The CPA who leads with heart — and backs it with expertise.
I'm La'Keithia Caldwell, a CPA with over a decade of experience across government, public accounting, audit, and startup finance. But long before I understood balance sheets, I understood people. That has always been the foundation of everything I do.
I grew up in West Tennessee, where Southern hospitality wasn't a phrase — it was a way of life. The belief that every person deserves to be treated with care, seen, and sent away better than they arrived. I carry that with me into every client engagement at Wyn2It.
"If I can help one person see what's possible for their finances, that's the win. That's always been the win."
— La'Keithia Caldwell, CPA
Built from experience. Driven by purpose.
My path to founding Wyn2It wasn't a straight line — it was a decade-long education in what it means to lead with both precision and heart.
University of Tennessee at Chattanooga
Earned a degree in Accounting from UTC, where a foundation in numbers met a growing passion for understanding how finances shape people's lives and possibilities.
State Treasury — Budget Officer (3 years)
Managed public sector budgets at the state level, developing a deep understanding of financial oversight, compliance, and the discipline of working with large-scale numbers where accuracy isn't optional.
Tax Associate — CPA Firm (2.5 years)
Gained hands-on tax experience in a professional firm environment — learning not just how to file returns, but how to build strategy around them.
Auditor (4 years)
Four years in audit sharpened an already precise eye for financial detail — and built the kind of integrity-first approach that now defines every Wyn2It engagement.
Accounting Manager — Startups (4 years)
Led the full accounting function for high-growth startups, including successfully guiding a multi-million dollar company through a merger as the sole accountant. Added financial modeling, sales & use tax, tax resolution, and payroll to an already deep skill set.
Founder, Wyn2It — Boutique CPA Firm
All of it — the government discipline, the tax strategy, the audit precision, the startup agility — now lives inside a boutique firm built around one thing: your success. Based in Drexel Hill, PA, serving Greater Philadelphia & Delaware County in person, and clients virtually nationwide.
Why Wyn2It.
Wyn2It was built on a simple belief: that people deserve a financial partner who shows up for them — not just at tax time, but in the moments that matter. Someone who leads with warmth, speaks plainly, and genuinely invests in the outcome.
Over the years, Wyn2It has evolved — clarified by experience, sharpened by partnership, and ultimately returned to its core. Today it stands as a boutique CPA firm with a defined scope and an undivided focus: accounting, tax strategy, personal finance coaching, and business advisory. Done with intention. Done with care.
The name says it all. Whatever "it" is for you — stability, growth, freedom, clarity — we're here to win it with you.
My process starts with you.
Before I look at a single number, I want to understand the person behind them. Where you are. Where you want to go. What's getting in the way. That conversation — honest, unhurried, and judgment-free — is where every Wyn2It engagement begins.
I listen first
Your situation is unique. The advice should be too. I never start with assumptions.
I speak plainly
No jargon, no intimidation. Finance should feel empowering — not confusing.
I stay in it
I'm not a once-a-year CPA. I'm a partner who checks in, follows up, and celebrates your progress.
I hold the standard
Warmth doesn't mean easy. I'll push back when it matters and hold you accountable — because that's what a real partner does.
The expertise behind the relationship.
Tax resolution services
- Offer in compromise — negotiate settlement of tax debt for less than the full amount owed
- State tax levy resolution — working directly with states to address and resolve tax levies
- Federal & state payment plans — establishing manageable installment agreements with the IRS and state agencies
Ready to work with someone who's actually in your corner?
Let's start with a conversation. No pressure, no pitch — just an honest look at where you are and how Wyn2It can help you get where you're going.
Book a consultation →