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Fridays from the Frontline: My Three Failures—So Far


This week’s Fridays from the Frontline comes to us from just across the river at the University of Pennsylvania’s Wharton School. Its author, Divinity Matovu (WG ’17), first appeared in this column last year sharing about MBA Mama, an online platform she co-founded with Fuqua MBA student Nicole Pontón as a resource for women pursuing their MBAs while also balancing motherhood. (Full disclosure: Clear Admit has since entered a partnership with MBA Mama to share relevant content between our audiences.)

As she details in the following post, Matovu is at it again—this time launching a new technology startup designed to help busy parents exchange babysitting services within trusted networks. Called Watotolly, her venture has seen some successes recently, ranging from its acceptance into Wharton’s Venture Initiation Program to growing interest from investors to a 700+ percent increase in page views for its website. Despite all this, Matovu devotes her blog post not to successes, but to failures—three failures she terms “epic” that have helped her reach this point. Read on to learn how failing can teach as much—if not more—than success. Our thanks to Matovu for sharing her experience with the Clear Admit audience.

The following post has been republished in its entirety from its original source, the Wharton Entrepreneurship Blog.

My Three Failures—So Far

By Divinity Matovu, WG ’17

I was inspired to write this blog post after one of my Wharton classmates, Chris Griggs, wrote an article about failure during business school. In the last two weeks, I’ve made a lot of positive progress on my start-up Watotolly, a technology company that offers busy parents the ability to connect and exchange babysitting services within trusted networks. Part of my progress has come through hard work, grit and hustle. The rest can be attributed to luck, being in the right place at the right time, and the privilege and access my Ivy League education is affording me.

Yesterday afternoon, I got a rejection email from WeissLabs, a student-run startup incubator whose mission is to catalyze innovation by engaging students through lessons, community, and mentorship—leveraging resources across the University of Pennsylvania to foster entrepreneurship. I already had a hunch that I did not get into the incubator because other entrepreneurs in the Wharton community had received interview invites and I had heard nothing. Nevertheless, my heart sank as I read the first couple lines of the rejection email:

“Unfortunately, considering our number of applications and limited spots, we cannot accept your company into WeissLabs at this time.”

Entrepreneurship is as much about resilience and bouncing back from failure as it is about innovation and value creation. I realize I have to be prepared to hear 999 no’s along my journey before I get the one yes that could catapult my company to the next level. I have a BHAG: big hairy audacious goal, which is to use tech to revolutionize how we live, work and care for our children. Big picture: I want to build Watotolly, create value, sell my company and use the acquisition proceeds to start my own venture capital fund focused on financing female and under-represented minority founders. I’ve repeatedly said I want to work at the intersection of tech, entrepreneurship and venture capital. At best, my vision is grandiose and—statistically—nearly impossible given that I’m a black girl from small town Wisconsin who grew up on food stamps in public housing. At worst, I am batshit crazy to forego a “stable” career path earning $120-150K post-MBA.

In the past week, I’ve shared news about securing a new advisor, getting accepted to Wharton’s Venture Initiation Program, meeting with investors and an amazing 700+ percent growth in page views of Watotolly.com. The validation I receive when I signal boost my accomplishments feels warm and fuzzy. But entrepreneurship is a challenging—often lonely—path that is full of rejection and uncertainty. As I reflect on my decision to pursue this path, I wanted to share three of my most epic failures.

Failed marriage. Age 28.

three failures

Being taken care of by my girls on my wedding day.

I met the man who would become my husband in August 2008 when I was 22. I had graduated as a first-generation college student three months earlier and decided to pour my life savings (approximately $2800) into a continental move from California, USA, to Kampala, Uganda, to work in the non-profit sector. I met my partner in Uganda in August and by November (of the same year), we were engaged. I got married in 2010 at the age of 24. I filed for divorce on April 24, 2014. The reasons for my divorce are complicated. If I wrote them out, I’d be biased and unfair to my ex-husband who is—at his core—a kind human being with good intentions. Long story short: I failed at marriage.

Failed start-up. Age 26.

I created the Amagezi Gemaanyi Youth Association (AGYA) in 2008. My co-founder and business partner was my boyfriend, later my husband and now my ex-husband.


The first flyer we created to explain AGYA’s programs in spring 2009.

While AGYA made a significant social impact through food and nutrition, arts enrichment and education programs that served hundreds of children living in extreme poverty, our business model was not sustainable. We were too dependent on grants and individual donations and had no long-term strategic plan for generating revenue. I was young, naive and idealistic about almost everything related to the business. I did not have the professional network, resources, education, business acumen or access to capital to create a sustainable model. Despite three years of operations, I made the difficult decision to close the doors to our community center. I was six months pregnant at the time and had no clue what my next career move would be. Long story short: I’ve been a failed founder.

Failed to get admitted to Stanford GSB. Age 29.

My failed start-up spurred me to consider a graduate business degree. Given my blind spots, the personal and professional development I would get in a top-tier MBA program could change the trajectory of my career and significantly increase my lifetime earning potential. I had the entrepreneurial bug and Stanford was at the top of my list. The school’s reputation is excellent and it is (arguably) the # 1 business school in the country. Based on my research, Stanford also has some of the most comprehensive resources for student parents among any top-10 program, which was particularly relevant to me as a newly single mom.

Furthermore, as someone interested in tech, VC and entrepreneurship, the location in Silicon Valley was very appealing as well. I was already living in Los Angeles managing my own consulting practice, so a move to Palo Alto would have been ideal. I did all my due diligence, studied hard for the Graduate Management Admissions Test, completed pre-MBA fellowships with the Forte Foundation and Management Leadership for Tomorrow and put together what I thought was a rock-solid application. I applied to schools like Cornell, Stanford, Wharton and Babson—a small but mighty program in Boston that has the top-rated entrepreneurship program in the nation. I was admitted with sizable financial awards to all but one of these schools. I was absolutely crushed when I did not get admitted to Stanford. Not only was I not admitted, but I did not even receive an interview invite. Long story short: I failed to gain admission to a top-ranked MBA program.


Me in fall 2014, high off the kool-aid at GSB’s Diversity Weekend with my good friend, John, who is currently at Univ. of Chicago’s Booth School of Business.

Intelligent Failure + Pressing On.

To re-cap, before I turned 30, I had a failed start-up, a failed marriage and a confidence-crushing admission rejection. My latest rejection from the WeissLabs incubator pales in comparison to the epic fails I’ve shared in this blog post. Yet somehow, the sting of rejection is still there. So far, I’ve always managed to bounce back during these ebbs and flows of big risk-reward tradeoffs. Currently:

  • I am dating a guy who makes me feel butterflies in my stomach.
  • I am working on a start-up that I believe will change the world.
  • I am having the most fulfilling, challenging, and rewarding educational experience at Wharton, a program that is without a doubt the best place for me to be for my MBA.

During pre-term orientation, a Wharton professor told us that we should aim for “intelligent failure” and stretch experiences that would push us out of our comfort zones. Coined by Duke University’s Sim Sitkin, “intelligent failure” describes a process to manage, mitigate and learn from failures. Sitkin’s view is that embracing failure sets the psychological environment for innovation and creativity to flourish. I personally love the Gretzky quote: “you miss 100 percent of the shots you don’t take.” I’m currently dating an awesome guy who could totally break my heart, and I’m working on a start-up that could totally fail. But—in the spirit of Sitkin, Gretzky and so many others who have failed on the way to success—I am encouraged to keep pressing on with humility and resilience. I am slightly older and slightly wiser and will use these life lessons to make better, more informed and thoughtful choices that will set me up for success. Worst case scenario, I am diving headfirst into failing intelligently in this next venture and phase of my life.

Pictured at top: Matovu at Temple University’s League for Entrepreneurial Women’s Conference with Lori Hermelin Bush, an angel investor, former CEO & President of Rodan + Fields and retired executive at Johnson & Johnson.

Posted in: Fridays from the Frontline, MBA Mama, MBA News, News, Weekly Columns

Schools: Stanford GSB, UPenn / Wharton

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