Podcast hour

If you’re a founder and you haven’t tried Bolt, you’re missing out.

Bolt has totally reimagined what’s possible for startups to achieve. You can take a half-baked idea from your morning meeting and transform it into a fully working prototype by the afternoon.

And why stop at a prototype? You can launch full-scale websites, apps, and everything in-between.

Most vibe coding tools promise speed, but behind the scenes are built on fragile infrastructure, and broken integrations. Bolt changes that.

No external subscriptions. No fragile plugins. No friction. And no coding experience required.

Start building with Bolt.new.

Every now and then I’ll listen to a podcast where I can’t help but pull out my notes app and jot down some insights.

Last week Ben Horowitz joined Lenny’s Podcast and I ended up filling an entire page of notes. I recommend giving the full podcast a listen, but in the meantime, here are my 5 takeaways from the episode… plus some of my personal anecdotes.

Building a company is full of uncertainty and difficult decisions. Oftentimes CEOs are stuck between two terrible options with no obvious answer.

Ben took Loudcloud public with just $2M in revenue, which was famously dubbed “the IPO from hell.” He was mocked endlessly for the decision, but the alternative was to do nothing during a time when capital was drying up in the private markets.

He knew that going public was a terrible decision, but it was the least bad decision at the time, so he took action. Loudcloud eventually sold for $1.6B, while the majority of companies during that period were wiped out in the dot com bubble. Those other CEOs hesitated, and paid for it.

When a leader hesitates to make a decision, it adds uncertainty throughout the entire organization. The team isn’t oblivious — they are aware of the issues. The longer those issues go unaddressed, the less faith they’ll have in the CEO as a leader.

From personal experience, this is most apparent when dealing with an underperforming employee. Exceptional companies are made up of exceptional people, and the bar should remain high. When someone is underperforming, it slows others down and impacts the mentality and buy-in of the entire team.

A-players begin to wonder whether or not that level of output is acceptable, or may even subconsciously regress themselves. “Why am I always up late working so hard while X person is putting in half the effort… and is still here?”

Firing people sucks. It requires lots of difficult conversations. You’ll often experience an immediate setback in output and need others on the team to take on more responsibilities. Then you’re stuck spending weeks (or months) interviewing and hiring to backfill a position you already had on the team.

But the best CEOs don’t hesitate to make the move; the alternative is much worse. Keeping an underperforming employee around is insidious and can degrade the culture and output of the entire company.

Instead, they find people who make them (and the company) great.

Ben calls this managerial leverage, and he contrasts the VP of Engineering with the CEO to make his point.

The VP of Engineering is supposed to teach new skills and develop their team to become better engineers. That’s their job.

But the CEO shouldn’t be able to teach the VP of Engineering how to become a better VP of Engineering. The same way the CEO likely can’t teach the CFO to be better at FP&A, or the CMO to build more effective marketing campaigns.

The company can’t afford to have the CEO spend time developing people. And they likely couldn’t make an average CMO a world-class one, even if they tried.

Ben argues that if the CEO is the one who is telling the department leads what to do next, then they have no leverage. Rather, leverage is when the leads are telling the CEO what to do and how they’re pushing the company forward.

That’s how you know you’re getting more than if they weren’t there.

I absolutely loved that frame of reference.

I’d also go one step further and argue that you should never be in a situation where the company is unanimously in agreement. I think confrontation is incredibly undervalued.

When employees are confrontational, it means they are vocally opinionated about something. It means that multiple sides are being discussed and considered.

That’s how you ultimately land on a better solution. I think leadership is being able to make space for confrontation, and being able to make a decision without consensus.

Ben shared the story about a16z investing in Adam Neumann’s new company, Flow.

The investment resulted in tons of criticism and negative press for backing Adam after the WeWork bankruptcy. But Ben thinks it might be one of their best investments. Rather than harp on Adam’s mistakes, he credits him for his charisma and creating what is arguably the most recognizable name in all of commercial real estate.

Morning Brew had a WeWork office at 85 Broad Street, which was also WeWork’s HQ at the time. One day I was standing next to a tall barefoot guy in the bathroom who was screaming into his phone in Hebrew. I realized about ten minutes later that that was Adam.

That story has absolutely nothing to do with the podcast.

I’m blanking on the other podcast I was listening to, but I believe it was either Steve Jobs or Elon who had stories about hiring exceptionally talented people who were terribly difficult to work with. I think there’s a throughline there to what Ben was trying to convey.

Everyone has their faults, and we’ve all made plenty of bad decisions. It may require overlooking people at their worst to identify opportunities with asymmetric upside.

There’s nothing easy about building a company. You’re going to screw things up, but you have to maintain your confidence.

This is pretty much the theme of Ben’s first book, The Hard Thing About Hard Things. For those who haven’t read, here’s a summary from ChatGPT:

Ben Horowitz argues that building and leading a startup is brutally difficult because there are no perfect formulas—just messy, high-stakes decisions under uncertainty. His central lesson is that great CEOs aren’t those who avoid problems, but those who navigate crises, make tough calls, and keep going when no easy answers exist.

Relying on advice from talking heads on X, podcasts, or newsletters not named Big Desk Energy isn’t going to solve your problems. Founders often have to go through the struggle, pain, and failure to learn these lessons themselves.

And I’ve personally made a million of them. Half of my posts are about times that I had fucked up — like this one here, here, and here. But I’m hopeful that those experiences can at least be useful (or entertaining) for others to learn from.

This was my first time breaking down a podcast that I enjoyed in newsletter form.

If you enjoyed it: reply with a “👍”
If you hated it: reply and tell me why

And if you want to listen to the full episode, I highly recommend it.

If you enjoyed this post or know someone who may find it useful, please share it with them and encourage them to subscribe: mail.bigdeskenergy.com/p/podcast-hour

Shoutout Megan for the reader submission. A+ view with a D+ office chair.

Think you can generate a better office? Reply with your submissions 📨.

Turn on, tune in, drop out. Click on any of the tracks below to get in a groove — each selected from the full Big Desk Energy playlist.

Some of my favorite content I found on the internet this week…

Chat with DenkBot — my AI clone. It’s trained on everything I’ve ever published and the entire beehiiv knowledge base 🧠.

It’s also trained on my voice, which means you can call it and have full conversations. Give it a try and let me know what you think.

Share this newsletter with your friends, or use it as a pickup line.

👉 Your current referral count: {{ rp_num_referrals }} 👈

Or share your personal link with others: {{rp_refer_url_no_params}}

📥 Want to advertise in Big Desk Energy? Learn More