In this episode of Level Up, hosts Desmond Stinnie and Addison Wiggin welcome Megan Walter, Senior Policy Analyst at the National Association of Student Financial Aid Administrators (NASFAA). Walter shares insights on the sweeping new legislation she calls the “One Big Beautiful Bill,” breaking down what it means for student aid and how financial aid offices are preparing for the changes. She also explains the negotiated rulemaking process, the restart of student loan repayment, and the compliance challenges schools are navigating under Title IV. Throughout the conversation, Megan highlights why financial literacy is essential to long-term student success and how NASFAA works with policymakers, institutions, and administrators to shape the future of higher education finance.

In this episode of Level Up, Addison Wiggin and Desmond Stinnie sit down with Mikhail Reece, a passionate advocate for trade careers and founder of the “Trades, Tech & the Next Generation” initiative. From organizing high-impact community events in Tampa to launching scholarships and leveraging social media, Mikhail is on a mission to redefine how young people see vocational paths. Together, they explore how hands-on skills, cutting-edge technology, and community storytelling can challenge the college-only mindset—and open doors to financial independence.

If you’ve ever wondered how the trades can shape the future, this conversation will inspire you to think bigger about tomorrow’s opportunities.

Level Up is thrilled to welcome Eric and Robin Poulin, the visionary co-founders—and dynamic married duo—behind Calendar Budget, a powerful budgeting app designed to bring clarity, control, and confidence to your financial life. In this episode, we’ll dive into the inspiring origin story of Calendar Budget, explore its standout features that make money management intuitive and visual, and hear firsthand how Eric and Robyn turned a personal need into an empowering tool for thousands. As like-missioned advocates for financial wellness, Calendar Budget and Dealing With Debt are excited to team up in service of helping consumers make smarter financial decisions.

Don’t miss this meaningful conversation about entrepreneurship, financial literacy, and how technology can help you take control of your future—one calendar day at a time.

In this powerful episode of Level Up, Desmond Stinnie and Addison Wiggin sit down with Cory McCray to discuss his deeply personal new book, The Apprenticeship That Saved My Life. Senator McCray shares how growing up in East Baltimore, facing real challenges, and entering the electrical trades through apprenticeship not only gave him a career—but redirected the course of his life. Now a respected public servant and advocate, McCray talks candidly about the life-changing potential of skilled trades, the need to reframe outdated narratives, and why policy and opportunity must align to create real access for young people. It’s a conversation about discipline, dignity, and the transformative power of work—told by someone who’s lived it. If you care about economic mobility, educational alternatives, or second chances, this is an episode you won’t want to miss.

In this episode of Level Up, Desmond Stinnie and Addison Wiggin sit down with Desmond's longtime friend and trades entrepreneur Grant Gotlinger, founder of Got Electric LLC. What begins as a personal reunion turns into an insightful conversation about Grant’s decision to leave college after his first year at Towson University, his journey into the electrical trades, and the long road to building a successful contracting business. Grant reflects on the realities of working in the field, the entrepreneurial lessons learned through experience, and why the trades offer a viable, rewarding, and often overlooked path to ownership and financial stability. It’s an honest, empowering conversation that redefines what it means to build success—on your own terms.

Roxie Overaker of American Consumer Credit Counseling (ACCC) stops by for an honest, stigma-free conversation about how financial stress impacts health, why judgment-free support matters, and what the future of debt counseling looks like.

A powerful conversation with Samantha Cornmesser, Director of Member Partnerships at Career Education Colleges and Universities (CECU), discussing the vital role of skilled trades in today’s economy and why organizations like Dealing With Debt are valued partners to trade schools for pairing workforce readiness with lifelong financial wellness.

In this episode, the Dealing With Debt community is introduced to Preston Zapffe, a Certified Financial Planner, to preview his plans for content creation for the platform. Preston will lean on his extensive background in personal finance and private equity to help members demistify the complex world of personal financial planning. DWD welcomes Preston's knowledge, passion, and more importantly, his humor and humility!

In this episode of Trending in Education, host Mike Palmer interviews Desmond Stinnie and Addison Wiggin, the co-founders of ⁠Dealing with Debt,⁠ a platform focused on financial literacy and community support. Desmond shares his lifelong passion for financial education, tracing back to his childhood curiosity about money. Addison brings his 30 years of experience in financial publishing and macroeconomic analysis, highlighting the evolution of consumer culture and debt. Together, they discuss the importance of understanding one’s relationship with debt, the distinction between good and bad debt, and the need for accessible financial education.

In episode 1 of Level Up, we are joined by Ray "Coach Shoe" Schufford - retired first responder and founder of 2 The Next Shift, to discuss the support needs of first responders and how the DWD platform presents an opportunity to fill in several gaps and create a national first responder community.