Following Our Own Entrepreneurial Advice (a.k.a. Eating Our Own Dog Food)
Entrepreneur Office Hours - Issue #309
As most of you know, I’m in the middle of reimagining Entrepreneur Office Hours — not replacing what it is, but expanding it with the insights, experience, and brainpower of my incredible colleagues here at Duke. And as we’ve started planning what that might look like, we’ve hit a very predictable (and very entrepreneurial) problem:
We don’t actually know what you want.
That’s not me being self-deprecating. It’s just the nature of entrepreneurship. To explain what I mean, I’m going to borrow a concept from one of my mentors and colleagues here at Duke, Jon Fjeld, who has a framework he calls the Three Pillars of Entrepreneurship: value, empathy, and uncertainty.
They’re relevant here, so let me break them down quickly:
VALUE:
If Entrepreneur Office Hours isn’t valuable to you — the audience — then nothing else matters.
EMPATHY:
In order to create value, I need to understand you. Not what I think is useful… what you actually find useful.
UNCERTAINTY:
But here’s the catch: I can’t know any of that with certainty. I can guess. I can hypothesize. I can project my assumptions onto you. But none of that is entrepreneurship. It’s wishful thinking.
The entrepreneurial move is to close the uncertainty gap, which is something that gets done do through feedback, testing, and real conversations with the people the entrepreneur is trying to serve.
Which brings me to the point of my message:
I could sit here imagining the content you might find valuable… or I could just ask.
I’m going to do the latter. I have three specific questions. Note, they’re not vague “tell me what you want” questions, because nobody wakes up each morning thinking about what they want in a newsletter. These are targeted questions that will genuinely help us understand how to build something more useful, more delightful, and more impactful for you.
If you’re willing, please hit reply and answer these, or drop your answers in the comments:
Three Quick Questions to Build a Better EOH
1. What other entrepreneurship-related newsletters, podcasts, or creators do you actively follow — and what do you like about them?
(That tells us the style, tone, and format that resonates with you.)
2. When you think about challenges in your current entrepreneurial work (company-building, content, leadership, career, etc.), what topics or skills feel most urgent for you right now?
(This reveals where value is truly needed today.)
3. If EOH added more voices — founders, operators, VCs, researchers, Duke faculty — which perspective would be most helpful for you and why?
(This helps us decide who should show up here.)
As always, thank you for reading — whether you’ve been here since Issue #1 or this is your first. The goal is to build something worthy of your time and attention, and the best way to do that is with you, not just for you.
Looking forward to learning from your answers.
— Aaron
This week’s new articles…
The Hardest Lesson to Learn in Startups
Nothing about startups is easy, but one particularly difficult lesson is also a key lesson every founder needs to understand if they want a chance at success.
One Question That Always Predicts Startup Success
The way a founder answers tells you everything you need to know about what’s going to happen to that company.One Question That Always Predicts Startup Success
Your Big Startup Idea Doesn’t Matter (Until You Do This)
The best entrepreneurs know the difference between the stuff that sounds impressive and the stuff that actually is impressive.
Office Hours Q&A
QUESTION:
Hi Dr. Dinin,
I’ve been following your stuff for a while, and one thing I appreciate is how you make this whole entrepreneurship thing feel a little less overwhelming. So I figured I’d ask something I’ve been struggling with quietly for a while.
How do you talk about your business when it’s still early and not really “successful” yet?
I’ve been working on something that’s still small, and when people ask what I do, I get embarrassed. I either downplay it or make it sound like a side project even though I’m putting real energy into it. Any advice?
-Omni
If I’m being honest, one of the things most entrepreneurs are great at is acting confident.
Whether they actually feel confident is another story, but either way, they get really good at talking big about small things. They puff up the early stages. They pitch like it’s already a unicorn. They say things like, “We just launched” when what they really mean is they bought a domain name.
So the struggle you’re describing of being unsure how to talk about your business because it’s still small… that’s actually rare. Maybe it’s even a good thing.
The truth is, lots of entrepreneurs look successful long before they are. And then they get trapped by their own performance. In other words, they make decisions based on what looks impressive, not what’s actually working. As a result, they tend to optimize for perception instead of value.
That doesn’t seem like you, and maybe that’s great.
By asking the question you’ve asked, it seems to me like you’re focused on the right things. You’re trying to build something real, not just look like you are, and that’s not weakness. It’s the kind of mindset that builds businesses that last.
Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer.





1. Substack, Zero to Pitch Gold, and Medium
2. The value I need most is fundraising help
3. Additional adds to improve. The least needed is to add more Duke Professors (most professors have never been an Entrepreneur), and being a Start-up CEO is vastly different from being a CFO or VP of marketing. They are not programmed to think out of the box, which is a major requirement for start-up CEOs (many years ago, I was an Associate Professor in Ag Economics over in Raleigh at NCSU).
Everyone, including me is a different person doing different creative work.
Hence, I value a wide range of facts and opinions. I can't guess what might give me insight.
That is why I read a number of different articles each day. Your work and those on Medium are extremely valuable.