AMA: Jeremiah Shoaf, Creator of Typewolf

almost 6 years ago from , Designer at Jeremiah Shoaf Design LLC

Hey everyone! I’m Jeremiah Shoaf, a freelance designer who works on lots of side projects, with the most notable being Typewolf.

Typewolf showcases web fonts in the wild and features curated font lists like my collection of Google Fonts. The site has gotten fairly popular over the last several years with over 250,000 unique visitors a month. I do everything on Typewolf—design, development, curation, writing, etc.

I’ve also been freelancing full-time since 2007 and have worked with clients like Discovery Channel, Pepsi, Sharp and The Washington Post.

I live in Colorado with my wife, 6 month old daughter and hyperactive yellow lab.

Feel free to ask me anything about Typewolf, Google Fonts, running side projects, freelancing, being a first-time father or anything else!

I’ll start answering questions at 10:00am EST on Wednesday, July 20 and will be checking in throughout the day.


  • Matt BaxterMatt Baxter, almost 6 years ago

    I wish I had a good question to ask, but I'll just say that Typewolf is my favorite site about typography. Thanks for the great resource!

    9 points
  • Sacha GreifSacha Greif, almost 6 years ago

    Do you monetize Typewolf? If yes, how and (approximately) how effectively? If not, is that something you're considering?

    3 points
    • Andy LeverenzAndy Leverenz, almost 6 years ago

      I'd like to know this too. Sacha you read my mind!

      0 points
    • Jeremiah Shoaf, almost 6 years ago

      I do indeed monetize the site but not super aggressively. I earn a small affiliate commission when I link to fonts on MyFonts and Fontspring. It’s not much but it helps support the site.

      I also sell two $39 guides—The Definitive Guide to Free Fonts and Typewolf’s Guide to Typekit. The guides earn much more than the affiliate links.

      I don’t make enough for a full-time living but I make enough to want to continue working on the site. I’m actually currently working on a new product that I’m planning on launching sometime in the next several months. I’m hoping that will turn Typewolf more into a real sustainable business than a side project.

      2 points
  • Andy StoneAndy Stone, almost 6 years ago

    Thanks for being the coolest! Crap, that's not a question. Okay, here's some questions:

    1. How did you get the first people to hear about Typewolf? I tell everyone I know, but how did the first 100-500 people hear about it?
    2. Do you think there will there ever be a condensed all-caps serif trend like there was with condensed all-caps sans?
    2 points
    • Jeremiah Shoaf, almost 6 years ago

      1) When I first launched Typewolf in 2013 I literally just emailed everyone I could think of saying “check out this new project I just launched”. From there, the site got featured in a few newsletters like Webdesigner Depot and maybe Smashing Magazine (can’t remember exactly). That gave it some nice initial traction. I would like to say after that the site spiraled in popularity but really it just died down after it was no longer the hot new thing. At that point it was just months and months of grinding things out with not many people knowing about the site until it slowly started to grow again.

      I see that happen a lot with side projects. They get that initial buzz because everyone likes to talk about what is new and fresh, but then things die down pretty quickly and the creator gets bored with it and gives up. I think the key is just to keep grinding it out if you really believe in your project.

      2) This is a trend I would love to see. Wired are doing that using Ambroise (which is available on Typekit but not many people know about it). We see that so much with condensed American Gothics and DIN Condensed that I think a serif trend would feel really fresh.

      0 points
  • Yitong ZhangYitong Zhang, almost 6 years ago

    Hi Jeremiah. Thanks for doing this. I've been using Typewolf for a while now and it's really helped me develop an eye for type. I have 2 questions for you:

    1. What is your process for picking a font system for a project?
    2. What are some things design students can do to improve at typography?
    2 points
    • Jeremiah Shoaf, almost 6 years ago

      1) I always start with the body text font first. If it will be a text-heavy project you will need a typeface with normal, italic, bold and bold italic styles, a large x-height, open apertures and low stroke contrast. That narrows the choices down quite a bit.

      From there I will usually look for a display face from the same family if it exists. So on my Typewolf redesign, Domaine Text + Domaine Display was an easy choice. Otherwise this is a rough system I like to use for pairings:

      • Geometric sans-serifs + Modern (rational) serifs
      • Grotesques and gothics + Transitional serifs
      • Neo-grotesques + humanist slab serifs
      • Humanist sans-serifs + Old Style (humanist) serifs
      • Neo-humanist sans-serifs + contemporary serifs

      2) Read The Elements of Typographic Style by Robert Bringhurst if you haven’t read it already. And then pay attention to all the typography you see around you and when you see something you like, try to analyze it and discover what about it makes you like it.

      3 points
  • Alec LomasAlec Lomas, almost 6 years ago

    Hey Jeremiah! Love Typewolf (one of my favorite emails to get every month!).

    What are your thoughts on the recent trend of using the default system fonts on web pages? E.g., San Francisco on macOS/iOS, Roboto on Android/chromeOS, etc.

    0 points
    • Jeremiah Shoaf, almost 6 years ago

      I think system fonts can be a good idea in cases where site speed/performance is of utmost importance. San Francisco and Roboto are definitely a step up from Arial and Georgia.

      But from a branding perspective I think they will appear generic and pretty soon just feel like default options. So it’s a tradeoff between creating a strong brand that makes an emotional impression vs pure site speed.

      My prediction is that it will become trendy for awhile and then people will get sick of it after seeing every site using San Francisco. :)

      1 point
  • Mathieu Triay, almost 6 years ago

    Hi Jeremiah! Always love checking Typewolf for typographic niceness, excellent work. I have no formal training in design, but I really dig typography (I did pretty much what you recommend, read Elements of Typographic Style and then analyse every little bit of nice type I can see).

    As a result: 1) How do you overcome the problem of typefaces that would fit what you want perfectly but have been overused or used by big brands/companies? 2) What do you think is the most sustainable model for selling web fonts? (I like buying outright, self host and use as much as I want for a certain number of views per month overall). 3) Have you ever thought about making your own typeface? If so, when you have the letter shapes, how do you work out the spacing (first sidebearings and then kerning)? Scouring the internet, there doesn't seem to be a good starting rule of thumb for this...

    0 points
    • Jeremiah Shoaf, almost 6 years ago

      1) If the typeface is perfect for your project then I wouldn’t worry too much about the typeface being too popular overall as long as it isn’t overused within your target market. Sometimes things feel really overplayed to designers but will feel new and fresh to your target audience.

      If it’s a typeface that is really used everywhere then it may be worth looking into different typefaces that share a similar aesthetic. I did a blog post about the 10 most popular fonts of the year where I listed four alternatives to each typeface that isn’t as overused. That could be a good place to start.

      You could also just use the overused typeface in a new or different way. Maybe use a different weight or style or do stuff with color to make it stand out.

      2) I prefer buying as well rather than renting through a service. I’ve heard type designers don’t make much through services like Typekit unless the font is super popular. If I were a type designer, I would just focus on doing really amazing work and then selling at a higher price point more as a luxury item. Trying to compete on price is difficult as there are so many free fonts available now. There is an “exclusivity” factor and I think people will pay money for that, especially for a really high quality product.

      3) The more I learn about type, the more complex typeface design seems. I feel like it would take years and years of study and practice to create something I would be proud of. So I really don’t have any desire to go down that route.

      As far as sidebearings vs kerning, I would check out the TypeDrawers forum. That is where all the type designers hang out and they have lots of posts on the technicalities of typeface design.

      Hope that helps!

      1 point
      • Mathieu Triay, almost 6 years ago

        Thanks for the in-depth answers!

        1) Very good point to keep in mind, thanks! Your blog post is interesting because I suppose it reflects one aspect of my worries: there's a flourish of friendlier geo sans serif (Circular, Brown) that echo more classic designs like Futura/Avenir and I feel it's hard to go with another face just for the sake of being different and looking like you're "trying to be X" or been "inspired by X".

        2) I find that the fonts under the https://vllg.com banner (inc Domaine by Klim) have a very approachable licensing system (and pricing too). Still, I love Typekit and I wish the website had a makeover like Google Fonts because it doesn't feel fully adapted to the breadth of their catalogue anymore.

        3) Thanks! I'll check that out. I've draw 52 basic glyphs but I must say the next steps make me think the same thing: practice, practice, practice!

        0 points
  • James K., almost 6 years ago

    Thank you so much for doing this for design community, Jeremiah! I have been following up your every Tweets @typewolf and learning a lot of information in screen/online typography. One of significant typography resource in design community.

    0 points
  • Max LindMax Lind, almost 6 years ago

    Hey Jeremiah! - thanks for joining us.

    • What does the backend of Typewolf look like?...and what tools/services do you use to help you day to day?
    • Seems like every freelancer has a couple of their own tips/tricks re: work/life balance... what are yours?
    • What's the coolest and/or most random thing on the internet you keep coming back to as of late? (could be a website, tool, service, etc)
    0 points
    • Jeremiah Shoaf, almost 6 years ago

      Thanks for having me, Max!

      1) Typewolf runs on Statamic which is a flat-file CMS that I am absolutely in love with. It’s super simple yet has enough features to run pretty complex sites. The absence of a database and heavy use of caching helps Typewolf load quickly.

      The front-end was built with Zurb Foundation 6.

      My favorite tool is probably WorkFlowy. I use it to manage all my projects and to-do items. It just gels really well with the way my mind works.

      2) I block off 4 hours every morning to work on my most important task of the day. No email or social media, just focused work. I use SelfControl to block any distracting sites like Reddit. After that, I am kind of done for the day. I’ll work on email and misc tasks but that will be interspersed between walking the dog, taking care of the baby and other family stuff. As long as I get the 4 hours in, I stay pretty productive despite what happens the rest of the day.

      3) Slither.io—this game is strangely addicting. I have to block it during my focused work period. :)

      1 point
  • Nathan LongNathan Long, almost 6 years ago

    Love your site! How do you find all these sites for your 'Site of the Day'? Do you have a process? (There's usually a large number of well designed sites I haven't seen referenced anywhere else!)

    0 points
    • Jeremiah Shoaf, almost 6 years ago

      I spend a ton of time on site selection, so glad you noticed it. :) I have probably a dozen or so gallery sites I regularly visit, with my favorites being siteInspire and httpster, but I try look beyond some of the obvious sources. I follow a lot of agencies I admire to see when they launch new work.

      Probably half the sites I feature come from email submissions. I have a nice network of designer pals that send me not only new sites they launch but other sites they stumble across from surfing the web. Those tend to be the best/most unique submissions.

      2 points
  • Christopher Reath, almost 6 years ago

    Hey Jeremiah. Love the work you do. It's been a great resource for so many designers that I know.

    What is your favorite web type trend that has occurred within the last 5-8 years?

    0 points
    • Jeremiah Shoaf, almost 6 years ago

      The explosion of web fonts would be an easy answer but I would have to go with super large type as a design element. I love seeing the details of a typeface when it is set at 100px+. Obviously it’s possible to go overboard with that but when done tastefully I really dig it.

      0 points
  • Duke CavinskiDuke Cavinski, almost 6 years ago

    Hi Jeremiah. Love the site, and hope it continues.

    I've been following your selections for a year or so, and have begun noticing a gradual trend of continued simplification, simple grids, bold background colors and (obviously) type-centric design. How do you feel about the state of web design as it stands today versus say, a few years ago? And do you have any indication of where it could or should go from here?


    0 points
    • Jeremiah Shoaf, almost 6 years ago

      I’m really digging the new minimal, type-centric approach that we’ve been seeing lately. The “Bootstrap look” where there is a huge hero photo with white text on top of it seems to be dying out in favor of a more renewed focus on solid color.

      More and more designers are realizing you can still have readable type without using black (or gray) text on a pure white background. The Oak site is a good example of this—lots of color but still very readable. Everything is becoming so templatized that type + color is one of the few remaining ways to really differentiate your brand and make an impression.

      I think this is what we’ll hopefully see more of in the future.

      0 points