Want to know the basics of finding and starting a side hustle opportunity? Then you’re in the right place! Two of our Wine Guides, elite leaders Elizabeth Allen and Kim Courtney, talked with us about how to start—and grow—a successful side hustle business from home. Take a look at their tips, and see if you have what’s required!

Tips For Starting Your Side Hustle Business

1. For your launch event, go big or go home.

If your side hustle is in the realm of direct selling, host a big launch event. Take selling wine, for example: A newbie’s first Wine Tasting should include a ton of family and friends, so you can show them what you’re going to be doing with Traveling Vineyard while also letting them try the wine. Since you will be with people you’re closest to, it’s like having a practice round you get paid for—you’ll learn what you did well, what you can improve on, and get some experience under your belt.

2. Market yourself.

People who are most successful in any side hustle are those who can quickly break out from their friends and family circle. Once you find something you truly believe in, get out there and market yourself in any way possible.

When Kim first started her Wine Guide journey, she made a “rule of five” for herself: “I set a goal to reach out to five different people every day. I didn’t approach each person in the same way, and I used all of my resources (email, Facebook, calling a friend). Even if I got a ‘no,’ I knew that, if I continued consistently, somebody would be interested.”


Watch this 20-minute video for a taste of what being a Wine Guide is like.


3. You don’t have to “know it all” to get started.

Both Elizabeth and Kim made it clear you don’t have to know everything about your side hustle business before getting started. Their advice for prospective Wine Guides is as follows:

  • Know what you have to know now, like using the website, how to place orders, etc.
  • Learn what you don’t have to know until further down the line. Things like product details, wine insight, etc., can come with time and study.
  • It’s wine—don’t overthink it! People love wine tastings because they are enjoyable. Keep it simple, and don’t be too hard on yourself.
  • Remember that if you forget something, no one knows except you. Especially when it comes to other direct selling companies with huge catalogs, you don’t have to know everything. Be confident that even if you don’t know, you can find the answer.
4. Set up a spot dedicated to your side hustle job from home.

Whether it’s a set-apart office, a corner of the dining room, or a couple of shelves and a filing cabinet, designate a space that is used only for your side hustle. Research shows that working a side hustle job from home is more successful when you designate a “home office” and work there consistently.

You should also dedicate separate financial accounts, if possible, to your side hustle business so it’s easier to file your tax returns.

5. Strive for routine and structure.

Many people thrive in routine, predictable environments. A side hustle for moms can present a challenge in this area—trying to schedule your two-month-old and/or two-year-old every day isn’t exactly possible 99% of the time. Instead, give yourself a general time frame to work. Maybe that’s in the morning before the kids wake up or for a while after they’re in bed. No matter when it is, be consistent. (And check out this article for some jobs that may interest you as a stay-at-home-mom.)

6. If you don’t work well with structure, plug your side hustle business in wherever you can and work on it daily.

Kim initially tried to have routine and structure in doing her job but found it made her frustrated. She knew her time was valuable, and the reason she wanted to be a Traveling Vineyard Wine Guide was because she wanted to be with her kids first and foremost.

That’s what she loved about Wine Guide life—she could work at home, on her own schedule, taking just a couple of minutes a day. “Take those couple minutes you have and keep your business going. Make those minutes meaningful.”

Elizabeth added, “Do what you can where you are, and when you have time. Some days, I can get in 30 minutes at a time—and that’s OK! Work with what you have, and as long as you’re touching your business every day, you will continue to move forward.”

7. Take advantage of training opportunities.

Whatever chance you get to improve your side hustle business, take it! Whether you’re in direct sales or have another side hustle job from home, pay attention to ways you can grow your knowledge and take advantage of them. For new Wine Guides, that means enjoying our robust training program. It’s so helpful that longtime Wine Guides like Kim and Elizabeth jokingly say they’re jealous at how fun and easy it is to train to become a successful Wine Guide now with our improved training platforms.

8. Understand your tax situation.

This is critically important: You must understand and manage your financial and tax situation if you want to be successful at your side hustle. From saving receipts to logging mileage to knowing what to write off, we go into how you can prepare financially in our article, Tips For Tax Season: Independent Contractor Tax Deductions.

9. Do your research before you commit to a side hustle.

Before starting a side hustle, you should spend a lot of time making sure the opportunity is legit. Check out reviews of the company you’re interested in. Talk to people involved in the companies you’re considering. Do everything you can to understand the reputation, startup costs, and payment plan of the company you think you want to join.

You should also understand the difference between multi-level marketing and pyramid schemes. (This article can help with that.) You may have friends who compare legit direct selling companies to pyramid schemes, but they’re completely wrong—there’s no real comparison.

Make sure you understand how much money you’re actually going to have to spend to start your side hustle business. If you can’t get clarity on this issue, or you spend money without getting anything for your investment, that’s not a legitimate opportunity. Our team is passionate about this, which is why we’re transparent about our pricing—you get way more in the kit than your initial $189 investment.

Finally, you should make sure you understand the fun stuff—like how you’re going to get paid!

What happens when you need help?

The answer to this question is one of the reasons it’s so crucial to pick a reputable side hustle. Some companies leave their representatives out in the cold once they’ve gotten their money—and they give all direct selling companies a bad name.

According to Elizabeth, “We have one of the strongest support systems of any company I’ve ever encountered. People leave other companies and come to Traveling Vineyard and say they’ve neverexperienced support the way we do it. We are a tribe—a family—and no one’s on their own as a Wine Guide.”

Specifically, Kim and Elizabeth listed several ways Wine Guides get support:

  • Wine Guides across the country, within your own team of Wine Guides, and especially the Wine Guide who initially helped you get started, are behind you and cheering you on.
  • There are dedicated Facebook groups with thousands of Wine Guides who respond to questions almost immediately.
  • Traveling Vineyard World Headquarters is a great resource. With other direct selling companies, you get passed around to people in another country; with Traveling Vineyard, our customer support is a close-knit, local crew dedicated to helping you and answering your questions. We even call them our Cheerleaders because they’re so committed to our success.

Thanks to our Wine Guides for their tips on starting a side hustle business from home. To learn more about how you can work from home as a Wine Guide, just download the guide below.


Find a Wine Guide

Before you can place an order you’ll need to get a local wine guide, to help you with future purchases or to participate in wine tastings.