Inner Circle
Join Inner CircleJoin
← Back to Library
Content

Stop Letting Taxes Leak Through Your Roofing Business

📅 August 22, 2026 ⏱️ 54:19 🎤 Randy, Chris Middleton, Tyler Berler

Chapters

Click to jump to section

  • 0:00
    Avoiding Overpaying Taxes
    The hosts introduce Chris Middleton and Tyler Berler, experts in tax strategies to prevent businesses from overpaying taxes.
  • 1:47
    Chris's Background in Tax
    Chris Middleton shares his journey from working in construction and psychology to becoming a tax expert focused on proactive tax planning.
  • 7:15
    Tyler's Entrepreneurial Journey
    Tyler Berler discusses his entrepreneurial path from a farm kid to co-founding Make Taxes Fair, driven by his own frustrations with high tax bills.
  • 14:53
    Forming Make Taxes Fair
    Chris and Tyler recount how their differing yet complementary skills led them to partner and establish Make Taxes Fair, emphasizing the importance of diverse partnerships and shared values.
  • 27:17
    The 'Clear Edge' Framework
    Chris introduces their comprehensive 'Clear Edge Framework' for tax planning, covering credits, legal structure, employee compensation, wealth accumulation, and exit planning.
  • 43:56
    Owner Compensation Strategies
    The discussion delves into proper owner compensation within an S-Corp structure to optimize payroll taxes and maintain IRS compliance.
  • 55:12
    Why CPAs Miss Strategies
    Chris explains that most CPAs are 'happy historians' focused on compliance, lacking the time or expertise for proactive, strategic tax planning.
  • 1:03:35
    The Augusta Rule Explained
    Tyler elaborates on the Augusta Rule, a strategy allowing homeowners to rent their personal residence to their business for tax-free income.
  • 1:08:54
    ADA Compliance Tax Credit
    Chris highlights a lesser-known tax credit for businesses investing in ADA compliance for their websites and marketing efforts, offering up to $5,000 annually.
  • 1:15:00
    Best Time for Tax Planning
    The speakers advise that the best time for tax planning is always now, emphasizing that early and consistent planning yields the best results.

Speakers

R
Randy
Host
C
Chris Middleton
T
Tyler Berler

Key Takeaways

✦

Review your legal structure (e.g., S-Corp election) to ensure it optimizes your tax situation, especially regarding self-employment taxes.

✦

Proactively determine reasonable owner compensation for yourself to minimize payroll taxes while staying compliant with IRS regulations.

✦

Explore tax credits like the ADA compliance credit (up to $5,000 annually) for investments in accessible websites and marketing materials.

✦

Utilize the Augusta Rule to rent your personal residence to your business for events (e.g., meetings, parties), allowing you to receive tax-free income from your company.

✦

Implement strategic tax planning year-round rather than waiting until tax season; early planning allows for more effective implementation of strategies.

✦

Seek out tax strategists who offer proactive planning and implementation support, as traditional CPAs often focus only on historical compliance.

✦

Be self-reflective and delegate financial and tax planning to experts, allowing you to focus on your core business operations and vision.

Want the full experience?

Join the Inner Circle for full access to every episode, AI-powered insights, personalized coaching, and a network of industry leaders.

Join Inner Circle →
POWER100

Inner Circle Membership Portal © 2026 Power100. All rights reserved.

power100.io