About Us

Giddy up, we ROI at dawn!

Back in 2022 a group of like minded, driven and ambitious real estate investors met at BPCON in San Diego. Committed to growing as investors and supporting each other in the process, a mastermind was formed and the Cash Flow Cowboys were born. Since that inception, we have continued to not just grow as investors, but build this community. Meeting bimonthly via Zoom, this group from all over the country with diverse backgrounds, interests and skills has proven the concept of working together, holding each other accountable and having fun while doing in, we become more.

Meet The Cowboys

Ryan Irwin, Founder CFC, Iowa

Ryan's goals include to create the lifestyle he wants to live and real estate has been a big part of that. His focus is on fix and flip, short term rentals and his portfolio is a mix of single and multi family housing along with doing private money lending. He is a competitive bodybuilder, nutrition and fitness coach. In his downtime, Ryan and his wife enjoy traveling and raising chickens together.

Jefferson Calloway, Maryland

Jefferson was born and raised in Easton, Maryland. He studied philosophy and religion at Chesapeake College while simultaneously working as a ballroom & latin dance instructor and private party stripper. Yes you read that correctly🕺🏻. Served in the US Army as a Warrant Officer and Heli-pilot of 72s (Lakotas) at Fort Rucker, Alabama. Now he makes a living as a professional business and real estate investor. Buys home construction/remodeling companies And single family/multifamily real estate all across the United States. Specialties are Airbnb and long-term buy and hold rentals with a little bit of flipping and BRRRRing sprinkled in.

Chris Pereira, California

Former advertising executive turned Los Angeles Realtor and investor. After 10+ years helping fortune 500 company's better connect with their customers, Chris now helps first time buyers and newbie investors build long term wealth through real estate. Chris currently manages a personal portfolio valued at over $3 million with properties in California, Tennessee, Arizona & Michigan. Investment Areas of Focus: Long Term, Mid-Term, RE Notes / Private Lending, Syndications

Travis Featherstone, Tennessee

Travis is a 2008 West Point graduate where he was a wrestler. He served 5 years after graduation as an infantry officer at Fort Polk, Louisianaand Fort Benning, Georgia. He also completed a combat deployment to Afghanistan. He later earned his MBA from The Haslam College of Business at University of Tennessee. Win addition to his real estate ventures, Travis is a passionate entrepreneur involved in a range of businesses throughout the Tri-Cities region and beyond. He is the founder of Odyssey Enterprises, a firm focused on startup ventures and small business development, and serves as the Co-Founder and President of NetVets Group, a non-profit organization dedicated to providing East Tennessee veterans with centralized resources and support. n 2021, Travis teamed up with his business partner, Nando, to launch The Gray Line Group LLC - an investment company with a growing portfolio of real estate projects across the Tri-Cities area.

Fernando "Nando" Martinez, Tennessee

Nando is a 2008 West Point graduate and former Army Aviation Officer who spent over 15 years leading missions with the 160th SOAR—deploying 11 times to Iraq and Afghanistan, plus tours in Europe and Central America. After leaving active duty in 2024, he parlayed his leadership skills into real estate investing—buying his first home at Fort Campbell in 2015—and today owns residential and commercial properties across Middle and East Tennessee. Based in Nashville, he’s Evolution Mortgage’s VA-loan specialist, still serves as a U.S. Army Reserve Officer, trains in Brazilian Jiu-Jitsu, and coaches youth wrestling.

Tyler Hill, Iowa

Tyler is a real estate investor who has been active in the industry since 2021, focusing on both long-term and short-term rental properties. With a background in remodeling and home services, he has a strong ability to identify potential and add value to each property. Tyler is committed to creating quality housing options while building lasting partnerships within the community.

Brock Hill, Iowa

I’m an entrepreneur focused on real estate investing in Iowa, specializing in live-in flips that transition into long-term rentals. By combining hands-on renovation experience with a long-term rental strategy, I’m steadily building a portfolio designed for both growth and stability. While real estate is my primary focus, I also own Golden Daisy Studios, a photography business, with my wife. I’m always open to exploring new opportunities that align with my passion for building lasting value through real estate and beyond.

Hart Turner, Illinois

Originally from the DC area, Hart spent many years in Los Angeles before COVID prompted a career change that included a move to Chicago. Since then, he has focused on real estate full-time—purchasing a three-unit building last year that he now house hacks, while actively looking to repeat that process again this year. His investments include small multifamily properties and passive apartment syndications, with an emphasis on long-term growth, appreciation, and stability. Outside of investing, he enjoys photography, running, golf, and has recently picked up pickleball.

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Ryan Fenton, Texas

Starting in 2014, Ryan began a side hustle of building his real portfolio one home at a time. With no experience in real estate, Ryan started house hacking before knowing what it was! By 2022, he and his wife grew to a portfolio of 18 units in Austin, TX where they live with their two young boys. Ryan is the GM of Track & Field at FloSports, where he gets to work within a sport that he competed in from 5th grade through his college days at Clemson University. Ryan is originally from Portland, ME where he and his family still visit every year!

Daniel Colletti, Florida

Daniel focuses on scaling up his portfolio through small multifamily real estate using the VA loan and house hacking. Daniel also seeks entrepreneurial opportunities to complement his active duty military income while aggressively working towards financial freedom.

Justin Jayroe, Tennessee

Justin was born and raised in Memphis, Tennessee. He studied exercise science and physical therapy at Middle Tennessee State University and is a NPC competitive bodybuilder. Justin later spent 8 years in Law Enforcement as a deputy sheriff, criminal investigator and interrogator. He has also served as a Director of Security for a logistics corporation, but has spent the last 3 years as a cofounder of Claroe Capital owning and managing a portfolio of single and multi family long term investments. Claroe Capital continues to grow looking to add short term rentals and larger syndication investments.

AJ Draven, California

I’m a Los Angeles real estate investor who transitioned from a career in martial arts, stunts, and fight choreography into flipping homes. What began with a live-in bungalow flip after the 2008 crash has grown into 2–3 unique projects a year, each designed with a family-focused, authentic approach. Today, I’m expanding into long-term rentals and development, including a 2-acre property in LA. I love spending time with my wife and three kids, getting on the pickleball court, and logging plenty of miles driving all over Southern California for youth sports.

Hart Turner, Illinois

Our Backgrounds

As diverse as the real estate industry itself, the Cash Flow Cowboys comes from all areas of the country and back grounds. From the West Coast, to the heart of the Midwest all the way to the East Coast, we have the country covered. Additionally representing multiple aspects of real estate from buy & hold, commercial development, short term, fix & flip and many other levels of entrepreneurship. The one thing that is common is the desire to build wealth and create the lifestyle we want to live on our terms.