Start Your Entrepreneurial Journey by Answering This Question
Entrepreneur Office Hours - Issue #317
Inside the Office
A student came into office hours last week with a question that sounded simple.
“When do I start?” they asked.
I asked what they meant.
They smiled, caught, and tried again. This time with the kind of urgency that builds up when you’ve been carrying an idea around too long without doing anything about it.
“When do I start working on my idea for real? When do I start building? When do I stop thinking and actually do something?”
It sounds like a question about productivity. It almost never is. Most of the time, “when do I start?” is really asking something else: How do I know I’m allowed to take this seriously?
So I asked the question I often ask in these moments: “Do you believe in it?”
Not “Is it good?” Not “Will it work?” Just this: do you believe in it enough to treat it like it matters?
They hesitated.
That hesitation is common. Early-stage founders often think belief means certainty. But belief at this stage isn’t certainty, it’s willingness. The willingness to take the question seriously enough to go find the truth, even if the truth turns out to be no.
Once they said yes (tentatively, but yes), the conversation shifted. Not because the answer became obvious, but because the work did.
Here’s what I told them: entrepreneurship doesn’t start with building. It starts with discovery.
Founders love to build because building feels like progress. You end the day with something to point to: a mockup, a repo, a sense of momentum. But building before you understand the customer doesn’t reduce uncertainty. It just makes your guesses more expensive.
If you’re stuck wondering what to work on, it’s usually because you’re trying to build in a vacuum. You’re asking “What should I make?” before you’ve answered “Who is this for?” and “What are they struggling with right now?”
So we rewrote their question together.
Not: When do I start building?
But: When do I start learning?
That reframe changes everything. Once you’re learning, the next steps stop being abstract. Go find people who live with the problem. Ask how they solve it today. Learn what’s slow, expensive, or risky about their current approach. Figure out what happens if they do nothing. Test whether this is a mild annoyance or a problem with real urgency behind it.
And once you’ve found a real customer with a real problem, building feels different. You’re no longer trying to prove you can make something. You’re trying to relieve a pain that already exists.
By the end of office hours, that student didn’t have a prototype. They didn’t have a business plan. They didn’t even have a locked-in idea.
But they had a starting line: three people to talk to, a clearer question to ask, and a definition of progress that didn’t depend on permission.
Entrepreneurship doesn’t start when you feel ready. It starts when you’re willing to take a belief, even a shaky one, and turn it into learning.
-Ryan
Worth Your Time
I get lots of questions asking about the kinds of readings I assign my students. First of all, if I’m being honest, in 2026 I don’t always assign tons of readings. I lean more toward videos and podcasts. But that’s just a sign of the times.
However, one article I’ve been assigning since I first began teaching entrepreneurship in 2015 is Paul Graham’s classic “What You’ll Wish You’d Known.”
Originally published in 2005, this article is over 20 years old. Despite its age, every time I read it, I feel like it inspires me to think differently. In fact, that happened even after I just read it again while preparing this post.
If you’ve never encountered Paul Graham’s essay, take a few minutes, read it, and get inspired to change the way you approach the entrepreneurial world. And if you have read it before… well… go read it again, and get inspired again. It’ll be the best seven minutes you’ve spent today.
Tools We’re Tinkering With
Editor’s note: All resources suggested in this section are based on our opinions. These aren’t affiliate promotions and we don’t generate commissions.
Like many of us, my life is a juggling act. Between teaching, mentoring, parenting, life admin, and generally existing on planet earth, I have a lot of balls in the air at any given moment. To help prioritize, I like to imagine all my to-do's as glass balls and rubber balls. The glass ones will shatter if dropped, while the rubber ones will bounce right over to next week (and usually do..).
So imagine my delight when I discovered Fyxer. My inbox used to be a huge mishmash of glass balls, rubber balls, irrelevant balls, order updates for balls I impulse bought online, advertisements to purchase additional balls I don't need, you get the idea. Fxyer sorts my inbox by priority and categorizes each email with these lovely soothing pastel rainbow labels. My "glass ball" emails are right there at the top (Respond), and everything else descends in order of priority (FYI, Comment, Notification, Meeting Update, Awaiting Reply, Actioned, and Marketing). The best part is, I didn't have to explain to it which balls are made of glass - it just knows.
I haven't let Fyxer take over my calendar yet, but I'll report back if we take the next step.
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This lands. I see founders stuck because “build” feels heavy, but “learn” feels allowed. The moment you talk to real people, momentum shows up. No drama. Just work. 👊
Really solid reframe here. The shift from \"when do I build\" to \"when do I learn\" captures where most early founders trip up. I spent weeks designing mockups for a side project last year before talking to anyone, only to find out the problem wasnt urgent enough for ppl to care. Building before discovery just makes the lesson more expenisve.