The Highlights
Many owners can’t shift away from being Mr./Mrs. Everything, and it crushes their exit multiple.
Grit builds the business, but systems make it valuable.
If you’re the bottleneck, the business is a tough sell.
Real example: the $3.5M company that struggled to find a buyer due to founder-dependence.
The #1 buyer question: Can this run without you?
The Hard Shift
Many business owners think they can sell their business in the same state it was built: relying on quick, top-down decisions, with a hands-on founder driven by grit and gut instinct.
Reality check - the mindset that gets you from zero to $2M+ is the exact thing that will snag your exit trajectory. When you’re building, being scrappy and speedy wins. You make moves in real time and fire-fight. You spearhead every task because you’re bootstrapping. That’s how the business gets off the ground. But when you enter the open market for a sale, it doesn’t reward your sunk time and effort. Buyers reward systems. They’re not buying your late nights or your heroic 7-day schedule.
They’re interested in the machine that runs without you.
And if it doesn’t?
You’re not selling a business. You’re selling your job.
An example of a business owner who suffered this gut-punch from earlier in my career:
$3.5M pet services company:
-The Good: 10+ years in operation. Multiple locations. Stronghold on local market share. Award-winning service reputation.
-The Risks: Weak org chart. Daily Ops ran heavily through the founder (including ad-hoc phone calls from staff to vent about customer issues). Owner still doing payroll, supply runs/orders, hiring, site visits.
-Reason for selling: Burnout (no surprise).
-Interest: Screened over 150+ buyer candidates (Mostly self-funded & Strategics, some PE). Most backed out after pre-LOI due diligence.
-4 offers. All bottom-end of the industry’s multiple range. All with heavy contingencies to account for owner-dependency risk.
Total time to sell: Over 2 years.
It wasn’t a bad business. In fact, it was top-rated in it’s market. But things stalled when it came time to sell. Why? Because the founder hadn’t made the shift to level up, and buyers saw the risk in the workload ahead of them. Great company, weak survivability.
‘I don’t trust someone to run this the way I do’, the owner told me.
If you’ve ever thought or said this, chances are you’ll be the bottleneck that stifles your company’s ascension to the next rung of business success. At a certain scale, usually around the $2M+ mark, you have to shift from doer to designer. Work on building guardrails for new hires to uphold the standards you set, and move on to bigger thinking.
Swap your mentality from ‘this is all me’ to ‘this doesn’t need me at all’.
Above financial strength and growth opportunities, savvy buyers look for one thing: Stability without you.
Can the team run the show and execute on your decisions?
Is there financial flex to reinvest in people and endure a rainy day or two without you having to play double coverage?
Are there systems, or are you the system?
If those answers are shaky, the deal will be too. You’ll get lowball offers and leave lots of value on the table. This is the hardest mindset shift for any founder. For years, they were the business. Every win, every save, every dollar - they made it happen.
But if you want to exit, that can’t be true anymore. You’ve got to pull yourself off the field and run plays from the sideline. Design the strategy, even if you’re not touching the ball.
Buyers will pay a premium for that playbook.
Tangible Takeaways
This shift doesn’t happen overnight. It comes through a series of calculated decisions over time. But if you want to maximize your exit value, these are the moves that matter most:
Build an org chart and delegate key daily ops decisions: Show that the business can run without you. Start by identifying 1-2 key roles you still control, and plan how to offload them.
Financial flexibility: Bring in a fractional CFO or a legit controller. You want financials with breathing room that a buyer can trust at a glance.
Document your core processes: Crucial ops info should live outside your brain. Use Loom videos, SOPs, or checklists. Make it transferrable.
Systematize hiring and the customer journey: If you’re the spearhead, you’ll probably hit a revenue ceiling. Build repeatable processes and hand the reigns over to the A-level players on your team.
Take small steps away → Identify cracks → Fix → Repeat
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