Just Ask Joy

For those times when you want to reach out for hope, answers and connection, “Just Ask Joy”. If you have a question large, small, or inconsequential about small business/business district, email me at joy@ventureportland.org with the subject line “Just Ask Joy”. Although I surely won’t have all the answers, I’m good at researching and love small business trivia! I’ll do my best to answer questions in a timely manner.

April 7, 2021

Hi Joy,

We’re experiencing such a strange time in our store right now. Some customers who have been vaccinated feel justified not wearing masks, not making appointments, and generally “bullying” their way around our Covid-19 rules. What now?


Vaccination Troubles 

Image by @drawnhungry

Dear VT,

First, major congrats on your business staying alive during this most difficult of times! You’re not the only person to mention this new challenge. While you want to encourage your customers to come in, even a few vaccinated, unintentional “troublemakers” can certainly make things rough!

In an Oregon Bartenders’ Guild meeting earlier this week, some bartenders expressed this very same, real-time issue. They also mentioned that some customers want to seat themselves indoors even if the restaurant or bar is expressly NOT yet ready (or staffed up) for indoor dining. 

I recommend enlightening your customers via refreshed, clear signage and through your social media platforms. Revise your Covid-19 instructions to say “Even though you may be fully vaccinated, our store continues to maintain the following rules: xxxxx. These rules will remain in effect until further notice.” Of course, this includes training your staff members and helping them to feel confident enforcing your regulations. 

I realize it is a delicate balance; you want customers to return BUT maintaining safety is priority #1. 

Please let me know how it goes!

With thanks,


February 5, 2021

Hi, Joy-

I have a small restaurant and we finally got our outdoor seating figured out. We bought expensive heaters, tents with sides, and blankets, too. Still, we have only a few customers. What should we do?


We Built It But They’re Not Coming

Dear We Built It,

Congrats on your outdoor seating! It sounds like you put a lot of care and intention into it so, naturally, you need to recoup your costs AND bring in additional revenue. 

Your situation is a familiar one, unfortunately. What I’ve noticed is a lack of clear communication with customers. Have you taken photos/video of your outdoor space and shared those images *repeatedly* on your website and social media? Is the seating area clearly marked that it is for YOUR guests? Often, restaurants are great about showcasing their thoughtful menus and the food itself BUT forget to “comfort” their customers with clear images of what they can expect upon arrival. Where do they park? Is there public transportation nearby? Should they wear extra layers and bring an umbrella? What’s the ordering process; pre-order, QR code at the table or at the front door? Are the tables spaced out well? In these strange times, guests are nervous and leery of the unknown. Every step of the way, show guests the great experience they can expect when they dine with you! And, as I mentioned, don’t just show them once or twice, do it OFTEN. Use social media constantly.

Lastly, if you’re able, incentive guests to use their own social media accounts to showcase your outdoor seating and your Covid-19 safety measures. Perhaps you can offer them a discounted beverage or a side of fries/small salad if they post for you. Portland diners really DO want to help and #supportsmallpdx.

Best of luck to you and keep me posted, please-


December 16, 2020

Dear Just Ask Joy,

I lease a tiny spot for my retail store. We are struggling like every other Portland Small Business. My lease expires, like, right now. Should I sign a new one?

-Worried in Portland

Dear WIP,

I am so very sorry that you’re in this COVID-19 predicament; none of your own doing, of course. 

To try to give you an answer, my first recommendation is to look at both your business bank account and your personal account. Can you withstand another year without substantial customer income? Are you able to find financial support from friends, family and/or investors? Can you personally keep your business alive using your savings, home equity, and /or any other assets? Scary stuff, for sure! If that’s not really possible, signing a renewed lease (guessing it is for multiple years versus only one), then, perhaps it is not in your best interest, looking forward. In that case, moving on is likely best; I’m so sad to say that. However, Governor Brown is holding a special session next week and the reinstatement of the commercial eviction moratorium is one of the topics of discussion. Can you ask your property owner to give you another week before making a final, final decision about renewing? That may give you a little bit of breathing room in hopes of hearing good news from the State Legislature. I know those landlord conversations can be so anxiety prone but if you don’t ask, it definitely won’t happen!

Wishing you ALL the very best,


September 25, 2020

Dear Just Ask Joy,
I’m a local restaurant owner. We got the permit to be outside and while that’s good, our customers still aren’t coming. What am I doing wrong? 

Restaurant Owner Out of Options 

Dear ROO,

Thanks for your honesty! I really, really feel for you and your business. 

You may not be doing anything wrong! Sadly, yet unsurprisingly, most Portlanders aren’t feeling safe about dining out yet… and with cool, rainy weather upon us, we can assume that this attitude won’t improve anytime soon. 😬

First steps: Does your business use social media? And, do you use it often? Showcasing images of your awesome outdoor space and your Covid-19 safety measures are KEY. Images that demonstrate what your business actually looks like may really help to attract guests. If you’re not CONSTANTLY spotlighting your biz via social media, customers may assume that you have closed. Even one week is too long to step away from social media. It’s more crucial than ever to constantly share your hours and your revised business model/safety protocols with potential guests. Do you have tents, outdoor heaters, or umbrellas for guests? If so, showcase each and every rainy day element you’ve worked so hard to put in place!

Have you considered delivery options? Many foodies still have and want to spend money supporting their favorite food and beverage businesses. I know that the delivery app fees for small restaurants are staggering BUT, in looking to your business future, can you possibly review your budget forecast to consider those fees as a necessary path towards your long-range goals of staying open and relevant in 2021, 2022 and beyond? 

All the very best to you. Please keep me updated on your business!

September 18, 2020

Dear Joy,
I’m a business owner here in Portland.  Because of COVID, I applied for a street permit and now I’m open outside in one of the street plazas. Since my store is really small, we haven’t allowed customers in to shop.  I’m wondering if and when I should start holiday planning? With the rain and cold weather coming soon, I’m not sure how we could even do holiday sales. Help!

-Worried About the Holidays

Dear WAH,

Your question is a very, very timely one. Thanks for submitting it! I’m glad to hear that you were able to open for business on the street, but you’re right. With wintery weather on its way, selling on the street as your only platform for sales seems risky. Even worse, we don’t yet know whether those permits are going to expire in October as initially planned or whether they will be extended through December 31st. All of that means it’s important to explore your other options. Are you selling online? It is estimated that at least 66% of American shoppers are already anticipating holiday shopping EARLY and online. (They also say they plan on spending more money on holiday purchases than in previous years. Wow!) While customers report that they do miss the in-real-life browsing experience, customers expect to shop from home for the holidays. If you haven’t yet set up shop online, please check out our YouTube channel to see our ‘Snap and Sell-The Social Media Marketplace’ webinar from April 9, 2020. Check out our Small Business Podcast, too, where our first episode focused on the importance of using social media in the time of Covid-19.

My IRL small business recommendation is to (quickly!) meet up with your Business District Association and put together a “holiday hub” consisting of multiple shops. Having several shops in one location allows each of you to share resources and promote the holiday hub together (through group e-blasts, group press releases, and ALL of your group’s social media outlets) thus creating more buzz and more sales traffic. Perhaps there’s a large event space in your district—like a live music venue—that is being unused. This could serve as a safe shopping place for you and other business owners to showcase your wares this holiday season. As I mentioned earlier, shoppers want to start purchasing for the holidays NOW so using Halloween as your launch point may be a wise choice. Maximize the season by extending the holidays from mid-October all the way through the New Year!

August 28, 2020

Dear Joy,
I’ve noticed recently that several parts of the city have new murals and some have paintings, actually *on* the street. How can the business district that I volunteer with get in on this?

-Public Art Lover

Dear PAL,

Thanks for your question. I too am a big fan of the colorful explosion of art around PDX! 

Several business district associations have artists in their existing networks so they were able to call upon them for help. Some of those artists even brought their own supplies and donated their time. Our local artists are amazing! (You might check out @shopidlehandspdx on Instagram to see the Foster Area murals and artists’ info.) 

If you’re not lucky enough to know an artist eager to donate their time, a public mural can cost several thousand dollars, but don’t worry! There are funds to be had. It just so happens that our own fall grants cycle just opened and it includes dollars for public art. Check it out.

Now, it’s 🥳permit time🥳. Wait, don’t go! Bureaucratically speaking, murals are actually pretty quick and painless. You can either file for a $50 permit directly from the city, or apply through the Regional Arts & Culture Council (RACC) Public Art Murals Program, (which can unlock more grant dollars for your mural).

As for the art that is literally painted on the roads, much of it is through PBOT’s “Safe Streets/Healthy Business Permit” that allows businesses to use parts of the street. For those who get a healthy business permit, Miller Paint offers up to 30% off on paint for the street project. For BIPOC-owned businesses, I’ve heard that the paint is offered at no-cost. Residential areas can also do street painting projects, but that’s a slightly different program that doesn’t really apply to commercial corridors.

Thanks to you, PAL, for the timely question!