My Failure Resume

I was listening to an episode of Without Fail — great podcast by the way from one of the greatest podcasters of all time — Alex Blumberg.

And the guest on the podcast — Nina Jacobson — talked about the importance of your “Failure Resume”, which is basically a list of all of the failures that you’ve had — the idea being that you are more defined by the failures that you’ve learned from than you are by your successes.

It was an all-around fantastic episode and it inspired me to finally put in writing something I’ve been wanting to do for a while now — something I now have a great little term for — my failure resume.

It seems like every time I sit down to put together this list I always feel like I’m forgetting tons of things, so I’ve never gotten it out the door — but the concept of a “resume” actually made it easier for me to wrap my head around, because your resume is something that is always changing and being iterated on. So if I leave something out, I’ll just add it in later.

Alright, so here goes…

Caltech EE Course

When I was in college at Occidental College I took a course at Caltech (there was a course exchange agreement between the 2 schools). I’ve heard it’s one of the hardest courses at Caltech, and Caltech in general is, let’s just say, a tad more academically rigorous than my school was.

I must have worked about as hard on this course as on the rest of my course load combined, and I was barely hanging on by a thread. I think I ended up with a C+ or B- or something like that — the only non-A I got in college other than that Vulcanology class in Ecuador (they said it was supposed to be a breeze!).

Masters Program

When I was a couple of years out of college I got it into my head that I might like to get my masters and maybe try to teach (something I’d always thought I’d do growing up). Being a few years out of school and having a full time job, my head was in a completely different place academically from back when I was a full-time student.

I was barely keeping up with the class, and I remember when I did my class presentation, these snarky kids were peppering me with questions that I knew and they knew I didn’t really have good answers to. I remembered that I used to be that snarky kid.

After barely passing that class, I quit the Masters program.

Agency Owner

I started freelancing on the side while working at my 2nd job out of college and did fairly well with it. Was able to quit the full time job and go full-time self-employed, which was exciting. Freelance went great until I started to make the obvious move which was to begin outsourcing some of my work to contractors.

I quickly found out that I wasn’t very good at outsourcing — long-time, happy customers became disgruntled and were asking for refunds. I then took on a huge project that was way outside of my comfort zone (lot of Flash involved and I just knew PHP) — ended up crashing and burning so hard that I had to get out of the self-employed game altogether. Went back and got a job as a project manager.

That time I got blackmailed

Ever have one of those memories that you’re not even sure is real because it seems so bizarre and has been a long time since it happened? Well, back in the day when I was outsourcing, I made the mistake of giving production credentials to a contractor I was looking to hire to do some work on a client’s site.

(I can see you looking at me with that judgy look in your eyes, but like I said…I was bad at outsourcing)

I decided not to go with them for one reason or another, and they told me they installed backdoor on the site and were going to take it down if I didn’t pay them. I think it was like $250 or $300 bucks.

Immediately after I saw their threat, I freaked out and was sitting there thinking of how to handle it or block them or figure out where the backdoor is. Then they said something to the effect of “you’re probably trying to figure out where it is, it’s too late” or something like that. Damn. This dude had me good.

Paid the money and felt like an idiot.

Failed Project Manager

I spent 4 years as a PM. If you would have asked me at any given time I probably wouldn’t have described myself as a failed PM, but on the whole, and looking back, that’s what it was. There was a ton of frustration with the job, lots of clients that were unhappy for one reason or another.

Hard to say whether I was at fault or whether it had to do with the sales process for the agency I worked at — but at the end of the day it was a failure and many a day I felt like a giant failure. Massively discouraged a lot of the time.


One of the things that I wasn’t such a failure at was getting freelance business off of craigslist using some…let’s call it…marketing automation. I tried to leverage that automation in a few different directions, one of which was a Yelp-like idea called Hoodlist, where I tried to aggregate service providers that I could reach out to on Craigslist.

It…didn’t go very far.

Most of my open source stuff

Most of the open source projects I created (56 at the time of this writing) didn’t really go anywhere. A couple of them got some traction, but the other 10 or so didn’t really get any at all.


I came up with the bright idea of trying to build some automation around Magento upgrades, because of how painful they are. I built some cool tooling including stuff like source code diffs against core, and implemented a handful of upgrades that actually went pretty well and which I was able to do much cheaper than most people.

I remember at one point I was discussing an upgrade with a pretty interesting website — let’s just say it’s a single word .com domain name like (but not blinds).

I believe we were discussing an upgrade for somewhere in the ballpark of $3k. Sounds insane, right? They turned it down because it was too expensive. At that moment, I realized that while there was a huge pain around Magento upgrades, that didn’t necessarily mean that there was a willingness to pay for them.

Pain and willingness to pay — 2 different things.

Flappy Birds Training Video

If you are a longtime Magetalk listener, you probably heard Phillip Jackson make fun of this a few times. Yes it’s for real — back during the Flappy Birds craze, I played it a good bit and got pretty good at it.

I’d seen lots of instance of people being able to make money off of silly little fads, like the fart apps and stuff like that. So I threw up a page on some platform that lets you sell electronic content and did a video showing my technique for playing it.

It…didn’t generate very many sales.


After seeing success with my first SaaS product, I started to think about building a new business with the social impact goal of creating high-value jobs for people with a minimal amount of education needed — the niche I landed on was link building.

Despite the fact that I didn’t really know anything about link building, I dove into it and figured some things out pretty quickly, got a number of clients on board, reached over $10k/month in recurring revenue, and brought on a good friend of mine as a partner.

Things fizzed out with my partner and then we decided to close up shop. Was a difficult time but, hey, that’s when I created Commerce Hero, which thankfully isn’t on this list.

Well, that’s about it, so far. So if you’ve ever thought of someone like me as an “overnight success” with building a successful business, just realize that’s very far from the truth.