The dialogue and summary below are for informational purposes only. The opinions expressed are those of the participant only and do not constitute investment advice or a solicitation to buy or sell any security. Past performance is not indicative of future results. Investment banking services offered through Crewe Capital, LLC, member FINRA/SIPC.

Building a successful business and successfully exiting one require two very different skill sets. Most entrepreneurs spend years focused on growth, operations, and the challenges directly in front of them. But when the time comes to sell, many discover that decisions that can materially affect an exit often need to be considered well in advance.

Crewe Capital founder Mike Bennett recently joined Chris Naugle on the Money School Elite Podcast to discuss the realities of preparing for a business exit, managing wealth following a transaction, and why owners should begin thinking about both sides of the equation long before they’re ready to sell.

Their conversation covered everything from reducing risk within a business and assembling the right advisory team to tax considerations, family offices, and the purpose of wealth after an exit. Here are some of the key takeaways.

1. The Best Exit Strategies Start Years Before the Sale

One of the biggest mistakes a business owner can make is waiting until they’re ready to sell before preparing the company for a transaction. Selling a business can be a multi-year process, yet owners often reach the decision to sell after years of running at full speed, when they’re burned out and ready to move on as quickly as possible. At that point, issues that could have been addressed over time can become obstacles to a transaction.

Financials may need to be cleaned up, personal and business expenses may be mixed together, revenue may be heavily dependent on one customer, or the founder may still be responsible for too much of the company’s day-to-day operation. Each of these factors can create additional risk from a buyer’s perspective and may affect how a potential transaction is evaluated. Beginning the planning process earlier gives owners more time to identify potential issues and consider how they might be addressed before going to market.

2. Buyers Are Evaluating More Than Financial Performance

A strong business isn’t defined by revenue or profitability alone. Buyers also evaluate the risks that could affect the company’s ability to perform following a transaction. Customer concentration is one example. A company may be highly profitable, but if a significant percentage of its revenue comes from a single customer, a buyer will likely consider what could happen if that relationship changes. Founder dependence can create a similar concern if the owner holds key customer relationships, makes every major decision, and remains central to daily operations.

A capable management team, established systems, reliable financial reporting, and clear organizational structure can help potential buyers evaluate how the business may operate independently of its founder. Growth matters too. Owners should be prepared to articulate where future growth opportunities may exist, whether through organic expansion, new markets, additional products, or acquisitions. The goal is to give potential buyers the information they need to evaluate both the business today and its opportunities and risks going forward.

3. The Right Advisors Matter

The team surrounding an owner during a transaction can have a significant impact on the process. One area Mike emphasized is legal counsel. M&A is a specialized area of law, and an attorney who is experienced in general corporate work may not necessarily have the transaction experience needed for a complex sale. The same principle applies across the advisory team. Investment bankers, attorneys, CPAs, wealth advisors, and estate planning professionals each bring different expertise and responsibilities to the process.

Ideally, those professionals aren’t meeting for the first time after a letter of intent has been signed. A coordinated advisory team can help an owner consider the transaction within the context of broader business, financial, tax, and estate planning objectives.

4. Don’t Stop Running the Business While You’re Selling It

Preparing and negotiating a transaction can become a second full-time job, creating the risk that an owner becomes so focused on the sale process that the underlying business begins to suffer. If revenue or profitability declines during a transaction, buyers may reevaluate the business and the terms they’re willing to offer.

This makes a capable leadership team particularly important during an exit. The business still needs to execute while ownership and advisors manage diligence, negotiations, and the many decisions involved in a transaction. Until a deal closes, running a strong business remains the priority.

5. Preparing the Business Is Only Half of the Exit

For many founders, a significant portion of their net worth is tied to their company. A sale can transform years of concentrated business equity into personal liquidity, creating an entirely new set of financial considerations. Tax considerations, including potential Qualified Small Business Stock (QSBS) eligibility, as well as estate planning, asset protection, and charitable strategies, should be evaluated well in advance of a potential transaction. Eligibility for particular tax treatments or planning strategies depends on individual circumstances and applicable laws and regulations.

Beginning these conversations earlier can provide owners with additional time to evaluate the strategies and options that may be available to them. That planning may include tax considerations, estate and legacy goals, investment strategy, philanthropy, and how the proceeds of a transaction could support the owner’s family over the long term.

6. From Creating Wealth to Preserving It

During the years spent building a company, entrepreneurs are often accustomed to taking concentrated risks in pursuit of growth. Following an exit, their priorities may look very different. For families that have already accumulated significant wealth, the focus may shift toward preserving capital, managing risk, and planning for how that wealth will support current and future generations.

This is also where a family office model can play a role. Family office models are designed to coordinate multiple aspects of a family’s financial life, which may include investment management, tax and estate planning coordination, private investments, philanthropy, and other services depending on the family’s needs and the services offered by the firm. Rather than considering each financial decision in isolation, the various professionals advising a family can work together around a common set of goals.

7. Deciding What the Wealth Is For

The final consideration when preparing for an exit has little to do with valuation multiples or tax strategies. It’s deciding what you ultimately want the wealth you’ve created to accomplish. Mike’s perspective on that question has been shaped in part by his own experience, from facing homelessness as a child to eventually building Crewe and advising families with significant wealth.

Financial independence can provide greater control over your time, the ability to support the people and causes that matter to you, and opportunities to think more intentionally about the legacy you want to leave. That philosophy has also helped shape Crewe’s approach to philanthropy. Through the Crewe Foundation, more than $66 million has been contributed to charitable causes.

For founders, selling a business may be the culmination of decades of work. But preparing for an exit isn’t simply about the transaction itself, it’s also an opportunity to think carefully about what comes next. Those conversations are often most valuable when they begin long before you’re ready to sell.