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Tyler Bolla

Advisor at Hilltop Wealth & Tax Solutions

Updated today

Firm

Hilltop Wealth & Tax Solutions

Location

Chicago, IL

Credentials

CFP®, Series 63, Series 66

Industry experience

7 years

About

Tyler Bolla is a CFP® with seven years of industry experience, currently serving as an advisor at Hilltop Wealth & Tax Solutions in Chicago, IL. He previously worked at Charles Schwab & Co., Inc., Bank of America, N.A., and Merrill. Hilltop Wealth & Tax Solutions is a team advisory firm managing approximately $490 million in client assets across nearly 800 relationships. The firm serves individual and high-net-worth clients, trusts, corporations, and retirement plans, offering discretionary portfolio management, comprehensive financial planning, and tax-related services through an affiliated firm.

Client services

Based on Hilltop Wealth & Tax Solutions

Financial planning Portfolio management Pension consulting Educational seminars or workshops

Expertise

Based on Hilltop Wealth & Tax Solutions

Options & derivatives strategies Concentrated stock management General estate planning guidance Tax-loss harvesting

Occupation focus

Based on Hilltop Wealth & Tax Solutions

Executive

Fee options

Fixed

Negotiated fixed fees for financial planning, ranging $1,200 to $20,000 depending on complexity

Percentage

$0 - $250,000: 1.50% $250,000 - $750,000: 1.00% $750,000 - $1,500,000: 0.90% $1,500,000 - $2,000,000: 0.80% $2,000,000 - $5,000,000: 0.60% $5,000,000 - $20,000,000: 0.50% $20,000,000 - $25,000,000: 0.40% $25,000,000+: Negotiable

Commissions

Possible commissions for insurance products and mutual fund sales via affiliated broker-dealer

Project-based

Approximately $250 per hour for financial planning services if less than $500,000 AUM

Other

Account minimum: $417,000 Minimum fee: $6,250 minimum total annual fee, waivable at firm's discretion Fee-only: Financial planning fixed fees typically $1,200 to $20,000 per year, negotiated; $250/hour for hourly planning for clients with less than $500,000 AUM

Location

Chicago, IL

Most active in

Illinois

Work history

Hilltop Wealth & Tax Solutions

2026 - Present (1 year)

Charles Schwab

2021 - 2026 (5 years)

BANK of AMERICA, N.A.

2018 - 2021 (3 years)

Merrill

2018 - 2021 (3 years)

Charles Schwab

2015 - 2018 (3 years)

Disclosures

Exclamation point means they have disclosures of this type. Check mark means no disclosures of this type were found.

Business activities & affiliations

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Richard S

Series 63, Series 65

Chicago, IL

SRC Capital Management

Active portfolio management Concentrated stock management
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Julia Z

CFP®, Series 63, Series 65

Chicago, IL

Genfi LLC

College savings (529s, UTMA, etc.) Equity compensation tax strategy Options & derivatives strategies Executive
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Brian W

Series 65

Chicago, IL

Bright Lantern Financial LLC

Passive / index investing Tax-loss harvesting College savings (529s, UTMA, etc.) General retirement planning

Brett W

CFP®

Brookfield, IL

Wysopal Wealth

At Wysopal Wealth, we specialize in helping high-income professionals and former athletes manage the complexities of equity compensation and variable income. Our goal is to make sure your money works for you—today and for the future. We focus on creating personalized, values-driven financial plans that allow you to live fully now while planning for what’s next. I’m Brett Wysopal, a proud girl dad of two and a former minor pro hockey player. My experience in sports taught me discipline, focus, and resilience, all of which I apply to financial planning. After spending years navigating the world of equity compensation, I’ve made it my mission to help families simplify their finances, reduce tax burdens, and achieve their life goals. Our approach at Wysopal Wealth is rooted in personalized attention. We keep our client list small, ensuring every client receives the time and care they deserve. We dive deep into your financial situation, understanding your numbers, values, and what matters most to you. This allows us to tailor your financial strategy to your unique goals, whether that’s managing your equity, preparing for retirement, or planning a family legacy. Equity compensation is often the largest part of our clients' wealth, but it comes with complexities—ISOs, RSUs, stock options, and significant tax implications. Many people wait too long to make decisions about their equity, resulting in missed opportunities or unexpected tax bills. At Wysopal Wealth, we take a proactive approach, creating a strategy for when and how to execute your equity plans, minimize tax liability, and diversify your holdings. At Wysopal Wealth, financial happiness is the goal. We believe that money should support the life you want, and we’re here to help you make that happen.

Equity Recipients (RS/RSU, SOP, ESPP) General tax planning Technology Professional Gen Y/Millennials (Born 1980-1995)
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Michael C

Series 65

Chicago, IL

MJC Financial Fitness LLC

College savings (529s, UTMA, etc.) Cash flow / budgeting
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Nauman B

Series 65

Chicago, IL

Old Forge Advisors

Wealth management
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