Breaking 100

Most business owners insure the trucks, the buildings, and the cyber risk without blinking. Almost none of them insure the people who make the place run.

Jack Leavy has spent 30 years designing executive benefit plans. The main takeaway: you can promise a key employee real money for staying and skip most of the rules that make 401ks so rigid.

Here’s what you'll learn:

→ How non-qualified plans work and why they sit outside the 401k rules

→ The stay bonus. If they stay five years, they get paid. If they leave, you owe nothing.

→ Why 10 to 15% of someone's pay is the number that changes behavior

→ Deferring income at your highest tax rate and taking it at your lowest

→ The math on losing a key employee: 3 to 4 times their pay if the seat sits empty a year

→ Why your buy-sell agreement is only as good as your last valuation

Chapters

0:00 Intro

1:00 Why a retirement plan can protect a business

5:00 What keeps owners up at night

7:55 The dealership that dropped its match

15:40 The five alarm fire and the $100,000 promise

21:20 Save till it hurts. The ski jacket rule.

28:15 The real cost of losing a key employee

34:35 The fine print. Three risks to know.

39:40 Financing your own exit

45:10 Keep it simple, valuations, and Tommy Boy

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This podcast is sponsored by Michigan Retirement Advisors.

https://miretire.com/

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https://pod.link/6812062863

Less than 1% of businesses ever reach 100 employees. We built The Breaking 100 Podcast to discuss what it takes to actually accomplish that massive feat.

My (Evan) first company was a valet business: a golf course, a restaurant, then a hospital system, which grew to over 100 employees and every problem that comes with them. The partnership didn't survive it, and the ending wasn't amicable.

That failure taught me more than the growth did. In 2010 a business partner and I started Michigan 401k Advisors with zero clients... Today it's over 120 401k plans.

Charlie came here from England with a suitcase and a scholarship, went independent, and crossed $100 million in assets. He manages $150 million for 180 families now.

In this episode of The Breaking 100 Podcast, we covered:

→ How a valet company grew past 100 employees and why it fell apart

→ What separates a good 401k plan from a great one

→ Why the Rockefellers stayed wealthy and the Vanderbilts didn't

→ The one guarantee Charlie makes to every single client

→ The emotional math behind retiring, or deciding not to

Every owner who's crossed 100 has a story about what it almost cost them. Those stories are the reason this show exists.

Chapters

0:00 Why we started Breaking 100

4:25 Evan's story, from parking cars to 120 retirement plans

11:57 What makes a 401k plan actually great

16:17 Charlie's road from England to Bloomfield Hills

23:53 Investment manager or wealth manager

29:38 The one guarantee: you will lose money

34:58 Why nobody's met their 401k advisor

51:04 What a 401k says about your company

1:00:44 The two questions every owner should ask

1:05:35 Emotional math and what wealth really means

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This podcast is sponsored by Michigan Retirement Advisors.

https://miretire.com/