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Knowing When to Pivot

We pivoted Buddy Media three times before it worked.

First, we built a social network for brands. Killed it.

Then, a Facebook app builder. Killed it.

Finally, we landed on a social media management platform — the one that eventually sold to Salesforce for $745 million.

But that last pivot, the shift to SaaS in 2009, almost broke us.

Not financially. Emotionally.

I (Kass) still remember sitting in the board meeting where we were discussing the change. Mike and the board were right… recurring revenue was the path forward. I knew it in my head.

But my body didn’t get the memo.

Halfway through the meeting, I had to leave the room. I was on the edge of a panic attack. Not because I disagreed with the decision, but because I understood what it actually meant.

Everything would have to change. Not just the product, but how our teams were organized. How we communicated with clients. How processes worked. Whether we even needed all the people on the payroll.

A pivot isn’t just a strategy shift. It’s an identity shift. And that’s terrifying.

The Three Options

When things aren’t working, you really only have three choices:

1. Keep doing more of what isn’t working
   
2. Fold the business
   
3. Stop, create a new plan, and change direction
   

Option three, the pivot, is the hardest. It requires insight, fearlessness, and humility all at once. You have to recognize that your original plan was wrong, let go of the ego that’s screaming at you to stay the course, and convince others to jump with you into the unknown.

Most founders struggle with this because of fear.

I can’t switch to Y when I raised money to do X.  
I don’t have the skills at the company to pivot to Y.  
I’ll be ridiculed if news of our pivot leaks.  
I can’t lay off a great team that finally gelled.

These fears are real. But they lead to paralysis. And paralysis, more than competition, is what kills companies.

The Question That Unlocks Action

I (Mike) ask founders one simple question when they’re stuck: What’s the worst thing that can happen if you do this?

Usually, the worst-case scenario isn’t that bad — and it beats the alternative: continuing to do what’s not working until you run out of money.

Courage doesn’t come from eliminating fear. It comes from acting despite it.

After I (Mike) nearly died at nineteen, flatlining at my doctor’s office before emergency heart surgery, I started asking that question constantly. What’s the worst that can happen? It reframed everything.

The Signals

So how do you know when it’s time to pivot?

Two signals we look for:

1. You’re consistently missing your success metrics. Not a bad quarter — a pattern.
   
2. You’re in danger of running out of money. If the path isn’t sustainable, it’s time to change.
   

When both are true, it’s not a question of whether to pivot — it’s a question of how fast.

A Question to Sit With

Is there something in your business right now that you know isn’t working — but you’re holding onto because of fear, ego, or loyalty to the original plan?

The companies that make it aren’t the ones that never pivot. They’re the ones that pivot fast enough to survive.

Love,

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INSIGHT

🎯 Authenticity Wins — The founders who stand out aren’t performing, they’re being themselves.

🤝 The Secret to Scaling Is Your Team — Growth comes from the right people.

🔄 It's Time to Pivot — Missing metrics + shrinking runway = signal.

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FOUR FAVORITE FINDS

👟 Allbirds Ditches Shoes for AI

🛠️ Vibe Coding Will Kill Some Software Companies

📦 Supply Chain Chaos

🤖 OpenAI Pivots Toward Enterprise

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AROUND THE FARM

🎙 Scaling, Exits, and the AI Era

🏆 Why Success Can Be a Trap

🤑 Money Mindset Deep Dive

😯 The Full Journey

♟ Startup Execution