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Thank you to the 1,400 leaders who’ve generously done the 7 questions!
I hope reading

helps you in your leadership.



Jonno White

7 Questions with Ross Overline
7 Questions with Ross Overline

Name: Ross Overline

Current title: CEO

Current organisation: Scholars of Finance

Ross is the Co-Founder & CEO of Scholars of Finance (SOF), a fast-growing organization that inspires character and integrity in the finance leaders of tomorrow. SOF brings together leading investors and finance executives to teach undergraduate students how they can make an impact through finance and investing.

7 Questions with Ross Overline

1. What have you found most challenging as a leader of a small or medium enterprise?

We're a non-profit so one of the biggest challenges we face on a day-to-day basis is not having the resources to do all of the things that we'd like to do as an organization.

2. How did you become a leader of an SME? Can you please briefly tell the story?

In college, I organized an event for principled financial leadership with a few friends from the University of Minnesota and the University of St. Thomas. That was our first event. From there, one event turned into two and soon we started forming chapters and ultimately incorporated as a non-profit in 2018. I stepped in full-time as the CEO in July of 2019 and have been solely focused on helping grow Scholars of Finance ever since.

3. How do you structure your work days from waking up to going to sleep?

I use time-blocking to schedule my days. While there is some variance, I typically wake up at 5:00am and take the first part of the day to myself. From about 7:00am - 9:00am I respond to emails and get ready for the work day. After that most of my days are spent in meetings and helping coach up our team.

4. What's the most recent significant leadership lesson you've learned?

Being an entrepreneur I tend to try to do too much too fast. This is an area I'm still trying to improve in.

5. What's one book that has had a profound impact on your leadershiso far? Can you please briefly tell the story of how that book impacted your leadership?

Principles by Ray Dalio: Foundational book. Felt like someone was reading my soul to me. Ray outlines the principles that he developed to design leadership, management, and the organization of Bridgewater Associates, which became the top hedge fund on earth. Key takeaways: Radical truth and transparency are optimal. "Find out what is true and what to do about it".

6. How do you build leadership capacity in an SME?

I'm unsure if I understand the question. If you're asking how we get more people involved in leadership, we empower a lot. We have a small team with myself and one other FTE employee. Aside from that, we have a few part-time interns and an army of volunteer interns that are very bought into our mission.

7. What is one meaningful story that comes to mind from your time as a leader of an SME so far?

Well, there are several, but I think the one of the biggest lessons I had to learn was transitioning from being in middle-level management at a fast-growth fintech company to being the CEO of a non-profit where it was just me and 1-2 interns at the time. It took me a long time to reset expectations for output and it took our team a long time to get to a point where we were operating really efficiently.

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