Christopher Day has officially transitioned his role at Navidar Group to an advisory capacity — the investment banking firm he started with his brother five years ago — and he's itching to pick up where he left off, as one of Indy's prolific and effective serial entrepreneurs.

"I really didn't mean to but I became a serial entrepreneur in technology," Christopher said. "I was planning on taking some time off after starting, growing and selling companies to Comcast, Motorola and others, but that didn't happen the way I expected either because we (Christopher and his brother, Shephen) formed Navidar and I was suddenly in the investment banking business. I'm looking forward to getting back to my roots and I've got a few ideas; I'm looking forward to building another business in the exciting vertical of technology."

So much has happened in the Indy startup and tech scenes over the past five years, that many people might not be aware of Christopher's CV outside of investment banking. He made some local headlines when Navidar served as the exclusive investment baking advisor to iGoDigital when they were acquired by ExactTarget, and his analysis of the ExactTarget sale to Salesforce was one of the most popular pieces to ever grace the digital pages of this blog, but Christopher's role in national and international deals have been largely behind the scenes since 2009 — his roles as chairman of and a TechPoint board member notwithstanding.

As one of the Indianapolis Business Journal's 40 Under 40 honorees for 2012, the IBJ summarized his story:

Christopher Day's story is almost a tale of two lives.

Growing up outside of Lafayette as the youngest of five children, Day and his siblings didn't have much. "We were as poor as dirt," is how Day, now managing partner at Navidar Group, remembers it.

Dirt, in fact, is what made up the floor of their Buck Creek farmhouse.

In his German Baptist upbringing, which Day describes as "Amish with wheels," the Day children were expected to work hard on the farm and figure out a way to pay for college.

For Day and his older brother to afford tuition, they started a house-painting company in the suburbs of Chicago. While at Purdue University, Day developed a keen interest in the construction industry, and obtained his undergraduate degree in construction management in 1992.

Following an internship with locally based Wurster Construction, Day got his first real taste of the industry as a project manager for an Atlanta firm. He worked on hospitals and jobs related to the 1996 Olympic Games before he had a revelation. "When I learned what the net margin was in that business I determined I didn't want to be a general contractor," he said.

But the business experience was invaluable, and Day had long since said goodbye to dirt floors and manual labor.

Over the next several years he started and sold several companies in telecommunications, real estate development and energy. From 2002 to 2008, he ran Indianapolis-based ViaStar Energy Inc., a provider of utility billing, meter installation and maintenance services to multifamily and retail properties. Motorola Inc. bought ViaStar in 2008.

Day also formed Indianapolis-based Caldera Development LLC, AquaStar LLC and StarCom Broadband, which he sold to Time Warner and Insight Communications in 2001.

Excerpt from IBJ 40 Under 40 article.

What's next for Christopher Day? What are you looking forward to doing in today's Indy startup and tech scene?

"If I think back to when I started my first technology company in 1997 and fast forward to 2014 — 'My goodness, am I getting old?' — when I look at the speed at which technology develops today and the traction that you can get in standing up a solution and going to market at a fraction of the cost compared to what it was 17 years ago, it's absolutely incredible. I find that extremely compelling and exciting, not to mention the new markets. What tech meant 17 years ago is totally different from what tech means today. Back then we hardly knew what to do with the Internet — not that it's necessarily all about the Internet — but it is definitely a driver. The other piece I find extremely compelling is recurring revenue businesses. That's what I want to build. I want to go back to building recurring revenue businesses like I did with ViaStar Energy and StarCom Broadband."

Where do you see yourself in one year? How about five years? 

"My goal in the next year would be to have identified which specific opportunity I'm going to pursue. The goal in five years would be part of the story driving our tech community with what I end up pursuing.  Really helping to propel the tech ecosystem forward, which helps propel our entire economy forward.  The tech sector here is vital to our future. If you look at the difference between just the last two years and the last 16 — the growth is exponential and it is only going to get better and better.  I'm really looking forward to being part of that story."

Common advice from veteran entrepreneurs is that if you are a technical founder go find a savvy business guy to partner with, and if you are a great business guy but not a details guy, go find an accountant with an entrepreneurial itch or a technical partner or both — go find your opposite.  What is it that you bring to the table and what is it you would be looking for in a partner or partners?

"So, all the personality tests I've taken over the years tell me that I fall into that leadership and vision capacity. I am going to start looking for people who have deep expertise in product development.

"A lot of people have said to me that they wondered how long it would take for me to come back into the entrepreneurial technology community. People told me they figured it would be sooner or later and they seem to be excited to hear it, so we'll see where that leads. It's been a blast the last five years. At Navidar we've done deals all over the world and it's been fun to sit on the other side of the table as an investment banker. I think leveraging the things I've learned over the last five years on the investment banking side of the table will help me be even more effective with the next business. I'm looking forward to putting that knowledge to work as well."