Venture Capitalist at Theory

About / Categories / Subscribe / Twitter

5 minute read / Apr 3, 2013 /

What I’ve Learned about Blogging in 3 Years

I have been writing for three years now and it’s been a ton of fun. I hope to continue to write for many more. Along the way so far, I’ve learned a few lessons on frequency, content type, idea generation, voice, titles and distribution.


There are two schools of thought on blogging frequency: high frequency vs high quality. At this point, it’s unclear to me which is better for building an audience because both work. Each camp has its exemplars of success.

In the frequency camp, Fred Wilson posts every day and I suspect this is because when he started seven years ago it was essential to write daily to train an audience to visit Today social media (twitter, hacker news) generates most of the traffic for a blog by bubbling up the best content. Building a core audience that visits every day is important to me, but I post every day because each writing book I’ve read recommends it. And I figure if I’m writing a blog post, I may as well publish it.

I write sometime between 5 and 7am each morning when it’s quiet and I can focus. Flights are also good times for blogging.

Representing the other point of view, Chris Dixon and Paul Graham pen monthly essays and posts which are better revised and often succinct, witty and always very well written. This technique concentrates engagement, maximizes social media reach and ensures great content.

Content Type

I never can predict with much accuracy which content will resonate with readers who tend to be startup founders and employees. But the most successful posts tend either to create an emotional connection through a personal story or share some detailed tactical advice. The best posts enable readers to see a reflection of themselves in the story because they have or are living through something similar.

Reading and dissecting classic novels and well written magazine articles helped me begin to understand how other authors do this well. Burt Helm from Inc magazine shared this GQ article about Suicide Catchers in China as a great example of storytelling.

One example of a successful emotional/storytelling post is “The Biggest Challenge of My Professional Career: Communication”

And “Your Startup’s 10 Most Important Metrics” is example of a very tactical post that readers enjoyed.


Writing every day demands lots of ideas. I jot down notes during conversations, sift through my calendar, read the news, and examine what’s trending on social media. Sometimes, I don’t have any ideas and to jog a stream I search for a strong opinion or reaction I’ve had recently. That seems to help breaking my writer’s block.

I keep a list of these ideas in draft blog posts. Sometimes I just jot down a title and other times it’s a jumble of ideas. Then I’ll go back the next day or in a few days to complete the content and edit the post. At any given time, I’m working on 3 or 4 drafts. I might hold onto a draft/idea for a month or two to let it mature a bit so I can better express it or gather examples.

After a few weeks of practicing, storing and retaining ideas becomes part of a daily routine. Nevertheless, some days, I feel like I’m wading through mud to write a few paragraphs.


Blog readers respond to strong individual voices. A blog shouldn’t resemble the Economist or the New Yorker whose editorial teams use style guides to ensure a consistent tone which is larger than any individual writer. The whole point of a blog is to hear a real human voice. It’s something I forget sometimes so I try to write the first draft the way I might speak and edit that output. Hemingway is my inspiration for human tone.


Titles matter. I spend lots of time on my titles but I didn’t always which was a big mistake. Looking back through the first year or so of my blog titles, I can see now they were awful. Here’s an early one: “Binary pointillism - the intersection of Seurat and Felton.” Barf. Who wants to read that? It sounds like a dissertation.

Dan Shipper taught me the best titles read like tweets. My goal is to drive as many retweets as possible so I shouldn’t ask the user to construct an interesting tweet on my behalf. Instead, I should make it easy for the reader to just hit a button and share something interesting.

I often write the title as the last step. It’s easier after having written the conclusion to summarize the point in 140 characters or fewer.


Once I post, I tweet the post, submit the post to Quibb and Hacker News. Then I monitor the reactions. If after 45 minutes, I don’t see many retweets or much engagement, I’ll try another title or two. Sometimes the post is to blame, but more often, I haven’t allured the reader with the right title.

One blogger recommended ignoring the Google Analytics and Feedburner stats to me. I find that it helps quite a bit not to be so metrics focused. Then I’m not so concerned about the daily fluctuations but more on monthly stats, which is a better indicator of success. Nevertheless, I still haven’t figured out how best way to measure the success of this blog.


Honestly, it takes forever to build a blog that people know or read about or care about. For some, the reader base grows much much quicker than it did for me. Nevertheless building any kind of brand on the web through content or otherwise is a slow, incremental process. Every once in a while, I’ll reach the front page of Hacker News or spike on LinkedIn and I get an increase in readership. But it takes patience.

I find the more content I have produced, the more the blog pays dividends. Most of my posts are evergreen, timeless, so they appear in Google searches or are randomly resurrected in social media from time to time, rediscovered through some stroke of luck.

Ultimately, blogging helps me refine my thinking and share it with people who are interested or curious. I hope this post helps motivate you to write.

h/t to Stefano Bernardi @stefanobernardi, who inspired this post.

Read More:

Breaking Down a Typical VC/Startup Diligence Process