending process at powersports dealerships supplied one. Customers needed financing for motorcycles, all-terrain vehicles, snowmobiles, and personal watercraft. Dealers faced separate lender portals and repeated applications. Guss left Capital One and moved to Seattle to work with his future co-founders. Octane was founded in 2014. The opportunity lay in a transaction that already existed, with all its irritation intact.
The expensive part of changing your mind
Aggregating lenders sounded like a reasonable way to improve that transaction. It also left the company dependent on other institutions to supply the credit. Becoming a lender meant taking on underwriting, funding, processing, and servicing responsibilities. Each additional responsibility widened the distance between a clever interface and a business that could deliver the entire purchase.
Octane launched its in-house lender, Roadrunner Financial, in 2016. That date matters: the software company and the lending operation did not arrive fully assembled on the same afternoon. There was a period of learning, reversal, and construction. The neatness belongs to the retrospective. At the time, the founders were changing what they had to know how to do.
Guss’s later explanation of the opportunity remained tied to the merchant. A dealership needs a customer to complete a purchase, which makes it a useful place to learn what obstructs one. Manufacturers have a similar interest in removing obstacles. The people selling the vehicles can supply both distribution and a running account of what the financing system gets wrong.
By 2022, Octane’s expansion included outdoor power equipment, golf carts, tractors, and trailers, alongside partnerships such as Polaris. The categories look miscellaneous until you consider the counter: substantial purchases, specialist dealers, and customers who may need credit. Guss was following the financing problem across showrooms. The machines could change while much of the work behind the sale remained familiar.
A bridge loan is a leadership story
One of the revealing episodes involves neither an app launch nor a venture-capital celebration. In 2018, Octane needed additional capital to keep funding its growth without immediately returning for another equity round. Guss connected with Billy Libby at Upper90 through Nick Huber at Ribbit Capital. Upper90 supplied a six-month bridge loan.
The difficulty was a consequence of making loans: growing originations required capital alongside the borrowing available from warehouse lenders. Sales momentum could therefore create a funding constraint. For a founder, this is a rather pointed lesson in arithmetic. Doing more business can make tomorrow’s financing conversation more urgent.
Upper90 subsequently provided a $35.5 million senior secured loan and participated in equity rounds. The relationship illustrates how Guss’s job widened after the pivot. He had to persuade institutions to support the machinery behind the lending. A good customer experience required dependable access to money as well as dependable software.
In 2024, Guss publicly thanked outgoing chief risk officer Ray Duggins for his mentorship and the influence he had on Octane’s leaders. That acknowledgment adds another dimension to the founder story. The young entrepreneur who spotted an inefficient process also needed people who had spent decades working with the consequences of lending decisions.
Let the customer set the pace
Guss’s description of product progress is refreshingly concrete. In an August 2025 conversation, he said manual requirements had fallen from every application roughly five years earlier to about one in ten. Even where verification documents remained necessary, much of their processing had become automated. Those were his figures for that point in time, rather than a promise about every future application.
The goal was to let customers and dealership staff move without waiting for Octane. That is a useful product standard because it is measurable in somebody else’s day. Re-entering information and uploading documents are small tasks individually. Put them in the middle of a purchase and they become everyone’s business.
His public advice to other founders carries a similar preference for focus. He advocates straightforward financing terms and has described shifting board meetings toward discussion of difficult business questions, with routine reporting read beforehand. There is a recognizable managerial instinct here: use the meeting for the work that needs a conversation.
“you can do it your own flavor.”Jason Guss, on building a company’s operating culture
He has also argued that successful companies can be run in very different ways. Borrowing somebody else’s management habits wholesale is optional. That outlook sits comfortably beside a business whose central decision was to alter its own model when the first one proved inadequate. Consistency of purpose can require considerable inconsistency in the original plan.
Two billion dollars, carefully counted
The public milestones grew substantial. Forbes included Guss in its 2018 finance 30 Under 30 list. He received a gold award for entrepreneurship at the 2023 American Business Awards and was an EY Entrepreneur Of The Year New York finalist in 2024. These are distinct recognitions; the finalist designation deserves its proper name.
In December 2025, Octane announced a $100 million Series F led by Valar Ventures. The transaction valued the company at $1.3 billion and split evenly between primary financing and secondary share sales. Some of the money therefore supported existing shareholders’ liquidity. The headline amount was larger than the sum of fresh capital going into the business.
For the full year 2025, Octane reported $2.1 billion in originations, a 29 percent increase over the previous year, and cumulative originations exceeding $7.6 billion. These figures describe loans made through the business. They give the early pivot a scale that the founders could hardly have demonstrated during those first weeks.
Guss’s next ambition extends the logic further. Octane’s Captive-as-a-Service offering lets a manufacturer or dealership use its own brand on financing supported by Octane’s infrastructure. In January 2026, the company brought that offering into auto dealerships. In September, it announced Forest River Finance Powered by Octane for the RV market.
On October 6, 2026, Octane announced a $1.4 billion forward-flow facility with institutional investors including New York Life and MetLife Investment Management. Such an arrangement provides a route for loans to be purchased over time. It belongs to the funding architecture that keeps the customer-facing system moving. The showroom is only the visible end of a longer chain.
A walk without a financing application
There is a quieter New York detail in Guss’s account of himself. He likes walking through the West Village and stopping at restaurants, with the neighborhood’s architecture and food among his favorite things about the city. It is a pleasing counterweight to a working life spent measuring purchase friction: a walk whose value includes the detours.
His professional story began by asking other people where their work became unnecessarily difficult. The answer took him from dealer software into lending, then toward supplying financial infrastructure under other companies’ names. The purchases have grown more varied and the funding more elaborate. The original test remains easy to understand: when someone is ready to buy, how much waiting can Guss remove?