Tiffany's Epiphanies: Not Everyone Is Worth Convincing

There are many times in our lives when we're trying to cultivate a relationship with someone in order to secure their investment. If their request or their questions aren't sitting right with you, move on. Recently, I was meeting with a male VC while fundraising for my new company The Cru, a peer mentorship platform. He said, "Maybe it's because I'm a man, but I don't really understand why someone would want this. Convince me." I politely declined. Here's why.

Tiffany's Epiphanies: You Can't Live a Brave Life Without Disappointing Some People

Whenever I am feeling overwhelmed, I search for Oprah's inspirational videos on YouTube. Recently, I found myself in a situation where I needed to be in two very important places at the same time—in New York and Boston. It was devastating because I hate disappointing people that I care about. Then I heard this epiphany from Oprah: "You can't live a brave life without disappointing some people." Watch and learn how I put this into practice.

Tiffany's Epiphanies: It's Okay to Change Your Goals

Here's a confession: Earlier this year I was really struggling with tackling an item on my monthly to-do list, so I just didn't do it. I kept putting it off and ignoring it, until an email from a colleague made me stop and take a closer look at the to-do. Her email included three very important questions that challenged me to decide if this was something I needed to keep doing. Could I take this off my goal list? Watch and learn to find out the questions and how I realized it's okay to change your goals.

Tiffany's Epiphanies: Measure Your Time Before You Spend It

If I had a dollar for every woman I sat down with who had an overflowing list of things to do I would be a wealthy woman. One of the tricks I use to figure out what I can potentially drop the ball on is to compare the amount of time it would take me to complete a task with my hourly value rate. So that bow tie that I should return to Amazon? It's going to Goodwill instead. Watch and learn how to calculate your rate and figure out what you can drop the ball on.

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


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'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.