Longform Writing

Over my time running Sifter, I spent a lot of time trying out different marketing tactics. Then, working on Postmark, we tried quite a few additional tactics as well. The FOMO was always overwhelming. Retargeting. Banner ads. Blogging. A/B testing….

About 11 years ago, I quit my job to start Sifter. Today, after my knowledge of running it for 8 years, I would have been too hesitant to start it. It’s not that I would be afraid, but I’d overthink it. I’d be at a standstill over-analyzing every single…

The pursuit of perfection is a ruthlessly efficient killer of ideas. Whether fear that we don’t have the ability to make something “perfect enough” or the temptation to endlessly refine something because of some arbitrary feeling that it’s “not ready,”…

Years ago, I shared some blog posts about half-baked ideas for a bug tracker. I wasn’t planning on trying to build a business. I wasn’t even sure if I was going actually write any code. I just wanted to explore some interface ideas.

When you spend eight straight years designing, developing, and supporting a product by yourself, you gain perspective. You truly feel the consequences of your decisions as they ripple through the years. When you work on a team and are able to…

The internet is an awesome thing, but we’re ruining it. We probably can’t get enough people to stop shipping bloated and broken software, turn off their obtrusive newsletter sign up modals, or stop writing fake reviews for free products, but maybe the…

When it comes to sharing ideas that involve visual elements, source code, and unifying concepts that span disciplines, the friction to include different types of media and information makes technical writing rather tedious, and streamlining that process a bit has helped make it more enjoyable to write.

Some time ago, I removed all the tracking from my personal site, and I haven’t missed it. What started as a whimsical idea that was part performance-based, part referrer spam overload, and part backlash against Google evolved into a realization that…

DMARC can be a bit intimidating if you’re not familiar with it, but with some planning and easing into it, you can safely setup an initial DMARC policy to monitor your domain’s email activity and steadily progress towards blocking all unapproved senders without hurting your legitimate email delivery.

With software development, there’s a spectrum out there with stability on one end and speed on the other. You can have an ultra-stable system that progresses incredibly slowly, or you can iterate blindingly fast on a system that’s a mess. Skip…

If you make a living at your computer, there’s a good chance, it makes sense to invest in that space to maximize your ability to focus and do creative work. Here’s some ideas that helped me.

After four months of being back on the independent consulting train, I can confidently say that hourly billing haunts me. It puts a quantifiable dollar amount on time. For things like mowing the lawn, that makes the decision easier. If it costs less to…

Progress isn’t easy or comfortable. When there’s an idea in your head, and you want to get it out into the world, it’s easy to focus on the bits you haven’t finished. And it can haunt you. With so many decisions to make, how do you prioritize? Maybe…

My only regret about amputation is that I didn’t do it sooner–and I’m not alone in that experience. I don’t want to glorify amputation by any means, but I get enough emails from people asking about regret that it’s worth talking about regrets–or rather…

When I sold Sifter, I regularly wondered if I’d ever be able to find the time to build another business or application now that I had a family and different responsibilities. Here’s how I’m figuring it out.

At the beginning of May, I’ll be leaving Wildbit to create some space and flexibility to work more on Adaptable. In the meantime I’m actively looking for opportunities that will help pay the bills and give me a way to do work that aligns with my hopes…

So much has changed in my 10 years since starting Sifter. My personal life has changed significantly, and technology has evolved just as much. I’ve done my best to keep up with the changing ecosystem, and after more than ten years of SaaS experience,…

A little less than a year ago, I started thinking about a project to help amputees become more active. The initial vision involved a web application. That meant development time. Hosting. Backups. And all of the other services necessary to build and…

In our incessant rush to move quickly, everything is ephemeral. Technology moves so quickly that today’s strong favorite is outdated in a matter of years. We slurp up notifications and are fascinated by the next thing before we even fully understand the…

There’s a big difference between creating software and shipping it. Creating is easy. Shipping is the hard part, and countless companies never quite figure it out. Sure, they might release their software, but that’s not the same as shipping. No company…