Daniel Vassallo Profile picture
Feb 21 19 tweets 3 min read
Why bootstrapping is riskier than you think:
When I quit my 9-5 job, my plan was to bootstrap my own SaaS business. I wanted to identify my ideal business opportunity, and try to make a living out of it. And if that didn't work, I was going to look for the 2nd best opportunity, and give that a shot. And so on.
The idea was to do things in series until something worked. This sounded very reasonable at the time, but that feeling didn't last long.
The problem was uncertainty. How much time should I give until I declare something a failure and move on to the next? And what exactly is failure? What if something was succeeding slowly? And what if a more interesting opportunity emerged while I was still trying something else?
While I had a decent runway to experiment, it wasn't infinite. And time was ticking. Then, about 6 months in, I had an epiphany. I realized that in this early phase, I shouldn't be trying to find the ideal opportunity.
Instead, I should first try to make my self-employment arrangement sustainable. I needed to stack the odds in my favor and do my best so that this lifestyle doesn't get taken away from me. The rest became secondary.
This idea changed my perspective. What I started caring about wasn't succeeding, but not failing. I simply didn't want to go back to a 9-5 job.
More specifically, my new strategy was to find a few small wins: opportunities with a quick payoff that required very little upfront cost, effort, or lead time — even if that meant that they weren't the most enjoyable and had very limited upside.
Then I'd try as many of these small bets as I could, and run them almost in parallel. I would keep what works, and throw away the rest.
So that's what I did. I was already working on a SaaS business at the time (Userbase), and I decided to aggressively cut scope and launch it immediately.
I also decided to try self-publishing a technical ebook (The Good Parts of AWS), and I intentionally chose a topic that could almost write itself. I time-boxed the effort, start-to-finish, to just 4 weeks.
I even started doing some freelancing (about 20 hours a month), mostly to randomize things a bit and potentially expose myself to new opportunities. But this income stream was very much welcome too.
In the meantime, I was also building an audience, which I was seeing as a source of incredible inspiration and opportunity.
Then I got a bit lucky. I found some freelancing work quickly, and it immediately gave me a decent income baseline. And at the same time, I released my AWS ebook and it sold $40K in the first 2 weeks. And it kept selling.
After months of seeing negative numbers accumulate in my bank account, I suddenly started seeing some surplus.
And this is what I've been doing ever since for the last 2.5 years. Keeping a surplus in my bank account via a portfolio of small safe-to-fail experiments. Doing things that don't scale.

My profit for the last 24 months averaged $23,098/mo. Who cares about scale?
So, how can YOU build your own portfolio of small bets?

First, remember that to thrive, you must first survive. The order matters. Start with the low hanging fruit and make your self-employment arrangement sustainable.
What satisfies that requirement depends a lot on your circumstances. Explore your strengths and opportunities, and try to imagine some quick wins you can pursue. Once survival stops being a pressing concern, go for some more ambitious opportunities.
Mix different income streams to tame uncertainty, and when some bets start paying off, eliminate those that are least enjoyable. As soon as you can afford it, optimize for enjoyment. Otherwise, none of this will last!

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More from @dvassallo

Feb 3
Today is my 3yr anniversary since I started working for myself.

I made $760K in revenue, and had a few realizations along the way. Here are some of them:
Something I wish I got exposed to sooner is the idea of cultivating multiple independent income streams.

All work activities fall in one of two categories. What works for one is counterproductive for the other.

Read 16 tweets
Dec 11, 2021
This doormaking book I’m reading might be the most entertaining book I’ve ever read. amazon.com/gp/product/161…
The author is smart too, not just funny. He gets Taleb’s turkey problem:
Tradition: “The art of doing it the same way it has always been done because it works.”
Read 8 tweets
Sep 26, 2021
If you put 10,000 hrs practicing the piano, you will almost certainly become very good at the piano.

If you put 10,000 hrs into your business, it doesn’t necessarily translate to anything!

The first kind has a predictable relationship to effort. The second kind doesn’t.
You need a different attitude when trying to achieve the unpredictable:

- Instead of consistency of effort, you need intensity when the right opportunity emerges.

- Instead of focusing on one thing, you need exposure to randomness and serendipity.
- Instead of a rigid plan, you need freedom to explore and some aimless wandering.

- Instead of external motivators, you need intrinsic drive.

- Instead of repetitiveness, you need variation.

- Instead of stability, you need insurance against what you can’t tolerate losing.
Read 4 tweets
Sep 13, 2021
How it started How it’s going ImageImage
I also bought kaleidoscopeboards.com while waiting for the glue to dry :)
Color pop:
Read 4 tweets
Aug 19, 2021
How to be happy:
Learn your true preferences. Life becomes much more pleasant once you stop chasing the preferences of others.
Try new things, take what works, and throw away the rest.
Read 19 tweets
Jun 30, 2021
Different ways to approach work:

You start with an idea (a product, a job title, a career, etc.), and try to make it a reality at all costs.

Good, but what about the rest of your life? And what if your idea turns out to be a dud?

You start with what you have, and try to maximize the most likely way to make the most money.

Good, but when do you stop? And what if you hate what you’re doing?
Read 5 tweets

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