The Trouble With Side Projects

Lucas Lindsey
Makers Gonna Make
Published in
10 min readJan 3, 2016

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Here’s a handful of things I’ve learned sending a weekly newsletter to 400 people and probably a couple of bots.

Last year, alongside my buddy Frank, I started Writrsbloc, a foray into content discovery that’s comically simple but criminally time consuming. In a nutshell, I select a handful of the week’s best stories, package them into a newsletter, and fire off a weekly email. My only rule is this: Send an email I’d want to receive packed with stories I’d want to read. Every now and then, I manage to stick to the rule.

To my surprise, sending Writrsbloc has quickly become my favorite thing to do each week (aside from driving with my wife every other Friday to a killer, hole-in-the-wall Mexican restaurant hidden deep in Florida’s panhandle; tweet @urbnist, and I’ll send you directions).

Side work creeps up on you like that. One day you’re commandeering emails from friends and family. The next day you’re combing through links. And before you know it, you’re the proud owner of a full-fledged side project. The good news is, despite all the trouble, side projects give you total permission to learn, learn, and learn some more. What follows are a few takeaways drawn from my own side project experience.

Since March, Writrsbloc has compiled and shared 125+ links to can’t-miss stories. The goal is fairly straightforward: improve content discovery and increase the audience available to talented writers, journalists, and bloggers.

Spiky vs. Smooth Growth

Here’s the first half of a hunch I have: When you don’t have true traction, new users overwhelmingly arrive in batches. Allow me to explain.

I can track a significant slice of Writrsbloc’s subscriber growth to three acquisition events, or batches, in the product’s life: 1. A paid feature on Betalist + Startuplist, 2. A vendor booth at Word of South (a literature and music festival), and 3. A front-page-but-definitely-buried spot on Product Hunt.

In total, 469 people have subscribed to Writrsbloc since March 2015. 368 of those subscribers arrived via batch. Put another way, 78% of Writrsbloc’s subscribers were acquired over just 16 days, or 5% of its 2015 product lifetime (March 8 to December 31).

Writrsbloc Subscribers by Batch

From this perspective, batches are highly efficient in terms of the rate at which they drive user acquisition, but they are also difficult events to mastermind, especially for someone working on the side. They take significant upstream investment to materialize, demand oft-underestimated downstream management to leverage, and offer diminishing returns relative to a growing user base (assuming, of course, you can repeat them at all).

I’ve taken to calling this sort of batch-heavy acquisition spiky growth, and I think about in contrast to smooth growth. Spiky growth hinges on staging acquisition events that temporarily inflate traffic and social momentum. Smooth growth relies on sustained word of mouth and organic referrals. One’s a clocktower, the other’s a metronome. Both may leverage loud moments of virality, but only one does so sustainably. The point here is not that spiky growth is undesirable — indeed some growth is better than none! — but that it’s a time-intensive, stop-and-start sort of acquisition strategy.

The funny thing is, side projects seem predisposed to spiky growth. That’s because sidepreneurs (I did; I said it; there’s no going back) have a tendency to work in sprints, not marathons.

You see, the trouble with side projects is that you do them on the side. This was true for me, especially when it came to managing social media, investing in community, and iterating forward. As a result, my organic growth suffered from neglect, and I focused on the only kind of acquisition momentum I knew: the low-hanging fruit of web features and event tabling.

Spiky growth is characterized by short bursts driven by standalone acquisition events. Highly efficient and hard to sustain, but seems to be a necessary precursor to arriving at real traction. FYI: the higher your churn between batches, the steeper the peaks get. Solid retention will make this baby look like a set of stairs.

Seeding spiky growth with acquisition events takes a ton of time and hustle, which means working toward smooth growth is critical for side projects, regardless of whether you want them to comfortably cash-flow, passively collect emails, or develop into full-time ventures.

This is the thing you have to come to grips with: Sustainable smooth growth does not happen without product/market fit. That’s because weak word of mouth is a euphemism for weak product/market fit. And without product/market fit you won’t achieve scalable onboarding, which means you’ll be stuck in a side project limbo that relies too heavily on conjuring up high-touch batch acquisition events.

The trouble with side projects is that having limited bandwidth makes it difficult to admit weak product/market fit. When things don’t take off, when you don’t stumble into the viral lottery, you blame your own lack of time and focus, not the product itself. I’d have more traction if I just had more time, you tell yourself. And so, the side project, by its very nature, gives you an excuse. It gives you a scape goat in the face of critique or self-doubt.

Don’t be afraid to honestly and critically assess your value. It doesn’t matter if users tell you that they like your product. What matters is whether they tell their friends. That’s the real, observation-based measure of traction. The rest are just social niceties.

Smooth growth is characterized by sustained word of mouth unattached to discernible acquisition events. From where I’m sitting, this can be a healthy sign of product market fit. If a side project has serious smooth growth, it likely won’t remain a side project for long.

Now that we’ve cleared the air, let’s take a deeper look at each of Writrsbloc’s three batches. Again, these events account for more than 3/4 of subscribers.

The First Batch
Aside from 30 or so friends and family signups, this was the first kick in the pants. 213 people subscribed within 7 days of features on both Betalist and Startuplist. This group was invaluable as a motivator (momentum is fun!), but turned out to be vanity batch more than anything. We’ll get to that, though.

Without referral tracking, I can’t say for certain exactly how many originated directly from Betalist and Startuplist, but it’s safe to say that all the hullabaloo drove traffic and awareness even among my friends, family, and professional network. Thus, it’s highly likely the batch event was the motivating factor for most new subscribers over that 7 day period.

The Second Batch
64 subscribers handed over their email at Tallahassee’s two-day Word of South festival. They braved the rain to hear a ton of top notch live music, meet world-renowned authors, and graciously abide my 15 second pitch. This was my do-things-that-don’t-scale moment, and I’ll definitely be back at 2016’s festival. Keep on scrollin’ to Batches Be Complicated if you want to see why (aside from the fact that it was a total blast).

The Third Batch
91 subscribers joined up within 7 days of Writrsbloc hitting Product Hunt’s front page. The project received 65+ upvotes and engendered a lively comment exchange between me and David, a Product Hunt user who seems like a good guy with a penchant for pointed but ultimately helpful constructive criticism.

WARNING: The numbers I’ve already showed you and continue to expound upon below have some assumptions baked in. They are, at best, an approximation, but first of all isn’t everything and second of all that shouldn’t spoil the fun because they’re my best attempt at an honest approximation, and that’s more of fair shake than you’ll get from most hucksters in the midst of these end times. I guess what I’m saying is, obsessively track your numbers from the get-go, folks. Because I didn’t, and as a result this summary is taking way too damn long to write while home for the holidays, sitting here in the room I grew up in next to an overworked space heater that has been exhaling for hours what I presume to be its final, dying breath.

To be clear, spiky growth has significant upside. For someone working on a side project, someone constantly assailed by the self-doubt of trying to do anything even halfway entrepreneurial, there’s no greater motivator and nothing more fun than a viral burst.

So I’m not saying to avoid batch acquisition, I’m just saying not to rely on it. In fact, I think the ideal growth model is something of a hybrid and, incidentally, nothing of the sort I’ve yet been able to achieve. Harness the momentum of intermittent spiky growth, talk to users, and work iteratively toward a smoother, steeper curve underpinned by genuine product market fit and the sort of kickass product people can’t help but share.

Batches Be Complicated

Here’s the second half of a hunch I have: not all batches are created equal. In Writrbloc’s case, the real story isn’t just subscribes but also unsubscribes. Inconsistencies in who said sayonara and when they pulled the ripcord reveal a lot about the variable effectiveness of different batches.

Of the original 469 subscribers, 75 unsubscribed, leaving Writrsbloc with a rag tag survivor crew of 394 subscribers. Interestingly, unsubscribes were not uniform across batches. Some batches proved significantly stickier than others. The data breaks down like this: 57 of those that unsubscribed were users that onboarded in the First Batch. 6 onboarded in the Second Batch. 6 onboarded in the Third Batch. And 6 onboarded organically, outside of the 16 days we’ve presumptively grouped into batches.

Writrsbloc Unsubscribes by Batch

That means the First Batch (Betalist + Startuplist) accounted for 76% of Writrsbloc’s total unsubscribes, and that I lost fully 27% of that same batch to good ‘ol churn. In contrast, I lost just 11% and 7% of the Second and Third Batch, respectively. Finally, I lost only 6% of the organic subscribers. It’s a little bit like reading tealeaves, but these numbers tell me two things.

First, the more targeted the batch, the better (no earth-shattering news here). The stark difference between the First and Second Batches underscores this point. Writrsbloc lost subscribers from the Betalist group at almost 2.5x the rate of the Word of South group. If I’m pushing a solution to share stories, it makes more sense for me to search out the kind of readers and writers that would attend a literature festival than it does to get in front of tech adopters whose broad set of interests I cannot clearly anticipate.

Second, Writrsbloc’s most committed users were those who self-selected organically through word of mouth or by going down the Internet’s rabbit hole of serendipitous discovery. Coming in just behind were those that arrived via highly targeted batch acquisition events. So if, by some arcane magic, we can combine the two: Voilà! That sweet, sweet hybrid growth.

Bonus Lesson Part I: Everybody Likes a Good Back Scratch (I Almost Made You Download a Free eBook For This One, But What The Hell; Nobody Needs Shenanigans Like That This Early in 2016)

People are irresistibly self-interested. It’s a time honored fact that honest graft greases the gears of the Internet, so never underestimate the power of a shoutout.

My favorite part of curating and sharing great writing has been leveraging social media to meet and talk with great writers. Tagging and mentioning authors was one of the single most effective ways Writrsbloc amplified its social reach and helped drive quasi-organic growth. It also gave me a meaningful icebreaker, them an actionable but humble way to self-promote, and both of us a shared foundation for future conversation. Much a side project’s value lies in establishing credibility and expanding your network.

Building on this idea, Writrsbloc will expand its original content in 2016 by venturing into interviews with up-and-coming storytellers. As an aside, if you know someone that should be interviewed, get with me on Twitter.

It’s hard out there for a tweet, unless you play that mention game.

Bonus Lesson Part II: Startups Have Itchy Backs, Too

I use a handful of web tools to help me package, send, and track Writrsbloc. Over the course of the week, I save headlines to Pocket and come back later when there’s time to really dig into the stories. I run links through Start A FIRE, and ultimately build and send the newsletter using Revue. To top it off, submission suggestions are accepted via Typeform. As far as I’m concerned, each service is a good faith partner, whether formalized or not, and I put in time on their behalf to provide feedback and act as a brand evangelist.

I originally left Revue for MailChimp, but their responsiveness and founder level access was ultimately too damn impressive to pass up. Martijn worked to implement low-hanging feedback in less than a week’s time. Who wouldn’t want to support a startup and a founder like that?

It’s hugely rewarding to not only use an up-and-coming startup service but also root for them along the way. When you co-build with other startups, traction is mutually supportive and self-reinforcing. Any success I manage to eek out adds value to Revue’s ecosystem just as their success helps stack the odds in my favor. Good companies understand this. They respond to your needs and trust that an investment in you is an investment in themselves. Just make sure to remember that support is a two-way street. Be ready to thankfully throw down a few bucks or a tweet for their trouble.

What goes around, comes around. Revue ended up featuring Writrsbloc in December, long after my feedback messages dissipated. Give first, and you’ll sure as hell get later.

In Closing

I curate and share Writrsbloc each week because it is both intellectually and emotionally compelling. Because while there might be a ton of trending content discovery tools — including some robust ones like This., Pocket, Nuzzel, NextDraft, Longreads, or Longform — I’m still driven to build a solution my own way, not just for the problem, but for the process, the learning, the nuts and bolts of the whole tortuous experience.

And that, it turns out, is the real trouble with side projects: When you start to do something you enjoy, you want to find ways to do more of it, the odds be damned.

P.S. Want to join the Medium batch? You can subscribe to Writrsbloc right here.

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Lucas Lindsey
Makers Gonna Make

Curious connoisseur of urbanism, community development, and startup economies. Build Better Communities. http://www.urbnist.com/