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“Raising children isn’t scalable,” according to Jacob Lief,
the founder of the , a holistic “cradle to career” education and health organization
for orphaned and vulnerable children in Port Elizabeth, South Africa.

Ubuntu seeks to provide “what you would give your own
children,” Lief explained, “what all children deserve – everything.” Many funders, while well-intentioned, he observed,
are quick to make judgments about things like overhead costs and “scale” that are
inconsistent with transforming lives. In
the case of Ubuntu, “impact” is achieved by going “deep” and working with a
child over many years, in many ways.
It’s not cheap.

Lief, author of the new book , spoke at a recent event at ������Ƶ NYC of his
experiences as a social entrepreneur, among them what he has learned about the
world of philanthropy. What Lief would rather see, as he described in
conversation with president Cheryl Dorsey, president Liz Luckett, Karim Abouelnaga, the founder and CEO of
Practice Makes Perfect, and ������Ƶ Senior Fellow Georgia Levenson Keohane,
are funders, and by extension the organizations they sponsor, willing to cast a
wider net and take a longer view. That means supporting projects that produce
experiences—like education, mentorship, and emotional support—that are sometimes
hard to measure in one bottom line.

Metrics matter, of course.
Take the case of Donors Choose, a successful and fast growing
organization that allows public school teachers to request resources from
donors online; today, only fourteen cents for every dollar go to overhead and
that number decreases every year because they are more efficient. While these types of models are important, Lief
noted, they are not always the right benchmark for all nonprofits; many must
make larger investments in people and organizational capacity to achieve their
mission.

The other discussants noted similar tensions and
contradictions in the way organizations must raise “capital” to address
entrenched social and economic problems.
“We have a structural problem that for those of us who run nonprofits,
quite often our customer is different than the constituents we serve,” said
Dorsey. Her organization, Echoing Green, focuses on social investment,
identifying and supporting social entrepreneurs like Abouelnaga, an Echoing
Green fellow working to through summer enrichment programs for students in
Kindergarten through 8^th grade.
“We are pulled in different directions and it totally distorts the
marketplace,” Dorsey said.

Many new philanthropic donors are coming from places like
Silicon Valley that have embraced risk, innovative thinking, and even failure.
Yet, despite relentless focus on things like cost, these business principles
are sometimes thrown out the window when the individuals who have mastered them
donate for the social good.

“If I tell one person about a pilot initiative that didn’t
make it, I may lose my funding from them,” said Lief. “It doesn’t make sense.” And indeed sometimes nonprofits should be
treated more like for-profit companies. If an organization reaches its goals,
isn’t that most important?

That blurring of nonprofits and for-profit companies is
already happening in the world of social entrepreneurship. Dorsey said that
before 2006, all of the business plans her organization saw were for
traditional nonprofits. But in 2007, they began to see a rise in for profit or “hybrid”
organizations seeking grants. “50 percent of our submissions have double bottom
line or triple bottom line businesses” she said.

Indeed most companies have some kind of “impact,” noted
Luckett. Etsy, for example, allows people to become entrepreneurs; Uber has
created more efficient transportation; cellphone operators have helped to build
a mobile money industry. As an impact
investor, Luckett is looking for companies around the world that purposefully
set out to create access to these kinds of products or services for underserved
populations – start-ups like Pigeonly, a provider of low-cost communications
between inmates and their families, or Liberty and Justice, a fair trade
apparel manufacturing firm in Liberia.

The bottom line for the speakers was that philanthropy
doesn’t fit into neat categories. Impact isn’t restricted to nonprofits.
Innovation shouldn’t only be the realm of large corporations. Investments need
to be strategic everywhere.

And perhaps the most important quality to both nonprofits
and for-profits is leadership. “We need to do more in our sector to not only
tolerate failure but to celebrate it or embrace it, especially with the younger
generation,” said Dorsey. When her company selects leaders to support, one
quality they look for is resilience. “We know you are going to fail,” she
observed. “It’s about the journey.”

Just like raising children, fostering
true leaders isn’t scalable—and their journeys aren’t always straightforward.