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Chris Ragain, CPA – 2016 20 Under 40 Superstars Honoree


Chris Ragain, CPA

Ragain Financial Inc.
Bonita Springs, FL




Aside from the accounting websites, which blog/website do you consider a must-read?

Blake Oliver writes a great roundup of cloud accounting issues.  His site is and as accountants become more and more responsible for the technology our clients use, his piece is a great resource.  I also religiously attend the shareholder updates and read everything that come out of Intuit.  The conference calls give you a real sense of where the company is headed.

In what ways have you contributed to your firm/company to make it better?

I started my firm about 15 years ago in Chicago IL.  Since starting, we have grown to serving over 360 clients and have offices in Florida and Minnesota.  Several years ago I decided to focus my business solely on small business owners and their accounting needs.  I felt this was an underserved community.  I put together affordable packages of services for them that give them all the compliance services they need and unlimited consultation with our staff.  I made tax planning a priority and saving their business and families money became a passion of mine.   I also expanded our services to include an investment advisory department.  I want to be a one stop shop for business owners, helping them with day to day tasks as well as saving for their future.  In 10 years the investment practice has grown about 250%.  The package offerings have proven to be a successful model and we serve small business owners across the country like doctors, restaurant owners, landscapers, insurance agents and the list goes on and on.

In what ways do you participate in the professional community to change/improve the accounting profession?

In the last 5 years I have been committed not only to my practice, but to creating accounting software platforms like ProHub 360, LedgerSync and Tax Planner Pro.  Tax Planner Pro is now featured on the Intuit App Store and serves over 2000 clients and accountants.  Helping other accountants save time and increase profitability is a big part of what I do now.  I want to show others in my profession how to make their practices as successful as mine has been and give them the tools needed to do it.  I host webinars and provide classroom like tutorials that show how I grew my firm and how they can grow theirs too.  This October I was invited to speak at QuickBooks Connect about marketing practices on social media and participating in a panel discussion about the future of bookkeeping and accounting.

In what ways do you participate in your local community to help others?

I participate regularly in charities that promote free enterprise and the importance of accounting.  Some of those groups include Enactus (formerly SIFE), Junior Achievement, and several financial literacy projects.

What changes do you foresee in the accounting profession of the near future (3-5 years)?

Compliance services will soon be done through Artificial Intelligence systems.  This includes tax return preparation, payroll services, and the day to day bookkeeping work.   Software already is pushing us toward more advisory roles.  Clients will begin to ask more time of accountants as it relates to strategy.  We are also starting to see package pricing and published pricing on websites start to flourish.  This will continue as clients demand more transparent services.

How do you see yourself participating in shaping the future of the accounting profession?

Software development has become a major focus of mine now.  I learned how to code several years ago, and I have built a team of developers that work on several projects at once.  Our newest and most promising initiative is a software called “Halon Tax”.  This is a tax software that blends artificial intelligence with real tax professionals to offer business tax return preparation.  My hope is to focus on the areas of tax that can be automated and bring software solutions to market that provide those services at a fraction of what they used to cost.

What is your career philosophy?

Work hard and take pride in the work you do.  Take good care of the staff that supports you.  Constantly be finding ways to improve your business and your expertise in your field, never stop learning and seeking ways to do and be better.  I’m always looking for ways to make my clients smile, which is no easy task when it comes to taxes, but it’s always a worthwhile effort.  I’m always trying to see things from the client perspective and letting that guide how we do our work rather than focusing on how we want our clients to think.  In negative situations I find there is always something to learn from it and many of the conversations internally with my staff is about how to turn these situations around so they don’t happen again.

Describe one person who has been an important mentor to you and how that person helped change your life.

Easily my biggest influence professionally has been a professor I had in college.  His name is Robert Wyatt, Ph.D. and is now the president of Coker College.  While he was one of my accounting professors and his classes were great, he showed me the value of never being satisfied with my work, that it could always be better.  He helped me refine my public speaking (he was my SIFE faculty sponsor) and together we and our team won the national and world SIFE championships.  I would not be the person I am today without his influence.



Learn more about this year’s 40 Under 40 Honorees.