“You’ve been the founder of how many companies?” I asked.

“You know, I was thinking about that before this—technically it was six.”

That’s how I knew we were in for a good discussion.

I’ve known Christopher Day, or “Toph” as he likes to be called, for over a year now but I still learn something new and impressive about him each time we hang out.

His life growing up in a dirt-floor house in rural Indiana made Toph sure of one thing: his career path was going to be nothing like his childhood. And while his first career move was from slopping hogs to putting trash in a dumpster, it wasn’t long before he saw his window of opportunity—entrepreneurship.

As I sat with Toph onstage at the last Verge event, I couldn’t help but chuckle at his childhood dream of one day owning a Chevy Blazer and a bag phone (like his boss at his dumpster job). True to a youngest-child mentality, Toph is a joke maker as well as a risk taker. He recounts his early evolution in the first part of our talk:

From slopping hogs to serial entrepreneurship.

It was necessity that pushed Toph over that entrepreneurial edge. With his brother, he started a painting company to pay his way through college. It was far from the glamorous depictions of business ownership that you often see on TV and the big screen.

Toph up at 6 AM each morning and hustled their way through to their graduation from Purdue University. Despite all the effort, there was still a gap between where he was financially and where he wanted to be.

“When I was 25, I had a negative net worth,” he recalled.

It was in that year of 1997 that Toph launched StarCom Broadband. It was a cutting edge telecom business that was the first private company to leap over some of the technical hurdles that had stifled the industry for so long.

It was in capitalizing on this opportunity that Toph proactively went about building a valuable asset—a loyal list of subscribers—which eventually led to a lucrative sale of the company in 2001.

Here’s the story (in his own words) of how he ended up starting StarCom, which sold within 10 days of the initial offer:

After Starting Up: You’re not in Buck Creek slopping hogs anymore, Toph.

After a few more impressive companies and exits, Christopher Day has moved to focus a lot of his energy to the funding side of the equation as an investment banker.

With his investment banking firm, Navidar, Toph helps mentor entrepreneurs, executives, board members, and investors navigate through fund raises with even the most complex deal issues.

Having known Toph for a while now, It makes sense.

He’s really passionate about improving the investment banking infrastructure in the middle quarter of the United States, especially when it comes to technology companies. He’s seen billions of dollars exported outside his home state of Indiana. But Toph is looking for a better way and hopes to help create centralized pools of substantial capital for startups in the growth stage of the business lifecycle.

“That’s where wealth is created,” Toph says.

He’s dead serious about creating a better investment environment for entrepreneurs in the Midwest. It’s why he and his partners founded Navidar and why he is so passionate in the last few minutes of his talk:

More on fund raising:

We had some fantastic questions and answers in our fireside chat that evening. Toph obviously has developed killer entrepreneurial instincts through starting and exiting six companies.

What questions do you have for serial entrepreneurs and investment bankers like Toph?