We are dedicated to providing investment management and strategic wealth planning that is specific to you and your situation. Simply put, we strive to be our client’s trusted advisor. As a financial advisory firm, our primary focus is to provide unbiased opinions that are designed to achieve long term investment results.

We are dedicated to professionally supporting, educating, and providing informed direction to each and every client and we do this with the highest levels of trust, integrity and respect while always collaborating using a team approach.

OUR TEAM

Tim Dillow CFP®

Founder and President

Tim is the Founder and President of Dillow Wealth Management. Tim has served for nearly 20 years in various roles within the financial services industry. Tim’s diverse experience has produced a unique skill set and approach to wealth management. Through his career he has served in management, capital markets and wealth advisor roles. Financial planning is at the core of Tim’s practice and he holds the esteemed Certified Financial Planning designation. His areas of focus are multi-generational wealth planning, philanthropic strategies, and portfolio construction. Tim is highly regarded for his knowledge and experience in the development and utilization of structured products.

Tim lives in Wheaton, IL with his wife of 20 years and three children. Tim holds a BA in philosophy from the University of Wisconsin-Parkside.

Ian Dillow

Analyst

Ian Dillow is a passionate and driven wealth management professional in his first year with the firm. Ian is expected to graduate with a degree in Finance from High Point University May 2025. Ian is focused on helping individuals and families take control of their financial futures through thoughtful planning and personalized strategies. With a strong foundation in financial principles and a client-first mindset, Ian is committed to building lasting relationships based on trust, transparency, and results.

Melissa Wilczak

Director of Finance

Melissa Wilczak is a Director in the Finance department of Cypress Holdings Group. She has over 25 years of investment and wealth management experience which included roles in capital markets and wealth advisory.

Prior to Cypress, Melissa held the role of Group Administrator and Senior Wealth Strategy Associate at UBS Financial Services where she managed all operational and administrative functions of a large private wealth advisory team. Before that, Melissa was a Senior Wealth Associate in Private Banking and Investment Group at Merrill Lynch.

Melissa received her Bachelors of Science from Rice University. She lives in Clarendon Hills, IL with her husband and two daughters.

Christopher L. Hughes​

Director of Finance

Christopher  L. Hughes, based in suburban Chicago, is a co-founder of Cypress  Holdings Group. He has over 27 years experience in the investment and  capital markets with a focus on private equity investing including  making direct investments, structuring joint ventures, forming long-term operating partnerships, and privatizations of public companies.

Chris  was formerly a Managing Director of Deutsche Bank’s Alternative  Investments business (RREEF) and the Chief Executive Officer of RREEF  Global Securities and Structured Investments, based in Chicago and New  York. During his time with RREEF, he held various senior executive  positions and was a voting member of the RREEF Global Executive and  Principal Investment Committees since their inception. Previous  positions included CEO of RREEF Private Equity, Global Head of Capital  Markets and Structured Investments and North American Head of Capital  Markets. He also served as the Chairman of RREEF’S Private Equity and  Structured Debt Investment Committees.

Previous to RREEF, he was a  Senior-Vice President at Transwestern Commercial Services, an Executive  Director with CIBC and a Senior-Vice President with Heller Financial.  He started his career with KPMG where he was a manager in the national  consulting business line. Mr. Hughes is a member of the board of  directors at CloudOne Corporation, a cloud-based, on-demand  infrastructure computing company.

Chris was member of the 2005  Crain’s Chicago Business 40 Under 40. He has been actively involved with  and supported multiple charities including Feed My Starving Children,  GiantSteps and the Juvenile Diabetes Research Foundation ("JDRF").  Chris received his Bachelor of Arts in Business Administration from  Marquette University in Milwaukee, Wisconsin.

OUR PROCESS

1. Introductory Meeting

In our first meeting, we'll identify your goals, priorities, preferences, and any obstacles you may have. We'll also mutually establish what your expectations are for us, and if an ongoing partnership is the right fit.

2. Exploration & Preliminary Planning

After our first meeting, we'll take a deeper dive into your situation. As we have a more detailed conversation about your personal and financial goals, we'll start sketching a preliminary plan. The more open and transparent this phase is, the more detailed our plan will be.

3. Detailed Planning

Now that we have a foundation, we can deliver an easy-to-follow roadmap that will guide you towards your financial goals. This plan will address the areas that are most important to you, and outline the steps needed to conquer potential obstacles. Your plan will also aim to gain maximum returns via a solid, tax-efficient portfolio.

4. Ongoing Support & Advice

Life is constantly changing, and your goals will too. When new priorities lead you towards different approaches to wealth management and savings, we'll be here to adapt your plan so it transitions along with you.

OUR PHILOSOPHY

The core of who we are is rooted in loyalty and trust - it is the foundation from which we grow a relationship with our customers. This is what makes us different. From first time investors to those securing stability for their twilight years, we are here to support, educate, and offer insight to every individual that we encounter.

In the dizzying world of stock markets and financial lingo, we often become too fixated on the immediate numbers and lose sight of the bigger picture. We want to understand what truly matters to you and tailor a holistic financial plan that gives you peace of mind today and tomorrow. We care as much about why you are investing as what you are investing in.

WHO WE SERVE

Business Owners

Growing a business is a difficult undertaking today as business owners must confront a myriad of tax laws and regulations while trying to effectively create products or services, manage their employees, develop and cultivate clients, and do so profitably.

Often times business owners are too absorbed in their business to tend to their own financial needs, and they may also overlook key planning considerations that could help their business grow and prosper. Also, the livelihood of a business owner can be imperilled when unexpected events occur that adversely affect the bottom line of the business.

For many business owners, their business is their primary retirement asset. After many years of building a successful business they expect to convert it to an income for retirement by selling it. If they are relying upon the business as their sole means of retirement they run the risk that it may not attain the value needed to produce the needed income.

Businesses can fail. Businesses can lose value in certain economic cycles. The timing is not always right to sell a business. Many times the true value of the business lies in the talents and good will of the business owner who won’t be around to run the business after he retires.

Business owners today must prepare for retirement with the same level of diversification recommended for any retirement plan. Business owners have access to a number of qualified and nonqualified retirement plan options that can provide a cornerstone for their retirement income needs.

When a business partner dies, the business loses a valuable asset and could suffer in the short term. The long term issue for surviving business owners is whether the business can survive when the partner’s family members show up for their interest in the business.

For the families of business partners, the business interest is often their biggest asset and they become the rightful owner of that interest at the death of the partner. They will want to receive their share of the business, either in direct compensation or through their participation as an active partner in the business.

If the surviving partner does not have the capital to compensate the family for their share, their options are limited and not very attractive. A business succession plan can provide for the orderly transfer of the business interest from the deceased’s family to the business.

One of the more devastating events a small business can suffer is the loss of a key employee. Often times it’s a key employee who brings a special talent to the business and is responsible for much of the success of the business owner. The loss of such a valuable asset could set the business back for a period of time, and at tremendous cost, while the business owner seeks to find a replacement, if one can be found at all.

In financial planning, we are taught that it our most valuable assets – our home, our ability to earn income, our cars – should be insured against an unexpected loss. It’s no different for business owners as the loss of a valuable business asset could imperil the business.

Buying life insurance coverage on a key employee makes good business sense. The amount of coverage should be enough to cover the costs of recruiting and paying a replacement, loss of earnings to the company, any redemption of stock or a salary continuation plan arrangement with the surviving family.

In a small business setting, it could take years to find or develop the executive talent needed to build the business to the next level. Executive talent is hard to come by, and it is even more difficult on the business when it walks out the door in pursuit of another opportunity.

When key executives are presented with a strong monetary incentive package, they are more likely to stay and utilize their talents where they feel appreciated and appropriately rewarded. Structured incentive plans can help keep key executives in place and motivate them to higher levels of performance.

Plans such as Nonqualified Deferred Compensation, Executive Bonus, and Split Dollar Life Insurance are life insurance based plans that enable the business to offer current and future benefits to their key executives in exchange for their continued service for a specified period of time.

Families

Managing your finances is an important component to any financial security plan. Along with the protection offered through insurance and the goal setting provided by investment choices, money management strategies help you manage your savings on a daily basis.

From mortgage payments to tax savings, we can help you manage your money as effectively as possible, given your personal situation.

Depending on your stage of life, chances are you’ll have a distinct approach to saving. New graduates or young couples have different needs than retirees or mid-career families. But no matter your personal situation, we can help you develop financial habits that will lay a strong foundation for your savings.

Younger individuals and couples have a number of benefits in terms of financial management. Low insurance costs and a long investment horizon, combined with few responsibilities, can make for an excellent financial base. We can help you build on these advantages, while at the same time considering a debt load that might include student loans, car payments or perhaps a mortgage.

Couples planning for a first child enter into a new level of commitment—both personally and financially. Learn how to save for a child through specialized insurance and investment products, such as a Registered Education Savings Plan.

Mid-career professionals typically have higher incomes than younger investors—but they also carry more responsibilities. From mortgage payments to a child’s education, consider a financial plan that balances your needs and obligations.

Retirees have worked hard at their careers, and now is the time for relaxation and celebration. Chances are children have moved from home, the mortgage is mostly paid off and a few investments are coming to fruition. However, income levels may have dropped after retirement. Find out how to manage your finances in a way that allows you to fully enjoy the fruits of your hard work.

In short, no matter your life stage, contact us today to learn how to balance savings and investing with your other commitments.

No one likes taxes. But through the advice of a professional financial advisor, you can access products and services that help ease the burden. Charitable contributions, life insurance policies and investment products can all be useful tools in an effective tax strategy. Working together, we will consider your personal situation and design a tax plan that fits your needs.

Choose from a variety of products and services, such as:

  • Income-splitting for spouses or common-law couples.
  • Charitable donations, which benefits important not-for-profit work and allows donors to maximize tax credits.
  • Life insurance products that build tax-advantaged capital for retirement.
  • Investment products that provide for tax benefits

Contact us today to learn more about tax-planning products and services that are specifically tailored for your needs.

Preparing for succession after death is a difficult issue to discuss, but it is also an important part of any comprehensive financial plan.

We can help you and your loved ones approach succession planning in a constructive manner that ensures they avoid problems and are well cared for in the event of your death. The process involves two main considerations: life insurance and preparing a will.

Life insurance can ease the financial burden and provide security for your loved ones in the event of your death. A lump-sum payment can be used for mortgage costs or to supplement lost income, helping your successors during a difficult period. Financial security and stability can make it easier to cope with the loss of a loved one.

A written will provides a means to guide your loved ones through the succession process. By naming your executors and providing instructions on the distribution of your estate, your surviving loved ones avoid having to guess your wishes. Rather than provincial law determining how your assets are to be divided—a situation that can result in lengthy court proceedings—a clear, carefully considered written will provides clear instructions to your successors. Save your loved ones the stress of dealing with financial issues by planning for your succession while you are alive.

Contact us today to discuss succession planning in more detail.

Buying life insurance coverage on a key employee makes good business sense. The amount of coverage should be enough to cover the costs of recruiting and paying a replacement, loss of earnings to the company, any redemption of stock or a salary continuation plan arrangement with the surviving family.

Buying a home can be one of the most exciting purchases of your life—but it is also a big decision that will have a major impact on financial planning. Whether you’re looking at a one-bedroom condominium or a five-bedroom house, we will work with you to help plan a mortgage strategy that fits your needs and considers your other financial responsibilities.

From choosing the right time to buy a house to deciding whether it is even a good idea, we can help guide you through this important decision. By assessing all the costs involved - from taxes to renovations - we will work with you to determine whether taking out a mortgage makes sense for your budget.

If you are considering taking out a mortgage, contact us today to discuss how to do so in a way that best fits your situation.