How I Navigated My First and Most Life-Changing Real Estate Deal

How I Navigated My First and Most Life-Changing Real Estate Deal

2 min read
Sterling White

Sterling White is a multifamily investor, specializing in value-add apartments in Indianapolis and other Midwestern markets. With just under a decade of experience in the real estate industry, Sterling was involved with the management of over $10MM in capital, which is deployed across a $18.9MM real estate portfolio made up of multifamily apartments. Through the company he founded, Sonder Investment Group, he owns just under 400 units.

Sterling is a seasoned real estate investor, philanthropist, speaker, host, mentor, and former world record attemptee, who was born and raised in Indianapolis. He is the author of the renowned book From Zero to 400 Units and the host of a phenomenal podcast, which hit the No. 1 spot on The Real Estate Experience Podcast‘s list of best shows in the investing category.

Living and breathing real estate since 2009, Sterling currently owns multiple businesses related to real estate, including Sterling White Enterprises, Sonder Investment Group, and other investment partnerships. Throughout the span of a decade, he has contributed to helping others become successful in the real estate industry. In addition, he has been directly involved with both buying and selling over 100 single family homes.

Sterling’s primary specialities include sales, marketing, crowdfunding, buy and hold investing, investment properties, and many more.

He was featured on the BiggerPockets Podcast episode #308 and has been contributing content to BiggerPockets since 2014, with over 200 posts on topics ranging from single family investing and apartment investing to mindset and scaling a business online. He has been featured on multiple other podcasts, too.

When he isn’t immersed in the real world, Sterling likes reading motivational books, including Maverick Mindset by Doug Hall, As a Man Thinketh by James Allen, and Sell or Be Sold by Grant Cardone.

As a thrill-seeker with an evident fear of heights, he somehow managed to jump off of a 65-foot cliff into deep water without flinching. (Okay, maybe a little bit…) Sterling is also an avid kale-eating traveller, but nothing is more important to him than family. His unusual habit is bird-watching, which he discovered he truly enjoyed during an Ornithology class from his college days.

Sterling attended the University of Indianapolis.

Instagram @sterlingwhiteofficial

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Is there a single property purchase that really changed things for you?

I know there was for me. I think we all have a pivotal real estate deal that we can point to that really changed the dynamics of our finances, mindset, and probably our lives as well.

More importantly, is there a common theme in this one critical deal that successful investors point to as being the game changer that others can learn from?

What was it—or what will it be—for you? The one with the biggest profit? The smoothest transaction? Biggest learning lesson from failure?

My Game-Changing Property Deal

For me it was definitely my first deal. It’s something I hear from other successful real estate investors too.

Most often it is because that first deal completely blows their minds, changes their perception, and provides insight to the power of investing in real estate. They gain a whole new appreciation for what’s possible. Then they are hooked for life.

It was a little different for me. My first deal allowed me to get over that analysis paralysis hurdle and learn so much through the process from managing contractors, leasing, property management, working with a title company to close transaction and negotiations. I learned so much more about what’s involved in the process than I knew was there. It gave me a ton of confidence to do more, and it showed me what was possible.

Related: Why Newbies Should Focus on the First Deal

I hear so many excuses for why people choose not to get started in real estate — even when they know the benefits and that they need it. I got started on the investing side with no money and at 22, which was only 6 years ago after working multiple years in construction. I had negative money in my bank account and bad credit. I overcame and solved those problems by leveraging someone else and helping them. The problem I solved for them was they couldn’t find a deal and had no time to do so.  

I structured the deal so that I retained a 10-percent equity stake instead of taking a simple wholesale fee. I thought long-term. The total purchase price was $25,000 cash, and an additional $25,000 was put into it. We rented it at $850. That property is now worth $100–$110k. In hindsight, I wish I bought a lot more during that time.  

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My Second-Most Important Deal

More recently I experienced another major game changing deal. I wouldn’t have gotten this far without the first single-family deal, but this also really changed my world. This was my first multifamily apartment building deal.

This again changed my understanding of money, the dynamics of real estate, and the economies of scale. Again I partnered up with some others for the funding, and have since steam rolled into focusing primarily on this new asset class.

Related: These 3 Simple Steps Will Prepare You For Your First Deal

Ways to Get Started

Maybe you haven’t gotten started yet. Maybe you’ve allowed yourself to be stuck with some of the same excuses, like not having enough money, credit, time, or knowledge.

Some ways to break in and do your first deal might include:

  • House hacking by buying a small multifamily to live in and rent out
  • Creative financing like lease options
  • Real estate wholesaling to build up your own investment capital for rentals
  • Partnering up with others
  • Investing in an experienced operators deal


My first deal will always be my most important. Although, there will be others that really help you make leaps, too. It can be easier than you think to get started if you apply a little creative problem solving.

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What was your most important deal?

What will you do to get started? Share with us below!

My first deal allowed taught me so much about what’s involved in the investing process than I knew even existed. It gave me a ton of confidence to do more, and it showed me what was possible!