Put on my best p-p-p-poker face

Last Friday, I hosted 50 incredible women — entrepreneurs, investors, artists, creators, creatives, a chess champion, an online educator, a nuclear energy entrepreneur, and women who have built and sold businesses for north of $200 million — for a night of poker.

The theme? Dress like your vision of a queen. Cleopatra, Miss Philippines, Frida Kahlo, Marie Antoinette, and Gloria Steinem showed up, along with a few awesome founders whose companies I’ve invested in, including Megan from Plot, Lindsey from FYPM, and Farah and Misbah from my most recent investment, Nectar AI.

I haven’t talked about it much, but I’ve been hosting poker games every week in my home for the last several months.

Why poker you may ask? I’ve always loved a dose of healthy competition, but with poker, there is truly an art to playing the game. Strategy and risk-taking. Equity and odds. Reading personalities. Knowing when to go all in, and knowing when to cut my losses (more often than not).

I’m learning a level of discipline that is completely new. I study, I use apps that test my skills, and I get to use my brain — while also, for the first time, having a hobby. Poker has reintroduced me to, and is honing, my toolbox of skills as both a player and an entrepreneur.

Strangely, there are a lot of parallels to the nature of poker and it’s strategies — here’s what I’ve noticed: ?

1. The importance of patience. At every turn, there are choices in life. Be patient, wait for the right hand to play, observe your opponents, and bide your time for the perfect moment to strike — because rushed decisions can lead to costly mistakes. Don’t just play a hand because you can. I’m telling you this as the most impulsive person ever.?
2. Always weigh your risks. Whether it’s at the poker table or in an investor meeting, risk management is paramount. It's essential to calculate potential losses and gains, minimize risks, and always have a backup plan.
3. Read the room. In poker, you observe your opponent's body language, betting patterns, and reactions. In business, particularly in potential partnerships, learning to read people and understand their motivations gives you a significant advantage and helps you make more informed decisions. It’s not creepy or manipulative, it’s smart — and remember that they’re doing it right back at you, whether you know it or not.?
4. Adaptability is key. Just because one strategy worked in one hand does not mean it will be effective in the next. When you’re building a business, you need to constantly pivot — so get comfortable with change and be flexible about how you get there. Staying rigid can lead to failure.
5. Silence is a strategy. In poker, bluffing is a strategy used to mislead, but too much bluffing can lead to a loss of credibility. I always say that transparency is the best policy in a business, but knowing when to keep your cards close is a valuable skill in poker, and often kind in life and business.?

Poker has introduced me to a diverse network of people and given me a new way to get to know them. I’ve raised a lot of money for Trust Fund at the table — probably north of $500K. Opportunities beyond winning the next pot are waiting for you — sometimes much bigger than what you’d think is possible.

Part of my job as a venture investor is to connect with the next generation of founders, funders, and all-around interesting people. Who I meet and what I see informs what I invest in, and the people I surround myself with become cultural fortune tellers for me and for the fund.

Back to Friday.

Three poker tables, 30 swiveling chairs, pro dealers, thousands of chips, and one table with real money (who doesn’t love the cha-ching sound of Venmos being paid out?).

By the end of the night, these incredible women had picked up the game and left obsessed, ready to keep learning. And the ones that learned the most? No surprise — they asked the most questions.

Poker isn’t my platform, but it’s powerful, and fun. There never seems to be enough women at the big boys’ table — so consider this a selfish effort to recruit more queens to make money and grow the pot, together.

A special thank you to our generous sponsor, Juliet, for the amazing wine selection — it’s the prettiest packaging I’ve ever seen. Lauren De Niro Pipher, you’re a shark in the making.

And Casinola, I appreciate the full poker setup! You turned my house into a legitimate casino.

Thank you also to Ghia, 21Seeds, Sake High!, Rosaluna, and of course, Liquid Death for keeping our glasses filled all night long!

— Sophia