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Meet Diana McCaskill of Fruition Consulting in North Park

Today we’d like to introduce you to Diana McCaskill.

Richard and Diana McCaskill started Fruition Consulting in 2005, after gaining extensive operational experience in hotels, convention and visitors bureaus, convention centers, entertainment/restaurant businesses along with general business development consulting. Diana’s 20+ years in the hospitality industry provides a level of expertise perfectly suited for leading this team. Under her leadership, Fruition has provided conference and event management services to various municipalities, non-profit and for profit organizations.

Fruition was always a “side” business as we focused our efforts on other entrepreneurial endeavors from touring bands nationally to developing an award-winning environmental company. In 2016, we made a decision to focus our efforts on developing Fruition.

Not only do we consult clients on their conferences, events and fundraising efforts, we will be launching our own brand of conferences and events geared toward small business owners. The primary reason for this was because in all of our experiences and all the small business owners we have had the pleasure of meeting along the way, the need for capital and lack of administrative infrastructure was a reoccurring issue.

Overall, has it been relatively smooth? If not, what were some of the struggles along the way?
The life of an entrepreneur is never a smooth one. As a means of investing in our company, we have leveraged everything we owned from taking a second mortgage on our home to maxing out our credit cards. During the economic downturn of 2008, our home was in foreclosure and completely destroyed by water damage. In an instance we became homeless, living in our office.

Many would consider this a low point in our lives. Instead, my husband and I started a boutique recycling company and grew it to a $1M company, with no money and no credit.

So NO, it has not been a smooth road, but we have come to realize we make a dynamic team capable of overcoming anything.

Fruition Consulting – what should we know? What do you guys do best? What sets you apart from the competition?
Fruition Consulting is a firm that increases companies’ visibility and profitability through business development, fundraising, conferences and project management services.

We specialize in creating memorable meetings and events internationally. Our teams’ backgrounds vary from entertainment, environmental, luxury fashion and hospitality industries. It is this diversity that sets our company apart from others. Collectively, we cover all aspects of the hospitality business which gives us an advantage as we negotiate on behalf of our clients.

I am most proud of our team and the outcome we produce. When you have a group of people that are dedicated and hardworking – and still manage to have a good time doing it, it doesn’t seem like work.

What is “success” or “successful” for you?
When I think of being successful, I look to accomplish three major goals:

  1. To have the freedom of time and money in order to live fully
  2. To be a positive influence and make a significant impact
  3. To leave a legacy

I am working feverishly to make these things happen.

Contact Info:


Image Credit:
Richard McCaskill
Mao Carerra

Getting in touch: SDVoyager is built on recommendations from the community; it’s how we uncover hidden gems, so if you know someone who deserves recognition please let us know here.

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