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Entrepreneurship Case Studies

Logo of connecticut innovations

Jean Rosenthal and Song Ma

Asset Management, Entrepreneurship, Innovation & Design, Investor/Finance

Matt McCooe had been navigating the similarities and differences between managing private and state-sponsored venture funds since he was appointed Connecticut Innovations’ CEO. Seven years in, McCooe and his investment team were considering whether yet another difference between private venture firms and Connecticut Innovations (CI) was an opportunity or a hazard for CI’s funds.

Two screenshots of the Umi Kitchen app, one showing a sandwich on a prezel bun, one of a woman with pigtails and glasses holding two plates of food
Screenshots of the Umi Kitchen App
Serena Dai, ny.eater.com

Khalil Tawil and A. J. Wasserstein  

Customer/Marketing, Entrepreneurship, Innovation & Design, Leadership & Teamwork  

Khalil Tawil (Yale Law ‘19) started Umi began with a simple idea: Home Cooking, Delivered. But now Umi was experiencing turbulence and flagging. With funds running run out from his venture capital raise, Tawil had to confront the reality that Umi was possibly unviable, and that he might have to wind up operations. He had founded Umi in 2014 as a law student at Yale. After raising an impressive amount of capital, Tawil had launched Umi in Brooklyn in March of 2016.

Bright Red box with white text in the lower left corner reading "European Wax Center"
Logo for European Wax Center

Joseph Golden and A.J. Wasserstein 

Competitor/Strategy, Entrepreneurship, Investor/Finance, Leadership & Teamwork 

Karen and Twan Bentlage had opened two locations of the European Wax Center in Manhattan. When Karen and her husband Twan had secured exclusive rights to develop the Manhattan market for European Wax Center, they had recruited an operating partner to manage the Centers on their behalf. That worked for the first few months, until the Bentlages’ hand-picked partner suddenly walked away from the venture in the summer. Out of necessity, Karen had stepped in to fill the leadership void on a temporary basis. By December 2011, five months later, Karen was exhausted.

Evan Okun and Song Ma 

Entrepreneurship, Innovation & Design, Investor/Finance, Law & Contracts, Social Enterprise, Sourcing/Managing Funds 

Investors poured in, eager for a slice of his Series A raise. Yousef Kassim’s company, Easy Expunctions, boasted nearly a $2 million run rate and the round’s price tag was cheap: $18 million pre-money. Yet amidst investor enthusiasm, Kassim wrestled with how his company would balance social impact and commercial viability.

a blue c with the word connecticut below in the same blue
CT.gov

Gwen Kinkead and Teresa Chahine 

Employee/HR, Innovation & Design, Leadership & Teamwork, Social Enterprise, State & Society  

From 2011 to 2019, the Connecticut Department of Social Services (DSS), under the direction of Roderick Bremby, managed to transform its $570 million food stamp program from one of the worst in the nation to one of the best. Having achieved such a remarkable turnaround, observers wondered what else the DSS might do to further deliver on its mission of "providing person-centered programs and services to enhance the well-being of individuals, families and communities."

Allison Mishkin and A.J. Wasserstein 

Entrepreneurship, Investor/Finance 

Lia Majid had spent nearly a year and a half searching for a business to acquire and thought she’d finally found a deal worth pursuing. She spent months negotiating with the firm’s sellers and believed she was on the verge of a purchase. However, at the last minute, her backers and mentors at the Search Fund Accelerator (SFA) wanted her to completely restructure the deal.

Majid was part of the first cohort of SFA. SFA was the brainchild of Timothy Bovard who founded the accelerator to help search fund entrepreneurs vet deals, review proposals, and provide emotional support during the search. Through SFA’s leads, Majid had identified a target company that was willing to sell one of its divisions, but she still needed Bovard’s input before drafting a Letter of Intent (LOI) for the seller. Bovard, however, was concerned about the proposed carve-out acquisition, a complex task for even a seasoned CEO, let alone a first time CEO.

Faced with Bovard’s concerns and SFA’s new deal structure, Majid had to decide whether to reengage the target firm with this new deal or to move on to investigate other prospects.

Black screen with white text, reads NEXTHVN with the leftmost part of the drawn to the bottom edge of the screen and the right most part of the N reaching up to top of the screen
NXTHVN

Jean Rosenthal, Kate Cooney, and Jaan Elias

Arts Management, Entrepreneurship, Innovation & Design, Investor/Finance, Social Enterprise

Titus Kaphar was a highly successful artist. One dominant theme of his work was creative reuse  of classical images to expose hidden relationships of race and subjugation. When he moved back to New Haven, Connecticut, he began a project that required creative reuse and reframing on a much grander scale. He co-founded an organization, NXTHVN, to take an old factory building in a rundown neighborhood and reconfigure the space into an art incubator, artists’ studios, and a community center.

A.J. Wasserstein

Employee/HR, Entrepreneurship, Leadership & Teamwork

The case consists of written responses from Justin Schulte and his wife Samantha, who agreed to answer a set of identical questions on their views and perspectives about Justin’s choice of becoming an entrepreneur after graduating Yale SOM. These are the types of questions likely to come up for other entrepreneurs making a choice about their next steps, and how their decisions will play out with their own families. Some entrepreneurial couples have the foresight to explore these interesting, and potentially raw, conversations, and some do not. Aligning expectations and aspirations between partners in an entrepreneurial marriage can attenuate ambiguity and stress in an inherently nebulous and anxiety filled path. For Justin and Samantha, it is interesting to see where their thoughts align and where they veer apart, what concerns they have about Justin’s career decision, how it will impact various family members, and how they each perceive risk and uncertainty.

Jason Pananos and A.J. Wasserstein

Employee/HR, Entrepreneurship, Investor/Finance, Leadership & TeamworkSourcing/Managing Funds

In October 2014, Joe Smith, the CEO of Smith Brothers Insurance, reflected on the fact his business was caught in the midst of three separate succession challenges. Smith Brothers was an insurance agency owned by Joe and his sister, Kim, in Connecticut that had achieved strong growth over the previous decade.

Patrick Sissman and AJ Wasserstein

Asset Management, Entrepreneurship, Investor/Finance, Leadership & Teamwork, Social Enterprise, Sustainability

Tom Bird, founder of the early-stage impact investment nonprofit The FARM Fund, settled into his seat for a flight from Boston to Amsterdam in February 2016. The seven-hour transoceanic flight would give him plenty of time to mull over two dilemmas – one a long-term question of the future of FARM and the other an investment opportunity FARM had recently been presented.

A. J. Wasserstein

Employee/HR, Entrepreneurship, Innovation & Design, Leadership & Teamwork, Social Enterprise

Mike Erwin, a decorated army veteran from West Point, never envisioned himself as a social entrepreneur or activist. Yet in 2012, he found himself the CEO of an organization with 15,000 members and 34 chapters reaching from Syracuse, NY to Houston, TX. Though Erwin was proud of his organization’s growth and had excelled in leadership positions, he questioned whether he was the right person to scale Team Red, White and Blue. Would someone else with more experience be more appropriate? If he indeed moved on, how could he ensure the organization would continue to thrive amid a change in leadership and potential restructuring?

A.J. Wasserstein

Entrepreneurship, Investor/Finance, Leadership & Teamwork

During his time at the Yale School of Management, Matt Dittrich (Yale SOM ‘18) became interested in how recent MBA students gathered search funds, structured small acquisitions, propelled themselves into being a CEO, and then participated in a liquidity event only a few years after acquisition and graduation.  He appreciated the case studies about entrepreneurs facing acquisition, strategy, and financing issues.  But what did entrepreneurs do after their exits?  At the urging of his teacher, A.J. Wasserstein, he interviewed former search fund entrepreneurs who had experienced an exit to learn what exactly they chose to do, and why. Overcome by curiosity, Dittrich was excited to begin his informational interviews (summaries included here). 

A. J. Wasserstein

Employee/HR, Entrepreneurship

Before entering the Yale School of Management, James Guba (SOM’18) had thought about becoming an entrepreneur. He did not have a specific idea to build a business around, but he did aspire to take charge of an organization and grow it. At Yale, Guba discovered an entrepreneurial niche called “search funds” that would allow him to acquire and lead a company that he had not built from scratch. Inspired, Guba met with search fund entrepreneurs to learn about their different paths to building their funds.

A. J. Wasserstein

Customer/Marketing, Entrepreneurship

After nearly two years of searching, Kalil Diaz (SOM '14) wondered if he had finally found the company for which he had been looking. The decision he was facing would have a big impact on his investors as well as his own life. He was somewhat confident he could access funds from his current investors to purchase the company despite several investors being slow in their response to commit. However, Diaz still wondered if making the investment was the right move. How would he transition from the search to being CEO and running a company? Would the acquisition provide suitable financial returns for his investors and himself?

Elise Rindfleisch and Allison Mitkowski

Customer/Marketing, Entrepreneurship, Sustainability

In October 2007, Clorox announced that it would buy Burt’s Bees for $925 million – more than five times Burt’s Bees’ annual sales. Clorox’s move caught many in the industry by surprise - Burt’s Bees had a folksy image and natural appeal for customers. Could such a brand find a home within a company best known for a toxic cleanser? Would Clorox’s push into “green” cleaners satisfy Burt’s Bees’ faithful customers? Had Clorox paid too much for its acquisition? Or, were there potential synergies that justified the purchase? What was the future of this market?

Rodrigo Canales, Jean Rosenthal, Jaan Elias, Ashley Pandya and Samuel Sturm

Entrepreneurship, Healthcare, Innovation & Design, Social Enterprise, State & Society, Sustainability

In a unique partnership, governments, designers, architects, academics, and NGOs had come together to create new sanitation solutions for India's urban slums. Specifically, the group set about tackling one of the developing world's leading problems – open defecation in crowded urban settings. But by fall 2013, not a single community toilet had been approved. What had gone wrong? And what could this experience teach others about an overall solution to the problem?

Rodrigo Canales, Jean Rosenthal, Jaan Elias, and William Drenttel

Entrepreneurship, Healthcare, Innovation & Design, Social Enterprise

The traditional Zulu greeting, "Sawubona," literally translates as "I see you." The major challenge faced by Project Masiluleke could be captured in this local greeting – could Project M see the lives of the individuals they hoped to help? Could they find ways to understand each other and the individuals threatened by HIV/AIDS well enough to design effective solutions to a major health crisis? PopTech, frog design, and the Praekelt Foundation joined with iTeach, an HIV/AIDS and TB prevention and treatment program, to look for new approaches to address South Africa's health issues. Access to this case has been made freely available to the public.

Andrea Nagy Smith and Douglas Rae

Entrepreneurship, Operations, Social Enterprise, State & Society

JMB S.A. had been in the mango processing business since 1998, and CEO Jean-Maurice Buteau had built up a profitable business that exported around 2,000 tons of mangoes per year.  The January 2010 earthquake devastated Haiti, but JMB appeared to survive intact, and the Soros Economic Development Fund (SEDF) was eager to move forward. In spring 2010 SEDF proceeded with a $1.3 million loan and a $1 million equity investment in JMB. But by spring 2012, after pouring $2.55 million into JMB, SEDF realized that it had to make a decision: invest another $2 million and reorganize the company under new management; sell the company, or shut down JMB S.A. altogether.

Allison Mitkowski, Alexandra Barton-Sweeney, Tony Sheldon, Arthur Janik, and Jaan Elias

Customer/Marketing, Innovation & Design, Social Enterprise, State & Society, Sustainability

In 2009, SELCO was considering its plans for how the company might expand. The company decided to institutionalize its design process by building an innovation center. SELCO also added products that provided energy solutions beyond solar. Some within the company were hoping the company would go “deeper” and look at designing solutions for even poorer members of the Indian population. Others were hoping that the company would go “wider” and expand beyond its current geographical areas in Karnataka and Gujarat. Whatever its direction, the strategic choices the company made at this point in its evolution would be crucial to determining its continued success.

Andrea Nagy Smith and Mathew Spiegel

Asset Management, Investor/Finance, Metrics & Data, Sourcing/Managing Funds

In 2010 developer Bruce Becker completed 360 State Street, a major new construction project in downtown New Haven. The building was a 32-story high-rise with 500 apartments, a parking garage, and a grocery store on the street level. In the summer of 2013, Becker had a number of alternatives to consider in regards to the open lot adjacent to his recent construction. He also had no obligation to build. He could bide his time. But Becker also worried about losing out on rents should he wait too long. Under what set of circumstances and at what time would it be most advantageous to proceed?

Fawzia Ahmed, Jaan Elias, and Sharon Oster

Social Enterprise, State & Society

On the edges of a warehouse district in New Haven, Connecticut, an intrepid group of educational pioneers were turning conventional theory on its head. Amistad Academy, a charter school founded by two Yale Law School graduates, was not only getting students on par with their grade levels in reading and math, but was pushing them to perform as well as the best suburban school districts too.  Five years after opening Amistad, McCurry and Toll opened an additional school in New Haven and four schools in Brooklyn, New York – all of which showed the same promise as Amistad. They dubbed their network of schools Achievement First (AF), and garnered national attention and funding from “venture philanthropists” interested in educational reform. However, in the summer of 2006, AF was facing critical questions about its future direction.

K. Geert Rouwenhorst, Jean W. Rosenthal, and Jaan Elias

Innovation & Design, Investor/Finance, Macroeconomics, Sourcing/Managing Funds

In 2006 Deutsche Bank (DB) brought a new product to market – an exchange traded fund (ETF) based on the carry trade, a strategy of buying and selling currency futures. The offering received the William F. Sharpe Indexing Achievement Award for “Most Innovative Index Fund or ETF” at the 2006 Sharpe Awards. These awards are presented annually by IndexUniverse.com and Information Management Network for innovative advances in the indexing industry. The carry trade ETF shared the award with another DB/PowerShares offering, a Commodity Index Tracking Fund. Jim Wiandt, publisher of IndexUniverse.com, said, "These innovators are shaping the course of the index industry, creating new tools and providing new insights for the benefit of all investors." What was it that made this financial innovation successful?

K. Geert Rouwenhorst, Jean W. Rosenthal, and Jaan Elias

Entrepreneurship, Innovation & Design, Social Enterprise, State & Society

The political players had changed since President Clinton and Senator Moynihan’s helicopter ride. Clinton was no longer President, his wife had taken Moynihan’s seat in the Senate and Michael Bloomberg had replaced Rudolph Giuliani as New York’s Mayor. What remained the same was that the city, state, and federal government had yet to reach a deal. The question of what to do with Governors Island and who should do it remained very much open. Indeed, there were those within the new Bush administration and the Congress who believed in scrapping Clinton and Moynihan’s deal and selling the island to the highest bidder be that the local government or a private developer.

Jingyue Xu, Jean Rosenthal, K. Sudhir, Hua Song, Xia Zhang, Yuanfang Song, Xiaoxi Liu, and Jaan Elias

Competitor/Strategy, Customer/Marketing, Entrepreneurship, Innovation & Design, Investor/Finance, Leadership & Teamwork, Operations, State & Society

In 2015, Ant Financial’s MYbank (an offshoot of Jack Ma’s Alibaba company) was looking to extend services to rural areas in China through its Flourishing Farmer Loan program. MYbank relied on the internet to communicate with loan applicants and judge their credit worthiness. Initial tests of the program had proved promising, but could MYbank operate the program at scale? Would its big data and technical analysis provide an accurate measure of credit risk for loans to small customers? Could MYbank rely on its new credit-scoring system to reduce operating costs to make the program sustainable?