Welcome back, Owners.
It is crazy to think that THREE HUNDRED and SIXTY THREE issues ago I started this newsletter as a ‘Buy & Build in public’ challenge.
At the time we had the feeling that newsletters was going to become the next ‘thing’.
The thesis was simple:
1. Content would become easier to produce and socials would get saturated
2. Organic slows and ad cost rise as people need to pay to get customers they cant earn
3. Owning the relationship via the inbox becomes a compounding value & defensible play
Furthermore, the thought process at the time was if you execute media really GOOD then you can achieve the elusive ‘Net, Negative CAC’
eg. get paid to acquire customers… because your media generates revenue via sponsors & other wise
A few milestones… since then…
We were able to grow the newsletter to 10,000…then 20,000….then 30,0000, then 40,000… then at one point 50,000+ weekly subscribers and kept it there
We used the newsletter to launch a community of 3,000 bootstrappers … literally built in public via polls from this very newsletter
We used the newsletter to launch our YouTube channels and grew that to…
2,000 subscribers
10,000 subscribers
25,000 subscribers
50,000 subscribers
and now we are up over 70,000 subscribers 🥳
We used the newsletter to publish our books & generate over 3,000 sales in the first week!
And yes… we even were able to sell some sponsors and achieve that ellusive ‘net, negative CAC’ 😉
We also used the newsletter to launch & grow a number of ‘simple, profitable businesses’ over the years in our portfolio…
Bookkeping
Content
Staffing
Workflow design
Our long-term equity management firms
and honestly… if you go back to the tapes… probably soo many more.
But, most importantly…
It created the accountability to JUST SHOW UP… EVERY SINGLE WEEK… and write something of value for YOU!
It forced us to sharpen our axe and practice our craft…
Aaaaannnndddd eventually….
We launched Bootstrapper.ai 🎉 which again, thanks to you is on track to leave it’s ‘bootprint’ on our ecosystem in a very BIG way.
So….
….without further ado…
Simple Profits is now Bootstrapper.
Not a pivot.
Not a rebrand for the sake of optics.
This is a structural decision of the same kind we write about every week.
The old name described a tactic.
The new name is a commitment.
And here is what that commitment looks like inside your inbox going forward:
Every edition ships with at least one thing you can apply this week.
Not a framework to study.
A move to make.
Real breakdowns of how bootstrapped businesses generate margin, protect it, and compound it over time.
With numbers where possible. Without the gloss.
Founders who have been through a sale, a transition, or a liquidity event share what actually happened inside the deal.
The structure.
The terms.
What they would do differently.
We’ve always been building toward this.
You were already reading it.
Now we have the right name for it…
Welcome to Bootstrapper.
— Chris Sacchinelli
P.S. If this is the kind of thinking that lands for you, forward it to one founder who needs ownable systems more than another hack.
If you enjoy this content, then let’s connect on LinkedIn.
We actively invest in B2B service and SaaS businesses who prioritize building a long-term sustainable business.
