
Inspiring stories of active agents investing in real estate and building passive income. We'll dive into how they are delivering a high level of service to clients while spotting opportunities, negotiating with homeowners, signing deals, and building additional streams of income. You'll come away from each episode with practical tips, tactics, and action steps, while being inspired to open your eyes to the potential deals are all around you!
Episodes

Thursday Jan 27, 2022
How Dawn Brenengen Grew Her Influence and Built An Investment Portfolio
Thursday Jan 27, 2022
Thursday Jan 27, 2022
As real estate professionals, we’re better equipped than most to get into the investing side of things. However, all too often, the fear of not knowing stops us from taking the plunge.
How do we get into real estate investing in the first place, let alone turn it into a business? Plus, once we have the business set up, how do we tell people about it?
Is there a ‘right’ way to take real estate investing from side hustle to our primary source of income?
In this episode, Broker/Owner of Trailwood Realty, Dawn Brenengen shares how she built up both her credibility and her portfolio, organically.
"The first step to getting started in real estate investing is going out and meeting people." -Dawn Brenengen
Three Things You’ll Learn In This Episode
- How to meet sellers organically
Is it possible to connect with potential clients without hauling out a tired sales pitch?
- The key to better tenant relationships
How can we stop letting the fear of difficult tenants hold us back from getting started?
- 1 way to get educated on real estate investing
Does learning the ropes of real estate investing need to cost an arm and a leg, or is there a way to get educated without breaking the bank?
Guest Bio:
Dawn Brenengen is the Broker/Owner of Trailwood Realty LLC. An owner of three personal rental properties since 2004, in addition to being both a buyer’s and seller’s agent over the past 2 decades, Dawn’s focus today is on lease-ups (finding renters) and property management in a range of neighborhoods, at all different price ranges. Dawn has previous experience working with both Coldwell Banker Howard Perry, Walston Builder Services and GO Builder, and holds a New Homes Sales Professional Designation. She is a member of the Raleigh Regional Association of Realtors, serving on their Community Service Committee. Over the years, she has also been involved with The National Home Builder's Association and the Triangle Sales and Marketing Council.
To find out more, go to:
https://trailwoodrealty.com/
https://www.linkedin.com/in/dawnbrenengen
https://www.instagram.com/dawnbrenengen/?hl=en

Thursday Jan 13, 2022
Why This Successful Investor Went and Got His Real Estate License w/Nick Cooley
Thursday Jan 13, 2022
Thursday Jan 13, 2022
In this industry, most agents take on investing after years of working in sales. It’s not as common to hear of a successful investor getting their license years into their investing career - but it proves that the two sides of real estate are a high-value combo that can skyrocket our income and opportunities.
For my guest, Nick Cooley, this was the path he took for specific and intentional reasons. What doors does a license open when combined with an ability to speak the language of investors? How can we get our very first investing deals when we don’t have a ton of capital?
In this episode, I’m joined by investor, broker, mentor, consultant and the President of Team Cooley Properties, Nick Cooley. He talks about his unique approach to investing and how a license gave his business a huge boost.
"The goal is to control as many assets safely for the longest period of time possible." -Nick Cooley
Three Things You’ll Learn In This Episode
- Why selling off investment properties is not an option for Nick Cooley
If you’re investing to get as many assets under management as possible, how do you approach deals differently?
- The best path into investing for beginners on a tight budget
What is the least skin-in-the-game way to get your very first investment property?
- Why buying leads and cold calling are outdated methods of generating business
A lot of the ways we were taught to do real estate just aren’t working anymore. What’s the contrarian approach Nick is taking in his marketing?
Guest Bio
Nick Cooley is an investor, broker, mentor, consultant and the President of Team Cooley Properties in Denver, Colorado. Nick is excited to bring an investor's perspective to the large and important financial decision as to where to live, raise a family, enjoy the occasional dinner party... whatever! Buying or selling a home is important not only for the financial implications, but also in the measure that it is the main place where we spend our lives.
For more information, follow @imnickcooley on Instagram.

Thursday Dec 30, 2021
3 Powerful Ways Working As An Agent Feeds Your Investing Operation w/Chris Lopez
Thursday Dec 30, 2021
Thursday Dec 30, 2021
Working as a real estate agent gives us major advantages that align perfectly with investing - the people we know, our access to deals and all the knowledge we have.
It might seem minor to us, but without even knowing it, we have the tools that take investors years to build up - and it’s not that hard to put them to use.
How can we use real estate sales to feed real estate investing? Do we need to be actively acquiring hundreds of properties every year to get a return?
In today’s episode, I’m joined by Investor Friendly Realtor, author and host of the Denver Real Estate Investing Podcast, Chris Lopez. He shares his journey into real estate, and how he built a real estate operation on his own terms.
"The networking, capital and the education from real estate sales is my springboard to go out and invest." -Chris Lopez
Three Things You’ll Learn In This Episode
- What makes real estate feel like less of a grind
How do you build your real estate business around the things you’re passionate and excited about?
- The best way for busy agents to get into investing
Is it possible to run a successful hands-off investing operation?
- How to get more out of our real estate careers
How can you channel the benefits of being an agent into a huge advantage in real estate investing?
Guest Bio
Chris is an Investor Friendly Realtor, author and host of the Denver Real Estate Investing Podcast. He focuses on helping people create their investing strategies, putting the plan in action, and then helping people optimize their rental portfolio. Chris keeps the Denver real estate investing community up to date on everything related to investing in Denver. As the Founder of Envision Advisors at Your Castle Real Estate, his goal is to build a new type of real estate firm designed to help people envision and execute their path to financial freedom in the Denver and Colorado Springs real estate markets. He is currently acquiring residential rental properties in Denver, CO to achieve his long-term goal of $20,000/mo in rents.
For more information, and to get access to Chris’ book, visit www.denverinvestmentrealestate.com/.

Thursday Dec 16, 2021
Thursday Dec 16, 2021
For many agents, the thought of getting into investing is a nice idea...and unfortunately, that's where it stops.
Given how many agents are interested in investing, what is it that's making them think twice about actually getting started? What's behind their hesitation?
Is it simply a case of not knowing how to get started?
In this episode, Lead Investment Specialist at Elevation Realty Network Inc, Dylan Suitor shares how agents can get educated on investing, so 'not knowing how' never has to be an excuse again!
"You can create your own financial literacy, no matter what level of schooling you have." -Dylan Suitor
Three Things You’ll Learn In This Episode
- How anyone can become financially literate
What does education really mean in the context of real estate investing?
- 1 step we can all take to learn the ropes of real estate investing
We might not have personal experience as investors, but what's stopping us from leveraging that of the top players in our markets?
- Which route we should take when we're just getting started
When is it a good idea to hire a coach, and when would joining a team be a better fit for us?
Guest Bio:
Dylan Suitor is the Lead Investment Specialist at Elevation Realty Network Inc. Passionate about creating generational wealth (and helping others to do the same), Dylan is a self-professed 'entrepreneur from the core', with a number of successful businesses under his belt. After getting his start in real estate investing at the tender age of 18, Dylan's true calling lies in helping people take advantage of all real estate has to offer, so they can create the lives of their dreams.
To find out more, go to:
https://www.instagram.com/dylan_suitor/
https://m.facebook.com/profile.php?id=100014066880485&refsrc=deprecated&_rdr
https://www.linkedin.com/in/dylan-suitor-realtor?originalSubdomain=ca
http://www.elevationrealty.ca/
And to contact Dylan, shoot him a DM on Instagram or call his office at 905 592 4220

Thursday Dec 02, 2021
Thursday Dec 02, 2021
Many agents who are interested in adding investment to their financial arsenal can’t help but ask, “can I be great at sales and investing at the same time?”
Yes, it is possible, ESPECIALLY if we can serve a niche that’s urgently seeking investing-minded Realtors to partner with. For seasoned investors, good agents who understand investing are very hard to come by. If you can serve that niche, you can efficiently add a wing to your business that works well with your sales business.
Where do we find the investors, and how do we get them to want to partner with us? How can you expedite your own success as a new investor?
In this episode, I’m joined by founder and CEO at Five Pillars Team at eXp Realty, Shelby Osborne who shares her impressive journey to becoming an agent-investor.
"If you want business, learn investing, you’ll have so much more than you know what to do with." -Shelby Osborne
Three Things You’ll Learn In This Episode
- Why systems are the key to success in real estate
How did Shelby’s time in the military prepare her to build the systems that powered her real estate success in just 3 years?
- Ways to balance investing and selling real estate
How can we structure our investing so that it works with, instead of against our real estate sales?
- The #1 reason every agent should consider investing
Are you living the life you really want, or stuck on the hamster wheel of transactions?
Guest Bio
Shelby is the founder and CEO at Five Pillars Team at eXp Realty. Shelby graduated from the University of South Carolina in 2012, served in the Army for 6 years and got out as a Captain in the beginning of 2018 to dive into Real Estate full time as both a broker & investor in Fayetteville, NC.
Following her first year as a broker, Shelby was recognized as the Keller Williams Rookie of the Year for the “Carolinas Region” (all of North & South Carolina) and began to expand, creating her own team of real estate professionals. Five Pillars Realty Group became official in 2019 and expanded to Charlotte, NC in 2020. Both Fayetteville & Charlotte offices specialize in helping military and investors nationwide meet their goals. “Pints & Properties,” their Real Estate Investors meetup, is booming & continuing to grow rapidly.
Meanwhile, Shelby was relentless in growing her rental property portfolio. Since purchasing her first intentional rental property in November 2017, she now owns 74 units, acquired using several different strategies and comprising a little bit of everything: single-families, residential multi-family, commercial multi-family and short-term rentals… plus a bit of airbnb arbitrage.
Between CEO duties and continuing to invest, Shelby operates “Pillars Consulting” – a company designed to transform Real Estate Brokers into their full potential -- and “Life & Lens Photography” -- a company designed to showcase Multi-Family Syndication projects and help investors raise private capital.
For more information, visit https://fivepillarsrealty.com/ and follow @realestatewithshelby on Instagram.

Thursday Nov 18, 2021
Thursday Nov 18, 2021
Many agents who are sitting on the sidelines of investing are being held back by one thing alone - fear. They aren’t dead set against investing, they just feel some trepidation about getting started.
Once you’ve identified your desire to invest, how do you push past fear and get into action? What resources can we tap into to make the first deal less scary?
In this episode, I’m joined by San Diego-based agent and investor, Jessica Wilkinson. She shares the one thing any agent can do to build their confidence in the investing space.
"Get around the people who are investing. Take notes from the well-educated, well-versed agents around you." -Jessica Wilkinson
Things You’ll Learn In This Episode
- The advantage many agents take for granted
As agents, we spend our careers making other people rich, why not do a little bit of that for yourself?
- Ways to get funding for deals without stockpiling capital for years
How do you get hard money lenders to believe in you as a first time flipper?
- How to get mentored by the best investors in your town
What’s the one simple statement that will take us very far as aspiring investors?
- How Jessica reduced her marketing spend by $75k
Can we easily eliminate the need to have a high-powered marketing budget? If so, how?
Guest Bio:
Jessica Wilkinson is a Realtor and investor at Big Block Realty, Inc. Just after graduating high school, she took the oath and served our country in the United States Marine Corps for six years. After an honorable discharge, Jessica served over 10 years in San Diego County trial courts as an Official Court Reporter, giving focus and attention to detail in the forefront of her livelihood. Eventually, her love of architecture, real estate, and design had given her a passion that she now enjoys sharing with others in the field. After completing several remodels and designing homes on her own accord, Jessica now shares her skills and experience with all of her clients. Whether you are a first-time homeowner, veterans needing housing for a short time, all the way to complete overhauls for investors, she knows how to manage the entire process from start to finish, ensuring maximum investments with impeccable attention to detail. Jessica’s training in leadership, operations and accountability roles lend her to a driven and meticulous practice in Real Estate. Homeowners and investors alike can rely on her throughout the entire process of house hunting, renovation, design, and sales for best returns on investments.
To connect with Jessica, visit https://www.linkedin.com/in/jessica-wilkinson-822213158/.

Thursday Nov 04, 2021
Thursday Nov 04, 2021
In an industry with thousands of agents, the ones who take on investing are few and far between, despite the perks and the clear path to wealth it offers.
Many agents overthink investing, but it’s really as simple as doing your first deal. Even if it’s not perfect, getting started right away is the right move. It’s the least expensive tuition you’ll pay for a tremendous outcome.
If you’ve never bought an investment property, how do you overcome your hesitation? Does investing negatively impact our work as agents? In this episode, real estate executive and Partner at OakGrove Development, Matt Drouin shares why becoming a successful agent investor is easier than you think!
"Do a deal. It’s the least expensive tuition you’ll pay for a tremendous amount of upside on the back-end." -Matt Drouin
Three Things You’ll Learn In This Episode
- Why real estate investing is “passive-ish income”
Is there such a thing as a completely hands-off investing operation?
- How investing impacts your real estate sales business
Does investing make us better agents or will it compromise our ability to serve our clients at a high level?
- The best time to buy your first investment property
When it comes to investing, should we wait for the perfect strategy or take immediate action even if it’s imperfect?
Guest Bio
Matt is Partner at OakGrove Development, a real estate investment and development firm with a special focus on value-add commercial and residential properties in Rochester, NY. Over the last 15 years, Matt has been in real estate management, brokerage and development and grown his portfolio to 120 units of residential and commercial property. His company mission is in developing real estate projects that not only add value to their investors but also puts long term community interests front and center. Matt believes that you can do well and do good as a real estate developer and that ultimately community centric development boosts long term profits for investors.
For more information visit http://www.rocrealcapital.com/, connect with Matt on LinkedIn and follow him on Instagram.

Thursday Oct 21, 2021
Thursday Oct 21, 2021
One of the biggest reasons agents are resistant to investing is the fear that it will spread them too thin and eat away the time they dedicate to generating leads. But what if investing could make your entire business more efficient and profitable by allowing you to create your own luxury listing inventory?
A lot of agents are looking to jump into the luxury market, but struggle to find the deals in a highly competitive niche. Beau Blankenship was able to turn land deals into luxury properties, and he earns more by being both an agent and an investor in the transaction.
How did he combine land deals, listings and investing to create a killer business model?
In today’s episode, real estate advisor, agent and investor, Beau Blankenship shares how to create your own inventory from the ground up.
"Living on commissions can be tough, so invest and sell homes simultaneously." -Beau Blankenship
Three Things You’ll Learn In This Episode
- Why working with investors is more stable than just focusing on our sphere
How do you turn one investing relationship into a steady stream of multiple deals over many years?
- How to turn investing into a win for everyone on your team
When we set up an investing operation alongside our sales business, do our agents and staff benefit from it?
- How to gain a competitive advantage in the luxury market
Luxury real estate is highly competitive, how do we create our own inventory so we’re not fighting other agents for deals?
Guest Bio:
Beau Blankenship is a real estate advisor, agent and investor. He currently serves as a luxury real estate sales associate on Scenic Highway 30A. Knowing the potential of this surrounding area, Beau has always had a passion for increasing awareness to the significance of investing smart, and placing your hard earned money where it counts and where it will thrive. His zeal for real estate has multiplied over the years and he now owns Engel & Volkers in Santa Rosa Beach, Florida. As a former athlete, the discipline Beau acquired translates in how he performs for his clients. By delivering originality, enthusiasm, leadership, and die-hard dedication, any of his clients are certain to be in good hands. For more information or to connect with Beau, visit https://beaublankenship.evrealestate.com/ and https://www.linkedin.com/in/beau-blankenship-3265a759/.

Thursday Oct 07, 2021
How to Generate a Fortune As A Newbie Investor On a Shoestring Budget w/Chris Bounds
Thursday Oct 07, 2021
Thursday Oct 07, 2021
The thought of real estate investing is enough to get most agents excited, but when it comes to actually getting started, only a small number are willing to take the leap.
What’s stopping more people from getting into the space? Is there a way for agents with no experience in investing to feel more comfortable taking the first steps?
In this episode, Realtor, investor and founder of Invested Agents, Chris Bounds shares his advice for newbies.
"Living below your means is very simplistic, but key. If you’re always spending what you’re making, it's hard to grow." -Tom Cafarella
Three Things You’ll Learn In This Episode
- How to get investment deals without a marketing budget
Is there an alternative to running ads when we simply don’t have the funds to set up an extensive marketing campaign?
- Why flipping holds us back from the GREAT life
Flipping is one of the first things agents think of when they hear the words ‘real estate investing,’ but could that particular activity be stopping us from reaching our income goals sooner?
- Key advice for all newbie investors
How can we set ourselves up for success when we’re brand new to the space?

Thursday Sep 23, 2021
Thursday Sep 23, 2021
A house is a dwelling and roof over your head, but it can also be a powerful financial tool, a cash flowing asset, and a massive income driver. Our guest today saw the potential of real estate investing when he bought his first home, and immediately pulled the trigger on building his own portfolio.
Many agents find the first deal very intimidating, but taking that leap might help you discover your passion for investing.
How can agents set themselves up for success when they take on investing?
In this episode, real estate agent, investor and property manager, Kyle Craig shares his investing journey, and why buying his own home made him want to pursue a career in real estate.
"You have to put in the hours and the more you understand the process, and the more knowledgeable you are, the easier it is to balance investing with sales." -Kyle Craig
Three Things You’ll Learn In This Episode
- The formula for headache-free property management
Managing property and dealing with tenants makes a lot of people nervous about investing. Can you avoid the headaches of being a landlord?
- Why we have to approach 203K loans with caution
How can we take advantage of 203K rehab loans while avoiding expensive pitfalls of this strategy?
- How to find opportunities in commercial real estate
Commercial real estate has a lot of potential. How can investors tap into the unlimited hybrid creativity of this asset class?
Guest Bio:
Kyle Craig is a Real Estate Agent, Investor and Property Manager. Having started with Clockhouse Realty just over a year ago Kyle has really hit the ground running and has quickly found great success with residential and commercial sales. He is currently licensed as a real estate agent in both MA and RI. On the investing side, Kyle is closing on a couple of personal investment properties and planning to continue expanding his portfolio. He is also working toward eventually having his own brokerage.
Connect with Kyle on LinkedIn