Why Entrepreneurs Struggle to Retire (and How to Fix It)

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The Executive Connect Podcast

120 episodes

2 days ago

This is the Executive Connect Podcast - a show for the new generation of leaders. Join us as we discover unconventional leadership strategies not traditionally associated with executive roles. Our guests include upper-level C-Suite executives charting new ways to grow their organizations, successful entrepreneurs changing the way the world does business, and experts and thought leaders from fields outside of Corporate America that can bring new insights into leadership, prosperity, and personal growth - all while connecting on a human level. No one has all the answers - but by building a community of open-minded and engaged leaders we hope to give you the tools you need to help you find your own path to success.

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Management

Business,

Entrepreneurship

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Why Entrepreneurs Struggle to Retire (and How to Fix It) | Matt Ruttenberg

The Executive Connect Podcast

26 minutes

2 weeks ago

Why Entrepreneurs Struggle to Retire (and How to Fix It) | Matt Ruttenberg

Entrepreneurs spend years building their businesses but often forget to build their retirement plan. In this episode of Executive Connect, host Melissa Aarskaug sits down with Matt Ruttenberg, co-founder of Life Inc. Retirement Services, to discuss why business owners delay planning for retirement and how to fix it.

Matt explains how to build a retirement plan stack tailored to your business, combining 401(k)s, profit-sharing, and defined benefit plans to maximize tax efficiency and wealth growth. He shares the biggest mistakes entrepreneurs make with their retirement planning, why “set it and forget it” doesn’t work, and how to build a trusted advisory team that communicates effectively to protect your future.

If you’ve ever said “I’ll figure out retirement later,” this episode shows you exactly what to do next — and why waiting could cost you hundreds of thousands in taxes and missed compounding opportunities.

Timestamps:
00:00 Why entrepreneurs delay retirement planning
01:20 The wake-up moment when business owners realize they need a plan
02:25 Building a customized retirement plan stack
04:00 How entity type impacts your retirement options
05:30 The two key questions every business owner must answer first
06:40 How to use retirement planning to reduce taxes
08:10 Pretax vs. Roth contributions explained
09:45 How to reinvest tax savings to accelerate wealth
11:00 Why entrepreneurs need a coordinated financial team
12:15 The “general practitioner” and “specialist” analogy for your financial advisors
13:00 Common 401(k) misconceptions that cost business owners money
14:40 Why cookie-cutter plans fail and custom designs save you thousands
16:00 How to find the right retirement plan partner
17:30 Prototype vs. custom plan documents explained
19:00 What questions to ask before hiring a retirement specialist
20:15 Why ongoing consultation matters as your business evolves
22:00 The hidden fees to avoid and how amendments should work
23:10 The importance of agility as your business grows
24:00 How to prepare for deadlines and optimize timing
25:00 Where to start if you’re ready to take retirement planning seriously
26:00 Final advice for entrepreneurs ready to build lasting wealth

Key Themes:

Retirement planning for entrepreneurs

Business tax strategies and deductions

Building a custom 401(k) plan

Profit-sharing and defined benefit plans

Pretax vs. Roth strategies

Finding trusted financial advisors

Common mistakes in small business retirement plans

Guest Bio:
Matt Ruttenberg is the co-founder of Life Inc. Retirement Services, helping business owners design smarter, tax-efficient retirement plans that align with how entrepreneurs work and grow. His company specializes in custom-built retirement plan stacks that evolve alongside your business.

Connect with Matt Ruttenberg:
Website: https://401k.expert
LinkedIn: Life Inc. Retirement Services

Connect With Us:
Website: www.executiveconnectpodcast.com
YouTube: Executive Connect YouTube Channel
LinkedIn: Melissa Aarskaug
Instagram: @executiveconnectpodcast
TikTok: @executiveconnectpodcast
Facebook: Executive Connect