CASE STUDY: THE REAL ESTATE INVESTOR
Managing Real Estate with Confidence.
After his first eight years of active real estate investing, Chris found a lot of success and his business grew faster than he ever imagined it would. He was burnt out and the growth wasn’t sustainable. Chris worked with Pillar to organize his finances and to simplify his newfound complexity.
*For privacy reasons, these case studies do not include real client details.
The Challenge
Chris came to us with an impressive but overwhelming real estate portfolio: 33 properties across flips, long-term rentals, and short-term vacation units. He had spent years building his wealth through real estate, and on paper, he was thriving. Each investment had its own structure, debt, and return profile, but the complexity was catching up with him.
Chris worked with a skilled CPA who kept his taxes in order, but he lacked a broader strategy. There was no single, integrated system to manage property performance, cash flow timing, or debt obligations. He found himself reacting rather than planning—juggling property management decisions, loan payments, and income inconsistency without a cohesive financial framework to guide him.
Renovations and vacancies made forecasting a challenge, so he lacked clarity. Chris wanted to understand how his properties worked together, how to optimize his cash flow, and how to create a plan that would allow him to step back from day-to-day operations without losing control of what he’d built.
That’s when he turned to Pillar Wealth to help organize the chaos and turn a successful real estate hustle into a sustainable financial strategy.
The Pillar Effect
Stabilize the Foundation
Pillar organized Chris’s cash flow, assets, liabilities, and tax burden into one central portal, and helped Chris get the right data to make high-quality business decisions.
Maximize Assets
The team coordinated with his CPA to ensure that he’s making the most out of his depreciation and business income to minimize his current and future tax liability. Pillar established a line of credit that can supplement cash-flow and also allows Chris to stay invested in the market.
Strategically Build
Pillar built a plan to maximize his current cash flow which allows Chris and his family to enjoy their current lifestyle while saving for the future. The team introduced him to an estate attorney to create a trust for his assets and ensured that he had the proper insurance coverages to protect his wealth.
The Results
A Customized
Team of Experts
Pillar assembled a team tailored to Chris’s unique needs, so he has trusted professionals in his corner without having to build the roster himself.
Freedom to Prioritize
the Work He Loves
With steady income from his real estate holdings, Chris now focuses on deals that energize him instead of constantly scrambling to stay afloat.
Ongoing Oversight, Minus the Headache
Pillar regularly reviews Chris’s holdings and keeps his balance sheet current, so he can stay informed without managing the details himself.
Are You Ready to
Rest on Pillar?
Our group of clients is affectionately referred to as “The 111.” We only work with 111 families at a time so that we can give each client the attention and high-level strategy they need.
Find out if you’re a good fit by contacting us using this form, or let us help evaluate your situation by answering questions to see where you land on our “Financial Complexity Scale."