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Inside Serena Williams’ Plan To Ace Venture Investing

 

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n Serena Williams’ calendar—which is to calendars what Jackson Pollock paintings are to art—Saturdays are designated family time. The Saturday I’m with her in Rome (she was in New York earlier in the week and will be in Paris the following one) carries extra significance. Exactly four years ago, in exactly that Eternal City, she met her husband, Alexis Ohanian, cofounder of online community Reddit.

The two celebrate, in part, with the kind of outing anyone who’s not the most famous woman athlete in the world takes for granted: a stroll in a hotel garden with their joint venture, 22-month-old Olympia, in tow. It’s more romantic than it sounds: The Rome Cavalieri goes so far as to call its 15-acre garden a “private park,” littered with marble and bronze, lions and unicorns.

The regal surroundings befit a historic figure of American sport, who has 23 Grand Slam titles and has blown away any number of barriers and stereotypes. And the unicorns? Between Reddit and his $500 million fund, Initialized Capital, Ohanian does his part. But it turns out that Williams has quietly been playing that game, too. She’s now the first athlete ever to hit Forbes’ annual list of the World’s Richest Self-Made Women, with an estimated fortune of $225 million, the vast majority of it having come via her brain and brand rather than her backhand. And over the past five years, she’s been quietly dropping money into 34 startups. In April, Williams formally announced that Serena Ventures is open for business, to fund others and launch companies herself.

Athletes are richer than ever, thanks to the explosion in TV rights fees for live sporting events, which trickle down to players. The 50 highest-paid athletes in the world made $2.6 billion last year, versus $1 billion 15 years ago. And Williams is hardly the first to put newfound disposable income to active work—in the NBA alone, LeBron James, Stephen Curry and Kevin Durant have all launched media companies, and Durant, Andre Iguodala and Carmelo Anthony are active venture capital investors. But she is one of the few specifically gearing investments around a single north star: herself.

“I want to be a part of it,” she says, sitting at the hotel. “I want to be in the infrastructure. I want to be the brand, instead of just being the face.” Given her longtime background in style and design, that means overweighting on fashion lines, jewelry and beauty products. Yes, she’ll keep competing at tennis—her resilient comeback last year after giving birth burnished her as a cultural icon who transcends sports. And sure, she’ll happily continue to rake in easy endorsement money from the likes of Nike and JPMorgan Chase—her $29 million total income over the past 12 months is the highest of her career.

But like a ground stroke with torque, Williams bets she can eventually dwarf those figures by leveraging some of her own cash with her name and fame.

The story of how sisters Serena and Venus Williams reached the top of the tennis world is the stuff of Hollywood legend: a black father with limited tennis experience homeschools his two daughters and teaches them on the streets of Compton, California, to penetrate and then dominate a lily-white sport. “You’d see different people walking down the street with AK-47s and think, Time to get in the house,” she remembers of those early years. “When you hear gunshots, you get low.”

Their father’s insistence that his precocious daughters avoid the private tennis academy machine and well-oiled junior tournament circuit left a mark on the younger one, especially after she won her first Grand Slam title at age 17. “It really shaped me for the rest of my career both on and off the court in terms of taking a chance and how to be different and how to stand out,” Williams says of his strategy. When everyone zigs, she zags.

So at Serena Ventures, she focuses on companies founded by women and minorities. Yes, there’s a social purpose to that decision. But as with her tennis upbringing, she’s also finding opportunity by avoiding the herd. Just 2.3% of the total venture capital invested last year in the U.S. went to women-led startups—and even when including firms with both a male and female founder, you’re just at 10%. The numbers are worse for black and Hispanic founders. Yet some 60% of Williams’ investments so far have gone to companies led by women or people of color. “What better way to preach that message?” asks Williams.

The only way to find enough of those companies right now is to nurture them early, something that Williams got hooked on after investing and losing (eventually) $250,000 in a startup in the years before Serena Ventures. “I learned you can’t overspend, but I also learned that I love seed investing,” she says. Of the 34 companies she’s backed through Serena Ventures, more than three quarters are early-stage.

“It’s fun to get in there. I don’t gamble. I don’t jump off buildings,” says Williams. “I’m the most non-taking-a-chance kind of a person, but I felt like seed was where we wanted to be.”

Given the exponential riskiness involved in pre- and early-revenue companies, Williams has built a team of Silicon Valley mentors around her, much as Patrick Mouratoglou has guided Williams on the court and WME’s Jill Smoller has handled her endorsements—almost a quarter-billion worth—for nearly two decades. There’s Chris Lyons, from Andreessen Horowitz, who is an informal advisor and friend. “She is more passionate than 99% of the people in this space,” says Lyons. “She’s reaching out to me regularly asking what we think of companies.”

There’s Facebook chief operating officer Sheryl Sandberg, a longtime friend, with whom she serves on the board of SurveyMonkey. “I always ask her advice in a lot of different areas,” Williams says. (The tennis star is also on the board of the social shopping platform Poshmark.)

But one mentor stands above the rest—the one she married. “I’ve been really leaning on Alexis,” she says. Williams had never heard of Reddit when the pair met in 2015 and Ohanian knew little about tennis. But they bonded over ambition. “She is determined to be great at everything she does,” says Ohanian, who Forbes estimates is worth $70 million on his own.

What Serena Williams Wants To Hear In Pitch Meetings| 32:11

His venture firm’s targets are traditionally more tech-focused—big scores include Instacart and Patreon. But in living through Ohanian’s deals, Williams has learned. Initialized and Serena Ventures have even co-invested on a few, including Gobble, which does weekly dinner-kit deliveries, and Wave, which offers no-fee transfers on money sent to Africa by phone. “I’d like to call us a more modern business family,” says Williams.

The rate of Williams’ investments has ramped up in lockstep with the onboarding of a portfolio manager. Alison Rapaport, 29, was fresh out of Harvard Business School with an M.B.A. after a five-year stint in JPMorgan’s asset management group, when she got connected with Williams through Andreessen’s Lyons. Williams told Rapaport to come to the interview with three investment ideas, along with the numbers and rationale behind them. Rapaport did her homework on the investment ideas—and diligence on her potential new boss, who earlier in the week posted on Instagram how much she liked Taco Sunday. Rapaport arrived at Williams’ home outside San Francisco for a Sunday meeting at noon armed with investment ideas and two bags of takeout, make-your-own tacos, and she handled Ohanian’s rapid-fire follow-up emails with aplomb. “I knew this was our girl,” Williams says.

Serena Williams slides around the red clay of the Tennis Club Parioli in Rome a few days ahead of the Italian Open, practicing to an eclectic mix of musical genres whose only commonality is that they’re sung by powerful women, from Rihanna to Adele to Pink. As word spreads around the club that the world’s most famous tennis player is hitting balls in their midst, a crowd predictably gathers, the youngest among them squealing “Serena!”, the oldest snapping and sharing pictures.

Williams is by far the most famous female athlete in the U.S.—and only Tom Brady and Tiger Woods finish a tick ahead among all athletes in terms of awareness. And that fame carries almost no brand downside—her appeal rates above average across all demographics, from Millennials to blue collar to high income, says Henry Schafer, who tracks Q Scores, which measure the likeability of a celebrity.

After 20 years in the spotlight, Williams knows how to handle the star power. At the end of the two-hour session, she gracefully obliges several with autographs and selfies. But more important: She has figured out at Serena Ventures how to harness it.

The past decade has given rise to the celebrity VC investor, spurred by the success of people like the actor Ashton Kutcher and the musician Nas, who both have their own funds. The recent IPOs for Uber and Lyft included scores of musicians and Hollywood A-listers like Gwyneth Paltrow, Jay-Z and Olivia Munn, who got in early and cashed in big. Overall, Ohanian is skeptical of the trend. “The advice I generally give to founders is don’t take money from celebrities,” he says. “The only exception is when they are really going to add value. Because in most cases, they are not really familiar with this world and if you are doing it to feed your ego, it’s a bad idea.”

So Williams tries to put money in deals where her fame and brand and platform grow the pie. As one of the better product endorsers of this century, it’s something she’s honed in ways that most musicians and actors (who turn up their noses at most product deals) have not. She counts nearly 30 million followers across social media—her posts of herself wearing Nike’s swoosh generated more than $2 million in promotional value for the brand over the past 12 months, according to Hookit, which tracks celebrity influence on social media. “Serena is a once-in-a-generation voice, reaching a global audience that extends well beyond tennis,” says Hookit CEO Scott Tilton.

And that voice is amplified exponentially when dealing with an early-stage brand, rather than one like Nike. She shared a pair of videos in an Instagram story of her entourage eating Daily Harvest meals ahead of her hosting duties for the Met Gala. She collaborated with Neighborhood Goods, which brings a pop-up approach to retailing, for her clothing line. “Using her platform to talk about our mission was the biggest support we’ve had besides her capital,” says Georgina Gooley, cofounder of Billie, which makes razors priced to eliminate the “pink tax” that makes female-targeted products cost more than similar versions for men.

The dating and networking app Bumble added Williams as an endorser for 2019, including a Super Bowl ad. The pair also partnered in a pitch competition in which two winners with female founders were chosen for funding from Serena and Bumble. Three executives of companies in the Serena Ventures portfolio—Daily Harvest, the woman-centric co-working space The Wing, and Lola, a natural tampon brand —networked at the first-ever Bumble Fund Summit in April. “She is facilitating a place for people to connect with one another,” says Jordana Kier, Lola’s founder.

That kind of investor-as-rainmaker power translates into another benefit: deal flow. For more mature deals, traditional venture firms need to take large ownership stakes to hit return targets. Williams, though, is happy to ride along. “Firms know Serena is a hugely valuable strategic investor,” says Ohanian. “I think it is the best of all opportunities, and she can essentially cherry-pick from the top VC firms on deals that are interesting that come her way and at the same time she still has her own deal flow from folks who want her to invest.”

nother benefit of early-stage investing: Even with 34 checks written, she has still sunk only an estimated $6 million into these companies. As venture investing goes, given her net worth, it’s still low-risk stuff. And the returns so far seem promising; Serena Ventures says they currently value the portfolio at more than $10 million and double the initial investment. Nearly half of the companies have had follow-up rounds of venture investment since Williams invested, and Serena Ventures even seems poised to score its first exit after Unilever announced plans to buy supplement firm Olly Nutrition in April. Five of her investments are up at least fivefold. Top performers include Billie, Daily Harvest, MasterClass and The Wing.

But Serena Williams wouldn’t be one of the all-time great competitors without also needing to invest more in herself. While she’s known as a fashion icon, she has cashed in only via others’ platforms, whether endorsements or partnerships. Now that’s changing. Smoller, her longtime endorsement agent, recalls a recent meeting at Nike. “I was talking, and Serena interrupted me and started asking all these questions about their distribution channels, KPIs and growth strategies,” he says. “I looked around and saw their faces. . . . She’s at a level where she wants to understand the process and methods, which I think a lot of people don’t expect.” In May last year, Serena Ventures launched a self-funded, direct-to-consumer clothing line, S by Serena. She kept waiting for someone to fund a company for her to design clothing, she says, but “I was thinking of this the wrong way. I had to invest in myself.”

The line includes dresses, jackets, tops, denim and more mostly priced under $200. She’s excited about an S by Serena show for New York Fashion Week in September. The line got a boost in October when Williams’ close friend Meghan Markle was spotted wearing the collection’s “Boss” blazer, which quickly sold out on the website. Williams returned the favor when she hosted a baby shower for the Duchess of Sussex in February. Williams plans to launch an S by Serena jewelry line this year and one of beauty products in 2020.

With all this commerce, Williams says she’ll continue to abbreviate her on-the-court schedule, prioritizing the Grand Slam events that burnish her brand. While a dinosaur in the tennis world at 37, she still figures she has two or maybe even three years left. “I am in no rush to get out of this sport,” she says. But in Serena Ventures, she’s laid the foundation to keep playing the game her entire life. “I want to create a brand that has longevity, kind of like my career,” she says. “It’s not fancy, it’s not here, it’s not out, it’s not trendy, it’s a staple, like my tennis game.”

Follow me on Twitter or Facebook. Read all of my Forbes stories here.

I am a senior editor at Forbes and focus mainly on the business of sports and our annual franchise valuations. I also spend a lot of my time digging into what athletes earn on and off the field of play. I’ve profiled a bunch of athletes that go by one name: LeBron, Shaq, Danica and others. I also head up our biennial B-School rankings and our annual features on the Best Places for Business (metros, states and countries).

Source: Inside Serena Williams’ Plan To Ace Venture Investing

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9 Things Successful Women Never Do

Often I was the only female FBI agent on my squad. I learned how to be successful amidst a variety of situations and circumstances. Most importantly, I learned what not to do if I wanted to compete in a male dominated environment.

I learned that my success was inexorably linked to the choices I made regarding attitude and subsequent actions. More often than not, it was the choice I made to kick myself into high gear rather than relying on someone else to do the kicking.

While every woman has her own definition of success, here are 9 things that successful women never do:

1. Successful Women Never Ignore Their Fears

If you want to move up, and ahead, you need to confront your fears head-on. Never waste valuable energy trying to avoid them; instead, use mental toughness to manage your thoughts, emotions, and behavior in ways that will set you up for success in business and life.

Suppressing a negative feeling only gives it more power, fueling our fears and slowing us down. In fact, trying to control what we fear will increase the likelihood it will happen.

2. Successful Women Never Run From Conflict

As a female FBI agent, I got burned by conflict, criticism, and unfairness—just like everyone else. The difference is that I did not cower into accommodating others to avoid enduring those negative feelings again.

People who shy away from conflict assume that conflict always looks aggressive, overbearing, and disrespectful. This is not true because conflict can camouflage itself in many forms. We need to be alert for any behavior from others that is attempting to manipulate our emotions or thoughts. Once we recognize conflict for what it is, we make a choice on how we respond to it, rather than react out of fear or ignorance.

3. Successful Women Never Listen To Their Inner Critic

I needed to nip that inner critic in the bud and eliminate inner voices of doubt and anxiety. I did this by choosing to focus my attention on positive feedback and constructive criticism—limited as it might be at times.

Mental toughness is being able to control how your mind thinks, rather than letting your mind control you. The key is learning how to manage your emotions with self-talk and using the right (and positive) words when controlling your thoughts.

4. Successful Women Never Expect Perfect Circumstances

Forget about finding the perfect job or waiting for perfect conditions before making a leap. Learn to differentiate between the pain of growing and the pain of suffering.

It’s easy to say that conditions are poor, nothing is going your way, and that you’ve been dealt an unfair hand. These are all excuses as you move further down the road of surrender.

Use what is at your disposal to keep moving forward in life—take a tip from MacGyver and learn to make the best of your situation. Mental toughness is approaching your circumstances with the right perspective and not expecting a break.

5. Successful Women Never Look At Their Past As A Mistake

I made a lot of mistakes as a new agent. At times it was embarrassing, but I vowed to learn from each one of them.

Some mistakes from our past can be painful or bad, but instead of wallowing in misery, look at them as opportunities to learn something that you didn’t know before it happened. Walk beside friends and colleagues who have made mistakes—you can learn from them, too.

The past does not define us, it simply prepares us for our journey toward success and wisdom.

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6. Successful Women Never Miss Opportunities To Shine

I knew that many times the best way to be successful was to do what others were unwilling to do.

Identify those things that others hesitate to take on. It can be small and simple—it doesn’t matter. Whatever it is, do it well and you will instantly differentiate yourself from the pack.

Then keep going because you never know where it will lead; often, we don’t know what opportunity looks like until we’re closer to it.

7. Successful Women Never Fail To Keep Their Cool

No matter my situation, I knew I was in total control of my life.

One of my favorite quotes is from St. Ignatius of Loyola: “Pray as if God will take care of all; act as if all is up to you.”

Many people make excuses for themselves by saying luck determines whether they are successful or not. Mentally strong leaders are in control of their own luck because they see success or failure as something over which they are in control. Luck may have had some role in their present circumstances, but they don’t waste mental energy by worrying about what might happen.

Control your own luck by seizing opportunities to improve your life and situation. The result will either be a lucky break or the regret of a road not taken.

8. Successful Women Never Fail To Do Their Research

When I interviewed a suspect, I made sure I knew what I was talking about.

When you are meeting with potential investors, clients or customers, make sure you know what you are talking about—know where the landmines are before you open your mouth.

Do your homework; be polished, poised, and prepared.

9. Successful Women Never Say Quit

No matter how hard the investigation or how difficult the assignment, “quit” was the only four letter word I never heard in my 24 years in the FBI.

When you say “quit” or “can’t,” you are sacrificing ownership and control over your attitude and behavior. It shows you have created your own boundaries. When you say quit, you are sending a message about your fear of failure and a lack of grit in testing your limits.

LaRae Quy was an FBI undercover and counterintelligence agent for 24 years. LaRae is the author of “Secrets Of A Strong Mind” and “Mental Toughness for Women Leaders: 52 Tips To Recognize and Utilize Your Greatest Strengths.” See her site and follow her on Twitter TWTR +0% @LaRaeQuy.

I’m Nancy F. Clark the curator of Forbes WomensMedia, author of The Positive Journal, and CEO of PositivityDaily. After studying physics at Berkeley I started out in roc…

Source: 9 Things Successful Women Never Do

How Two Millennial Women Made Over $130,000 While Traveling the World Full-Time

 

Last year, I left my corporate life in New York City behind in a vow to give myself one year to design my dream job. Shortly thereafter, I took off on a 9-month-long social experiment, in which I would circumnavigate the globe by couch-surfing exclusively through my social network. Seventeen countries, four continents, and over a hundred encounters later, I have learned that I am not alone in my quest to earn a living while traveling the world: there are so many people out there right now who are making it work.

Source: How Two Millennial Women Made Over $130,000 While Traveling the World Full-Time

Women in Communication Earn Less, Experience Negative Company Cultures & Still Face a Glass Ceiling – Jennifer Lacayo

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FIU’s Lillian Lodge Kopenhaver Center released the results of a national survey that found that women are more likely to be in middle management or junior level positions in the communication industries, while men dominate top management positions.

In addition, the survey found that the culture of the company most often prevents women from being promoted and keeps them from advancing in their careers and that women are more likely to spend fewer years in the communications professions than men, lacking longevity in their current positions.

“This survey has given us critical results to help us understand the current role and status of women working in those industries,” said Lillian Lodge Kopenhaver, executive director of the Kopenhaver Center for the Advancement of Women in Communication. “Interestingly, workplace culture came to the forefront as inhibiting advancement for women, a factor that companies need to have more awareness of in order to provide equity for all employees.”

Women dominate lower salary level positions in all communications professions. However, those working in public relations, advertising and market communications do slightly better than those in the journalism. Women also said they had been passed over for advancement into a management position because of a “men only” culture in their companies.

The survey, which was distributed to 22 national professional organizations across the U.S., used nearly 900 responses to come up with its findings.

The first survey was conducted by the Kopenhaver Center in 2016, and comparisons to 2018 responses show little progress in all areas except salaries, where there were some advancements.

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