On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Nick Corwin, founder of Oak and Ember, to explore what it really looks like to move from long-term rentals into short-term hospitality and eventually into ground-up development. Nick shares how an engineering mindset, strong mentorship, and disciplined downside analysis shaped his early investing decisions.

The conversation traces Nick's evolution from owning Midwest long-term rentals to building unique short-term experiences in the Wisconsin Dells. He explains why chasing the middle of the market can be a losing strategy, how combining units and serving overlooked guest segments created an edge, and why operating short-term rentals requires far more systems and empathy than most investors expect.

Jonathan and Nick also unpack the realities of entitlement risk, zoning battles, and development timelines. Nick offers a candid look at what it takes to push a project through local approvals, manage rising costs, and stay grounded when timelines and budgets inevitably expand.

In this episode, you will hear:

• Why testing whether you even like being a landlord matters before scaling

• How Nick identified underserved short-term rental niches instead of competing in crowded markets

• The operational differences between long-term rentals and hospitality businesses

• Lessons learned from zoning, entitlement hurdles, and community resistance

• Why doubling both your budget and timeline can save you from painful surprises

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Supporting Resources

Connect with Nick:

Website: http://www.stayoakandember.com/ 

Youtube: https://www.youtube.com/@Korwinning 

Instagram: https://www.instagram.com/korwinning/ 

LinkedIn: https://www.linkedin.com/in/korwinning/ 

TikTok: https://www.tiktok.com/@korwinning 

Connect with Jonathan:

Website - www.streamlined.properties 

YouTube - www.youtube.com/c/JonathanGreeneRE/videos 

Instagram - www.instagram.com/trustgreene 

Instagram - www.instagram.com/streamlinedproperties   

Zillow - www.zillow.com/profile/streamlinen​j

Bigger Pockets -  www.biggerpockets.com/users/jonathangreene

Facebook - www.facebook.com/streamlinedproperties 

Email - info@streamlined.properties  

This episode was produced by Outlier Audio.