Gelt (Keith Wasserman) / Sky (Galena Wasserman)

Keith Wasserman had always been entrepreneurial—at 15, he bought irregular leather jackets for $10 each and resold them for $100, netting $10,000. But in December 2008, during the depths of the financial crisis, his cousin Damian presented a different opportunity: a four-unit building in Bakersfield, California selling for $150,000 (down from its pre-crash price of $500,000). With an FHA loan requiring only 2.5% down, they scraped together $5,000 borrowed from a friend and a $10,000 credit card cash advance. Keith and Galena, who had met just months earlier when Galena cold-called Keith's father about a commercial lease (and got set up on a blind date), were both hungry and young—both in their early twenties—operating in a market where everyone else was fleeing.

That first fourplex in Bakersfield was structured brilliantly on paper. The mortgage was $700/month, and each unit rented for $695—meaning just two units covered the mortgage, with units three and four generating positive cash flow. But early on, they didn't understand the real estate syndication model. Keith and his partners captured zero cash flow themselves; everything went to investors. This left them cash-poor despite growing their portfolio. By the early 2010s, they'd bought 15 fourplexes, moved into Phoenix (which had been devastated by the housing bust and subsequent immigration crackdowns), and scaled to a 415-unit apartment building on Camelback Road near the Biltmore Hotel. That Phoenix deal required raising $5.5 million in equity—double their previous largest raise. They had to borrow from personal lines of credit and friends just to close, then spent six months raising capital to repay those debts.

Their first investor beyond family was Galena's father's former lawyer, living in Israel, who saw the U.S. real estate crash as an opportunity and deployed $200,000 to buy a 49% stake in their initial three-fourplex portfolio. As they scaled, Galena's parallel business—Sky—was born from her own deal-hunting. She had started as a commercial real estate tenant rep broker, making significant commissions. When one big commission hit her account, it went straight to pay off Keith's credit card debt. She transitioned into single-family spec homes (buying one for $400,000 with seller financing and no money down), then ground-up multifamily development. Both relied on their growing network of 700+ accredited investors, many from their earlier business circles.

The turning point came when Keith read a mentor's book, "Principles of Real Estate Syndication," and restructured their deal terms. Instead of giving all cash flow to investors, they implemented a 7% preferred return—the first 7% goes to investors, anything above that is split 50/50. This aligned incentives and finally allowed Keith and his team to draw sustainable income. For Galena's side, the breakthrough was A/B testing designs on Craigslist before committing to full renovations. She would post different interior photos and ask prospective tenants directly about pricing, de-risking her underwriting. When she bought the 92-unit Pasadena building (beating 46 other offers by seeing value in reconfigurable three-bedroom units that competitors dismissed), she knew exactly what rents it could command because she'd already asked future tenants. Both businesses succeeded by buying distressed or undervalued assets when others saw only problems—the 2008 crash, odd floor plates, termite damage, micro-units—then executing renovations and raising capital efficiently.

By the time of this interview (roughly 2018-2020 based on context), Keith and Galena had collectively purchased over $1 billion in real estate assets. Their investor base grew to 700+ accredited investors across the country, many investing as small as $25,000 per deal. A single friend who invested $25,000 in a 220-unit Salt Lake City property that they bought for $25 million and later sold for $40 million made $50,000-$75,000 in annual cash flow plus a windfall on exit. Keith's Gelt business raised $6 million in equity (from their 700 investors) to deploy into a $4.5 million angel fund alongside partners, diversifying beyond real estate. Both emphasized that the game is about time, inflation, and the power of 'making money on the buy'—finding value others miss, not gambling on future appreciation. They had survived the near-dissolution of their partnership when Damian was drowning in credit card debt and ready to get a 'J-O-B,' but restructured their model and persisted.