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.
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