How To Start

I remember that particular drive home. I cried on and off for the first hour. I was wondering if I should just throw in the towel—and this was before it even begun.

Let me back up a few years.

When I came off the road from over a decade of playing music, I helped my first wife develop her freelance graphic design gig into a design firm. I mainly handled client intake, business development and conceptual branding and marketing. It was fun. But it was her thing, not mine.

I pined for a time when I could own a small plot of land near Mariposa in California, plant some Zinfandel vines and make the wines I loved at the time. Big, bold and spicy. I imagined that time to be a long ways off, like when I retired. (What is retiring for an entrepreneur but another opportunity to start something new?)

She suggested I go to work for a winery now and see if it really is as magical as I idealized it to be. So I did. I worked for one winery, then another. I asked question on question on question. I took other winemakers out to lunch and asked to hear their story. And then I started to develop a business plan for my own winery. It was to start in the basement of our Portland home. I didn’t know how, but I was certain I was onto something. And it couldn’t wait until I was retired.

A year later, a friend and I launched our winery called ENSO. We traded my basement for his garage. (Very good decision.) And after six months in his garage, we signed a lease on a commercial space near downtown Portland and opened our doors to the public a few months later.

The Comfort of Not-Knowing

I didn’t know what I was doing. He didn’t either. We both had backgrounds in winemaking, but not in owning and running a winery. Nor had either of us ever even worked in a bar. And yet.

I was so certain that my idea would work. And not just work. I really thought people would hear about this and really connect with my vision for making interesting, boutique wines that are served in a non-pretentious atmosphere. And they did, eventually.

But there was so much we didn’t know. And we didn’t even know all the things that we didn’t know! But we knew enough to start.

So let me take you back to that drive home.

Since my friend and I were essentially boot-strapping this winery venture, we thought we could presell some wine to raise funds. We would invite friends to parties and sell them wine at a discounted price. We bottled 50 cases of wine and hosted three parties, the first being in Oakland, California where I had recently relocated from.

The RSVP list was encouraging and so I brought half of those 50 cases with me, certain that I would come back with plenty of cash and no wine.

People really enjoyed themselves at this party and loved the wines. But more than that, they loved the idea of this urban winery in Portland that we were bringing into the world. And they loved my passion. Still, I only sold about four cases. I had set an expectation of what success would look like for that party and I completely missed the mark. It sunk me.

The 12-hour drive home was a long one, full of self-doubt. What the hell am I doing? If I can’t sell a measly 25 cases of wine to my biggest supporters, what business do I have launching a brick-and-mortar winery?

I listened to Elizabeth Gilbert’s Eat, Pray, Love on this solo road trip. I loved the book. And I don’t care what anyone says about that. I LOVE THAT BOOK! Her own courageous story of trying to find her self and her voice through travel. The inspirational moments, the mishaps, the lessons learned. The idea of taking a risk on an adventure felt so resonant to me. It was the idea of starting—doing something ambitious—that kept me going.

I cried for the first part of that trip home. I let myself feel the uncertainty and the unknown. And then I picked myself up, wiped my face and made a plan for what we’d do next. I trusted that we’d find a way to raise the money we needed.

There is an old joke in the wine industry that goes something like this: Do you know how to make a million bucks in the wine industry? Start with 10 million! And I must have heard this a million times from other industry professionals. Somehow it didn’t deter me. It felt so cynical and I was trying to free myself of unnecessary cynicism.

When we finally opened to the public, my partner and I would man the bar in addition to making the wine. There were a few days where we’d only have a handful of customers. We considered promotions, alternate hours and other ways to veer from our original plan. But in the end, we decided to stay our course and develop what we knew to be good and true. We stayed authentic.

And it took some time. It was a passion project for the first two years or so. We kept our day jobs and invested all our extra time in developing this project and didn’t take a penny. We pushed ourselves to the edges and kept trying to get the word out.

And you know what? It eventually paid off.

Safety is the enemy of success. — Rich Litvin

Do Something. Your Own Way.

When a local newspaper emailed me to schedule an interview about naming us Bar of The Year, I was elated. They understood the vision of what I had set out to accomplish. They saw the culture we were creating. And they seemed to understand why. I didn’t set out to change the vibe of the wine industry at large, but I did set out to do this thing in my own way. And that took courage.

I had spent enough time in the wine industry at this point to have gained some confidence in my craft. I laughed at those who took their wines so seriously. And I applauded those who were choosing to make distinct wines that told a story.

For most entrepreneurs, we do things our own way. We may find something as age-old as a winery and give it a refresh. Or we may come up with something altogether new. But part of what enthralls us is that we get to redefine or reimagine something bigger than our product. We shape culture. We flip the script and make people think twice. We question assumptions. We’re predictably unpredictable. And we work hard for our dreams and for others.

And when it works, we feel rewarded. And when it doesn’t, we try something new.

On that drive home, I felt the risk I had engaged in. And I wondered if I would actually have the temerity to see it through. And the fact that the fear was so present meant that I must push through, even if only to see what was on the other side.

And you? What is your great idea? What are you being called to do? What are you going to do with that great idea or calling? Are you ready to begin the journey to bring it to life? When you are, hit me up. We should chat.