Courtney Williams would never tell a client to sell the family farm. But that's just what one did, sort of. He liquidated a portion of the family's land when their business interests hit a rough patch. A corporate tenant had broken a lease on a commercial building and the family had come dangerously close to losing a credit line.

For Williams, clients' decisions to shore up assets is less about following a cut-and-dried road map and more about the ability to see their personal holdings and their businesses at once as she advises her clients on both.

In this case, the clients had closed their family distribution business after getting an offer to rent their building. The client, whose children weren't interested in the business, were close to retirement. So they accepted the offer and leased the building.

At first, the rental income supplemented their retirement. But when the tenant broke the lease, they could not find replacements quickly and began siphoning income from their line of credit. They needed to shore up that line and with the farm holdings free and clear, Williams knew that made the most sense.

"That's all in the relationship of having both the consumer and the commercial side of their business," says Williams, vice president of private client services with Nashville-based Avenue Bank.

Williams says instead of issuing mandates, she instead frames questions as scenarios where there are never enough resources. "I turn it into, 'What are you guys willing to give up on the personal side to increase the cash flow and have cash reserves for the business?' I don't tell them what to do," she says.

Bank advisors often work as managers of a client's personal wealth, of course. But by also advising on commercial interests, they can help guide small business owners toward the most stable financial options for their companies. In doing so, they also can offer a unique perspective on options that a single-view advisor may not be able to match.

From refinancing a struggling business to setting up an equitable divestiture plan for a long-time family firm, bank advisors who handle a family's financial holdings as well as their business concerns can increase the trust between themselves and their clients - as well as their own bottom lines.

"Sometimes a personal relationship carries through to the business," says Paul Stetter, first vice president and financial advisor with Fulton Financial Advisors, part of Fulton Bank in Ephrata, Pa.

More advisors are looking to branch into this niche as it represents an attractive way to grow their own businesses, say experts. While some advisors will partner with other professionals when advising small business owners, others are asking their own companies for more training in this area, like learning the basics of an S-corporation, for example, or delving into the nuances of tax implications specific to businesses, says Sophie Schmitt, senior analyst with the wealth management division of Aite Group in Boston. "There aren't enough advisors who understand the challenges of the small business side and who are really able to help," she notes. "They want to be able to advise their clients on both the personal and business."

The Personal Touch
Fulton's Stetter is well attuned to this perspective and has put his skills to use with many of his clients. For example, two brothers, restaurateurs in his area, wanted to expand. A meeting on Labor Day 2010, before Stetter's own family picnic, was called to see how the clients could raise additional capital.

As owners of a successful steak house, opened four years earlier, the two now wanted to convert an old diner into a seafood restaurant as business was booming for them even during a rocky economy.

Stetter looked at how the two could restructure some business loans to raise capital for the expansion. But he then examined their personal investments, too, dissecting whether capital could be pulled from their home residences or if they should consider cashing in a life insurance or a 529-college-savings plan.

Knowing that one brother had a daughter yet to enter college, Stetter advised against touching the 529 plan. Instead, the brothers opted for a floating-rate loan based on their joint commercial holdings. And today, those are now at 2% below the fixed rate of a standard commercial loan, Stetter notes proudly. "They're making out," he says. "It was a big gamble to start a middle-end seafood restaurant in this economy. And they have done very well."

Being able to walk the personal and business side with dexterity is critical when working with small business owners, say experts. That's because their financial setup is unique, with a small business sometimes involving family, and almost always because the company has been nurtured and grown directly by the investor. It's not a Fortune 500 firm with shareholders. Here, there's usually one shareholder-the client.

David Schehr, research director with the Stanford, Conn.-based Gartner Industry Advisory Services, notes that a 35-year-old employee with a goal of retiring at 62 requires a tactical approach of increasing 401(k) holdings and factoring in goals and allocations. For a small business owner, the financial complexities grow as there isn't that clear set of parameters to follow that many employees or senior executives at large corporations can usually follow.

"The line between the business and personal gets very blurry with small business owners," says Schehr, who covers the banking and investment services vertical with Gartner. "When they get to the right age, they often start to wonder how do they monetize their business. Should they sell to an employee or investor? How to structure it? It's not the kind of thing where you can find a software package with all the answers in a neat little box. This requires an art as well as a science. It's a skill set that a typical banker or bank advisor may not have."

It's a Family Affair
Jeffrey Getty would agree. As the senior wealth specialist in business advisory services at KeyBank in Pittsburgh, Getty often works with business owners as they consider the legacy of their companies. Sometimes that means selling to an outside party and retiring. Other times, it may mean structuring a solution so the family can inherit the business and keep it running. This may ultimately be a business decision, but to Getty there's always a personal element.

"I don't ever tend to split the personal and business financial worlds because they're so intertwined for small businesses," says Getty. "We often use the phrase 'family financial enterprise' when talking with clients because it's almost impossible to separate the two. And when I meet with a new client I try to get them on board with that psychological view."

Early conversations with new clients can sometimes start with questions just on cash flow. Getty will want to know how much a client is comfortable taking out of the business without harming its bottom line in order to create assets that can be protected for a client's future. Depending on the business, that amount can range, he says, from $50,000 a year to $5 million.

But within that first meeting, there's often an open dialogue about family concerns and what a client might want to happen with their company in a perfect world. When the husband runs a business, Getty brings the wife in early to these conversations as well as children and grandchildren, depending on the client's stage of life.

Even though Getty is a tax attorney, conversations, particularly around the legacy of a family business, require a personal touch as these topics can trigger an emotional response. Sometimes children expect to inherit a business equally-but one child is more integrated than another or has put in more time, he says. Getty's job then is to listen to his client's concerns and help them make sound financial decisions for themselves as well as their business.

"The whole concept of fairness permeates the space," he says. "I have three kids and in my mind, all things being equal, I want to leave things to them equally. I understand that. But in terms of a business, it's not always healthy to do this."

Getty will prep his clients well in advance of decisions surrounding a family inheritance and ownership stake in a company.

Still, things can quickly take a left turn. He recalls one instance where he walked into a prearranged family meeting just after a father had told his children that the sons could be in the business, but not the daughters. Getty had not known about decision, or been forewarned. The father then introduced Getty and left him to field questions from the bewildered family.

"I learned that even in a disaster meeting where people are shocked like that, we can start working and have a dialogue that doesn't end in screaming," he says. "If that decision was made, it's made. But I also knew the father, and could explain that I knew he wanted an equalization of assets. I knew he would pull assets that wouldn't hurt the operations of the company, but still give significant growth potential to the daughters in the room."

Some clients would rather just step out of a business and sell it-but feel a sense of responsibility to hold on to a company for children or employees who have been with a firm for so long they feel like family.

Fulton's Stetter has a client who has been trying to sell his heating and air-conditioning enterprise for the past two years. At 68, he would like to retire, but simply closing the doors instead of finding a buyer would mean his employees would lose their jobs.

But because he owns the land around the business as well, he has more options, says Stetter. One includes finding someone to buy the company-but would keep the client on as the landlord, at least until the new owner had enough cash reserves to buy the client out in full.

"The wife just wants out," says Stetter. "And they want to start traveling. But by leasing the land they could create some extra income. And that's a little pension in some respect."

Then there are clients who wish they could sell, but feel responsible for the next generation.

Rhonda Arnett, a senior financial advisor with Columbia State Bank in Tacoma, Wash., has a client in his fifties who would like to wind down, retire and sell his large construction company. His young son and a cousin have expressed an interest in buying the business-yet aren't in a position to do so now. The dilemma is that Arnett's client is having to infuse the company with personal capital to keep it running, and is likely going to have to continue doing so, given a down economy. If family wasn't interested in running the business, the client would have closed it long ago.

"So they're keeping it running for goodwill," says Arnett. "Particularly for those who have been sitting on a lot of cash, does it make sense to keep throwing money into a business when in the long-term it may not [be profitable to do so?]"

It can be difficult for business owners to realize that passing their company to family may not be the best outcome for them or for the company. Sometimes it's an ego play, not wanting to believe a company will survive beyond them. And sometimes it's just not being able to accept the notion that family isn't the best solution.

Getty recently traveled to the Northwest to meet a 90-year old business owner who was finally considering selling his company. The reason? He understood that his sons, already in their late 60s, were likely not going to be able to run the firm. And yet, the father, long past the point of worrying about retirement, could not give up on the idea of keeping it in the family. After talking for an hour, the owner realized that a third-party buyer was likely going to be necessary. "He knew it intellectually, but wouldn't admit it to a stranger," says Getty. "He told me, 'You pulled at my heart.'"

Handling Failure
Of course, those are the concerns of a successful company-having something that family can inherit or a business that's earned enough to build a nest egg for retirement.

What about those that are not successful? It's a sad fact of life, but most small companies fail. And of those that do succeed, many rarely make it beyond a Schedule-C kind of enterprise.

For every Lowe's and Chipotle, there are hundreds of thousands of small businesses that had hopes for the bright lights - or even a spotlight -but never got there.

Roughly 552,600 new businesses launched in 2009-with 660,900 closing, according to the U.S. Small Business Association. Roughly seven out of every 10 firms survive for at least two years, but only a quarter of them are still around 15 years later.

"People think they have a new idea or better idea and they start something," says Bill Dunkelberg, chief economist for the National Federation of Independent Business, chairman of Liberty Bell Bank in Marlton. N.J., and professor of economics at Temple University. "If they're right, they're rewarded with profits. If they're wrong, they have to terminate. Lots of them do make it and some of them go big. Most of them don't grow."

And today, most small business owners are not even asking for loans, says Dunkelberg. They are holding on to cash reserves instead of reinvesting in their business because of the turbulence in the economy. And for those trying to launch a new business, two-thirds will start with their personal savings as "banks are not venture capitalists and won't lend money unless you have a track record," he says.

Avenue Bank's Williams concurs. A current client, an accountant with a large firm, hopes to strike out on his own. It's been his dream, Williams says, for years. But with his W2 income set to vaporize when he starts his business, Williams has been advising her client to build a cash reserve by working part-time for his current firm, and part-time on his own until he can take the leap.

Sometimes, though, she believes an investor shouldn't take the leap at all - or at least with the financial resources they have in place. Three months ago, a prospect came into the bank hoping to open a restaurant, but without any experience in the field. Instead, she had an inheritance and hoped to use it as capital. But Williams turned her down for a loan, saying she didn't want to see the woman potentially lose her inheritance, which would have been needed for collateral.

"She went to another bank, used the inheritance as the collateral and the business is already shut down," Williams says.

Caution, Sharp Curves Ahead
Clearly that's not where an advisor wants a client to end up with their business. And often that means advising them to start slow before they take a leap-or at least use cautionary measures to protect themselves.

A client of Arnett's with a technology startup had been allowing employees visiting from out of the country to stay with him in his condo in the Seattle area. But Arnett raised a red flag, explaining the liability of mixing his personal assets with business use, on the off-chance something happened to one of his employees.

In another scenario, Fulton Bank's Stetter had to assist one of his clients, an Amish builder, through a terrible experience. Running a construction company that specializes in pole barns-structures usually built with wooden poles as their main support-the client had the misfortune of having one of his own clients fall through an opening on the site. The client who fell then sued the builder for $2 million.

"Because he was Amish, he didn't believe in suing people or insurance," says Stetter. "He was pretty much out of debt, but now he's had to restructure his business."

These are the kinds of experiences an advisor does not want his or her clients to have. Yet they happen. And understanding the personal as well as the business components allows advisors to help clients navigate not just when a client is growing his company-but when times get tough too.

Williams had a client pass away suddenly last January. A husband-and-wife team, the father had long ago handed the title of president to his son, but hadn't formalized the paperwork on the family's manufacturing company. And when the father died, Williams stepped in to rework documents, refinance business loans and assist the family through trust and estate concerns.

Still, even Williams was surprised to learn of some life insurance policies that had been handled by the father's attorney. That influx of capital has now made a big impact, Williams says, on the longevity of the company. While the death was a shock, she knew the family had been well advised, by her as well as others, and well prepared even for an event so unexpected.

"It was a very emotional time-and hard to approach, but we were there on their side," says Williams. "And now things will be well taken care of and they're in wonderful shape."