Articles marked historical record the period of starting HelpSpot in 2005 through 2019. In 2020 I decided to give the blog a fresh start, but have left these here for posterity.

July 5, 2019

The best credit cards for greedy software founders

This article is about greed. Greed in maximizing the rewards we get by the fact that as software founders, we pay for nearly everything with a credit card. As Gordon Gekko once said: The point...


December 12, 2016

Ian's Geek Gift Guide 2016

I normally keep it businessy around here, but with the holidays upon us I thought I’d share some of the products that have brought me joy this year. If you’re stuck on what to get some people in...


November 15, 2016

Shady Tactics, Round 2

After my post yesterday about shady tactics in Bootstrapper circles people have been sending me other stuff they've seen that irks them. In the other post I didn't call out specific people because...


November 14, 2016

Shady Tactics in our Midst

Bootstrappers. I've been seeing a lot of shady tactics in our midst lately and I'm calling them out. These aren't good for you or your business long-term. Some of these have already entered the zone...


August 29, 2016

Are You Letting Today Distract You From Tomorrow?

What is on your plate today? My guess is that you are busy. You are running around with a To Do list one mile-long with things that need to get done, right now, no exceptions. There are meetings,...


July 19, 2016

Should You Sell To Enterprise Customers?

Money. The more the better, right? Customers. The bigger the better… right? When you’re a bootstrapped start-up, you quickly realize that neither of those assumptions are correct. Of course you...


February 11, 2016


People go to conferences with the wrong mindset. They feel as though they have to get a lot of information out of it or make a lot of contacts. They need to justify the expense with volume. For me,...


February 5, 2016

Travis Kalanick Interview This is simply a beautiful interview. If you're in business there's no way you can't love the clarity of his vision. The elegance of his presentation....


February 3, 2016

The Knife-Edge

You spend a lot of time as a bootstrapped software founder on a knife-edge. How can I afford to start a business? Will the business succeed or fail? Will anyone buy my product? Once you overcome...


January 31, 2016

Here's Why Devs Fail as Founders

I'm a big Seth Godin fan. You can see the signed #32 print of Purple Cow above. This print is probably my favorite bit of internet/tech swag. Anyway, he wrote something tonight that really struck me...


January 28, 2016

Laravel Gurus 2

Laravel Gurus is a little labor of love site I run. It's a simple listing of Laravel/PHP consultancies across the world. People kept asking me where to find a Laravel consultancy, now I just point...


January 28, 2016

The Hubris Bubble

There's been a lot of talk about tech being in a bubble lately, making reference to the Internet bubble of 2000. I generally don't agree with this, however, I do think we've reached a Hubris Bubble....


January 27, 2016

Overexposure to Excellence

One of the worst parts about running a business online is overexposure to excellence. The world is a big place. If you're on Twitter all day as so many of us are, you're bombarded with excellence....


January 26, 2016

Customer Success in SaaS

This quote on the latest Bootstrapped Web (a podcast I really enjoy!) by Jordan struck a nerve with me Do you hire for the least important things or least impactful things like customer support and...


January 25, 2016

The Product Business Cycle

This tweet from a developer at a local company got me thinking about the software product lifecycle. Perhaps you can think of building a...


November 11, 2015

How to Get Hired at a Startup

Applying for a job is thankless work. Literally, most of your applications will be ignored. Even great companies often won’t acknowledge job applications. In large part, this occurs because the...


March 18, 2015

Snappy is Saved!

Phew, it’s been a whirlwind of a week. Last Wednesday I announced that we’d be closing Snappy. It wasn’t an easy decision, but one I thought was right for all parties. You can read more about...


March 11, 2015

An Update on Snappy

UPDATE: We've found a great new home for Snappy and we won't be closing. You can read the update here: Effective today we’re won’t be allowing any new...


February 27, 2015

Convergence Insufficiency

About 10 years ago while I was building out HelpSpot I started experiencing intermittent dizzy spells. Dizzy isn’t even the correct word, but it’s the best word I have for it. It’s somewhere...


February 20, 2015

The Apple Watch Money Grab

The Apple Watch is Apple’s purest (first?) money grab to date. If you step back and really think it through, there is no other viable conclusion. At least not for THIS version of the watch. Maybe...


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