WiscoREIA Sheboygan: Exit Strategy Engineering (15 Apr 2026)

Wed, 15 Apr 2026 22:30:00 GMT

Exit Strategy Engineering

The difference between a risky deal and a profitable one often comes down to one thing: your exit strategy.

Too many investors focus only on the purchase price—but experienced investors know that real success comes from engineering the outcome before ever closing the deal. In this session, you’ll learn how to evaluate opportunities based on clear, strategic exit plans that are realistic, repeatable, and aligned with your resources.

By analyzing multiple exit options upfront—whether it’s flipping, renting, wholesaling, or creative financing—you can identify the most profitable path while minimizing risk. Instead of chasing deals and hoping they work out, you’ll learn how to design deals with the end in mind.

In this no-BS presentation, I'll give you exactly what I wish someone handed me on day 1 (and what I'm ruthlessly focused on right now after 7 years of real deals, mistakes, and wins).

In this session, you’ll learn:

✅ How to evaluate deals based on exit strategy—not just price
✅ How comparing multiple exit options can reveal hidden profit opportunities
✅ How to reduce risk by choosing the most realistic and executable path
✅ Why consistent results come from designing outcomes, not chasing opportunities

If you want to make smarter decisions, avoid costly mistakes, and build a more predictable investing business, this session will change the way you look at every deal.

Speaker: Nathan Taylor

Nathan Taylor is a multidisciplinary professional with a background in information technology, business leadership, and hospitality management. He serves as full-time faculty at Lakeshore College, where he teaches cybersecurity, networking, and artificial intelligence, and develops AI training programs for today’s workforce.

Dr. Taylor holds a Doctor of Business Administration from Walden University, where his research focused on how small business owners overcome barriers to adopting artificial intelligence. He also earned a Master of Science in Information and Communication Technologies with a focus on leadership and training.

Before transitioning into education, Nathan held executive leadership roles with global hospitality brands including Four Seasons, Fairmont, and Hyatt, leading multimillion-dollar operations and projects across the U.S. and internationally. He brings that real-world experience into every session, focusing on practical, actionable insights.

WiscoREIA’s Sheboygan Meeting Always Meets on the 3rd Wednesday of the Month from

5:30 pm to 8:15 pm!

Host: Kyle Kaufman

Kyle Kaufman is a law firm owner, attorney, real estate investor, and host of the Meaningful Ideas Trading Club. Kyle was born and raised in Wisconsin. He grew up wanting to help people. He has discovered his life’s purpose to help families in Wisconsin and to provide individuals with commercial space for their business, and residences for people to live.

In 2005 Kyle started practicing law. He handled almost all aspects of the law. Early in his career he took on landlord and tenant matters, and civil disputes involving real estate. He started to advise people starting their real estate portfolios, and drafted documents for investors to use in their businesses and with tenants and property managers.

In 2010 Kyle became a one-third owner of the law firm, now known as HKK Law Offices (www.hkklawoffices.com). Kyle’s practice shifted to family law sometime around 2018, as more and more people called seeking his assistance. Kyle became fascinated with the financial information he discovered while representing individuals in divorce matters and financial disputes between former significant others. He started to study more thoroughly on the issues of real estate, business, taxes, and more.

Today, Kyle’s law practice focuses entirely on family law, including divorce, maintenance, child support, paternity, property division, child custody, adoption, termination of parental rights, guardianship and more. In the legal world, he sees his contributions in this area to have the most transformational impact on the community. An associate at his law firm practices estate planning.

Kyle now owns one-half of the law firm business and leads a team of 15 people.

Real estate has always been an interest, and after advising clients for many years, Kyle and his wife, Sunny, decided to join in on the fun. In the year 2020, Kyle and Sunny purchased a building with 18 residential units and two commercial units. In 2021, with a partner, they purchased two commercial properties. In 2022, Kyle and Sunny bought a 44,000 square foot warehouse with 3 parking lots. They sold the warehouse in 2025 for a profit. In 2025, they converted their Chicago condo into a rental unit, and then acquired 3 duplexes. They are generating passive income from their investments and using the power of delegation to make it all work.

In 2021 Kyle created an online weekly meetup event called the Meaningful Ideas Trading Club. Kyle hosts the program and invites others to share and mastermind on ideas related to personal and business development.

Outside of business, Kyle and Sunny have 6 children, and they enjoy spending their time with their family.

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

Meeting Location:

Legend Larry's

1142 Plankview Green Blvd

Sheboygan Falls, WI 53085

Please enjoy food, drinks, and TIP YOUR SERVERS!

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

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 upcoming events

WiscoREIA Sheboygan: Exit Strategy Engineering (15 Apr 2026)