i.Lab Alums Relish and Totem in the News

Sarah Rumbaugh is all of 30 years old, and part of a generation that, as she puts it, “will struggle to do as well as our parents, no matter how well-educated or how hard-working we are.”

So, at the helm of her own tech startup, Relish (operator of RelishCareers.com), she’s taken Sheryl Sandberg’s advice to “lean in” under advisement, but with her own set of internal reservations.

Last week, in between work trips to New Orleans and Miami, Rumbaugh closed on the acquisition of a competitor of sorts, Chicago-based TransparentCareers.com.

“If anything, I envisioned us being acquired by somebody,” Rumbaugh said in a quick interview before she raced off to Miami. “Never did I think we would acquire another company.”

Back in March, Rumbaugh heard that TransparentCareer.com, a Glassdoor.com-type of startup incubated at the University of Chicago’s b-school, was looking to be acquired. She chatted with the founders a couple of times over the course of March and April, then engaged the Charlottesville office of Woods Rogers PLC to look under Transparent’s hood (or “open their kimonos,” or whatever other cliché you prefer for the due diligence review of a company’s financials and business processes).

Satisfied with what they saw, Rumbaugh and her cofounder, Zach Mayo, acquired the company in exchange for an undisclosed percentage of Relish’s shares.

In our interview, we talked about how Rumbaugh thinks about risk — both personally and professionally. She acknowledges that acquiring another company layers some additional risk on top of the gamble she is taking by starting her own company instead of pursuing the corporate career paths that so many fellow MBA graduates follow.

“But that path is a risk, too. It’s strong, financially-speaking, but it doesn’t give you independence or flexibility in raising a family or trying new things,” Rumbaugh said. “If Bill Gates or Steve Jobs did a quantifiable spreadsheet about whether they should have started Microsoft or Apple, the answer would have been no. You can’t quantify what makes you happy.”

For a moment, Rumbaugh borrowed from the Darden-born idea of “effectuation,” a framework for making business decisions amidst uncertainty. “It helps me to put all the risks in a box,” she said. “Once I know all the possible outcomes, and what my ‘affordable loss’ is, the feeling of risk really goes away.”

To be fair, the box of risks she described still sound pretty perilous.

“If this path doesn’t work out for me, I’ll have less savings and I’ll have missed out on my 20s and potentially waited too long to have a child,” she said, while one of her adopted Viszlas nuzzled near her desk.

Right now, she said, although she rejects the “premise” of Sandberg’s tome — “she’s saying it’s OK to work 15 hours a day and hire a babysitter to take care of your kids” — Rumbaugh is willing to do whatever it takes to build her company.

She’ll spend the next 12 months figuring out whether and how to integrate Relish and Transparent’s operations and branding. After that, she’ll figure out her personal path.

Totem Systems

Another group of young local upstarts — which includes a former Woods Rogers associate, coincidentally — just landed a $200,000 round of seed funding for their tech startup, Totem Systems.

The undisclosed investor received a 10 percent stake in the company.

The Woods Rogers connection is COO PJ Harris, who graduated from the University of Virginia School of Law just two years ago. Harris and a couple of co-founders created their first startup, RouteMine — which created custom running and biking routes based on your previous routes — during the summer after his first year of law school at the UVa i.Lab.

He cofounded Totem Systems the following summer, along with Kyle Matthews, Danny O’Donnell and Alan Wei (the CEO, who also co-founded RouteMine).

Totem’s software helps nonprofits manage fundraising, events, social media and volunteer efforts. The name was chosen because a totem pole is a symbol of collective identity and the idea that we are all more compelling, more complete and more powerful together. (To wit: Donald Trump apparently reversed course on his family-separation policy after just days of collective uproar.)

Harris announced the deal on Facebook, noting that it closed the same day Monticello opened six new exhibits featuring the lives of Jefferson’s enslaved families. Harris's great-great-great grandmother, Eliza Coleman, was a slave at Monticello, he wrote.