Stephen Seibel bought a one-way ticket to Halifax to start a car business. It is a pleasingly literal beginning for a company whose product must eventually leave the screen and arrive somewhere else. You can browse a sedan online. You cannot download it into your driveway, however accommodating your internet provider may be.
Clutch was founded in 2016 and began operating in Halifax in 2017. Seibel had come out of investment banking and marketing. He was entering an industry with vehicles to finance, customers to reassure and rules to navigate. The ticket took him to a place where the idea could become an operating business. Everything after that required rather more than a good booking.
Today, Seibel is Clutch’s Founder & President, based in Toronto. The route between those two points runs through an early customer in Cape Breton, an expansion into the Greater Toronto Area, a leadership partnership with Dan Park and a substantial amount of work on actual cars. The useful question is how a founder makes a complicated purchase feel simple without losing sight of the complications.
A ticket to Halifax
Halifax offered practical advantages. Startup costs were lower and the market had less competition. For Seibel and co-founders Andrew Dolinski and Chris Dolinski, those conditions helped make an early operation possible. A smaller market could give a new service room to establish itself before taking on a larger one.
The launch proposition addressed an ordinary irritation: the prospect of buying a used car could feel like an afternoon volunteered to someone else’s sales process. Clutch offered online browsing and test drives delivered to the customer. The buyer’s driveway became a place to consider the purchase, rather than merely the place where the purchase would eventually be parked.
Moving the meeting changed its setting and, potentially, its balance. The customer could start with information on a screen and encounter the vehicle on familiar ground. It was a concrete way to approach convenience. The company still had to arrange the journey, keep appointments and provide a car worth considering. An easier afternoon for the buyer meant more coordination behind the scenes.
Before the cars, other things to sell
Seibel is originally from Ottawa. He studied at Babson College from 2010 to 2014, graduating cum laude with a BSc in Business Administration. His subsequent work at Moelis & Company in New York involved mergers and acquisitions, with exposure to technology, media, telecom and utilities. Finance put him close to the machinery of businesses before he built one around machinery of a different kind.
He also had a more hands-on entrepreneurial education. At college, he led Presenter Pen, a student-run company of 30 people. It sold branded promotional goods and secured debt financing from the college. His account of the business includes designing and engineering new injection-moulded promotional products. Even in a student venture, there were things to manufacture, customers to find and money to arrange.
At Camber Media, where he became a partner in 2015, the work included retainer marketing and original content. A project credit lists him as producer of Right to Play - Dollo Ado, made with Camber Media as a production partner. The project involved a team travelling from Toronto to eastern Ethiopia in September 2016. Seibel’s pre-Clutch career had already moved between financial analysis, selling and making something tangible.
The driveway becomes the showroom
The interest in cars preceded the retailer. Seibel had worked as a performance driving coach and was a longtime car enthusiast. Clutch’s origin also had a consumer’s complaint at its centre: an unpleasant experience trying to buy a car with his wife. Someone who liked cars had found the transaction considerably less enjoyable than the object being purchased.
That distinction matters. Enjoying the product does not oblige a buyer to enjoy haggling, paperwork or an uncertain price. A business can inherit the appeal of the thing it sells while making the act of buying it unnecessarily taxing. Seibel set out to work on that second experience.
The first sale arrived in 2017. Barry, from Cape Breton, had read about Clutch in a blog post while looking for a first car for his daughter. Seibel delivered the car himself. He later recalled the family’s excitement and identified that sale as a major milestone. Before the bigger numbers, one family had agreed to buy through a new company and let it bring the car to them.
In February 2020, Clutch introduced its online buying experience to the Greater Toronto Area. Seibel welcomed the move after the company’s experience in Eastern Canada. A service developed around a Halifax launch now had to work across a different market. The familiar promise of convenience would need to survive more customers, more vehicles and more journeys.
The work behind the screen
A used car resists the neatness of a digital catalogue. It has an individual history and an individual condition. Two examples of the same model can require different work before they are ready for another owner. Clutch’s operation purchases vehicles from consumers, prepares them and offers them for resale. The chain connects someone selling a car with someone who needs one.
In his March 2025 interview, Seibel discussed machine learning for car offers and inventory management, alongside the logistics of moving vehicles. Those subjects belong together. A price is a decision about an object the company must handle. Inventory management reaches beyond a count on a dashboard into space, timing and the work each vehicle needs.
Here the customer’s experience depends on a sequence of less visible jobs. The attractive listing is useful only if the car has been assessed, the description holds up and the handoff works. A business selling physical inventory gets repeated opportunities to discover where its process is weak. Each vehicle supplies another example.
Two leaders, one difficult business
Dan Park joined as CEO in 2019, bringing experience in venture capital and at Uber. Seibel’s founder story became a partnership story. By July 2026, the two were appearing together on Between Two Brunettes, discussing the relationship between a founder and an operator, difficult decisions and Clutch’s return to profitability.
The distinction between starting a business and running an expanding one becomes particularly concrete in automotive retail. A company can have customers who want its service and still face demanding questions about capital and execution. Demand does not inspect a car, pay for inventory or organise the people needed to deliver it.
Clutch’s 2025 financing announcement acknowledged the evaporation of growth capital and the volatility the team had worked through. It also reported profitability in 2024. These are company milestones, achieved by an organisation rather than a solitary founder. Seibel’s place in that organisation includes building alongside a CEO whose job is to help carry the idea through its daily demands.
“I just grind, and I love winning.”
Stephen Seibel, March 2025
His description of himself is brisk enough to fit on a workshop wall. In a business with so many moving parts, the grind has a fairly literal interpretation. The same broad promise has to be fulfilled repeatedly, by different people, for vehicles that are never quite identical.
A bigger building and a longer road
In February 2025, Clutch announced more than C$50 million in Series D financing. Altos Ventures led the round, with new investors Industry Ventures and BMO Capital Partners and returning investors including Flight Deck Capital and FJ Labs. Planned uses included geographic expansion, reconditioning facilities and more inventory. Funding was being assigned to the physical capacity behind the online service.
The following month brought a visible example. Clutch’s flagship inspection and reconditioning facility officially opened in Mississauga on March 26. Its announced footprint was 111,000 square feet on 19.7 acres. It was built to prepare vehicles purchased from consumers before resale. Those dimensions give a useful sense of what a digital car business looks like when viewed from the ground.
Inspection and reconditioning space behind the online buying experience.
There is room for a little playfulness in the operation, too. When Clutch announced its NBA collaboration in 2023, a red flatbed truck became a mobile basketball court for a Toronto fan activation. A delivery vehicle had acquired a second occupation. It was an apt prop for a company trying to make its name familiar beyond the transaction itself.
Back where it began
In July 2026, Halifax entered the story again. Clutch announced a new customer hub there, with pickup and drop-off facilities, staff assistance and computers for guided digital shopping. The 11,000-square-foot hub gave customers another way to interact with the company in the city where its operating journey had started.
Seibel described the hubs as a complement to the digital experience. That is a revealing destination for the one-way ticket. The business has continued to put people and places around the screen: somewhere to ask a question, somewhere to hand over a vehicle, someone responsible for making the transaction work.
A car eventually has to meet its next owner. Seibel’s career has become an extended attempt to make that meeting easier. The website can start the journey. The rest of the business has to get there.