Introduction: 0:00

• Introducing Aaron Gregory, co-founder and CEO of Upwardli. 
• Formerly serving as GC of Remitly and VP, Law & Public Policy at SmartSenseCom.
• Started his career in federal regulatory matters at Dentons and Kelley Drye & Warren.

Forging a career in highly regulated industries: 1:25

• Trying to become a corporate lawyer during the great recession and finding work at a law firm.
• Recognizing and acting on enormous changes in telecom created by industry consolidation. 
• Becoming a fintech specialist before it was a dominant field.

Advice to law students considering a JD-MBA: 7:20

• Recognizing his classmates’ passion for legal work and realizing he wanted to take a different path.
• Making difficult business decisions in areas of uncertainty.
• Overcoming fear to accept business-related risks.

Teaching yourself to become comfortable with uncertainty: 9:57

• Understanding that even a failing business can teach you a lot.
• Founding a company in order to live life to the fullest. 
• Viewing negative experiences as an asymmetric upside.

Leaving Remitly right before it went public to found a start-up: 15:10

• Feeling that the business functions you oversee have narrowed in the GC role.
• Identifying a problem in the credit market that inspired him to found a credit-focused start-up.

Unpacking Upwardli: 18:42

• Solving the challenge of credit invisibility that affects fifty million people in the United States.
• Serving as a bridge between companies who need to offer credit products and customers with limited access to credit, like recent immigrants, gig workers, and 18-25 year olds.
• Building a simple platform that offers a positive credit experience.

Bringing your business to a start-up accelerator: 22:26

• Receiving valuable education and mentorship at Techstars.
• Creating a reliable network of business leaders experiencing parallel issues.
• Getting a mark of approval and credibility by participating in a trusted accelerator.

Fundraising for your start-up: 27:05

• Learning to pitch effectively.
• Fully devoting yourself to fundraising instead of splitting your time on other tasks.
• Looking for people who believe in your idea and are willing to take a risk on you.
• Moving on quickly from people who aren’t sure about your business.

Making an effective pitch: 33:15

• Taking important lessons from bad pitch meetings.
• Needing to be able to share most important info verbally on cue.
• Learning how to pitch well via trial by fire.

Growing into the CEO role: 36:16

• Controlling for risk in all aspects of the business.
• Going beyond legal advisory to incorporate business needs into your decision-making.
• Mitigating the mindset shift from lawyer to leader.
• Finding healthy outlets for dealing with stress in a position of accountability.

Building Upwardli in Milwaukee, Wisconsin: 44:43

• Standing by the conviction that great companies and great talent can come from anywhere.
• Understanding that starting a tech company outside of the Bay Area or Seattle requires you to swim upstream.
• Allowing skilled people who left their hometowns for their careers to return and work for a great company.

Bonus questions: 48:48

• Favorite part of your daily routine.
• Professional pet peeves.

Book recommendations: 51:29

• High Output Management by Andy Grove.
• The Right It: Why So Many Ideas Fail and How to Make Sure Yours Succeed by Alberto Savoia.

What you wish you’d known as a young lawyer: 53:02

• Taking smart risks and understanding that you can always pivot when necessary.