Jim Prendergast – Founder & CEO, 317 Ventures

Helping others realize their full potential – whether as an entrepreneur, a young person in the business world, a father, a husband or a friend – Jim Prendergast admits that his favorite moments are those spent coaching, guiding and inspiring others. Leading with experience, heartfelt inspiration and a desire to share his life’s most teachable moments, Jim founded 317 Ventures in January 2017, marking a new chapter in his long business career.

After founding HealthiestYou, an innovative digital health company in 2011, that he sold in June 2016 to Teladoc, the nation’s leading provider of tele-health services, in a deal exceeding $155 million, Jim is now taking his experience as a serial entrepreneur and his personal passion for improving people’s lives to a new level. By helping position young, startup companies for success, Jim started 317 Ventures to use the business lessons he learned along the way, and is channeling his penchant for personal and professional coaching to fulfill his lifelong dream of helping others fulfill theirs. The company also leverages Jim’s 20+ years of building his own businesses – in financial services, insurance, employee benefits, and healthcare – to connect
innovative health and wellness companies with investors and financial opportunities to help them grow and prosper.

Throughout his years as a budding entrepreneur, Jim built his companies by focusing on creating a positive company culture and shaping entrepreneurially-minded teams that were invested in their own success to help the company succeed. That approach, a key factor in his business success strategy, is one that he applies now to help grow his clients’ companies. Along with building a people-first workplace culture, Jim’s personal investment in the success of others has built his reputation nationally as strong and compassionate business leader.

In June 2016, Jim was named a finalist in the Consumer Technology category in the Ernst & Young Entrepreneur of the Year Awards for 2016. His company was also recognized with accolades, such as the Arizona Central “Top Company to Work for in Arizona” award and the Phoenix Business Journal “Best Places to Work” award. He also took HealthiestYou’s national ranking from #846 in the Inc. 5000 list of America’s Fastest-Growing Companies in 2015, to #397 on the Inc. 500 list in 2016, as well as to #34 on the exclusive 2016 Entrepreneur360™ list of the Best Entrepreneurial Companies in America as determined by Entrepreneur Magazine.

Jim speaks at health industry and leadership events nationwide. He has been featured on an episode of “Men’s Health Live,” the Radio Network of Men’s Health Magazine, and was a guest on the ShiftShapers’ podcast hosted by industry thought leader, David Saltzman. He previously was a speaker on a national, business success tour, as well as a regular on the “Extreme Money Makeover Tour,” and the co-host of a major market radio talk show.

When he’s not inspiring leaders or building businesses, he is busy coaching and mentoring youth, and is a board member for the National Center for Fathering, an organization that was created to respond to the social and economic impact of fatherlessness in America. Jim has been involved with Little League, and the youth organization, Ambassadors of Compassion. In addition, Jim serves on the Northridge Community Church Board in Scottsdale, Arizona. To help the church raise funds, Jim purchased Saddlecreek Coffee Company that he operates for the church. In addition to donating 100% of the proceeds to the church, his other goal with the coffee shop is to help teach entrepreneurship to the church’s youth. He also supports and works closely with Partners in Action, a 30-year-old Scottsdale, Arizona-based nonprofit organization operating orphanages and other humanitarian projects in 27 countries.

Tell me about your early career.
I started my career in finance: mortgage banking, investments, and insurance. I sold my first company in November 2006.

How did the concept for HealthiestYou come about?
I was introduced to the concept when a start-up, tele-medicine company was raising money in 2007. The more I got involved, the more I realized that the future was bright for tele-medicine, but that their model was not going to change healthcare.

How was the first year in business?
The first year was exciting, optimistic and energizing. What could possibly go wrong? 🙂 It’s after the first year when you’re hit in the face with reality. Businesses take time and lots of pivots to find the right product, pricing, messaging, and market fit.

What was your marketing strategy?
I was heavily influenced by blue ocean strategy. We looked to go where no one else was going. We essentially did the opposite of our competition. They had a low utilization, low priced (commodity) product focused on large employer groups. We built a high utilization model with a price that could sustain that utilization and focused on small- to mid-sized groups. No one could on board and administer small groups efficiently, so they were forced to focus on large blocks of business. We set our sights on the ten million small businesses and how we could make a difference for them through employee retention, reducing health care premiums, absenteeism, etc.

How fast did the company grow during the first few years?
Year 1: $300,000
Year 2: $700,000
Year 3: $1,300,000
Year 4: $3,000,000
Year 5: $10,000,000
Year 6: $20,000,000

How do you define success?
Professionally: When a company’s core values are represented by every employee in every situation, resulting in consistency and profitability.

Personally: The choice to use your time how you want and not how others want you to. For me, it’s about truly living out my priorities of God and family, before chasing power and wealth.

What is the key to success?
Persistence, Passion, People and Pivoting. I believe everyone can be successful if they stay in the game long enough, surround themselves with good people, and are willing to listen to what the market wants and needs, and make those changes, no matter how many there are.

What are the greatest lessons you’ve ever learned?
There are two:

1) EVERYTHING happens for your own good, if you view it as a learning experience and not as a distraction or failure. Every time we had a setback, we realized it was a set up for something bigger. That mindset is critical to surviving as an entrepreneur.

2) Money doesn’t make you happy. The day I saw my bank account with all the zeroes in it, I felt nothing. Although I have a large home and can do/buy whatever I want, there is little to no joy in that. People should never sacrifice time with their loved ones for material wealth.

What are some of your favorite books?
Business: The Four Agreements, all of Patrick Lencioni’s books, Blue Ocean Strategy, Traction, and Three Feet from Gold.

Personal: Shadow Divers, Endurance, Unbroken, and Confidence Game.

Tell me about one of the toughest days you’ve had as an entrepreneur.
1) Many times, I could not make payroll. Having to tell your team that you will be late paying them is gut-wrenching.
2) Being told by investors that promised to send money that they changed their mind.
3) When a large payer made an offer to buy us at a time when I was dead broke. I had to turn it down, although it would’ve been good for me personally/financially. The deal didn’t make sense for my investors or employees. I was devastated, but believed something better was coming in the future. We sold two years later for 10x more.

When faced with adversity, what pushes you to keep moving forward?
1) Belief – You have to KNOW that you will make it. I have a mantra, “The harder the struggle, the bigger the reward.”
2) Family/wife – I believe your spouse must be 100% behind you, at all times.

What advice would you give to young entrepreneurs?
1) It’s all about the story. Figure out your story and then find a compelling way to tell it so everyone can easily understand it.
2) It will take a lot longer than you think and cost 5x more than you think, but you can do it.
3) Everything happens for a reason.
4) Don’t lose sight of your priorities.
5) 99.9% of all your large deals will fall through. Don’t count on any of them.
6) Find the blue ocean and hit a lot of singles. The homers will come in due time.
7) Don’t quit. You’re three feet from gold.

Who else should we interview? Nominate someone!

Interviews are conducted for research purposes by author Jason Navallo for his upcoming book, Underdog.

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