The New ‘Ask Sarah’ Podcast

Many of you know that we just launched a second podcast last Fall — the Ask Sarah Podcast — a show where I go deep into your life, my life, and everything in between. This podcast isn’t just about my life, although you are welcome to ask me anything you’d like. This show is a place where you can ask me for my feedback, my opinion, and my strategy on whatever challenge or puzzle you’re currently facing.

We’re sharing one of our latest Ask Sarah Episodes here as a preview on The Startup Pregnant Podcast so you can listen in. In today’s episode, we talk all about the ways I think about building mastermind programs, facilitating community, and bringing people together. Yes, I’ve overthought all of it—to the tiniest degree.

In this episode, we have a really fun question I am excited to geek out about. We are going to dig into the Wise Women’s Council and the year-long membership that I created, how I designed it, why I designed it the way that I did, and how I thought about the membership model.

This specific question that I got is: “How did you decide on the model for your membership and have you been in other programs like this structured in the same way?” I’m excited to talk about this because I like to overthink things like this. I get really geeky about community design and creating really good containers for people and then testing them. I have been hosting mastermind programs for last five or six years, and one of the things that I like to do is to figure out and really test and tweak each year to make it better and better. Today, we’ll talk about the pieces that make it work, the components that make a mastermind or community program great, and how to setup the right infrastructure.

I have been in things that have worked amazingly well and I have been in things that have fallen flat on their face. Each time, I observe and I take notes and I think about it and I say, “Okay. What worked really well there and what didn’t work really well and how can we combine these elements to create the next container?”

I hope you enjoy my iterative approach and hearing about all of the lessons I’ve learned so far in building mastermind programs. Take this, build your own, join one, or find a community space (or three!) to call home.

  • How to create the right container and space for people to feel comfortable coming together.
  • How big your mastermind or group should be, and why the size matters.
  • What the digital world is like, and how to create intimacy in a digital setting.
  • What the frequency of meetings has to do with bringing a group together, and why weekly is often way more challenging than we expect.
  • My love of asynchronous communication, and why it’s so useful for busy working parents, in particular.
  • The magic of being seen by other people and why a distributed (non-local) community can be so great.

The Startup Pregnant Podcast Episode #140

  • Scheduling is one of the greatest challenges for working parents. There are so many moving parts to my day and so many chances for everything to just blow up in my face that having more things to add to my calendar is a hard no. That’s why I made the majority of our mastermind asynchronous—you can still get the community and the connection, but without all the madness of calendaring.
  • There are so many programs and courses out there that are insanely ambitious. It’s like “your five-day plan to this,” but my experience of taking so many courses and programs is that they’re all way too fast. I can’t do it in five days. Most courses make me feel stupid and insufficient. I need it to be one lesson a month, and then I still need time to catch-up. It needs to fit into my existing schedule without being overwhelming.
  • Sometimes I sit on a question and try to listen to what comes up in my life as an answer. I’ll sometimes sit with a question for several months before I really find the thing that’s calling to me—that’s part of the space I try to create in my community mastermind. Space to sit with open and unanswered questions and just BE with them around other people for several months, until finally something moves or shifts. There’s so much pressure to Get The Right Answer In One Hour. I don’t think life really works like that.
  • I think that most advice is really bad, because we don’t actually listen to each other. We jump straight to offering solutions, but we never took the time to really sit with, and listen to, what’s actually in front of us.
  • Most people are really wise and intelligent, and they need space to process and examine more than anything else. They don’t need answers shoved in their face. They need patience and curiosity and compassion.
  • Weekly meetings sound nice but I don’t think they actually work well. I’m a way bigger fan of biweekly.


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Want to be part of the magic that is gathering together with smart, talented, wise business women? The 2020 Wise Women’s Council is now open for enrollment. Apply by February 20th to be considered for our year-long program. We kick off in March. Yes, we want you—all of you in your messy, imperfect, parenting-business-what-am-I-doing-madness. Apply here.


If you’re a fan of this podcast, you’ll love the private, ask-me-anything fireside chat with Sarah. For Patreon supporters only, get access to a new podcast episode every month AND the chance to ask Sarah any question you want about life, business, and parenting. She will honor everything honestly. Patreon supporters who become sponsors at $7 a month get exclusive access to these episodes that aren’t published anywhere else. Head to to become a back and get immediate access to the episodes.

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