We’re excited to introduce you to the always interesting and insightful Krista Boling. We hope you’ll enjoy our conversation with Krista below.
Krista, thanks for joining us, excited to have you contributing your stories and insights. Risking taking is a huge part of most people’s story but too often society overlooks those risks and only focuses on where you are today. Can you talk to us about a risk you’ve taken – it could be a big risk or a small one – but walk us through the backstory.
One of the biggest risks I’ve ever taken was launching my first barbershop. I was in my early twenties, going through a divorce, raising a young daughter, and working at a shop where I felt undervalued. I knew I wanted more — not just for myself, but for the people around me. I envisioned a space where my friends and I could thrive in our craft, a laid-back, supportive environment that celebrated what we were doing in the industry.
I started planning, pitching, and searching for investors. I got turned down by multiple banks — they saw my age and lack of experience as liabilities. But I saw it as fuel. Eventually, I found an investor who believed in my vision, and I went all in. No safety net, just belief, grit, and a whole lot of hustle.
Seven years later, I own two barbershops and just opened a bar this year. That risk — stepping out of survival mode and into entrepreneurship — changed everything. It taught me that betting on yourself isn’t reckless when it’s backed by purpose.
Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.
I got into the barbering industry because traditional school just wasn’t my path. I’ve always been more artistic — drawn to creativity, connection, and helping people look and feel their best. Trade school gave me a way to channel that energy into something tangible, and barbering quickly became more than a skill — it became a calling.
The Cave was born from a vision to create something different: a grooming experience designed specifically for a masculine clientele. Not just a place to get a haircut, but a space to unwind, recharge, and feel taken care of. We offer everything from cuts and beard trims to facials, scalp massages, and straight razor shaves — all with a cold beer or a complimentary beverage in hand. It’s about the vibe as much as the service.
But what I’m most proud of isn’t just the services or the aesthetic — it’s the people. Every barber who’s ever worked at The Cave has helped shape the brand into what it is today. They’ve brought their own style, energy, and work ethic, and together we’ve built something that feels like family. They make my job easy, and they make The Cave what it is: a place where people feel seen, respected, and sharp.
Do you have any stories of times when you almost missed payroll or any other near death experiences for your business?
One of the closest calls I’ve had in business was during the early days of COVID. I had just opened my first barbershop — full of excitement, momentum, and dreams — when the shutdowns hit. Suddenly, everything stopped. Bills didn’t. Clients couldn’t come in. And the industry I’d poured my heart into was put on pause.
Navigating that time was brutal. We had to adapt to mask mandates, shifting health guidelines, and the political tension around vaccines and safety protocols. Every decision felt loaded — not just financially, but emotionally. I was trying to protect my team, serve my clients, and keep the business alive, all while the world felt upside down.
There were moments I wasn’t sure we’d make it. But we did. We leaned into community, stayed flexible, and kept showing up. That experience tested everything — my grit, my leadership, my ability to pivot — and it made us stronger. Today, we’re thriving, and I carry that lesson with me: resilience isn’t built in comfort, it’s forged in crisis.
Do you have any insights you can share related to maintaining high team morale?
My biggest advice for managing a team and keeping morale high is simple: don’t take everything too seriously. Life is hard, and the unexpected always shows up — in business and in people’s personal lives. Giving your team grace and room to mess up builds relationships that are stronger and more honest.
I don’t see my team as working for me — they work with me. That mindset shifts everything. It creates a culture of respect, collaboration, and shared ownership. When people feel safe, supported, and trusted, they show up with their best. And when they don’t, they know they’re not going to be punished — they’re going to be understood.
Contact Info:
- Website: https://cavemannwa.com
- Instagram: @thecavenwa
- Facebook: thecavenwa
Image Credits
blue box studios