Houses on the Hill Taiwan

Overview

Houses on the Hill was Jesse Chan’s more upscale real estate development in Taipei, Taiwan, featuring large individual houses built on hillside locations. Unlike the modest Cherry Hill Development Taiwan, these were luxury properties that Jesse strategically rented for approximately 3 years before selling them - a business model that provided both cash flow and capital gains.

Property Details

Location and Type

  • Big houses on hillside location
  • Individual luxury homes (vs. Cherry Hill’s three-story multi-unit buildings)
  • Premium location with views
  • More upscale market segment
  • Hillside setting (desirable in Taiwan for views and prestige)

Business Strategy

Rent-Then-Sell Model:

  • Rented first for about 3 years
  • Then sold the houses
  • Dual revenue streams: rental income + sale proceeds
  • Rental period allowed property values to appreciate
  • Tenants established the neighborhood’s desirability

Jesse’s Simple Philosophy:

“Real estate is really simple. You just look at the land and you like it, you just buy it. Then we build a house. That’s it.”

Comparison to Cherry Hill

Houses on the Hill:

  • Individual large houses
  • Hillside location (premium)
  • Luxury market
  • Rent for 3 years, then sell
  • Higher-end clientele

Cherry Hill Development Taiwan:

  • Three-story buildings
  • Multiple units
  • “Very simple one”
  • More modest/accessible
  • Middle-class market

Jesse diversified across market segments - both luxury and middle-class housing.

Development Process

Construction

  • Rose loved visiting construction sites with Jesse
  • Family dog Sugar guarded construction property at these sites
  • Hands-on owner involvement
  • Jesse personally supervised projects

Financing

  • Used Taiwan’s installment payment system
  • “Put down your money in installments as they build, you pay”
  • Enabled development without massive upfront capital
  • Different from American real estate model

Family Involvement

Rose’s Memories

Construction Site Visits:

“I remember going with Daddy to all the houses. I remember Sugar [dog]. That one dog, he stayed in the construction property.”

  • Father-daughter bonding time
  • Exposure to business operations
  • Learning about real estate and entrepreneurship
  • Ages approximately 10-18 during main development period

What This Taught Rose:

  • Business ownership
  • Real estate development
  • Father’s work ethic
  • Entrepreneurial thinking
  • These lessons likely influenced her career choices

Dog Sugar

  • Stayed at construction properties
  • Provided security against theft/vandalism
  • Part of family’s Taiwan business memories
  • Shows resourceful, hands-on approach

Historical Context

Taiwan Luxury Housing Market (1970s-1980s)

Economic Boom:

  • Taiwan’s “economic miracle” creating wealthy class
  • Growing demand for luxury housing
  • Hillside properties particularly desirable
  • International business community seeking quality housing
  • Expatriate families (like Jesse’s own family) needed upscale rentals

Why Hillside Properties?

  • Views and prestige
  • Cooler temperatures
  • Away from urban density
  • Status symbol in Asian culture
  • Limited hillside land increased value

Rent-Before-Sell Strategy

Advantages:

  • Cash flow during 3-year rental period
  • Property appreciation while rented
  • Market validation - rental demand proved sell-ability
  • Tax advantages (possibly)
  • Established neighborhood - tenants made area desirable
  • Flexibility - could sell when market peaked

Who Rented?

  • Likely expatriate executives
  • International business families
  • Taiwanese wealthy class
  • People like Jesse who needed quality housing in Taipei

Role in Family Success

Funding Education

Real Estate Profits Enabled:

  • Taipei American School tuition ($10,000/year by 1986)
  • All four children to elite universities
  • All four received scholarships
  • Professional success for next generation

Houses on the Hill Contribution:

  • Higher profit margins than Cherry Hill
  • Both rental income and sale proceeds
  • Part of diversified real estate portfolio

Jesse’s Most Successful Business

Real Estate was:

  • Longest-lasting business (outlasted nightclub)
  • Most profitable (vs. import/export, bakery)
  • Most sustainable (better hours than nightclub)
  • Scalable (multiple projects simultaneously)

Jesse’s assessment:

  • Real estate was “really simple”
  • Just look at land, like it, buy it, build
  • No complex training needed
  • Practical, hands-on approach worked

Filipino-Chinese Entrepreneurship Pattern

Jesse’s Trajectory:

  • Philippines: Employee (Purchasing Manager at Eastern Textile)
  • Taiwan: Entrepreneur (nightclub → real estate → import/export → bakery)
  • Real estate was the winning formula
  • From employee to property developer in 10 years

Typical Pattern:

  • Leave Philippines with capital from selling business shares
  • Start business in Taiwan during economic boom
  • Real estate as accessible entrepreneurship
  • Fund children’s education abroad
  • Eventually follow children to USA

Legacy

Financial Security

Houses on the Hill profits contributed to:

  • Family’s 22 years in Taiwan
  • Children’s expensive education
  • Capital to move to USA (1990)
  • Comfortable retirement in Los Angeles

Educational Investment Success

Results of Real Estate Success:

Rose’s Business Education

Visiting Houses on the Hill construction sites with Jesse gave Rose:

  • Real-world business exposure
  • Understanding of real estate
  • Entrepreneurial mindset
  • These influenced her partnership with Warren (attorney and Cardinal Rule Wines co-founder)

What Happened in 1990?

When Family Moved to LA:

  • Houses likely already sold (rent-then-sell model completed)
  • Or sold as part of Taiwan exit strategy
  • Converted real estate assets to liquid capital
  • Enabled move to USA to join children

Research Questions

  • Exact location of hillside properties in Taipei?
  • How many houses total?
  • When were they built?
  • Rental prices?
  • Sale prices?
  • Who were the typical tenants during 3-year rental period?
  • Why 3 years specifically before selling?
  • Are houses still standing?
  • Photos of the properties?
  • How did profits compare to Cherry Hill?
  • Did Jesse use same hillside area or multiple locations?
  • What happened to properties when family moved to LA?