Commerce Conversations

Combatting the Retirement Crisis, with Aaron Schumm

Episode Summary

This episode of Commerce Conversations features a conversation between Dan Rosen, founder and partner at Commerce Ventures, and Aaron Schumm, CEO and founder of Vestwell. They discuss Aaron’s journey from a blue-collar Chicago upbringing to becoming a serial entrepreneur. Aaron shares how early interests in finance, shaped by his father’s stock market discussions, led him to a corporate finance career and eventually to entrepreneurship. Aaron recounts pivotal experiences, like founding and selling a startup before Vestwell, which focuses on addressing America’s retirement crisis. His journey has been marked by challenges, including capital-raising difficulties during COVID-19 and the need to build core technology from scratch. He highlights the complexity and patience required in building financial infrastructure and acknowledges how government legislation, especially bipartisan efforts on Capitol Hill, impact the financial sector. Aaron also expresses admiration for industry leaders like Jamie Dimon and emphasizes the importance of solving real-world problems with purpose. His advice to aspiring founders focuses on patience, problem-solving, and humility, advocating for building businesses that contribute positively to society.

Episode Notes

1. Introduction

• Host Julie Verhage Greenberg introduces the Commerce Conversations podcast and the episode’s focus: a conversation between Dan Rosen and Aaron Schum, CEO of Vestwell, discussing Aaron's journey, entrepreneurship, and the U.S. retirement crisis.

2. Aaron’s Background and Early Influences

• Aaron shares his upbringing in a blue-collar family in Chicago, where his father’s interest in the stock market sparked Aaron’s own passion for finance.
• Despite not seeing himself as an entrepreneur early on, Aaron recalls his early interests in problem-solving and teamwork, which set the foundation for his future in financial services.

3. Journey to Entrepreneurship

• After an initial career at Northern Trust, Aaron moved to New York, pivoting toward fintech. He gained experience as a product manager in CheckFree, which later influenced his approach to financial technology.
• Aaron describes his first entrepreneurial venture, starting FolioDynamix, and the eventual acquisition by Envestnet, detailing the challenges and emotions around selling his first startup.

4. Founding Vestwell

• Post-FolioDynamix, Aaron quickly transitioned into founding Vestwell to tackle the retirement crisis. He felt a strong conviction about Vestwell’s mission and was motivated to address the issue of savings in America.
• Aaron highlights the challenges he faced building the company’s infrastructure from scratch and explains how the experience helped him refine his approach to problem-solving in a startup environment.

5. Challenges and Perseverance

• Aaron recounts the difficulties Vestwell encountered, particularly raising funds during COVID-19 and convincing investors of the company’s value in an industry where understanding core infrastructure is complex.
• He also reflects on a challenging Series C funding round, compounded by personal struggles, but explains how the experience underscored the importance of patience and adaptability.

6. Engagement with Legislation

• Aaron talks about working with legislators on Capitol Hill to advocate for retirement reform and drive awareness of the retirement crisis. He underscores the bipartisan support and dedication he observed, appreciating the intelligence and commitment of many in the political sphere.
• He mentions bringing industry leaders together to discuss solutions and advocate for policy changes that benefit the public.

7. Views on Fintech and Industry Trends

• Aaron discusses the importance of core infrastructure in fintech, noting his belief that many recent innovations are more sustainable as features than standalone businesses.
• He comments on the wave of AI-driven ideas and solutions, highlighting the need for these innovations to address real problems meaningfully.

8. Mentorship and Influences

• Aaron shares his admiration for various business leaders, such as Jamie Dimon and Bill Crager, and mentors who influenced his perspective on leadership, strategic thinking, and problem-solving.

9. Advice for New Entrepreneurs

• Aaron advises new founders to focus on solving real-world problems, remain humble, and embrace the inevitable challenges and learning curve that come with building a startup.
• He encourages founders to be open to feedback and leverage the knowledge of others, stressing the importance of purpose-driven work.