Welcome to Winning In Cleveland!

Local knowledge, community and tools to help you build wealth investing in Cleveland real estate.

What is Winning In Cleveland?

Winning in Cleveland is a dynamic, real estate investment community designed to connect members with the local knowledge, skills and relationships needed to build wealth investing in Cleveland, Ohio.

We bring together an eclectic mix of thoughtful, ambitious, people who are committed to achieving our goals of financial freedom so we can spend our time doing what we love with those we love and create the future we want for ourselves, our families and our causes.


What does it mean to "win" in Cleveland?

  • Reaching our financial goals
  • Having the time, money and ability to enjoy life both now and later
  • Building a business that helps your tenants, the city, your customers and clients win too
  • Building a legacy
  • Having enough to give with joy
  • Becoming a market expert through masterminds, book clubs, forums, courses and more.
  • Sharing what you've learned to help someone else along the way

The Answers You've Been Looking For

Over the years, we've had hundreds of conversations with people just like you who want to:

  • Understand Cleveland neighborhoods
  • Find "good" deals
  • Find reliable contractors
  • Know who to trust
  • Learn Cleveland from a local perspective
  • Find an investor friendly real estate agent in Cleveland
  • Connect with other investors and experts who are also focused on Cleveland 
  • Build a team 
  • Build the confidence to actually start!

Sound familiar? If so, Winning in Cleveland is for YOU!


But, you may NOT want to join us if...

  1. You prefer to gather information about Cleveland investing from people who don't live or invest in Cleveland 
  2. You don't want to build the confidence to take action toward your goals
  3. You don't want to connect with local experts or service providers
  4. You'd rather not be part of a community of others who have the same goals as you
  5. You already know everything about Cleveland and don't want to risk learning more from others' experiences
  6. You are not interested in engaging conversation with thoughtful, respectful people who may be looking for business partners like you

What you'll Get

Through groups, challenges, polls, courses and a calendar of exclusive events, Winning in Cleveland will help you

  1. Motivation- What's your why?
  2. Focus- What's your goal?
  3. Resources- What do you need to progress?
  4. Contacts- Who's missing from your team? 
  5. Results- What wins do you now have to share?

Our Why

Hey everybody. We are Erin & Dwight, founders of Winning in Cleveland. The most important things you need to know about us are in this picture. These 3 are our "why". They are the reason we invest in Cleveland real estate and help others do the same every day. 

We know that you also have at least one reason why you absolutely MUST succeed as a real estate investor. We hope that Winning in Cleveland will help you zero in on that reason and go after it so you can create the future you want for yourself, your family and your causes.

Let's get it!


What They're Saying


I am so glad you've created this! I've been looking for Cleveland-specific investing information for a very long time. -J.C., new out of state Cleveland Investor


I'm looking forward to connecting with other local investors and learning from their experiences and strategies. -Jack, local experienced Cleveland investor


This is GREAT! I have been ready to start for a long time. I just needed some accountability. -Patrick, local future Cleveland investor