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5 problems new business owners face (and how to fix them)
Your troubleshooting guide for when problems arise
Ben Kelly
October 21, 2025
This email is Part 6 of a short series covering everything you need to do after buying your first business.
You can read the first five parts here:
In this series, I’ve given you my ultimate guide for your first year as a business owner.
And while it’ll do a great job preparing you for what’s to come, it’s also true that things rarely go 100% according to plan.
To close out this series, I’m sharing how to handle 5 of the most common problems new owners face, starting with…
A key employee quits in the first 90 days
If this happens, start with an honest exit interview to find out why they’re leaving.
Then, immediately promote or hire a replacement, and use this as a wake-up call to cross-train your team so that no single person is irreplaceable.
Finally, revisit your retention strategy to make sure you’re paying competitively, and that your employees feel valued.
Revenue drops after you take over
First, diagnose the cause by talking to customers, employees, and vendors. Is it seasonal? Did the seller inflate numbers? Are clients leaving because of the ownership change?
If clients are leaving, call them personally and ask why. Sometimes it’s fixable (poor communication during transition), sometimes it’s not (personal relationship with the seller).
Either way, accelerate your marketing efforts now to replace lost revenue, and don’t wait months to launch new campaigns.
(It’s also worth reviewing operations to make sure your service quality isn’t slipping. And if it is? Fix those issues immediately.)
Maybe equipment is broken, key contracts are expiring, or there’s a pending lawsuit you didn’t know about.
Review your purchase agreement for representations and warranties, as you might have legal recourse.
Talk to your attorney immediately, assess the financial impact, and determine if it’s something minor or if it fundamentally changes the business value.
If the seller lied or omitted material information, pursue recourse through escrow holdbacks or legal action.
A cash flow crisis
If you’re running out of money faster than expected, immediately cut non-essential expenses. Delay equipment purchases and negotiate better payment terms with vendors.
Next, accelerate collections. Call every client with outstanding invoices and get paid now.
If you need breathing room, consider a line of credit or short-term financing to bridge the gap while you fix the underlying issues.
And finally, revisit your pricing (you might need to raise prices sooner than planned).
Getting overwhelmed and burned out
First, acknowledge that this is normal, and that many new owners feel this way in months 2-4.
Go back to the basics from this series and ask yourself: Have you documented systems? Delegated effectively? Hired a GM?
If not, start there. Identify the 3-5 tasks only you can do, and delegate everything else to your team.
And give yourself some grace here! You’re learning an entirely new business while trying to improve it at the same time.
It gets easier
Problems are inevitable when you buy a business.
The difference between success and failure is how quickly you identify and solve them.
Stay calm, act decisively, and lean on the fundamentals from this series - you can do this.
Thanks for following along for this series! I hope this roadmap helps you build something incredible.
If you’re looking to buy your first business, I occasionally share deals with subscribers when I find them.
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Onward,
— Ben Kelly
