Leasing Is the Business Plan: How Better Leasing Drives Better Returns
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What if your leasing process is leaving money on the table?
Leasing is often treated as a simple task: list the property, show the unit, find a tenant, and move on. But for investors, leasing can have a major impact on cash flow, NOI, and the long-term value of a property.
Join Ryan Leonard for a behind-the-scenes look at how strategic leasing can become a powerful tool for improving investment performance. Ryan will share the systems, processes, and data-driven strategies his team uses to make better decisions around rents, marketing, lead conversion, vacancy, and tenant demand.
He’ll also walk through the turnaround of a 16-unit Milwaukee property, sharing how changes in leasing strategy helped drive significant rent increases after acquisition—and how those lessons are being applied across larger multifamily portfolios today.
If you own rentals, manage properties, or are looking to scale your portfolio, this is an opportunity to rethink leasing as more than an operational task.
Come learn how better leasing decisions can translate into better properties, stronger NOI, and better returns.
Speaker:
Ryan Leonard
Ryan Leonard is a multifamily real estate investor and co-owner of BlackRidge, a Wisconsin-based real estate company focused on multifamily investments and apartment leasing. Its leasing arm, BlackRidge Leasing, provides property owners with a white-glove, lease-only service designed to improve and streamline leasing operations.
Through a combination of creative deal structures and partnerships, Ryan has focused on value-add multifamily investments throughout the greater Milwaukee area, including a 51-unit acquisition currently under contract and set to close in fall 2026.
Between his own investments and his leasing clients, Ryan has developed a particular interest in the systems, data, and strategies behind effective leasing and property operations-and how more organized, intentional execution can translate into stronger overall investment performance.
WiscoREIA Janesville’s Meeting Always Meets on the 4th Wednesday of the Month from 5:30 pm - 8:15 pm!
Host:
Tim Dougherty
I’m a Christ-follower, husband, father, and full-time real estate investor with a passion for transforming properties and helping people. I began investing in 2008, and more than a decade ago I left my W-2 job to pursue real estate full time—a decision I’ve never looked back on.
Over the last five years, my team and I have completed 50+ deals across flips, rentals, and wholesales. As a landlord, we currently own 17 doors and growing, continually expanding our portfolio while improving the neighborhoods we serve. As the owner of Doc The House Buyer, LLC, our mission is to support homeowners throughout South Central Wisconsin, especially Rock, Jefferson, and Dane counties, by providing honest solutions for distressed sellers who need a trustworthy, timely option.
A core belief of mine is that once a student, always a student. I’ve spent the last 13 years learning, growing, and sharpening my craft through faithfully attending local REIA meetings, and that education continues today. Just as importantly, I’ve grown through serving and coaching others, paying it forward one person at a time. Helping new investors complete their first deals is one of the greatest privileges of my career.
I’ve successfully raised millions of dollars in private capital to fund real estate transactions, and I’ve built my business on two pillars: creativity and relationships. Whether structuring deals, solving complex problems for sellers, or collaborating with partners, these values have guided every step of my investing journey.
I’m committed to serving the Rock County community by sharing my experience, my network, and my passion for helping people build wealth through real estate. My goal is simple: to make a positive impact and empower others to succeed, both in business and in life.
Carlos Sierra
Carlos Sierra is a Christ follower first and a real estate investor with five years in the business, working across rentals, fix-and-flips, and primarily wholesale deals. He's the co-owner of WI Buy Real Estate alongside his wife, Brenda. Originally from Penjamo, Guanajuato, and raised in Green Bay, Wisconsin, he earned his bachelor's degree in Marketing from the University of Wisconsin-Milwaukee. He spent over eight years in the tech world helping businesses scale through better systems, processes, and tools.
Proud dog dad to Mushu and Candela. When he's not looking at a deal, he's either training for Hyrox or at Bible study.
Make sure to bring tons of business cards as you will be meeting with people that you want to get to know!
Our Agenda:
5:30 PM – Registration Check-In & Networking
• Informal networking with fellow investors
6:00 PM – Meeting Kickoff
• Welcome by Host and/or Co-Host
• WiscoREIA PowerPoint / announcements and updates
• Sponsor Introductions
• Haves & Wants – Share deals, services, and resources
6:30 PM – Deal Case Study
• Breakdown of a real deal with teachable moments (good, bad, ugly)
7:00 PM – Networking Breakouts
• Guest Orientation with Host
• Member & Sponsor general breakout for continued connection
7:15 PM – Main Presentation
• Host introduces Guest Speaker
8:15 PM – Closing Remarks
• Final thoughts and upcoming events
• Invitation to the "Meeting After the Meeting" for more networking
Meeting Location:
Sidelines Sports Pub & Grill
731 S Wuthering Hills Dr
Janesville, WI 53546
Please enjoy food, drinks, and TIP YOUR SERVERS!
The meeting ends at 8:15 PM, but we’ll continue with an informal after-meeting for anyone who’d like to stay.
You can stay after the meeting as well to network! Remember to bring your deals!
Our doors are open to EVERYONE!
***Make sure to pre-register***
Click here to pre-register!
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