The Pittsburgh Hustle Project

Matt A. Dingus
  • 5.0 (2)
  • ENTREPRENEURSHIP
  • UPDATED MONTHLY

The Pittsburgh Hustle Project dives deep into the stories of the city’s boldest entrepreneurs, visionaries, and change-makers. From gritty beginnings to breakthrough moments, we uncover the raw, unfiltered journeys behind Pittsburgh’s most inspiring success stories. Whether you’re building a business, chasing a dream, or just love a good underdog story — this podcast is your front-row seat to the hustle, heart, and hard-earned victories that define the Steel City

Episodes

  1. Ep. 6: Behind the Flip: 1st Flip Breakdown & Lessons Learned | Trent Quinlan

    11/01/2025

    Ep. 6: Behind the Flip: 1st Flip Breakdown & Lessons Learned | Trent Quinlan

    In this conversation, Matt Dingus interviews Trent Quinlan about his first house flip project in Pittsburgh. They discuss the journey from searching for the right property to navigating the closing process, planning the scope of work, and the challenges faced during construction. Trent shares insights on managing subcontractors, the financial strain of using hard money loans, and the importance of staging when selling the property. He reflects on the lessons learned and his future plans in real estate investment. Takeaways Trent's journey into real estate began after a deployment. Finding the right property can be the hardest part of flipping. The importance of having a clear scope of work before starting a project. Unexpected challenges can arise during construction, impacting timelines and budgets. Managing subcontractors effectively is crucial for a successful flip. Financial strain can be a significant stressor during a flip project. Staging a property can greatly enhance its appeal to buyers. Learning from mistakes is essential for future success in real estate. Having a financial cushion can alleviate stress during a project. Partnerships can provide financial support and reduce individual strain. Titles From Deployment to Real Estate: Trent's First Flip Navigating the Challenges of House Flipping Sound bites "You make your money on the buy." "I was tracking every penny." "I was confident the house was well done." Chapters 00:00 Introduction to Flipping: Trent's Journey 03:08 The Search for the Perfect Property 08:48 Navigating the Closing Process 12:57 Planning the Scope of Work 17:02 Challenges in Construction and Layout 19:45 Dealing with Slab Foundations 23:30 Subcontracting and Managing Work 25:37 Final Thoughts and Lessons Learned 27:57 Navigating Hard Money Loans and Draws 29:47 Budgeting Challenges and Unexpected Costs 33:03 Setting the Right Listing Price 36:21 Managing Buyer Interest and Offers 38:44 Understanding Purchase and Selling Costs 41:32 Lessons Learned from the First Flip 42:53 Future Plans and Investment Strategies

    50 min
  2. Ep. 5: Scaling Life & Business: Lessons from The Perfect Average Day | Ryan Scialabba [Part 2]

    08/01/2025

    Ep. 5: Scaling Life & Business: Lessons from The Perfect Average Day | Ryan Scialabba [Part 2]

    In this conversation, Ryan Scialabba discusses his journey of self-discovery and the creation of his book, 'The Perfect Average Day.' He reflects on the challenges of balancing personal and professional life, the importance of mental health, and the need for a structured approach to daily living. Ryan shares insights on navigating the complexities of parenthood while managing a business, the significance of conflict resolution in both personal and professional settings, and the legacy he hopes to leave for his children. Takeaways The book 'The Perfect Average Day' was a mental exercise. Life's pressures can lead to feelings of being lost. Finding balance in life and business is crucial. The concept of bumper rails helps maintain focus. It's important to fill all personal buckets daily. Conflict resolution differs between business and home. Setting boundaries is key to buying back time. Teaching others how to think is essential for growth. Leaving a legacy involves instilling values in children. The future may be harder for the next generation.

    55 min
  3. Ep. 4: Building the Machine: Systems & Strategy in Real Estate Investing & Flipping | Ryan Scialabba [Part 1]

    07/26/2025

    Ep. 4: Building the Machine: Systems & Strategy in Real Estate Investing & Flipping | Ryan Scialabba [Part 1]

    In this episode of the Pittsburgh Hustle Project, host Matt Dingus interviews Ryan Scialabba, a serial entrepreneur and real estate investor. They discuss the challenges and strategies of running multiple businesses, the importance of partnerships, and the evolution of business operations. Ryan shares insights on project management in flipping houses, the differences between flipping and renting properties, and effective marketing strategies for real estate. The conversation emphasizes the significance of understanding the market, scaling responsibilities, and maintaining quality in renovations. Takeaways The journey of entrepreneurship involves continuous learning and adaptation. Partnerships can significantly impact the success of a business. Managing multiple businesses requires effective delegation and trust in team members. Understanding the real estate market is crucial for making informed investment decisions. Quality renovations can lead to long-term profitability in rental properties. Marketing strategies should focus on building relationships and consistent lead generation. Project management is key to ensuring quality in flipping houses. Flipping houses requires a different approach compared to managing rental properties. Investing in high-quality materials can reduce maintenance costs in the long run. Scaling a business involves understanding when to delegate and when to take control. https://www.ryanscialabba.com/ https://www.instagram.com/callmeshibby/ https://www.facebook.com/theurbaninvestor/

    1h 5m
  4. Ep. 2: From Hustlin' in the Streets to Business Owner/Mentor: Building a Resilient Mindset | Bradley Jacobs

    07/26/2025

    Ep. 2: From Hustlin' in the Streets to Business Owner/Mentor: Building a Resilient Mindset | Bradley Jacobs

    The Pittsburgh Hustle Project

    1h 19m
  5. Ep. 3 Cultivating an Entrepreneur Mindset & Mastering Work–Life Integration | T.J. Bencho

    06/16/2025

    Ep. 3 Cultivating an Entrepreneur Mindset & Mastering Work–Life Integration | T.J. Bencho

    In this conversation, Matt Dingus interviews TJ, a successful real estate investor and intrapreneur, who shares his journey from self-employment to working within a corporate structure while maintaining an entrepreneurial mindset. The discussion covers the importance of family, community, and personal values in business, the challenges of real estate investing, and the significance of gratitude and collaboration in achieving success. TJ also emphasizes the role of education and mentorship in developing an intrapreneurial mindset, as well as the importance of integrating family into business life and teaching children about financial responsibility. Takeaways The journey of entrepreneurship can take many forms. Family and community play a crucial role in business success. Property management is essential for real estate investing. An intrapreneurial mindset can thrive in corporate environments. Self-employment is not the only path to success. Gratitude is key to maintaining a positive mindset. Teaching children about finance is vital for their future. Collaboration can lead to greater success than competition. Personal values should guide business decisions. Sobriety and personal growth can transform one's life. Follow T.J. Bencho: Instagram: https://www.instagram.com/t.j.bencho/ https://www.facebook.com/thomas.bencho/ https://steelpointcapital.net/about-us/ Follow Matt: Instagram: https://www.instagram.com/mattdinguspgh?igsh=Z204YjZ2MjM3NnJk&utm_source=qr Facebook: https://www.facebook.com/share/1DNEQ8DXCT/?mibextid=wwXIfr TikTok: https://www.tiktok.com/@mattdinguspgh?_t=ZP-8vuUGigwTYV&_r=1

    1h 21m
  6. Ep 1: The Investor Contractor Expert: How to Work with Contractors & Win in Real Estate | Omar Mohamed

    05/23/2025

    Ep 1: The Investor Contractor Expert: How to Work with Contractors & Win in Real Estate | Omar Mohamed

    The Pittsburgh Real Estate Project: Episode 1: Omar Mohamed (Contractor, Investor, & Immigrant) In this conversation, Matt Dingus and Omar Mohamed explore Omar's journey from Egypt to the United States, his pursuit of the American dream, and the challenges he faced along the way. They discuss the importance of hard work, the lessons learned from hardship, and the skills gained from corporate America that helped Omar transition into entrepreneurship. The conversation also delves into the construction business, the dynamics of working with investors, and common mistakes made in real estate investing. In this conversation, Matt Dingus shares insights on navigating the real estate market, focusing on the importance of understanding risks, maximizing renovation returns, and differentiating between flipping properties and long-term rentals. He emphasizes the significance of project timelines, managing permits, and the challenges of change orders. Matt also discusses his personal investment strategies, motivation, and the lessons he aims to impart to the next generation. Follow Matt: Instagram: https://www.instagram.com/mattdinguspgh?igsh=Z204YjZ2MjM3NnJk&utm_source=qr Facebook: https://www.facebook.com/share/1DNEQ8DXCT/?mibextid=wwXIfr TikTok: https://www.tiktok.com/@mattdinguspgh?_t=ZP-8vuUGigwTYV&_r=1 Follow Omar/Mr.Property Remodeling: Instagram: https://www.instagram.com/mr.propertyo?igsh=MTk5c2prZ2s4N2VjMg== Facebook: https://www.facebook.com/share/1FVPMDvEmr/?mibextid=wwXIfr TikTok: https://www.tiktok.com/@mr.property_omar?_t=ZP-8vuUIXRNHV0&_r=1

    1h 24m
  • 6 Episodes

Ratings & Reviews

5
out of 5
2 Ratings

About

The Pittsburgh Hustle Project dives deep into the stories of the city’s boldest entrepreneurs, visionaries, and change-makers. From gritty beginnings to breakthrough moments, we uncover the raw, unfiltered journeys behind Pittsburgh’s most inspiring success stories. Whether you’re building a business, chasing a dream, or just love a good underdog story — this podcast is your front-row seat to the hustle, heart, and hard-earned victories that define the Steel City

Information

  • Creator
    Matt A. Dingus
  • Years Active
    2K
  • Episodes
    6
  • Rating
    Explicit