Sterling Insights

Are CPA firms really ready for succession—or just hoping they’ll figure it out later? Discover why waiting is the costliest mistake a firm can make.
In this episode of Sterling Insights, guest host Charles Trakas sits down with a seasoned advisor and CPA-turned-growth consultant, Daniel McMahon. Together, they explore succession planning, governance, and building enterprise value in CPA firms, sharing valuable insights and practical tips for listeners. Drawing from decades of experience in public accounting and management consulting, the guest unpacks the common challenges firms face when planning for transition and offers actionable advice to create firms that are sustainable, transferable, and truly valuable.
This episode is a must-listen for firm leaders, partners, and advisors working with CPA firms, providing both knowledge and tools to navigate succession with confidence.

Key Takeaways:

● 🔁 Succession Is a Process, Not an Event: Planning early and treating succession like a process—rather than a one-time event—ensures smoother transitions and sustained firm value.
● 🧱 Strong Governance Builds Strong Firms: Implementing clear governance structures creates accountability, alignment, and sets the foundation for long-term growth.
● 🕰️ The Tyranny of the Now: Many firm owners delay planning because they’re overwhelmed by day-to-day demands—this mindset threatens future viability.
● 🧠 Intellect Isn’t Enough—Action Is Required: Even highly intelligent partners struggle to act on succession plans without outside support and structure.
● 💼 Build a Business, Not Just a Book: Firms that are sustainable and transferable command higher valuations and are more attractive to buyers or internal successors.

Quotes from Daniel McMahon:

● “I’m not here to outsmart my clients. I’m here to help them take a step forward.”
● “Governance isn’t just board minutes—it’s a cultural process that drives alignment.”
● “If your firm is sustainable and transferable, you’re not just selling a practice—you’ve built an enterprise.”
🔗 Conclusion:
Succession doesn’t start when you’re ready to exit—it starts when you decide to build a firm that can thrive without you.

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What happens when a corporate dealmaker hits midlife and chooses law school over a sports car? In this episode, discover how attorney Kevin Timson brings deep business insight to legal strategies that help entrepreneurs and auto dealers plan smarter exits and succession.

In this episode of Sterling Insights, guest host Peter Florio sits down with Kevin Timson, an attorney at ArentFox Schiff with over 25 years of combined business and legal experience. Together, they explore succession planning, business exits, and long-term legal strategy for entrepreneurs and automotive dealership owners, sharing valuable insights and practical tips for listeners. Kevin draws from his unique path—from business development to boutique law firms to a national firm—offering real-world advice on navigating ownership transitions, valuations, and family business complexities. This episode is a must-listen for advisors, attorneys, and business owners planning for the future, providing both knowledge and tools to navigate this critical phase of business life.

Key Takeaways:

● 🔁 Succession Planning Isn’t One-Size-Fits-All: Kevin explains how every succession plan must be tailored to the family dynamics, asset types, and future goals of each business owner.
● 💼 Valuation is More Art Than Science: Owners often cling to fixed numbers, but Kevin emphasizes that value is ultimately what a willing buyer and seller agree on.
● 🧠 Business Owners Struggle to Zoom Out: Many entrepreneurs get stuck in day-to-day operations and neglect long-term planning—until it’s too late.
● 🧭 Trust is the Cornerstone of Advisory Relationships: Whether attorney or wealth advisor, success starts with mutual trust and a shared goal.
● 🛠️ Your Legal Partner Should Be a Problem-Solving Sherpa: Kevin sees himself as a flexible problem-solver who listens first and then curates legal strategies from a vast network of resources.

Quotes from Kevin Timson:

● “You never step in the same river twice—every business transition is unique.”
● “The best valuation is what a willing buyer and a willing seller can agree on.”
● “I aim to be a continuity-of-care provider—someone clients can trust across every phase of the journey.”

🔗 Conclusion:
Whether you’re a business owner nearing retirement or an advisor guiding clients through transitions, this episode delivers essential wisdom on how to plan with clarity, confidence, and the right team beside you.
Connect with Kevin:
Website:  https://www.afslaw.com/attorneys/kevin-timson
With Your Guest Host Peter Florio:
Peter F. Florio, CFP®, CLU®, ChFC®, CExP™, CLTC®, is the Founder and Managing Partner of The Florio Wealth Management Group in Westbury, NY. With nearly 40 years of experience, he provides comprehensive wealth, tax, and financial planning for high-net-worth individuals and business owners across the country.
Connect with Peter:
Website: https://www.floriowmg.com
LinkedIn: https://www.linkedin.com/company/florio-wealth-management-group/
Facebook: https://www.facebook.com/floriowmg
Calendly: https://calendly.com/floriowmg

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Most people obsess over hot stock tips — but what if true financial peace came from planning for what really matters? This episode challenges conventional thinking and offers a new lens on wealth, risk, and legacy.

In this episode of Sterling Insights, Roger sits down with Laura Rehbein, Private Wealth Advisor and Founder of Impavid Wealth Advisors. Together, they explore how to bring clarity and confidence to high-net-worth financial planning, sharing valuable insights and practical tips for listeners. Laura draws from her 30 years of experience to discuss emotional blind spots, legacy planning, digital assets, and the dangers of “bad math”, offering actionable advice for affluent professionals and retirees. This episode is a must-listen for advisors, wealth builders, and those navigating complex financial lives, providing both knowledge and tools to navigate this important subject.

Key Takeaways:

● 💼 Planning Is More Than Investing: True wealth management means planning for life events, risks, and what money needs to do for you — not just watching the markets.

● 📚 Why “Throw It in a Pile” Works: Laura’s simple but powerful method helps uncover forgotten accounts, misaligned goals, and missing documents.

● 🧠 Emotions Drive Money Decisions: Even smart, successful people struggle with fear and uncertainty around money — acknowledging that is key to great planning.

● 🐾 Don’t Forget the Pets: Estate planning isn’t complete without considering pets and digital assets — yes, even your Facebook page.

● ⚖️ Balance Assets for Flexibility: Too much in retirement accounts can cause tax headaches later. Strategic asset location matters.

Quotes from Laura Rehbein:

● “Measure money against the job it needs to do someday — and keep measuring, because life changes.”

● “People think they need investments. What they really need is clarity.”

● “You can have all the money in the world and still have a financial train wreck if you don’t plan beyond the numbers.”

🔗 Conclusion:

If you’re still focused only on returns, you’re missing the real value of planning. This episode will help you think bigger — and smarter — about wealth.

Connect with Laura:

LinkedIn: https://www.linkedin.com/in/laurarehbein/

LinkedIn: https://www.linkedin.com/company/impavid-wealth-advisors-a-private-wealth-advisory-practice-of-ameriprise-financial-services-llc 

Facebook: https://www.facebook.com/ImpavidWealthAdvisors

Connect with Roger:

Website:  https://www.sterlingfoundations.com

Facebook:  https://www.facebook.com/sterlingfoundations/

Twitter:  https://x.com/SterlingFndMgt?mx=2

LinkedIn:  https://www.linkedin.com/company/sterling-foundation-management-llc/

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Are you a business owner wondering how to build wealth without giving up control of your cash? This episode will change how you think about financing, investing, and navigating economic uncertainty.
In this episode of Sterling Insights, guest host Charles Trakas sits down with M.C. Laubscher, founder and wealth strategist at Producers Wealth. Together, they explore how business owners can use infinite banking to grow and protect their wealth, while maintaining access to capital. M.C. draws from his extensive experience as an investor, entrepreneur, and immigrant success story to discuss the real challenges business owners face—like liquidity, control, and taxes—offering actionable strategies for long-term financial independence.
This episode is a must-listen for entrepreneurs, financial advisors, and business owners, providing both insights and tools to take control of cash flow and create sustainable wealth.

Key Takeaways:
● 💸 Be Your Own Bank: Infinite banking helps business owners keep control of their capital while still getting growth and protection.
● 🔄 Cash Flow Seasons: Every business has high and low seasons—this strategy helps smooth cash flow in “winter” months.
● 🔐 Keep Liquidity & Control: Traditional diversification often locks up money—this approach keeps your money accessible.
● 🧾 Tax Efficiency: Proper structuring with life insurance can unlock tax advantages that boost net worth.
● 💼 Real-World Application: M.C. shares how his clients leverage these tools to fund real estate, business expansion, and personal goals—even during crises like the pandemic.

Quotes from M.C. Laubscher:
● “The IRS code is literally a playbook that tells you how to pay the least amount of taxes—legally.”
● “If you don’t understand the rules of the banking system, you’re just a piece on someone else’s board.”
● “Infinite banking gave me certainty when everything else collapsed—real estate, oil, even cash flow.”
🔗 Conclusion:
Infinite banking isn’t just a theory—it’s a practical strategy for business owners who want more control, better tax outcomes, and greater flexibility to scale. If you want to protect and supercharge your assets, this episode is your blueprint.
Connect with M.C.:
Website:  www.getwealthforsure.com
With Your Guest Host Charles Trakas:
Charles Trakas is the President of Trakas Financial, LLC, Senior Wealth Advisor with Redwood Private Wealth, and Founder of Proactive Tax Reductions. For over 26 years, he has helped high-net-worth individuals and business owners grow, protect, and transfer wealth through tax-efficient strategies. A lifelong entrepreneur and financial coach, Charles collaborates with CPAs, attorneys, and advisors to deliver comprehensive planning that minimizes taxes and maximizes long-term financial success.
Connect with Charles:
Website:  https://proactivetaxreductions.com/about-us/ LinkedIn:https://www.linkedin.com/in/businessownertaxreductionadvisor/ Facebook Business:https://www.facebook.com/TrakasFinancial  Facebook Personal:https://www.facebook.com/profile.php?id=100011447285280New boost

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What happens when values and financial advice don’t align? This episode explores how purpose-driven planning can reshape the advisor-client relationship—and why it matters more than ever for high-net-worth families.

In this episode of Sterling Insights, Roger sits down with Darryl Lyons, co-founder of PAX Financial Group and a Certified Financial Planner. Together, they explore purpose-driven financial planning through a Judeo-Christian lens, sharing valuable insights and practical tips for advisors and clients alike. Darryl draws from his extensive experience working with business owners and high-net-worth families to discuss value alignment, charitable giving strategies, and navigating today’s complex economic environment, offering actionable advice for financial professionals and faith-driven investors. This episode is a must-listen for advisors who serve high-net-worth clients and want to lead with purpose, providing both knowledge and tools to navigate this important subject.

Key Takeaways:

● ✝️ Aligning Faith and Finance: Why purpose-driven planning resonates with clients who want their investments to reflect their core values.

● 💼 Ideal Client Profile: How PAX Financial serves business owners with $10M+ net worth, especially those approaching succession.

● 📈 Net Asset Flow as Growth Metric: Why Darryl prefers tracking organic AUM growth over total assets.

● 🎁 Strategic Generosity: How donor-advised funds and thoughtful giving strategies can help clients give meaningfully—and tax-efficiently.

● 🧩 Navigating ESG & Proxy Voting: A candid look at how ESG investing intersects (and conflicts) with Judeo-Christian values.

Quotes from Darryl Lyons:

● “He didn’t want to wrestle with the why of giving—he wanted someone who already believed in it, and would focus on how to do it well.”

● “If you’re using the Lord’s name just to garner business, that’s using it in vain—and I take that seriously.”

● “We charge a modest fee because people value what they pay for—and we want them to take action.”

🔗 Conclusion: Purpose-driven financial planning isn’t just about performance—it’s about trust, alignment, and helping clients live out their values through their wealth.

Connect with Darryl:

Website:  https://paxfinancialgroup.com/

Connect with Roger:

Website:  https://www.sterlingfoundations.com

Facebook:  https://www.facebook.com/sterlingfoundations/

Twitter:  https://x.com/SterlingFndMgt?mx=2

LinkedIn:  https://www.linkedin.com/company/sterling-foundation-management-llc/

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Think tax strategy is just for April? Think again—this episode dives into how proactive planning, multi-state considerations, and personal client relationships can save businesses big and help them scale smarter.

In this episode of Sterling Insights, guest host Seth Krussman sits down with Joseph Witzig, a seasoned CPA and founder of a thriving multi-state advisory firm. Together, they explore the evolving tax and accounting landscape, sharing valuable insights and practical tips for listeners. Joseph draws from a diverse background—ranging from military intelligence to boutique accounting firms—to discuss the real challenges business owners face when navigating complex tax codes and growth. This episode is a must-listen for advisors, CPAs, and business owners, providing both knowledge and tools to navigate this critical but often overlooked subject.

Key Takeaways:

● 🧭 Proactive Planning Pays Off: Why forecasting taxes and financials in advance can make or break a business.
● 🗺️ Multi-State Blind Spots: How hiring remotely or expanding into new states can create unexpected tax liabilities.
● 💼 The S-Corp Decision: A deep dive into whether S-Corp status actually makes sense—and how to know for sure.
● 🤝 Human First, Virtual Second: Why hybrid accounting firms with in-person options are standing out in a remote-first world.
● 🧠 Experience Over Speed: Advice to aspiring CPAs on why waiting and gaining experience is the best foundation for starting your own firm.

Quotes from the Joseph:

● “We started the firm on the idea of being proactive—not just reacting to what already happened.”
● “One employee in another state can trigger tax filing requirements you never planned for.”
● “The balance sheet matters just as much as the P&L—if not more.”
🔗 Conclusion:
This episode highlights the power of proactive strategy, cross-state awareness, and personalized client service—offering a refreshing lens on what modern advisory firms can and should be doing to stay ahead.
Connect with Joseph Witzig:
Website:  https://www.witzigcpa.com/
LinkedIn:  https://www.linkedin.com/company/witzig-cpa?trk=public_profile_experience-group-header
With Your Guest Host Seth Krussman:
Seth Krussman is a seasoned financial advisor and partner at Brayshaw Financial Group, LLC, with over 30 years of experience in entrepreneurship, business development, and wealth management. A Registered Representative and Investment Advisor Representative with Osaic Wealth, Inc., Seth specializes in tax-efficient investment strategies, executive compensation, and succession planning for high-net-worth clients. Based in Hillsboro, Oregon, he is also the nationally recognized co-host of the radio show Money On Tap and an active community leader, husband, and father.
Connect with Seth:
Website:  https://www.brayshawfinancial.com/
Podcast:  https://www.brayshawfinancial.com/money-on-tap
Facebook:  https://www.facebook.com/3Dinvesting/
X:  https://x.com/BFG_LLC/New boost

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Most advisors say they integrate tax and investments — but what does it look like when tax strategy truly leads the planning process? This episode explores that intersection and how it transforms outcomes for high net worth families.
In this episode of Sterling Insights, Roger sits down with Matt Fitzsimmons, Managing Partner at The Watchman Group and a veteran in investment and tax-integrated planning. Together, they explore how forward-looking tax planning changes the way wealth is managed, sharing valuable insights and practical tips for listeners. Matt draws from his extensive experience to discuss challenges like liquidity events, charitable giving, and business exits, offering actionable advice for advisors serving high net worth and ultra-high net worth clients. This episode is a must-listen for RIAs and fiduciaries managing complex client needs, providing both knowledge and tools to navigate this important subject.

Key Takeaways:

● 🧾 Lead with Tax Strategy: Clients rarely ask for investment alpha — they ask for clarity on taxes. Tax-first planning drives real value.
● 💰 Donor-Advised Funds Done Right: Bundling 10 years of giving into one year can lead to massive, tangible tax savings.
● 🏢 Planning Before the Liquidity Event: Donating illiquid assets pre-sale can unlock six-figure tax savings that are otherwise lost.
● 🏘️ Why Real Estate Is Back: Distress in multifamily housing presents rare buying opportunities — if you know where to look.
● 📉 Tax Alpha with Market-Neutral Strategies: Advanced approaches like accelerating capital losses or ordinary loss-generating funds are reshaping how portfolios are managed for the wealthy.

Quotes from Matt Fitzsimmons:

● “Clients don’t walk in asking about private credit — they walk in asking how to save on taxes.”
● “People value a dollar of tax savings more than a dollar of investment gains.”
● “We’re not just building portfolios — we’re building strategies around life events, tax brackets, and long-term outcomes.”
🔗 Conclusion:
Forward-looking tax planning isn’t just an add-on — it’s a competitive advantage for advisors serving high net worth clients.
Connect with Matt:
Website:  https://www.watchmangroup.com/

Connect with Roger:Website:  https://www.sterlingfoundations.comFacebook:  https://www.facebook.com/sterlingfoundations/Twitter:  https://x.com/SterlingFndMgt?mx=2LinkedIn:  https://www.linkedin.com/company/sterling-foundation-management-llc/

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What if the key to explosive growth in your advisory firm isn’t more clients—but fewer of the right ones?

In this episode of Sterling Insights, Roger sits down with Jon Randall, founder of XFA and PhD in Performance Psychology who coaches top financial advisors across the U.S. Together, they explore how financial advisors can unlock scalable growth and profitability by identifying and removing hidden bottlenecks in their practice. Jon draws from decades of hands-on consulting experience to discuss why most advisors get stuck below the million-dollar ceiling—and how to break through it by focusing on revenue per client, team optimization, and ideal client acquisition.

This episode is a must-listen for growth-minded, AUM-based financial advisors who want to scale with intention, maximize profitability, and finally run their firms like CEOs.

Key Takeaways:

● 📈 Revenue per Client Matters: Advisors focused only on AUM miss the bigger picture—optimizing revenue per client is the true lever for growth.

● 🧠 Break the Comfort Habit: Most advisors resist change due to mental conditioning. Identifying this bias is the first step to scaling effectively.

● ⏳ Capacity is Your Real Constraint: Too many clients—especially unprofitable ones—clog growth. Solving this can unlock massive opportunity.

● 💼 Scaling Doesn’t Require a Giant Team: You can double or triple revenue by going deeper with top clients—not always by adding headcount.

● 💸 Profitability ≠ Big Revenue: Even Barron’s Top 100 firms struggle with margins. Smart segmentation and delegation are essential.

Quotes from Jon Randall:

● “It’s way more efficient to light money on fire in the parking lot than to work with unprofitable clients.”

● “Advisors hold onto low-revenue clients like a child holds onto a security blanket.”

● “Capacity issues aren’t just slowing you down—they’re suffocating your growth.”

🔗 Conclusion:

This episode offers a candid, expert look into the silent constraints sabotaging advisory firms—and how to fix them for lasting success.

Connect with Jon:

Website:  https://www.xfa.coach/

LinkedIn: https://www.linkedin.com/in/jonrandallcmc/

LinkedIn:  https://www.linkedin.com/company/xfa-coach/

Facebook:  https://www.facebook.com/XFA.COACH

Instagram:  https://www.instagram.com/xfa.coach

YouTube:  https://www.youtube.com/@xfacoach

Connect with Roger:

Website:  https://www.sterlingfoundations.com

Facebook:  https://www.facebook.com/sterlingfoundations/

Twitter:  https://x.com/SterlingFndMgt?mx=2

LinkedIn:  https://www.linkedin.com/company/sterling-foundation-management-llc/

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What if the biggest financial risks you face aren’t while building wealth—but when you start spending it?

In this episode of Sterling Insights, Roger sits down with Erik Brenner, CFP®, President & CEO of Hilltop Wealth and Tax Solutions. Together, they explore the complexities of transitioning from wealth accumulation to wealth distribution, sharing valuable insights and practical strategies for listeners. Erik draws from over 30 years of experience to discuss tax mitigation, retirement pitfalls, the Personal CFO model, and the challenges facing today’s high‑net‑worth families, offering actionable advice for anyone navigating the modern financial landscape. This episode is a must-listen for high‑net‑worth individuals, business owners, physicians, and advisors seeking deeper planning insights, providing both knowledge and tools to make smarter decisions on the way down the financial mountain.

Key Takeaways:

● 💼 Retirement Isn’t What It Used to Be: Today’s retirees face far more complexity—fewer pensions, more choices, and higher stakes.

● 🧭 The “Coming Down the Mountain” Risk: Most financial mistakes happen during the distribution phase, not the accumulation phase.

● 🧾 Tax Mitigation – Tax Planning: Erik explains why minimizing taxes this year—not deferring them—is essential for high-income and high‑net‑worth individuals.

● 🏛️ The Power of the Personal CFO Model: Comprehensive planning that integrates investments, tax, and estate strategy leads to better long-term outcomes.

● 🌅 Secure Act Changes Everything: New laws have reshaped inheritance, RMDs, and Roth strategy—making guidance more important than ever.

Quotes from Erik Brenner:

● “It’s not your parents’ or grandparents’ retirement anymore.”

● “Most deaths in mountain climbing happen on the way down—and financially, it’s no different.”

● “Tax mitigation means reducing tax today and never paying it back—not just kicking it down the road.”

🔗 Conclusion: Navigating wealth today requires more than investment management—it requires a coordinated, strategic Personal CFO guiding every major financial decision.

Connect with Erik:

Website: https://hilltopwealthtax.com/

LinkedIn: https://www.linkedin.com/in/erikbrenner/

LinkedIn:  https://www.linkedin.com/company/hilltopwealthtax/

Facebook: https://www.facebook.com/hilltopwealthtax

Instagram: https://www.instagram.com/hilltopwealthtax/

YouTube: https://www.youtube.com/@HilltopWealthTaxSolutions

Connect with Roger:

Website:  https://www.sterlingfoundations.com

Facebook:  https://www.facebook.com/sterlingfoundations/

Twitter:  https://x.com/SterlingFndMgt?mx=2

LinkedIn:  https://www.linkedin.com/company/sterling-foundation-management-llc/

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Think cost segregation is just for big-time developers? Think again. This episode reveals how one strategy can unlock massive tax savings—even for everyday real estate investors and medical professionals.

In this episode of Sterling Insights, guest host Charles Trakas sits down with David Wiener, CEO of Cash Flow Strategies and one of the top cost segregation experts in the country. Together, they explore how cost segregation, bonus depreciation, and R&D credits can significantly boost cash flow and reduce tax burdens, sharing valuable insights and practical tips for listeners. David draws from his extensive experience helping doctors, dentists, and real estate investors uncover hidden savings, offering actionable advice for financial advisors and high-net-worth clients seeking smarter tax strategies.
This episode is a must-listen for advisors, CPAs, real estate professionals, and investors—providing both knowledge and tools to navigate this powerful (and often misunderstood) strategy.

Key Takeaways:

● 💸 Cost Seg Isn’t Just for Commercial Giants: Even a single-family rental can qualify for this tax strategy.
● 🧱 Break Down the Building: Learn how to reclassify assets for faster depreciation—and bigger deductions.
● 🧾 Bonus Depreciation Is Back (And Permanent): The “Big Beautiful Bill” makes this a golden opportunity for real estate owners.
● 🧠 Avoid DIY Pitfalls: Cheap cost seg studies can cost you more in audits. Engineering-based reports are IRS-recommended.
● 🔬 R&D Credits Expanded: More industries (including IT) can now qualify—and the credits are available upfront.

Quotes from David Wiener:

● “It’s your money—keep more of it.”
● “You wouldn’t price shop for a brain surgeon. Why do it for your taxes?”
● “We’ve done 50,000+ studies and never triggered an audit.”
🔗 Conclusion:
Cost segregation isn’t just a tax tool—it’s a cash flow supercharger. Advisors and investors who understand it can unlock serious financial leverage.
Connect with David:
Website:  https://costsegregation.infoYouTube:  https://youtube.com/cashflowstrategiesincInstagram:  https://www.instagram.com/david.wiener
Connect with Charles Trakas:
Website:  https://proactivetaxreductions.com/about-us/ LinkedIn:https://www.linkedin.com/in/businessownertaxreductionadvisor/ Facebook Business:https://www.facebook.com/TrakasFinancial  Facebook Personal:https://www.facebook.com/profile.php?id=100011447285280

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