Life by Design: Real Estate Investing with Good Egg’s Annie Dickerson

 

In a recent episode of the Passive Investing from Left Field podcast, Jim Pfeifer sits down with real estate expert Annie Dickerson, co-founder of Good Egg Investments, to discuss the transformative power of passive income and life by design. Real estate investing has long been touted as a path to financial freedom, but for many, the idea of actively managing properties can be daunting. Enter passive real estate investing through syndications – a method that allows individuals to invest in large-scale real estate projects without the hands-on management typically associated with property ownership. In a recent podcast episode, Annie Dickerson, co-founder of Good Egg Investments, shared her journey and insights into this powerful investment strategy.

From Teacher to Real Estate Mogul

Annie’s story begins in an unlikely place – the classroom. As a teacher with Teach for America, she quickly realized that her passion for education wasn’t aligned with her financial goals. “The paycheck doesn’t always align with the work that you do,” Annie reflects. This realization set her on a path to explore alternative ways of building wealth.

Her entry into real estate came through a fortuitous encounter with a savvy realtor who suggested buying a duplex instead of a single-family home. This advice led Annie and her husband to start what she playfully calls “real-life Monopoly,” accumulating properties one by one. However, as their family grew, they realized that active property management wasn’t sustainable with young children.

The “Easy Button” of Real Estate Investing

Annie’s journey took a significant turn when she discovered real estate syndications. She describes this moment as finding the “Easy Button” for real estate investing. “Nobody ever showed me the Easy Button,” Annie says, expressing her initial frustration at not knowing about this option earlier. This discovery not only changed her investment strategy but also inspired her to educate others about the possibilities of passive real estate investing.

Life by Design vs. Life by Default

One of the most compelling concepts Annie introduces is the idea of “Life by Design” as opposed to “Life by Default.” She explains, “Life by Design looks completely different for everybody. Some might want to stay home with their kids; another person might want to quit their job for six months and travel the world; and  another person might want to retire early and travel full-time.”

This philosophy underpins Annie’s approach to investing and her work with Good Egg Investments. She sees real estate as a tool to create multiple streams of income, allowing individuals to shape their lives according to their desires rather than defaulting to societal expectations.

The Importance of Education and Community

Annie emphasizes the value of education and community in the real estate investing world. She notes that many people are intimidated by the jargon and complexity of real estate syndications. However, she encourages newcomers to lean on the supportive community of experienced investors willing to share their knowledge.

“If you’re new in this space, you’re not alone,” Annie reassures. “There are people willing to help because these are all seekers, people who step outside the norm and they’re looking for something more.”

Vetting Sponsors and Deals

For those looking to invest in syndications, Annie offers valuable advice on vetting sponsors and deals. She stresses the importance of not just looking at track records but also evaluating communication styles and values alignment.

“I want to know not only the deals that they’ve done but how did those deals ultimately fare, and what did their communications with their investors look like throughout the lifecycle of that project,” Annie explains. She advises investors to ask questions and pay attention to how sponsors respond, as this can indicate how they’ll handle challenges down the road.

Navigating Market Challenges

Annie acknowledges the current challenges in the real estate market but maintains an optimistic outlook. She advises investors and operators to be flexible and look for opportunities in new areas or asset classes. For example, Good Egg Investments has expanded its focus to include emerging markets and different property types to find value in a shifting landscape.

The Critical Role of Communication

Perhaps the most emphasized point throughout the discussion is the paramount importance of communication in real estate partnerships. Annie draws a powerful analogy to air travel:

“We’ve all been on an airplane before and there’s turbulence that hits. What you want during that time is for the captain to come on and say, ‘Folks, this is no problem. We’ve hit a little bit of turbulence. Just buckle up, sit back. We’re going to find some smoother air here in just a moment.'”

She contrasts this with the anxiety-inducing scenario of a silent cockpit or a panicking pilot. This analogy perfectly encapsulates the experience of investors during market turbulence or when deals face challenges.

Annie shares a personal example of how Good Egg Investments handled a situation where a loan was coming due, but property values had decreased. They communicated with investors for months in advance, explaining the situation, outlining their efforts to address it, and keeping everyone informed of progress and setbacks. This level of transparency, while not guaranteeing investor happiness, builds trust and partnership.

Handling Capital Calls and Distributions

The discussion touches on the sensitive topics of capital calls and withheld distributions. Annie views these as sometimes necessary tools to protect investments, but stresses that how they’re communicated makes all the difference.

“If you communicate effectively, it lessens the pain so much,” she notes. Investors are more likely to participate in a capital call if they understand the reasoning behind it and have been kept informed throughout the process. Conversely, surprise announcements or lack of communication can erode trust and potentially lose investors.

Lessons for Operators and Investors

The insights shared in this podcast offer valuable lessons for both real estate operators and investors:

  1. Prioritize clear, consistent communication, especially during challenging times.
  2. Be transparent about both positive developments and potential issues.
  3. Educate investors about the investment process and potential scenarios.
  4. Foster a sense of partnership with investors rather than treating them as mere capital sources.
  5. Be flexible and adaptable in changing market conditions.
  6. Focus on building long-term relationships based on trust and shared values.

The Future of Passive Real Estate Investing

Despite current market challenges, Annie remains optimistic about the future of passive real estate investing. She sees opportunities for those willing to adapt, look deeper, and think creatively. The key, she believes, is in building strong partnerships, maintaining open communication, and always keeping the end goal in mind – helping investors achieve their unique vision of a life by design.

Passive real estate investing through syndications offers a powerful tool for building wealth and achieving financial freedom. However, as Annie Dickerson’s insights reveal, success in this field requires more than just capital. It demands education, careful vetting of partners, clear communication, and a commitment to transparency.

For those looking to enter the world of passive real estate investing, Annie’s journey and advice provide a valuable roadmap. By focusing on building strong partnerships, maintaining open lines of communication, and always keeping the end goal in sight, investors can navigate the complexities of real estate syndications and work towards their own “life by design.”

Whether you’re a seasoned investor or just starting to explore passive real estate opportunities, the lessons shared in this podcast serve as a reminder of the importance of due diligence, continuous learning, and the power of community in achieving investment success. As the real estate market continues to evolve, those who embrace these principles will be best positioned to thrive and turn their financial dreams into reality.

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This article is for educational purposes only and is not to be relied upon as the basis for entering into any transaction or advisory relationship or making any investment decision. All investments involve the risk of loss, including the loss of principal. Past performance, and any performance results reflected in this article, is not an indication of future results.

Chris Franckhauser

Vice President of Strategy & Growth, Advisory Partner

Chris Franckhauser, Vice President of Strategy & Growth, Advisory Partner for Left Field Investors, has been involved in real estate since 2008. He started with one single-family fix and flip, and he was hooked. He then scaled, completing five more over a brief period. While he enjoyed the journey and the financial tailwinds that came with each completed project, being an active investor with a W2 at the time, became too much to manage with a young and growing family. Seeing this was not easily scalable or sustainable long term, he searched for alternative ideas on where to invest. He explored other passive income streams but kept coming back to his two passions; real estate and time with his family. He discovered syndications after reconnecting with a former colleague and LFI Founder. He joined Left Field Investors in 2023 and has quickly immersed himself into the community and as a key member of our team.  

Chris earned a B.S. from The Ohio State University. After years in healthcare technology and medical devices, from startups to Fortune 15 companies, Chris shifted his efforts to consulting and owning a small apparel business when he is not working with LFI (Left Field Investors) or on his personal passive investments. A few years ago, Chris and his family left the cold life in Ohio for lake life in the Carolinas. Chris lives in Tega Cay, South Carolina with his wife and two kids. In his free time, he enjoys exploring all the things the Carolinas offer, from the beaches to the mountains and everywhere in between, volunteering at the school, coaching his kids’ sports teams and cheering on the Buckeyes from afar.  

Chris knows investing is a team sport. Being a strategic thinker and analytical by nature, the ability to collaborate with like-minded individuals in the Left Field Community and other communities is invaluable.  

Jim Pfeifer

President, Chief Executive Officer, Founder

Jim Pfeifer is one of the founders of Left Field Investors and the host of the Passive Investing from Left Field podcast. Left Field Investors is a group dedicated to educating and assisting like-minded investors negotiate the nuances of the passive investing landscape and world of syndications. Jim is a former financial advisor who became frustrated with the one-path-fits-all approach of the standard financial services industry. Jim now concentrates on investing in real assets that produce cash flow and is committed to sharing his knowledge with others who are interested in learning a different way to grow wealth.

Jim not only advises and helps people get started in passive real estate syndications, he also invests alongside them in small groups to allow for diversification among multiple investments and syndication sponsors. Jim believes the most important factor in a successful syndication is finding a sponsor that he knows, likes and trusts.

He has invested in over 100 passive syndications including apartments, mobile homes, self-storage, private lending and notes, ATM’s, commercial and industrial triple net leases, assisted living facilities and international coffee farms and cacao producers. Jim is constantly looking for new investment ideas that match his philosophy of real assets producing cash flow as well as looking for new sponsors with whom he can build quality, long-term relationships. Jim earned a degree in Finance & Marketing from the University of Oregon and a Master’s in Business Education from The Ohio State University. He has worked as a reinsurance underwriter, high school finance teacher, financial advisor and now works exclusively as a full-time passive investor. Jim lives in Dublin, Ohio with his wife, three kids and two dogs. In his free time, he loves to ski, play Ultimate frisbee and cheer on the Buckeyes.

Jim earned a degree in Finance & Marketing from the University of Oregon and a Master’s in Business Education from The Ohio State University. He has worked as a reinsurance underwriter, high school finance teacher, financial advisor and now works exclusively as a full-time passive investor. Jim lives in Dublin, Ohio with his wife, three kids and two dogs. In his free time, he loves to ski, play Ultimate frisbee and cheer on the Buckeyes.

Chad Ackerman

Chief Operating Officer, Founder

Chad is the Founder & Chief Operating Officer of Left Field Investors and the host of the LFI Spotlight podcast. Chad was in banking most of his career with a focus on data analytics, but in March of 2023 he left his W2 to become LFI’s second full time employee.

Chad always had a passion for real estate, so his analytics skills translated well into the deal analyzer side of the business. Through his training, education and networking Chad was able to align his passive investing to compliment his involvement with LFI while allowing him to grow his wealth and take steps towards financial freedom. He has appreciated the help he’s received from others along his journey which is why he is excited to host the LFI Spotlight podcast and share the experience of other investors and industry experts to assist those that are looking for education for their own journey.

Chad has a Bachelor’s Degree in Business with a Minor in Real Estate from the University of Cincinnati. He is working to educate his two teenagers in the passive investing world. In his spare time he likes to golf, kayak, and check out the local brewery scene.

Ryan Steig

Chief Financial Officer, Founder

Ryan Stieg started down the path of passive investing like many of us did, after he picked up a little purple book called Rich Dad, Poor Dad. The problem was that he did that in college and didn’t take action to start investing passively until many years later when that itch to invest passively crept back up.

Ryan became an accidental landlord after moving from Phoenix back to Montana in 2007, a rental he kept until 2016 when he started investing more intentionally. Since 2016, Ryan has focused (or should we say lack thereof) on all different kinds of investing, always returning to real estate and business as his mainstay. Ryan has a small portfolio of one-to-three-unit rentals across four different markets in the US. He has also invested in over fifty real estate syndication investments individually or with an investment group or tribe. Working to diversify in multiple asset classes, Ryan invests in multi-family, note funds, NNN industrial, retail, office, self-storage, online businesses, start-ups, and several other asset classes that further cement his self-diagnosis of “shiny object syndrome”.

However, with all of those reaches over the years, Ryan still believes in the long-term success and tenets of passive, cash-flow-focused investing with proven syndicators and shared knowledge in investing.

When he’s not working with LFI or on his personal passive investments, he recently opened a new Club Pilates franchise studio after an insurance career. Outside of that, he can be found with his wife watching whatever sport one of their two boys is involved in during that particular season.

Steve Suh

Chief Content Officer, Founder

Steve Suh, one of the founders of Left Field Investors and its Chief Content Officer, has been involved with real estate and alternative assets since 2005. Like many, he saw his net worth plummet during the two major stock market crashes in the early 2000s. Since then, he vowed to find other ways to invest his money. Reading Rich Dad, Poor Dad gave Steve the impetus to learn about real estate investing. He first became a landlord after purchasing his office condo. He then invested passively as a limited partner in oil and gas drilling syndications but quickly learned the importance of scrutinizing sponsors when he stopped getting returns after only a few months. Steve came back to real estate by buying a few small residential rentals. Seeing that this was not easily scalable, he searched for alternative ideas. After listening to hundreds of podcasts and attending numerous real estate investing meetings, he determined that passively investing in real estate syndications was the best avenue to get great, risk-adjusted returns. He has invested in dozens of syndications involving apartment buildings, self-storage facilities, resort properties, ATMs, Bitcoin mining funds, car washes, a coffee farm, and even a Broadway show.

When Steve is not vetting commercial real estate syndications in the evenings, he is stomping out eye diseases and improving vision during the day as an ophthalmologist. He enjoys playing in his tennis and pickleball leagues and rooting for his Buckeyes and Steelers football teams. In the past several years, he took up running and has completed three full marathons, including the New York City Marathon. He is always on a quest to find great pizza, BBQ brisket, and bourbon. He enjoys traveling with his wife and their three adult kids. They usually go on a medical mission trip once a year to southern Mexico to provide eye surgeries and glasses to the residents. Steve has enjoyed being a part of Left Field Investors to help others learn about the merits of passive, real asset investments.

Sean Donnelly

Chief Culture Officer, Founder

Sean holds a W2 job in the finance sector and began his real estate investing journey shortly after earning his MBA. Unfortunately, it could not have begun at a worse time … anyone remember 2007 … but even the recession provided worthy lessons. Sean stayed in the game continuing to find his place, progressing from flipping to owning single and multi-family rentals to now funding opportunities through syndications. While Sean is still heavily invested in the equities market and holds a small portfolio of rentals, he strongly believes passive investing is the best way to offset the cyclical nature of traditional investment vehicles as well as avoid the headaches of direct property ownership. Through consistent cash flow, long term yield and available tax benefits, the diversification offered with passive investing brings a welcomed balance to an otherwise turbulent investing scheme. What Sean likes most about the syndication space is that the investment opportunities are not “one size fits all” and the community of investors genuinely want to help.

He earned a B.S. in Finance from Iowa State University in 1995 and a MBA from Otterbein University in 2007. Sean has lived in eight states but has called Ohio home for the last 20+.  When not attending his children’s various school/sporting events, Sean can be found running, golfing, shooting or fly-fishing.

Patrick Wills

Chief Information Officer, Advisory Partner

An active real estate investor since 2017, Patrick Wills’ investing journey began like many others – after reading the “purple book” by Robert Kiyosaki. Patrick started with single family rentals, and while they performed well, he quickly realized their inability to scale efficiently while remaining passive. He discovered syndications via podcasts and local meetups and never looked back. He joined Left Field Investors in 2022 as a member and has quickly become an integral part of the team as Vice President of Technology.

An I.T. Systems Engineer by trade, he experienced the limitations of traditional Wall Street investing firsthand in his career and knew there had to be a better way to truly have financial freedom.

Unfortunately, that better way is inaccessible to those who need it most. His mission is to make alternative investments accessible to everyone who seeks to take control of their financial future and to pursue their passions in life.

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