Prelaunch lessons learned bootstrapping a startup
Five months after going full time on my startup I’ve learned a lot. Here’s a rundown of the major lessons I’ve learned so far.
In late March, I announced that I had quit my job to bootstrap Writing.AI, a startup based on the idea that a conversational approach to writing could help a lot of people get their thoughts on paper more easily.
Since then, I’ve learned a number of lessons that may help guide others following a similar path. Here’s a list of my top takeaways to date.
Having support is critical
Don’t go it alone
In 2006, Paul Graham famously listed ‘Single Founder’ as the #1 item in his list of mistakes that kill startups. Since then, the topic of solo founding has and will continue to be debated to death.
Like so many things startup-related, the prevailing wisdom on this topic will be considered gospel by some, taken with a grain of salt by others, treated as a straw man by controversy seekers, and ignored by most everyone else.
Needless to say, as a solo founder, I don’t think having co-founders is a requirement for building a successful startup in 2017.
That said, the main reason Graham gave for not solo-founding is too often overlooked — lack of a support network to help you through the lows is killer. And everyone has lows, even Elon Musk.
The truth is that, while having a support network is critical, there’s no reason why that the network has to come in the form of a co-founder. In my case, my amazing wife has been essential to helping me work through issues, organize my thoughts, and generally keep my mind in a good place.
I’ve also been lucky enough to find an exceptional advisor, leaned on friends and family for feedback at times, and found great support in the co-working space where I’ve set up shop.
So if you’re setting out to launch a new startup, find a support network. But realize that it doesn’t necessarily have to be in the form of co-founders.
Hang a shingle on the first day
Give future customers a way to connect with your startup
If you’re setting up a company to make money, you want to give people a way to connect with your business as soon as possible. The best way to do this is to set up a basic website with a high-level description of what your startup is about and a sign-up form to collect email addresses.
Setting up a prelaunch page immediately was one of the best decisions I made early on, and I’d strongly recommend it to anyone else starting out. There are a number of services available for quickly setting up a landing page, and I’m sure they’re all great. I initially set up a simple site on a DigitalOcean droplet that saved email addresses in a database.
So hang your shingle early, because…
Exposure can come from unexpected places
Cast a wide net when discussing your startup
When first starting out, I did a bunch of basic internet marketing tasks that you might expect of a new startup trying to raise a bit of awareness. I wrote an announcement post on Medium, set up Twitter, Facebook, CrunchBase, AngelList, and LinkedIn pages, told my family/friends, and updated all of my online profiles to link to my startup.
I’ve had varying degrees of success with these efforts so far, but none have resulted in a large amount of traffic to my startup’s website. No surprises there, marketing is hard and people on social networks are constantly being bombarded by products and services claiming to be the next big thing.
Despite the middling success I’ve had raising awareness through these traditional channels, I currently have several hundreds of users signed up on the Writing.AI prelaunch email list. Where did they come from?
The vast majority read a single comment I wrote one morning on a Hacker News thread titled “What are you working on?”
As you can see below, that one comment drove more traffic to my site than anything else I’ve done.
In the week following that comment, about 250 people joined the Writing.AI prelaunch announce list. For a bootstrapping solo-founder without a large social media following, this was a huge lift.
I took a couple things away from this event:
- First, and most importantly, some strangers were genuinely interested in what I’m building!
- Second, marketing through traditional channels is a grind, and the traffic you get through those channels doesn’t reflect how excited people are about what you’re building.
If you can connect with a lot of people where they are and explain what you’re doing, the message has a much better chance of reaching potential users.
Make steady progress
Do *something* every single day
As I mentioned, founding a startup will cause you to experience both highs and lows. This is true of both early- and late-stage companies. However, many of the external factors that help push you through the low periods in later-stage companies (employees, customers, cashflow considerations) just aren’t there when you’re starting out.
One of the ways you might get around this issue is to launch as quickly as possible. For Writing.AI, this wasn’t a great option because I wanted to spend time researching and experimenting with the system’s design before building the product.
Luckily, about a year ago I came across the excellent Loop Habit Tracker app to nudge myself toward some better daily routines. Of course, one of the habits I started tracking a while back was whether I had worked on my startup.
This was probably one of the most effective steps I’ve taken to date. Since going full time, I can honestly say that I haven’t gone a single day without accomplishing something related to the company or product.
This doesn’t mean that I’ve been overworking myself. I’ve been in tech long enough to recognize the signs of burnout in myself, and take particular care to manage my sleep and energy level from day to day.
But there have been a couple days where it was getting late and I hadn’t done any work on the company. On those occasions, pushing myself to make a bit of progress has helped me fight through some of the walls of mental resistance that pop up from time to time.
So watch your energy levels, but don’t discount the value of making steady progress each day.
Declutter your home to declutter your mind
The magic way to boost your motivation
I realize I’m edging dangerously close to self-help/GTD/Marie Kondo territory here, but I really believe this point is important enough to warrant sharing.
My final day at my previous job was a Friday. That weekend, I opted against working on my startup in any way. Instead, I spent the whole weekend cleaning and, more importantly, removing as much clutter as possible from my home.
It’s hard to overstate how incredibly effective this act was at helping me focus during the week that followed. The removal of a significant stressor — clutter — did wonders for my energy levels.
So if you’re in a bit of a rut and your place is cluttered, consider taking some time to clean it up. Best case, you’ll magically have more energy. Worst case, you’ll have a cleaner home.
About this article
This article is part of a series drafted using Writing.AI, a new approach to writing designed to make the process faster, easier, and more accessible. If this sounds interesting to you, sign up for a launch announcement at https://writing.ai or follow @writingai on Twitter.
