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Tyler A Bolla

Advisor at Hilltop Wealth & Tax Solutions — Chicago, IL

Updated today

Credentials

CFP®, Series 63, Series 66

Experience

10 years

Location

Chicago, IL

Hilltop Wealth & Tax Solutions

Team

Total advisors

9

Across 5 offices

Clients per advisor

92 High

Avg AUM per client

$738,005 Low

HNW client ratio

23% Low

About

Tyler Bolla is a CFP® professional with 10 years of industry experience. He is currently with Hilltop Wealth & Tax Solutions and has previously worked at Charles Schwab, Bank of America, and Merrill. Hilltop Wealth & Tax Solutions serves individual and institutional clients with integrated financial planning, tax planning, and discretionary portfolio management that incorporates tax and estate considerations. The firm offers customized investment strategies and combines advisory services with affiliated tax and bookkeeping capabilities.

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 Retirement income strategy General estate planning guidance Tax-loss harvesting

Occupation focus

Based on Hilltop Wealth & Tax Solutions

Founder/Business Owner Executive

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Fee options

Fixed

Financial planning fixed fees negotiated, typically ranging from $1,200 to $20,000 annually depending on complexity

Percentage

$0 - $250,000: 1.50% $250,001 - $750,000: 1.00% $750,001 - $1,500,000: 0.90% $1,500,001 - $3,500,000: 0.80% $3,500,001 - $5,500,000: 0.60% $5,500,001 - $10,500,000: 0.50% $10,500,001 - $25,000,000: 0.40% $25,000,001+: Negotiable

Commissions

Hilltop Wealth professionals may receive commissions for insurance product sales; some advisory professionals are registered representatives and may receive commissions on securities transactions (with restrictions)

Project-based

Financial planning hourly rate at $250/hour for clients with less than $500,000 AUM

Other

Account minimum: $417,000 Minimum fee: Minimum total annual fee of $6,250 (may be waived at firm's discretion) Fee-only: Financial planning fees for clients with less than $500,000 AUM negotiated at $250/hour; fixed fees range from $1,200 to $20,000 per year

Location

See office

Chicago, IL

Chicago IL

Advisors at this office

1

Most active in

Illinois

Work history

10 years of industry experience

Hilltop Wealth & Tax Solutions

2026 - Present • 1 year

Chicago, IL

Charles Schwab

2021 - 2026 • 5 years

Chicago, IL

BANK of AMERICA, N.A.

2018 - 2021 • 3 years

Rolling Meadows, IL

Merrill

2018 - 2021 • 3 years

Rolling Meadows, IL

Charles Schwab

2015 - 2018 • 3 years

Indianapolis, IN

Disclosures

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

Business activities & affiliations

Vincent D

CFP®, Series 65

Chicago, IL

RISE Investment Management, LLC

Vincent DeCrow is a financial advisor at RISE Investment Management, LLC (dba RISE Investments) with 7 years of direct industry experience. He holds the Series 65 designation and has worked at RISE since 2019, following roles at Origin Investments and Duff & Phelps, LLC. RISE Investments provides discretionary investment management and financial planning services to individuals, high-net-worth clients, families, trusts, businesses, retirement plans, and non-profit organizations. The firm emphasizes long-term equity ownership, tax efficiency, and diversified portfolio construction, offering access to private placements and manager-of-managers solutions.

Private / alternative investments Real estate investing Tax-loss harvesting Retirement withdrawal strategies Cash flow / budgeting Founder/Business Owner Executive Retired Consultant Real Estate Professional Mid-Career Professionals HENRY (High Earners, Not Rich Yet) Retired Approaching retirement Established Professionals
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Brady L

Series 65

Chicago, IL

RCM Wealth Advisors

Brady Lawrence is a financial advisor at RCM Wealth Advisors with a Series 65 credential and four years of industry experience. He has worked at RCM Wealth Advisors since 2022 and is also involved with RCM Ag Services and Strategic Trading Advisors, where he specializes in commodities hedging and agricultural market research. Prior to his advisory roles, he attended the University of Mississippi. RCM Wealth Advisors is a multi-advisor SEC-registered firm managing approximately $324 million for around 530 clients, including individuals, pension plans, and corporate clients. The firm uses a combination of fundamental and cyclical analysis, supported by an internal Investment Policy Committee, and offers tailored portfolio management with both discretionary and non-discretionary account options.

Options & derivatives strategies General retirement planning Retirement income strategy Wealth management Retirement plans for business owners (SEP, solo 401k)

Jared G

Series 65, Series 66, Series 7, RICP®

Chicago, IL

Stirlingshire Investments

Jared Goldstine is a dedicated financial advisor at Stirlingshire Investments, bringing 8 years of hands-on industry experience to help clients achieve their financial goals with confidence and clarity. He holds the Series 7 license and is a Retirement Income Certified Professional (RICP). Jared has built his expertise at respected firms including Park Avenue Securities, Guardian Life Insurance Company and Northwestern Mutual. In addition to his professional work, Jared serves as Vice President of First Choice Networking Group, a professional networking organization, where he volunteers his time to connect business leaders and foster meaningful relationships in the community. Stirlingshire Investments is a forward-thinking wealth management firm on the leading edge of AI and technology in the financial services industry. We deliver discretionary portfolio management to individuals, trusts, families, and institutions — serving both non-high-net-worth and high-net-worth clients with sophisticated, personalized strategies. By combining deep human expertise with advanced AI-powered analytics, machine learning models, and cutting-edge technology platforms, Stirlingshire provides a significant edge in portfolio construction, risk management, and opportunity identification. Our team utilizes multiple analytical methods and offers a broad range of investment solutions, including mutual funds, ETFs, fixed income, REITs, private placements, and venture/alternative vehicles. At Stirlingshire, we believe the future of wealth management belongs to those who intelligently merge proven financial principles with the most advanced tools available. Jared Goldstine and the entire team are committed to delivering innovative, technology-enhanced investment solutions tailored to each client’s unique objectives, risk tolerance, and timeline.

Long-term care insurance Active portfolio management Wealth management Tax-loss harvesting General retirement planning Scientific Professional Retired Doctor or Medical Professional Executive Mid-Career Professionals Established Professionals Approaching retirement Retired

Duke L

Series 66, Series 7

Chicago, IL

CIBC Private Wealth Advisors, Inc.

Director of Private Funds focused on alternative investment product strategy, capital formation, and platform leadership. Lead the development, commercialization, and governance of private market solutions across private equity, private credit, hedge funds, infrastructure, and co-investments. Partner with investment and distribution leadership across a $100B+ platform serving institutional, family office, private wealth, and international clients. CIBC Asset Management and CIBC Private Wealth Advisors provide investment advisory and wealth management services to individuals, families, trusts, employee benefit plans, corporations, and investment companies. The firm combines internal teams and committees to deliver customized portfolio management and offers access to specialized strategies, including options hedges and structured notes, with a notably high assets-under-management per advisor ratio.

Options & derivatives strategies Private / alternative investments Active portfolio management Wealth management Financial Professional
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Richard S

Series 63, Series 65

Chicago, IL

SRC Capital Management

Richard Smith is the founder, CEO, and Chief Investment Officer of SRC Capital Management, an independent investment advisory firm based in Chicago, IL. He holds Series 63 and Series 65 credentials and has over 20 years of industry experience. Alongside his advisory work, he has taught at multiple universities, including DeVry University, Southern New Hampshire University, Chicago Public School District 299, Argosy University, and University of Phoenix. SRC Capital Management provides discretionary investment management services to individuals, nonprofit and for-profit entities, endowments, pension plans, and government clients. The firm employs a fundamental, bottom-up value investing approach focused on under-owned and under-researched domestic equities, with an emphasis on stock selection and sector diversification to manage downside risk.

Active portfolio management Wealth management
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Wander C

Series 65

Chicago, IL

Golden Foundation Advisors

Wander Cedano is a financial advisor with Golden Foundation Advisors in Chicago, holding a Series 65 designation and three years of industry experience. His prior work includes roles at RWA Wealth Partners, Adviser Investments, and the Federal Reserve Bank of Boston. Golden Foundation Advisors is an independent, fee-only firm providing financial planning and investment management services to individuals and high-net-worth clients. The firm emphasizes passive investment construction through diversified funds and uses an institutional custodial platform with discretionary trading and semi-annual account reviews.

Business ownership considerations Business exit / sale strategy Cash flow / budgeting College savings (529s, UTMA, etc.)
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