Why It’s Time To Start Your Own Mastermind Group

How a well-curated group of women has empowered each other to shoot big (and win).

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About a year ago, a received an email from a woman I had recently met over the phone. Her name was Jaime Bott, and she was a talent partner at a top venture capital firm, Sequoia Capital. We had been introduced through one of the partners there after I had let him know I was planning on moving on from the company where I had spent the last 11 years. She and her friend Kelly Graziadei were putting together a group of women to meet over dinner, and wanted to know if I’d like to join. I was flattered she would consider including me, given we had never even met in person. In fact, we had only had a 20 minute conversation but we clearly connected.

I read the details of the dinner and realized it was on the day we were moving into our new home. Not exactly convenient. And it was in the South Bay, about an hour’s drive from my home in San Francisco. She had also included a list of the invitees — it was an impressive group that included CEOs, founders, and executives from top companies like Facebook and Google. And they were all women! I had been searching for a group like this for years and now it had just fallen into my lap. There was no way I could miss out on meeting them. I let my husband know about the invitation, and of course, being my biggest supporter, he encouraged me to attend the dinner and he would cover the move that evening.

I was in an interesting place at the time; a turning point many people find themselves in at various points of their lives. I had just left a company where I had spent over a decade, with a team that I thought of as family. It was a difficult decision, but I was ready to do something new, to grow. I chose to take some time off to spend with my kids before deciding what was next. I was feeling a lot of emotions over my situation: excitement, fear, grief, joy, and peace, among others. I knew I had made the right decision, but not knowing what was next was giving me a decent amount of anxiety. I needed support, and this invitation could not have come at a more perfect time in my life. Hopefully this group would be able to provide what I was looking for, I thought to myself as I drove up to Jaime’s home.

After introductions, we settled down to dinner. It was a beautiful, warm summer night and we dined outside, a nice relief from the chilly San Francisco fog. We shared where we were in our careers, what our goals were, and what we feared. We opened up to each other quickly, despite having known each other for a short period of time. We offered each other introductions, advice, perspective and support for tough decisions. The women congratulated me on my decision to make a change, and we discussed how important change was to continue growing.

We eventually moved to the fire pit and sat around the fire covered in warm blankets while we finished our discussion. Before we knew it, it was past 11:00. Only a few hours into our introductory dinner, it already felt like we were old friends. We agreed we would like to continue meeting, and said our goodbyes. Three months later we met again, and dined over vegan fare at an animal sanctuary owned and run by one of the women. In addition to being a successful group of women, they were also very interesting and great at manifesting their visions. By the second dinner, many of the women had chosen to leave their jobs and pursue something new. We discussed what each person was looking for, offered (and made) more introductions, and talked about startups we love. We discussed the progress we had made toward our previous goals, and encouraged each other to pursue new ones.

After each dinner (we have had four so far), I left feeling empowered to do things I had thought about, but had been afraid to pursue in the past. It was clear the others did as well. Over the course of the past year, many have left the companies they had been at for years — they became venture capitalists and left their more established companies to join startups or to start their own ventures. One became the Head of Product at Thrive Global. Another started an organization called Him for Her, aimed at getting more women on boards. One of the women shared with us that she felt empowered to ask for a huge raise — and got it.

I started a new job as a Head of People at a startup, a change from by previous role as a sales leader. I felt comfortable taking the role thanks in part to the support and encouragement of the women. I started a women’s investing group and even invested in one of the startups (Year & Day) I learned about at one of the dinners. We sent out articles about each other to the group and applauded our successes (something that can sometimes be difficult to do with friends who may be on very different career paths). Our discussions helped us see the latent abilities that we might have known were there, but were hesitant to recognize.

I have thought a lot about why this group has had such an impact, and I realized so much of it comes down to intention. We meet specifically with the goal of discussing our goals and successes, so it’s never awkward when we talk about them, which it sometimes can be with friends or co-workers. There’s no competition; we are there to celebrate each other and bragging is encouraged (and doesn’t have to be humble). We are truly happy for one another and there’s never any envy or dismissiveness. There’s a sense that any time one of us experiences success, that feeling is shared among the group.

I recognize how fortunate I am to have had this group appear in my inbox, and I realize many people may not have access to people like the ones I’ve described. But the caliber of the women, while incredible, is not the most important part of the group; it’s the mindset. Knowing we can talk openly about our goals and are there to encourage each other to make bold moves and take big risks is what makes this group so powerful. And whether the people you surround yourself with are early in their careers or further along, they can offer the same level of support if they go in with the right mentality — in our case, it was the idea that women need to support and encourage each other, and when one of us wins, we all win.

Originally published at

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