WiscoREIA upcoming events

WiscoREIA Milwaukee: Short Term Rentals: How to Find It, Buy It and Get It Booked (13 Oct 2026)

Tue, 13 Oct 2026 23:00:00 GMT

Short Term Rentals:

How to Find It, Buy It and Get It Booked

Thinking about getting into short term rentals but not sure where to start?

Maybe you’ve looked at Airbnb or vacation rentals and wondered how people actually find the right property, figure out if the numbers work and then manage the property once they own it.

Ashley Lang is going to break it all down from beginning to end.

This presentation is built for someone who wants to understand the short term rental business and how to actually get started.

Ashley will cover:

✔️ How to identify markets that make sense for short term rentals

✔️ How to run the numbers before you buy

✔️ What realistic startup costs look like

✔️ Self management vs hiring a property manager

✔️ How to advertise through Airbnb and other OTAs, SEO and direct bookings

✔️ How to build a good local cleaning and maintenance team

✔️ What goes into operating a profitable short term rental

✔️ How to think about your long term hold and eventual exit strategy

If you’ve been thinking about short term rentals and want to understand what it really takes to get started, this meeting is for you.

Come spend an hour with Ashley and walk away with a much better understanding of how to find the right property, buy it, get it ready and start getting it booked.

Speaker: Ashley Lang

Ashley Lang is a powerhouse real estate investor, short-term rental expert, and the founder of Clear Trail Properties. Since entering the short-term rental space in 2018, Ashley has built and scaled a high-performing STR portfolio rooted in one core belief: great design and great systems create great returns.

She currently owns and operates 25+ short-term rental units across Arizona, Central Wisconsin, Northern Wisconsin, and Michigan’s Upper Peninsula, while also scaling a rapidly growing co-hosting company managing an additional 40+ units across the same markets. In addition, Ashley oversees 25+ long-term rentals and flips single-family homes alongside her partner, Buck.

Ashley is known for her obsession with intentional STR design—from floor plans and furniture layouts to guest flow, durability, and the smallest finishing details. She believes design is not decoration; it’s a strategic tool that directly impacts occupancy, ADR, guest experience, and long-term asset performance. Her approach blends creativity with operational efficiency, ensuring properties are not only beautiful, but profitable and scalable.

Beyond building her own real estate empire, Ashley is passionate about teaching and coaching other investors to shorten their learning curve, avoid costly mistakes, and create freedom through real estate-backed businesses. Her work empowers others to confidently turn a vision into a high-performing short-term rental operation.

When she’s not running her companies, Ashley enjoys mountain biking, hiking, camping, and traveling with her boyfriend Buck, their son Korbin, and their three beloved bulldogs.

WiscoREIA Milwaukee Meeting Always Meets on the 2nd Tuesday of the Month from 6:00 PM - 8:30 PM!

Your Hosts: Chris Hake | Ken Collins

Chris Hake – WiscoREIA Owner

Real Estate Investor | Educator | Coach | Entrepreneur

Chris Hake was the founder and driving force behind the rise of Madison REIA, which he launched in August 2012. In 2021, he merged Madison REIA with WiscoREIA, expanding its reach to ELEVEN monthly REIA meeting locations across Wisconsin and growing its community base of guests and members to over 1000 active investors and entrepreneurs.

With more than 30 years of hands-on experience in real estate, Chris is passionate about giving back. He continues to lead monthly meetings in Madison and frequently shares the lessons he's learned from decades "in the trenches." Chris is most energized by helping new investors discover if real estate is the right path for them, and if so, guiding them to the best possible start for long-term success. He speaks regularly at events throughout Wisconsin and across the U.S., covering topics on real estate investing, business, and personal growth.

A lifelong Madisonian, Chris began his investing journey with a house hack in 1994 and since been involved in hundreds of flips and rental properties. Over the years, he has raised more than $20 million to fund deals and has trained thousands of students through his local coaching programs. From 2006 to 2010, he also taught the Real Estate Investing course at Madison Area Technical College, where hundreds more learned the fundamentals from his real-world approach.

Today, Chris focuses much of his energy on growing Just Simple Storage LLC, a storage investment company he founded that now owns 900 units across 9 facilities in Wisconsin, Illinois, and Michigan.

Outside of real estate, Chris is a devoted husband to his wife, Suzanna, and a proud father to their three boys: Tyler, Tanner, and Trelan. He’s also a fan of classic muscle cars (especially Corvettes and Mustangs), and enjoys outdoor adventures like golf, fishing, and pickleball. At his core, Chris is committed to living out his Life and Business Vision each day, guided by strong values and a passion for helping others succeed.

Feel free to reach out to Chris at chrishake@gmail.com

Ken's journey began in the field of social work and psychotherapy, where he dedicated a decade to helping others navigate their personal challenges. Seeking new horizons, he transitioned into the tech industry, joining Hewlett-Packard. Over the next 24 years, he evolved from a Computer Engineer to a Global Project Manager, culminating in his leadership of the Global Sales Lead program, which under his stewardship generated nearly $1 billion in sales each year.

In 2016, Ken pivoted to real estate investing, initially employing the BRRRR (Buy, Rehab, Rent, Refinance, Repeat) method. Upon retiring from corporate life, he focused on creative deal structuring, mastering techniques like Subject-To (Sub2), Lease/Options, and Land Trusts. His portfolio includes over 50 Real Estate transactions in the last 8 years, ranging from mobile homes, single family and multifamily properties, showcasing his versatility and expertise in the real estate market.

Ken credits much of his real estate knowledge and sharpened skills to his active participation in the many WiscoREIA Madison education programs. Through joining their Coaching Program, completing the Blueprint course, and engaging in numerous educational opportunities including hands-on property tours and weekend training events from a variety of speakers sponsored by the REIA, Ken has continuously expanded his expertise in real estate.

Ken is renowned for his proficiency in lead generation and deal negotiation, leveraging a multitude of creative strategies to craft win-win scenarios in real estate. He now steps into his role as a coach for aspiring real estate investors, eager to share his knowledge and experience. He is always on the lookout for personal growth opportunities, being an active member of groups like Lifeonaire and the Generations of Wealth Mastermind group, which further fuel his passion for continuous learning and development.

With a life that beautifully blends family, community, technology, and real estate, Ken Collins is not just a coach but a mentor who understands the art of building wealth through real estate while maintaining a life of balance and fulfillment.

Make sure to bring tons of business cards as you will be meeting with people that you want to get to know!

Meeting Location:

DoubleTree Brookfield

18155 W Bluemound Rd

Brookfield, WI 53045

Please enjoy food, drinks, and TIP YOUR SERVERS!

Our Agenda

5:45 - 6:00 pm Check-in

6:00 - 6:45 pm Mini Vendor Tradeshow + Networking

6:45 - 7:00 pm Haves & Wants

7:00 - 8:30 pm Featured Presentation

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 Milwaukee: Self Storage Deep Dive (10 Nov 2026)

Wed, 11 Nov 2026 00:00:00 GMT

Self Storage Deep Dive

Click here to pre-register!

Join Chris as he gets into the weeds of how he bought, stabilized, managed and grew his first self-storage facility located in Milton, WI

In this meeting, you will learn:

✅ How he found it (68-units with 2.5 acres extra)

✅ Analyzing the numbers (original underwriting)

✅ Financing sources (private lender & bank à equity partner)

✅ Property management (old school to virtual)

✅ New construction of 108-Units (vision, plans, permitting, construction and being the GC)

✅ Why the right team and systems are CRITICAL

This meeting is perfect for anyone who wants to get a peek behind the curtain and is interested in self-storage as a strategy. Whether you're a beginner or an experienced investor, you'll walk away with nuggets and insights that will help you take the next step.

Speaker: Chris Hake

Chris Hake – WiscoREIA Owner

Real Estate Investor | Educator | Coach | Entrepreneur

Today, Chris focuses much of his energy on growing Just Simple Storage LLC, a storage investment company he founded that now owns 900 units across 9 facilities in Wisconsin, Illinois, and Michigan.

Feel free to reach out to Chris at chrishake@gmail.com

WiscoREIA Milwaukee Meeting Always Meets on the 2nd Tuesday of the Month from 6:00 PM - 8:30 PM!

Your Hosts: Chris Hake | Ken Collins

Chris Hake – WiscoREIA Owner

Real Estate Investor | Educator | Coach | Entrepreneur

Chris Hake was the founder and driving force behind the rise of Madison REIA, which he launched in August 2012. In 2021, he merged Madison REIA with WiscoREIA, expanding its reach to ELEVEN monthly REIA meeting locations across Wisconsin and growing its community base of guests and members to over 1000 active investors and entrepreneurs.

Today, Chris focuses much of his energy on growing Just Simple Storage LLC, a storage investment company he founded that now owns 900 units across 9 facilities in Wisconsin, Illinois, and Michigan.

Feel free to reach out to Chris at chrishake@gmail.com

Make sure to bring tons of business cards as you will be meeting with people that you want to get to know!

Meeting Location:

DoubleTree Brookfield

18155 W Bluemound Rd

Brookfield, WI 53045

Please enjoy food, drinks, and TIP YOUR SERVERS!

Our Agenda

5:45 - 6:00 pm Check-in

6:00 - 6:45 pm Mini Vendor Tradeshow + Networking

6:45 - 7:00 pm Haves & Wants

7:00 - 8:30 pm Featured Presentation

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!