Podcast

How Do I Start a Business After 50? | DON'T Get a Partner Until You Watch This! | Part 2 of 4

Here's The Deal Saturday Aug 29, 2026
Episode Overview

What can kill your business faster than a bad market? A bad partner. Starting a business after 50 can be one of the most rewarding things you ever do — but if you're thinking about bringing a partner into the picture, there are some things you better understand BEFORE you shake hands and start splitting everything 50/50. 

This is Part 2 of our four-part series on starting a business after fifty, and we're taking the conversation somewhere a lot of people don't want to go: partnerships, money, ownership, responsibility, communication, and protecting what you've worked so hard to build. 

For this episode, I'm coming to you from Twisted Italian in Peoria, Arizona, where I sit down with owner Brian Bojanowski. Brian made his career change at 45. He went from being a Vice President of Finance at American Express to owning a restaurant — one of the toughest businesses you can get into. Eleven years later, he's still going strong, and Twisted Italian has been voted Best Italian Restaurant in Peoria for six years. His story is another example of what this series is all about: 

Bet on yourself. Work your ass off. Learn along the way. And don't be afraid to change direction. 

But then we get into the other side of entrepreneurship... Partnerships. 

I've spent 30 years in the banking industry, and I've seen partnerships go bad in just about every way imaginable. Best friends. Marriages. Brothers and sisters. Parents and children. People who swore they would never let money come between them. And then the money started talking. 

As Dave Ramsey says, "The only ship that doesn't float is a partnership." 

Whether you agree with that or not, there's a lesson behind it: don't build a business partnership on a handshake, a napkin, or a conversation over a couple of drinks. In this episode, we talk about: 

Why a 50/50 partnership isn't automatically fair 

The importance of a well-structured operating agreement 

Clearly defining each partner's responsibilities 

What happens when one partner puts up the money and the other brings the idea 

Why your intellectual property has value 

Why communication can make or break a partnership 

Why your spouse or family needs to understand what's happening in your business 

The importance of having an exit strategy 

Key-person insurance and protecting the business from unexpected changes 

What happens when a partner dies or leaves the business 

Why bringing in an investor may not always be the best answer 

The difference between borrowing money and giving away ownership 

Why growing slower may actually be better than giving away control 

Playing to your strengths instead of trying to do everything yourself 

And why you need to protect the business you've worked so hard to build

 The big takeaway? Before you go into business with somebody, have the hard conversations first. What are their responsibilities? What are yours? Who puts up the capital? How are profits divided? Who makes decisions? What happens if someone stops working? What happens if someone wants out? What happens if someone dies? What happens if the relationship falls apart? If you can't have those conversations before you start the business, you're probably not ready to be business partners. And here's your homework for this episode: If you already have a partner — or you're considering one — start drafting your operating agreement. Put the expectations on paper. Then sit down together and see what you both agree to. Because you didn't get this far in life without learning a few things. Protect yourself. 

Protect your business. Protect your future. And remember — the best time to start a business was years ago. The second best time is right now. 

Chapters 0:00 — Recording From Twisted Italian 

2:09 — Brian's Journey From Corporate America to Business Owner 

4:18 — The Reality of Starting a Business After 40 

6:41 — Building a Business Around Your Passion 

8:51 — The 50+ Advantage & Why It's Not Too Late 

11:10 — The Partnership Problem 

13:35 — Why Your Operating Agreement Matters 

15:53 — Money, Ownership & The 50/50 Myth 

18:37 — Communication With Your Spouse & Business Partners 

20:28 — Why I'm Cautious About Investors 

22:49 — Debt vs. Giving Away Ownership 

24:48 — Protecting Your Business & Your Legacy 

27:09 — Homework: Draft Your Operating Agreement 

Thanks to Brian Bojanowski and Twisted Italian for letting us shoot this episode at their restaurant. If you're in the Lake Pleasant / Peoria, Arizona area — or you're from Chicago and looking for a little taste of home — check them out. Subscribe for Part 3, where we keep digging into what it really takes to start, build, and grow a business after 50. New episodes from HTD Media. Get Seen, Heard, Remembered. 

 

#HTDMedia #StartABusiness #BusinessAfter50 #Entrepreneurship #EntrepreneurOver50 #SmallBusiness #BusinessPartnership #BusinessOwner #StartingABusiness #EntrepreneurshipOver50 #BusinessAdvice #LegacyBusiness

 


 

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