Join Brett Gilliland with Aaron Klein as they talk about understanding how much risk people take. Aaron is the CEO of Riskalyze. The company started from the standpoint of empowering the world to invest fearlessly. He has created a framework to help clients understand and react to risks accordingly. In this episode, he discusses how to turn short-term decisions into long-term financial outcomes.

Clients Get To Become Heroes

Financial advisors do heroic work. The idea comes from the storytelling framework best read from the book “Building a Story Brand” by Donald Miller. Yet, Aaron points out that when the financial advisor becomes the story’s hero, the client is reduced to a mere spectator. The financial advisor cannot singlehandedly save the day and get the client to the other side. Clients must be deeply engaged in making short-term decisions so financial advisors can turn them into long-term outcomes. The financial advisor is more of a guide for the hero – the client. To put it in a much clearer analogy, Aaron compares this to Star Wars. He personifies the client as Luke Skywalker and the financial advisor as Obi-Wan Kenobi. Aaron breaks it down into the hero having a challenge that needs to be overcome. The whole point of it is that the hero meets a character that assumes the position of a guide and gives advice. With this setting, the hero wins.

A Different Kind of Leader

Over the years, the role of a leader has changed a lot for Aaron. In the early stages of the company, they were only three people. They almost failed and shut down in two years, but luckily they made it through. From there, the company grew to ten people, then to 25. Today, his company is 200 strong. At every stage of growth, the challenges were different, which made Aaron adapt his strategies. His objectives were simple and are collectively known as blame-based culture. The first objective is that Aaron and his team do not get blamed if the company does not reach its goals. The second objective is to make sure the company reaches its goals. Having seen some dysfunctionality also led to Aaron creating core values for the company. It was successful at keeping the company aligned with its direction. The ability to adapt to rising challenges is the defining characteristic of a different kind of leader.

About Aaron Klein:

Aaron Klein is co-founder and CEO at Riskalyze, the company that invented the Risk Number® and empowers the world to invest fearlessly. The company is headquartered in Auburn, California, and serves tens of thousands of financial advisors.

He is husband to Cacey Steward Klein, dad to Spencer (born in South Korea), and Emma and Teddy (born in Ethiopia).

Aaron has spoken at conferences and events such as the Fearless Investing Summit, the T3 Advisor Conference, Tiburon CEO Summit, Wealth Management CEO Roundtable, the Benzinga Fintech Awards, DataDisrupt, Startup Grind, Lifesong Celebrate Life, and an untold number of conferences for wealth management enterprises such as TD Ameritrade, Pershing, Carson Wealth, SSG, United Planners, Founders Financial, Waddell & Reed and more.

Aaron and Cacey co-founded Hope Takes Root, an initiative to use vocational training and life mentoring to change the future for orphans and at-risk kids in Ethiopia. He also sits on the board of Invest in Others, an organization that supports financial advisors who give back to their communities.

Previously, Aaron was elected as a Sierra College Trustee three times and served from 2004-2016. Investment News named him as one of the industry’s top 40 under 40 executives in 2015.

Outline of the Episode:

[02:20] Recalling the start of the company

[06:53] Aaron’s vision of where the industry is going

[10:14] Fear and greed as main motivations to take action

[15:11] Turning clients into heroes

[19:49] Making confirmation bias as an advantage

[25:27] How Aaron defines leadership

[30:20] Upholding Riskalyze’s nine core values

[37:32] Shifting narratives to evaluate where the company goes

[39:35] Put the cult in culture

[40:39] What makes an advisor unique for their clients

[42:29] Aaron talks about Hope Takes Root


Riskalyze Website:

Hope Takes Root Website:

Personal Website:



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