Successful Entrepreneur Sees “Holes in the Cheese” and Builds Great Companies to Fill Them

What is it that makes entrepreneurs different? The personal traits that enable them to look at things in ways most of us miss? For explanation, I love the way serial entrepreneur Kim Shepherd described it in our recent interview: entrepreneurs see “the holes in the cheese,” not the cheese itself. She added: “If men think things through, women feel things through.” 

Since we buy with emotion and justify with logic, it is the power of emotions in building businesses, particularly by women, that interests me. In fact, I recently wrote an article on the subject for The Huffington Post, which you can read here

Successful business-builders tend to share some common traits

What I am finding in my series of interviews with successful women entrepreneurs is that CEOs of startup, early stage and mid-market businesses typically “see” something that needs to be fixed (the holes in the cheese), “feel” the scope of the problem and then develop the processes to solve it. They believe in systems and accountability, yet intuition is key in turning their observations into innovations.

Kim Shepherd, most recently CEO of Decision Toolbox, is one such amazing business builder. As I listened to her describe how she looks for unmet needs and then figures out innovative ways to solve them, I realized that she (like many successful entrepreneurs) is a great observer. She is able to see things with fresh eyes and successfully implement new solutions by creating systems that enable people to not just do their jobs but do them remarkably well. 

Kim is very much a Blue Ocean Strategist® not seeking to do “more of the same”

Beginning her business career in a recruiting firm in 1990, Kim quickly discovered she had landed in an industry that needed major retooling. As she told me: “What kind of business takes a large fee from a client to find an employee that neither the client nor the recruiting firm knows will be a good hire?” Annoyed by the lack of logic in the recruiting industry’s  business model (those holes in the cheese), Kim decided to rebuild it. She switched companies, helped the new one “see” that it was not in the healthcare business but in the staffing business, and grew it from $3MM to $100MM in four years. Applying what she learned there, she then built her own company and sold it to CB Richard Ellis. 

In 2000, Kim joined Decision Toolbox, a startup with great systems and the goal of improving the recruiting process. As she became 50% owner and CEO, she “saw” the opportunity to build this company into a highly innovative recruiting service that didn’t just find employees for clients but one that could transform the entire way businesses recruit new hires. By looking for the holes in the cheese, Kim built a business that rethought the way recruiting was done. 

To build a new type of recruiting firm, Kim focused on three areas that reflected her own cultural values and beliefs

In implementing her goal of creating entirely new solutions for nonusers by addressing their unmet needs, Kim concentrated on these three areas:

  1. Make it easy for people to work where they want to. Staff members don’t need to be in one location to be part of a company and share its culture. Decision Toolbox is completely virtual with 100 staff scattered over 14 states. 
  2. Processes drive profits, along with people. While Kim is clearly motivated by results and profits, she believes that these are products of and driven by strong processes, systems and data. Decision Toolbox has systems that almost autonomously manage the flow of incoming job requests with recruiters who best match that particular industry and the prior success those recruiters have had placing people in that industry. 
  3. Culture counts, a lot. Despite the geographic separation of staff, Decision Toolbox has built a strong culture of highly engaged staff who believe in teamwork and collaboration, and even fun. Each recruiter is independent yet closely tied to the corporate culture through team-building and socializing methods, often which the employees have created themselves.

Having recently sold Decision Toolbox to Engage2Excel (E2E), a leading provider of employee engagement solutions, Kim is now ready to start looking for “holes in the cheese” of the new entity. And in her spare time, she helps other entrepreneurs who are now coming to her to help them “see” unmet needs so that they too can be value innovators. What better mark of a truly successful entrepreneur — someone who does good and does well. Kim, I’m a fan. 

2 blogs on the importance of corporate culture

In order to build a successful business, a highly-functioning company culture is not just important, it’s absolutely critical. Here are two of our recent blogs that explain why.

If you’re an entrepreneur and want to improve your business’s culture (or find out what it is), give us a call for a free 1-hour consult.  

From Observation to Innovation,


Andi Simon, Ph.D.
President and CEO | Corporate Anthropologist
Simon Associates Management Consultants