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The Profitable Advisor Podcast

Every month, million dollar fee-based financial advisor Dan Cuprill shares ideas and strategies on how build profit-driven planning practices. For more information, visit

Mar 1, 2022

Today we want to spotlight one of the first people to enroll in the Renegade Advisor program. Not because of that early relationship but because he’s incorporated many of the strategies we talk about and his success is taking off.

Ryan Fleming, MBA, RICP, CRPC has an incredible story as a former college football player and graduate of the Air Force Academy. He identified this niche and went all in on working with pilots. The business was profitable early on but the real growth came when he began trusting the marketing strategies we discuss all the time.

We asked him to join the podcast to share his journey as an advisor. Along the way, we expect you’ll pick up a few things that you can use in your own practice.

So as you go through the episode today, keep an ear out for some of these topics that we cover:

  • How he started reaching out to pilots and carving out this niche.
  • His marketing systems and when it all started to click.
  • What ways is he marketing his kit to pilots?
  • The main things that held him back early on
  • Uncovering landmines with prospects and how Ryan stays rigid to his approach as an advisor.
  • Keeping the emotion out of your meetings with prospects.
  • Generating referrals after taking a more holistic approach.

For more on this topic and other strategies to growing your business, join us over at


What we discuss in this episode: 

0:45 –Background on our guest  

2:10 – His credentials

3:38 – Decision to work with pilots

5:30 – Spending money to market

9:38 – Two things that held him back

12:00 – His rigid approach as an advisor

16:57 – A more holistic approach

19:38 – Writing a book

22:40 – Client appreciation event   

25:22 – Growth

28:37 – Recapping everything we’ve discussed