iTValuations Webinar Recap with Greg Northrop (iTvaluations) and Becky Brown (Stride Services)
For too many business owners, tax season brings more than a deadline. A larger-than-expected bill. A sudden cash flow crunch. Or worse—a cycle of playing catch-up that bleeds into the next year.
In this recent iTvaluations webinar, Greg Northrop, Managing Partner at IT Tax Advisors, and Becky Brown of Stride Services shared practical, proactive ways IT firms and MSPs can eliminate tax season surprises. From keeping your books clean to getting ahead of your quarterly estimates, they covered what it really looks like to stay in control of your tax strategy all year long.
Whether you’re navigating Q2 or simply trying to make smarter financial decisions before year-end, here’s what to take away from the conversation.
Why the “April Tax Surprise” Happens
Greg opened the conversation with a reality he sees every year: business owners who find out—too late—that they owe more in taxes than expected.
“Every tax season, there’s at least one client I have to call and deliver bad news,” he said. “It’s not because they did anything wrong. It’s usually because there was no real understanding of the numbers that were leading to the liability.”
When you’re not tracking accurate financial data month-to-month, you lose the opportunity to plan. And when the only time you talk about taxes is after the fact, it’s already too late to course-correct.
Tax Planning Isn’t a Once-a-Year Task
Becky pointed out that many business owners mentally check out after tax season, thinking they don’t have to revisit it until next year. But that’s where the problem begins.
“You can’t do anything in April of 2026 to impact your 2025 tax return,” she said. “You have nine months left in the year—this is the time to act.”
Her advice? Don’t delay. Start with 2025. Clean up January through April, make sure your books are accurate, and get into a monthly or at least quarterly cadence with your financials.
3 Ways to Stay Ahead of Tax Season
1. Close Your Books Monthly
Becky and Greg were both clear: if your books aren’t being closed monthly, you’re flying blind.
“A tax return should just be putting numbers on a piece of paper,” Becky said. “If you’re closing your books monthly, December is just another month.”
Greg added that messy books lead to missed insights—and unnecessary surprises. Many clients receive adjusting journal entries during tax season, but never apply them, so the same errors come back the next year.
“It’s garbage in, garbage out,” he said. “And if your books are off, we can’t give good advice.”
2. Get Real Numbers for Quarterly Estimates
Too many business owners rely on estimates based on last year’s numbers. That creates a situation where they either drastically overpay—or underpay and end up with a large bill.
“I’ve seen people get a $20,000 refund,” Becky said. “That’s a free loan to the IRS. That’s cash you could have used to grow your business.”
Instead, she recommends getting an updated estimate each quarter based on your actual numbers.
3. Don’t Skip the Balance Sheet
Becky shared how often business owners think their books are “fine” because the P&L looks good. But then you glance at the balance sheet—and it’s a mess.
“If there are negative numbers, outdated liabilities, or accounts from 2009—you’re not in good shape,” she said. “You can’t make decisions off financials you can’t explain.”
Greg agreed, noting that a lot of business owners don’t realize how much clarity (or confusion) their financials create—especially when it comes time to apply for financing, make a major hire, or prep for an acquisition.
Clean Books Aren’t Just About Taxes
Yes, accurate financials help with tax prep. But they also give you better visibility into how your business is really doing.
“You can use your data to figure out: Am I charging enough? Are my engagements profitable? What’s my ROI on marketing?” Becky explained. “If you’re going to do the work of accounting, make sure you’re getting value from it—not just compliance.”
Greg also emphasized the value of clean books when you’re preparing for a sale or applying for a loan:
“Your financials are your first impression,” he said. “Buyers and banks are going to want to see the story your numbers tell—and that story needs to line up with what you’re saying.”
Bonus Advice: Eliminate AR
Becky closed the conversation with a bold piece of advice: Stop chasing payments.
“There’s no reason MSPs should have accounts receivable,” she said. “Put a payment portal in place, get auto-pay into your agreements, and stop waiting for checks.”
She even offered a simple tactic for shifting client behavior:
“Tell them you’re going to start charging a $25 processing fee for checks. That usually does the trick.”
Common Tax Season Trends and Challenges
Greg shared a few trends that stood out during this tax season:
- The R&D Credit remains relevant but harder to access because of new amortization requirements
- Profit margins are being squeezed across the industry due to economic pressure and delayed sales cycles
- Cash flow is tight for many MSPs, which makes smart planning around quarterly tax payments even more critical
Becky also pointed out a new challenge: misinformation.
“More clients are showing up with tax strategies they saw on TikTok,” she said. “They want to deduct a car they bought, or they’ve heard about tricks that don’t apply to their situation. Too much advice with too little context can cause real problems.”
If You’re Not Sure Where to Start…
The last part of the conversation focused on what to do if you know your books need help—but you don’t know how to get started.
Greg and Becky both suggested starting with something simple:
- Add a payment portal
- Automate more of your billing or categorization in QuickBooks
- Talk to a professional to help you set up systems the right way
“It’s like hiring someone to clean your house,” Becky said. “You walk back in and everything’s in place—and you didn’t have to do the work.”
Final Thoughts
Clean books, consistent systems, and regular conversations with your CPA won’t just help you during tax season. They’ll make your business stronger across the board. Whether you’re trying to improve profitability, reduce stress, or get ready for a future transaction, it all starts with knowing your numbers—and trusting them.
🎥 Want to watch the full conversation?
This Stride Live Webinar is hosted by Stride Services. Stride is a comprehensive financial solutions provider, specializing in outsourced bookkeeping, accounting, tax, and advisory services for Managed Service Providers.
If you’re interested in being a featured guest on our Live Webinars or if there’s a subject matter expert you’d like us to interview, please let us know!
Show Notes + Transcript:
Becky Brown: Email
Becky Brown: LinkedIn
About iTV & IT Tax Advisors
iTvaluations is a business transformation and valuation firm helping IT service companies plan for growth, transactions, and value creation. IT Tax Advisors provides specialized tax services tailored to the needs of MSPs, VARs, and technology firms.
To learn more, visit www.itvaluations.com.
About Stride Services
Stride Services is a comprehensive financial partner for MSPs, providing outsourced bookkeeping, tax, and advisory services designed to improve clarity, support confident decision-making, and eliminate financial fire drills. Whether you need monthly accounting support or proactive tax guidance, Stride helps you stay on track and plan for what’s next.
To learn more, visit www.stride.services.
