Welcome back, Owners.
This week I sit down with Brandon Harris, who built a bootstrapped sports media company from a collection of social handles and grew it to a $54 million exit with a publicly traded European acquirer.
We get into the deal structure, the earnout that performed differently than it looked on paper, and what the other side of an exit actually feels like when the brand you built is no longer yours.
Most founders think the exit happens at the negotiating table.
It does not.
It happens in the decisions made years earlier - about assets, structure, and how revenue compounds.
WHAT ACTUALLY WORKS
Entity structure determines deal structure. An LLC often forces an asset purchase, which favors the buyer. Know this before you need to.
Earnouts tied to metrics outside your control are not deferred compensation. They are a discount on your headline number.
Run a parallel process. Talking to investors and acquirers simultaneously is how you keep pricing leverage when conditions are not in your favor.
Revenue that funds new owned assets compounds. Revenue that only covers costs does not.
The deal process is depleting. Months of diligence affect decision quality late in the negotiation. Prepare for it.
ONE THING TO DO THIS WEEK
Pull up your entity structure and book 30 minutes with a transaction attorney.
Ask one question: how would this be treated in an asset purchase versus a stock purchase at my current revenue level.
That conversation is worth more than most exit planning you will do this year.
01 — OWNABLE IDEA
Home Cleaning Subscription Service Ownable Score: 74 / 100
Build a recurring home cleaning business on retainer - targeting busy professionals and families who want consistent, reliable service without managing it themselves. You become the one operator they never have to think about.
$180 per customer per month
$55 cost per service delivery
$3,240 LTV based on 18-month average retention
Path to $10,000 per month at 56 active customers
No software needed to start.
A phone, a cleaning checklist, and three reliable contractors is enough to run the first ten clients manually.
Acquire through neighborhood door-knocking and local referrals.
Standardize delivery before you scale headcount.
How would you fill your first 10 cleaning clients?
02 — SIMPLE BET
Rush Job Premium Pricing Test For service businesses taking project work
Hypothesis: clients with urgent timelines will pay a 50% premium for turnaround under 5 business days, because their pain of waiting outweighs the cost of the fee.
Run it in 5 steps over 14 days:
Add the rush pricing rule to any project requested with less than 5 business days notice
Update your proposal template with a clear rush fee line item
Brief whoever handles intake on when to apply it and how to explain it
Log every new inquiry with timeline, quoted amount, and whether rush pricing applied
Follow up within 24 hours on every rush quote to close faster
Success metric: average project value up at least $20 with no meaningful drop in close rate.
Did you charge more for urgent work this month?
03 — DEAL OF THE WEEK
Meridian Engineering Consultants Austin, TX
Asking: $1,736,000
Revenue: $3,247,000
Profit: $578,000
Multiple: 3x
27 employees.
8 licensed professional engineers.
Founded in 2002.
40% of revenue from municipal contracts with automatic renewal clauses. Project backlog extends 4 to 6 months forward at any given time.
This is a cash-flowing professional services business with two decades of relationship equity baked in. The municipal contract base is the real asset here - those relationships take years to build and are nearly impossible to replicate quickly.
Owner is moving into renewable energy and wants a clean transition. Six months of support included. Financing available.
What kills most professional services deals?
If your books are more than two weeks behind, you are already paying the tax. You just cannot see it on a P&L.
Books closed by the fifth.
ILTEM credentialed.
Real human on the other end.
Starts at $500 per month, but first 30 days free for Bootstrapper readers.
Are you currently working with a bookkeeper?
You've been showing up.
Let this be my way of showing up for you.
— 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.
