Tianna Thompson: Business & Real Estate Tax Strategist

Using tax law to help clients leap ahead

MEET TODAY’S GUEST

Tianna Thompson

Meet Tianna Thompson, founder and principal of Leapers Connect Consultancy. Originally from Jamaica, Tianna now calls Jacksonville home, where she has established herself as a prominent business and real estate tax advisor. Since beginning her practice in 2016, she has built a reputation for helping clients navigate complex tax regulations across multiple states. In 2018, she formalized her expertise by founding Leapers Connect Consultancy, which operates from a base in San Marco while serving clients remotely nationwide.

What immediately strikes you when meeting Tianna is her rare combination of warmth and precision. Her clients describe her as exceptionally attentive—she listens with genuine care but tackles tax challenges with unwavering focus and determination. Behind her approachable demeanor lies a sharp analytical mind that constantly seeks creative solutions within the boundaries of tax law. Tianna's comprehensive understanding of complex tax codes is matched only by her resourcefulness in applying them to each client's unique situation. While she brings a personable touch to every interaction, her meticulous attention to detail ensures nothing falls through the cracks when advocating for her clients' financial interests.

Let’s explore the story behind Tianna Thompson, founder at Leapers Connect Consultancy.

Tianna Thompson, Founder at Leapers Connect Consultancy

Hey there!

You’re reading Jax Entrepreneur — a newsletter about small business owners and entrepreneurs in Jacksonville, FL. We all have our unique stories when it comes to owning our own businesses — and let’s be real — owning a business is quite a journey. I hope this content helps you reach new opportunities to grow your business. Let’s dive in.
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— Ashleigh Shim, Creator of Jax Entrepreneur & Owner of The Bareclaw Company | Commercial Real Estate Agent at PETRA

THE INTERVIEW

From Chemistry Labs to Tax Strategy:

Tianna Thompson's path to becoming a trusted tax advisor wasn't a straight line. "Initially when I was in Jamaica, my degree was in pre-med and applied chemistry," she reveals. When I first met Tianna, I could tell she was very sharp and intelligent. Then, when she said she was a pre-med student, I knew I was right about her!

Despite her scientific background, Tianna soon realized that medicine wasn't her calling—and the financial burden of medical school presented another significant hurdle.

Instead, Tianna found herself drawn to the world of business through her family's wholesale operation in Jamaica. Working alongside her father, who had transitioned from electrician to successful business owner, she absorbed crucial lessons that would later form the foundation of her consultancy. "I learned so much from my dad," she reflects. "Strategic pricing, managing debt and finances, handling disputes, and supervising employees—these were skills school couldn’t fully teach."

Rather than continuing in the family business, Tianna took these insights and began offering business management services as a freelancer for small business owners. This experience allowed her to develop her own approach to financial strategy while helping entrepreneurs navigate their challenges. By 2016, she had established her practice, eventually formalizing it as Leapers Connect Consultancy in 2018.

When asked why she chose this particular career path, Tianna's answer is refreshingly straightforward: "I wanted the freedom to choose the type of clients I want to work with." This selective approach has allowed her to build a diverse portfolio of clients across the United States, focusing primarily on businesses with employees that gross between $100,000 and $2 million annually.

Today, her expertise in leveraging tax law benefits clients across all fifty states. To name a few: Texas, Georgia, Florida, New Jersey, New York, Tennessee, and Pennsylvania. Her practice has even expanded internationally, serving foreign clients who need specialized tax guidance for their U.S. operations.

Tianna Thompson, Founder at Leapers Connect Consultancy

What do you like most about what you do?

When asked what she enjoys most about her work, Tianna's eyes light up. "I love the ability to use tax law and accounting rules to help clients strategically lower their tax liability so they have more money in their pockets," she explains. This isn't just about numbers for her—it's about creating tangible impact in her clients' lives and businesses.

She shares a story that perfectly illustrates this impact: "I had a client with a service-based business with employees who wasn't keeping track of his books. Based on his sales, he assumed he would be paying about $300,000 in taxes. Through careful analysis and strategic application of tax law, we were able to legally reduce that to about $160,000." The certainty in her voice is evident—not just for the savings, but for the opportunity to demonstrate how proper financial guidance can transform a business's outlook.

Unlike many in her field who have pivoted to subscription-based models, Tianna maintains a more personalized approach. "Everyone is selling a subscription service these days. I don't want to do that," she states firmly. "For me, it's about the results, not just the money—because the money naturally follows when you deliver results."

This results-first philosophy extends to her vision for the future. "I see myself becoming sort of a household name in this industry," she says with assurance. "Not as someone who just does data entry, but as an advisor who truly understands each client's unique situation." She aspires to build a company that's recognized and respected throughout the industry—a place where business owners and investors know they'll receive knowledgeable guidance tailored to their specific needs.

"Accountants often don't do well with marketing," she notes with honesty. But Tianna doesn't need flashy campaigns—her work speaks for itself through the success stories of clients who have benefited from her expertise. What sets her apart is her accessibility and commitment to being more than just a number-cruncher. She's a strategist who makes complex tax laws understandable and, more importantly, advantageous for her clients. She is incredibly good at putting herself out there to meet other professional in the industry through speaking engagements, one-on-one meetings, social gatherings, networking events, and meetups.

Tianna Thompson, Founder at Leapers Connect Consultancy

Building Meaningful Relationships: Tianna's Client Approach

Tianna doesn't view her practice as a volume business—it's about finding the right fit and building lasting relationships. Her client roster reveals a distinct pattern: typically professionals between 28 and 45 years old—mostly millennials who are establishing themselves professionally—alongside seasoned business owners with decades of experience.

"I know my clients through and through," Tianna emphasizes. "I know exactly where my clients are and who they are." This intimate knowledge isn't accidental; it's the result of a deliberate selection process she's refined over years.

What her clients share isn't necessarily an age bracket or industry—it's a mindset. "They're people with stable finances and employment who are serious about growing," she explains. "They may not have all the knowledge themselves, but they want someone they can build a relationship with long-term."

This relationship-centered approach begins before anyone signs on. Tianna offers a free 15-minute consultation as an initial touchpoint, but her evaluation process goes much deeper. She carefully reviews potential clients' prior year tax returns, provides preliminary advice, and ensures she gets face time—whether virtually or in person—to properly assess their situation.

"Sometimes it takes multiple appointments to fully understand someone's financial picture," she notes. "I'm completely honest about whether I think we're a good match or not." This candor extends to turning away potential clients when she believes they would be better served elsewhere—a practice that has earned her respect even among those she doesn't ultimately work with.

What truly distinguishes Tianna's approach is her willingness to invest time upfront. Where many advisors might rush to close a sale, she focuses on building the foundation for a productive partnership. This methodology naturally attracts clients who value expertise and relationship over the lowest possible price point—clients who understand that tax strategy is a journey rather than a transaction.

"My clients appreciate knowing that I'm thinking about their specific situation, not just applying a one-size-fits-all formula," she says. This personalized attention creates the kind of loyalty that has fueled her firm's growth primarily through referrals from satisfied clients who have experienced firsthand the difference her approach makes.

Some of the boldest decisions I’ve made is saying ‘no’ to a client when it’s not a good fit but still leaving them with something valuable. I never leave them empty handed and try to help in the best way possible.

Tianna Thompson, Founder at Leapers Connect Consultancy

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LOCATION, LOCATION, LOCATION

Tianna’s Take on Real Estate For Professional Services Businesses

  • Remote businesses having a physical office location is important to show business legitimacy

  • Physical offices establish credibility

  • Meeting a client in person is easier

  • Her office is in San Marco, near Downtown (Southbank) at 841 Prudential Dr 12th Floor, Jacksonville, FL 32207

  • Using a commercial realtor or referrals by colleagues in the same business can help with a property search

(Pictured: Professional Offices in Historic Livery Building at 220 E Forsyth St, Jacksonville, FL 32202)

Now, let’s get back to the story.

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Tianna Thompson, Founder at Leapers Connect Consultancy

Beyond Tax Strategy: Building Business Foundations

During a business consultation with Tianna, clients quickly discover her expertise extends far beyond tax planning. She's observed a common pattern among new companies: "Usually new companies don't have a written plan of action based on their goals," she notes. "If you don't have a plan of action, your business goals don't matter."

This pragmatic insight shapes her approach to consultations. Rather than focusing solely on tax implications, Tianna helps entrepreneurs create a solid foundation with clear, actionable steps tailored to their specific situation. "It's about figuring out where they are and where they need to be," she explains. "And that will be different for everybody."

Her services adapt to meet these varied needs—whether it's establishing proper bookkeeping systems, setting up a brick-and-mortar location, or implementing online remote services. This flexibility has allowed her to successfully guide diverse businesses, from grocery and convenience stores to auto shops and many others across various industries.

For Tianna, a successful consultation isn't just about addressing immediate concerns but building a roadmap that transforms aspirations into achievable milestones. This comprehensive approach ensures her clients aren't just tax-compliant but strategically positioned for sustainable growth.

If you don’t have a plan of action, your business goals don’t matter

Tianna Thompson, Founder at Leapers Connect Consultancy
MUST-KNOW INFO

Contact Tianna Thompson

Certifications & Licenses:

- Enrolled Agent (IRS)

- Certified Acceptance Agent (IRS)

- Real Estate License (Florida)

➡️ LinkTree

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➡️ Phone: (833) 968-5327

➡️ Website: https://leapersconnect.com/

➡️ Email: [email protected]

FRESH TAKES

Balancing Business and Life: A Personal Look
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I really enjoyed getting together with Tianna over dinner about her business endeavors. She is a great person and respectable business woman. I have to say she did an amazing job with me for 2024 tax season. She showed me that after all my worries about my business, investment, and real estate endeavors, I was not a lost cause when it came to filing!

Getting to know Tianna showed me that she maintains a deliberate approach to her personal time. "Sleep, eat, go to church, visit family," is what she’ll say when asked about personal time. This straightforward answer reveals a woman who shows gratitude for the simple things in life.

As our conversation concludes, Tianna offers a piece of spiritual wisdom that guides her own approach to business. She references 2 Timothy 2:17 from the Holy Bible as an encouragement to all entrepreneurs navigating the challenges of ownership. Her perspective on entrepreneurship comes with a refreshing reminder: "A lot of people who are in business forget that it is a choice, and they have a choice to work a traditional job if being in business isn't right for them."

This reference speaks to her grounded outlook. "You can't be controlled or fearful about your business," she emphasizes, leaving business owners with a final piece of advice: "Get clear, get calm." In these four simple words, Tianna distills what might be her most valuable offering—not just tax strategies or business plans, but a mindset that brings clarity to chaos and calm to the often turbulent world of entrepreneurship.

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