You Look or Dress”
learned to spot and
combat natural bias
to raise money
for his mobile app.
When Tony Aguilar left Pecos, Texas, to
attend college about 15 years ago, he headed
to Indiana University, opting against Ivy
League schools in favor of keeping a low
profile. Despite having a father who constantly
instilled confidence, Aguilar had doubts about
where he belonged.
TONY AGUILAR “There can be extreme bias going into these conversations.”
chosen by the venture capital firm 500 Startups
as one of 16 companies — out of 2,500 startups
worldwide — to participate in the firm’s “Batch
23” accelerator event.
“We raised $1 million in the pre-seed round,”
Aguilar says. One of the round’s early investors
was Dan Macklin, MS ’ 11, a Stanford MSx alumnus
and a cofounder of SoFi, one of the biggest student
loan refinancing companies. He was followed by
Fabrice Grinda, Forbes magazine’s no. 1-ranked
angel investor in the world.
Despite such endorsements, Aguilar believes
some VCs approach a meeting with a minority
CEO differently than they might other wise.
He came to that conclusion after reading
a study in Harvard Business Revie w about the
different types of questions male and female
entrepreneurs are asked by VCs — and how it
affects the amount of funding each receives.
Women tend to be asked questions about the
potential for losses in their business, while non-
minority men tend to be asked about the potential
for gains. The research resonated with Aguilar.
“It opened my eyes,” he recalls. “I’ve
experienced the same thing as a minority, and it’s
something I’ve discussed extensively with other
Entrepreneurs who are asked about the
potential for gains — or who are able to “flip”
a question about potential losses into a discussion
about potential gains — tend to raise significantly
more funding than those who field and answer
questions on potential losses, Aguilar notes.
“There can be extreme bias going into these
conversations,” he says. “Now, when I’m asked
questions in a pessimistic tone, I answer in an
optimistic way. You have to learn tactics like
that, because you don’t always know that it’s
happening. For a lot of entrepreneurs, it’s hard not
to take it personally, and it can make you second-
guess whether you have what it takes.”
Aguilar cites persistence and outreach as keys
to his successful financing efforts.
“The only way to do this is to ask for help,
and Latino males don’t do that,” he says. “But
networking is incredibly important. As Latinos,
we tend to create cliques; we stick with other
Latinos, and we can’t be doing that. The VC world
is run by white males, and most are not bad or
biased. It’s a matter of opening your network,
asking for help, and getting into the same room
with the people who can really change the
trajectory of your company. Knowing that there
will be bias at certain times, learning to adjust to
it in a meeting, and taking control of it.
“If we want to make an impact, we need
to get into those pockets,” he adds. “If they
like you or don’t, ask them who they know
who would be excited about your company.
If you continue to get those doors open,
opportunities will open up.” Δ
“I was a first-generation high school
graduate, and I looked and dressed very
different from most of my peers,” he recalls.
“I decided to go where I thought I’d fit in.”
Today, Aguilar should fit in just about
every where. He’s the 33-year-old founder of
Austin-based Chipper, a thriving mobile app
startup that allows student loan recipients
to manage, pay, and refinance their school
debt in one place. But even though his
company manages $150 million in student
loans, Aguilar still feels that he’s sometimes
perceived negatively by investors.
“Raising financing has always been very
challenging,” he says. “A lot of VCs have
preconceived notions regarding how you
look or dress. They’re natural biases. And it’s
frustrating to experience that.”
The founder and former CEO of Student
Loan Genius (the first student loan benefit to
allow companies to help employees pay down
their student debt), Aguilar launched Chipper
in August 2018, after the company was J u