WiscoREIA upcoming events

WiscoREIA Janesville: Property Tour – Real Deals, Real Insights (22 Jul 2026)

Wed, 22 Jul 2026 22:30:00 GMT

Property Tour – Real Deals, Real Insights

Real Deals. Real Properties. Real Investor Insights.

Join us for the WiscoREIA Janesville Property Tour and get an exclusive look inside real investment properties. This is your chance to see how experienced investors evaluate opportunities, identify value-add potential, and make deals work.

We'll visit multiple properties and discuss the strategies, challenges, and lessons behind each one. Whether you're a new investor or a seasoned pro, you'll gain practical insights that can help you make smarter investment decisions.

Bring your questions, connect with fellow investors, and learn by seeing real estate investing in action.

During the tour, you'll discover:
✅ What experienced investors look for when evaluating a property
✅ Renovation strategies and value-add opportunities
✅ Financing and acquisition insights
✅ Lessons learned from real projects
✅ How to identify hidden potential in investment properties

Don't miss this unique opportunity to get out in the field and learn from real-world deals!

Property Addresses: Registration required

WiscoREIA Janesville’s Meeting Always Meets on the 4th Wednesday of the Month from 5:30 pm - 8:15 pm!

Hosts:

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:

Property #1

1133 N Claremont Dr

Janesville, WI 53545

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!

WiscoREIA Janesville: End of Summer Picnic Party & Barbecue (26 Aug 2026)

Wed, 26 Aug 2026 22:30:00 GMT

Summer Networking Picnic Party & Barbecue

Click here to pre-register!

Join us as we wrap up the summer with great food, great conversations, and even better company at the WiscoREIA Janesville Summer Networking Picnic Party & BBQ!

This is the perfect opportunity to relax, connect with fellow real estate investors, and enjoy an evening of networking in a fun, casual setting. Whether you're a seasoned investor, just getting started, or simply curious about real estate investing, everyone is welcome!

Come hungry and ready to:

• Enjoy a delicious barbecue with fellow members and guests.

• Network with local investors, lenders, wholesalers, contractors, and other real estate professionals.

• Celebrate another successful summer with the WiscoREIA community.

• Build new relationships, share ideas, and make valuable connections that could lead to your next opportunity.

No presentations. No pressure. Just a great evening of food, networking, and community!

Food & Registration Reminders

To help us plan food quantities, please pre-register at least 48 hours in advance.

We want to make sure there's plenty of food for everyone!

If you have any dietary restrictions, feel free to bring your own food—we'll be happy to throw it on the grill for you.

Bring your appetite, bring a friend, and come celebrate the end of summer with WiscoREIA Madison!

The event is FREE to attend, but registration is encouraged so we can plan accordingly. We can't wait to see you there!

WiscoREIA Janesville’s Meeting Always Meets on the 4th Wednesday of the Month from 5:30 pm - 8:15 pm!

Host:

Tim Dougherty

Carlos Sierra

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:

TBD

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 toEVERYONE!

***Make sure to pre-register***

Click here to pre-register!

WiscoREIA Janesville: Mid-term Renting: How to Rent to Travel Nurses & Doctors (23 Sep 2026)

Wed, 23 Sep 2026 22:30:00 GMT

Mid-term Renting: How to Rent to Travel Nurses & Doctors

Click here to pre-register!

The demand for mid-term rentals is growing rapidly, and healthcare professionals like travel nurses and doctors are driving much of that demand. But how do you tap into this market, and is it the right strategy for your investment portfolio?

Join us as we explore how investors are successfully using mid-term rentals to generate consistent cash flow while avoiding many of the challenges associated with short-term rentals.

In this session, you'll learn:
✅ How to market and rent your properties to travel nurses, doctors, and other healthcare professionals.
✅ The key benefits and potential drawbacks of mid-term rentals.
✅ Mid-term vs. short-term rentals—understand the differences and determine which strategy best fits your investing goals.
✅ Practical tips for setting up and managing a successful mid-term rental.

Whether you're looking to diversify your rental strategy, increase occupancy, or create a more predictable income stream, this presentation will provide actionable insights you can start applying right away.

Come ready to learn, ask questions, and connect with fellow investors who are exploring new ways to maximize their rental properties.

FREE to attend! Whether you're an experienced investor or just getting started, this is a great opportunity to discover one of today's fastest-growing real estate investment strategies.

Speaker:

Dr. Christina Henderson

Dr. Christina Henderson is an anesthesia resident in Madison, WI and the co-founder of Reliable Residence, a startup reimagining how healthcare travelers find housing. Alongside her husband, she launched the company after purchasing a duplex as a pilot — recognizing firsthand the challenge medical professionals face finding quality furnished housing during travel assignments. Reliable Residence connects healthcare travelers to vetted, furnished monthly rentals.

WiscoREIA Janesville’s Meeting Always Meets on the 4th Wednesday of the Month from 5:30 pm - 8:15 pm!

Host:

Tim Dougherty

Carlos Sierra

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!