Level Up

Dealing With Debt
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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.

  1. Level Up - Episode 15: Ken Mohammed of American Consumer Credit Counseling discusses how mindset and community can turn life’s toughest challenges into success

    10/14/2025

    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.

    41 min
  2. Level Up - Episode 13: Jack Corlis & Michelle Joyce Lead Towson University's Innovative Trades Program

    10/01/2025

    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.

    1h 9m
  3. Level Up - Episode 14: Welcoming Sean Lenderink & Smart Loan Aid to the Community

    10/01/2025

    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.

    46 min
  4. Level Up - Episode 12: Rep. Karen Alzate Recaps Her Legislative Victory Against Predatory Lending in Rhode Island

    09/21/2025

    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.

    36 min
  5. Level Up - Episode 11: A Conversation with Jonas Sheckler, Asst Dir of Financial Wellbeing at Towson University

    09/09/2025

    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.

    49 min
  6. Level Up - Episode 10: Inside Student Loan Policy with NASFAA’s Senior Policy Analyst

    08/29/2025

    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.

    1 hr
  7. Level Up - Episode 9: Trades, Tech, and Tomorrow

    08/12/2025

    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.

    1 hr
  8. Level Up - Episode 8 - Marriage, Money, and a Mission: The Story Behind Calendar Budget App

    08/06/2025

    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, 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.

    1h 6m
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About

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.

Information

  • Creator
    Dealing With Debt
  • Years Active
    2K
  • Episodes
    15
  • Rating
    Clean
  • Copyright
    © Dealing With Debt Inc
  • Show Website
    Level Up