I Wish I Knew Then What I Know Now – A Journey Towards a Better Life Through Actively and Passively Investing in Real Estate

I wish I knew then what I know now.  This is a statement everyone has thought of at one point or another.  I think about the person I was and how I perceived the world at different eras in my life. My experiences have shaped me into the person I’ve become. I expect this is true for everyone.  These experiences have affected my perception of risk and reward, which is directly tied to how I view money.  Each person’s path is unique and their journey influences their relationship with money and, ultimately, their investment approach.

This is my story from how I went from investing in stocks and bonds, to active real estate investor, and eventually passively investing in real estate.

Early in the Journey

Like many who enter college, I didn’t know what I wanted to be when I grew up.  A business degree seemed like a good start.  I majored in marketing.  I wish I knew then what I know now.  I would have likely majored in finance or economics if I truly knew what I would become passionate about later in life.

After graduating, I started a career in sales.  Very few people were getting jobs in marketing departments straight out of undergrad.  Makes sense.  You have to know your product and your customers before you can successfully market to your audience.  Bummer.  Looks like sales was my option.

I had some fun with my career path in my twenties and was successful.  I had some upward mobility opportunity and capitalized on it by moving where opportunities arose.  Each time I transitioned into a new role, as you’d expect, responsibility and expectations grew.  As the excitement of learning a role and adapting to new living surroundings wore-off, I found myself feeling hollow.  I wanted more in life.  I started realizing that the most important asset in life wasn’t money, but time.

A Flawed Strategy Emerges

By my mid-thirties I was working in the medical device space, selling capital equipment and implants to surgeons in the operating room.  Around that time, I had found the financial independence, retire early (FIRE) community and was absorbing everything I could.  The basic premise of FIRE is to increase your income, live frugally by cutting unnecessary expenses, and invest the rest.  The idea was not to live in deprivation, but truly spend your money on what matters to you and cut out the fluff.  Defining what matters is easier when you have a  strong “why”.  My “why” was to escape the rat race, to spend more time with my kids before they left home forever, and to be a more present father and husband.  I planned to achieve this by grinding in a high income job that didn’t fulfill me, saving money with ferocious discipline and investing the rest.  Then I would live off my principal by withdrawing based on the “4% rule.”

This went on for about seven years.  Saving diligently was paying off and dollar-cost averaging into a long bull market made investing look easy.  I was getting fairly close to my original goal of having our annual spending covered by withdrawing 4% of our principal every year.  I was also getting dangerously close to a mental breakdown from the stress of balancing 80 nights a year of travel, long workweeks, a busy home life, and little time for myself and my personal health.  I wondered how much longer I could grind it out.  I was putting off happiness in the present in hopes of achieving it sometime in the future.  I wish I knew then what I know now

I also started to get nervous about my strategy of “retiring” early.  What if I left work and then the market tanked, exposing me to “sequence of return risk”.  Suddenly, my nest egg might not be able to support our spending.  I looked at bonds as a possible solution.  Traditionally a 60/40 stock/bond split has been a way to decrease portfolio volatility and derive income.  However, because of a 40-year bond market bull run, interest rates were and continue to be ultra-low.  If rates began to rise, the value of the bonds would fall, which seemed more than likely to me.  Holding bonds to maturity would protect the principal, but at such low rates, the income derived would never allow me to reach my goal to escape corporate America.

An Old Dream Renewed

I had always been interested in real estate.  I wasn’t particularly handy and was intimidated by problems that could come up with maintenance and being taken advantage of by contractors.  I was concerned about managing tenants.  What if I was traveling for work and I got a call about a toilet?  I had always found a reason to not invest or get started.

However, as I approached the breaking point with my work/life balance, I decided I had to do something.  My risk tolerance would not allow me to sleep at night based on my original plan.  I needed an investment that paid steady income with the opportunity for appreciation.  And I had to live life for happiness, not for money.  I needed real estate.

I started to look at my investments through a different lens. My new strategy was to stay invested in stocks and use cash from credit lines to buy distressed real estate.  I would employ the BRRRR strategy – buy, rehab, rent, refinance, repeat.  If executed properly, I could theoretically recycle my capital indefinitely, and stack income paying rentals up over time.  Why had I let self-limiting doubt keep me from getting started with this sooner?  I wish I knew then what I know now.

Active Investing, Turned Business to Passive Investor

The first home I rehabbed was an REO property I had bought at auction for $55,000.  The project was a lesson from the school of hard knocks on how not to manage contractors.  A lot of things went wrong and a lot of problems arose that I didn’t have experience in dealing with.  But I survived.  After going over budget, I was all-in for $85,000 of my money.  I learned how to post listings and held an open house.  The property rented for $1,200 a month.  A few months later I had the property appraised at $145,000 and refinanced, getting all my $85,000 back and then some.

My confidence soared.  I had found a model that was scalable that would help me achieve my investing and, more importantly, my life goals.  The funny thing is, even though I ran into a number of headaches and things didn’t go quite as planned, I loved the whole process.  I was hungry for more.  After having similar success with two more houses, I made the decision to put in my notice of resignation with my company.  I remember thinking to myself, I wish I knew then what I know now.  I could have made this decision much sooner in life if I had just believed in myself and taken action.  The worst case scenario I created in my mind never came to pass.  I stopped thinking about what could go wrong and started to think about all that could go right.

As my investments turned into a business, I was looking for additional ways to make income and diversify.  I wanted to expand outside my market.  Diversifying geographically into Sun Belt markets where jobs and people were moving seemed like a worthwhile wave to ride.  Although, it would be very difficult to do it on my own.  As a solution, I discovered passively investing in real estate syndications.  This option could afford me most of the benefits of active investing, without most of the challenges.  Vetting operators and deals took some time, but if you find great sponsors, the returns on their investments can be very attractive.

Maybe you don’t have a passion for active real estate investing like I do, but understand that real estate is a powerful wealth builder.  I wish I knew then what I know now, as passively investing in real estate is a great alternative.  As I grow older and eventually retire, I will naturally slow down with active investing and put more money to work in passive real estate investments.

What I Know Now

It has been two years now since I left W-2 work.  Since then, I’ve accomplished things I didn’t think were possible a few short years ago.  If I had known then what I know now, I would have lived life for happiness and not for money.  Money will come when you are truly committed to what you are working towards.  I would have started much sooner on working to live and not living to work.  “Sunday blues” are a thing of the past.  I’m excited to get started with my day on Monday morning.  Sometimes taking a step back in your career can lead to bigger things down the line, I’ve learned.  Enjoying what I do every day now has me excited for bigger things than escaping the rat race for a beach.

I would encourage anyone who’s putting off taking a chance on something they’ve always been interested in to take small, daily action.  Whether it’s starting a business, developing a product, writing a blog, flipping a house, passively investing in real estate, or anything you’ve dreamed of for yourself….you never know where the journey may lead.  You’ll also never find out if you don’t get started.  I wish I knew that then, but I know now.  

Paul Shannon is a full-time active real estate investor, as well as a limited partner in a number of syndications.  Prior to leaving the corporate world, Paul worked for a medical device company, selling capital equipment to surgeons in the operating room.  After completing a few rehabs employing the “BRRRR method”, he saw scalability and more control over how he spent his time, and left to pursue real estate in 2019.  Since then, Paul has completed over a dozen rehabs on both single-family and multifamily properties.  He currently owns over 50 units in Indianapolis and Evansville, IN and is a limited partner in larger apartments and industrial properties across the US. You can connect with him at www.redhawkinvesting.com

Nothing on this website should be considered financial advice. Investing involves risks which you assume. It is your duty to do your own due diligence. Read all documents and agreements before signing or investing in anything. It is your duty to consult with your own legal, financial and tax advisors regarding any investment.

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.

Contact Us

Stay Connected!

Sign up to be notified of our latest articles and meeting announcements.

Stay Connected!

Sign up to be notified of our latest articles and meeting announcements.