Losing My Job Motivated Me To Build The Top Travel Newsletter On Substack [$20K/Month]

Yolanda Edwards

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Published: June 17th, 2022

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About
Business

Yolanda Edwards

Founder, Yolo Intel

$20K

revenue/mo

Founders

Employees

Yolo Intel

yolojournal.substack.com

from Brooklyn

started February 2019

$20,000

revenue/mo

Founders

Employees

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Hello! Who are you and what business did you start?

Hi guys! I’m Yolanda Edwards, the founder of Yolo Journal, which is a travel lifestyle media brand I launched three years ago. I’ve been in the magazine business for 25 years–mostly at Conde Nast with a brief stint at Martha Stewart–and when I lost my job, I decided I wanted to create a magazine concept that I thought was missing in the market. In 2019 I came out with my first issue of Yolo Journal, and now I regularly create a physical printed magazine 3x a year.

Last June, after being hounded by friends and followers, I launched a weekly newsletter called Yolo Intel, and it has become the most successful travel newsletter on Substack. All of my readers/followers are travel-obsessed and want to have the best lists for what/where/how–most of them find me through social media, and then convert over to the newsletter, magazine, or both.

Today I’m making 20k a month just from my newsletter!

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

I’ve always been travel obsessed–from a young age, I would save any travel article, and create files based on location–if someday I might be going there and might need that intel. Nevermind that I was 11, living in Tacoma Washington, and had never been anywhere besides Yosemite or a no-name lake in Canada–I had files on Paris, New York, and Rome.

If you see a hole in the market, and it’s something you’re deeply passionate about, you should try doing it.

In my early 20s I landed a job in the photo department at Conde Nast Traveler–and back in those days–the 90s–photographers didn’t have websites, so they had to physically send their portfolios to our office for us to review them. Often they would just bring them and hope to get a meeting with my boss, the photo director–who never wanted to meet anyone she wasn’t already working with.

I ended up being the person who would talk with them, looking at their work, asking them questions about where the photos were taken, what they loved about the place, etc. And I learned that these creative people who were actually out in the world were far more informed and interesting than the actual writers who were being assigned by our magazine to go out and get the stories.

I always thought that was so strange–that we were spending so much money to create stories when there were stories that were already existing–that we just needed to unearth. It took 20+ years for me to be kicked out of the corporate nest and explore this idea, which is the essence of what I’m doing with Yolo Journal, the magazine. And the newsletter, while very much based on my travels, also has so much of its content coming from really interesting and creative people I have met–and asking them for their favorites around the world.

I had a feeling that this was the kind of information that would resonate with an audience–for years I had been getting texts, emails, and direct messages, asking me for this kind of insider information–clearly nobody was serving this up.

Take us through the process of creating the first issue of Yolo Journal.

For my first issue of Yolo Journal, I spent a ton of time emailing, calling, and taking photographers, stylists, and well-traveled friends out for coffee.

I was on a listening tour, as well as amassing great information from everyone I met. Every single person said the same thing– ”there isn’t a publication that is giving me the kind of travel information I want–I don’t want to know about what’s new, I want to know about what is good.” …And, “I get better and more trustworthy information from Instagram than I do from magazines”. I knew I was onto something.

A dear friend of mine with a legendary hotel in Italy, the Pellicano, kept saying she wanted a Yolo magazine–her nickname for me–and that just stuck. Once I decided to do it officially, the same friend said she wanted the magazine to premiere at the opening of her next hotel, the Mezzatorre, where there would be a ton of pr/social media types. It was having that deadline that made me get it done. I hounded every photographer friend I had to send me their images–thank god for Dropbox and WeTransfer–and then I brought in a former colleague, Nobi Kashiwagi, who was working at Vogue, to design it.

I told him that he could design the type-faces, a dream for him–and I knew that it would be much more of a creative outlet for him, so he agreed to do it as a side hustle and for a fraction of what he should have made. All the photographers gave me their images–they too were just excited to have someone give them a platform for their photography–they knew I would treat their images with respect and not put junky type all over them. Further, the idea was to make the stories be also in their voices–but as most weren’t writers, I just interviewed, recorded, and transcribed them.

As for bringing the product to market, I had to find a printer who would do the distribution. My husband had just printed his first magazine several months prior–a men’s lifestyle magazine called Wm Brown, and the distribution was a NIGHTMARE. We were so clueless–we got the magazines delivered to our house, put up on his Instagram that the magazines were here–we took the orders via our Squarespace account–but we physically packaged up and made the labels and mailed them out ourselves–all of this in December right before the holidays–so you can imagine the post office drama. I told my husband there would be no issue 2 if we didn’t sort this out, so I started talking to everyone who knew anyone in the printing world, and we finally found a printer who would handle the distribution directly from their plant. We’re still with them, even if there are hiccups with printing here and there with quality control–but that would happen with anyone.

Next up I had to find stores that would want to carry Yolo! I made lists of all of my favorites, and then I got ideas for shops by looking at the stockist lists from brands that I loved. I wanted Yolo to be in stores that were a bit more on the highly curated side of things, which may be the least expensive item in their store. Once Yolo came out, so many cool shops just came to me and wanted to carry it. We’re also in some of the best hotels, seatbacks of Aero the private-ish jet company, and in Swiss Air lounges.

Describe the process of launching the business.

I launched the magazine at the Mezzatorre hotel opening, and it was a huge success. The guests were a big international group, most in the fashion business–the magazine was in all of their rooms, and on tables around the hotel. Because the cover was such a beautiful image from the Pellicano, photographed by Stephen Ringer, of his wife, Aly Michalka sitting on the dock–and there were no cover lines–it was so photogenic that everyone was taking photos of it. That brought a huge awareness to it. Other dear friends who are designers and wrote about their favorite place in Italy for that issue, brought a box of magazines to Paris market week, and all of these interesting store owners from around the world were exposed to it and ordered the magazine.

There was a lot we did wrong–terrible website (still is–it is pretty much a landing page that you can order from, and see who carries us, and press) which wasn’t a seamless experience. And initially, we had our printer sending out magazines to anyone who ordered from anywhere in the world. However, they didn’t have tracking, and while the shipping was cheap ($8 anywhere in the world), it was a crap shoot if you lived in Singapore and had ordered it. I ended up communicating via IG that we weren’t fulfilling any more orders outside the US, and anyone who wanted the magazine outside this country was going to have to order from our stockists. Now we have a distributor in the UK, so that is helpful. And we just recently moved our basement distribution to a proper Ship Monk distributor. I still send out notes and trinkets to our founding members of our newsletter community, but we aren’t a shipping center anymore.

As for how we financed our first issues–I took on a pretty time-consuming consulting job just so I wouldn’t have to be financially stressed. I didn’t want to make the magazine so dependent on advertising–I had seen where that went with Conde Nast–I didn’t want to end up creating content because an advertiser required it. So I had no ads and only made money from people buying the magazine. If I paid myself, I would have lost money, but since I only paid out my art director, copy editor, and the printer–I didn’t have huge expenses and broke even. I never thought the magazine was going to be a profit leader anyway–I saw it as the calling card–the shop window. One of my favorite stories for how we justified spending the money to launch the magazine (I didn’t have a full-time job anymore, so we also now had to pay for health insurance–a new expense for us)--one night in the middle of the night, there was a huge crashing sound just outside our house. A huge London Plane tree had fallen and crashed right on top of our car, totaling it. It turned out with the way the insurance worked, and our getting a new lease, that we got a big check from the insurance company, and that financed the magazine.

I’d say the biggest lessons I learned are about distribution. I never understood what that meant when people spoke about the distribution model. Now I get it! So, figuring that out, for everything, is the most important thing. But there is also some real magic that happens from being naive. There is no way I would have launched Yolo if I knew all the headaches that I’d go through to do it–but I wouldn’t have it any other way. It’s like childbirth!

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

The magazine, newsletter, and social all attract completely different audiences. On social, I have 95K followers on the @yolojournal account, and that has grown so much because we do Story takeovers with different travelers from our community, who share their trips with us by creating a whole narrative and tagging us, and we repost. Their audience is exposed to us, and the traveler is exposed to ours. It's a win-win way to grow our travel community.

The newsletter is very much a word of mouth growth–although I did do a Ask Me Anything hotline on my friend Jenny Rosenstrach’s Substack account, Dinner a Love Story, and got several thousand new subscribers in an afternoon.

The magazine is a very specific consumer: they want to have a beautiful object that they keep (like a book), and it is something they reference, but it is more about having a thing of beauty and high curation.

There is a crossover between all of the platforms, but I would say I’m surprised how many different Yolo consumers don’t know about the other platforms.

As for customer retention, I just try to make great content and overdeliver. I don’t do any hard sell, and I never advertise. My husband and I both do events that are always free and open to the public and usually have some great drink component, like Negronis or some lovely wine. I love doing that because I want to bring the community together. Just the other night I ran into someone who came to a magazine event I did at a store out in San Francisco, and he became best friends with a woman who also attended the event. That is what success looks like to me–bringing together like-minded people, and creating a community. It may not mean anything in the short term profitability, but it makes me happy, and everyone who comes happy, and I think it authentically builds the brand. I’m in this for the long haul!

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

Since launching the newsletter almost a year ago in June 2021, I’ve been able to see this as a real business. In the first couple of months Substack, the platform I use for my newsletter didn’t have a paywall element as a part of their offerings to creators. This meant to grow the audience, I needed to create free content, as well as content that was for paying subscribers. I wrote two separate newsletters each week for at least three months, and it was A LOT. Once the paywall option was available, it freed me up to do the free newsletters with a little less frequency–sometimes just 2-3 times a month–because the reader could still have weekly content from me, but understood that there was a difference between free and premium. When there wasn’t a paywall, the free reader didn’t even know that there was a whole other level of premium content, so there wasn’t any reason for them to convert over to being paid subscribers. I am very allergic to selling–I believe in spending my time doing what I love–creating great content–and letting it speak for itself. I do tease out the content on Instagram and that has a very big conversion rate, and I also grow my audience by doing interviews–like this! As for other revenue streams, I do create some product collaborations, like a travel slipper shoe I created with Scarosso, and a Yolo tote bag I created with Parker Thatch. I also do some partnerships with brands like Sotheby’s, Matches Fashion, and Loro Piana, where I create content for them that then lives on their site, and I promote it on my Instagram.

I hired a deputy editor in the fall, and am bringing on our first full-time editorial assistant this summer. Now that I’m able to staff up a bit, I’m able to think a little bit bigger, about where we want to go in the second half of 2022.

I want to have a family travel section within our newsletter, as that is a market that needs more advice than anyone, and is very underserved. I’ve dabbled in collaborations with different brands in the past, but just launched a capsule collection of Italian shoes that I’m excited about. I’m planning for several others later this year.

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

I grew up with a mom who was always very cautious with money–she had the thickest coupon book and I cringed every time we were at the grocery checkout. But I learned a lot from her, and I always tried to save money back when I was working on photo shoots.

This didn’t make me very popular at the office, because the culture was very much one of “if you don’t spend it, we won’t get the same budget next year”. Then as things started to fall apart at our company, all of a sudden my thriftiness became very popular. I was able to bring the cost down of a single issue of Brides from 180k to 25k.

It was all about knowing how to find the person who wanted to share their assets on our platform–of course, the assets had to be beautiful, and it had to be a very strong editorial pov–but there were so many out there and we were able to give them a platform and get their assets for free.

When it came to doing my own business, I did exactly that–I analyzed where I could find assets that were excellent and not exposed, and went after them. I knew there was an audience for it. I knew where to find the assets because I was always friendly to the photographers ever since I started–so I had a big friend base. I always tell anyone I am training to always be kind. Not only does it make working more fun, you never know who you’re talking to, and where they will end up.

What platform/tools do you use for your business?

My favorite tools are Instagram and Substack. I am not a fan of Squarespace at all, although I haven’t quit them yet. They are like my dysfunctional boyfriend–I just don’t have time to get out there, find a new one, and put the time into him. It’s super clunky and the customer experience is terrible. If someone wants to change their address they pretty much have to close their account and open a new one.

Switching to Shopify is a goal for this year–and having a new FT employee will help me make that happen. As for Instagram–I’m able to monetize that with influencer engagements, and I’m able to grow my community.

Substack was so easy for me to create the newsletter–I never would have been able to figure out how to do that on my own. I’m a content creator–not good at all the tech side of things at all.

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

I wish I had time to read and listen to podcasts. I work all the time–especially because I travel so much–every minute I’m not in travel mode, I’m working.

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

If you see a hole in the market, and it’s something you’re deeply passionate about, you should try doing it.

Don’t tell anyone who is family/friends and deeply skeptical, because you need all the positivity and encouragement.

Of course, you don’t want to be naive, but I find that many of my dear friends who are super well-intended always tell me to do the safe thing–and that has never been the right thing.

Are you looking to hire for certain positions right now?

I don’t think I’m hiring right now, but if someone out there is reading this and has a brilliant idea for how I can do better, please, let me know!

Where can we go to learn more?

Website:

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