Free download: The 8-Figure Exit Guide
The exit playbook for owners of $5M–$50M companies and businesses with $1M+ in EBITDA. Get your free copy →
Labrador retrievers are praised for their intelligence. They’re often employed as guide dogs, and some are even trained to detect early signs of medical conditions.
Our lab, Tazo, on the other hand, nearly drowned trying to drag a buoy anchored to the ocean floor back to shore.
Our good boy met his match with a bad buoy ;)
But I’ll give Tazo this. He showed incredible grit.
Despite the fact that this buoy was anchored to the ocean floor, he kept on swimming. His internal tugboat engine was redlining but, as Dory once said, he had to just keep swimming. If we factored the time he spent on this conquest in dog years, he spent a significant % of his life on this quest, to no avail.
But why am I sharing this story?
Because you, reader, are in the midst of your own doomed tug-of-war against a personal buoy. Less literally, your buoy is most likely a side project you’re trying to get off the ground, a difficult employee you’re trying to help improve, or a failed relationship where the original flame has turned to tiny embers that you continue to pathetically stoke with all your remaining breath.
Okay, that got a bit dark, but it’s the truth.
The entrepreneurship community, especially, loves to romanticize this David vs. Goliath story in our heads, as if grit, persistence, and determination will always enable us to drag our personal buoy to shore (we all got that dawg in us, after all).
Those are useful qualities when you’re working on something that is actually possible.
But sometimes you’re trying to push a 10,000-pound boulder with your bare hands.
It’s the customer you’ve chased for years who will never sign. The service line that has never made money, but you keep it around because it’s “strategic.” The job you won’t delegate because nobody does it as good as you (in your mind).
The reality is that most businesses have an anchor at their feet and that anchor is you.
It doesn’t matter if you get up at 4 AM and take an ice bath, work 100+ hours a week, or build another fancy spreadsheet with a great (fictional) forecast that gets you to your end state.
If every decision still has to go through you, all that extra work might just be hiding the problem.
I’m not saying quit every time something gets difficult. Building a business is hard, and plenty of things are worth fighting for. But holding on because you’ve already spent years holding on isn’t much of a strategy (sorry, Tazo).
And if you want to sell your business one day, a buyer is going to have some questions about the things you’ve been holding together yourself.
When they see your 100+ hour workweek, they’re wondering who will do that work when you’re gone and what it will cost to replace you. If you’re also the one keeping your biggest customer happy, they’ll want to know whether that customer is going to stick around.
The same goes for that “strategic” service line. If it consistently loses money, a buyer will want to know why it’s still there and what happens to the rest of the business without it.
Those questions can turn into a lower offer, tougher deal terms, or a buyer walking away. Not exactly the reward you were hoping for after all those early morning ice baths.
The good news: you don’t have to fix everything all at once. Start with one thing. Have someone else manage a customer relationship. Get an honest look at what that service line earns. Figure out which decisions actually need to come through you.
Start asking: what is your business worth without you involved? If the answer is, “Oh we would be completely f***”**
Then you have some work to do. You can get started on this (for free) using our Exit Audit tool. It gives you a free valuation + scores your business on how ready your business is for buyers. Get started for free HERE.
founder fitness
4 rounds:
10 goblet squats
10 push-ups
12 kettlebell swings
30-second plank
Rest 60 seconds between rounds. Use bodyweight squats or knee push-ups if needed.
founder challenge: build a simple scorecard
I recently started using Claude Artifacts, and we built a custom, real-time dashboard in minutes. This would have taken weeks before - there are really no excuses anymore.
Your challenge: pick three numbers that matter to your business (revenue, gross margin or overdue receivables, for example). Ask Claude to help you build a dashboard using your data. The lowest hanging fruit is exporting your financials out of Quickbooks and have Claude build you a custom dashboard like a high-end consultant.
After, set a target for each KPI, review them with your team, and pick one that needs improvement this week.
Want a full week of these? Try the free 7-day founder fitness challenge →
deal breakdown
$8M for a landscaping company making $1.8M a year? In this video I break down what I’d pay and the one sentence in the listing that would worry me 👇
Curious about the Benchmark Offer for your business? Get an answer in 48 hours by booking your discovery call here
my plugs
Schedule a confidential call to discuss selling your business.
Book your free Exit Audit: We guarantee we’ll find hidden profit in your business. Start here →
Create your Buyer Profile: Unlock better deal flow by creating a free profile on Breakwater’s deal portal HERE
Subscribe to my YouTube Channel
every second counts