I am absolutely delighted to have gathered with Kate, Kelly, and Erin. These incredible women aren’t just brilliant business minds, they’re my longtime mastermind sisters, accountability partners, and the kind of friends who’ve seen me through both boardroom wins and breakdowns (often with margaritas in hand). Over the past eight years, we’ve built something rare: a bold, enduring mastermind that’s equal parts strategy lab, therapy session, and lifeline. If you’ve ever wondered what it takes to create a peer group that lasts, through recessions, personal crises, and even questionable Cancun dining choices, you’re about to get the unfiltered, often hilarious playbook. Trust me, their stories will make you want to text your own ride-or-dies by the end.
What Was It Like to Start a Mastermind in 2017?
[Kate] It all began at a conference, because doesn’t every great business story start with wine and late-night brainstorming? We were exhausted from the usual surface-level networking and asked: What if we created something deeper? Not just a mastermind, but a long-term sisterhood where we could talk about business, faith, and life without filters.
The crazy part? We had no plan. Just a gut feeling that we needed this. We started with seven women, met in Cancun for our first retreat (spring break chaos included), and over time, it distilled down to the four of us. Some left because of life changes, others because the fit wasn’t right, and that was okay. The magic wasn’t in perfection; it was in persistence.
[Natalie] I was the newbie in the group, still figuring out my business. When Kate invited me, I almost said no because I thought, “I’m not at their level yet.” But that’s the thing, a real mastermind isn’t about hierarchy. It’s about growth. That realization has stayed with me throughout this entire 8-year journey.
Key Shifts That Shaped Our Mastermind Over 8 Years
1. From Big Group to Tight-Knit Four
We started with seven, but as businesses and lives evolved, some naturally stepped away. Instead of forcing it, we leaned into the deeper connections that remained.
Erin: “Losing members wasn’t a failure; it was refinement. The four of us? We’re ride-or-die.”
2. From “All Business” to Whole-Life Support
Early on, we stuck to spreadsheets and funnels. Now? We talk about marriages, parenting, faith crises, and mental health just as much as revenue.
Kelly: “The turning point was Marco Island 2021. We spent a whole day crying over family struggles, and left stronger than any ‘strategy session’ could’ve made us.”
3. From Splurging to Strategic Spending
In 2020, we stayed at LeBlanc Cancun (hello, 5-star luxury). In 2024? We booked a Vegas Airbnb. The priority wasn’t the resort, it was being together.
Kate: “We’ve learned to adapt. Fancy or frugal, the value is in the conversations, not the caviar.”
The Strategies That Made This Mastermind Last
1. No Competition, Only Collaboration
We’re all in different niches (agencies, courses, operations), so there’s zero fear of idea theft.
Natalie: “I’ve been in masterminds where people held back. Here? We overshare because trust is the foundation.”
2. The “Hot Seat” Rule
Every retreat, each of us gets a full day to vent, brainstorm, or ugly-cry without interruption.
Erin: “It’s not advice-giving unless asked. Sometimes, we just need to be heard.”
3. Location Matters (But Not How You Think)
We’ve met in:
- Cancun (twice, including the infamous “Kelly vs. Rude Diner” incident)
- Cabo (whale watching > Zoom calls)
- Marco Island (that MTV Cribs mansion we didn’t need but loved)
- Palm Springs (where we whiteboarded life plans on a sliding glass door)
Kelly: “The pool is non-negotiable. Margaritas + margins = magic.”
4. Conflict = Growth
We’ve had blowups. But we apologize fast.
Kate: “One fight almost ended us. Then we realized: If we can’t be real here, where can we?”
Moments like that shaped our mastermind (over the past 8 years) into something far deeper than strategy or networking. They shaped us.
Our Best Advice for Starting Your Own Mastermind
1. Start Small, Stay Flexible
- No need for 10 people. 3-5 committed > 20 flaky.
- Ditch rigid rules. Life happens, adapt.
2. Seek Differences, Not Clones
- Faith, politics, business models, we disagree on plenty. That’s the point.
- Natalie: “If everyone nods along, you’re in an echo chamber, not a mastermind.”
3. Prioritize Receiving, Not Just Giving
Most masterminds fail because everyone’s in “teacher mode.”
Erin: “I used to only give advice. Now? I say, ‘I’m struggling with this, help.’“
4. Make It Sticky (Beyond Business)
- Rituals (pool time, one fancy dinner per trip)
- Vulnerability (we’ve seen each other cry more than our therapists have)
These are the rhythms that have made our mastermind something we fiercely protect. It’s not about convenience, it’s about commitment.
What Worked in 2017 That Would Flop Now
- Forcing yearly dues. Life changes, we stopped penalizing exits.
- Ignoring personal crises. Now, “How’s your marriage?” is as important as “What’s your revenue?”
- All work, no play. No retreat is complete without an excursion (whales > workflows).
Final Takeaways: Why This Mastermind Still Thrives
- Depth > size. Four trusted voices beat a crowded Zoom room.
- Conflict refines us. Fight, forgive, and keep the group text alive.
- Invest in the “unsexy” stuff. Contracts matter, but so does asking, “How’s your soul?”
Kate: “Eight years in, we’re not just a mastermind, we’re family. The kind that will fly to Mexico to celebrate your win… or bring tequila to your breakdown.”
This kind of long-term, heart-centered connection doesn’t happen by accident. It happens when you commit to showing up. That’s what has kept our mastermind alive and thriving, through it all.
“This group isn’t just a mastermind. It’s my board, my safe space, and the place where I can show up fully, even when things feel messy” — Natalie Gingrich
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