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Our Clients

At Pinnacle Financial Group, we work with a variety of clients, from young couples saving for college and retirement, to senior citizens living off income from their portfolio and worried about preserving their wealth for the next generation.

In the links below, we describe some of our typical clients and the services that we provide for them. The names and the details of each story have been changed to protect our clients’ privacy. But the partners at Pinnacle Financial Group have helped clients implement each of the strategies described below. No matter what your current financial needs, our professionals can help you meet your lifetime goals.


Married with children and saving for college and retirement? Trying to maximize the return of your portfolio while minimizing risk? Read about Ryan and Katie under “Families – Accumulating Wealth”


Nearing retirement or recently retired and wondering if your investments will last as long as you do? Read about Andrew and Madeline under “Retirement – Monetizing Wealth”

Senior Citizens

Worried about the volatility of your portfolio and hoping to leave your wealth as a legacy to the next generation? Read about Matthew and Ellie under “Estate Planning – Preserving Wealth”


Has life thrown you an unexpected challenge? Do you feel overwhelmed by your new financial pressures? Read about Marybeth under “Transitions – Marriage, Job Changes, Divorce, Death”
Families - Accumulating Wealth

Many of our clients are in their 40s and 50s and are saving for the dual goals of college for the kids and retirement. We help them make the difficult decisions to allocate savings between college and retirement. We help them protect their assets with appropriate amounts of property/casualty, disability, and life insurance. And we help them maximize the return of their investment portfolio while minimizing the risks of their investments. 

Ryan and Katie
(the names and details of this story have been changed to protect our clients' privacy)
Ryan and Katie had never worked with an investment advisor before. But when Katie left her job as a public relations executive in order to stay home with the kids, they worried about whether they were still on track with their retirement plans. Although Ryan was a commercial banker for a large bank downtown, he was concerned that he did not spend an adequate amount of time monitoring and managing their investment portfolio. And with Madison and Jack already in grade school, college was rapidly approaching. 

Ryan and Katie struggled with deciding how to allocate their income between current spending, saving for retirement, saving for college, and other uncertainties such as disability and life insurance. Ryan and Katie wanted to be sure that they were on the right path to a secure financial future.

We prepared a comprehensive financial plan for Ryan and Katie. We reviewed their disability income insurance coverage. Although Ryan had some life insurance through his employer, it was not enough to allow Katie to stay home with the kids full time while they were in school. We recommended an additional term life insurance policy that would ensure that Katie could stay home with Jack and Madison until they went to college. The life insurance would also help pay for college in the event that something happened to Ryan. We reviewed their property/casualty insurance coverage and recommended that they increase their deductibles to reduce their premiums, but consider raising their liability coverage given their growing family net worth.

With regard to saving for college and retirement, we provided Ryan and Katie with multiple scenarios that projected their retirement spending based on how much of their savings they allocated to retirement versus college. We projected the total cost of college assuming Jack and Madison attended the local Big Ten public school, and also what it might cost if the kids attended the prestigious private school from which Katie graduated. 

Based on the information that we presented, Ryan and Katie decided that Katie would return to work part-time when the kids got into high school in order to help pay for college and supplement their retirement savings. We helped them direct their college savings to a tax efficient 529 plan. Ryan and Katie were already maxing out the annual contributions into Ryan’s 401K plan. This allowed them to achieve the maximum matching contribution from his employer. But we also reviewed their family budget and suggested some areas to cut so that they could free up a few more dollars to save for retirement. 

Finally, we suggested that they take the stock that Ryan received from his employer, which had a very low cost basis, and use that to make charitable donations. This suggestion alone reduced their annual tax bill by approximately $1,500, while allowing them to maintain their significant charitable giving goals.

Ryan and Katie also wanted help with investing their growing net worth. They are comfortable with the risk of the stock market and have a very long-term time horizon. So we put together an aggressive asset allocation that reflected their risk tolerance and long time horizon. We recommended a diversified portfolio of no-load mutual funds and exchange-traded funds (ETFs) that would best allow them to meet their financial goals, while minimizing as much as possible the risks of investing in the stock market.
Retirement - Monetizing Wealth

Many of our clients are in their 50s or 60s, and they are nearing retirement or have just left the work force.   They have worked a lifetime to accumulate assets and now their thoughts turn to monetizing those assets to live in retirement. This can be an unsettling time, and we can help ease their mind by running projections of what is a safe annual withdrawal rate from their investments.  We help them reposition their assets to reduce the risk of their portfolio and increase its income potential, while still generating long-term growth. This is also an excellent time to begin to consider estate preservation techniques, to minimize the future impact of estate taxes. 

Andrew and Madeline
(the names and details of this story have been changed to protect our clients' privacy)
Andrew and Madeline were approaching retirement and they were scared. They had worked for years with a broker at one of the major brokerage firms, but they were unsure of whether or not they had enough money to retire, and they were tired of feeling like their broker was always trying to sell them a hot investment idea. The kids were grown and college was paid for, but now they faced the prospect of quitting their jobs and living the rest of their life without a paycheck. Andrew told us that the thought of retiring and giving up his paycheck was causing him to lose sleep at night. He was beginning to have second doubts about retiring at age 62 as he had always planned.

We prepared some retirement projections which helped put their mind at ease. Andrew and Madeline had been diligent savers. When college was paid for and the kids were out of the house, they used their discretionary cash flow to increase their annual savings. Because they had always lived below their means, we calculated that their current assets plus Social Security plus Andrew’s modest pension should easily cover their retirement spending needs, with a nice cushion left over for the kids to inherit someday. 

Although they had a small remaining balance on their mortgage at a low interest rate, Andrew felt strongly that they should pay off the mortgage prior to retirement. So we helped them choose which investments to sell in order to minimize capital gains taxes and generate enough proceeds to retire the mortgage. We also analyzed their estate plan, but decided that given their age, we would hold off on a gifting plan to their children for a few more years. This is a decision that we revisit annually in our meetings with the couple.

Andrew and Madeline were both on the alumni board of their alma mater, and told us that it was their dream to leave a portion of their wealth to this university upon their death, but they were concerned this might not be financially feasible. Madeline had built a small business into a thriving entity and was now considering selling the business prior to retirement. We encouraged Madeline to consider transferring the business to a charitable remainder trust. We helped them set up the trust and connected them with legal and accounting advisors to manage the administrative aspects of the trust.   

Madeline negotiated the sale of the business while transferring her ownership interest into the charitable remainder trust. The transfer of the business to the trust resulted in an immediate charitable tax deduction for the couple. Madeline’s cost basis in the business was essentially zero, since she had built it from the ground up. No capital gains taxes were due at the time the charitable trust sold the business, since charities are exempt from income taxes. 

Pinnacle Financial Group invested the proceeds of the sale inside of the trust to generate income for Andrew and Madeline while minimizing the income taxes due as a result of distributions from the trust. Andrew and Madeline receive a fixed percentage of the trust assets each year to supplement their retirement spending. Upon their death, all assets remaining inside of the trust will be transferred to their alma mater.

Andrew was a participant in a defined benefit pension plan through his current employer. We helped Andrew decide between a lump sum distribution, a single life annuity, and a joint and survivor annuity. We also analyzed whether or not it made sense to consider taking the higher single life annuity, but insuring against his premature death with life insurance that would supplement Madeline’s income in the event that Andrew’s pension would disappear upon his death. Andrew and Madeline ultimately decided that they would elect the lump sum distribution. Because interest rates were low, we showed them that a modest return on investment would allow the lump sum distribution to provide greater lifetime family income, even if they lived to age 100. The lump sum distribution had the additional benefit of preserving this asset for the benefit of their children upon their death.

Finally, we helped Andrew and Madeline invest their nest egg, including the charitable remainder trust. Because of their income from Social Security, Andrew’s pension, and the charitable remainder trust, their need for income from their investment portfolio was quite low. Nonetheless, both Andrew and Madeline wanted to invest their portfolio more conservatively now that they were retired, so we helped them reallocate a portion of their assets to more conservative investments. 

They decided to invest the remainder of their portfolio in growth assets, to help them stay ahead of inflation and hopefully to leave a legacy for their children. We also established a monthly transfer of funds from their brokerage account to their checking account, to fund monthly spending needs. Because a portion of the assets are invested for growth and total return, we sell investments when necessary to make sure that there is always enough cash in the brokerage account to fund these monthly transfers. Madeline had always handled the family checkbook, and she commented that it was almost like receiving a salary every month.
Estate Planning - Preserving Wealth

We have extensive experience with some of the best estate tax attorneys, accountants, and third party administrators in the Chicagoland area.  Together, we can design an estate plan that will achieve your goals, whether that be to preserve as much of your estate as possible for your heirs or for the charities that mean the most to you.  Because of the many changes to estate tax laws, both historically and prospectively, this is an area that requires constant attention and review.  Every family’s circumstances will be unique and the techniques we used for Matthew and Ellie may not be appropriate for your financial situation.  But we can work with your attorney and accountant to ensure that we develop the appropriate estate plan to meet your goals

Matthew and Ellie
(the names and details of this story have been changed to protect our clients' privacy)
Matthew and Ellie were in their late 70s and their estate attorney had just informed them that their heirs might be hit with a multi-million dollar estate tax bill. In conjunction with their estate attorney and accountant, we put in place a multi-part estate plan. Matthew had been a successful corporate executive and in his retirement, had started a thriving consulting business. Matthew’s corporate pension plus their Social Security payments easily covered their current spending. In addition, they had a sizable investment portfolio, much of it individual stock positions that they had purchased as much as 40 years earlier at a very low cost basis.

Based on information that we presented to their advisors and our analysis of the economic benefits, Matthew and Ellie decided to put in place two separate Family LLCs.  There were multiple business reasons for the Family LLC. Matthew and Ellie wanted to pass along to their children their commitment to annual savings and to educate them in the principles of modern investment management. By consolidating management of the family’s investments, the family would have access to professional investment management services that might be subject to minimum required asset levels. Additionally, the Family LLC might qualify for price breaks that may be available only to larger pools of investments. The Family LLC also offered the potential of significant future estate tax savings.

Matthew and Ellie were the managing members of the Family LLC. Therefore, they had control over how the assets of the Family LLC were invested and could control when distributions were made to the members. Their children contributed a modest amount of assets to the Family LLC, mostly securities which their parents had gifted to them over the years. In addition, Matthew and Ellie contributed a portion of their investment portfolio. At the outset, Matthew and Ellie had a significantly larger stake in the first Family LLC than their children, who retained only a very small member’s interest in the first Family LLC.

After funding the first Family LLC, Matthew and Ellie used a portion of their lifetime gifting exemption to gift roughly 50% of their interest in the LLC to their children. As the managing members of the Family LLC, they still controlled how the assets were invested and when distributions could be made to the members. But because they now had a less than 50% interest in this first Family LLC, upon their death, the valuation of their 50% interest in this Family LLC would be discounted significantly by the IRS, resulting in significant estate tax savings.

With the remainder of their investment portfolio, Matthew and Ellie funded a second Family LLC. Because Matthew’s pension and their combined Social Security payments more than covered their annual spending, they had not spent any of the principal from this investment portfolio in years. Matthew and Ellie told us that their goal was to grow their portfolio to provide the maximum asset transfer to their children upon their death. The children again contributed a modest amount of assets into the second Family LLC. 

Once the second Family LLC was established, Matthew and Ellie began gifting their member’s interest in this second Family LLC to their children and grandchildren using the annual gift tax exemption. Because they were gifting a minority interest which provided little control over the investment or distribution of the Family LLC assets, the IRS allowed them to discount the value of the member’s interests when calculating the amount of the annual gift. This allowed the family to leverage the value of the annual gifts, resulting in a more rapid transfer of assets to the children and grandchildren, while still avoiding gift taxes on the annual gifts. Even though Matthew and Ellie continued to maintain a majority ownership stake in this second Family LLC, upon their death, the IRS would still allow a modest discount in the value of their ownership interest in the second Family LLC.

Finally, Matthew had a significant 401K balance from his days as a corporate executive. Unfortunately, this portfolio would be subject to both estate taxes and income taxes upon his death, and at the maximum tax rates then in place. We helped Matthew establish a pension plan for his consulting business. We rolled his 401K assets into the pension plan. Matthew was the only employee and therefore the only participant in the pension plan. Because he was older than 70 ½, he elected to take a lifetime annuity. Electing the lifetime annuity removed these assets from his estate, as he no longer had any claim on these assets beyond the annual annuity payment, which would end upon his death. 

Additionally, Matthew had transferred the ownership of the consulting business to his children. The only assets of the consulting business were the pension plan assets. Pinnacle Financial Group continued to manage the pension plan assets for the family and made the required annual annuity payments to Matthew from the income of the pension plan investments. Upon Matthew’s death, the consulting business and its overfunded pension plan was sold to another company with an underfunded pension plan. The family had to pay capital gains taxes on the sale of the company, but they were able to avoid both estate taxation and ordinary income taxation on the assets which had originally been inside of Matthew’s 401K.
Transitions - Marriage, Job Changes, Divorce, Death
Life transitions are inherently stressful.  Whether the result of death, divorce, or an unexpected job loss, you may find yourself facing complex financial questions at an uncertain time in your life.  Prior planning and the utmost confidence in your financial advisor can provide significant peace of mind as you navigate through these difficult times.  We can help you analyze your different options and put in place a plan that will allow you to meet your financial goals.  We want to be your financial partner for the long run, through good times and bad.  To earn that right, we know we must earn your trust.

Marybeth and Peter
(the names and details of this story have been changed to protect our clients' privacy)
Marybeth and Peter had been married for nearly 50 years when he passed away. Peter doted on Marybeth, and continued to handle all of their finances even into his 80s. Peter had been managing their portfolio primarily on his own for years, and he had investment accounts scattered amongst many different custodians and brokerage firms. Needless to say, Marybeth was overwhelmed, emotionally and financially, by the loss of her husband, partner, and best friend.

Because we had done some financial planning for Peter and Marybeth over the years and were currently managing a small portion of their investment portfolio, we were able to immediately assure Marybeth that her financial future was secure. We encouraged Marybeth and the children to take their time to grieve the loss of their husband and father. In the meantime, we helped them complete the paperwork to claim the death benefit on two life insurance policies that Peter had maintained to protect Marybeth.

When Marybeth and her children were ready, we met with them and compiled a detailed net worth statement.  Peter had done a good job of providing for Marybeth, but as he got older, his record-keeping became a little more sporadic. The kids had found some old spreadsheets which listed certain investments, but it was unclear whether those assets had been sold or perhaps transferred into other current investment accounts. 

We helped the family dig through all of Peter and Marybeth’s financial records, reviewed past tax returns to see which investments were still generating current income, and collected all of the statements which they were receiving at their home. We were able to help them create a paper trail so that they could be sure we had identified all of the assets that Marybeth now owned, but could also track what had happened to each of the investments listed on Peter’s old spreadsheets.

Peter was the primary beneficiary of Marybeth’s IRA and the kids were the secondary beneficiaries. We helped Marybeth change the beneficiary designation on her IRA, listing the kids as primary beneficiaries, and her grandkids, including any future grandkids, as secondary beneficiaries. We consolidated Marybeth’s multiple investment accounts with one custodian, to reduce the paperwork that she was receiving and to provide for ease of management of her investments. 

We rebalanced the portfolio to reduce its volatility, as Marybeth’s risk tolerance was more conservative than Peter’s had been. At the same time, we helped Marybeth keep a small portion of her portfolio in growth investments, but structured the portfolio to reduce risk as much as possible by broadly diversifying between many different asset classes. We set up a monthly transfer of cash to Marybeth’s checking account, to fund her annual living needs and to leave a little extra which she used to make annual gifts to her grandchildren.

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