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"I Wish I Had" Verses "I'm Glad I Did"

There are two kinds of people at the end of their lives. The first group says, “I wish I had.”

I wish I had taken the shot.
I wish I hadn’t waited so long.

The second group says, “I’m glad I did.”

I’m glad I went for it.
I’m glad I made the call.

That’s it. That’s the split.

After decades of life…after all the noise and complexity…it comes down to that simple divide.

And here’s what hit me (Mike) hard listening to Mel Robbins interview Dr. Rahul Jandial, a world-renowned cancer surgeon talk about thousands of patients at the end of their lives…

No one says, “I’m glad I played it safe.”
No one says, “I’m glad I stayed practical.”
No one says, “I’m glad I waited until everything was perfectly lined up.”

They wish they had been bolder.

Now let’s bring this into business. Because the same divide exists.

There are two types of business people.

The first group builds careers or businesses full of quiet regret.

They played defense instead of offense.
They listened to the crowd instead of their gut.
They stayed in something too long…or never started the thing they knew mattered.

They look back and say, “I wish we did that.”

The second group… They’re not necessarily more successful on paper. They don’t win every time. They don’t avoid failure.

But they don’t carry that same weight. Because they acted.

They made the call.
They took the swing.
They followed the instinct when it didn’t make sense to anyone else.
They made bold moves when the optics weren’t right.

And when they look back, they can say, “I’m glad i did.”

Even when it was messy.
Even when it hurt.
Even when it didn’t work out.

Because regret doesn’t come from failure.

It comes from inaction.
It comes from ignoring that internal voice.
It comes from what Dr. Jandial, the surgeon, called “moral injury”…doing something that goes against who you are or not doing something you know you should.

So here’s the question I want you to sit with… Which one are you becoming?

And more importantly… What are you not doing right now in your business that your future self is going to wish you had done?

Not in theory. Not someday. Right now.

The call you’re avoiding.
The decision you keep pushing.
The idea you haven’t greenlit.
The move you know is right but feels uncomfortable.

Because there is no moment of arrival where this gets easier. There’s only a series of moments where you choose.

Only you can make the decisions that determine whether one day you’ll look back and say “i wish i had”…or “i’m glad i did.”

Love,

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INSIGHT

🤝 Bridge the Gap — These are the concrete steps to achieving your vision.

📈 The Worst Business Advice — Never auditing your successes means missing out on growth.

🧑‍💻 Network Isn't Optional — It's the best way to reach investors.

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CHEAT CODE: CHOOSE YOUR COFOUNDER LIKE YOUR SPOUSE

Pick your cofounder like you would pick a spouse.

Not in a romantic sense. This is a survival rule. Who you start a business with matters infinitely more than the idea itself in the early years.

Choose poorly and pride, fear, or different values will eat your idea away.

Talk about the hard things before the money shows up. Money, family, stress, role division, and what failure looks like. Test the relationship with real work. Spend a week on sales together, ship a tiny project, or run customer calls side by side. If you can't share the grind and maintain respect, your partnership will not survive the grind.

Make the relationship legal and simple. Vesting, cliffs, and a founders agreement are not betrayal. They are insurance. Write decision rules now for firing, exits, and tie votes. Agree on non-negotiables like honesty and ownership of the messy work.

Look for complementary muscles and the same moral center. Skill can be learned, stubbornness cannot. Choose someone who will amplify the team, admit mistakes, and do the dirty work when excitement fades.

A cofounder is a long-term bet. Do the diligence, say the unsayable, and sign the paperwork.

You'll sleep better and the company will have a better chance to live.

Want more of our cheat codes? Follow along on Instagram.

🆘 Access the 49 other cheat codes every entrepreneur needs to know from
Shoveling $H!T: A Love Story

🚜 Have you dived into building a business? Jump into the Founders Farm and share some stories.

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FOUR FAVORITE FINDS

📉 We're in a K-shaped economy right now, and it could be worsened by the war in Iran and the surge in oil prices.

🧾 For younger shoppers, discounts are having a larger and larger impact.

💵 A long-running debate over the economics of the minimum wage is still going, even after 30 years.

🥎 This is the story of how a celebrity pickleball coach turned his passion into a brand empire.

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AROUND THE FARM

🤑 We joined Kareen Zahr on her podcast to discuss the money mindset behind our success.

😯 We get retrospective on our path from Golf.com to now on The Dan Evans Show.

🎙 Mike joined Travis Chappell on Travis Makes Friends to discuss what's hot in entrepreneurship right now.

💭 Mike wrote a piece for Forbes on how successful businesses can get stuck.

♟ We sat down with Stifel's Brad Ellis to talk about the tactical aspects of startup success.

🤩 We're honored that the Goody Business Book Awards rewarded our book Shoveling $h!t: A Love Story as a winner in the Entrepreneurism and Small Business categories!

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FINALLY, WANNA GET INVOLVED?

📖 Get bulk copies for your team.
⏰ Invite us to speak at your event.
🤯 Share your thoughts on social: #FoundersFarm

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STAY CONNECTED!
Email: info@kassandmike.com

Follow on LinkedIn:
Kass Lazerow | Mike Lazerow

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Kass & Mike, 1350 Avenue of the Americas, Floor 2, #1043, New York, NY 10019