 In 1965 he founded Cold Comfort Farms, assembling what eventually grew to more than 20 farms totalling more than 4,000 acres (16 km²) in western Dane and eastern Iowa counties, raising purebred Angus, then moving into grain and contract forage production.He developed Shackleton Square Condominium , the first multifamily housing in Shorewood Hills in 1984 and continued to live there until his death.Around 1985 he filed for bankruptcy, breached contracts and lost many of his properties.