Jessica Hershfield of ‘Just Enough Wines’: “Celebrate the journey”

Celebrate the journey. When starting a business, it’s easy to constantly think about the next step. It’s important to celebrate the milestones, as small as they may seem to you. Celebrate the first sale, the new hire, the 100th Instagram follower. They may seem small at the time, but they matter, and they are all […]

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Celebrate the journey. When starting a business, it’s easy to constantly think about the next step. It’s important to celebrate the milestones, as small as they may seem to you. Celebrate the first sale, the new hire, the 100th Instagram follower. They may seem small at the time, but they matter, and they are all steps along the journey to the “bigger picture.” At Just Enough, we start our weekly team meetings with wins from the previous week. They can be personal or work related, and you can shoutout someone else or yourself, but we try to focus on the wins every week.

As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of interviewing Jessica Hershfield, Founder and CEO of Just Enough Wines. Jessica, a Stanford alum, pursued a career in big tech, working at Google, Uber, and Lime; before following her passion for wine. As a first time founder, she is excited about reinventing canned wine for the modern consumer.

Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?

Since graduating from Stanford, I have pursued a career in big tech. I began my career working on Google Glass, helping run their physical retail stores. I left and joined Uber, starting in Singapore as one of the first marketing hires in the region. After a year, I wanted to have a bigger impact on the broader rider population, so I joined the Product team in San Francisco. After 3.5 years at Uber, I left to pursue other ventures. I knew I always wanted to start my own company, and I tried and failed at starting an alcoholic popsicle company (yes, there is a theme of alcohol in my life). At that time, I was not in the right headspace to start my own business. A few months later I was asked to join Lime to help start and grow their Product Operations organization.

Despite the innovation in big tech, throughout the years I found myself unfulfilled. I was wondering why I was not following my passions. At the end of 2019 I was in Spain, wine tasting, and dreading going back to work. I was much more fascinated by the culture of wine, then the inner workings of a scooter. Wine has always been something I have loved. I wanted to solve my own problem — either drinking too much wine, or not finishing the bottle and wasting it a few days later; so I landed on a single format solution to wine. After a year at Lime, I left, and started Just Enough Wines in the beginning of 2020.

Living in San Francisco, I naturally gravitated to canned drinks as a portable and convenient way to take with me as I explored local parks and beaches, but I struggled to find a canned wine that actually tasted… good. I couldn’t understand how there could be an incredible wine region an hour drive from me, but I couldn’t find a canned wine solution that held up to the quality of wine found in a traditional bottle. I set out to make a canned wine that escapes the poor quality expectation, allowing us all to drink the wine we desire whenever and wherever we want.

Can you tell us a story about the hard times that you faced when you first started your journey?

The biggest challenge I faced, and continue to battle with to this day, is Imposter Syndrome. When starting your own business, you have to constantly prove to yourself that you can do it. You have to have the faith and confidence in yourself that no matter what people tell you, you can do what you want to do. Sometimes the biggest person you need to convince is yourself.

When I first started Just Enough Wines, I had so many people tell me that canned wine is never going to work. People assume canned wine is crappy wine, and getting people to pay for a premium wine in a can just isn’t going to happen. That exaggerated my own self-doubt, often asking myself why I could do this. I had no experience in the wine industry, why on earth do I think I could do it?

Where did you get the drive to continue even though things were so hard?

During this time, I turned to my closest advisors for help. My partner, my family, my colleagues, and (honestly) my therapist. The best advice I got was just do one thing each day. In the beginning of starting a business, it often feels like you’re wading through mud. I often would ask myself, what am I going to do today? How am I even going to start?

But I heeded their advice, and just did one at least one thing each day. Whether that was coming up with a name, calling an advisor in the industry, or even filing for my LLC, I made sure I felt accomplished each day. Eventually, each step adds up, and you get some traction. One day you’re thinking what should I do today to drive this business forward, and the next you’re thinking how on earth am I going to get all this done.

So, how are things going today? How did grit and resilience lead to your eventual success?

Excitedly, things are going really well. We launched our first cans, a Pinot and a Chardonnay, in late September, and have seen really strong sales growth with those. We are launching our first sparkling, Brut Bubbles, in December, and I can’t wait to see where that takes us.

I strongly believe we would not be where we are today, especially as fast as we have gotten here, without grinding away. When you’re starting a business, you really don’t know what’s going to work. What marketing campaign will be successful, what ad is most relatable, etc. All you can do is test, and double down on what works best. That requires constantly evolving, and true grit.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I live in San Francisco in a walkup apartment, and my apartment is my office. One morning this massive truck pulls up and calls me stating he has my 6 pallets of shippers here for delivery. If you’ve ever seen a pallet, you know it’s not going to get up the stairs to my apartment, and it’s not going to fit in an SF apartment, let alone 6 of them.

Lesson learned — double and triple check your orders with your vendors to make sure they have everything correct!

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

I am so proud of the brand identity we have created in such a short time. Even though we are a very new startup, we stand for keeping the passion in the work we are doing, and doing it in an inclusive, sustainable, and transparent manner.

Our brand identity was crafted very proactively, and was not taken lightly. Before we even started creating our look and sourced our wine, my co-founder and I spent months on our company’s ideals and themes. We created a narrative for what our company would look like if it was a living person, and from there we built our brand. When starting a company, I highly recommend spending time on defining your identity even before you dive into your brand in order to maintain consistency and honesty throughout everything you do.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

All I can say is burn out for an entrepreneur is real. You might think you can be that exception who can work round the clock to make your business happen in a successful way, but truthfully you probably cannot. It is OKAY to admit that.

The one tip I try to give, and live by, is make sure you are still taking time away from your business and computer even when starting your business. You will be a better founder if you can give yourself the time to refresh your mind and come back to your work. I most recently did this during Thanksgiving. I love Thanksgiving, and as hard as it was, I proactively turned off all work related notifications for the four days I was off to allow myself to refresh.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

Yes — so many people have helped support me on this journey, and I am eternally grateful. My family, my friends, and all the people in the industry who took my call when I reached out to them!

One particular person has really pushed me to start my own business and believe in myself is my partner Bradley. It’s somewhat ironic, but he is also currently one year into founding his first business, Mylance. I was wine tasting with him a year ago, and complaining about going back to work, and he was the one who really advocated for me getting the life that I wanted. He helped push me through my own imposter syndrome and be able to find the confidence in myself to start Just Enough Wines. I was worried when we were going to be a two entrepreneur household starting businesses at the same time that it would be incredibly difficult, but we have been able to learn through each other, and I think help grow our businesses together.

How have you used your success to bring goodness to the world?

I mentioned above how proud I am of our brand identity. One thing we strive for is making wine more sustainable. The glass wine bottle is the largest contributor to the carbon footprint of wine. In comparison, our cans are infinitely recyclable and reduce the overall carbon footprint of shipping and producing wine. In addition, we donate one percent of our revenues to environmentally friendly non-profits.

What are your “5 things I wish someone told me before I started leading my company” and why. Please share a story or example for each.

  1. Patience is key. Starting a business is a huge test of your patience, especially when you’re in the wine industry. Growing your customer base, and rarely happens over night. Just keep doing the things you believe are right, and over time, you will see your business grow (even if it’s not as fast as you want it to be). The adage is true though, patience is bitter, but the fruit is sweet.
  2. Continue to find ways to maintain the momentum. Starting a business requires a rekindling of momentum over and over again. Three weeks after launch, I found myself totally unmotivated. The high of seeing our product come to life had run out, the monotony of quarantine hit, and I was feeling stuck. I needed to kickstart my momentum again, so I took a 48 hour complete break from work, and replenished myself by taking time for myself. Sometimes it requires taking a step away for a moment, being kind to yourself, and refueling yourself in order to find that momentum again.
  3. Celebrate the journey. When starting a business, it’s easy to constantly think about the next step. It’s important to celebrate the milestones, as small as they may seem to you. Celebrate the first sale, the new hire, the 100th Instagram follower. They may seem small at the time, but they matter, and they are all steps along the journey to the “bigger picture.” At Just Enough, we start our weekly team meetings with wins from the previous week. They can be personal or work related, and you can shoutout someone else or yourself, but we try to focus on the wins every week.
  4. Hire smart, enthusiastic people. Hiring awesome people is by far the most important way to drive the business forward. Finding my co-founder was a step change for the business, it allowed me to have someone to bounce ideas off of, motivate me, and take on the enormous amount of responsibility. Beyond that, finding people to help drive awareness, which I will admit is not my strongest area, has been incredibly important. I have been so impressed with the creative thinking of the team I have brought on, and believe they have really helped shape the voice of Just Enough.
  5. Ask for help. I knew nothing about the wine industry before starting Just Enough except that I loved drinking wine. The most important thing I have done to drive the business forward is to ask for help. Whether it was reaching out to a random person on LinkedIn, or asking a close friend for a connection, every time I asked for help, people were more than willing, and it allowed us to move the business forward faster.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I took a leap, and escaped the “expected” of my reality. I would love for people to take a step back from their day to day expectations, and really think about why they are making the choices that they are making. Are you expected to be in a certain job, or hold a certain title, or live a certain way? Does this make you happy? I would love for people to holistically think about the life they want to lead and take steps to make that happen. It won’t always be easy, but I truly believe there are ways to make it happen if you try.

How can our readers follow you on social media?

You can learn more about our company and myself at We’re also available on social media @justenoughwines, and my personal page @jesshershfield.

This was very inspiring. Thank you so much for joining us!

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