Ask Tiffany H
Strategy. Real Estate. Public Impact.
I’m Tiffany L. Hollinger—Real estate investor, developer, Realtor, strategist, and the voice behind #AskTiffanyH. I help people turn knowledge into action, ideas into assets, and communities into legacies through real estate, strategy, and intentional outcomes.
Professional. A little sassy. Always strategic.
What I Do
I operate across the full real estate lifecycle—from acquisition to execution to education—while helping others do the same with clarity and confidence.
Real Estate Investing & Property Flips | Hollinger Financial
Acquiring, renovating, and repositioning residential properties with a focus on value creation and disciplined execution.
Real Estate Education | Flip Pro Academy
Teaching aspiring and emerging investors how to flip properties the right way—through structured systems, real numbers, and real accountability. ( FlipProAcademy.com / FlipToFortune.com )
Real Estate Development | Astraea Development
Leading ground-up and adaptive reuse projects focused on workforce housing, neighborhood stability, and long-term community impact.
Strategic Advisory & Public-Facing Strategy
Supporting developers, founders, and organizations with deal structure, partner alignment, and clear positioning for capital and public credibility.
Realtor | Berkshire Hathaway HomeServices Professional Realty
Guiding buyers, sellers, and investors with market expertise, strategic insight, and trusted representation.
My Approach
I believe development is more than buildings—it’s trust, structure, and stewardship.
- Clarity before capital – strong vision and alignment come first
- Disciplined execution – strategy that moves from paper to performance
- Community relevance – projects that respect place and people
- Long-term legacy – decisions that hold value beyond the deal
Why this works
Clarity keeps the strategy honest. Discipline keeps the work moving. Community keeps the impact real. And legacy? That’s the part nobody wants to talk about—until they do.
Featured Work
Selected platforms and initiatives that reflect how I operate across strategy, execution, and impact.
Astraea Development
Astraea Development focuses on intentional real estate projects that contribute to neighborhood stability, workforce housing, and long-term community value—starting in Cleveland, Ohio.
Hollinger Financial
Hollinger Financial is the platform through which I actively invest in and flip residential properties—applying the same discipline and standards I teach to others. In addition to manage a portfolio of rental properties.
Flip Pro Academy
Flip Pro Academy equips aspiring investors with the knowledge, tools, and confidence to flip properties sustainably—bridging the gap between theory and execution.
Why #AskTiffanyH
#AskTiffanyH began as a trusted space for real answers about money, property, and growth. Today, it represents a broader platform—where strategy meets experience and transparency builds trust.
People come to #AskTiffanyH for:
- Straightforward guidance
- Strategic perspective
- Real-world experience
- A partner who understands both vision and execution
Translation (because we’re being honest)
You’re not looking for hype—you’re looking for answers, a plan, and somebody who can see the whole board.
Let’s Build Something That Lasts
Real estate is rarely just one transaction—it’s a journey of decisions that shape wealth, stability, and legacy.
Whether you’re:
- Buying or selling a property
- Looking to invest or flip with confidence
- Seeking guidance as an emerging developer
- Exploring aligned partnerships or capital opportunities
- Or simply need a strategic conversation to get unstuck
I meet people where they are—and help them get to where they want to go.
The vibe
Bring the vision. Bring the questions. Bring the “I’m stuck.”
I’ll bring structure, strategy, and the next right move.
Plan. Protect. Prosper.
Because strategy without protection is just confidence… and I’m not here for preventable chaos.
Plan
The recent economic crisis in America has taught us that no matter if we are rich, poor, or somewhere in between, few are unaffected by market volatility. However, some fare better than others because having a plan is the key to success. ASK ME how to get your plan started today!
Protect
You work hard everyday to provide for your family and your future. But there are things that happen that we can't control - layoffs, stocks market dips, major house or car repairs, medical emergencies, etc. It's imperative to protect your family, your savings and your assets to ensure these events don't create undue hardships on your household. ASK ME how you can secure your family's financial future starting now.
Prosper
Very few people are born into wealth. Even few grow up instinctively knowing the most efficient and current effective techniques. Depending on your stage in life, there are a variety of tools that can be custom-fit to support your goals and resources. ASK ME how can leverage current tools, techniques and resources so they work for you to create the lifestyle your family deserves.
Contact
Tell me what you’re building — I’ll help you move with clarity and confidence.
Before you hit send…
Be specific. Be bold. Be honest. If it matters, say it.
(Yes, I read every message. No, I don’t do fluff.)
- Investing / Flips
- Development / Community Projects
- Education (Flip Pro Academy)
- Strategic Advisory
- Buying / Selling (Realtor)