From the Beardstown Ladies & the Boston Mob to Syndications – An Investor’s Story

My investing journey started a little later than most. As a medical resident in my late twenties, I had spent the first two decades plus of my life accumulating debt. I was thrilled to be at the time of my life where I was actually earning a paycheck and had a small amount of money to invest. 

Conventional Investing

I immersed myself in the teachings of Suze Orman, Jean Chatsky, Dave Ramsey, the Beardstown Ladies, and the Motley Fool. I became convinced that the only way to retirement riches was through investing in the stock market. I truly believed that through accumulating a broad portfolio of mutual funds and setting it on autopilot, one was guaranteed to be a millionaire in no time.

I voraciously paid down my student loans but managed to squirrel away a little bit out of every paycheck to invest in the stock market. I began to see the fruits of my labor pay off as I began to amass a small, but not insubstantial, portfolio. The late 1990s were good for equities with double-digit returns every year. It seemed like each year compounded upon the last, and there was no place for the markets to go but up – then the year 2000 hit.

My tech-heavy portfolio was sliced in half in less than six months. I was devastated. As Mike Tyson said, “Everyone has a plan… until they get punched in the mouth.” I was punched hard.   Regardless, I had faith in the gospel preached by Suze, The Motley Fool, and the Beardstown Ladies. Long-term investment in a core portfolio of stocks was the way to wealth and periodic declines of 50% were not only normal, but great news because they represented BUYING OPPORTUNITIES!!!  Unfortunately, my colleagues who were one to two years away from their retirements did not see this decline in the same light. I got used to seeing their sullen faces at work every day shaking their heads saying, “Well, I got ten more years of this now.”

My Start Into Single-Family Homes

The market did eventually rebound, and I seemed to acquire some sort of amnesia surrounding 1999. I was looking for a place to invest that did not involve the wild swings of the stock market.  My “smart money” friends were urging me to invest in single-family rental properties.  In 2007, the housing market was on a tear, and I was developing serious FOMO after hearing of my colleagues’ 20% month-on-month appreciation in markets like Las Vegas and coastal Florida. I eventually pulled the trigger, sold some stocks, and invested in an attractive bungalow on the coast of Maine. How idyllic! 

The Dream Tenant

My first tenant was what one would call a “dream tenant”. He was a locally employed engineer with a charming family. If something needed to be fixed, he would take care of it and subtract the cost of supplies off his rent. He maintained the lawn himself because he truly enjoyed doing yard work. Everything was good. 

Then one day I got a call from him. Apparently, the entire roof over the living room was sagging in. I went to take a look at it and sure enough the entire roof was bowing inward and looked like it was en route to collapsing. We had a roofing contractor inspect it and were shocked to discover that there was major structural damage that was missed on the building inspection. The entire roof including the eaves would need to be completely rebuilt. So much for my positive cash flow…  

In 2009 sadly our dream tenant announced to us that he would be ending his lease as he accepted a job transfer across the country. We considered selling the property, but unfortunately the home’s assessed value had been cut nearly in half due to the financial meltdown and its subsequent decimation of residential real estate.  We decided to ride out the storm and try to find a new tenant.  

The (In)famous New Tenant

After a short search, we felt as if we found our replacement. He was a soft-spoken, middle-aged gentleman who claimed that he had a terminal illness and wanted to spend his last couple of years on the Maine coast. He was adamant that we provide him with privacy and he not be disturbed so as to provide him with peace in his terminal state. I could not think of a better tenant. It felt good to provide this gentleman with a peaceful place to find solace in his final years. I did a background check and was unable to find any red flags on him. Shortly after he moved in, however, the issues began. 

In retrospect, the first thing that should have raised my suspicions was the fact he did not have an email address. His explanation was “I hate computers and I hate technology. I like pen and paper! What is wrong with good old-fashioned pen and paper?!“  Fair enough. Next was his insistence that he pay each month’s rent in paper bills. I asked why he couldn’t just write me a check? After all, schlepping $2000 in bills to the bank every month was somewhat of a nuisance. He told me that he couldn’t provide a check because he didn’t have a bank account. He didn’t trust the banking system so he preferred to keep everything in cash. My patience was starting to run thin. 

One day I stopped by the house and discovered that it reeked of cigarette smoke. I found it somewhat odd that someone with a terminal illness was chain-smoking in my house. I explained to him that there was a clear prohibition of smoking on the property. I pointed it out in the lease.   This unleashed an inflammatory, half-hour scolding on his part about how I vowed to value his privacy and I had no business showing up unannounced, etc.  I was unable to get a word in edgewise and left completely flummoxed.

I needed to have some work done on my furnace and after a bit of coaxing and haranguing the tenant agreed to let my furnace guy service the furnace. That night I got a call from my furnace guy.

         “So how does it feel having a famous mobster as your tenant?“ 

         “I beg your pardon?“, I said.

         “So you do know who your tenant is, right?” 

…I did not.  

           “Oh yeah! I had like a two-hour conversation with him today. Really, really interesting guy. He’s Johnny Mattangiolo (name changed to protect the not so innocent)! He was the mastermind behind the South Boston mob in the 1980s and early 1990s. I always wondered what happened to that guy! He disappeared in the mid 90s and here he is! He’s living in your house!“

It all made sense now. The privacy. The cash payments. The fake name and the fake identity for the background check. I was renting to a mobster. The story about the terminal illness was completely made up.  Thoughts flashed through my mind of what or who he might’ve buried in my backyard. Could I end my lease because he failed to disclose he was a mobster? After all, he did pay on time every month even though it was in large bills? Should I have written that into the lease? “Failure to disclose oneself in the witness protection program is grounds for early termination of lease?”  If I did end his lease early, who would he have come looking for me? As a landlord I expected to get calls about leaky faucets and stopped up toilets. Never though did I figure that I would have to tiptoe around not offending an angry mobster. What to do? 

I made the decision to let him finish his lease and afterwards I put the house on the market. I was moving across the country, and I figured that it would be quite difficult to have the mobster mail $2000 in cash across the country every month.  I sold it for a loss, and it left a severely bad taste in my mouth as to owning property and being a landlord. Never again, I told myself.

Passive Investing From Now On

In theory, I love the idea of real estate. I love the idea of owning a hard asset which can generate cash, provide incredible tax benefits, employ leverage, and have the potential for appreciation. Approximately three years ago, I discovered passively investing in multifamily syndications. I finally found a way to own real estate without the headaches or hassles of being a landlord. I have colleagues who own their own multi-family complexes and enjoy it.  However when I looked at :

       the time commitment of being a landlord,

       the time and energy spent vetting and supervising property managers,

       the time maintaining, repairing, marketing  and renovating properties,

       the time and expense and hassle of dealing with the legal implications and liability of owning my own properties

       the time and expense researching markets, deals, properties and being able to negotiate and outbid other buyers for the best deals

It was clear that for me, syndications were the way to go.

Today I am invested in seven multi-family apartment syndications in six different states, a self-storage complex, a fund of ATMs, a short-term rental fund, a triple-net lease fund, a music royalty fund, a litigation finance fund, and a life insurance settlement fund. In 2016 I was 90% invested in the public equity markets. Today equities are less than 20% of my portfolio. I think the thing that bothered me the most about publicly traded stocks was the fact that one could see on paper exactly what a business should be worth. Yet, it’s price that it was trading for on the market was completely subjective. The best companies in the world with decades of earnings and dividend growth were valued less than start-up IPOs that had never turned a profit. That was maddening to me.

With hard assets such as multi-family real estate, the numbers don’t lie. Value is based on the income that the asset generates. Once an asset’s net operating income (NOI) is revealed, the asset’s value should be quite transparent. I find solace in this, as I do in the fact that I do not see the wild gyrations in value of my portfolio as I did when I was invested in the stock market.

If you are reading this on the Left Field Investor’s website, I probably do not need to sell you on the benefits of alternative investments and passive income. However, if you still believe that the stock market is “the way“ to accumulate wealth, I urge you to learn as much as you can from this site and its community. I truly believe this is a much better way to accumulate wealth and generate passive income. Oh yeah, those Beardstown ladies were found to have completely inflated their numbers and lagged the S&P 500 by two percentage points!


Brian is a former single-family rental and stock market investor who has invested in over 15 crowdfunding deals and syndications since 2017.  He is a full-time anesthesiologist outside of Eugene, Oregon and a part-time entrepreneur / passive income investor. In his spare time he enjoys surfing, skiing, cooking ridiculously spicy food, learning languages and traveling throughout the developing world.  He can be reached at

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.

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