8

Rating ? Qualities ?
Eye Opening
Engaging
Inspiring

Buy book or audiobook

Digital Goddess
The Unfiltered Lessons of a Female Entrepreneur
Victoria Montgomery Brown • HarperCollins Leadership © 2020 • 272 pages

Leadership / Business Leaders

Women in Business / Women’s Careers
Society / Women’s Economic Empowerment

Take-Aways
• Entrepreneurs should never lie to their investors – even if they just got arrested.
• Women entrepreneurs have a tough time raising start-up capital.
• Women entrepreneurs must have the attitude that they, “will stop at (nearly) nothing to get it done.”
• Starting a company and transitioning to the role of boss is challenging. Work with people you like.
• Despite myriad difficulties, being a female founder and CEO does have advantages.
• Managing a business partnership resembles a marriage. Entrepreneurs should avoid divorcing their
business partners.
• Women CEOs must be careful not to let their business undermine their health.

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 Recommendation
Victoria Montgomery Brown candidly covers the highs and lows of being a female entrepreneur. Brown and
co-founder Peter Hopkins started the online firm Big Think, which offers short, informational videos made
with leading experts. Brown begins with how a vengeful ex-boss got the police to arrest her, and why you
must be transparent with investors about everything, including a criminal record. She tracks issues women
entrepreneurs face with raising funds, being the boss, maintaining partnerships, handling sexism, and
more. To warn and encourage female executives, Brown hits each facet of starting and leading a company.

Summary

Entrepreneurs should never lie to their investors (even if they just got arrested).

Victoria Montgomery Brown, co-founder and CEO of Big Think, worried her company would fall apart when
the New York City Police (NYPD) called her to a midtown precinct and arrested her. An amused detective
said she’d angered some powerful people.

Her arrest had roots in the past. In 2003, right after completing her MBA from Harvard Business School,
Brown went to work for a major television journalist, “Mr. Snider,” who had a prime-time show. A friend
and Harvard classmate introduced her to Snider. After she freelanced for several months, Snider hired
Brown the night before Thanksgiving. She worked for him as a producer who booked guests, including big
names in entertainment, fashion, politics and business.

After six months, Brown became a recruiter seeking Ivy League graduates to work for Snider, who had an
obsession with Harvard. In the spring of 2004, Snider hired producer Peter Hopkins, a Harvard grad. Brown
and Hopkins instantly clicked; he was tall, handsome, gay and funny. They created a parody website called
WASPdate. Wanting to produce something more thoughtful, they decided to create Big Think, an online
business featuring smart, educational interviews with leaders and experts. As they envisioned it, it would
resemble the brainstorming World Economic Forum in Davos, Switzerland, but it would be online for
everyone.

“I’m not going to lie; I think that it’s likely even more important for women to show that
they are all in. From the investors’ perspective (perhaps unjustifiably so), it’s a risky
enough concept to invest in a female founder, so she had better show that she’s totally
committed and will stop at (nearly) nothing to get it done.”

Brown and Hopkins secured $1.4 million in start-up funding for Big Think and quit their jobs.
Snider, supportive, threw a going-away party. He asked Brown what she’d miss about working there, and she
joked, “The car service!” not knowing that would lead to her arrest a year later. Snider told the NYPD that
Brown used the company car service after he no longer employed her. That was true. She had continued to
do small tasks for Snider to maintain their business relationship. The police let her leave, but Brown feared
telling her investors.

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 She and Hopkins called their early investors, including David Frankel and economist Larry
Summers, president of Harvard and former Treasury Secretary under Bill Clinton. Though the NYPD
charged her with grand larceny, both investors supported her. She thanked them and promised Big Think
would continue. Honesty strengthens relationships; deceit erodes them. Brown and Hopkins called all of
their major investors about Brown’s arrest. She got Peter Schaffer, a criminal defense attorney, to represent
her. Snider never dropped the case. Schaffer negotiated a plea deal of two days of community service with no
criminal record.

Women entrepreneurs have a tough time raising start-up capital.

Gaining your initial investment is hard because even interested investors won’t invest until other investors
put money up, particularly with female start-up founders. On April 7, 2007, Brown and Hopkins signed their
paperwork and were officially in business. One round of funding wasn’t enough for Big Think. They raised
$1.4 million, but spent it quickly creating a website, booking talent, creating written content, and shooting
and editing video interviews. Because of the tough economy, they sought private investors, who were
usually older, white and male. A Boston Consulting Group study reports that even though women-run
start-ups receive less initial funding than male-run start-ups, they eventually make more money. Women
entrepreneurs generate $0.78 in revenue for every $1 raised compared to men who generate $0.31 for every
$1 raised.

“There have been times when I could have compromised my own principles because we
needed the money or the sale or whatever, but in the end, my self-worth and integrity
have always mattered more. This is a line I’ve walked my entire career.”

Still, women face questions few people ask men. They must answer risk avoidance questions, which deal
with safety and possible loss. In contrast, investors ask men promotional questions that address their
accomplishments and objectives. Brown notes that her having attended Harvard made investors take her
more seriously than they might have otherwise – not as seriously as men start-up leaders, but more seriously
than other women.

Women entrepreneurs must have the attitude that they “will stop at (nearly) nothing
to get it done.”

Entrepreneurs should work on their business daily and fulfill a variety of functions. Brown and Hopkins
hired an accountant, two employees and freelance videographers. Brown was founder, CEO, HR officer,
agent, reporter, gofer and more. In Big Think’s early days, she and Hopkins lined up speakers to feature on
their website: science author Steven Pinker, business author Michael Porter, and the late business strategist
Clayton Christensen.

“Don’t become paralyzed by the enormous list of tasks ahead of you. Do something every
day to further your objective. Every step matters. It doesn’t have to be a great big task,
like writing a business plan.”

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 All entrepreneurs need mentors, but they’re a particular benefit for female entrepreneurs. Brown turns
to senior male executives for candid feedback and has worked with female mentors though women are
unusual in the start-up world. One mentor, serial entrepreneur Carla Newman, shared lessons she learned
as the only woman in the room and told Brown how she coped with male egos. Brown urges women to
find female mentors, but reminds them that they are a rare breed. Larry Summers, an early investor,
became Brown’s mentor and friend. Brown believes a mentor should give honest and critical feedback.
Entrepreneurs should be able to ask their mentors for help when they need it.

Starting a company and transitioning to the role of boss is challenging. Work with
people you like.

Bosses have to deal with hiring, managing and – with employees who aren’t a good fit – occasionally
firing people. Brown learned that entrepreneurs should hire slowly and fire quickly. She had her share of
offbeat personnel problems, including dealing with a junior editor who had smelly feet. She approached
him in a non-threatening way and used herself as an example. Earlier in her career, she’d learned that her
perfume made some people feel ill. She stopped wearing it. Tapping into that experience, she encouraged the
editor to wear fresh shoes to spare his nearby colleagues. Her approach resolved the problem.

“One of the biggest mistakes I’ve made is not getting rid of toxic people quickly enough.
And also, hiring people when I had even an inkling they may not work out.”

Brown learned the hard way that entrepreneurs should be aware of their own confirmation bias. She
wanted to hire mostly Ivy League graduates, but made mistakes with at least two of them, especially a
woman referred to here as Lucy. Lucy was a smart, sassy writer, but suffered from feeling entitled. Brown
hired her despite sensing possible friction. Though good at her job, Lucy was sarcastic and acted miffed
about doing tasks she found menial. Brown thought perhaps she didn’t like working for another women.

In May 2008, Lucy was still at Big Think, but other team members privately approached Brown and
Hopkins about problems with her. Hopkins fired her after Lucy wrote inappropriate headlines on their
website that almost cost them a major sponsor. Lucy screamed, and wept and hid in a broom closet. That
evening, Brown checked her email and discovered Lucy had called her a foul name and referred to her as
“Liquid Nitrogen” in an email sent to all staffers and possibly external people. Big Think expert Bill Eddy
identifies Lucy and her ilk as toxic, high-conflict people who create drama by blaming others and playing the
victim instead of resolving problems.

No person is necessary if he or she fosters a toxic work environment. Roger, another HCP, was with Big
Think from the company’s inception and became COO. Things started falling apart a few years later; Brown
didn’t want to fire Roger because she worried two other employees might quit if she did. Three staffers told
Brown independently that Roger was so toxic they would quit if he weren’t fired. She and Hopkins found
that Roger had withheld and hoarded information to make himself indispensable. Brown called him at 9:30
p.m. and angrily fired him.

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 Despite myriad difficulties, being a female founder and CEO does have advantages.

Women should own their power and embrace their femininity. They shouldn’t try to act like men to
succeed. Vulnerability is a sign of strength, not weakness. Women entrepreneurs have to deal with
the sexism inherent in business, but sometimes being the only female in the room can be an advantage. No
company or person should tolerate sexual harassment. Brown had to brush off minor offenses – usually
from men 65 and older; she believes that older men went through most of their professional lives with only
subordinate women in the workplace, if any. Ideally, older men should change their behavior but it doesn’t
always happen.

While Brown acknowledges that she might need to be harsher with men who made misogynistic or
demeaning comments, she decided to do what she felt was best for her company without undermining
her values. She deflects inappropriate comments with humor, which she finds is a more effective tool than
outrage. She once wore a pair of fashionably ripped jeans to a summer party. An older man she knew in
banking offered to buy her a new pair without rips. She laughed and said she’d email him some suggestions.
Another man overheard and told Brown he thought she handled that situation well. He became an adviser
to Big Think. Women CEOs must decide they are worthy of commanding the same attention as a male CEO
and act like it.

“I’ve learned along the way to ask for what you want. Be fearless. The only downside is
a no. As our lead investor constantly said to me: ‘You don’t ask, you don’t get.’ Women
sometimes have a tough time asking. Go for it.”

In 2018, women leaders ran only 4.8% of Fortune 500 companies, received only 2.2% of US venture capital
($2.3 billion out of $96.7 billion), and earned only 80 cents for every dollar a man made, a collective loss
of more than $500 billion. Brown believes that women leading their own start-ups –rather than becoming
employees at an entrenched company – have excellent opportunities to change these conditions.

Managing a business partnership is a lot like a marriage. Entrepreneurs should avoid

divorcing their business partners.

Brown finds romance elusive. She married, but eventually divorced, because she was married to her job.
Her business partnership with Peter Hopkins endures. Successful business partners complement one
another: Brown, the pragmatist and decision-maker, balanced Hopkins, the creative visionary and optimist.

Brown and Hopkins confronted two major issues that could have wrecked their partnership. In December
2007, while Brown was reeling from her unfair arrest, Hopkins received a positive diagnosis of HIV. They
hugged, cried and vowed to carry on. When Hopkins took a few days off work, she called him often to check
on him. In 2013, Hopkins’s creative behavior turned erratic and dangerous, but Brown refused to confront
him. He swung back and forth between being aggressive toward staff members and ignoring them. Right
before a big event, Hopkins wanted to scrap the program and start over. Her employees warned Brown not
to let him attend, and she learned he’d become addicted to crystal meth. After the event, the entire staff
threatened to quit if Brown didn’t stage an intervention.

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 “When you commit to a business partner, it’s more than just business. Your success
becomes dependent on your partner’s success, and vice versa.”

Brown acknowledges that she and Hopkins had become codependent, but she finally confronted him. She
told him he couldn’t report to work, manage staff or handle projects until he was clean. Hopkins was angry,
but he knew she was right. He went through rehabilitation and came back better than ever. Hopkins, in turn,
gave Brown a high level of support when she went through her own health crisis.

Women CEOs must be careful not to let their business undermine their health.

Brown arrived at Mount Sinai Medical Center in New York, convinced she was having a stroke despite being
in her early 40s and relatively healthy. After many tests, she discovered she’d had a panic attack. Earlier,
she’d had several smaller breakdowns and once almost passed out during a board meeting. Brown’s anxiety
was affecting her physically. She would get dizzy getting into cars or planes and while imagining worse-case
scenarios. By the spring of 2016, after nine years of running the business, she could tell her mental health
was deteriorating. In that time span, Brown had dealt with a divorce, the end of a long-term relationship and
the death of her mother.

“Mental health is a topic that’s often left out of the start-up conversation. But it shouldn’t
be. Stress and anxiety are familiar states to most founders, and we rarely speak openly
about how we deal with them.”

Hopkins told her she needed professional help. In addition to therapy, Brown took prescription medication
to manage her anxiety and depression. However, anxiety and depression have no magic cure. Brown
used different techniques to help herself, including medication, reading relevant books such as Creative
Visualization by Shakti Gawain, and participating in a week-long, off-the-grid therapy retreat. She feels
she learned life lessons that are connected to her work, and she cautions other entrepreneurs to guard their
health and well-being.

About the Author

Victoria Montgomery Brown is the CEO and co-founder of Big Think, an online company that offers
short informational videos featuring leaders and experts.

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