Too many entrepreneurs are ready for failure, but unprepared for success.
A potential client recently reached out with a problem most business owners would envy: his company had taken off faster than expected. Years of late nights and international hustle finally paid off, and his firm had grown into a multimillion-dollar enterprise. But instead of celebrating, he felt unsettled.
He wasn’t worried about cash flow or profitability. His concern? He hadn’t planned for what happens next.
Prepare for Success, Not Just Setbacks
Entrepreneurs often build detailed plans to survive downturns, but few create strategies for managing explosive growth. That oversight can turn a win into a headache.
In this case, his rapid expansion abroad had dramatically increased his company’s value. But with that came questions he hadn’t thought to ask: What if the company gets bought? How do I prepare my family for this kind of wealth? How does overwhelming success affect the inheritance I leave for my family?
He realized that growing a business was only half the job. The other half was protecting what he’d built.
Does your Estate Plan Include Provisions for Paying Taxes?
At first, he figured he had plenty of breathing room under the estate tax limit. The U.S. exemption is about $14 million per person. But with valuations climbing, that cushion shrank faster than he expected.
We discussed ways to ease the future burden, starting with gifting company shares at a discounted valuation, well before any liquidity event. Often, complicated tax planning moves cannot be made at the last minute; they require planning while the company is still growing.
You Can’t Spend Paper Wealth
Most of his assets were tied up in the business, which meant little cash was immediately available. Without a plan for liquidity, many founders find themselves asset-rich and cash-poor at the worst possible moment.
We built a portfolio of conservative, laddered certificates of deposit (CDs) to give him short-term flexibility. It’s money set aside for opportunities, for emergencies, and for something harder to measure, peace of mind.
He didn’t need higher returns. He needed room to breathe.
Success doesn’t remove financial stress. It just changes the stakes.
If your business suddenly took off, would your finances be ready?
So, take the first step now, Get a free Cross-Border Financial Evaluation at www.profile-financial.com/call. Let’s find out if, and how, we can help you stay ahead.
Douglas Goldstein, CFP® is the director of Profile Investment Services, Ltd. www.Profile-Financial.com. He is a licensed financial professional both in the U.S. and Israel. Call (02) 624-2788 for a consultation on how to set up your American assets to meet your financial goals. Securities offered through Portfolio Resources Group, Inc. Member FINRA, SIPC, MSRB, FSI. The opinions expressed are those of the author and not those of Portfolio Resources Group, Inc. or its affiliates. Neither PRG nor its affiliates provide tax or legal advice.
Published October 22, 2025.