The case profiles Brad Handler, co-founder of Inspirato, as he contemplates and ultimately founds the luxury and leisure membership-based 'destination club,' shortly after selling and leaving an analogous company that he previously also founded (Exclusive Resorts). The case begins with a biographical overview of Brad Handler and the genesis of and logic for Exclusive Resorts. It provides an overview of the luxury vacation property industry, as well as the timeshare, fractional ownership and destination club industry and then dives into the Exclusive Resorts business model and company growth. After Handler decides to leave Exclusive Resorts, the case delves into his considerations and next steps as he evaluates the opportunity for an improved business model to that of Exclusive Resorts. Given Handler's unique understanding of the industry and a few of its inherent flaws (most notably capital intensity and seasonal demand), he recognizes the unique position he is in to improve upon the Exclusive Resorts model. In particular, the 'destination club' sector had previously been characterized by property acquisition and ownership-with significant capital requirements-as well as demand choppiness and supply constraints during weeks of high vacation interest. Handler considers the implications of entering into long-term leases and rental agreements with individuals and third-party vacation home owners, as well as the use of fluctuating "use rates" for each property in the 'destination club' portfolio in an attempt to both reduce the financial hurdles of entering a 'destination club' and to smooth internal demand. The case brings up a number of important considerations, including new venture formation, how and when an entrepreneur should think about a follow-up to a previous venture-especially one with similarities to a previous business and with customer overlap-business model design, and product launch.

The case profiles the protagonist, Vineet Rai, managing partner of Aavishkaar Venture Management Services (an Indian, early stage VC firm with a focus on rural, underserved regions and sectors), as he initially formulates the concept for the Aavishkaar, and seeks to initially capitalize the fund. The case follows Rai through his ongoing struggles and perseverance for capital, after which it discusses the thesis, structure, and nuances of the fund. It then shines the light on a prospective investment by the fund in an Indian dairy company, Milk Mantra, and deliberates whether the specific investment is a prudent one at that moment in the fund's life. It is recommended that this case be taught in conjunction with the GSB's "Note on Angel Investing and Venture Capital in India.

The case profiles the protagonist, Vineet Rai, managing partner of Aavishkaar Venture Management Services (an Indian, early stage VC firm with a focus on rural, underserved regions and sectors), as he seeks to build on the initial traction of his first venture fund and strives to raise a second, larger, and more ambitious fund. The case discusses Rai's "lessons learned" from his first fund (profiled in Case A), and discusses how such lessons have informed a changed approach to the Aavishkaar thesis and fund structure. It also provides a series of snapshots from prospective LPs in the fund being raised.

The case profiles the protagonist, Vineet Rai, managing partner of Aavishkaar Venture Management Services (an Indian, early stage VC firm with a focus on rural, underserved regions and sectors), as he debates whether to make a follow-on investment in a portfolio company, Milk Mantra. The case provides an update on Aavishkaar's fundraising efforts to date (updating Case B), and then provides an overview of the events at Milk Mantra since Aavishkaar's first investment (profiled in Case A). Given that progress at Milk Mantra is a mixed bag, the case raises the question as to whether it's worthwhile for Aavishkaar to increase its investment in and exposure to Milk Mantra.

The case profiles the protagonist, Luke Tashie, CEO of Yobella - a self-serve frozen yogurt retail chain that Tashie acquired via a search fund - as the company struggles post-acquisition. The case provides an overview of Luke Tashie's background, his motivation and subsequent capitalization of a search fund, the identification of the Yobella acquisition, and post-acquisition business challenges. As Tashie struggles to maintain financial viability, he debates how to best work with the current investor group and the companies creditors to avoid a financial bankruptcy. The case has historically been taught in tandem with "Jeff Stevens: United Presort Services and Jetsort" (Case E-485) in a joint session on the topic of "managing and surviving from failure."

The case profiles the protagonist, Chas Eggert, CEO of OPXBIO-a bio-based, renewable chemicals startup-as he decides on the job positions and specific individuals and candidates to hire after a recent successful round of venture financing. The case provides an overview of OPXBIO, its company history, and the company's technology, as well as its founding team. It discusses the company's upcoming goals and objectives, and its human resource needs. It provides an overview of potential job positions to fill, as well as specific job candidates for those positions. Given the company's limited financial resources, it discusses the main considerations Eggert must debate in order to decide upon the positions and individuals to hire.

The case profiles Sujay Jaswa, VP of Business Development at the enterprise software company Dropbox, along with the company's "freemium" business model and Dropbox's sales organization to date. The case discusses the mechanics of a freemium product offering, as well as Dropbox's sales activities to date, which have largely been automated and emphasize inside online sales. With the product's evolution, the company's continued growth, and a shifting customer profile, Jaswa deliberates whether a change to the company's sales organization is merited, and if so, what the structure of such an organization should be. In particular, Jaswa debates whether the company has reached a point in its life cycle that requires an "outbound", direct sales force.

The case is a series of four short, fictional vignettes. Each vignette shines a light on the case's macro-theme of ''motivating others in a management context," and discusses the considerations involved in getting subordinates to achieve specific company goals. The first vignette profiles Lydia Geller, a newly-promoted VP, as she publicly addresses her subordinates for the first time, each of whom had previously been part of her peer group. The second vignette profiles Jeremy Sawyer, the CEO of a software company, as he reviews the sales performance of the company and, in particular, its leading salesman, Victor Mason. Given Mason's disproportionate importance to the company, Jeremy debates the actions he can take to ensure Mason's continued satisfaction and motivation. The third vignette profiles Warren Soroka, the director of sales at a logistics service provider, as he is forced to have a conversation with a long-term employee who has just been "passed over" for a promotion in favor of a younger employee. He debates how best to communicate the decision to the "passed over" employee in a way that ensures his continued motivation and performance at the company. The fourth vignette profiles Rachel Murphy, the director of academics at Barrymore University, as she is forced to give a performance review that includes both positive and negative feedback. Given the mixed nature of the performance review, she debates how best to communicate such feedback in a way that ensures the employee's understanding and continued motivation.