August-September 2015

Cover Story

High Stakes

Jim Olson doesn’t gamble, although he’s president of a company that markets to online gamers, known to be fanatics. “I don’t like losing money I guess,” he says with a laugh. He joined Fourcubed in March to execute an ambitious acquisition strategy for the 10-year-old Minneapolis firm founded by Chris Carlson–a former stockbroker turned poker […] Continue reading →

Letter From the Editor

yin and yang

Dan Moshe, the founder of Tech Guru, and Jim Olson, president of Fourcubed, plan to get a beer one day soon and discuss a common circumstance at fast-growing companies—how to transition from the exciting yet unsustainable founder-driven years to professional management. The two met at the recent Upsize Growth Challenge workshop, where Olson is one […] Continue reading →


workshop: Upsize Growth Challenge

The Upsize Growth Challenge, presented by Winthrop & Weinstine, is a contest created by Upsize magazine to match two winning business owners with the expert advice they need to reach their goals. From nominations, judges select two winners based on the ambition of the growth goal and the quality of the work already completed to […] Continue reading →

Business Builders


The implementation of the Affordable Care Act has caused many employers to rethink the structure and type of health benefits they provide. In an effort to create incentives for employees to make smart health decisions while also keeping costs down, organizations are taking a closer look at the options available through consumer-driven health plans like […] Continue reading →


Consider this tale of two business owners. One is a talented architect who was wearing too many hats in his business and charging too little for his services. The other is a successful manufacturer with good cash flow and profits, but experiencing talent and operational issues that could cause his revenue to flat-line a few […] Continue reading →


The federal Americans with Disabilities Act recently celebrated its 25th anniversary. The Minnesota counterpart, the Minnesota Human Rights Act is older yet, having outlawed discrimination on the basis of disability since 1973.  With such a long history, it would seem that compliance with these anti-discrimination laws would be old news. However, Minnesota small businesses are […] Continue reading →


Can you imagine standing on a random street corner waiting for a stranger to walk by so you could stop him or her to propose marriage? Ludicrous? Absolutely, yet it’s an apt metaphor for how many businesses approach potential customers and their website. It takes time and effort to think through the fundamentals up front: […] Continue reading →