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The Night Owl Difference
1. Real Estate Tax Expertise That Goes Beyond Compliance
With advanced certifications and real-world investing experience, we specialize in the strategies most firms overlook — depreciation planning, 1031 exchanges, cost segregation, and entity structuring for investors.
2. Strategic Tax Guidance and Generational Wealth Building
We help clients stop reacting during tax season and start planning proactively — integrating tax, accounting, and investment strategy into one cohesive plan.
3. A Trusted Financial Partner for Long-Term Prosperity
You deserve a partner who understands your business and evolves with it. We deliver consistent communication, tailored strategies, and proactive guidance that grows with you.
About Our Firm
Night Owl Accounting & Tax was created from a personal realization: most small business owners and real estate investors aren’t failing because they lack drive — they’re overwhelmed by financial uncertainty.
Our founder, Jackie, began her accounting career 14 years ago and was first pulled into taxation while helping a family member resolve back tax issues.
What started as an act of service became a lifelong passion. She discovered that helping people find peace with the IRS — and then teaching them how to stay ahead — was deeply rewarding work.
That passion grew into Night Owl Accounting & Tax — a firm built to simplify the complex, empower clients with understanding, and replace financial stress with confidence.
“Every number tells a story — and when you understand that story, you can take control of your future.”
Our Services
Strategic Advisory for Real Estate Investors
We help real estate investors structure their business, protect profits, and minimize taxes through clear, proactive strategies built for growth.
Tax Preparation & Compliance
Accurate, strategic tax filing that keeps you compliant and ensures every return supports your long-term financial goals.
Real Estate Investing Specialty
From BRRRR to short-term rentals and capital gains management, we provide insight that comes from experience, not guesswork.
Tax Resolution
From audits to back taxes, we handle the IRS so you can focus on moving forward with confidence and peace of mind.
Bookkeeping
Clean, organized books that give you clarity and insight — so your numbers always tell the real story of your business.
Fractional CFO
Part-time CFO expertise to help you plan, forecast, and grow your business with confidence and financial control.
Why We Exist
Most accounting firms focus on data entry, forms, and deadlines. We focus on strategy.
We exist to bridge the gap between compliance and clarity — to help real estate investors and small business owners:
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Understand how taxes and entity structures affect long-term wealth
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Build proactive strategies to reduce taxes, grow cash flow, and create generational wealth
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Make confident decisions rooted in accurate, real-time financial data
At Night Owl, we don’t just record history — we help you write your financial future.
Our work is guided by three core principles:
Clarity
Simplicity and transparency create confidence.
Integrity
We do what’s right, always.
Strategy
Every number matters because every decision matters.
The Night Owl Process
Step 1: Discovery & Consultation
Free 20–30 minute consultation to understand your goals, pain points, and opportunities.
“We take time to understand where you are — and where you want to go.”
Step 2: Financial Review & Proposal
We review your current financials, entity setup, and tax returns — then provide a transparent proposal with clear pricing and deliverables.
“You’ll know exactly what we’ll handle — and what results to expect.”
Step 3: Setup &
Onboarding
We organize your financial systems and ensure your data is clean and accurate.
“We make sure everything is ready for strategy.”
Step 4: Strategy & Implementation
We move from reactive to proactive management — delivering planning sessions, financial dashboards, and reporting.
“We turn your numbers into clarity and your plan into progress.”
Step 5: Ongoing Support & Growth
We meet regularly to review results, refine strategies, and adapt as your business evolves.
“We don’t just work for you — we grow with you.”
Meet the Founder
Jackie, EA, CRETS, MSCTA, CTRS
Enrolled Agent | Certified Real Estate Tax Specialist | Main Street Certified Tax Advisor | Certified Tax Resolution Specialist
Jackie brings 14 years of experience in accounting, tax strategy, and business finance — including ownership in multiple small businesses and real estate investments. She’s also a partner and CFO of a trucking company, giving her firsthand insight into the challenges entrepreneurs face daily.
Her calm, methodical approach helps clients feel at ease, even when tackling complex tax and financial challenges.
When she’s not working with clients, Jackie enjoys traveling (especially cruises), crocheting, cooking, and spending time with her partner, children, and grandchildren at their peaceful country home surrounded by nature.
Ready to Bring Clarity to Your Finances?
You don’t need to face financial uncertainty alone. Whether you’re an investor, an entrepreneur, or a growing small business, we’ll help you turn confusion into confidence and build a strategy that lasts.
📍 Address: 45730 SD Hwy 44, Parker, SD 57053
📞 Phone: 605-799-5388
📧 Email: jackie@nightowltax.com
Preferred Contact: Email or schedule directly through Calendly.
