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Founded in 2005, Zillow had become the leading online real estate and home-related marketplace. The brand was recognized as a trusted resource for players in the real estate market, providing information and transparency on home prices. Revenue, which was historically derived primarily from advertising fees paid by realtors and mortgage lenders, totaled $1.3 billion in 2018. This was in the process of changing, however. The company had entered the direct home buying and selling market in 2017. To Zillow, the move was a logical extension of its business model. Research showed that there was pent up desire to sell homes, but that sellers disliked the conventional process. Zillow Offers made home selling easy and fast - for sellers of homes that met certain criteria, Zillow Offers made an offer within 48 hours of the seller submitting a request for an offer online. Zillow Offers provided sellers a fair price and a guaranteed cash close, then performed renovations and hoped to sell the home within a target of 90 days, although actual times varied by market. The company's stock was more volatile in the period since launching Zillow Offers and some industry observers wondered if it was in part due to the market's perception of the risks associated with the new business. CEO Rich Barton believed the "instant buyer" or iBuyer market could one day account for up to 30% of all domestic real estate transactions and that Zillow Offers could bring in an additional $20 billion in annual revenue within three to five years. But there remained work to be done to improve transaction metrics, fend off competition from well-funded startups and incumbent realtors, and convince shareholders of the attractiveness of the new businesses.

The start-up BlueVine Capital Inc. (BlueVine) used data and technology to help finance small businesses via factoring and lines of credit. The case explains the small business financing market in mid-2010s, how CEO Eyal Lifshitz identified the opportunity for BlueVine, and how he built the company through its first five years of operations. Through the case, Lifshitz and his team discover insights about their small business customers that inspire them to change their product portfolio. In December 2018, Lifshitz must decide which new products to launch next.

At-Bay was a cyber insurance startup that offered companies coverage against a wide array of cyber risks-exposure to which the firm was able to quickly assess and price on the basis of technical expertise that traditional insurance carriers lacked. In mid-2019, At-Bay was working to build underwriting revenue ahead of a Series B round of venture funding that the company hoped to receive by year's end. This required not only scaling its underwriting capacity and convincing insurance brokers to include the startup among the carriers they quoted to their corporate clients, but also ensuring that At-Bay avoided the temptation to grow revenues by taking on riskier clients than it might otherwise prefer.

In November 2018, Shaival Shah, the founder and CEO of Ribbon Home had to decide on the next steps for the company. Ribbon had introduced a program that backs consumers with cash offers without creating a loan structure in order to help them compete with iBuyers, such as Zillow Offers and Opendoor. Ribbon had experienced a successful launch in Charlotte, North Carolina which prompted urgent strategic questions. Among them was the appropriate funding model - whether Ribbon be mainly a platform for others to fund transactions, or should it buy and hold homes on its balance sheet, which it could securitize and sell using a line of credit.

In December 2018, the blockchain startup Fluidity was about to participate in its first tokenization deal, which would create digital access to property rights in a 12-unit Manhattan condominium complex. The deal was proof-of-concept for Fluidity, which hoped to develop a business digitizing securities issuance for other real estate assets on the basis of its technical facility with blockchain technology, and in conjunction with its broker-dealer partner, Propellr. A successful transaction would only prompt larger and more urgent strategic questions, however. Among them was the appropriate revenue model for Fluidity-whether to grow by providing its technical services to broker-dealers, by going into tokenized securities issuance, or by harnessing its trading technology to facilitate a secondary market in tokenized securities.

The case opens in 2016 as Barbaros Ozbugutu, co-founder and CEO of the Istanbul-based payment technology start-up iyzico, contemplates the offers the company received for its Series C round. The case then describes iyzico's origins and provides a detailed overview of the business model and growth story that led iyzico to dominate the industry in Turkey within three years of its founding. Having raised A and B rounds from local and institutional investors in 2014 and 2015 respectively, in 2016 Ozbugutu believes that iyzico could benefit from another round, this time from international venture capital, to reach its aggressive growth targets. In the summer of 2016, after an intense few months of talks with potential investors, Ozbugutu was looking at five competitive term sheets from funds with great fintech know-how and emerging markets experience. From the previous rounds, he knew that if he chose the right investors-ones who could also act as advisors-surprises would be rare. He now needed to weigh the pros and cons of the different term sheets and VCs and decide which offers to ultimately accept.

The case opens in July 2016 as Barbaros Ozbugutu, co-founder and CEO of the Istanbul-based payment technology start-up iyzico, contemplates the pros and cons of the different term sheets the company has received for its Series C round. The case then informs the reader about some changes in circumstances that affected the terms of the shortlisted offers. At the end, the case poses this question: Being faced with worsening terms in a volatile environment, should Ozbugutu go ahead with the round, or should he wait and try again at a later point in time?

In late 2017, Camber Creek, a real estate technology focused venture capital firm, had to evaluate a potential investment in Measurabl Inc. which provides real estate companies of all sized with a full SaaS solution for sustainability data.

Spreadsheet supplement to case 218095

Analyzes Snap's value and analyst recommendations following the events described in the B case.

Analyzes Snap's value and analyst recommendations following the events described in the A case.

Snap, the disappearing message app, went public at $17 per share on March 2, 2017, making its two 20-something founders the youngest self-made billionaires in the country. Over the next three weeks, 14 analysts made investment recommendations on Snap: two with buy recommendations, six with holds, and six with sells. When the "IPO quiet period" expired three weeks later, 16 more analysts-who worked at firms that were underwriters for the IPO-issued recommendations: 10 with buy and six with hold, with price targets ranging from $21 to $31 compared to a market price of $23. Elizabeth Kemp, the portfolio manager of a long-only technology fund at Sand Hill Road Capital, had bought 500,000 shares at the IPO price and had to decide whether to harvest her gain or to double down and buy more shares.

Spreadsheet supplement for cases 218006 and 218052.

Redfin, a technology-powered residential real estate brokerage, was founded in 2002 with the intention of using technology to disrupt the real estate industry. Over the next 15 years, Redfin made several changes to its business model. Initially, the company provided less support than a traditional real estate brokerage but helped home buyers and sellers save more money. Over time, in response to customer feedback, Redfin increased the level of customer service it provided while decreasing the amount customers saved, instead relying on its unique online tools to differentiate itself from other real estate brokerages. In July 2017, Redfin went public at a $1.73 billion valuation. Now, in late 2017, CEO Glenn Kelman had to decide what Redfin's top strategic priority should be. Redfin could try to increase its market share, which was currently less than 2% even in the company's top markets, or it could focus on balancing costs and improving its bottom line.