Give me the elevator pitch on your company:

Splitzee is a social money company based on the idea that groups of people want to engage in commerce in a fundamentally different way than individuals – one with different transparency and accountability mechanisms. We’ve built a tool that solves a painful problem – every team captain will agree that nothing sucks more than asking your friends for money. Our tools let you accept payments from multiple sources, communicate with your team, issue payments and reimbursements, and track everything automatically. Think Eventbrite + Venmo + Square. Soon every softball team, girl scout troop, church group, and sorority will use Splitzee to manage their money.

Tell me a little bit about your background: what did you do previously?

I’ve been an entrepreneur since 1995 when I hung out a shingle for web development. Since then I’ve founded six different tech startups: two failed, two sold, and one went public in 2013 with a 1.2B market cap. Splitzee is my sixth. If being on a startup is like being on a roller coaster, I’m the guy who goes on a ride, throws up, and gets back in line to go again.

What does entrepreneurship mean to you? How did you first get involved?

My trajectory into entrepreneurship was a bit nonstandard – I originally wanted to be an actor, then a director, then a producer, and then I realized that creating businesses is as creative an endeavor as things come. Rather than write a script, assemble a cast, and direct your actors, you create a business plan, hire your team, and manage your employees. I went to Babson to get an MBA in order to gain the execution skills to make my creative startup visions come true. With six under my belt, I can testify to the fact that the endeavors are the same.

It may seem expansive, but I’ve come to see entrepreneurship as the essential profession of our generation. With technology moving at breakneck speed, only the entrepreneur is positioned to deliver the positive benefits of innovation to real people for real problems. Governments, colleges, NGOs – none are designed to *actually deliver* value in a practical way. Our problems – and opportunities – are getting larger every day; Entrepreneurs are the only people who can save the world.

Where/when did you have that aha! moment for envisioning Splitzee?

I played third base for my company softball team and know how grumbling over money issues at the pub afterward had a tendency to sour our playing experience and damage our friendships. As a father I’m constantly being asked to pool money for my kids teams, and I’ve seen how successful teams with resources and happy players can be.

Back in 2011 I started a company called Cauzoom, which was a cause-marketing platform for small businesses. We sold gift certificates to local businesses and redirected a portion of the proceeds back to local projects. It was during that business that I saw first-hand how to help groups *buy* things together. Given my technology and payments experience, I knew I could create a tool that would make the process easy and fun – not painful and tedious.

What is the pain point youre hoping to solve with Splitzee?

Every team captain will agree that nothing sucks more than asking your friends for money: juggling different forms of payment, keeping track, keeping everyone in the loop, not to mention all the social difficulties that arise from the process. Splitzee makes those pain points go away.

Why MassChallenge and what are your goals while being involved in the accelerator?

MassChallenge represents a unique opportunity to extend Splitzee’s expertise beyond our team’s current network and backgrounds. Startups are always better with a deep, diverse body of knowledge guiding them, and we’re hoping MC can help us build that out.

What is your greatest strength as an entrepreneur? Weakness?

I think my greatest strength is the same as my greatest weakness: I’m a generalist, with above-average skills in a variety of areas (coding, design, writing, planning, managing, selling, marketing). That’s very useful for a bootstrapping company, but means that I tend to take on tasks myself rather than finding people to execute them. As Splitzee’s team and resources grow I am increasingly (and happily!) looking forward to delegating work to people smarter than me.

What do you do to blow off steam when youre taking a break from changing the world?

My life comes down to this: 75% Splitzee, 20% family, 5% everything else. “Everything else” includes a little bit of softball, playing the ukulele (badly), and demonstrating my epic foosball skills to all comers.

Whats one quality that you think entrepreneurs need to have and why?

Stamina. Seth Godin calls the inevitable period between beginning an endeavor and having it pay off “The Dip.” Being able to stomach the cost – financial, emotional, social – of getting through The Dip requires determination and endurance. Too many entrepreneurs imagine that there will be no cost to their success, or that any cost will be low. Entrepreneurs need to quit early or not quit at all. It’s like a marathon: quitting at mile 2 frees you up to do something else; quitting at mile 21 means huge amounts of wasted effort.

The Startup Showcase is coming up. What excites you about the event?

Splitzee is both a compelling near-term startup and a Big Idea. I’m really looking forward to telling people how we’re building something truly important.