Is "Over Communicating" a Real Thing?

Entrepreneur Office Hours - Issue #281

I had a text exchange earlier this week with a student I'm helping on a summer project. After sending me a string of thoughtful questions about our work, he followed up with a quick, self-conscious apology: "Sorry for all the messages!"

My immediate reply: "NOOOOO... don't apologize! Questions are great!"

I wasn't just being polite. I genuinely meant it. And the more I've thought about his apology, the more I've realized it touches on one of the biggest sources of friction in entrepreneurship — and, really, in life: poor communication.

The vast majority of problems I see entrepreneurs encounter aren't due to a lack of skill, talent, or hard work. They're not due to flawed strategies or even market conditions. Instead, they're almost always a direct consequence of communication breakdowns. Misunderstandings between co-founders, unclear expectations with employees, poorly communicated goals with customers or investors — these are the issues that consistently sink promising startups and good ideas.

In other words, communication isn't some minor detail or afterthought in entrepreneurship. It's the foundation. It's the glue holding everything else together. The most successful founders I know aren't necessarily smarter or more talented than their peers. They're just incredibly good communicators, and they're relentless about clarifying assumptions and expectations.

This means the instinct my student had to apologize for asking too many questions was exactly backward. When you're collaborating, leading, or building something meaningful, the problem is never that someone is communicating too much. The real problem is usually that people aren't communicating enough.

The next time you're ever hesitant about asking another question, sending another update, or seeking clarification, remember this: asking more questions doesn't indicate confusion or incompetence. It’s actually the opposite. It signals care, curiosity, and a commitment to getting things right. And those are exactly the kind of qualities that lead to entrepreneurial success.

-Aaron

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This week’s new articles…

Why The Best Entrepreneurs Don’t Worry About Building Products

Hint: It’s actually because they’re so focused on building something much more important.

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How to Job Hunt Like an Entrepreneur

Entrepreneurial thinking can be a huge asset in a challenging job market… even when it comes to simply getting a job!

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Office Hours Q&A

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QUESTION:

Hey Aaron,

Just curious – what’s your take on startup accelerators? I’ve been debating whether to apply to one, but I’m not sure if it’s worth giving up equity at such an early stage. Do you think the mentorship and network really justify the cost, or are there better ways to get that support?

-Nadia

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Ah yes… startup accelerators: The magical startup machines where you apply, get accepted, hand over some equity, and then three months later emerge with a world-changing business, a full cap table, and a standing ovation from investors.

Except… no… that’s not how it works.

I write this as someone who’s done not one, not two, but three startup accelerators — a.k.a. the entrepreneurial equivalent of repeating the second grade three times, meaning I’ve at least seen the inner workings up close and feel somewhat qualified to give a meaningful answer.

The thing you need to understand about accelerators is they’re not magic. They’re businesses that sell a product — access, mentorship, a little money, and a whole lot of promises — in exchange for equity. That doesn’t make them bad. It just means you need to treat them like any other vendor or service provider. You don’t just ask, “Do I want this?” You ask, “What exactly am I getting, and is it worth what I’m giving up?”

The real answer to that depends almost entirely on you. Accelerators don’t magically make startups better. They give you tools and opportunities, but you have to be the one who turns those things into actual value.

Want to meet investors? You’ll need to hustle for those intros. Want great feedback? You’ll need to chase mentors down and ask smarter questions. Want to grow your business? They won’t do that for you either.

Beyond remember you’re responsible for the value you extract from an accelerator, I’ll also mention the importance of choosing your accelerator wisely. The more prominent and well-resourced the accelerator, the less uphill work you’ll have to do to extract value. A program like Y Combinator or 500 Startups isn’t going to guarantee your success, but it’ll put you in rooms (and email threads) that a smaller, regional accelerator can’t. Those programs can fast-track credibility, put your startup on radar screens that would otherwise take you years to reach, and dramatically expand your options. That’s not nothing.

If you’re considering a less well-known accelerator, you’ll need to lean harder into evaluating what the program actually provides. Who are the mentors? What’s the investment, and on what terms? Will they help you get customers, not just investors? Are the alumni doing well or still stuck repeating the same growth milestones over and over?

Like so many resources in the early startup world, the best accelerators amplify momentum. But they don’t manufacture it. If you’re already building something with traction, a good accelerator can add fuel. If you’re hoping an accelerator will build your business for you, that’s probably equity better spent elsewhere.

Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer.