On Firing Yourself

CLIV

[Code that's Lasted Longer than any of my Girlfriends; Data Monkeys; Eliminate, Automate, Delegate; Tech Enabled Service; Grinding to Valhalla; Leverage Via Omission]

Thesis: To get the leverage you seek, work on your business, not in your business.

[Code that's Lasted Longer than any of my Girlfriends]

I was sitting in my room last night with a friend. One of those conversations where I was 95% focused on her but was watching my terminal out of the corner of my eye to swat any bugs that popped up from a decently involved change I had just made to WhiteWhale*.

When there was a lull in the conversation, I had quite a holy shit moment: in one form or another, the code that I was watching had been running for almost two years now.

I started writing our code immediately when we launched in July 2024, and it's about to be June 2026. The first few months involved aggressive writing and rewriting. But there's been some continuity the entire time: some of the lines (and a lot of the philosophy) from 2024 remain untouched, even if so so much else has shifted about.

Funnily, I was actually running WhiteWhale out of Tmux windows until January 2025, and backend wise, we rode one server in my basement right passed $100K ARR.

Fondly reminiscing on code, I'm sure I'm reminding you that I'm a total fucking nerd, but that's okay.

I may have said it before, but it warrants restatement: even if I was as good of a developer as I am now back in July 2024, it would have been impossible for me to write WhiteWhale in it's current form then... competence matters, but so does all the time we've spent trying different things out with customers and deciphering what they actually need, rather than what they say they want.

The same goes for capitalization, too: if we had started with more than the $3,000 that we did, I don't know how much faster we could actually move. I'm sure there's a number greater than $3,000 that could’ve sped us up, but the money on it's own would not have been enough. It'd be just as likely (if not more) that we would have burnt that money in a funeral pyre of inefficiency and moved even slower.

This week, a mentor said a phrase that stuck with me:

That they do. And a bootstrapped startup and a well funded one likely will take the same amount of time to find PMF… but both are more likely than not to miscarry and never find it at all!

This post is all about leverage, as so many things are. Particularly, how Jack & I have and are continuing to use code to build leverage into what started as a service business.

This is what we have to do if we want to get to particular revenue targets without hiring another soul. It also means being guarded against spending too much time running the business while still not optimizing it too soon. And, it's also why we're taking the final grand steps to Product Led Growth (PLG).

_{*Yes, it happened - we rebranded from BirdDog to WhiteWhale!}

[Data Monkeys]

Prior to starting WhiteWhale proper, Jack & I got about 6 months of experience speaking with sales people and manually delivering research services to them.

This was super valuable in what it taught us about our space, but it would have been an incredibly low leverage business if we tried to scale it.

The engagements were all a bit different, but they looked something like this:

• Sales team gives us a list of organizations they can sell to, say US based police dispatches

• We very manually did aggressive google searches and read meeting minutes trying to find trigger events, like quotes from leadership, grants, specific technology investments, open job roles, etc

• We would summarize the information in a little narrative supported by the data, saying target this org now because of these triggers (signals)

• This was delivered either as literal PDFs or in a low tech front end that was basically an interactive pdf

We would each spend over 40 hours a week manually delivering this to our clients, running around between a bunch of different sites and inputting the data into a spreadsheet with some particularly finicky automations.

It was very, very slow going. The business was capped unless we hired other people.

If we wanted to get bigger, the bulk of our costs would go up linearly with the business - if we wanted to add 2 more customers, we might have to hire 1 whole person! And even if this person was a VA from the Philippines, we would still require training and infrastructure and management to make it work. Meaning, hiring people would also increase the complexity of our business, too.

And, even if we hired a lot of people, it would be impossible to deliver the value we do now without a very large army of employees. Automatically, we now check tens of thousands of accounts for trigger events and other signals every other day! Good luck getting humans to efficiently do that!

[Eliminate, Automate, Delegate]

Before we continue along the WhiteWhale journey, I want to address a common question we get: why don’t we hire or outsource this or that?

There's two adjacent pieces of wisdom that give us pause about hiring:

This latter quote gives us an order of operations to follow when improving a systems:

1. First, Eliminate

2. Second, Automate anything you can't Eliminate

3. Third, Streamline (Optimize) & Delegate anything you can't automate*

Delegation and optimization are more expensive in the long run than either automation or elimination. And, both require upfront resources and time to get right.

So, yeah, I guess we could've hired a commission only sales person as early as November when ACV & win rate were both high enough to do so.

But, doing this is the lowest leverage & most expensive option in the stack - we'd need to first systematize a process and give it to them.

If you do that too early, you're optimizing something that might change rapidly. We didn't know we would go to PLG in November, but we did know something was still 'off' that we needed to solve. And we weren't ready to invest the time and effort into delegating something that might rapidly change later.

And now, we're convinced we can eliminate sales as a requirement to get new customers altogether.

All of this said, I must admit that Jack & I are on the slower end of streamlining & optimizing systems, and probably also slower on the automation bit, as well. This is a style of building that bootstrapping affords for us, and perhaps even neccesitates.

I’m sure we could be faster to automate & streamline, but I think it works out because we're a lot more trigger happy with eliminating things. Which, again, is the highest leverage option you can pick.

_{*Roping Streamlining & Delegation together is my personal view of the matter, as the goal is to bake leverage into the business. Streamlining doesn't give you as much leverage since it doesn't remove yourself from the task, and delegation is made easier by streamlining. Although, I do believe the 'last job' of a CEO is as the portfolio manager / investor.}

[Tech Enabled Service]

After the many ups and downs of building and selling software, at some point late last year, we realized that WhiteWhale was basically a tech enabled services business.

What I mean by that, is we had a piece of software that worked and provided value. This was a massive improvement, as we became removed from manually combing through the internet, looking for all of those articles and trigger events and signals. Now, our software was & is doing this across tens of thousands of our client's target accounts each night and automatically updating itself and presenting the information to them.

I don't know if you can appreciate how much this feels like magic until you use a piece of software that, at the press of a few buttons, does something that took you hours or tens of hours a week to do yourself.

However, a few very big things still required input from Jack & I:

1. Selling the software

2. Configuring & managing the software (defining & helping update the triggers and signal events)

3. Reselling / Upselling / Customer Success functions

While we made it out of the grindy, data monkey trenches, we found ourselves in a spot where without our continued input, the business would fail.

To be clear, this is not a 'bad' or untenable situation, but we had basically given ourselves jobs. As I wrote about a couple weeks ago, since we are our own bosses, this still puts us far closer to fuck you money than if we were making the same amount or even a little more at someone else's company. And, it's actually a sustainable situation, unlike our data monkey hustle of years passed.

But, the business was bounded both by our ability to get on sales calls with people AND our ability to properly onboard and support them after they bought. That’s not what we want!

We put a ceiling on ourselves. And, we impeded customer acquisition, too: because our time was part of what we were selling, we had to raise the minimum price far higher than the software neccesitated on it's own. This obviously lowered the number of people who would buy from us.

So, going back to our options of Eliminating, Automating, and Delegating, we're in the process of eliminating our sales function, automating the configuration and all other inputs we have to give to help someone get ROI on the software, and then doing a mix of eliminating / automating / systematizing & maybe delegating for the last bucket of items.

Altogether, this is & will give us more leverage than we've ever had.

[Grinding to Valhalla]

In practice, this looks like aggressively making a million changes that will keep moving us out of the loop while making customers happier and happier

• We got one of our customers to jump their commitment up from one quarter to 3 quarters with an automated email our system sent out about how WhiteWhale impacted their pipeline (showing ROI)

• We entirely rewrote our front end from scratch; it was on a no code tool, and now the new edition is not, and there is no Javascript framework; overall, it means we can iterate on it a lot faster than we could before.

• We wrote down everything we've learned about making good signals for customers, and built it into a system that does it on it's own.

• Our customers can upgrade their account within the platform without talking to us

• We added a wrapper over our signal input system that used to require users memorize a specific syntax, but now just accepts free text.

• The new front end also has a more intuitive to use account finder that mixes right in with the user's regular accounts.

• We’re adding a human readable log to the account searches that will eventually have recommended adjustments so users can understand & get better results

• Jack rewrote our website to have a much stronger funnel full of video customer testimonials from support calls.

• We’re finishing an onboarding flow that can take a user from nothing to having a configured account with signals and sample data before prompting them to buy without talking to us.

• We will re-document the new platform with videos & text

• We will enroll users who complete the onboarding flow in a sequence that remarkets those who didn’t buy and reminds those who do of the value of WhiteWhale and how to get it.

• We're gathering better telemetry that allows us to see where users get stuck or make 'mistakes' in the platform so we can code it out.

• At some point, we'll add in an AI CS tool to start resolving the low level support issues that you can never fully engineer away.

It's easy to get so caught up in running a business that you forget you’re building a business. This is perhaps one of my greatest shortcomings as an entrepreneur. But, we’re addressing it now.

If you enjoyed this post, subscribe - I’m here every sunday writing about whatever is on my mind, from the AI bubble to bullshit work.

[Leverage Via Omission]

There is a lot of hard work between where WhiteWhale is now and getting it to where Jack & I want it to be. But, there’s also a ton of hard work that's already happened between the time we were manually grinding on research and where we are now.

It's pretty cool that some of the code has been with us the whole way, and works for us without sleeping, without resting. That's a beautiful piece of leverage.

The most beautiful piece of leverage, though, is everything that's not there, all that we've already eliminated, and all that is to be eliminated.

Live Deeply,