Tracy Osborn

is an outdoorsy designer, developer, author, and entreprenerd living in Toronto, Ontario.

Recent Writing

  • Two companies that I appreciate

    Two recent experiences with two companies lately made me realize that I often forget something more important — that I should write about my positive experiences. It's so easy to complain about the negative but harder to realize and appreciate ...

  • Five tips for improving your technical writing and documentation.

    Get more users and fewer support requests by leveling up your writing and technical documentation.

  • Case Study: Hello Web App

    In 2011, I taught myself how to code Python and Django to launch my startup, WeddingLovely. I got something working, but over the years of working with Python and Django, I became more and more frustrated about how programming in ...

  • Case Study: WeddingLovely

    I'm moving to Toronto and looking for a job (!) and thought I'd deep dive into my two main projects to showcase my work. WeddingLovely is an online wedding vendor marketplace and wedding planning application, started in January 2011 by ...

  • Moving to Toronto + Looking for New Opportunities

    After six (!) years of working full-time on WeddingLovely in California, my husband and I are moving to Toronto and I'm exploring the possibilities of working on something new. I've been so lucky to work for myself for so long. ...

  • My 2015 reviewed

    Funny how you can sit down on December 31st and feel like you did nothing the whole year... and yet it was the busiest one yet.

  • How I run a bootstrapped marketplace with eleven different properties and 5,000 vendors — by myself.

    I launched WeddingLovely, my startup, nearly five years ago. WeddingLovely, in a nutshell, is a free online wedding planning guide and wedding vendor marketplace. My goal is to walk couples through their wedding planning in a simple and sane way, ...

  • What I Wish I Did Differently: Self-Promotion

    A little different than self-deprecation (downplaying achievements), I'm also terrible at self-promotion (even mentioning what I'm doing and excited about.) I'm running into that now with Hello Web App, the book I'm working on (woo, self promotion!) Ideally, I would ...

  • What I Wish I Did Differently: Self-Deprecation

    The focus of this post is a little funny since these last few posts have been quite an exercise in self-deprecation and not being positive — going over my perceived failures and things I wish I could change. In hindsight, ...

  • What I Wish I Did Differently: Networking

    I launched my startup a little over four years ago, and as always, when looking back, it’s easy to pick out my mistakes. Hindsight is 20/20. But it’s also valuable to make note of places that I wish I did ...

  • What I Wish I Did Differently: Blogging

    Some of the biggest wins in my life have been tied to blogging and writing down my experiences. For a long time, I known as the “Hacker News wedding person” after my articles about trying to find a cofounder and ...

  • Creative Storytelling: The Most Dangerous Thing I've Ever Done

    I wrote about my experience hiking the John Muir Trail solo last summer (200+ miles) and getting myself into the most dangerous situation I've ever been in.

  • I'm a Designer Who Learned Django and Launched her First Webapp in 6 Weeks

    Hi — I'm Tracy. I'm a designer and front-end developer. After being turned down by Y Combinator, I decided to launch a simple webapp to get myself on the path of development.

  • Building Beautiful Business Cards

    Cards from are a great place to start to get nicely printed cards on thick, professional stock. You can order them with your information printed, but blank cards are a great jumping off point to create interesting and handmade ...

  • Keeping inspired at the right times

    Age old problem: When I am at work, and admittedly immersing myself in design blogs, top CSS sites, and other creative resources to keep the data part of my job interesting, I get inspired. I get really inspired. Heart rate ...

  • Speaking at Silicon Valley Geek Dinner

    Hey, it's my very first speaking engagement! Sadly, I'm not talking about anything REALLY awesome; I'll be expanding a bit on multivariate testing, the stuff I do at work and how it has worked for the sites I manage. I ...

Upcoming Speaking Engagements

  • 6/27/16

    GitHub CodeConf

    Los Angeles, CA
  • 7/16/16


    New York City, NY
  • 7/17/16

    DjangoCon US

    Philadelphia, PA
  • 8/18/16


    Pittsburgh, PA