Don’t Sell Your Business Without These 4 Core Advisors — One Saved My Client $1.8 Million

Selling a business is one of the most important moments in an entrepreneur’s journey. Over the years, I’ve learned that the best outcomes come when founders build a team of experts early, specifically in four key areas: tax planning, legal preparation, wealth management and value growth. Understanding what each specialist brings and asking the right questions can make a huge difference in the sale price and ensure the process goes smoothly

Tax advisor: Protecting the proceeds

I’ve seen firsthand how costly taxes can be if you don’t plan ahead. One of my clients in the technology space was facing a potential IRS hit of 65% of his sale. By coordinating with a wealth manager and my value growth team, we were able to save him $1.8 million. That experience reinforced for me that pre-sale tax planning is critical — the time to strategize is before the sale, not after

When I evaluate tax advisors with clients, I ask how will you coordinate with my other advisors and can you help with pre-sale tax planning that often requires one to two years of preparation. These questions ensure the advisor can protect the business and its owners effectively.

Legal advisor: Getting it in writing

I always tell founders that it doesn’t matter what you agree to verbally — it matters what’s written in the contract. Legal advisors are essential to make sure everything is clearly documented and that liability is minimized after the sale

When looking for a legal advisor, I suggest asking about their negotiating style and the types of issues that have caused deals to fall through. In my experience, the right advisor knows when to push and when to step back and they can help prevent common pitfalls before they become major problems

Wealth advisor: Making the sale last

I’ve seen founders sell their company for $1 million and stretch it into decades of financial security with proper planning. I’ve also seen others with the same sale amount run out of money in just a couple of years. The difference is a thoughtful exit strategy

When I work with clients on wealth management, I focus on making sure the advisor’s investment philosophy matches the founder’s risk tolerance and life goals. I also emphasize the importance of coordination with tax and estate planning attorneys because wealth management doesn’t exist in a vacuum—it intersects with every part of the exit plan

Value advisor: Growing your business before the sale

A value advisor helps a company grow in worth over time. For example, a founder might want $5 million from a sale, but the business is only worth $1 million. A value advisor helps devise and execute a plan to reach that goal. Once the valuation target is hit and the founder is ready to sell, a broker can step in to find a buyer and negotiate the deal

I always ask potential value advisors how they determine valuation, how they will help grow the business over time and what exit options they can support. These questions ensure that the advisor isn’t just giving estimates —they’re providing a roadmap to achieve real results

Warning signs when choosing advisors

From my experience, there are a few red flags that can help founders avoid bad choices. Unrealistic promises, poor communication or self-interest are all signs to look out for. I’ve learned that the most successful exits come from advisors who coordinate well, communicate clearly and focus on the founder’s goals rather than their own convenience

Start preparing early

I tell founders to start gathering legal and financial documents and minimizing expenses as soon as possible. It’s also important to start relinquishing control so buyers know the business can run without the founder. Planning ahead gives you more time, more options and ultimately a higher sale price

From my perspective, the key to a successful exit is assembling the right team, planning strategically and taking action long before the sale. That way, all your hard work pays off in both financial reward and personal legacy

Selling a business is one of the most important moments in an entrepreneur’s journey. Over the years, I’ve learned that the best outcomes come when founders build a team of experts early, specifically in four key areas: tax planning, legal preparation, wealth management and value growth. Understanding what each specialist brings and asking the right questions can make a huge difference in the sale price and ensure the process goes smoothly

Tax advisor: Protecting the proceeds

I’ve seen firsthand how costly taxes can be if you don’t plan ahead. One of my clients in the technology space was facing a potential IRS hit of 65% of his sale. By coordinating with a wealth manager and my value growth team, we were able to save him $1.8 million. That experience reinforced for me that pre-sale tax planning is critical — the time to strategize is before the sale, not after