A Non-Political Takeaway From All the Politics
Entrepreneur Office Hours - #257
In the spirit of being topical but not political, I feel obligated to discuss an important lesson about entrepreneurship exposed by the election. Specifically, I want to discuss attentions vacuums.
For a bit of context, earlier this week I worked with a founder preparing to leverage a partnership with a prominent influencer in his market. He showed me the videos they’d created together, and I thought they were great, but they weren’t particularly timely, so I assumed he had enough sense to know not to post them right away.
Why not post a great piece of marketing content when you have it?
Because, no matter what happened, the election was going to cause a giant attention vacuum. He didn’t consider this, posted his video, and, unsurprisingly, they got almost no traction.
Remember, when major events dominate the headlines, everything else gets sucked into the background. You could have the most insightful, groundbreaking, world-changing announcement ever, but if you post it during a moment like this, it’s like whispering into a tornado — no one’s going to hear it.
Entrepreneurs often underestimate the power of timing. They think that if the thing they’ve built is good enough, people will pay attention no matter what. But that’s not how attention works. Attention is finite, and in the world of business, you’re constantly competing for it. Big events — like elections, global crises, or even a blockbuster movie release — create attention vacuums that pull everyone’s focus, leaving everything else virtually invisible.
In other words, when planning your big announcement, don’t just think about what you’re saying; think about when you’re saying it. In business, as in politics, timing can make or break your impact. Knowing when to speak up — and when to wait for the right moment — is one of the most underrated skills for building a brand people will actually notice.
Podcast: ThoughtWave Episode #3
How Entrepreneurs Can Embrace the Expanded Holiday Season, Sell to Their Customer's Customers, and Embrace Niches
Dr. Dinin and Chris try to understand why the winter holidays have expanded to Halloween and make an argument for why entrepreneurs should embrace it just like Home Depot did. Then they explore the value of selling to your customer's customer as a hack for creating stickiness in your product. They end on a thought wave about the Washington Post's decision not to endorse a presidential candidate and how it relates to the value of targeting niche's versus trying to sell to everyone.
Listen now on: Apple | Spotify | Online
This week’s new articles…
I Was Wrong About Launching Startups Straight Out of College
Maybe it’s time to rethink the common wisdom about whether aspiring entrepreneurs should work for someone else.
To Win at Startups, You’ll Need to Defeat the Entrepreneur’s Biggest Enemy
The scariest parts of entrepreneurship are easy to avoid, but that’s not necessarily a good thing.
Office Hours Q&A
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QUESTION:
Hello Aaron,
I have a difficult question I’m worried about asking people close to me, but I figure I can ask you. You are welcome to share it with your readers, too. But just please leave me anonymous.
I have run into a difficult situation with my startup and I fear we might not be able to get through it despite having been decently successful for the past four years.
What I’m wondering is that I’m finding it hard to determine how transparent I should be with my team about the challenges we’re facing. I want to keep morale up, but I also don’t want to hide the reality of our situation. What’s your take on balancing transparency with optimism in a startup?"
Thank you, in advance, for your insights,
Anonymous
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I know you’re navigating a difficult situation, but hopefully you can at least a little comfort in the fact it’s also a situation that’s incredibly common in the startup world — even for companies that seem outwardly successful. In other words, know you’re not the only founder facing this particular dilemma.
As the founder, you’ve got two main responsibilities here: protecting the morale of your team and being honest about your current challenges. Balancing these two responsibilities is tricky because too much transparency can create anxiety, but too little transparency can lead to a breakdown of trust if the truth eventually comes out (which it almost always does).
My approach in these situations is to focus on constructive transparency. You want to share enough of the reality that your team understands what’s happening, but you also want to present a clear, optimistic path forward. For example, instead of just saying, “We’re in a tough spot,” frame the conversation around, “Here are the challenges we’re facing and here’s what we’re doing to tackle them.” Emphasize the plan and the actions you’re taking to steer the ship through the storm.
One of the biggest mistakes founders make is trying to shield their teams from the truth. But people are usually more resilient and adaptable than we give them credit for. Being open with your team shows respect for them and their roles in the company, and it’s a chance to bring them closer to the mission while inspiring them to help find solutions. Just be careful to avoid oversharing unnecessary details that might lead to unproductive worry. Keep the focus on actionable information and next steps.
Also, as a bit of a practical tip, be sure to check in with your team after you’ve shared the information. Gauge their response, see what concerns they have, and be prepared to adjust your communication style if necessary. Doing this helps open up a conversation where your employees feel like part of the solution.
Ultimately, your team doesn’t need a perfect leader; they need a leader who’s willing to be real with them, someone who’s both honest about the challenges and confident about the path forward. I realize striking the right balance is tricky, but leaning into constructive transparency is one of the best ways to build trust and keep morale strong — even when the future is uncertain.
Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer!