Best Books (aka What's on My Nightstand): Alpha Girls by Julian Guthrie

I've had nearly fifty meetings with investors over the past few months and most of them were men. So when I was invited to attend an event where I'd get to meet four of the most prominent female VCs in Silicon Valley I was all over it. The event was a book party for the newly released Alpha Girls: The Women Upstarts Who Took On Silicon Valley's Male Culture and Made the Deals of a Lifetime.

I started reading the book in the cab on my way home and devoured it in two days. The author, Julian Guthrie, is an award-winning journalist who spent twenty years at the San Francisco Chronicle and has the prose to show for it. Through mechanical research and vivid storytelling, Guthrie charts the course of four pioneers: Magdalena Yesil, Mary Jane Elmore, Theresia Gouw, and Sonja Hoel. These women helped define the high-stakes world of venture capital and made many tiny startups household names including Salesforce, Facebook, and Google. Reading about these women's influence, I hovered between shocked and infuriated that I had never heard their stories before. Whether it was workplace discrimination or personal tragedy, these women emerged from each fire more resilient and determined than they had been before. Alpha Girls is a must read for anyone who is pushing through any kind of adversity and needs to know without a shadow of a doubt: I can do this.

A Peek Inside My Village: Rachel Cargle

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The most rewarding part of investing in superstars is seeing them soar. Every time I see another media mention of Rachel Cargle or read one of her articles I pinch myself. Two months ago she and I were on the same stage being honored by Girls Leadership for using our voice to advance women and girls and I couldn't have been more proud.

Rachel Cargle is an activist, writer, and lecturer. Through her academic work she explores the intersection of race and womanhood, offering the tools and facilitating the frank conversation that is desperately needed in our polarizing discourse. She leads anti-racism intensive workshops and provides much needed inspiration to her 250k + social media following. Rachel has also captured the attention of other incredible writers and thought leaders. Glennon Doyle, Brene Brown, and Cheryl Strayed all support her work. It's no wonder, because Rachel is wise beyond her years.

When I asked her what she's had to drop the ball on in order to create impact in the world she shared a recent life lesson that was related to the two of us. She reminded me that many moons ago she worked for me and that I had transitioned her out of the role because it wasn't a good fit. I had practically forgotten about that and have since hired Rachel for other roles. She admitted that she had felt terrible that she hadn't delivered for me but had learned, "It's possible to disappoint people...it's possible to fail...and everything will be ok. We often identify stumbling blocks as major setbacks, but instead, if we let them, they can be some of our greatest lessons turned launching pads towards exactly what we had been pushing towards all along." I'll say, because recalling that history made me respect and love Rachel Cargle even more.

Tiffany's Epiphanies: How to Get Paid to Speak

As a professional public speaker, I feel lucky I have the chance to inspire people to enhance their personal lives and workplaces. Recently, one woman asked me how she, too, could build her own public speaking practice. I told her this: public speaking is like a kite. If you can get the business in the air, it will fly. Public speaking is its own marketing tool -- when you deliver a high-quality product to a room full of people, the likelihood is high that one or two of them will want you to speak at their organization. Here are some questions to ask yourself if you want to launch a public speaking practice.

Tiffany's Epiphanies: Everyone Fails at Who They Are Supposed to Be

My family and I saw Avengers: Endgame on opening night, and, admittedly, I spent most of the 3-hour saga a little confused. But the one scene that brought me so much clarity was when Thor travels back in time to see his mother and she shares this epiphany: Everyone fails at who they're supposed to be; the measure of a hero is how someone succeeds at who they are. This wisdom from Thor's mom sums up the message of my book, Drop the Ball. Watch and learn the similarities.

Tiffany's Epiphanies: What Made You Successful Won't Keep You Successful

I was recently watching the HBO documentary The Defiant Ones about Jimmy Iovine and Dr. Dre. This documentary had a huge impact on me, and, specifically, the scene in which Bruce Springsteen describes why Jimmy has been so successful: "He is willing to shed what made him successful and take on new behaviors--he's not afraid of moving forward." This one line made me look inward to think about which behaviors are holding me back. Watch and learn what I came to realize.

Tiffany's Epiphanies: How to Drop the Ball at Work

In my book Drop the Ball, I discuss tactics on releasing expectations to focus on what's most important to you. At home, this can be an easier exercise because we feel like we have a lot more of control over what happens. At work, when dealing with other people's priorities and expectations, it can be more challenging. Here's my advice: Always lead with the forest and then lead with the trees. This means dropping the ball at work is less about relinquishing responsibility and more about deciding on your highest and best use and how you can delegate to propel other people on your team. Watch and find out how you can drop the ball at work and strengthen—not damage—your brand.

Tiffany's Epiphanies: The More You Ask for Help, The Less You'll Need to Ask for It

Supporting you in your journey is a gift that many people would love to give. Think about how good it makes you feel to help someone else. Mustering up the courage to be vulnerable and let others know what you need isn't easy. It's like a muscle that needs to be flexed. But once you do, they're able to become more cognizant and the less you'll need to ask for help.

Tiffany's Epiphanies: If You Don't Let Losing Stop You, It Will Propel You Forward

Many women don't put their hat in the ring or reach for lofty goals until they are overqualified. After experiencing highs and lows while launching The Cru, I've realized that when you do face failure or don't get what you want, you're forced into asking yourself some poignant questions: Why did I want this to begin with? Whose help do I need to get there? What do I need to reach my goals? If you don't let losing stop you, losing will propel you forward.

Tiffany's Epiphanies: Want to Find a Soul Mate? Know Thyself

"Why did you marry your husband?" my therapist asked me. I paused and responded that Kojo gave me the freedom to discover who I was going to be without feeling pressure to be the wife he wanted me to be. I realized this: The secret to finding a partner is self-awareness, and understanding what you need from a partner for you to thrive. Watch and learn how to discover what makes you tick.

Tiffany's Epiphanies: Changing a Story Requires Changing Assumptions

We often get blocked by the assumptions we make: my company is too big to innovate; women don't support one another; men can't handle running a household. Next time you're trying to solve a tough problem ask yourself, what are the the stories I might be telling myself that could be supporting this gridlock? That is the first step to move past it.