Why did Dan Cholewinski decide to leave corporate employment and start his own business?
After joining the senior management team of a motor finance lending business — where he had spent 15 years building his career — Dan Cholewinski found that his day-to-day work had shifted almost entirely toward meetings about policies, procedures, and regulation. Missing the direct connection with people that had defined most of his professional life, he questioned whether that environment was right for the next 25 to 30 years and decided to find something that would genuinely "light a fire" under him. The answer was co-founding Vast Commercial Finance with a colleague from the same business.
The contrast with Cholewinski's earlier years at the company is striking. When he joined that motor finance lender at 21, it employed around 65 to 70 people; by the time he left, headcount had grown to roughly 600. For the better part of those 15 years, his roles — from first salesperson in a national accounts division at 23, to leading a field sales team at 26 — kept him in close, daily contact with clients and the commercial realities of the business. Reaching senior management changed that dynamic completely, and it was a change he found difficult to accept long-term.
Vast Commercial Finance has now been trading for 4.5 years. That entrepreneurial leap, Cholewinski explains, was ultimately about reclaiming the hands-on, people-first approach to sales and relationship-building that had always driven him. You can hear the full conversation on The Purpose People Podcast on Listenly.
"If I feel I'm not making enough sales, it's because I'm not talking to enough strangers — as simple as that. Being sat behind the desk being really good at something isn't gonna bring you a whole load of sales."
— Dan Cholewinski, Co-founder, Vast Commercial FinanceAbout Dan Cholewinski
Dan Cholewinski entered financial services at 18 with no university degree, starting in data administration before rapidly progressing through underwriting and telesales. By 21 he was in a field business development role at a growing motor finance lender; by 23 he had become its first salesperson in a newly formed national accounts division targeting the top 100 UK motor dealer groups. At 26, he stepped into his first leadership position, managing a field sales team — a role that cemented his reputation as someone who builds commercial relationships through direct, consistent human contact.
Over 15 years at that single employer, Cholewinski watched the business scale from roughly 65–70 employees to around 600. It was precisely that institutional knowledge — understanding how a lending business grows, where it stalls, and what clients actually need from a finance partner — that gave him the conviction to co-found Vast Commercial Finance. His voice on business funding and commercial finance carries the weight of someone who has lived every stage of that journey, from first cold call to the boardroom, and chose to start over by choice.
See also
Dan moved from data administration at 18, to underwriting at 19, telesales at 20, and field business development at 21. At 23 he became the first salesperson in a national accounts division targeting the top 100 UK motor dealer groups, and took on his first leadership role managing a field sales team at 26.
Dan Cholewinski started working in financial services at age 18, joining a finance lender in a data administration role without attending university. He progressed through underwriting and telesales before moving into field sales and eventually senior management.