Congratulations! You built a successful business through years of hard work and strategic decision-making. Then came the sale, which should feel like the ultimate victory lap. Yet according to the Exit Planning Institute, 75% of business owners regret selling within just one year.

Why? Because selling your business isn’t just a transaction but a transformation. One day, your wealth is embodied in a business you control intimately. Next, that same wealth is held in accounts managed by unfamiliar faces using terminology you may not fully understand. Your life’s work transforms from something you actively built to something you must now protect and grow differently.

The skills that have made you a successful entrepreneur remain valuable but must be applied in new ways. Just as you built a team to run your business, you now need to build a team with the right advisors who work together toward your goals.

The entrepreneur’s dilemma: common pitfalls after the sale

Even successful business owners can encounter challenges after transitioning from running a company to managing personal wealth. 

• Identity crisis: Underestimating the void created after years of deep involvement in their company and failing to develop a personal vision for “what’s next” beyond financial goals
• Poor tax planning: Missing opportunities to structure the sale and subsequent investments tax-efficiently
• Rush to reinvest: Hasty decisions can lead to inadequate diversification and an overweighting of trendy industries
• Inability to let go: Staying overly involved post-sale, impeding the successor while neglecting your personal financial responsibilities
• DIY wealth management: Assuming business acumen automatically translates to investment expertise
• Lifestyle inflation: Rapidly accelerating spending without sustainable long-term planning

The most effective way to avoid these common pitfalls is to assemble a team of advisors who can provide comprehensive guidance through this significant transition.

Team synergy in action: how coordination creates value

We believe doing it alone or relying on disjointed advice can leave critical gaps in your strategy. When your advisory team collaborates effectively, they can potentially create outcomes far superior to what any individual advisor could achieve alone. Consider these common post-sale scenarios:

Strategic Charitable Gifting

A business owner wants to establish a meaningful charitable legacy while managing the tax impact of their windfall. Working in isolation, the accountant might suggest a basic donor-advised fund for immediate tax deduction, while the financial planner might recommend limiting charitable giving to preserve long-term growth. With team coordination, your wealth manager helps you see how much you can afford to gift and identifies vehicles aligned with your passion, your accountant structures contributions for tax efficiency, your attorney ensures proper governance, and your investment advisor creates and implements customized investment strategies – resulting in a plan that aims to magnify impact while optimizing tax benefits.

Real Estate Opportunity 

A business owner identifies a potential real estate investment. Working in isolation, the investment advisor might analyze only the return metrics, the attorney might focus exclusively on liability concerns, the planner may not appreciate the diversification benefits, and the private banker might simply approve or deny financing based on standard criteria. But with coordination, in our view, you can design a well-structured opportunity that potentially balances return potential with risk management, optimal tax treatment, and alignment with broader financial goals.

Family Legacy Planning

A business owner wants to provide for future generations while instilling values. Working in isolation, the attorney might draft standard trusts focused primarily on tax efficiency, the insurance specialist might recommend large policies that may be less optimal than self-insuring, and the investment advisor might manage trust assets without considering the overall strategy. With team coordination, your wealth manager facilitates family meetings about goals, your attorney designs aligned trust structures, your insurance specialist implements integrated coverage, and your financial planner focuses on long-term sustainability, creating a cohesive plan that transfers both wealth and values while adapting to changing circumstances.

Know the Players: Building Your Financial Dream Team

Your financial future depends on assembling specialists who collaborate effectively. Each brings expertise that creates a powerful synergy no single advisor could provide:

Accountants: Tax optimization experts who help structure your wealth to minimize the burden while ensuring compliance. Typically compensated hourly or on retainer.

Attorneys: Legal guardians who provide essential protection through structured entities, contracts, and estate plans. Generally, bill hourly or on retainer for specific projects.

Insurance Specialists: Risk management professionals who help identify, quantify, and transfer specific threats to your financial security. Usually compensated through commissions on products sold.

Private Bankers: Financial concierges who provide access to sophisticated banking solutions and customized credit structures. Typically compensated for keeping assets at the bank and selling financial products.

Investment Advisors: Market specialists who construct and manage portfolios aligned with your risk tolerance and return objectives. Often compensated as a percentage of assets under management or in some cases, through product sales.

Philanthropic Advisors: Impact strategists who transform charitable intentions into meaningful legacy through specialized vehicles and strategies. Compensated hourly, on retainer, or by providers.

Financial Planners: Architects who create roadmaps connecting resources to goals through forecasting and scenario modeling. Compensation varies from flat fees to assets under management to product sales.

Wealth Managers: Investment and planning professionals who integrate and coordinate many of these services into a cohesive strategy. Typically compensated through asset-based fees.

hidden conflicts that can derail your financial future

Understanding potential conflicts helps you make informed decisions.

Compensation-Related Conflicts

• Commission-based models may prioritize higher-fee products over what’s best for you
• Asset-based fees create reluctance to recommend spending or gifting that reduces the fee base
• Transaction-based incentives may drive excessive trading
• Hourly or flat fees can be at odds with achieving performance goals

Product and Service Conflicts

• Proprietary products and kickbacks from outside funds are incentives that may steer you away from better alternatives and often result in higher fees
• Private investments create a structural conflict by locking clients into vehicles that prevent them from switching strategies or advisors when circumstances change
• “Tied selling” makes favorable terms conditional on using multiple services from one provider, potentially foregoing better options available elsewhere for specific needs

bUILDING YOUR WEALTH MANAGEMENT tEAM: a sTRATEGIC aPPROACH

This requires setting clear qualifications, conducting proper interviews, and understanding credentials.

1. Define your needs: Decide between a one-stop shop or independent specialists
2. Get recommendations: Seek referrals from other entrepreneurs who’ve navigated this transition. Ask the current advisors you trust, such as your CPA or attorney, whom they recommend.
3. Interview consistently: Ask each advisor the same questions to effectively compare:
   • What sets your firm apart?
   • What experience do you have with clients like me?
   • Are you a fiduciary? How are you compensated?
   • What other fees would I be charged?
4. Verify credentials: Understand what various designations mean for your situation
5. Conduct due diligence: Research advisors on the Investment Adviser Public Disclosure website

A transformation built on teamwork

Selling your business opens a new chapter requiring the same strategic approach to team building that made your company successful. Take time to deliberately build your financial dream team rather than accumulating advisors haphazardly. Ensure they understand not just their roles but how they fit into your broader vision.

Remember that the same threats that could derail your business – death, disability, divorce, distress, disagreement, and taxes – can also undermine your wealth. But with the right team in place and guided by your leadership, you can navigate this transition successfully.

Your most important job now is not managing the money yourself – it’s building and leading the right team to manage it for you.