Thanks, Matt—that really means a lot!

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

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.

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.

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.

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) 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!

Thank you, James—really appreciate it!

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. :)

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.

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.

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.