Cloudland Partners Fund I Launch Letter



Cloudland Capital was founded by Jonny Reindollar and Matt Karle with their inaugural discretionary fund closing in November 2021. The fund’s strategy seeks to take advantage of today’s opportunity set in real estate: to invest with entrepreneurs to aggregate undervalued small real estate projects, and build operating businesses out of a portfolio of assets.


We firmly believe that institutional real estate private equity is broken, and our goal is to tailor an investment approach to meet that opportunity. Typically, institutional real estate private equity is rigid, hierarchical, overly focused on short-term gains and fundraising, investing into a competitive market for $50m+ deal sizes, and often neglectful of ancillary real estate value creation. Whereas Cloudland is dedicated to a long-term time horizon, partnering with the best ideas and people, investing into a real estate space with strong value-dynamics and margin of safety, and building long-term operating businesses out of the real estate.


Cloudland Partners Fund I:

The fund seeks to invest with entrepreneurs to aggregate undervalued small-format real estate (i.e., deal sizes ranging from ~$300k-$20m) and build operating businesses out of these investments. Our strategy is premised on a few theses:

  1. There are niche opportunities of value within the small-format real estate segment, where large institutions aren’t focusing their time or energy

  2. Investing in and managing small-format real estate has typically been inefficient. Our business model solves this inefficiency by partnering with motivated and experienced entrepreneurs to build scalable businesses

  3. Taking a long-term approach (i.e., hold-periods of ten years or longer) allows us to (1) aggregate deals to create wholesale value to sell to larger institutions and (2) materialize operating company (“OpCo”) value by building operating businesses and platforms from our portfolio of assets

  4. Small-format real estate is uniquely positioned to benefit from advances in property-technology (“PropTech”)