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Holly Berrigan of MYSA Natural Wine: “Camaraderie ”

A passion — Like I mentioned before if you don’t absolutely love what you’re working on, being an entrepreneur in that area is a terrible idea. There are so many days that are hard, much harder than working at a regular job, and if you don’t have the fiery passion for what you’re doing in your gut […]

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A passion — Like I mentioned before if you don’t absolutely love what you’re working on, being an entrepreneur in that area is a terrible idea. There are so many days that are hard, much harder than working at a regular job, and if you don’t have the fiery passion for what you’re doing in your gut then the likelihood of you quitting will increase significantly. You can ask anyone that knows me and they’ll tell you how annoyingly obsessed with wine I am. It’s hard to get me to stop talking about it. That passion keeps me committed to my company.


Being a founder, entrepreneur, or business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, slump, and anxiety. So how does one successfully and healthily ride the highs and lows of Entrepreneurship? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur” we are talking to successful entrepreneurs who can share stories from their experience. I had the pleasure of interviewing Holly Berrigan.

Holly Berrigan is the founder of MYSA Natural Wine, the premier destination for buying, discovering, and learning about natural wine online. As a serial entrepreneur and current sustainable agriculture student, she’s built a platform focused on sustainable consumption through partnerships with organizations like 1% for the Planet and The Carbon Fund. She has a WSET Level 3 certification with Distinction, is a member and writer for the Porto Protocol and Slow Food USA, and is a student in Sustainable Agriculture at the University of Massachusetts Stockbridge.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Most of my life I wanted to be a diplomat, so I studied languages in school, lived abroad for many years, and then, unfortunately, wasn’t able to pursue that path for personal reasons. Shortly thereafter, I was feeling lost while working at a consulting firm and started taking wine classes as a hobby. Having built up many other companies’ sales and marketing programs I started to get the entrepreneurial bug and decided to start a wine company that ultimately became MYSA Natural Wine.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

I knew I didn’t want to be in consulting forever but I didn’t have another passion because the foreign service was off the table. My “Aha Moment” was during a day when I was feeling really lost, someone guided me to look at my bookshelf to understand what I really cared about for clues. Just looking at the shelf I saw several books on wine and a couple on entrepreneurship. The more I thought about it the more I knew that working in wine made a ton of sense because I already spoke French, Italian and Spanish, had lived in those countries, and even knew their trade organizations from having worked at the embassy in Rome. In that moment it clicked and I decided I was going to start a wine importing business.

In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?

I was definitely not born an entrepreneur, I had always thought I’d have a government job that I loved and focus on that completely. That said, I was always a “go-getter” or creator and wanted to have multiple projects going at the same time, which is a typical trait of serial entrepreneurs. No one was surprised when I told them I wanted to start a business, but it certainly was not in my initial plans.

Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?

No one in my family or close friend group is an entrepreneur so I initially struggled with figuring out how to set everything up and read a lot of books to try to bridge the gap. I had been working on the business passively for about a year when I met my now partner and co-founder, Nic Jansson at work. He was just as into the idea of working in wine as I was, but put a bit of a spin on it with a focus on eCommerce. After he came on board things at MYSA really started to take off with timelines, new websites, real budgets, customers, etc. and the rest is history. If he hadn’t come on board I’m pretty confident the company wouldn’t have ever turned into anything besides a side-hobby vs our full-time jobs.

What do you think makes your company stand out? Can you share a story?

MYSA is definitely very niche, as we operate in the natural wine space. It’s a small but growing category of the wine industry and our goal was to make natural wine accessible to people across the US. I’m from Oklahoma, and finding natural wine at all would have been very difficult even as recently as a couple of years ago (it’s still pretty tough but it’s a growing scene there too!). Thus, our goal was to educate people about the benefits of natural wine and what is in conventional wine, as well as give people the option to ship it straight to their home!

Additionally, we’re very focused on sustainability, I’m a student of sustainable agriculture at the University of Massachusetts, and we partner with 1% for the Planet at MYSA as well as offset all the carbon emissions of the bottles we sell from the vineyard to the doorstep of our customers.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Consistency — This is the number one trait that’s needed for entrepreneurship. Being consistent and persevering even when it feels like nothing is happening is crucial. There are no such things as overnight success stories, we just hear about people’s success after years of grinding and that’s how every aspect of our business has been. We’ve been consistently showing up on social media and have had a stable growth of our community over the last 2 years. We’ve created great content for our club members about their wines each month that they’ve come to love and expect and that consistency is the trust you build with your audience, so it’s crucial to keep it up whether you have 10 subscribers or 10,000.

Centered — I work pretty hard to stay centered through my activities, rest, and diet. All the typical things you might hear like meditation, manifestation, taking naps, etc. I’ve tried it all and can say with confidence that not only is my company bigger and better since implementing these activities but I am happier, more calm, and generally make better decisions. For example, when I’m in a stressful situation I now have breathing techniques I use to calm myself and reset so I don’t make quick judgments. I truly believe this has saved our company a lot of time and money.

Camaraderie — Typically I don’t ever have a desire to kill our competition or be the best at the expense of others. I know this goes against a lot of advice about business, but at least in my industry, we are so niche that I abide by the “rising tides raise all boats.” The more people know about natural wine, whether from us or from someone else is great for everyone in this niche and the goal of the natural wine community is to be inclusive.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

I’ve made a LOT of financial mistakes with our company, which is extra painful because we have no outside funding, so it’s all out of myself and my partner’s own pockets. We initially set ourselves up with the wrong CRM that was tens of thousands of dollars in a year when we weren’t even making money yet, we signed up for services that brought no ROI at the advice of people outside our industry. When it comes to financial decisions, it can be really hard to know whose advice to take, but I would definitely say to be as frugal as possible in the beginning until you truly have a solid proof of concept, otherwise, you might be finished before you even get out of the gate.

Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?

We always try to prioritize time off and say “there’s no such thing as a wine emergency.” Both my partner and I ski so if the conditions are great we take half a day off and head out to the slopes. We also know that sometimes we may need to be on calls until 7 pm or work a little bit on the weekend so it’s important to prioritize not the amount of time working but the output and be flexible with people’s time, especially during COVID.

What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?

When we started MYSA I spent a lot of my time making content, and I still do. We write education pieces for people getting into natural wine for the first time, host events with others in the industry on trends, education, inclusivity, and many other topics that are great both for our consumers to understand more about the product they’re getting but also to bring the natural wine community together and built connections. Just creating that environment helps foster trust and credibility as well as has lots of benefits for everyone else involved in the events as well.

Can you help articulate why doing that is essential today?

I have heard lots of great quotes to the effect of “someone is out there doing what you want to do that knows less about it than you do” and I think all of that comes down to credibility and putting yourself out there. You can know everything on a topic, but someone else may be doing the work to get their name out and associated with it. Ultimately you have to know your stuff, but it’s not enough to just know it, you have to share it and put yourself out there to actually get a seat at the table on the topic.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

I have made most of them in the book as a first-time entrepreneur, but I also came from a consulting background for startups, so I’ve seen many other issues beyond my own including:

  • Not focusing enough — the more niche your audience, the better likelihood you’ll have with connecting with them, so don’t try to sell to everyone.
  • Not projecting and keeping good books — I am no accountant, but if I had not used forecasts at the beginning of our company and cash-flow projections we would have run out of money about 6 months into the business. Find a system that works for you and that you know you will keep up with so you can see where the money is going in and out of the business.
  • Not having strong contracts — especially in the beginning, if you don’t have strong contracts with the people you work with (whether service or product based) you are putting yourself at high risk for losing pieces of your company when it does take off in the future. Invest in a few hours of a lawyer’s and accountant’s time to ensure your company is set up correctly, your contracts with vendors, contractors, and anyone else are solid, and that you’re generally compliant with whatever industry you are in.

There are so many, but these three above are the biggest ones that would have saved me a lot of headaches if I had followed this advice myself.

Ok fantastic. Thank you for those excellent insights, Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur, you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?

Entrepreneurship is often glamorized as being your own boss and being free and flexible, but the truth is there are far more chains involved in being an entrepreneur than having a regular job. The buck stops with you and if there is an issue you will have to dig in to solve it and can’t clock out to deal with it later. As you mentioned, the highs are really high and the lows are far lower than you’d often experience in a regular job.

If you think it’s hard managing someone at your company, consider the idea that multiple families’ livelihoods depend on your company continuing to run and be successful each month so they can stay employed. The burden is high and with most small business owners they won’t see much if any, the monetary pay-off for it for years after the founding of the company. Another point is that even with the highs being high, say when we got a huge contract that would double our business, that also comes with the stress of realizing you now have to create the infrastructure to double your business.

Basically, unless you absolutely LOVE what you are doing every day, it’s not worth taking on the entrepreneurial burden to try to get more money or flexibility, as you’ll likely end up with less of both for a significant amount of time.

Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.

Last year we were approached by Eater to run their wine club for them. I was elated at the idea of bringing natural wine to such a large audience and the potential growth our company would see from that partnership. When we won that contract and learned that they wanted to work with us I was sky high and dancing around thinking about all the potential for both of our brands as their first product and it was a moment that validated my passion for this niche area of wine, as well as our business model.

Do you feel comfortable sharing a story from your own experience about how you felt unusually low, and vulnerable as a result of your business? We would love to hear it.

As I mentioned, we are completely self-funded, so cash flow is a huge factor in everything that we do. Last year I was running our numbers and realizing an entire business line of our company was not at all profitable that I had spent months organizing and tens of hours each week creating, promoting, fulfilling, etc. This sent me into a really dark place where I couldn’t work for the rest of the day and just felt like everything I was working towards was pointless because if it’s not profitable, then we shouldn’t even be doing it.

Based on your experience can you tell us what you did to bounce back?

I am a big fan of journaling, meditation and manifestation and use them in different ways to come with strong emotions I have. In this particular case I initially just sat with myself and let myself feel down for a little bit, then I started journaling pages and pages on what was and wasn’t working for me with that product, and many of our other business lines while I was at it. I wrote about what I loved about it, what I hated, things that I thought could be better, and ultimately, what that product line would need to do for my time invested in it to be worth it.

After I got it all on paper I immediately started to feel better (note: I really think everyone processes differently, like Nic needs to run or workout to process) and felt like I had control over what was going on again. The next day Nic and I sat down and did an analysis of all our business areas, revamped all of them to lessen the amount of time we’d need to spend on them while improving profit and we launched all the changes within a few weeks.

Ok super. Here is the main question of our interview. What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.

  1. A partner — There is a reason Y Combinator won’t take founders without a partner for their programs. Trying to do a business alone is never as effective as having someone that can share the burden of entrepreneurship with you. My company was lost for about a year before I found my partner and there is no way MYSA would be where it is today (or even around at all) if Nic had not come on board.
  2. A plan — Going into anything blind is a bad idea as we all know. Sometimes I look at our initial business plan just to get a good laugh at how far away we are from it today. But, without that initial course to follow it becomes too easy to get sucked into the small parts of running a business and too easy to lose sight of the ultimate goals. It’s ok if they change, they just need to be there to guide along the way.
  3. A passion — Like I mentioned before if you don’t absolutely love what you’re working on, being an entrepreneur in that area is a terrible idea. There are so many days that are hard, much harder than working at a regular job, and if you don’t have the fiery passion for what you’re doing in your gut then the likelihood of you quitting will increase significantly. You can ask anyone that knows me and they’ll tell you how annoyingly obsessed with wine I am. It’s hard to get me to stop talking about it. That passion keeps me committed to my company.
  4. A practice — Sometimes passion for your company isn’t enough. As you saw with my low-point story, I was feeling ready to quit even though I loved the work I was doing. Knowing yourself, how you process, and what your body and mind need to perform at their best is crucial to the success of your company. I know I need to go to bed early, wake up early, meditate, manifest (maybe workout or journal depending on the day) and have my small rituals to feel centered and ready to take on the day with a clear mind and positive attitude. They are also crucial to fall back on when you’re really down or struggling, along with your partner. Everyone is different, so find what works best for you, but don’t ignore your needs and be consistent or burn-out will come for you.
  5. Patience and perseverance — Anyone that looks like an overnight success I can guarantee had been working at it for years until they hit a tipping point and then it feels like they’re all the sudden everywhere. Most of the initial parts of entrepreneurship are super difficult and they typically stay that way for months to years before you start to see the snowball effect occurring. For us, that moment happened with COVID, as we work in the online wine space and it was taking off during March of 2020. We worked for 2 years leading up to that with other jobs and getting creative to pay the bills before we hit a point of the company being able to cover its own costs, so ensure you’re in it for the long haul and prepared for it before you dive in.

We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

Resilience to me is a mix of perseverance, flexibility, positivity, health, and support. What I understand is that we all naturally have different levels of resilience, but I would also define it as a practice and something that can be improved with self-awareness and dedicating time to working on it. To me, it is both knowing yourself and what you need to be in a positive headspace, then choosing to be in that headspace even when things aren’t going the way you would like them to for as long as possible. If you know yourself and you fall down, you’ll be better equipped to understand how to get yourself back up again and on track, as well as better conditioned to see the positives and leave that negative space quicker.

Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?

My upbringing was a bit high and low, moving 8 times during my childhood and not having one place that was ever my “home,” aside from it being wherever my family was, but it was always in flux. I also experienced having lots of money, then no money like a bit of a yo-yo during that time, which taught me that it can come and go, and I never felt particularly more happy or sad when I had money than when I didn’t. With my family constantly in flux and my personal space constantly changing, it gave me a lot of opportunities to re-evaluate who I was and what mattered in my life, as it was in boxes every couple years moving somewhere new and I had to decide if each thing was still who I was or not. This process I think brought me a lot of self-awareness that has helped me understand myself and given me a strong base to build my resilience practices on.

In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?

I am absolutely a positive person and have never understood what benefit anyone gets out of focusing on the negative aspects of situations. With that said, of course, I have fear and can go down the rabbit hole of what-ifs like anyone and my partner typically has to talk me out of those. But overall, I think it’s very important to always assume people mean their best and that things will go the way you want them to. I am also a big believer in manifestation, which means that you are thinking things into existence, so if you are thinking negative things, that’s not great, since you may just think them into existence.

Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team? Please share a story or example if you can.

Just like I said above with manifestation creating what you believe in your mind, the same happens with your attitude and spoken words to others. If I tell someone they are going to do a great job, or wow their clients with their presentation skills, or look amazing walking down a runway (always try to be specific) they are statistically more likely to do a great job because you’ve essentially manifested for them what will happen, now they can see it in their mind and are way more likely to go do it, embody it or whatever it is.

Ok. Super. We are nearly done. What is your favorite inspirational quote that motivates you to pursue greatness? Can you share a story about how it was relevant to you in your own life?

The greatest investment you can ever make is in yourself.

This quote is relevant in so many ways, especially for entrepreneurship, as you are literally investing in yourself and your passion to create it. It also focuses on areas beyond money, like investing in giving yourself time, space, calm environments, literally whatever you need to be happy and function at your highest levels. No investment is more important than that because as the leader of your company if you’re not functioning at your best then a fancy marketing plan or anything else money can buy will not be as effective.

How can our readers further follow you online?

Company website: www.mysa.wine

Instagram/Twitter/Clubhouse: @hollyberrigan

This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!

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