“It's finding the founder, and the team, where you get the feeling, you want to quit your job and go work there,” Jason Caplain said.

The Bull City Venture’s co-founder’s venture capital legacy isn't just about deals; it's a story grounded in purpose. With investments in companies like ChannelAdvisor and WeddingWire, Jason reflects on the responsibility he holds to his limited partners, the founders he invests in, and the community at large on the latest episode of Founder Shares.

"There's people that trusted us with our hard-earned dollars to provide a great return, and there's a lot of belief in us, so we've got to fulfill that," said Jason.

His entrepreneurial spirit was passed down to him from his grandfathers, who both were founders themselves, and he started his career as an investment banker investing in other people’s dreams.

“But I always thought, ‘Hey, it'd be good to find a shortcut to raise capital faster for these great companies,’” Jason said.

That’s when Bull City Ventures was born, and they began investing in technology and life science companies. But the firm is about more than just money. 

“We think our reputation is earned by all the help that we provide the companies afterwards,” Jason said.

The firm focuses on supporting entrepreneurs in starting, operating, funding, and exiting their ventures. At the heart of their strategy, it’s all about the people, and they focus on founders who inspire, recruit well, and navigate the intricacies of fundraising.

“In this business, you make money by having a belief that others don't necessarily believe in," Jason said.

Of course, venture capitalism isn’t all triumphs, and Jason’s had his fair share of setbacks, and even companies that have all the accolades aren’t guaranteed to succeed. Still, every venture, whether deemed successful or not, contributes to the collective learning journey and builds relationships that might lead to successful ventures to come.

“Start building the relationships when you don't need the capital,” Jason said. “You have to have friends. You have to have partners that you trust.”

It’s clear that venture capital is a collaborative landscape, and Jason emphasized the importance of aligning not just with founders, but with investors who share the vision and values of the company. With transparent communication and a genuine partnership approach, Bull City views investors not merely as financial backers but as strategic allies invested in the long-term success of the venture.

“Stay in touch with potential investors, have those conversations, stay on people's radars,” Jason said. “Because you never know when metrics might change or when something else has changed within the company that makes it more interesting.”

To hear the rest of Jason Caplain's personal and professional journey, make sure to tune in to the latest episode of the Founder Shares podcast, available wherever you like to listen. It's not just a podcast; it's a personal conversation with the individuals shaping the world of entrepreneurship.