In partnership with
Welcome back, Owners.
Before we jump into today’s issue of Bootstrapper….
The biggest mistake you can make today is not building your holiday creator program now.
Here's the thing: you can't build one in November and expect it to work.
The strongest programs get built 90 days before peak holiday shopping season.
At the end of those 90 days, you'd have:
The right partners by your side
Commission strategies that actually work for you
Relationships that drive real holiday performance
To help eCommerce brands do exactly that, Levanta created The 90-Day Holiday Sprint, a proven framework to:
Build a holiday-ready affiliate and influencer program before demand hits
Structure commissions that compete for creator attention without hurting margin
Turn Day 30, 60, and 90 checkpoints into a program that's ready to scale for BFCM
Don’t wait for the holidays to build the program you’ll wish you already had. Your 90-day countdown starts now.
This week I sit down with Amit Kadosh who bootstrapped and exited a restaurant takeout marketplace, built in 2020 and sold in 2024.
He spent nine months chasing investor-defined vanity metrics before realizing nobody could actually define what "traction" meant. Once he stopped building for VCs and started reading his own usage data, he found the real business hiding inside the one he thought he was running.
We get into how he scaled to nearly 900 restaurants and then the story turns. War breaking out in his home country, an injury from an anti-tank missile, and a 72-hour take-it-or-leave-it offer collided into the fastest, least negotiated exit of his career.
Most growth problems get treated as effort problems.
Pipeline's slow, so add reps. Leads aren't converting, so add spend.
Usually the actual issue is one specific step in the process and no amount of effort around it fixes it.
THE CORE INSIGHT
Every process has a single component that caps total output, regardless of how hard the team pushes.
Find that component and remove it, and growth stops being linear.
KEY TAKEAWAYS
Undefined targets are not metrics. Investors who can't define a number are asking for compliance, not tracking a metric. If you can't get a specific target, stop chasing it.
Usage data reveals the real value. Your original pitch and your actual value are often different businesses. Pull usage data and look for the customer segment behaving in a way you didn't design for.
A bottleneck usually has two parts: access and payment. Remove the payment requirement first and the access problem often becomes easier to solve.
Every completed transaction that reaches a non-customer is an unused distribution channel. Put a message at that exact touchpoint instead of relying only on outbound.
THE MECHANISM
Take a sales process that requires two things to close: technical access and payment collection.
Separate them.
Defer payment collection to a later stage, and the process that used to require a manual sales conversation can often run without one. The ceiling moves and the shape of growth curve changes.
ONE THING TO DO THIS WEEK
Pick one process that's slowing your growth in the business.
Write down every step it currently requires, in order.
Now look at that list and find the step where you collect payment or get formal approval. That's usually the slowest part.
Ask: could this process start and run without that step, and happen later instead of first?
If yes, move it. Test the shorter version on your next five customers and see what changes.
OWNABLE IDEA
Local events happen every week and nobody is capturing them well. Organizers want quality photos fast, attendees want to buy them without friction.
You show up, shoot the event, and deliver a branded online gallery same-day where attendees purchase individual photos and packages directly.
$485 average revenue per event
$170 cost per event
$1,940 organizer LTV based on 4 events per year over 2 years
Path to $8,500 per month covering events part-time
A camera, a mobile gallery tool, and a QR code at the door is enough to run your first ten events solo.
How would you land your first 6 events?
EXIT LISTING OF THE DAY
Celebration Moments Event Planning - Charleston, SC
Asking: $485,000
Revenue: $620,000
Profit: $148,000
85-100 events per year.
$6,500 average contract value.
24% profit margins.
40+ preferred vendor relationships.
3 full-time planners plus part-time and seasonal staff already in place.
Owner relocating to care for aging parents - 8 years of brand equity, a 4.9-star reputation with 200+ reviews, and access to Charleston's premier venues all transfer with the sale. Weddings carry 60% of revenue, corporate events 30%, giving the business two distinct demand cycles instead of one.
What would you prioritize first as the new owner?
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.
