Frequently Asked Questions

Who do you work with?

We work with a diverse range of clients, but we specialize in helping motivated mid-career professionals and families who are looking to build a strong financial foundation. Our clients are often in their 30s and 40s, juggling career growth, family life, and long-term financial goals. Most of our clients are either high net worth (over $1 million), high household income (over $300,000), or have complexity in their financial lives (e.g., equity compensation, inheritance, etc.).

Do I need to have a lot of money to work with you?

While many of our clients have high net worth or income, we believe financial planning should be accessible to everyone. We focus on your potential and your willingness to work towards your financial goals. Whether you're just starting out or have substantial assets, we're here to help.

Do you only work with people in their 30s and 40s?

While many of our clients fall into this age range, we welcome clients of all ages. Our services are tailored to each individual's needs, whether you're a recent graduate or planning for retirement. What matters most is your commitment to improving your financial health.

Do you work with clients in my state?

Yes, we work with clients in all 50 states. No matter where you're located in the U.S., we can provide our services to you.

Who is not a good fit for Two Trails?

We may not be the best fit for individuals looking for a hands-off approach or those solely interested in beating the market. Our ideal clients are engaged in their financial journey, open to guidance, and committed to long-term financial success. If you're looking for speculative or ultra high-risk investment strategies, we might not be the right match. Also, mean people (kidding, not kidding).

Are you a fiduciary?

Absolutely. As fiduciaries, we are legally and ethically bound to act in your best interest at all times. This means we'll always recommend what we believe is best for you, not what's most profitable for us.

Are you fee-only, and what does that mean exactly?

Yes, we are a fee-only advisory firm. This means we're compensated solely by the fees our clients pay us, not by commissions or kickbacks from selling financial products. We believe this structure greatly reduces potential conflicts of interest.

What makes you different from other financial advisors?

Our holistic, life-centered approach sets us apart. We don't just focus on investments or numbers; we look at your entire financial picture in the context of your life goals and values. My background in financial therapy has taught me how to lead great conversations around money and life, helping clients navigate the emotional aspects of financial decisions.

We're also tech-forward, using the latest tools to help you stay organized and achieve clarity. Most importantly, we prioritize education, ensuring you understand and feel confident about every financial decision you make.

Additionally, we've assembled a rockstar team of referral partners, including CPAs, attorneys, and insurance professionals, to ensure all aspects of your financial life are covered by true experts in their fields.

How is your fee determined?

Our fee is based on your net worth and income and is designed to track the complexity of your situation. Our annual fee ranges from $5,000 to $20,000 per year, allowing us to provide comprehensive services tailored to your specific needs.

Do you manage investments?

Yes, we offer investment management services as part of our comprehensive financial planning approach. We create personalized investment strategies aligned with your goals and risk tolerance, following our philosophy of low-cost, diversified, and tax-efficient investing. Our investment management services are included in your annual fee.

Where will my investments be held?

Your investments will be held at either Schwab or Altruist, based on your preference. Both are reputable custodians that ensure the safety of your assets and provide an additional layer of security and transparency.

What is your investment management philosophy?

Our investment approach is centered on five key principles: low cost, research-based, diversified, risk-appropriate, and tax-efficient. We believe in creating portfolios that align with your goals and risk tolerance while maximizing long-term returns and minimizing unnecessary costs and taxes. Our strategies are firmly grounded in academic research and empirical evidence, not market trends or hunches.

What if I want to manage my investments myself?

That's perfectly fine! We're here to support you in whatever capacity you need. We can provide guidance and recommendations while you maintain control over your investments, or we can focus on other areas of your financial plan.

Will you file my taxes for me?

While we don't file taxes directly, we provide tax planning strategies as part of our service. We can work closely with your tax professional or recommend one if needed to prepare your return.

Can you help with estate planning?

We can certainly help with the financial aspects of estate planning and provide general guidance. For complex legal matters, we'll collaborate with estate planning attorneys to ensure your wishes are properly documented and executed.

Can you help with insurance?

Yes, we can help analyze your insurance needs and recommend appropriate coverage. As a fee-only advisor, we don't sell insurance products, but we can guide you in finding the right policies to protect you and your family.

Where are you located?

We're based in Chicago, but we serve clients nationwide through virtual meetings.

Do you offer appointments on Saturdays or evenings?

We understand that many of our clients have busy schedules. Our regular hours are Monday to Friday, 9 AM to 4 PM. We do offer some evening appointments to accommodate your needs.

Do you offer in-person meetings?

While we primarily operate virtually to serve clients nationwide efficiently, we do have a soft spot for personal connections. If you're based in Chicago or Colorado (Andy’s home state), I’d love to take you out for coffee!

How do you protect my sensitive information?

Protecting your confidential information is our primary concern. We've implemented strict protocols to safeguard sensitive data, including a policy against transmitting such information via email. Instead, we utilize a secure online platform for exchanging sensitive documents and data.

Our operations rely heavily on cloud-based software solutions, all of which have been carefully vetted. To enhance security, we employ robust authentication methods, with a preference for app-based verification over SMS when possible. Additionally, all our devices are protected with complex, secure passwords.

How many clients do you serve?

We're building towards serving 50 total client families. By staying small, we can ensure that we give each client the attention they deserve, especially given the high net worth and complex financial situations of many of our clients.

What if I want to cancel the service?

We hope you'll find our services valuable, but we understand circumstances can change. You can cancel our services at any time with no long-term commitment or cancellation fees. We'll assist you in transitioning your accounts if needed.

Are you a dog person or a cat person?

Woof. I mean… no comment. (Just kidding, I love cats too, but I’m quite allergic!)