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An Inspired Chat with Alyssa Wolf of Jessup, Maryland

We recently had the chance to connect with Alyssa Wolf and have shared our conversation below.

Alyssa, we’re thrilled to have you with us today. Before we jump into your intro and the heart of the interview, let’s start with a bit of an ice breaker: What are you being called to do now, that you may have been afraid of before?
Public speaking. In college and grad school I was close with my classmates, yet terrified any time I had to give a presentation in front of the class. My first speaking appearance after founding Red Wolf Imports was at the USA Trade Tasting in Manhattan maybe in 2018. I spent hours practicing but anxiety got the better of me before speaking and my voice shook the entire time.

As a wine importer public speaking comes up fairly often. Wine dinner, tastings, and classes to sell and promote our products. Last week I had a wine dinner with over sixty guests, and tomorrow I’m speaking at the Center Club in Baltimore for their monthly “Women in Business” meeting. Do I get a little nervous beforehand, sure. Am I anxious about it days in advance, or shaking in my boots during the presentation? Not in the least. I’d go as far to say that I enjoy public speaking. Pushing yourself out of your comfort zone is always challenging, but I’m proud of this growth.

Can you briefly introduce yourself and share what makes you or your brand unique?
Red Wolf Imports is a wine and spirits importer based in Maryland. We were founded in 2015 after I decided to change career paths and strike out on my own. Our focus is on wines and spirits from under represented regions, places with ties to a history in wine making but are not constrained by that tradition. My passion is connecting US wine drinkers with wines they otherwise wouldn’t have the opportunity to try.

Appreciate your sharing that. Let’s talk about your life, growing up and some of topics and learnings around that. What did you believe about yourself as a child that you no longer believe?
That I am shy. I’m not. Working as a physical therapist for seventeen years I talk to people all day everyday. In the wine industry I’m out in the market visiting shop and restaurant accounts, interacting with sales reps, working consumer facing events. I have simply learned that I am an introvert and sometimes the “extrovert energy” gets drained. I have learned when I am making excuses to get out of pushing myself outside of my comfort zone, and when I truly need to say no and take the time to recharge my battery.

Was there ever a time you almost gave up?
Ha, well yes, as someone who has run a small business through the pandemic I’d say so. When everything shut down we thought that would be the end. We did what we could from home but had no idea how things would turn out. Luckily for Red Wolf, we had wines in the country for the four years prior and had dedicated customers buying our products. We also forged an excellent relationship with our distributors, who were considered essential workers during that time and sold a whole lot of wine.

Shipping prices increased, significantly, in 2021 which strained the business. Now, we are dealing with the tariffs. We discussed just selling what we had in stock and closing up, but decided to move forward. We have a solid plan in place and we will get through it, until these tariffs are hopefully overturned.

Alright, so if you are open to it, let’s explore some philosophical questions that touch on your values and worldview. Is the public version of you the real you?
A little bit. I am from NY originally and tend to talk quickly, when I’m speaking publicly or professionally I slow down focus on speaking clearly. My pitch is a touch higher than my normal deep, nasal voice which softens my accent. But I like to let the private me slip sometimes when doing a presentation, connect with the crowd, make them laugh.

I also curse a whole like more as the “real me.”

Okay, we’ve made it essentially to the end. One last question before you go. Are you doing what you were born to do—or what you were told to do?
I don’t know if I’m doing what I’m born to do, but I love my work and am deeply grateful for life as it is now. When I was a full time physical therapist I think I was doing what I was told to do. As a kid I thought I’d be a doctor, because I wanted to help people. As I grew, I knew med school was not for me, and physical therapy seemed like a good path.

For many people it can be a great job. For me, at that time in my life, I took on too much. Managing a large clinic, with all the management roles, while seeing a full time caseload. I never said “no” and would often see patients before my hours, after hours, during my lunch. I didn’t receive a dime more for that, but I thought I was doing the right thing.

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