Executive Advice on Entrepreneurship

This Private Advisory Board session on Entrepreneurship offered executive advice on topics ranging from wine making to consulting. Let’s dive right into the recap.


A Vistage member wants to know how to grow his winery into a larger entertainment venue.

The winery itself is successful and offers fulfillment to the CEO by both utilizing his agricultural background and providing an opportunity to educate his young family on business values and ethics.

Nonetheless, he ultimately wants his boutique winery to be the cornerstone for, or the stepping stone to, a larger business, incorporating other elements such as importing international wines, offering full bar service and liquor sales, possibly even adding a restaurant or movie theater.

Why Is It Important?

After six months of business, the CEO projects the winery’s sales at $100,000 this year, and potentially $500,000 next year. Based out of Idaho, customers range from as far away as Florida and Texas.

A business partner and a spouse both play important roles; the partner is more attuned to the need to expand, while the spouse is much more important in the “family” element.

Solutions (Suggestions)

Because of the youth of this company, and the largely undefined nature of its future, fellow members suggested that the CEO define a “role model company” to use as a model before proceeding. Other suggestions included focusing more on the success of the winery itself, and the need for a more comprehensive strategic and/or business plan.

Virginia-based Destination Sellers, that sells wine experiences, is offered as a role model company. Developing export markets and fully exploring differentiation are also suggested. The book Blue Ocean Strategy is also suggested as recommended reading.

Action Plan

Develop a plan by working with customers and research. It was determined that, for the CEO to best answer his question, these following questions should first be addressed:

  • What are my existing customers interested in?
  • How can I better express my future growth goals in a business plan?


A CEO sold his first business right when the economy crashed. What are his options now?

This issue hits on many questions near and dear to ex-top execs: What to do after your first success, and how to start a new business in the new economy?

Why Is It Important? The issue is important because the CEO thought that he would continue in commercial real estate but that world ended in 2009. He wants to become the next Dave Ramsey in the financial world.

How to best utilize his expertise? Should he write a book? Start a website? Start a new consultancy business?

Solutions (Suggestions): It was suggested that the CEO better identify the right demographic to which he’d target his new business, and then determine how to best sell to that niche. Some solid steps to achieve that presence were also included, such as branding the CEO’s name in social media, as well as increasing his presence on the seminar circuit.

Before going through the long process of writing a book, for example, it might make sense to launch a website with some instructional videos, first — a much faster step. Develop the CEO’s voice in snippets through social media or create a mobile app. A company offered as a model to look at was the Kahn Academy, which produces educational videos.

Action Plan: Sit down and define his demo, come up with a skeleton of what he wants to include in his financial toolkit and reassess what comes after that.

In two weeks, this member said he’s confident he’ll have his demographics defined and his business plan roughly created.
Originally published: Nov 29, 2011

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