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Welcome back, Owners.
Before we jump into today’s issue of Bootstrapper….
Most founders delay forming their LLC longer than they should.
LegalZoom handles the setup - forming your LLC, incorporating, filing a DBA, and keeping you compliant with annual reports and registered agent service.
So you don’t have to figure out state requirements at midnight…
Do it once, do it right, move on.
Last week I sat down with Justin Gelinas, who walked away from a Silicon Valley infrastructure job after an injury forced him to stop, and built Bright Light Immersive from a fractured partnership into a company trusted by some of the biggest brands in the world.
We get into how a bootstrapped agency survives net-90 payment terms, how a side software product ended up mattering more than the agency itself, and how a years-long client relationship quietly turned into an acquisition.
We also talk about what actually happens after the deal closes, the part nobody prepares you for, and how it led straight into his next company.
A business lands its biggest contract yet.
Team's booked.
Everyone's excited.
Six weeks later, payroll is tight and nobody can explain why.
The contract wasn't the problem.
The payment terms were.
THE CORE INSIGHT
Cash flow management has nothing to do with how much revenue is on the books. It's entirely about timing.
A business can be profitable on paper and still run out of cash, because profit is what you've earned and cash flow is what you actually have access to right now. The bigger the client, the longer the payment terms usually run. Which means the contracts that look the most impressive are often the ones creating the most pressure.
KEY TAKEAWAYS
Before signing any contract with extended terms, calculate how many weeks of payroll and overhead sit between delivery and payment
Negotiate payment terms before the contract is signed, not after work begins — leverage disappears once you're dependent on the relationship
Reconcile cash flow weekly, not monthly. Monthly reporting shows you the shortfall after it's too late to act on it
Build internal efficiency, not lower prices, as your competitive edge. Faster delivery protects margin.
Watch for early signals of a market shift and reposition before the shock hits
ONE THING TO DO THIS WEEK
Pull your current receivables and payables into one view, and calculate the actual dollar gap between when your next big invoice gets paid and when your next payroll runs.
OWNABLE IDEA
Ownable Score: 73 / 100
Small businesses know they're a target but don't have the budget or headcount for an in-house security team.
You become their outsourced security department - running assessments, standing up monitoring, and keeping them compliant on a monthly retainer.
$750 per client per month
$200 cost per client
$18,000 LTV based on 24-month retention with annual contract increases
Path to $15,000 per month at 20 clients, No software needed to start. A proven assessment checklist, a monitoring dashboard, and a vetted network of security tools is enough to land and run the first clients.
How would you land your first 5 clients?
EXIT LISTING OF THE DAY
Clearwater Tech Solutions - Boise, ID
Asking: $197,000
Revenue: $427,000
Profit: $89,270
Multiple: 2.2x
47 recurring clients.
85%+ annual retention.
68% recurring revenue.
Owner retiring after 38 years - decades of client documentation, vendor relationships, and processes ready to transfer.
Dell and Microsoft vendor partnerships, deep roots in the Treasure Valley business community, and clear runway into cloud migration and cybersecurity consulting.
A near-40-year track record at under 2x revenue is rare in this space.
What would you tackle first after buying Clearwater?
Join the wait-list for Bootstrapper ONE
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.
