We caught up with the brilliant and insightful Laura Night a few weeks ago and have shared our conversation below.

Laura, looking forward to hearing all of your stories today. Can you talk to us about a risk you’ve taken – walk us through the story?

Opening any and every business is a risk. It’s scary and exciting and kind of every emotion and experience wrapped up into this idea that we want to birth. The journey becomes almost obsessive in some ways. When this spark is lit, and I’ve found that often we may not know exactly when or how, we’ve grown more uncomfortable with where we are, no matter how stable, and we just have to begin. It’s a passion, a drive, a twinkling idea that we just can’t really ignore any longer. In my own journey, and while consulting for others, I’ve seen the magic of this moment so many times first hand. There’s something almost addictive to it. It’s a rush, it’s invigoration, it’s terrifying, and I think we all have to be a little bit delusional when we begin. Sometimes it works and sometimes it doesn’t… There’s almost nothing more risky than being like, okay I’m going to go all in on this idea and lets see if it works. Of course there’s ways to minimize risk but essentially every business owner is going to Vegas and putting everything they have, all of their drive, passion, inspiration, resources, funding, ego on Black hoping it’s going to land where we need it to. It’s crazy! But oh so good… when it works.

Over the course of the last 18 years I’ve birthed 7 businesses, 4 still in existence but merged into 2. Hallowed Home, a metaphysical boutique & co-op now open for 2 years, focused on supporting and highlighting women owned companies, experiences and products. The other business, Vida Maui or Vida by Sip Me Maui, is a coffee shop that used to be comprised of 5 locations in Maui under the name Sip Me that started in 2014. It’s now having a really sweet moment in this new chapter with 1 very curated, supported location. I’ve got some really exciting things developing for it that I’m excited to launch. There’s risk for sure in that too.

I start businesses, or add to them, when I can’t find the experiences I want within markets I feel passionate about, in the area I live in. That’s a powerful thing in business, to fill a niche. In many ways I’ve gotten lucky, my timing was right in 2014 with the launch of Sip Me Coffee, but it all comes down to what a community wants and will support and how willing you are to ride the ride. It’s an enormous commitment and an even larger amount of work. If you can find that special idea, experience or thing, with enough tenacity and willingness to pivot, you are less likely to fail. Or you’ll fail, and fail, and fail but the key is to keep going. Pivot, amend, re-work and don’t be too attached to anything or you’ll get stuck. No matter what though, there’s huge risk.

I’m 42 now, and started my first business at 24. I’m ready for some stability so I’m in the process of exploring how I can better develop what already exists in my current businesses. Previously it was like, how many different businesses can I pop open in different markets and make successful?! Let’s see! Now, I am much more interested in streamlining my resources, energy, availability and build within. In the belief, or hope, that this will feel less risky. I trick myself into thinking this is minimizing risk but often adding into any strong, steady, stable business is a huge risk too. It’s a delicate balance. Previously I had to kind of get wicked good at knowing when and how to downsize which is also filled with risk, removing only what you want, hoping the thing you’re working to preserve remains. The goal for this new chapter is to get equally as good at building and releasing within the stability of one business structure. I used to streamline and then essentially copy and paste in a new brick and mortar… This seems much more challenging, but it’s also exciting. Trying to master something that just can’t be “mastered” on any level.

Both Hallowed Home and Vida are in growth periods right now… I think it’s key to understand if you are going into business for yourself it’s best to get somewhat accepting that there’s always risk. When you begin, there’s risk. As you have to pivot, there’s risk. When you scale up, even on the small ideas, there’s risk. When you downsize, yep, there’s risk. It’s all a risk! Every decision you make (no pressure…) This is also why humor is so important. And not taking yourself too seriously… It’s all in the game. I’ve experienced the building, creating, scaling of my businesses into larger businesses, as well as everything kind of in-between including my best case and absolute worst case scenarios. You’ll win some, you’ll lose some, but no matter what, you’ll likely be okay. The risk though, it never goes away.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

As I mentioned before, everything I got into was because it was something that I wanted as a consumer and couldn’t find in my market or area. Most of it revolved around community and havind spaces that felt like home and brought people together. This was what birthed my original coffee shop concept, Sip Me. I couldn’t find a space that was serving all organic products and had that kind of small town feel. In 2014 I launched and within 2 years grew from 1 location to 4 with a 5th in the works. I have a big passion for community, and community building and this seemed like a natural thing even though I’d never worked a day in service. Ever. It was terrifying! I had no idea what I was doing but I just knew it would work. There was a lot of bouncing around trying to find money, trying to find a space. I moved to Maui in 2001 and couldn’t really find my community. Something I had grown up with in small-town Montana was community and meeting around coffee shops and diners. It was something that stuck because it was what lead the charge on building the company. In the end covid knocked out all but our Flagship location, which I then lost when the landlord decided not to re-new the lease in the space we had been in 10 years. In the end it worked out because I found an investor who had a space just down the street. He had been a client for a long time and wanted what we were doing back. He believed in me and I trusted him and myself enough to begin again. That’s how Vida by Sip Me Maui came to be. The name was birthed from Frida Kahlo “Viva La Vida,” or “long live life.” Life by Sip Me Maui felt right. This new concept and new business carries a lot of the old foundation and core beliefs (community comes first, what we put into our bodies matters, supporting small local organizations and businesses is key) but it’s built on with more inspiration, knowledge, funding, trust in myself and really investing in my team in a way I didn’t really understand how to do before. I am trying to be a different kind of business woman. Previously I really felt that to be successful I had to be “strong,” somewhat un-yielding and really embody the “CEO” energy. This time I’ve really jumped into building together and focusing on how I can help the team members around me really step into themselves, take up space and be inspired to really trust themselves. It’s changed the company in really remarkable, strong ways… I’m really happy. For the first time maybe even in business… And it makes sense that it’s likey because everything we do, is really built authentically on where we are as a team, where I am, not what I think I need to be or embody so I don’t expect that of others. Not only is hustle culture dead, inauthenticity and ego is too. At least at Vida.

My other business Hallowed Home is really birthed from my connection to myself and my community and providing tools, support, and connection on an even deeper level. Vida, as a coffee shop, has an amazing, large community network. I wanted to reach people on a deeper level though. Hallowed Home was my way to do that. To create a sacred space for people that felt connected to it, to me, to whatever pull is within them to connect. That means a lot of different things to each person. I like to create, offer and then hold safe space for others. It’s what I am best at. Hallowed Home is the physical representation of that. We have everything from spiritual tools, and ways to connect, to book clubs, women’s circles, Night Markets supporting small business, celebrations and offer open dialog and communication and avenues for anyone looking to dive deeper.

In a lot of ways Hallowed Home is the deeper extension of Vida… Both are building together. I can’t wait to see where they end up and I’m really honored to be caretaking both of these spaces and our community. It’s good medicine, and practice. I owe any successes I’ve had to the whole journey. The “failure,” the stress, the misteps and mistakes, the wins, the losses, everything… It was needed. And I’m even excited to see how my businesses change alongside me as I continue to learn and change and grow. I can’t wait for these next chapters! I spent my 20s, and 30s really worried that I was doing things wrong and wanting to get things “right.” Now in my 40s I’ve really learned that those worries are time consuming and draining. I still made mistakes and missteps and had loss, embarrassment, financial ruin, stress, and all the things I was working my ass off to avoid. Trying to never make a misstep didn’t give me any more safety, respect, financial increase, success, joy, peace, happiness, or balance. What’s going to happen is going to happen. I’d rather be in a state of grounded confidence and assurance that I was fully, authentic, and trusted in all of my decisions and choices when they happen. I think that’s the really exciting part… Knowing I have the things within me to navigate whatever needs to be navigated. It frees up space to really create and find passion and hold space for others. My Vida team just currently happens to all be young women in their very early 20s and 30s… They teach me so much. My greatest joy right now is in creating a space where they can feel free to learn and explore and be inspired in themselves and seeing how that shapes the company and feeds each client coming in. It’s growth from the very center outward.

Are there any books, videos, essays or other resources that have significantly impacted your management and entrepreneurial thinking and philosophy?

I read a book, “The Art Of Possibility,” during the time between Sip Me’s closure and Vida’s opening which was about a year. I was drawn to it because I was in a really dark space of wondering what was next, feeling so defeated, and having severe panic attacks and anxiety. I was also going through a divorce at this time and all of my worst-case scenarios had just happened both in my business and my personal life. I felt very alone, very scared, very isolated, and very unmotivated. I was essentially hermiting in my home each day because it was the only thing that felt controlled and safe. I was really looking for something that would spark and kind of fix these deep, challenging feelings of loss I was experiencing. Everything I had built for decades was gone. I bought the book based off its title. I didn’t even read the synopses. It wasn’t what I was hoping it would be, but it was exactly what I needed. It spoke to how we interact with those around us, our expectations, how we communicate and how we lead. While reading it I kept finding myself thinking, man if I only had a do-over I could do this, it makes sense. I think when we are building a business, or a relationship (which really is what business is… the relationship we have with ourselves and others) that we strive to be what we think we need to be. For me, this had meant previously wearing all black, dying my hair icy blonde, and upholding the female CEO’s that I had seen in movies. With that came an inauthenticity in almost every moment with every team member because I didn’t feel like I, as I was, was enough or was what the business, or team needed. I didn’t know how to communicate, process, decide, and really be at that level that I required of myself. I felt like I was constantly wearing a mask. It caused a lot of problems. I am not proud of the owner I used to be. I’m grateful for that version of myself and understand I did what I felt was needed in that moment but now my goal is to do better and be fully authentic with the team members that work and build these companies beside me. I wasn’t terrible, but I was constantly working to be the best of the status quo which is not what I think teams, people, or we need. In meeting the status-quo it dulls or completely removes the magic of how special each of us is, what our biggest strengths can be as leaders, and really standardizes a position that I personally don’t think can, or should be standardized, Ownership. How we run our companies should come from a place of deeply authentic being that’s aligned with who we truly are. That comes with a lot of responsibility too, and the ability to hold yourself to a high standard of holding space understanding that your job is to hold space for your team and not really the other way around. There are safe, appropriate outlets to vent, to feel, to explore, to digest, to plan, to work on communication, to grow that doesn’t involve our teams, being reactive with them, or holding them to the status-quo standards individually or together. That allows you to create a space of safety and stability for the team which is key to morale, to success, to everything. Reading that book helped me see my team members and myself more fully and that brought less fear, more compassion, better communication, and overall a better, healthier, balanced experience for all of us. I still make mistakes. I’m sure I have former Vida employees who would gladly vouch for that, but the difference is in how I approach those mistakes both in myself and others and the standard I hold myself to in creating a stable, balanced work environment.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

I think the biggest lie in business I’ve ever taken on was that I had to depersonalize business, and really run my businesses and corporations as this steel-walled, unyielding, put together, “strong” woman with an armor on. That belief lead every interaction, and communication I had from 2014 to 2022. That’s a long time to carry the armor of something that you are not. I’m not surprised everything happened how it did and now I am even grateful for it. Losing everything at once stripped me down and really let me rebuild from a space of who I really am, and what feels good. Because these businesses and corporations we build… why do them if they don’t feel good? It just doesn’t make sense to spend our time, money and resources that way in the pursuit of something that comes and goes (financial success). We left the stable, steady world of working for others because we wanted to be able to have the freedom to be as we are in many cases. We just so easily get stuck in the fallacies and optics surrounding beliefs of how you should own a business and what that should look and feel like. It can be a dangerous space to get pulled into. Your business almost always checks that though at one point or another. I’m sure 10 years from now I’ll look back at maybe even this very moment and be like oh wow… I had no clue even then. As I sit here laughing I know that in many ways I probably don’t have a clue. But one things for sure.. I know a lot more than I did in 2014 and I sure am committed to continuing on this new path forward.

Contact Info:

• Website: https://vidabysipmemaui.com
• Instagram: @sipmemaui @hallowed_home

Image Credits

Jenny Vargus Photography