How We Started A $75K/Month Wine Club

Published: September 10th, 2020
Alessandro Pepe
Roscioli Wine Club
from Rome, Metropolitan City of Rome, Italy
started June 2017
market size
avg revenue (monthly)
starting costs
gross margin
time to build
270 days
average product price
growth channels
Brand Authenticity
business model
best tools
WordPress, Stripe, Zoom
time investment
Side project
pros & cons
32 Pros & Cons
6 Tips
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Hello! Who are you and what business did you start?

Ciao! We are Alessandro Pepe (Italian) and Lindsay Gabbard (American), founders of the Roscoli Wine Club, and partners in every sense - love included. We, along with 2 other partners, manage Rimessa Roscioli, a wine-focused restaurant of the Roscioli group in the heart of Rome, which is arguably the best wine bar in Rome, if not the world (Lindsay moved here because of it, even if she says it was me).

As a side project to our wine tastings, we have started a wine club with 4 different levels ranging from 179€ - 1,000€ (paid 4x per year), designed for everyone from everyday wine lovers to serious wine connoisseurs. In the Roscioli restaurants, we serve clients who know wine is red and white, as well as clients who perhaps have a more sophisticated palette to go along with their Park Avenue apartment, and who enjoyed a La Tache with dinner last night.


We are quite proud to say that our wine club is about to cross the 1,000 member mark with annual revenue of 1 million euros after just about 3 years, built for the first 2 years by just us.



What's your backstory and how did you come up with the idea?

A bit about us. Alessandro is a crazy, passionate, deep, cultural Italian and we could call him the dark side of the force. He has worked with wine for over 20 years, hosted more than 5,000 tastings, managed Roscioli’s cellar, and has worked as a sommelier under the mentorship of Maurizio Papparello.

Our mission and goal were simple - we would create the best possible wine club in the world and one that we would be excited to be a part of - with Italian wines from small producers, farmed organically, minimal sulfites added, respect for the land - and put the winemaker's story in the center of it all.

Before that, he had opened 3 wine bars in Dublin, has acted, produced documentaries, edited videos, and has brought all of this experience along with the enjoyment of hosting wine tastings at home for his friends when he opened up Rimessa Roscioli. Born of an anthropologist mother and a philosopher father, he was able to create a unique, convivial, and cultural - yet entertaining - experience which grew into a highly demanded and a #1 to-do event on TripAdvisor for years. Anyone who meets him will never forget him.


Lindsay’s passion for wine and travel started during college and reached a fever pitch when she relocated to Santa Barbara, California, allowing for a more intimate experience with wine than she’d experienced in her native Michigan. You could call her the sunny, light side of the force.

She met Brian McClintic from SOMM who had encouraged her to study more formally with the Court of Master Sommeliers, but she understood that wine was not about reading and studying - it was about experiencing. This understanding would inspire a 10-week solo adventure across Spain, France, and Italy where she would ultimately meet Alessandro Pepe at his famous tasting, leave dumbfounded and in awe, and do a complete life U-turn to return to Rome to explore, amore, art, and to live a more deep and sincere version of Eat, Pray, Love or Under the Tuscan Sun.



Back to business…

Wine clubs are certainly nothing new, at least in the US. They are quickly finding their way into the Old World, but we do find that they require much more explaining- likely because wine is already so prevalent and accessible here (this will be discussed more later). But, having come from California and has been a member of multiple wine clubs, I knew exactly what I didn’t like about them.

  1. There was the inevitable buyer’s remorse - many times the nostalgia of the moment, the beauty and pleasure you had at the winery/vineyard, made the wine taste better but once home and back in your monotonous routine, the wines were often a letdown.

  2. A lack of variety - the wines were often the same several grapes (Cabernet, Merlot, Chardonnay, Sauvignon Blanc, etc) repeated ad nauseum, with a diminishing excitement in a short time, and left your curiosity parched.

  3. Undrinkable wines - many don’t know that when certain companies do private labeling (found often mass-market clubs), they can fabricate lofty market prices which cannot be cross-referenced through wine sites and often those wines cost less than $2 per bottle and are passed off as $20+ values.

  4. Out of this world’s prices - many Napa producers promise special allocations and exploit supply and demand. In the end, you get a few falsely induced expensive bottles, and nothing more than a short write up of how prestigious the wines are, but they leave something to be desired.

Our mission and goal were simple - we would create the best possible wine club in the world and one that we would be excited to be a part of (since 99% of them we would never join). The wines would be Italian and from small producers, meaning farmed organically, with minimal sulfites added and with respect for the land (with some French in our Collector’s Club).


People want to know the origins of what they consume these days, so we give them everything we could short of paying for them to visit the winery with us. Each wine would come with a 10-minute video (with subtitles) of the winemaker speaking of their tradition, terroir, vineyards, cellar and we would select wines from ALL over Italy to give members the idea of doing a ‘wine tour’ from the north to south Italy with unique wines and to show off the lesser-known grapes since Italy has more than 1,800 grape varietals.

Essentially we would give them every tool to host their tasting for their friends and let them be the expert or sommelier of their group. Plus, we believe that Everyone can be a Sommelier...

Take us through the process of designing, prototyping, and manufacturing your first product.

Our Wine and Food Tasting dinner’s success made it the perfect roadmap to creating the wine club and this would allow our clients to essentially ‘recreate’ the tasting back home. So following that, we always included 1 sparkling, 1 white, and 4 reds until ultimately we had enough demand for a reds only assortment, and so we offered that option as well. We included a video with each wine, highlighting the producer and details about that wine, region, pairings, etc. so that members would have the same information at home that we had to describe the wines in our restaurant.

We shipped with Mail Boxes Etc. for the first year and to explain how slow and antiquated Italy can be. For the first time in my life, I found myself writing labels on boxes with carbon paper, like a dinosaur - I hadn’t seen that stuff in 30 years!!

Shipping for us can be complicated with ever-changing laws and customs but we have always risked and found away. In working with multiple shipping companies, we can now ship to the EU, all US states (except Utah), and most other countries (except for Canada, South America, and a few others.)

Initially, we did quarterly shipping but as we grew this became unmanageable due to the summer heat and our fulfillment schedule requires an insane amount of data entry plus another 3-4 weeks for packing/shipping. We consolidated our shipments to twice per year, saving us time and money, and now we can even use fast boats for the first leg of the journey to the US, which saves us nearly 30,000€ per shipment.

Describe the process of launching the business.

Looking back, our launch was more of a stone toss than a ‘launch’. We were two people managing everything - traveling to take the videos, writing all the notes, packing the boxes, editing the myriad videos, all while running a busy wine bar, and in Italy meaning lightyears behind in technology, utilizing Gravity Forms and PayPal to collect data from the subscriptions and managing everything with a manual entry in excel. Archaic.

We know it often takes up to 7 touches for people to buy. Collecting emails to maintain a near-constant engagement has been crucial to our success.

Launching the Roscioli Wine Club was little more than sending a newsletter to maybe 10,000 subscribers via Mailchimp and promoting it nightly during our famous Wine and Food Tasting Dinner.

At that time we said we’d be happy with 1,000 members and that became our goal. Over time we’ve adjusted our goal to be closer to 2,000 members, (with the ability to scale up to 5,000 members) but beyond that, it would be quite challenging to offer the quality of wines that we provide now from small family-run wineries with annual productions of less than a few hundred cases of each wine.

Since launch, what has worked to attract and retain customers?

What haven’t we done?! Our wine club has been upgraded at every turn in the last few years.

The wines have been upgraded in quality and become more exclusive with every single shipment as our buying power and volume discounts improved.

We do special collaborations with our winemakers to create exclusive bottlings available only for our wine club and not available in the market. Reaching several hundred members allowed us to purchase a barrel to vinify it the way we see fit and to allow winemakers to experiment in ways where they might have worried before, not knowing how the market would react.

Our comprehensive companion content has become more professional and timely, and we stay in constant communication with our members.

We give small gifts like extra virgin olive oils or balsamic vinegar in each box.

We offer our members free tastings, travel tips, online streaming tastings if needed, the chance to go with us to wineries or help them plan their wine tours in Italy.

And most recently, we built out a new platform called to give our members a free online wine school for their wines and to learn about wine in a more genuine, human way instead of from dry, technical books.

Sharing is caring - that is our motto. We love to give, give, give. Even our clients sometimes look at us with perplexed eyes saying “I get ALL that when joining?

How are you doing today and what does the future look like?

We are just coming out of the first wave of COVID-19 but just before that we were on target for our exponential year. The center of Rome is devoid of inhabitants, and without tourism, it would be challenging to stay afloat, so having the wine club in place was an immense savior and has allowed us not to fire a single one of our 27 restaurant employees. And certainly going forward, it gives us a lot of protection to be able to work remotely and digitally.

The future is looking bright especially thanks to our project and rethinking how the wine industry will look going forward. One trend we see is the desire to cut out the middleman - consumers don’t want to pay the added costs involved and our wine club helps to eliminate the need for importers and distributors, yet gives everyone the tools to learn about wine, the winemaker, their story and to connect to the winemaker themselves.

Our attrition rate is down to about 3%, which suggests that our members are extremely happy. And our refer-a-friend program is up 150% from last year.

Our major plan this year is to work with affiliates and possibly a PR company in the US, as our current needs involve establishing a greater reach.

We also hope to expand our Italian member base but we know it will take repositioning the product we sell to be more of a wine school with wines to accompany it, versus a wine club with a free wine course to accompany it. One of the cultural differences we face with our user base is that Italians don’t see the value in just having wines curated for them.

Through starting the business, have you learned anything particularly helpful or advantageous?

First and foremost, wine cannot be promoted in the same way that other products can be promoted. For example, if you say Gucci or Tesla, everyone knows those brands, but if you say Domaine de la Romanee-Conti, even many wine lovers and students don’t know it’s the most important wine in the world.

Wine is different - it’s a cultural experience, and not following all the mass marketing rules has probably saved us... even if we have sacrificed numbers, we have never sacrificed our souls. We know we have a niche market and prefer to hone in those rather than ones who are just looking for cheap wines to imbibe on. This is something that Alessandro always reiterated to marketing teams who thought we would fit into their cookie-cutter strategies.

Offer free shipping! No one wants to pay for a service that doesn’t give added value.

One of our best decisions we ever made was to work with an American company, PXLPod Web Strategy, for our website and custom store management since we didn’t fit into any standard subscription software with our custom shipping schedule. Americans, generally speaking, and respective of Italians, have a more rational and efficient approach to business and are 10 years ahead of us in Italy in terms of technology.

We know it often takes up to 7 touches (!!) for people to buy. Collecting emails to maintain a near-constant engagement has been crucial to our success through the use of coupon pop-ups, a free downloadable pairing guide, and other lead magnets, utilizing our reservation system to pull them, along with learning to ‘use’ the brand Roscioli (even if we operate quite separately). Putting links on their pages and cards in their business has been helpful and our next goal is to get their team on board with promoting the wine club, even if they are usually too busy to think about it.

We had used Facebook Ads and surely they helped but our return was always quite low, even after several months, so ultimately we bailed on that as a strategy.

What else… Say yes, then figure it out later. You have to spend money to earn money. Sometimes our digital marketing efforts seemed fruitless but over time, we always noticed strong growth so clearly something was silently working. Spend more of your time finding a multiplier or an idea and watch how 80% of your successes can come from just 20% of your efforts. Figure out what you want and what is important in life.

And the most important, read books.

What platform/tools do you use for your business?

We are in Italy, so unfortunately some logistical tools are not available (ie. linking our store with FedEx for ease of printing labels, etc) which would be immensely helpful, but we continually put pressure on our logistics suppliers to put automated systems in place to improve customer communications.

Asana has been wonderful for working remotely and as acting as a project manager to reinforce tasks to be done and deadlines.

Probably the most critical platform we are using is for - our online wine school and social network - which integrates BuddyPress, BuddyBoss, LearnDash, GamiPress, and WordPress. This combination of platforms has provided us the ability to have an all-in-one community, with a social and learning component, gamification, and rewards, without having to resort to relying on Facebook. BuddyPress gives us ownership and control of our community and will allow us to market better to members over time without being a slave to Facebook’s terms and conditions as well as the insane risk of building our business on a platform we neither own nor control. It does have its limitations as a desktop site but we are working to develop a native mobile app in the Fall when the developer has availability which will solve 90% of our frustrations with integrated notifications and for the ease of logging in at your fingertips.

Beyond that, Mailchimp is our main lifeline for marketing, newsletters, and my personal favorite, automation.

What have been the most influential books, podcasts, or other resources?

The 4-hour Workweek by Tim Ferriss - Tim reminds you to work smart, not hard, as time has a value, and to outsource that which you don’t need to be doing or that isn’t worth your time or mental energy. This frees up mental space for ideas and creativity, and oftentimes it is not more work than yields more money, but an idea or better yet, a multiplier. The multiplier has exponential capabilities for a business.

Simon Sinek also delivers a powerful TED talk How Great Leaders Inspire Action. The why we do what we do is not only important for our customers, but it’s critical to our enjoyment of life. And when people see you living your genuine passion, they will usually subscribe to anything you are selling. Probably somewhere around 95% of companies start from what they sell, not the why they sell it, and that makes all the difference in building trust and long term relationships.

Advice for other entrepreneurs who want to get started or are just starting?

Do you know how Martin Scorsese decides to create a film? He sits down in the seat of the movies and tries to imagine what he would want to see. Put yourself in that position every time you can to think about the user experience, from sending newsletters, call to actions, to social posts, to website layout, and user flow. Put yourself in the driver seat and test everything.

The biggest mistake we see is everyone offering the same thing into a crowded marketplace. For example, how many more bars can be opened which all serve alcohol, all have the same hipster decor like the vintage light bulbs hanging from the ceiling, refurbished wood elements. Do something unique! Even if you don’t know if it will work from other’s past successes, you’ll have a lot less competition in the long run.

And lastly, figure out what you want in life. For us, reading, writing, storytelling, and traveling is our passion and our goal. We need some money to do it, but time is ultimately what we desire. If what you sell can blur the line of work and true pleasure, I think you are going in the right direction.

Are you looking to hire for certain positions right now?

We are always welcoming affiliates and open to strategic partnerships. Please reach out if you think there could be mutual interest.

Where can we go to learn more?

If you have any questions or comments, drop a comment below!

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