Watch the Full Video
What does building wealth really mean beyond making money? And how can business owners ensure that years of hard work translate into lasting financial security and a meaningful legacy?
On this episode of Homegrown Hustle, host Matt Eickman sits down with Stacy Kupsky, Co-Founder of Wayzata Bay Private Wealth Management, to explore the intersection of entrepreneurship, purposeful wealth building, and long-term financial planning.
Stacy shares her journey from marketing and working alongside small businesses to becoming an independent wealth management business owner. Drawing from more than a decade of entrepreneurial experience, she explains why building wealth requires more than growing revenue. It takes intentional planning, strong relationships, risk management, tax efficiency, and a clear understanding of what matters most.
The conversation explores her approach to the purposeful architecture of wealth, the importance of planning with the end in mind, and why successful entrepreneurs need to think beyond their next financial milestone. Stacy also shares how her definition of hustle has evolved from relentless grinding to focused, strategic work that aligns with personal values.
KEY TAKEAWAYS:
Build Wealth Around Your Values: Financial success should reflect your vision, priorities, and what matters most to you and your family.
Think Beyond Making Money: Building wealth is about what you keep, how long you keep it, and what you ultimately do with it.
Build a Business That Rewards You: Entrepreneurs should create financial structures that allow their businesses to support their personal and family goals.
Know When to Delegate: Sustainable growth requires recognizing your strengths, finding complementary talent, and trusting others to carry the baton.
Plan for the Unexpected: Protect yourself, your business, and key employees through thoughtful risk management and contingency planning.
Understand Cash Flow and Taxes: Strategic financial planning can help business owners make informed decisions about reinvestment, leverage, and tax efficiency.
Start With the End in Mind: Whether your goal is selling your business, passing it to the next generation, or creating financial independence, planning ahead matters.
Hustle With Intention: Real progress isn’t about working harder every day. It’s about focusing on the work that matters, setting boundaries, and playing to your strengths.
CHAPTERS:
00:00 – Welcome to Homegrown Hustle
00:54 – Stacy’s Early Years and Work Ethic
04:25 – Finding Her Career Path
07:16 – Lessons From Small Business
09:22 – Finding Purpose in Wealth Management
10:41 – From Employee to Business Owner
11:21 – Running a Business Like a Relay Race
12:20 – Building the Right Team
14:22 – The Journey to Independent Wealth Management
14:53 – Building Trust Through Service
16:14 – Financial Lessons for Entrepreneurs
16:46 – The Purposeful Architecture of Wealth
19:00 – Why Business Owners Need a Guide
20:12 – Managing Risk as Your Business Grows
21:42 – What You Make vs. What You Keep
22:01 – Retirement Is a Journey, Not a Destination
23:03 – The Emotional Side of Money
26:07 – Finding the Right Financial Advisor
28:26 – Planning Your Business Exit
30:20 – Beginning With the End in Mind
30:58 – The Six Pillars of Wealth Planning
31:12 – Values, Integrity, and Service
33:43 – Portfolio Design and Investment Strategy
34:18 – Risk Management and Contingency Planning
35:52 – Cash Flow Planning for Business Owners
37:14 – Estate Planning and Building a Legacy
37:31 – Tax Strategy and Wealth Preservation
39:38 – Building a Balanced Retirement Strategy
40:16 – Managing Business Loans and Leverage
41:31 – Taking Emotion Out of Financial Decisions
42:18 – Business Growth and Work-Life Harmony
44:08 – Staying Curious and Continuously Growing
45:46 – Stacy’s Definition of Strategic Hustle
46:26 – Boundaries and Sustainable Success
47:35 – Redefining What Hustle Means
47:50 – Final Thoughts and Where to Connect
GUEST RESOURCES:
Linkedin: https://www.linkedin.com/in/stacykupsky/
Website: https://www.wayzatabaypwm.com/
