Ep 55: Why Upwardli CEO Aaron Gregory Took the Leap from GC to Founder

How do you make the leap from lawyer to founder? How do you craft the perfect pitch? What does it take to fundraise effectively? And how far will your legal know-how take you when you’re accountable for every function in the business?

Join Aaron Gregory, Co-founder and CEO of Upwardli, as he shares his journey from general counsel to start-up leader. Starting his career in the highly regulated telecom and fintech industries, Aaron relied on lessons he learned while earning his JD-MBA to start a company that solves the challenges of credit invisibility for more than 50 million people in the United States.

Listen as Aaron discusses how he took on the challenges that all first-time founders face–like pitching to VCs, fundraising, and growing into the CEO role—and shifted his mindset from that of a risk-conscious legal leader to a business-focused operator.

Read detailed summary:  https://www.spotdraft.com/podcast/episode-55

Topics:
Introduction: 0:00
Forging a career in highly regulated legal areas: 1:25
Advice to law students considering a JD-MBA: 7:20
Teaching yourself to become comfortable with uncertainty: 9:57
Leaving Remitly right before it went public to found a start-up: 15:10
Unpacking Upwardli: 18:42
Bringing your business to a start-up accelerator: 22:26
Fundraising for your start-up: 27:05
Making an effective pitch: 33:15
Growing into the CEO role: 36:16
Building Upwardli in Milwaukee, Wisconsin: 44:43
Bonus questions: 48:48
Book recommendations: 51:29
What you wish you’d known as a young lawyer: 53:02

Connect with us:
Aaron Gregory - https://www.linkedin.com/in/amgregory/
Tyler Finn - https://www.linkedin.com/in/tylerhfinn
SpotDraft - https://www.linkedin.com/company/spotdraft

SpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues.

Visit https://www.spotdraft.com to learn more.