CEO Quits His Job to Launch a Wholesaling Real Estate Empire

CEO Quits His Job to Launch a Wholesaling Real Estate Empire

4 min max read

If you've ever toyed with the idea of leaving your 9-to-5 grind to embrace entrepreneurship, then you're in for quite the enlightening story. In the world of business and investment, few ventures fuel the dream of financial freedom like wholesaling real estate. And who better to illustrate this journey than Matthew Simmons, a man who traded the CEO title of multiple successful businesses for his own wholesaling empire?

The Genesis of a Wholesaling Virtuoso

Matthew's narrative is not just inspiring but is a testament to the potential lying dormant in the real estate wholesaling sector. As a previous CEO of a vending machine company, a gym, and a one-day bathroom remodeling venture, he liquidated his stakes to venture into wholesaling.

So, buckle up as we dive deep into the mechanics of how he achieved an impressive $18,000 on his first go at a wholesale deal and how you too can catapult your income and kiss your W-2 goodbye.

First Success: A Knock on the Door of Opportunity

Matthew recollects one of his earliest encounters with wholesaling success, which commenced with obtaining a list of probate deals. Although direct mail — the traditional route of sending out postcards — yielded a scarce response, Matthew didn't falter. He escalated his strategy to door knocking, which presented a more intimate approach, targeting prospects he believed had potential.

This tactic led him to a property marred by an undesirable location but with a surprising turnkey status. The traditional formula for crafting a maximum allowable offer — subtracting repair costs from the after-repair value — suggested an offer of just $11,000. Despite reservations of possibly insulting the sellers with such a low bid, Matthew's transparency won over the family. They agreed to an easy, quick close at the proposed price.

Within no buyers' list to fall back on, Matthew turned to a real estate investment association meeting and hawked the deal, ending in a $29,000 sale. An impressive $18,000 gain from his introductory wholesaling endeavor.

Why Probate Deals Are a Gold Mine

Considering the myriad paths one could embark on within real estate, why did Matthew gravitate toward probate? The short answer is ROI; the more elaborate explanation involves market demographics and untapped potential.

"Allegheny County is one of the oldest counties in the country, and probate was very popular here in terms of volume and in terms of opportunity," Matthew explains.


The Ingredients to Wholesaling Success

Feeding into the meat of the matter, Matthew dives into the specifics of formulating an offer. It's a blend of assessing after-repair value (ARV), incorporating repair costs, and seasoning it with a 0.7 multiplier to account for profit, carrying, and closing costs. He narrates a scenario: "If the property's full renovated worth (ARV) is $100,000, subtracting repair costs and our investment spread gives us what our buyers are willing to pay."

The buyers of Matthew's deal were not seeking a flip potential but rental revenue. It's an illustration of how understanding buyer perspectives — whether flip or cashflow-focused — is pivotal in securing fruitful contracts.

From Physical Endurance to Entrepreneurial Resilience: The Business Acumen Behind Success

When probing into Matthew's ability to strike it big so swiftly, it emerges that his earlier business pursuits and personal discipline were crucial catalysts. From the recurring revenue of gym memberships to the passive income of vending machines, these experiences laid a foundation for Matthew's leap into wholesaling.

"I don't believe you can have one area of your life completely dialed in and have the others be a mess," Matthew articulates, indicating the fundamental role holistic commitment plays in burgeoning success. A strong proponent of 'how you do anything is how you do everything', Matthew's journey is an educational blueprint for aspirants.

The Greater Wholesaling Narrative

Matthew's foray into wholesaling is more than a tale of leaving a salaried life for an uncertain venture. It is a structured path to scaling up, choosing the cream of the crop for one’s investment portfolio, and laying the groundwork for retirement — a daily endeavor for Matthew and his wife.

Comparing the wholesaling gig to his previous ventures, he reaffirms the indisputable financial and lifestyle advantages it holds — no contest.

So whether you're sketching a blueprint for your business or nurturing dreams of financial liberation, Matthew Simmons is a testament to the transformative power of real estate wholesaling and the wealth of opportunity it unlocks.

Where to Follow Matthew's Journey

For those of you allured by Matthew Simmons's story and seeking mentorship or simply a dose of his business wisdom, you can find him sharing more nuggets of knowledge on social media @TheRealMatthewSimmons on Instagram or delve into the longer narrative form on his YouTube channel, Matthew Simmons.

He's on a mission not just to expand his wholesaling venture but to empower his community of 40 like-minded entrepreneurs in mastering the intertwine of business, personal development, and leadership — because in real estate wholesaling, the transaction is just the beginning of the story.

Benjy Nichols

About Benjy Nichols

Benjy has been a media specialist at DealMachine for the last 2.5 years. He produces, writes, shoots, and edits our media content for our member's DealMachine and Real Estate education.