When Mike Flanagan speaks of having an entrepreneur's passion, he's drawing from his own well. After running his own accounting practice for 23 years, he sold the firm in 1997, staying on for six more years before retiring in 2003.

Only then did he launch a new career as a financial advisor at Wilson Bank & Trust. (Raymond James is the third-party marketer.) He'll mark his 10th anniversary later this year.

Flanagan puts his entrepreneurial expertise and empathy to work every day for his small business clients. And while not required, having his considerable experience in navigating the business world can only help his clients trust his judgement more, particularly in the past few years.

"They're good businesspeople, technically competent, good managers and have entrepreneurial spirits," he says. "But no one could have imagined having five years where there were almost no sales."

A recent client of more than 20 years started drawing on his $1 million account to avoid shuttering his contracting business.

Flanagan started scheduling meetings with him every one to two months, planning different scenarios from liquidating properties to considering bankruptcy-things the client didn't want to entertain, but which Flanagan knew had to be considered.

Finding a buyer for half of the developed lots on the client's subdivision proved to be the answer, reducing interest payments and debt load. "We discussed things he may not have wanted to do," says the Lebanon, Tenn.-based Flanagan. "But they were things he needed to seriously consider so that he could have opportunities in the future."

Today, more than hand-holding is required to keep small business owners fluid. Advisors need to deliver realistic advice, creative solutions and temper expectations - all without dispelling an entrepreneur's passion and dream. As small businesses continue to struggle, or at least feel as if they are, these skills have never been more needed.

Weak sales remain the most difficult stumbling block, with 18% of small business owners citing this as a top concern, according to a March report from the National Federation of Independent Business. And in terms of capital spending-from improving physical structures to funding expansions-just 5% of small business owners feel that now is a good time to expand their facilities. That's historically a "very weak number," according to the NFIB.

But banks say they're starting to see a brighter horizon-particularly for clients who have stayed resilient. "We are seeing businesses stabilize and return to profitability," says Quincy Miller, executive vice president and head of business banking for Citizens Financial Group in Dedham, Mass. "We're definitely moving in the right direction in how small businesses have adapted and evolved, and are looking to take advantage of potential growth in the marketplace."

That growth is tied to not only finding retirement options for their entrepreneurial clients - but also solutions that can stabilize their businesses so they're ready for the next generation, or solvent enough to sell when a client so decides.

In order to reach this level, banks are encouraging their employees to work with each other more closely within branches and even across branches to get a more complete view of the client's financial picture.

For example, if a commercial loan is due, perhaps there are assets that only the advisor knows about that would help pay some of that debt.

Come Together

If an advisor has a good understanding of a small business client's total financial foundation, it's easier to have a conversation, says Jeff Martin, senior vice president, and director of wealth planning for Fifth Third Private Bank, based in Charlotte, N.C. "We want to have an understanding not only of the business, but also the family's personal assets."

Seeing the many facets of a client's finances can help not just the investor-but the bank as well. While an advisor often focuses first on helping his clients prepare for retirement, small business owners can have additional concerns; namely, their livelihood. Protecting both an investor's savings and their business at the same time is what an advisor must really consider.

Fifth Third Bank advisor Chad Holland had a client who built a couple of speculative multimillion dollar homes just as the housing crisis hit. With debt still on the bank's books, Fifth Third's commercial lending side was looking to get repaid-even though the homes still had not been sold.

As the wealth management advisor, Holland understood his client's personal holdings, and was able to help broker the investor's securities to help "reconstitute debt to the bank," that not only gave his client more breathing room, but also saved $150,000 in interest payments a year-while paying off the demand held on the commercial side. The client was so pleased, Holland also crafted another deal using the client's personal holdings to pay off a different line with another bank.

"The client loves it because he sees us as being creative and going out of our way," says Holland, a vice president who has been with the bank since July 2011. "One of the most frustrating things for clients is being told 'No.' Instead of saying, 'We may not be able to do it this way,' we say, "Let's dig a little deeper and see how we can get it done.'"

Digging deeper into a client's financial landscape is a strategy that has paid off for Marti Brust as well. Recently, the Denver-based wealth advisor had a client who called to liquidate his IRAs quickly in order to make a payroll obligation two weeks later, as receivables were running late and he couldn't cover his employees' salaries. Because Brust could see her client's holdings at UMB Financial Services, she called in private bankers at the institution who were able to create a line of credit on the client's home at a low rate, and then use the funds as a bridge loan to cover payroll. He cleared the credit line once his business collected on the outstanding accounts.

The client avoided penalties from accessing his IRA prematurely, and also took steps to prevent a repeat scenario by diversifying his revenue base so that the business was less reliant on that one particular vendor.

"And this is an overriding theme for us," says Brust. "The more informed we are about a client's entire financial picture, the more responsive we can be. And that absolutely includes a client's small business."

Flanagan would agree. His very first client, and one who's still with him, went through a difficult time in the 1980s with 10 homes he couldn't sell-potentially facing bankruptcy. Flanagan was able to work with creditors, and put the homes in a limited partnership, which sold 10 years later at a profit.

Having that history with the investor, and Flanagan's detailed knowledge of his client's financial situation, also served him two years ago when the client went from selling 150 homes a year to selling about 12 to 18.

The client and his partner were dipping into savings when Flanagan suggested freezing the company's 401(k) as they could no longer afford the matching program.

Instead, Flanagan met with employees, helping them roll their former retirement accounts into IRAs, which the client offered to fund when they could, and saved the company an additional $4,000 to $5,000 a year in fees.

"It's been the worst period he's seen in 40 years," says Flanagan. "But it helped them free up operating cash flow, so they didn't have to lay off people."

Indirect Lead

Advisors who cater to entrepreneurs also need to be flexible-even in the way a meeting can turn. Sometimes a discussion about investments ends up taking a side path toward protecting more than just cash. Being attuned to a situation can require sensing when needs go beyond liquidity.

Ralph Ganchero, a senior financial advisor with UnionBanc Investment Services in Beverly Hills, Calif., recently sat down with two brothers who own a light manufacturing business that they inherited from their father. The point of the meeting was to talk about their investments. But Ganchero quickly realized the chat was developing into a discussion about how to protect their legacy.

"Their father didn't have a [succession] plan, and they had inherited those thoughts," says Ganchero. "So we started talking about what would happen if a partner died, or one had to buy out the other, and where those funds would come from."

Ganchero and his team began to look at best practices among other companies in the same field, and by the end of their meeting the clients felt good that they had addressed an issue they didn't even realize was in the back of their minds.

Taking Care of Business

That's not to say that retirement isn't a crucial area where small business owners often need to be pushed to pay attention. Many advisors who cater to entrepreneurs say these clients in particular often have a hard time redirecting funds from their business to themselves. And knowing how to address that issue is a significant one for many business owners, says Fifth Third's Martin.

"They always dream big and want to hit it big," he says. "You need to be realistic with them because some of them will continue to put most of their investments, whether that's financial or time, into their business. And we want to make it okay for them to retire when they want to retire."

Sometimes that requires an advisor helping a client take off their business hat and then put on their family hat, says Rocco Papandrea, a New York-based Merrill Lynch wealth management advisor. He notes that while many of his clients are extremely successful with their businesses, they're not always as laser focused on their personal needs-from creating college accounts for children or grandchildren to ensuring retirement funds for themselves and their spouse. It can be a delicate balance to direct a passionate entrepreneur to invest in his own life, instead of continuing to plow funds back into his own business - which many view as their life's work.

Gregory Wade, a financial advisor and managing director with Wells Fargo Advisors in Roswell, Ga. says that often it's just a matter of having patience. He understands that clients who have started their own successful businesses have a great deal of confidence in themselves and their actions. Wade will find he can introduce a suggestion, but has to allow his clients to come to a decision on their own.

One current client, for example, has very little saved in outside investments, but has a business that has a high valuation. Like some of his small business clients, the owner is "pretty cash heavy," says Wade, who is talking to him about investing some of that liquidity in something outside of his company, to at least diversify holdings and reduce some risk. But business owners tend to feel more comfortable keeping a substantial amount of cash on hand-particularly if they feel they may need to put it back into their company, and in a short period of time.

"They're pretty quick to act and that's nice," says Wade. "They do take leadership from their advisors. They like recommendations and then act on them."

Talking Them Down from the Ledge

Merrill Lynch's Papandrea agrees that small business owners often have a good sense of what direction is right for them, particularly those with experience. Where he sees more of an issue is with newer entrepreneurs, those who grow exuberant about the growth of their start-ups and sometimes try to move more quickly than is financially prudent.

He recalls one client who garnered a large contract her first year in business with a major beverage distributor and quickly decided to buy a small house. Instead, the New York-based advisor brought in a CPA who worked with the client to draw up a business plan with a three- to five-year horizon to ensure her company would have a future-which didn't include taking out a large sum to put on a home just then.

"And sure enough, she came in last month to thank me," he says. "And she will come to us again."

Citizens' Miller says that much of what his team is doing is helping clients stay realistic as they pursue their dream. For example, they may decide they want to expand immediately, and sell whatever their particular widget is to one million clients tomorrow. But if don't have the cash flow to support that expansion then that's not going to be plausible. However, telling a client that? Not advisable, says Miller.

Instead, the bank's business banking officers will approach entrepreneurs with specific strategies, which often means educating them on business basics from receivables to cash flows. The goal is not to tell a client what they can and cannot do, but lead them to where they come up with a realization on their own.

"You have to be careful," he says. "We don't try to get into what's not possible. But we may say, 'We can help you create a process to help you speed up your collection of receivables, and if you can't, we want to look at slowing down your payables.' Then they will come up to their own conclusions that maybe they can't take on 1,000 widgets but can instead deliver 500."

Education All Around

Educating a client means educating advisors as well. And at Citizens, officers are invited to monthly Skill Builder meetings, or "modules," where business banking staff are educated on such topics as credit and foreign exchange. The program also encourages staff to work with others at the bank from those in payroll to merchant services, and help them look at different ways of advising their entrepreneurial clients. In the past few years, helping these clients run leaner has been crucial to their surviving the economic downturn.

At First Tennessee Advisory Services, in Memphis, Tenn., president Karen Kruse says the firm trained a CFA/CFP in business valuation and transitions about five years ago to help grow its own financial planning group. While the business transition service "kind of dried up in 2008 for about three to four years," says Kruse, it's come back. And now they can walk a small business owner through many steps from setting up retirement plans for their employees to helping them prepare their company for a sale or a transfer when they're potentially ready to retire.

Sometimes that step comes sooner than a client hopes. Or long-term plans don't take the road an entrepreneur and an advisor had imagined.

And sometimes, those unexpected roads lead to sad endings.

Wilson Bank's Flanagan had a tax client who transitioned to his financial advisory practice when Flanagan started his own second career. A fast-food franchise owner, the client had always hoped that one day his son would take over the business, which had done very well. The client had paid off debt to where he owned one of the franchises outright, had interest in six others, and had also hired middle level managers about 15 years earlier, at Flanagan's own suggestion, so he could develop the franchises more -cutting work in half and doubling their volume.

But two years ago, Flanagan helped his client begin to sell off the businesses. The client's wife had battled with cancer, and his son had been diagnosed as well. His ability to one day work the 100-hour workweek as his father had done was no longer plausible. The client wanted to ensure his family would be taken care of and with the balance of the estate at $2.5 million, he and Flanagan started finalizing a trust and other details to ensure his family was protected.

He came to Flanagan's office in early March to sign the last of the documents, and informed his advisor that while both his wife and son were in remission, he had just been diagnosed with cancer as well. Flanagan says he's happy at least that the two had sat together and taken the next steps.

"He said, 'If you hadn't helped and pushed me I wouldn't have all this done,'" Flanagan says. "To be successful, you have to have the level of trust that what you do for them, you would do for yourself."

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