Level Up is Dealing With Debt’s flagship weekly livestream, where Desmond Stinnie (DWD Founder) and Addison Wiggin (NYT Bestselling Author) explore money, meaning, and momentum.
Level Up - Episode 15: Ken Mohammed of American Consumer Credit Counseling discusses how mindset and community can turn life’s toughest challenges into success
In this powerful episode of Level Up, host Desmond Stinnie sat down with Ken Mohammed, from American Consumer Credit Counseling for a heartfelt conversation about his journey helping people navigate life’s toughest seasons to building lasting stability. Ken shares how mindset and community shaped his passion for helping others.
1 Oct 2025
Level Up - Episode 13: Jack Corlis & Michelle Joyce Lead Towson University's Innovative Trades Program
In this episode of Level Up, we explore how Towson University is pioneering a new model of learning that blends skills, academic opportunity, and future-proof careers.
TU is redefining what education can look like. The Trades Development Program gives hands-on training across multiple skilled disciplines — from HVAC to carpentry to electrical — while creating a path to both the workforce and college completion.
1 Oct 2025
Level Up - Episode 14: Welcoming Sean Lenderink & Smart Loan Aid to the Community
Student loan debt is one of the most pressing financial challenges facing millions of Americans today. For many, the rules, repayment options, and forgiveness programs feel overwhelming and confusing. In this episode of Level Up, we welcome Sean Lenderink, founder of Smart Loan Aid, who has dedicated his work to bringing clarity and relief to borrowers navigating this maze. Sean shares the story behind Smart Loan Aid, the common misconceptions he sees every day, and how personalized guidance can turn anxiety into confidence.
As part of this conversation, we also celebrate Smart Loan Aid’s new social group inside the DWD platform, where members can get answers to their toughest student loan questions in a supportive, community-driven space. Whether you’re buried in debt or simply want to understand the system better, this episode introduces a new resource—and a new voice—committed to helping the DWD community take control of their financial futures.
21 Sept 2025
Level Up - Episode 12: Rep. Karen Alzate Recaps Her Legislative Victory Against Predatory Lending in Rhode Island
In this episode, we sit down with Rep. Karen Alzate to discuss her newly passed bill regulating payday lending in Rhode Island. She breaks down how the legislation closes loopholes, protects borrowers, and marks a major step toward ending predatory lending. This is the inside story of this victory and what it means for Rhode Islanders.
9 Sept 2025
Level Up - Episode 11: A Conversation with Jonas Sheckler, Asst Dir of Financial Wellbeing at Towson University
At the moment, you won't find many universities with dedicated resources for helping students with financial literacy. That makes Jonas C. Sheckler, Assistant Director of Financial Well-Being at Towson University, one of the handful of professionals in higher education focused on guiding students through money management and real-world financial decisions. His position represents a rare but growing recognition that students need more than academic knowledge to succeed after graduation.
In this conversation, Jonas makes the case that financial literacy should be treated as a core part of the college curriculum—and that there is a real upside for universities to adopt this philosophy. Sheckler digs into the details of Towson’s recent launch of its financial well-being initiatives, the challenges of building student buy-in, and why preparing young adults to navigate money is one of the most urgent responsibilities of higher education today.
29 Aug 2025
Level Up - Episode 10: Inside Student Loan Policy with NASFAA’s Senior Policy Analyst
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.
12 Aug 2025
Level Up - Episode 9: Trades, Tech, and Tomorrow
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.
6 Aug 2025
Level Up - Episode 8 - Marriage, Money, and a Mission: The Story Behind Calendar Budget App
Level Up is thrilled to welcome Eric and Robin Poulin, the visionary co-founders—and dynamic married duo—behind Calendar Budget (https://www.calendarbudget.com), 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.
30 Jul 2025
Level Up - Episode 7: A Conversation With Cory McCray
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.
23 Jul 2025
Level Up - Episode 6: Talking Trades With Got Electric
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.
11 Jul 2025
Level Up - Episode 5 - Roxie Overaker Visits Level Up Podcast
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.
2 Jul 2025
Level Up - Episode 4: Level Up Welcomes Samantha Cornmesser to Discuss How to Make Trades Skills Cool Again
Samantha Cornmesser, Director at CECU, highlights the importance of skilled trades and how strategic partnerships promote both career readiness and financial well-being in an interview.
24 Jun 2025
Level Up - Episode 3: DWD welcomes Preston Zapffe to the platform
Certified Financial Planner Preston Zapffe joins the Dealing With Debt platform to create content demystifying personal financial planning using his background in personal finance and private equity in this interview.
17 May 2025
Level Up - Episode 2: DWD Co-Founders featured on Trending In Education Podcast
Co-founders Desmond Stinnie and Addison Wiggin discuss financial literacy, the complexities of debt, and accessible financial education with host Mike Palmer in this interview.
17 May 2025
Level Up - Episode 1: Unmask The Hero
Ray "Coach Shoe" Schufford discusses the support needs of first responders and how the DWD platform can create a national community in this interview.
Who has been a guest on Level Up
Names identified in recent episode analyses. Showing up to five guests.
Samantha Cornmesser
Preston Zapffe
Desmond Stinnie
Addison Wiggin
Ray "Coach Shoe" Schufford
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
YouTube views
93,390
Score snapshot 15 Sept 2025
Podcast Authority Score: 28 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
22
Social presence
0
YouTube
85
Engagement
0
Contact Level Up
Guest appearances
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