April 14, 2022

Exploring Options

I read a few posts like this while gearing up for my job search that I thought were really helpful, so I thought I'd throw mine out into the world.

TLDR: If you're a remote tech worker, now's a great time to make a switch. My new job starts next week!

Yesterday was my last day at Dagger. I started there back in 2018, just one month after acquiring IntroCave (now Intro Maker). For a year or two before joining Dagger, I was actually half-time through my previous agency/studio (working on games half-time, working with Dagger the other half). When we decided to fully pause the game studio in 2018, Dagger made me a great offer (paraphrase mine):

"You're currently getting a lot of shit done in two days/week. Come work for us four days/week and we'll pay you the same salary you're making now."

For context, we moved from Silicon Valley to Atlanta in 2013. We made the conscious decision to trade interesting work for a better overall quality of life. Landing at a game studio for a few years was a big bonus (go play Little Broken Robots on iOS), but working at an agency is what I expected when we made the move. There are a few remote companies that I kept an eye on (Spry Fox, Basecamp), but their infrequent openings never matched up with my plans. There are startups in Atlanta doing interesting things, but they tend to be underfunded compared to California startups and the pay-to-risk ratio never seemed worth it to me.

That basically left big boring enterprise companies and agencies for the Atlanta tech job market. I prefer to wear shorts + flip flops most of the year (anything but *cringe* business casual *cringe*), so that left agencies. Luckily, there are tons of those in Atlanta!

After doing agency work for most of the last 8 years… it's not my favorite. This isn't meant as a knock on Dagger (who've been fantastic), but just the nature of agency work: time tracking, low budgets, quick turnarounds, watching scope, meeting clients at random times, translating developer-speak into client-friendly-speak, constantly switching gears. I'm a builder at heart, so the ratio of paper-pushing to actual work always seemed way off (even if that was purely a perception problem on my part).

I'd already been doing that for a few years, so I knew exactly what I was signing up for. I reasoned that I could scratch my "just build stuff" itch by tinkering on Intro Maker every Friday. That mostly worked!

Besides the 4-day work week, Dagger's offer had a few other things going for it: we shared an office for a few years, so I knew (and liked!) the whole team already. My main client was going to be Aflac, who I'd already done a ton of work for. I think I can say this without breaking NDA: they're one of the best clients I've ever worked with at either agency I've been a part of—always super friendly and way more reasonable than most clients.

My conclusion from 2018 hasn't changed: if I'm going to work at an agency, it would be hard to beat Dagger.

My rough plan was to work there for a few years while fixing/growing Intro Maker and then re-evaluate. Once Intro Maker recouped and I could start taking profits, I could either go full-time on that or buy another small internet business to piecemeal together a full-time income… or maybe just retire!

Actual retirement in the FIRE sense isn't that appealing, but sitting around the house tinkering on my own projects full time sounded *amazing*.

Then Covid happened.

It turns out that when you work from home full time, you mostly sit around the house tinkering on stuff.

The first year was extremely stressful, but now that the kids are back at school and the work has stayed remote… I may never go back to an office.

Instead of a commute, I work out for 80-90 minutes every morning and still sit down to start work around the same time.

I eat way healthier out of my own fridge.

My home setup (mechanical keyboard, 34" curved monitor, standing desk, sick camera) is way better than any office setup I've ever had.

I see my kids way more.

I can sneak out to the grocery store at lunch and don't have to run as many errands on the weekend.

The Zoom mullet is real – I wear gym shorts most of the time (not that I wore pants much at the office).

I assumed that everyone would get called back into the office eventually, but a bunch of tech companies have just stayed remote. Permanently. The choice was no longer "best agency in Atlanta" vs "do my own thing.""

Decision time: buy another internet business (original plan) or submit to the technical interview grind for higher remote pay at a FAANG/late-stage company (new plan).

Option #1: Start a Micro Private Equity Empire (microPEE?)

MicroAcquire also launched during Covid and hugely expanded the market for internet businesses. When you combine that with stupid-low interest rates, that's both a good thing and a bad thing (for me… it's 100% a good thing for the world. <3 MicroAcquire).

It's a great thing if I decide to sell Intro Maker! There's way more demand than there used to be at the low end of things (both from people moving into alternative assets and because there are way more buyers). According to their most recent report, multiples for sites my size are in the neighborhood of 4.2X revenue or 7.1X profit. Intro Maker would likely be a bit lower since it's a mix of sales + ads + subscriptions, but I think I could reasonably take it to market in the $250-500k once the dust settles from my recent price tinkering (not too shabby for a side hustle!).

It's a bad thing if I want to buy a 2nd internet business on a similar scale. I paid somewhere in the neighborhood of a 3-3.5X multiple on profits (fuzzy because of earnouts). With some interest charges and topsy-turvy traffic, it's taken around 4 years to break even. Without significant growth, buying at 7X profit could take 8-9 years to recoup if I finance a new site. No thanks! (This would actually still make sense if it was under $100k and I knew exactly how to fix/grow it and felt like I could double it in size in 1-2 years).

I'm following a few folks who are running "further along" playbooks in the MicroPE space: Eyal Toledano at MicroAngel.so and Andrew Pierno at XO Capital. Just going by what I've read, they seem like they're doing a lot of outreach to find sites they can buy at more of a 3-4x multiple.

I don't want to do outreach, so I'm not sure how feasible this plan would be today.

In both of those examples, they also seem pretty comfortable doing paid ad spend. It's a skill I would need to learn if keep at this–I don't think I'd buy another site that was so heavily dependent on organic search traffic.

If I go a little bigger, multiples for businesses above $100k annual revenue get more reasonable (3X revenue, 4.1X profit). There are a ton of alternative financing options popping up. With a bit of legwork, I think I could buy something in the $500k-$1m pricetag range (which after debt could yield something like $70-140k/year along with maybe $40k from Intro Maker).

It's a pretty attractive option on paper, but it has two pretty big downsides:

First, it would make buying a new house a lot tougher. Now that we're both fully remote, we want to buy a bigger house sometime later this year. Preferably somewhere with lake or river access so we can go paddling all summer.

Second, the timeline is not something I can control. I ran spreadsheet models on a bunch of businesses for 1.5 years before buying Intro Maker. I put in offers on a few others, but not every offer leads to a sale. I've been browsing listings on MicroAcquire for almost that long and have only put in a couple of offers. It could take another 2 or 3 years to find the "right" business.

Option #2: Do the Tech Interview Grind

I don't think I had really interviewed for a job since 2010. The modern technical interview has crystallized into a very specific format that is… not fun. It also takes a whole bunch of time. I talked to a few companies before joining Dagger back in 2018, but none of those conversations resembled anything like the gauntlet that you face today.

I went into my first interview thinking "oh it'll be a couple of friendly chats" and was not prepared for the format. It went so poorly that I almost said "fuck it, not worth the stress."

I saw this tweet today and it really resonated:

The interview process walkthrough at jobsearch.dev was super helpful. They recommend quitting your job and spending months on the search full time, along with doing a bunch of practice sessions. The tactical advice is helpful, but the mindset advice is probably the most useful.

I also talked to a couple of friends who'd made similar moves in the last couple of years. The feedback I heard matched up pretty well with the jobsearch.dev instructions: treat it like a game, practice, don't get discouraged, build up a target list, and most importantly: it's worth the slog.

I started signing up for engineer-specific job boards. I thought the best sources for me were the Not Boring Talent Collective, the Pragmatic Engineer job board, and We Work Remotely. RemoteOK was where I went first, but I had a hard time finding any high-paying jobs. I feel a little bad for them… these companies that were remote before remote was cool are probably struggling to compete.

I started putting together a target list: Stripe, Square, Shopify, Twitter, Meta (Oculus), Airbnb, Netflix.

Looking at my list, I decided to budge on a previously-strongly-held-belief: "React sucks."

I tried node.js when it first came out and have built a few prototypes over the years. Ditto for React. I strongly disliked the javascript ecosystem of circa 2015 and have mostly avoided it ever since (getting by with good old jQuery and server-side rendering). My original argument was sound: I want to build CRUD apps in Rails, and the types of apps I want to build don't benefit much from being a single-page app (plus throw in some handwavy SEO arguments).

I used to feel the same way about PHP. I used it in school in the mid-2000s and a few times over the years for WordPress tweaks, and every one of those experiences felt archaic compared to building something in Rails (<3 IRB). Then I bought Intro Maker (built in Laravel). Laravel is great. I wouldn't say I love PHP today, but I realize now that dumping on 2007-era PHP isn't really fair to the 2022 PHP ecosystem.

What felt like a fad to me back in 2013-2014 has turned into an industry juggernaut. Whoops… but also: Typescript and the javascript ecosystem have gotten so much better since I last gave it a serious look.

I've been tinkering with Typescript on a few game updates/prototypes. I took Wes Bos's React for Beginners course. I started rebuilding one of my old games in React for practice. Node dependency management seems pretty broken still, but the tooling has come a long way.

Finally, I put together a list of other things that would make a company interesting outside my target list (which mostly fall under the umbrella of "get paid to learn cool shit"):

  • anything on the GPT-3 or AI interaction side
  • anything crypto-related that doesn't look too scammy
  • anything on the creator economy side (tools for streamers, content creation, etc)
  • something in a new framework/tech I haven't used professionally yet (Typescript, React, Elixir/Phoenix, Tailwind, Rust)

When I stumbled across a listing for Copy.ai, it checked a lot of my goal boxes: GPT-3, Typescript, React, creator economy. I was already following both founders on Twitter (one of the reasons GPT-3 was even on my "cool tech" list) and loosely familiar with the product. I had no idea that they'd grown so fast or raised a Series A. If they hadn't included a salary range on the post, I likely would've skipped it: "It would be fun, but they probably pay bootstrapper wages."

I swapped a few emails with their head of engineering and did a few Zoom calls. The tech screen was a reasonable task similar to scripts I've written many times over the years. The onsite was more of a meet n' greet than a meat grinder. They're fully remote, everyone seemed super friendly, and they were cool with letting me pick up their tech stack on the fly.

I start Monday!