Roy Sailor – Venture Partner, Caduceus Capital Partners; Principal, TellTale Advisors; Former OptumInsight Executive

You have robust leadership experience in healthcare operations and tech, and as a successful entrepreneur. Tell me how your career led you to become an early stage investor.

In my most recent position at Optum, I worked on our corporate M&A team, focused on strategic partnerships.  In this role, I found companies outside of Optum that aligned with our strategic initiatives and constructed partnerships where both companies would consume technology and services from each other. In some cases, we would go to market together and/or result in equity arrangements.

I really enjoyed the opportunity to work with private investors and entrepreneurs in this capacity. So, when I decided to retire from Optum in 2020, I developed a “post-corporate” plan which included advising and investing in early-stage digital health companies.

There are so many startups trying to succeed in digital health these days. How do you find the companies worthy of investment? What qualities do you look for in a startup?

Successful healthcare tech companies start with a great idea that will help make healthcare better. It’s important that the culture of these companies promotes integrity, honesty, respect, compassion, value creation, flexibility, dedication, and hard work.

Along with this, the leadership team must have strong advisors with deep healthcare, operations and development experience, and strong networks to make connections that make a difference.

What’s the best piece of advice you’ve ever received?

As leaders, we should seek to surround ourselves with great people who share our values and are much smarter than us. Then, our job as leaders is to get those people everything they need to do a great job. After that, get out of the way!  To me, this is the foundation of servant leadership

How do you go about building a great management team for a new business?

During the interview process, I look at how the candidate will solve problems, their leadership style, and how they will align with other team members and the organization overall. When a new leader comes on board, I make an extra effort to ensure that they have the context, knowledge, and information to be successful.  Along the way I look for opportunities to help them with early successes to build momentum.

For those who are interested in becoming entrepreneurs, what are the three most important things they should consider before launching a company?

  1. Be realistic. Have your eyes wide open as to the value of your concept/product with an understanding of the full life cycle of the process from idea to a real business to a successful business. Understand and commit to the level of effort that it will take to be successful. Know that it will likely be harder than you imagine.
  2. Develop a sales mindset from the first day and never stop selling.
  3. Develop a realistic financial plan and pay attention every day to that plan. Remember, cash is king.

What have you learned from your mentors over the years and how has it helped you to achieve success in your endeavors?

My mentors taught me to be honest and work with integrity.  Be present and engaged with whoever you are speaking to, be genuinely interested in what they are saying, listen to understand, and be gracious and compassionate. Everyone has a story, make it your objective to learn about that story, remembering that you need great people that are smarter than you to be successful.

What books made a difference in your business thinking?

“My Life and The Principles for Success” by Ross Perot and “On Becoming a Leader” by Warren Bennis.

If you did not have a career in health care business, that career would you pursue?

I would have pursued a career in ministry.

If someone is looking to invest in a venture capital fund, what advice would you give them?

I always invest in people. So, my advice would be to get to know the people who are leading and operating the venture capital fund before you invest.

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