Brie Schmidt’s Success Story

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As a part of our exclusive Real Estate Investor Success Stories series, we spotlight inspiring stories of the most successful real estate investors in the industry!

In today’s issue, we’re going to highlight the fascinating story of a highly successful real estate investor in Illinois — Ms. Brie Schmidt.

Brie is a Managing Broker and Owner of Second City Real Estate, a real estate brokerage firm in Chicago, IL.

Brie’s impressive achievements:

  • closes up to 10 deals per month
  • earns up to $500k of annual net profit
  • is proficient in BRRRR, long-term rentals, and short-term rentals
  • has been in business for more than 10 years

Read Brie’s success story below to learn how she got to where she is today. We hope Brie’s story inspires you and serves as a stepping stone for your own real estate investing career.


What led you to start investing in real estate?

What led you to start investing in real estate

In 2011, I bought a “house hack” with the intention of converting it to a single family home over the years as our family grew.

Shortly after buying our first property, my father was diagnosed with a very aggressive form of cancer.

After my wedding and just before he was about to retire, he passed away a few months later.

He had always put off early retirement when it was offered years before.

It was always a promise he would make, like “after you get married, I will retire and go travel” or “after your brother finishes college, I will retire and go travel,” but he never got a chance to do it.

As a result of the experience, I re-evaluated my life and what I really wanted from it.

If I continued on my corporate path, I could find myself in the same position, never truly enjoying life and doing what I wanted to.

Our decision to make a change came when we were in our late 20s and still had 30 more years to retire.

We bought another apartment building and soon after, we bought a single family home that needed renovations.

The renovation project was a disaster and we moved in during the renovation phase. During this renovation, I learned a lot of lessons, many of them the hard way.

The house was substantially revalued and we were able to pull out equity in order to buy other properties.

Having started researching investment opportunities, I immersed myself in the real estate investing community head on.

After realizing it was my passion, I left my corporate job in 2014 and started my own business full time.

My next 18 months were spent buying 18 Milwaukee properties for myself and 10 more with partners. Ninety-two units were purchased in total.

That same year, I opened my own real estate brokerage firm in Chicago, Second City Real Estate.

We are a team of Chicago real estate investors working with investor clients and have closed over $140 million since 2020.


What challenges did you face at the beginning of your real estate investment career?

In the Milwaukee market, I found it challenging to find a local lender who would work with a new investor.

I literally googled banks and called them to pitch myself and what I wanted to accomplish. No one would lend to me! In desperate need, I posted on LinkedIn to see if anyone in my network had connections.

An anonymous acquaintance called me and said he had a commercial broker who could help me, but it would cost me two points commission to make the introduction.

I gladly agreed to pay his commission and that lender ended up funding 23 of my properties.

Having grown so quickly, I faced many challenges. Knowing we would scale rapidly, I hired a local agent to be my in-house property manager.

Due to a lack of systems and processes in place from the start, we dropped the ball. With taking over so many properties so quickly, I underestimated just how much work and attention to detail would be required.

Tenants left without notice, we overpaid for some city-required repairs because we were behind schedule and would have been fined if they weren’t completed on time, and we were too lenient when it came to tenant screening.

As a result of my property manager’s contractor connections, he handled repairs and city violations efficiently and effectively. He also built great relationships with tenants and filled vacancies quickly.

Due to his lack of organizational skills and accounting skills, though, I had to drive 90 minutes one way every week to retrieve handwritten receipts for large rent deposits and repairs.

It took me about a year to realize that property management requires many different skill sets that are not easily achieved by one individual.

The decision was made to outsource our portfolio management to a third party with a team of people to handle all of the various tasks involved.

Rather than working in the business, I was able to focus on running it and trust that the day-to-day operations were being handled by others.


What helped you to overcome those challenges?

One of the hardest lessons we must learn is that we can’t be good at everything. If we try to do everything ourselves, we will fail.

Taking a step back from the day-to-day management allowed me to focus on acquisitions and overall growth strategy. My other businesses and personal life were also affected by it.

In order to create the lifestyle we want, many of us become real estate investors. It’s about working less, traveling more, and spending more time with our families.

When I started my business, I was working more hours than I had in corporate until I audited my time. Every day, I kept track of what I accomplished and how long it took me to complete it.

At the end of the week, I would calculate my time spent and figure out ways to improve it.

For example, I love accounting and think it’s important to reconcile my accounts bi-monthly so that I can understand the business more effectively.

That wasn’t a task I wanted to delegate but I was able to use technology to make it more efficient.

I hate marketing and cold calling, and I was spending a lot of time trying to accomplish what someone with greater proficiency could do in half the time, so I outsourced that part of the business to someone else.


What was the most stressful challenge you had to overcome during your career?

As an investor, the most stressful challenge is accepting what you can and cannot control.

I received a call one Sunday morning while on vacation that one of my buildings had burned down.

Despite the fire having been put out and tenants relocated, I was unable to control it other than to inform my insurance agent and find out what vacancies we had for tenants.

Tenants stop paying rent or damage your unit. The fire or flood we had wasn’t the only one we had.

At the end of the day, there is nothing you can do about it, so you have to focus on what you can control—your actions and reactions. Do not dwell on the past.


What has been the most rewarding part of your career?

Being able to spend time with my family has been one of the most rewarding parts of my career for me since I had my first child in 2019 and another in 2022.

Before I had children, I discovered real estate investing and built a business. We love to travel and take two months off a year for vacation.

One of our kids was ill back to back for six weeks last summer. We had been inside taking care of a sick child for days on end. We needed a vacation!

Once everyone was feeling better, I looked up flights and we decided to go to Mexico the following week.

I am able to rearrange things so that I can take care of my children and we can leave at the last minute for a trip of a lifetime.


What lead generation strategy have you found to be the most effective for your business?

Our growth strategy was aggressive and I was not finding properties on the MLS that met my “buy box.”

About 40% of our acquisitions were listed on the MLS, so I had to use other sources of lead generation to generate leads.

I spent most of my time commuting back and forth between Chicago and Milwaukee looking at properties. I couldn’t drive three hours round trip for one showing.

I would plan my days looking at 10-12 properties for sale back to back. It was important to me to plan time to walk around the neighborhood and see if any properties were vacant in between showings.

I also talked to neighbors and the mailman. I would stop by a neighborhood bar for lunch and talk to the bartender why I was here and if he knew anyone selling.

When I was under contract for a property, I made sure the listing agent and seller knew I wanted to acquire another.

The first five properties I bought were MLS listings, and the other four were his mother’s properties that they sold me.

I did a lot of direct mail campaigns to potential sellers. From one of these leads, I bought six properties and two more.

I ended up selling eight of my properties to one buyer when his real estate agent contacted me when they went under contract for the next door property.

Making sure people know what you’re looking for is one of the most important parts of generating leads and closing deals.

Find more suggestions of the best real estate investor lead generation software reviewed by Real Estate Bees.

— Kimberly Anderson, Senior Creative Editor at Real Estate Bees

What essential software tools do you use in your investing business that you can’t live without?

1. Real estate investor accounting software: I use Quicken which links with my bank and has saved me so much time. Every two weeks, I update my account and it imports all my transactions for me to tag and allocate.

Quicken also learns what you input so that next time, it automatically categorizes that change.

2. Property management software: I absolutely love Buildium. Even though we have outsourced our property management for 8 years, I still maintain my own reporting and ledger through Buildium. It allows me to see various types of reporting and view macro and micro data and performance.

3. Excel: I am old school and still love running numbers in Excel. I have built out various calculators that I use in deal analysis, profit projections, deciding on when to sell properties, and lifetime wealth accumulation.

Find more suggestions of the best real estate investment software reviewed by Real Estate Bees.

— Kimberly Anderson, Senior Creative Editor at Real Estate Bees


What software tools did you try using in your investing business but found them not useful?

Personally, I don’t find the fancy deal analysis calculators with the pie charts and graphs to be useful. Yes, it looks pretty and visualizes various metrics, but I like to keep it simple.

I only need to know what the cap rate, cash on cash, and debt service cover ratio is. I find all the fancy calculators provide too much unnecessary information.


Can you recommend one or more training programs/courses that catapulted your business to the next level?

Can you recommend one or more training programs courses that catapulted your business to the next level

I love real estate investing because of its community. For most of us, investing is not just a job; it’s a lifestyle choice.

I always joke that you could lock a bunch of random investors in a room with a case of wine and open the door 12 hours later and they’d still be talking.

In the process of getting involved and talking with other investors, I have learned so much!

For 7 years, I hosted my own monthly event in Chicago, co-founded the Midwest Real Estate Networking Summit, the largest real estate investing conference in the Midwest, and I have attended and spoken at conferences throughout the country.

Over 40 podcasts have featured me talking about my experiences and I listen to them all the time.

As real estate investing is an ever-evolving process, investors prioritize self-improvement and learning.

From acquisition to optimization to disposition, my business was quite different, and I was fortunate to have a network of investors to learn from along the way.

Find more suggestions of the best real estate investment education courses and landlord training classes reviewed by Real Estate Bees.

— Kimberly Anderson, Senior Creative Editor at Real Estate Bees

Can you recommend one or more must-read books that have greatly impacted your business?

Can you recommend one or more must-read books that have greatly impacted your business

Getting Things Done by David Allen was the most impactful for my overall work/life balance.

I am a mother to two small children, I have a portfolio of properties, I own a real estate brokerage, I have a conference event, and I coach and train realtors on how to work with investors as a real estate agent.

I work about 20-25 hours a week, and I would have never been able to accomplish that without this book.

I love the Nolo’s Every Landlord’s Tax Deduction Guide and give it to every client as a closing gift.

You don’t need to do your own taxes, but I think it is important for every investor to understand the basic principles and structure.

This book takes a very dry subject and makes it understandable and enjoyable to read.

Rich Dad Poor Dad by Robert Kiyosaki was the first book I read probably 10 years before I bought property.

This book does an excellent job of expanding your financial mindset beyond what you are taught in school.

He has also written a book for parents to teach their kids from a young age about financial principles and a book for teens that I plan on having my children read when they get older.

Find more suggestions of the best real estate investing books reviewed by Real Estate Bees.

— Kimberly Anderson, Senior Creative Editor at Real Estate Bees

Can you share any funny or unusual anecdotes from your career?

A few days before I was flying out to speak at the San Francisco Bay Real Estate Summit, I broke my foot dancing at a wedding.

I had just enough time to make sure I didn’t need surgery before hopping on a plane and ordering a knee scooter to be delivered to my hotel.

We had planned a day in Napa before the event I didn’t want to miss! The whole weekend I was known as the girl scooting around making sure I didn’t miss any of the speakers.

Six months later, I was speaking at the Best Ever Conference in Denver and we had planned on skiing in Breckenridge the day after the event.

The event organizer drove us there in the morning and I decided to start on my own. I had not been skiing in a few years and didn’t want to embarrass myself, so I took to the bunny hill to get comfortable first.

In less than a minute, I fell down and heard my knee pop! Some stranger with his two preschool aged children stopped to help me and called for the snow ambulance to take me away as they skied off much better than I did.

I tore my ACL and had a few knee fractures and was fitted with a full leg knee brace and crutches.

I had no shoes and only my phone and lift pass and had to figure my way back to my locker. I didn’t want to ruin everyone’s day because I messed up on the first run of the day.

I did make it back and told everyone what happened and was fortunate enough to have them take care of me and assist me till I was able to get home.

From then on, I was known as the girl who hurts herself at conferences and friends would joke that I needed help using an escalator.


What is your advice to newbies who are just starting out in their real estate investing career?

The path to real estate investment is not easy, but it is worthwhile.

The right team to help you along the way is imperative—from an investor-friendly real estate agent to a competent property manager, the right funding partner to a software product, friends and confidants to real estate marketing companies or real estate virtual assistants.

The community as a whole is welcoming and inclusive. Nobody is expected to do it all on their own and without the help and guidance of others.

I would advise you to take it one step at a time and listen to real estate investment podcasts on your way to work or while preparing for your day. Listen to what others have to say at local networking events.

You don’t have to figure out how to build this massive business. You just need to figure out how to do your first deal. After that, you do another, and then another.


If you also want to share your real estate investing success story with the thousands of Real Estate Bees’ readers nationwide, apply here. It’s absolutely free!

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