-Shep Moyle

A CEO I work with came into a session visibly frustrated. He had a strong product, happy customers, and growing interest in what he was building. And yet, sales were slow, deals dragged, and every conversation seemed to end with some version of, “We need to think about it.”

They opened the meeting with what they thought was the problem: “We need help with pricing.”

That’s usually the tell.

So instead of asking what they charged, I asked a different question: “How do your customers decide if you’re worth it?”

They talked about features and competitors. They talked about being “fair,” and about not wanting to scare people away. All reasonable instincts, but all completely backwards.

Here’s the lesson I’ve learned as both a CEO and a professor: pricing is not about what you charge… it’s about how customers understand value. When pricing feels hard, it’s almost always because the value story isn’t clear enough.

We walked through the conversations they had in their last five deals. Where did customers lean in? Where did they hesitate? What problem were they actually trying to solve? It became clear very quickly that the product was doing something far more valuable than the CEO realized. It wasn’t saving time. It was reducing risk. It wasn’t adding convenience. It was preventing costly mistakes.

But none of that showed up in how they talked about price.

Instead, they anchored pricing to inputs, focusing on hours, features, and comparisons. Customers, meanwhile, were making decisions based on outcomes like peace of mind, avoided pain, confidence. Those two frames never meet.

We reframed the conversation around a simple idea: customers don’t buy your product; they buy the moment after your product works.

Once we named that moment, everything changed.

Pricing stopped being a number and became a signal. It was a signal of seriousness, a signal of confidence, and a signal of understanding the customer’s world. We repositioned the offer around the cost of not solving the problem, and, suddenly, the price wasn’t high. It was actually small relative to the downside customers were already living with.

At first, the CEO was uncomfortable. Not that I was surprised, because most founders are. Underpricing feels humble, whereas raising prices feels risky. But when you price too low, customers trust you less, not more. They assume you don’t fully understand the value you create, or worse, that you don’t believe it yourself.

This is proved itself out when, a few weeks later, deals were closing faster. And it wasn’t because they changed their product. It was because they changed their story. Customers could now see themselves in the value, not the feature list. And the CEO stopped apologizing for the price.

The lesson I left them with (and I’m hoping you’ll take away, too), is that pricing is strategy, pricing is positioning, and pricing is leadership. It tells customers how to evaluate you.

If pricing feels hard, don’t start with the number. Start with the value. And remember, if you can’t articulate the value clearly, the market will do it for you, and it’ll usually do it at a discount.

-Shep

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-Jamie Jones

I was at a talk last week at Raleigh Durham Startup Week and had my memory refreshed about an actionable word-of-mouth marketing framework that I hadn’t thought about in a few years — STEPPS (Social Currency, Triggers, Emotion, Public, Practical Value, and Stories).

The speaker, Jonah Berger, asked a simple question: why do some things spread and others don’t? He wasn’t focused on social media algorithms, but rather on actual people telling other people. Cheaper AND more powerful.

If you’re trying to get a message out — about a product, a cause, an idea — answering this question is imperative. In Contagious, Berger answers this question, which is rooted in world-class research. I highly encourage you to read the book (he’s a great storyteller, which is no surprise), but you can also take the shortcut and learn about the STEPPS framework on his resources page.

Contagious by Jonah Berger.

Tools We’re Tinkering With

-Ryan Bolick

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.

Codex is becoming an operating layer for my startup. Codex is OpenAI’s AI coding agent. Most people use it for the obvious software work: writing code, reviewing pull requests, debugging, and helping ship product faster. I use it for that too, but the more interesting shift has been using Codex to connect what is happening in the codebase to the broader work of building a company.

Each week, I have agents review our code and summarize what changed: what shipped, what slowed down, what questions are still open, and where the roadmap is moving. Because Codex can also connect to other tools and sources, that work does not have to stay trapped in one place. It can pull together and update product docs, customer feedback, sales notes, and planning materials without forcing everyone into the same workflow. Better decisions come from better context, and Codex helps turn scattered activity into actual forward motion.

-Jamie Jones

A few weeks ago I hosted a coffee chat between a handful of student founders and Lindsey Argalas ‘96, CEO of TaxBit and a Duke I&E Advisory Board member. The students came loaded with questions about FinTech, AI, and the future of software. What they were really asking, underneath all of it, was the question that seems to hang over every campus conversation with students these days: will there be jobs, and will I get one?

I try to remain empathic as my students express genuine concern about their futures all while in the back of my mind I am thinking that this angst is unjustified. After all, these are Duke students. They’re statistically exceptional. The creativity, the mental agility, the relentless problem-solving is always on full display, and their smarts live up to the hype. And yet here they were, visibly nervous, asking a highly accomplished CEO to please just tell them everything is going to be okay.

While Lindsey didn’t exactly do that, she did give them an incredible nugget of wisdom.

Someone asked her how software companies build durable competitive advantage in a world where AI lets any firm build its own solution. It’s a real problem for the industry, as the moat that used to come from being the only team that could build something sophisticated is shrinking fast. Her answer was simple and stuck with me: lean into your unique competitive advantage. Figure out why your customers are actually choosing you, because that reason is probably no longer just the technical thing you deliver. What are they really buying? What’s the thing only you can give them?

While the students were thinking about software companies, I was thinking about the students sitting in front of me.

The exact same question applies to every person trying to navigate an uncertain labor market right now. The technical skill, the credential, the major — those things matter, but they’re increasingly table stakes. They’re not the moat. The durable advantage is the thing underneath: what makes you uniquely you, and how does that let you create value for other people in a way that’s hard to replicate?

For one person, it’s an unusual combination of quantitative rigor and storytelling instinct. For another, it’s deep domain obsession paired with an ability to build trust in a room. For someone else, it’s relentless curiosity that keeps them two steps ahead of whatever the next thing is. These are hard things to build. They don’t depreciate the same way technical skills do.

So here’s the question... do you know why someone chooses you for the job, the project, the team? What are they actually buying? If you can answer that clearly, you are going to be just fine.

-Jamie

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Worth Your Time

-Aaron Dinin

I was talking with a friend recently about how busy I’ve been feeling. It’s the kind of busy where every hour is accounted for, every minute feels like it needs to be optimized, and yet somehow it still feels like there’s not enough time. In response, he recommended a book I’d never heard of called How to Live on 24 Hours a Day and written by Arnold Bennett.

I’ll admit, I was skeptical. The title alone sounds like something ripped straight from the modern productivity-industrial complex. But then I started reading it and realized… this thing was written in 1908.

Somehow, it feels like it was written yesterday.

Bennett’s central idea is simple but quietly unsettling. He basically notes that everyone gets the same 24 hours, and most of us waste far more of them than we’d ever care to admit by letting time happen to us instead of deciding, deliberately, how we want to use it.

To be clear, he’s not arguing that we all need to start cramming more into our days. Instead, the point he’s making is around recognizing that time is our most fixed resource, and we should should be treating it with the same intentionality we bring to money or strategy.

The reason I’m sharing this text here is because that mindset is deeply entrepreneurial. Entrepreneurs love to talk about capital, talent, and opportunity, but the real constraint is always time. And not just how much of it you have, but how consciously you choose to spend it.

Bennet’s book is a short read, and, admittedly, a little dated in places. But it’s also surprisingly sharp. And if you’ve ever caught yourself saying “I just don’t have time,” it’s worth sitting with Bennett’s response to that idea… because he’s not particularly sympathetic.

Tools We’re Tinkering With

-Aaron Dinin

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.

In class the other day, I had my phone connected to the projector and was showing something inside an app. But instead of asking questions about the thing I was trying to teach (which, admittedly, was frustrating), my students started asking lots of questions about the app I was using. So I guess maybe a younger generation simply doesn’t know about it?

Either way… I figured I’d share in case you don’t know about it either. The app was Trello, the hyper-flexible, digital kanban board that allows you to basically create and organize lists in whatever ways make sense inside your head.

Kanban, for those who’ve never used it, is basically a system of cards. You place those cards in columns based on whatever organizing principle you’d like to use, you can place whatever you want on the cards, and you can move them into whatever columns you want, whenever you want to.

Also, if that description makes kanban sound confusing, just imagine columns of sticky notes on a whiteboard where you’ve written whatever you want.

Easy, right?

Now, imagine being able to have those sticky notes, except on your computer or phone and they’re infinitely flexible. That’s basically Trello.

Honestly, it used to help me organize basically my entire life… my company, my classes, my family… everything. But then it got acquired, and a lot of the collaboration components that made it so good for working with others were severely limited on the free tier, so I backed off. But, for personal use, the free tier is still my go-to organizer and worth checking out if you’ve never tried it.

-Aaron Dinin

If you spend as much time teaching entrepreneurship as I have, you eventually run into a strange scenario where someone asks you to speak about leadership… because you’re an entrepreneur.

That happened to me again this past week. A student came by my office to invite me to speak at her organization’s leadership conference. When I asked why she thought I’d be a good fit, she responded: “Well, you’re an entrepreneur and you teach entrepreneurship, so you must know a lot about leadership.”

On the surface, I suppose it’s a reasonable assumption. For starters, both words end in “-ship.”

However, despite some superficial overlaps, “entrepreneurship” and “leadership” are not synonyms.

Entrepreneurship is about starting things — spotting opportunities, taking risks, building something from nothing. It rewards speed, independence, and a willingness to act before you have all the information. Leadership, in contrast, is about aligning people, supporting them, managing them, and, often, stepping back so they can do their best work.

Those are very different skill sets.

In fact, the more time I spend around entrepreneurs — and the more entrepreneurial work I do myself — the more I find myself believing that leadership is one of the hardest transitions founders face. Entrepreneurs love doing and building and solving and creating. In contrast, we don’t naturally gravitate toward organizing teams, managing performance, or navigating the messy interpersonal dynamics that come with growth.

But that’s exactly the kind of work you have to do when you’re scaling a company. At that point, the thing that made you successful early on — your ability to do everything yourself — becomes the bottleneck as the job shifts from doing the work to building the system that gets the work done.

That shift is where leadership begins. And, to be clear, it’s a transition lots of entrepreneurs struggle with. It’s also why so many founders either step aside or get replaced as their companies grow. Sure, they might have been great builders, but the role changed into something fundamentally different when they had to become leaders.

None of this is to say entrepreneurs can’t be great leaders. Many are. But it’s definitely not automatic. It’s a completely separate skill that has to be learned, practiced, and, in many cases, actively chosen.

That distinction matters more than we tend to acknowledge because, when we blur the line between entrepreneurship and leadership, we create unrealistic expectations for founders. We assume that because someone can start something, they should also be able to scale it, manage it, and lead a growing team. And when that doesn’t happen — when a founder struggles with hiring, delegation, or team dynamics — we frame it as a personal failure instead of recognizing it as a predictable obstacle when transitioning into a fundamentally different role.

It also matters for entrepreneurs themselves. If you believe entrepreneurship and leadership are the same thing, you’re less likely to recognize when your job has changed. You’ll keep trying to solve problems the way you always have — by doing more yourself — even when the real work requires you to step back, empower others, and build systems that don’t depend on you.

I realize understanding this gap doesn’t make the transition easy. But I wanted to share this little story just to make the issue more visible. Too many entrepreneurs assume a core part of their job is to scale their companies to billions of dollars and thousands of employees. While that goal isn’t inherently wrong, it also doesn’t have to be your goal, particularly if you enjoy building more than you enjoy managing.

Remember, there’s no shame in being a builder, and being a builder doesn’t mean you have to be a leader. Both are important roles, and some people can succeed being both, but confusing the two is where things tend to break.

-Aaron

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Worth Your Time

-Aaron Dinin

This week I’m recommending the same book I suggested to a student who asked me to share my favorite book about entrepreneurship. To be fair, I’m not sure this is my *favorite*, but it’s definitely somewhere near the top.

The book is Kathryn Schulz’s Being Wrong. And the fundamental idea behind it is that we spend most of our lives believing we know things, when in reality, much of what we “know” is actually belief.

For entrepreneurs, this is a superpower if you can learn to leverage it. Specifically, building anything new requires constantly separating what you know from what you merely believe, particularly as it relates to your customer, your market, your product, and your strategy. And the founders who succeed are the ones who are most willing to question their own assumptions and update their beliefs when reality disagrees.

Also, as a bonus, Schulz is amazing to read. She writes in these long, flowing sentences that somehow feel like entire paragraphs — layered, thoughtful, and surprisingly conversational. It’s the kind of prose that makes you see just how poorly ChatGPT writes with all its short, choppy sentences and recycled structures. You won’t find any of that in Schulz, which, alone, is worth the extra time to dig through her words.

Tools We’re Tinkering With

-Amy Wyron Robinson

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.

One of the biggest upgrades to my weekly routine has been using AI tools to help me make slides. I have a lot to say (apparently…), but I’m no graphic designer, so being able to turn my ideas into compelling visuals has saved me (1) a ton of time, literally a day a week and (2) so much angst trying to get things pixel perfect.

My current go-to tool for content-heavy presentations is Gamma, a software one of my colleagues highlighted in a previous issue. BUT Gamma can sometimes feel a bit too… Gamma-y? And the images tend to have that AI-generated je ne sais quoi…

So when I want my slides to sing, I have been turning to Beautiful.ai. It’s giving keynote, TedX, main stage energy. All of my slides for my Narrative Design course were created with Beautiful.ai, as were the slides I used for a recent TedTalk-esque event at Duke, where everything needed to look *chef’s kiss*. If Gamma is the blue jeans of slide creation, then Beautiful.ai is the tailored suit. Don’t make me choose just one!

-Aaron Dinin

This week is Duke’s annual Startup Showcase — our end-of-year event where student founders from across campus pitch their companies, demo what they’ve been building, and (this year) compete for over $110,000 in funding. Obviously, it’s the highlight of Duke I&E’s academic calendar for all of us around here; however, I recognize a lot of you reading this don’t have any reason to care.

But that’s OK. Give me a few paragraphs, because even if you’re not affiliated with Duke, I want to explain how this event is a great reminder of one of the most important lessons in entrepreneurship.

For a bit of context, I joined Duke’s Innovation & Entrepreneurship program a little over a decade ago. At the time, the organization was just getting started, it had recently been funded by a large gift, and the entire community was filled with all sorts of excitement and expectations about what we’d be building. People assumed we’d launch, build momentum quickly, and, within a few years, have Duke positioned as one of the top academic entrepreneurship programs in the country.

That’s not what happened. And, quite honestly, lots of people seemed disappointed. The program that had been so exciting (and spent so much money) looked like a failure because the beautifully branded co-working space wasn’t overflowing with a bunch of employees from billion dollar startups jockeying for more time on the office foosball table.

From my perspective, though, it looked exactly right.

Because I’d seen this pattern before. It’s the same pattern every successful startup follows. Early on, there’s energy and belief — maybe even some early resources — but very little to show for it. Then comes a long stretch of building, testing, and learning that feels slower than anyone wants.

A lot slower. And it usually involves lots of handwringing… particularly from people who don’t know better. Their unrealistic expectations were never going to be appeased because they simply don’t understand that startup growth is exponential, not linear. The beginning always looks slow… that’s where the foundation is getting built.

However, if you’re building the right thing, and you have the right team, and the right leadership, the results start to peak through. They show up, at first, as small signs of progress. But thanks to that exponential growth pattern, they quickly turn into big successes. And suddenly — after a decade of hard work — you’ve got something that looks “overnight” that everyone thinks was magic.

That’s what this year’s Startup Showcase represents, and it’s why I’m incredibly excited and incredibly proud.

This years batch of companies are, hands down, the strongest group of student-led startups we’ve ever featured. In addition, our classes are oversubscribed, our programs are full, and the level of ambition and execution coming out of the community right now is so far above and beyond where we began that it’s hard to remember a time when the organization wasn’t so successful.

But none of this is happening because we did something magical this year. The results of today are because of what we’ve been building toward for ten years.

That’s how startup growth works!

To be clear, I’m not sharing this just to brag (though I’m admittedly a little proud of what’s happening here). I’m sharing this story because I know many of you are in the early stages of building something yourself — a few months in, maybe a year — and wondering why it doesn’t feel like it’s working yet.

Of course it doesn’t…. you’re still laying the foundation!

If you believe in what you’re building, if you’re seeing early signs you’re on the right track, and if you’re surrounded by the right people, the most important thing you can do is keep going. The payoff of good work doesn’t show up immediately. It shows up after enough time has passed for that work to compound.

Remember, in entrepreneurship, success takes time. Always.

-Aaron

P.S. And if you happen to be in Durham on Thursday, April 9th, from 4:00–7:00, you’re welcome to come see what a decade of compounding success looks like in real time.

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-Shep Moyle

I’ve been thinking a lot about how AI is changing what makes a startup actually succeed. When technical skills are no longer the moat, and anyone can vibe code an app, what’s left to differentiate on?

YCombinator shared nuggets of gold on how they see the future of startups, including one worth sharing here: Garry Tan, CEO of YCombinator, argues that when intelligence is available on tap, the two most important human qualities become agency (the ability to actually do things and take initiative) and taste (the ability to evaluate what’s good). Great news for non-technical founders with deep domain expertise and an eye for user experience!

Tools We’re Tinkering With

-Shep Moyle

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.

Clay is an AI-powered sales intelligence and workflow platform that lets startups design their own revenue engine without a heavy CRM, complex RevOps stack, or large sales team. It pulls together data from LinkedIn, company websites, job postings, intent signals, CRM records, and dozens of enrichment sources, then lets founders build logic on top of that data: who to contact, when, why, and with what message.

What makes Clay exceptional for entrepreneurs is how well it supports learning-driven sales. Founders use it to test ICPs by filtering accounts based on real buying signals (hiring, tech stack changes, growth indicators), personalize outbound with context that actually matters, and quickly see what segments convert into meetings and revenue.

Scaling teams use Clay to identify expansion opportunities, prioritize accounts before hiring sales reps, power founder-led outbound, and replace brittle spreadsheets with a flexible, evolving system. The advantage isn’t automation — it’s signal over noise. Clay helps companies stop spraying outreach and start building a repeatable, insight-driven funnel that grows smarter with every interaction.

This week I had the chance to coach ten student founders preparing for a startup pitch competition. Call me crazy but I love the nervous energy of a pitch competition — ideas bouncing around, founders rehearsing under their breath, wondering how their story “lands”, trying to get the story out of their heads and into the hearts of others.

Out of the ten, nine signed up. (Good luck to the one who didn’t — I truly hope they nail it!) But for the nine who were brave enough to walk through the open door, something interesting happened. As we worked through their very different pitches one by one, three themes started to surface.

The first was authenticity. Not the empty buzzword kind. The “tell the story only you can tell” kind. Why this? Why now? And most importantly for an early-stage founder, why you? Judges aren’t only evaluating your idea — they’re evaluating whether you are the person closest to the pain point, the person who has earned the right to solve this problem through your lived experience, the person with the obsession to keep this going long after the shiny pitch competition is over.

Again and again I see founders bury their own stories. A healthcare founder didn’t mention the years spent navigating the very problem they solve. A product designer left out the true aha! moments from their customer discovery that gave them conviction to move forward with this idea. When those details finally surface, the story starts to click. The pitch shifts from a list of features (truly, who cares? no one....) to a personal mission. We see you care. So we mirror that and start to care as well. Our brains light up. Authenticity becomes the foundation of the trust you’re building with the audience.

The second theme was empathy. Not sympathy (although I have sat through plenty of pitches in my life that deserved a handwritten apology after). Empathy means getting out of your head, and putting yourself in the judges’ seats for five minutes. They will be listening to pitch after pitch, brains overloaded. Your job is to make it easy for their heads to start nodding, for their eyes to light up. That means avoiding jargon, insider language, acronyms, and anything that creates distance.

One founder had a slide with abbreviations only a specialist would understand. They aren’t being unclear — they’re suffering from the curse of knowledge. It’s impossible for our brains to remember what it was like before we knew the thing we now know. When we marinate in the juice of our own startup ideas all day long, we forget how to rewind the tape. But speak simply, and suddenly the pitch becomes accessible, relatable, memorable. Simplicity is respect. Clarity is a gift (as is feedback, but that’s a story for another day...)

And finally: precision. The difference between those who practiced and those who memorized or improvised could not be more obvious. The founders who treat their pitch like a craft — who put in the reps, test and tweak, scratch what’s not working, iterate — those founders have a fluidity and ease that you simply cannot fake.

Design thinking isn’t just for product development; it’s for storytelling. Try, fail, try again. Practice your story so much that the words don’t sound rehearsed. Confidence doesn’t come from perfection; it comes from familiarity. Founders who practice become nimble, and that nimbleness makes them believable (see: authenticity).

Founders who embrace authenticity, empathy, and precision craft better stories. Stories that are rooted in who they are, designed for an audience whose humanity they respect, and delivered with the kind of clarity and confidence that only comes from putting in those reps.

-Amy

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Worth Your Time

-Shep Moyle

At first glance, 1929 might look like a history book. But for entrepreneurs, it’s more like a case study in human behavior under extreme optimism and sudden uncertainty.

Sorkin’s account of the 1929 crash goes well beyond markets. It’s confidence, leverage, storytelling, and decision-making when momentum replaces discipline. Those dynamics feel uncomfortably familiar today. Sure, the technologies are different. So is the speed. But the psychology of building, betting, and believing is the same.

Here’s why this book matters for founders now:

Leverage hides fragility.
In 1929, leverage amplified gains until it exposed structural weakness overnight. For modern entrepreneurs, leverage shows up as aggressive burn rates, dependence on future funding rounds, overhiring, and assumptions that capital will always be available. The book is a reminder to ask a simple but powerful question: What breaks if conditions change?

Narratives can outrun fundamentals.
Sorkin shows how optimism and storytelling drove behavior long before the data justified it. Entrepreneurs today operate in similar narrative-driven cycles around technology, growth, and scale. The founders who endure learn to build businesses that work even when the story cools.

Cash creates optionality.
One of the clearest lessons of 1929 is that survival often came down to liquidity. For startups, revenue, cash discipline, and operational flexibility matter more than valuation when sentiment shifts.

Resilience matters more than prediction.
Few saw the crash coming with precision. Many ignored warning signs. The entrepreneurs who last aren’t the ones who time cycles perfectly; they’re the ones who design companies that can withstand volatility. It’s a good reminder that the real entrepreneurial superpower is humility.

In an era defined by AI acceleration, compressed decision-making, and rapid change, 1929 reminds entrepreneurs that while the tools evolve, the risks rhyme. Because of that, understanding history is what makes you prepared.

And in entrepreneurship, preparation is a competitive advantage.

Tools We’re Tinkering With

-Jamie Jones

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.

Do you read constantly but retain little? Do you have a million browser tabs open that you swear you’ll revisit? Do you have Kindle highlights that you’ll never see again?

Readwise fixes this. It syncs highlights from books, articles, PDFs, and websites into one place, then sends you a short daily review — just a handful of excerpts each morning. Five ideas to revisit in only minutes a day… until they stick. We learn through re-exposure, and the best ideas come from connecting concepts across domains. Readwise enables that for you in a daily practice. You tag highlights, add your own notes, and over time start to actually use what you read, in conversations, in your work, in how you think.

I hate subscriptions. Readwise is one of the few tools I pay for because it easily becomes a habit that helps me knock the cobwebs off my brain.

-Shep Moyle

A student came into office hours recently with a decision they described as “a good problem to have.” They had two options in front of them.

One was a good role and good salary with a well-known, brand-name company. It was the kind of job that shows up nicely on LinkedIn and makes Thanksgiving conversations easy.

The other option was their startup. It had early traction, a few customers, lots of uncertainty, and no clear map for what comes next.

They asked the question almost apologetically: “How do I know if I’m making a reckless choice by not taking the safe job?”

I didn’t answer right away. Instead, I asked them to define what “safe” meant.

They talked about income stability. Health insurance. Predictability. Resume value. All reasonable things. All real considerations. But none of them actually addressed the deeper fear behind the question.

So I asked something else: “What happens if you take the job and always wonder what might have happened if you didn’t?”

That question landed differently. Because here’s the truth I’ve learned after decades as a CEO, board member, and teacher: there is no such thing as a risk-free path. There are only different kinds of risk, paid at different times.

The corporate job feels safe because the risk is deferred. You get certainty now, but you may pay later — in regret, in stalled learning, in realizing you optimized for comfort over growth. Entrepreneurship feels risky because the uncertainty is immediate. You pay upfront—with stress, ambiguity, and responsibility.

Neither path is right or wrong. The mistake is pretending one is objectively “safe” and the other is objectively “risky.”

To help the student, we reframed the decision around three questions.

First: What kind of learning curve do you want right now?

Early entrepreneurship compresses learning. You make decisions that matter. You feel consequences quickly. A corporate role can be an incredible learning environment—but only if it puts you close to real problems and real ownership.

Second: What downside are you actually afraid of?
Is it financial instability — or judgment? Is it failing — or explaining failure to others? Naming the real fear often changes the decision.

Third: Is this a forever decision — or a chapter?
Most students dramatically overestimate the permanence of this choice. Careers are long. Startups are not one-way doors. You can try entrepreneurship, learn intensely, and still enter the corporate world later — often stronger for having tried.

With all those things in mind, I told them something I wish someone had told me earlier in my career:

The safest thing you can do early in your career is build optionality.

Skills. Judgment. Confidence. Pattern recognition. The ability to recover.

Entrepreneurship — done thoughtfully — builds all of those. So can the right corporate role. The key is not the label. It’s the trajectory.

They didn’t leave with a definitive answer. And that was the point.

The goal isn’t to eliminate risk. It’s to choose the risk that helps you become the person you want to be.

That’s the real decision.

-Shep

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Worth Your Time

-Jamie Jones

I just finished Careless People by Sarah Wynn-Williams, and I can’t stop thinking about it. Wynn-Williams spent years as Facebook’s director of global public policy, and her account of watching leadership choose growth over responsibility is hard to shake, particularly as I watch what feels like a re-run as we roll out AI.

A few caveats worth naming: this is a memoir. One person’s account, filtered through real grievances and a messy departure. Meta disputes much of it. Read it with that in mind.

Still, the pattern she describes feels all too familiar — brilliant people convinced their platform is a force for good, scaling faster than they can understand the consequences with broad society-shaping impacts lurking.

Social media changed how billions of people communicate, consume information, and make sense of the world before anyone fully understood the implications. AI is more powerful by orders of magnitude, moving faster, and full of people genuinely excited about what it could do for humanity (and like social media, there’s so much upside to be harnessed!!!)

Read the book, then let’s discuss: Where do you see the parallels between the rise of social media and AI? Where do you think AI is actually different? Drop it in the comments.

Tools We’re Tinkering With

-Aaron Dinin

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.

Whenever startups reach a certain level of scale, they suddenly realize “keeping all our contacts inside a Google doc just isn’t working for us anymore.”

Welcome to the world of CRMs! You’re finally starting to understand why Salesforce is a HUGE business.

In fact, your first stop is going to be salesforce.com. After all, isn’t that the CRM? Surely it does exactly what you want.

Except… no… Salesforce is not meant for small startups. I realize it technically has small business pricing that looks attractive, but, whatever you do, stay far away from Salesforce. It’s a confusing mess of a piece of software that, admittedly, is super-flexible, but only because you’ll have to hire a full time Salesforce admin for $100k/year just to organize it and make it capable of doing what you need.

After realizing Salesforce isn’t for you, you’re going to start Googling. You’ll come across Zoho, which is the poor man’s Salesforce. You’ll come across Hubspot’s CRM, which is just trying to get you to enter contacts into its system so you’ll start paying for its marketing platform. You might even begin imagining ways to use tools like AirTable or Trello as your CRM.

But don’t do any of that stuff. Just use PipeDrive. It’s clean, it’s intuitive, it’s powerful, and it’s affordable.

True, it probably won’t be your forever CRM. In fact, you should hope it won’t be. That’ll mean you’ve gotten successful enough to outgrow it, which is a great thing. But, until then, just use PipeDrive.

You’re welcome.

-Jamie Jones

A few weeks ago, Duke’s Startup Showcase held its semifinal round. For the student founders involved, it’s already a big deal since it means you’ve made it past the first cut, you’re presenting in front of real judges, and the feedback you get in that room can genuinely shape how you think about your company.

But one team decided the formal session wasn’t enough.

After they finished their evaluation, they learned that one of their alumni judges, the founder of a very well-known company, was staying in Durham for the night. So they did something most people in that situation would never do. They asked him to grab a drink after dinner.

He said yes.

What followed was more than an hour of real conversation. Not the polished, time-boxed kind you get in a judging session, but the informal, candid kind where successful people actually tell you what they think. Ideas were shared. Doors opened. All because someone was willing to ask.

Their boldness surprised me. I teach our New Ventures Development course and constantly work with student founders. I’m literally paid to help them. And still, almost none of them ask me for feedback, introductions, or help when they’re stuck. The resource is right there, but the ask never comes despite repeated encouragement to do so.

Most people want to help. Especially accomplished people who remember what it felt like to be early and uncertain. They’re not waiting to be asked, but when someone asks directly and genuinely, the answer is yes far more often than you’d expect.

The problem is we talk ourselves out of asking before we ever open our mouths. We assume we’ll seem naive, or pushy, or like we’re wasting someone’s time. We treat the ask itself as the risk, when the real risk is staying quiet.

Here’s the reframe: if you don’t ask, you already have your answer. It’s no. You’ve just received it silently, without giving the other person a chance to surprise you.

The worst case when you ask is that you end up exactly where you started. That’s not much of a downside.

What those students figured out over drinks is something that takes many founders years to learn. Your network doesn’t grow because people sense you need something. Your ideas don’t improve because the right mentor is thinking about your problem when you’re not around. None of that happens on its own.

You have to ask. Directly. Out loud. Even when it feels awkward.

The boldest thing you can do is also, usually, the simplest.

Ask.

-Jamie

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-Aaron Dinin

I’m going to go a little weird with this week’s recommendation and suggest you read a short story from 1909 called The Machine Stops by E.M. Forster.

Yup… 1909.

I honestly hadn’t thought about it since my grad school days, but the reason it came back onto my radar is because I recently assigned it to one of my classes. And revisiting it now… holy cow…

In the story, Forster basically describes pieces of our modern world, but he did it more than a century before these things existed. Specifically, he describes people living in small, isolated rooms, interacting almost entirely through a global communication network that delivers lectures, music, and conversations through screens. It’s not exactly the internet or Zoom or social media… but it’s close enough to make you wonder if he had some sort of crystal ball.

Obviously, Forster didn’t actually “predict the future” in a crystal-ball sense. However, what he did was notice the direction the world around him was moving — increasing reliance on technology, growing distance between people and the systems they depend on — and then he extend those trends forward within the framework of a story. In other words, he didn’t so much guess the future as he inferred it from following the lines of technology.

And that’s the entrepreneurial lesson.

Great entrepreneurs aren’t fortune tellers. They’re observers. They pay attention to small cultural, technological, and behavioral shifts and then ask a simple but powerful question: If this keeps going, where does it lead? Being able to see even a rough version of that trajectory is a massive advantage when you’re trying to build something new.

So yes, recommending a 115-year-old short story in an entrepreneurship newsletter is a little weird. But if you’re interested in the skill of “seeing around corners,” it’s a surprisingly good place to start.

Tools We’re Tinkering With

-Aaron Dinin

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.

These days, I often get asked the best editing software for social media videos. It’s a tricky question to answer because there are tons of options, all of them have some level of learning curve, and “right for you” is going depend on lots of factors ranging from how “pro” you want to be to how much money you want to spend.

So I’m not going to definitively tell you what you should use, but I’m going to share the three main tools I use depending on the job.

Quick, Basic, and Easy

The simplest tool I’ve found is an online video editing service called Kapwing. At $16/month it’s not free, but it doesn’t break the bank. More importantly, it gives you everything you’ll need from video editing to captioning and even some useful AI tools for cleaning video and audio. If you’re looking to just start editing while being able to keep everything easily saved in the cloud, Kapwing is a solid place to begin.

Mobile Editing

Lots of people like CapCut. I’ve had a better experience with an app called LumaFusion. LumaFusion was one of the first iPad-native video editors, so the experience works really well with touch controls. Plus, rather than a subscription, it’s a one-time purchase of $29 for the app. I don’t know about you, but I miss the days of just buying software once. In this case, if you’re serious about video editing, you could do worse than spend $29 just to have a quick and solid editing app on your phone and iPad for when you need it.

Primary Editing

No matter where you start with your video editing, if you get serious about content creation, you’ll eventually move up to either Final Cut Pro, Premier Pro, or DaVinci Resolve. All of them are powerful pieces of software, meaning, on some level, you can’t go wrong. For me, I wound up focusing on DaVinci Resolve, and it’s been great. There’s definitely a learning curve, but the basics are easy enough. Plus, the price is right… it’s free for the version that does everything you’ll need until you start getting super-serious. And to give you an idea of what that looks like, I’m not even to the paid version yet, and I use the software every day.

-Ryan Bolick

A student founder demoed their product for me in office hours recently. Before we talked about the user, the problem, or the workflow, they led with this: “Our product is powered by ChatGPT.”

That was the problem. Not because ChatGPT is bad or the demo was weak. But because they were leading with the enabling technology instead of the value.

So I asked: “Who is this for?”

The founder paused and started explaining the technology again. How the prompt worked. How the model responded. Why the outputs were strong. But the explanation kept returning to the same place: the model itself.

That’s the trap. Founders are understandably excited by what these systems can do. The technology is moving fast. The demos can feel magical. And in the middle of all that momentum, it becomes very easy to mistake technical capability for product value.

But customers buy outcomes, not AI models.

Nobody wakes up in the morning hoping to use ChatGPT. They wake up hoping to get something done. Finish the report. Respond to the email. Analyze the data. Make the lesson plan. Write the code. Understand the material. The model is not the destination. It is, at best, part of the route.

That distinction matters more than a lot of founders realize.

When you build around the model, you often end up with something that feels like a demo. It can be impressive for five minutes, but it leaves the user with a quiet question: what, exactly, is this helping me do?

The strongest AI products do not win because the model is technically interesting. They win because they fit into a real workflow and remove real friction for a real person. They save time. Reduce effort. Improve quality. Lower anxiety. Increase clarity. The model may be doing the heavy lifting under the hood, but that’s not the thing the customer is buying.

Once I explained all this, the conversation in office hours started to shift. We stopped talking about what the model could do and started talking about where a user was actually stuck, and, as a result, the product got much clearer. The founder moved toward a specific use case for a specific person with a specific problem.

The model didn’t change, but the product direction did.

That’s the lesson I hope more founders internalize right now. AI can absolutely enable a product. It can create leverage, unlock speed, and make new experiences possible. But the real shift happens when a founder stops asking what the model can do and starts asking what a specific user is struggling to get done.

Customers buy outcomes, not AI models.

The founders who understand that will build things people actually want to keep using.

-Ryan

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-Aaron Dinin

Admittedly, the specific subject matter of this podcast might not interest you, particularly if you’re not deep in the creator space. It discusses logistics around building and operating engaged online communities.

So why am I sharing it with all of you?

Well, even if you don’t bother listening, the fundamental premise of the episode is worth paying attention to. That premise goes something like this:

In the age of AI, live experiences are becoming more valuable, so entrepreneurs need to start shifting their resources toward offering more opportunities for live experiences.

I’m pretty sure we can all feel the increasing value of live experiences. Every time we see a video and find ourselves asking, yet again, “Is this real?” we get nudged toward wanting more things in our life to engage with in realtime so we know they’re human.

This push toward IRL is going to impact all aspects of entrepreneurship. For example, will live webinars become significantly more more valuable for lead generation than recorded webinars simply because they’re “real”?

Anyway… I don’t quite know the implications of this prioritization of the “real” just yet, but I know it’s happening, and I know it’s worth paying attention to. And, by sharing this podcast, hopefully I’ve got you thinking about it, too.

Tools We’re Tinkering With

-Amy Wyron

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.

Welp. It’s official. This week I broke up with ChatGPT and moved to Claude. Lots of people I admire in the AI space had been talking about making that shift for any number of reasons, and this week convinced me it’s my time to move on to something new.

But breakups are hard even when it’s the right thing to do. And just like a bad ex, the worst part is losing your shared memories. I was not looking forward to starting from scratch with Claude. Luckily unlike with human exes, I was thrilled when I learned I can transfer memories from Chat to Claude by following a few steps. Onwards and upwards!

-Aaron Dinin

A student stopped by my office hours last week just to chat. About halfway through the conversation, almost as an aside, she mentioned she and her roommate had started a banana bread “drop.”

I raised an eyebrow. “Drop?” I asked. I hate when I’m not cool enough to understand Gen Z lingo.

She explained how during one of the recent East Coast snowstorms, they’d baked a few loaves for fun. Their friends loved it, and someone joked they should sell it. The following week, they decided to try. They took pre-orders from friends, bought ingredients, baked in bulk, and handed out the loaves on Friday afternoon.

It was a hit. They sold out and had lots of people asking for more, so the next week, they did it again.

Here we are, a few weeks later, and they’re taking orders by Tuesday night, baking on Thursdays, and distributing on Fridays. Every week, the volume has been increasing. They’re also experimenting with flavors, refining pricing, and trying to figure out how many loaves they can realistically produce without ruining their grades or their sanity.

To be clear, it’s not on a trajectory toward becoming a billion-dollar company. Instead, I’m sharing this story because it’s an example of entrepreneurship in its purest form. In fact, I guarantee in one month she’s learned more about building a business than most students absorb in years of reading about them.

As I chatted with my student, we began unpacking what she’d experienced, and the patterns became obvious.

For example, she identified real demand. Not hypothetical demand or survey-based demand. She found actual humans asking for an actual product and handing over real money.

She also had to deal with marketing. In week one, friends were enough. By week three, they had to expand beyond their immediate circle in order to keep growing. That forced them to think about messaging, timing, and channels. Should they post in campus group chats? Create an Instagram account? Offer referral discounts? Marketing stopped being a theoretical concept she could half-focus on during case studies and class lectures. It turned into a lever directly tied to whether Friday’s batch would sell.

And, of course, there were issues of cost. Flour, sugar, bananas, butter. Packaging. Electricity. Most importantly, time. Baking at scale is not the same as baking for fun. When you’re producing twenty or thirty loaves in a cramped college kitchen, you start to notice inefficiencies. You also start to ask whether your price reflects not just ingredient cost, but effort and opportunity cost.

Sure, this can all be dismissed as a cute side hustle, but that misses the point. Remember, entrepreneurship isn’t defined by scale. It’s defined by the act of creating value and navigating the messy exchange between supply and demand. Whether you’re selling baked goods to classmates or software to enterprises, the fundamental questions are the same.

Who wants this?

Why do they want it?

How do I reach them?

How much does it cost me to deliver it?

What happens when something goes wrong?

Selling banana bread forced my student to confront those exact questions quickly and without ceremony. And all it takes is selling something. Anything. A service. A product. A digital download. A weekend workshop. Banana bread. Whatever.

The point is, once you’ve navigated real customers, real costs, and real tradeoffs, the theories land differently. You stop asking whether entrepreneurship is “for you” and start asking better questions about how you want to build. Because the truth is, if you’re serious about becoming a great founder, you could do a lot worse than grabbing a mixing bowl.

-Aaron

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-Amy Wyron

I’m always looking for frameworks that resonate with my lived experiences in the “startup trenches.” When I came across Rob Snyder’s PULL framework it was like he had been peeking over my shoulder for the last 20 years.

Rob’s PULL framework distills the seemingly mysterious process of finding product market fit to a very practical set of questions — is this a Project that is Unavoidable where the customer is Looking for solutions and those solutions are Lacking?

Rob serves us all a slice of humble pie with his reminder that “supply is what we build; demand is what a person is trying to achieve in their life”… whether or not our startup exists at all!!

A critical read for any early stage founder trying to get inside their customers’ heads to understand how demand actually works.

Tools We’re Tinkering With

-Shep Moyle

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.

Granola is an AI-powered meeting companion that quietly captures conversations and turns them into clear, structured notes, decisions, and action items without changing how you run meetings. It works in the background on Zoom, Google Meet, or in-person conversations, producing summaries that are actually useful rather than generic transcripts.

I’m sharing this tool because founders live in conversations — customer discovery calls, investor meetings, partner discussions, team check-ins. Granola turns those conversations into institutional memory. Use it to spot recurring customer pain points across interviews, track investor questions you keep getting asked, capture decisions made in fast-moving team meetings, or follow up crisply after sales calls.

In other words, the key value here isn’t the transcript. It’s the pattern recognition over time. Granola helps founders move faster, close loops better, and make smarter decisions without relying on memory or scattered notes.

-Amy Wyron

I had a conversation with a student founder recently that stuck with me — a small operational hiccup that ended up revealing a much bigger lesson.

A customer’s booking had failed on the student’s platform. A glitch. An oops. The kind of thing that happens in early product releases all the time.

But what struck me most was the founder’s reaction to it.

“Oh it won’t happen again, we fixed the bug,” they said.

And that’s the trap.

Early stage founders love dashboards: total bookings, conversion rates, growth curves. One failed booking looks statistically irrelevant. But startups aren’t experienced as aggregated metrics. They’re experienced one moment at a time by one human customer at a time.

For that customer, it wasn’t “one failed booking.” It was a broken experience. Silence where they expected answers. A small breach of their trust.

And while it might sound quiet back there behind the dashboard, unreliability gets loud quickly.

What founders often underestimate is that operational misses rarely stay silent. Customers talk. And they might not complain to you, but I promise that group chats, Slack channels, and Reddit threads are full of people complaining about those misses. A single unreliable experience can travel faster than any marketing message.

And, sure, you cannot can’t what people say about your startup. But you can control whether you gave them a story worth telling about you.

Operational excellence sounds like a late-stage Six Sigma-y concept. It isn’t. In the earliest days, operations is the product. Keeping your promise to deliver value is the whole thing. Without that, what are we doing?

Those quiet misses on your dashboard become your squeakiest wheel detractors.

Now carrying that weight is a lot of pressure. It can make you lose sleep. And I’m absolutely not suggesting that founders live with paranoia or beat themselves up endlessly for mistakes.

Mistakes are inevitable. Especially for bootstrapped founders building fast with limited resources. I’m not advocating for perfection. Full stop.

The goal here, to quote Dr. Becky, is repair.

Once the founder understood the impact, they reached out personally to the affected customer to repair the situation. Not a cookie cutter “oops! we dropped the ball!” template email. Not a defensive explanation. They took ownership and followed up to make it right.

Customers that experience that kind of care don’t churn in a huff. They become invested. Some of my strongest customer relationships in my past startup life came from how I showed up when things weren’t perfect.

When you fix a mistake with care, customers see how you operate under pressure. They see your values in action. They see whether you disappear or lean in. They see if they can count on you.

That moment — the repair — feels really hard at the time, but is often more defining than the failure.

Operational gaps are feedback loops. They show you where the bucket leaks: unclear confirmations, weird edge cases, missing alerts, assumptions about user behavior. Founders who treat every miss as signal build stronger systems faster.

And sometimes, stronger customer relationships too.

Customers whose problems you solve thoughtfully tell your story better than you ever could. Not because everything worked - it won’t! - but because you showed up when it didn’t.

This is the message I want founders to internalize:

You will make mistakes. Your customers will be affected. Your success does not depend on never screwing up; it depends on how you make things right.

Rome wasn’t build in a day and neither is your operational excellence. It’s the accumulation of small fixes, repeated consistently and intentionally.

Your success hinges not only on what you build, but how you respond when it breaks.

-Amy

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-Shep Moyle

Entrepreneurs spend enormous time debating what to build, how to grow, and when to raise money. Far fewer spend time on the question that quietly drives all of those decisions:

Who am I—and what do I actually want?

That’s why I encourage entrepreneurs to read Designing Your Life. To be fair, Designing Your Life doesn’t look like a startup book at first glance, but in my experience, it may be one of the most important ones an entrepreneur can read.

The core idea is simple: clarity about yourself enables better decisions under uncertainty. And startups are nothing but uncertainty.

The insight from Designing Your Life is that there is no single “right” entrepreneurial path. The mistake founders make isn’t choosing the wrong strategy. It’s choosing a strategy that doesn’t fit the life they want to build. That mismatch shows up later as burnout, resentment, poor decision-making, or walking away from something that could have been great.

If you’re building a startup and feeling stuck on a “strategic” decision, it may not be a strategy problem at all. It may be a self-clarity problem. And that’s a solvable problem Designing Your Life could help with.

Tools We’re Tinkering With

-Jamie Jones

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.

I’m going to slightly adjust our definition of a tool in this issue in order to share a resource that’s seriously helped me, particularly during the busiest stretches of the semester when my to-do list can feel completely unmanageable — teaching, advising students, alumni meetings, speaking requests, and hundreds of emails that all feel urgent at once.

A few years ago, I stumbled onto this simple framework that completely changed how I think about prioritization, and I’ve been using it ever since. If you haven’t heard of it, I promise it’s worth the two minutes it takes to understand. It’s called the Eisenhower Matrix. (Here’s a video explanation if you’re more of a visual learner.)

The matix seems simple, but the impact comes when you apply it. I ask two questions before anything makes it onto my real calendar: does this move the needle for Duke I&E, and is this something only I can do? If the answer to both is yes, it gets my best time and attention. If someone else on the team can handle it, I pass it along. If it’s just noise dressed up as urgency, it goes in the trash (it takes courage to say no).

During crunch time in the semester, this practice is the difference between feeling busy and overwhelmed but spinning my wheels and actually making progress on the things that matter.

-Shep Moyle

A few weeks ago, I sat down with a small group of student entrepreneurs during office hours. Smart. Motivated. Well-prepared. They had slides, a crisp narrative, and a clear goal for the meeting.

Within the first five minutes, each of them said some version of the same thing:
“Our top priority right now is raising money.”

So asked a simple follow-up question: “Why?”

Their answers came quickly. We need capital to build. Investors expect us to raise. We want credibility. Everyone else is fundraising. None of the answers were irrational. But none of them were right either.

I asked another question: “What would change if you didn’t raise money for the next six months?”

Silence.

That silence is where the lesson lives.

For most early-stage entrepreneurs — especially today — raising money is often a distraction disguised as progress. It feels productive, it sounds important, and it earns admiration. But it frequently delays the one thing that actually matters early on, which is revenue.

I told them what I’ve seen repeatedly over 30+ years as a CEO and board member. The fastest way to de-risk a venture isn’t with a polished pitch deck. It’s with a customer who pays you.

Revenue does three powerful things immediately. First, it proves someone cares enough about the problem to part with real money. Second, it forces clarity. When customers pay, feedback gets honest very quickly. Third, it gives you leverage over investors, over timelines, and over your own confidence.

With this in mind, I helped the entrepreneur restructure their approach. Instead of “How do we raise money?” we asked: “How quickly can we get to your first dollar?”
Then: Your tenth. Your hundredth. Your thousandth.

Thanks to that shift in focus, the ideas became more concrete. One team realized they could charge for a stripped-down version of their product immediately. Another saw they could offer a paid service before building software. A third realized they could pre-sell to early adopters and learn while delivering manually.

We also talked about how different this moment is for entrepreneurs. AI tools now make it possible to prototype, test, launch, and iterate faster than ever and often without any outside capital. You can build MVPs in days, automate workflows, personalize outreach, and test pricing in real time. The constraint isn’t technology or funding. It’s value — and proving your startup has it. Because if you can’t get customers to pay you $1, you can’t expect investors to give you $1 million.

Conversely, if you can get customers to pay you, you may find you don’t need the money nearly as much as you thought.

To be clear, raising capital isn’t bad. But it’s a tool—not a milestone. Revenue is the milestone. And it’s why the best founders I know don’t ask, “How fast can we raise?”
They ask, “How fast can we learn, and how fast can we get paid while doing it?”

That mindset changes everything.

-Shep

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-Aaron Dinin

Yes, the article I’m sharing with you this week is about the increase of emojis in medical records. I realize it probably seems a little… random. But once you’re done rolling your eyes, I want you to stick with me as I explain.

Remember that language is always evolving, which means what feels informal, unserious, or even inappropriate in one generation becomes standard in the next. And while the study I’ve linked to doesn’t appear to break down age demographics, it’s not hard to imagine that younger physicians — people who grew up communicating with emojis — are the ones normalizing their presence in professional settings. What once felt wild or unprofessional becomes simply… normal.

That’s the entrepreneurial lesson and why I’m sharing this article. As you read it, remind yourself that industries don’t change because everyone collectively agrees to modernize. They change because new people enter them carrying new defaults, which means the “right way” to do things slowly shifts as older norms age out and newer norms take their place.

This type of evolution matters because smart entrepreneurs carefully watch the cultural drift in search of opportunity. And even though you’re probably not going to read that 40 confused face emojis (😕) appeared in medical records and think “Eureka! I’ve got my billion dollar idea!”, if you’re savvy, you’re going to see how “normal” changes, and you’re going to apply that lesson with a big 😁.

Or maybe it’s a 🤑?

Tools We’re Tinkering With

-Ryan Bolick

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.

I built ShipItBot to turn vague startup ideas into clear, buildable briefs. You describe what you want to make, who it’s for, and why it matters, and it structures that into something an AI builder or engineer can actually work from. It’s interesting because it focuses less on generating output and more on clarifying intent, which is often the real bottleneck between thinking and shipping.

Give it a try, and let me know what you think!

-Jamie Jones

I was halfway up a hill on my bike when my friend, riding next to me, said, “I need your advice. I had a situation with a startup founder this week that I don’t feel good about.”

This friend works in the innovation function of a multinational equipment manufacturer and is exactly the kind of person founders want to find on the inside of a big company.

He genuinely roots for startups. He loves scrappy teams with sharp ideas. And because he sits at the intersection of innovation, operations, and corporate venture, he knows how hard it is for an early-stage company to translate excitement into a real partnership.

He plays the role of champion. He’ll take extra meetings. He’ll explain the internal maze. He’ll pull together feedback from multiple business units and package it into something usable. In short: he goes out of his way to help a startup succeed inside a system that was not designed for startups.

In this case, he’d been evaluating a company for a paid pilot. He’d gathered input from the teams that would have to adopt the product. Then he did what most internal champions don’t have time to do: he synthesized the feedback and sat down with the founder to walk through it carefully.

And the founder’s reaction quietly shifted everything.

The founder responded with point-by-point rebuttals. Every concern came back with an explanation. Every suggestion got countered. The tone signaled: “Let me tell you why you’re wrong.”

My friend told me, “I could feel myself shutting down in real time.”

He didn’t get angry. He didn’t argue back. He just stopped wanting to be the person pushing this forward internally. And later, when the corporate venture team asked for an update, he stayed professional, but the founder’s defensiveness was now part of the story.

That’s the part founders miss.

Your reaction to feedback becomes feedback about you.

At the early stage, most people are not betting on your product as it exists today. They’re betting on your ability to learn faster than the world changes around you.

Investors call it “coachability.” Operators call it “easy to work with.” Customers call it responsiveness. Potential hires call it leadership maturity. But they’re all scanning for the same signal. They want to know if, when reality pushes back, you get curious… or if you get defensive.

Defensiveness communicates you think speed is having the answer rather than finding the truth, you treat feedback as a threat rather than a gift, and you’re optimizing for being right instead of building trust.

Curiosity communicates the opposite. It signals you’re here to learn, you’re trying to understand the constraints you’re walking into, and you can take input, synthesize it, and turn it into forward progress.

So instead of responding with answers, the most effective founders respond with questions. And not performative questions. Real questions that signal you’re trying to understand. Questions like:

“Say more about why that matters on your side.”

“What would success look like in your world?”

“What’s the risk you’re trying to reduce?”

“If we could solve one thing first, what would make the biggest difference?”

Curiosity versus defensiveness is the difference between a startup with upside or a startup with too much friction. Because feedback — like the kind my friend was giving — isn’t meant to test startups. It’s meant to help them win.

-Jamie

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-Ryan Bolick

This Product Picnic essay makes a simple but important point that strategy often goes wrong long before execution. It goes wrong at the moment the problem is defined.

The essay argues that when teams frame problems too narrowly, or in terms of a preferred solution, they unintentionally limit the range of strategies available to them. What follows can look like focus and decisiveness, but is often just early misguided conviction.

This is especially relevant right now. Building and shipping are faster and more accessible than ever. Clear problem framing remains slow, ambiguous, and hard to shortcut.

If you’re thinking about product direction, strategy, or what to prioritize next, this is a useful lens.

Tools We’re Tinkering With

-Aaron Dinin

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.

Today, I’m gonna reveal one of my favorite lead prospecting tools from back in the days when I was constantly trying to hunt down contact info for potential sales leads, investors, and even guests for my podcast.

The tool is RocketReach. There’s a full web interface you may or may not find useful, but the part I always loved was the Chrome extension. It basically adds a little button to LinkedIn that lets you get the email of just about any LinkedIn profile you’re looking at.

I realize other platforms can do something similar. And some of them can cost less (last time I checked, Apollo is a good option). But, for me, RocketReach’s data has always been the best. Specifically, RocketReach has always been great about surfacing personal email addresses. And emailing someone’s personal Gmail is usually a much better way of reaching them than their corporate email.

However, I should mention, RocketReach isn’t great for high volume, non-targeted sales prospecting. There are other email tools better for that. You also might not want to email someone’s personal Gmail if you’re trying to sell an enterprise deal into their company. But RocketReach is great for getting the email address of that one potential investor, one potential entrepreneur, or one potential partner you want to send a personalized email to and be sure they’ll see it.

-Ryan Bolick

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

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Worth Your Time

-Aaron Dinin

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

-Amy Wyron Robinson

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.

Inside the Office

-Aaron Dinin

Like most of the East Coast, over here in Durham we spent last week collectively bracing for what meteorologists were generally calling a once-in-a-however-many-years snowstorm. The forecasts were ominous, so, naturally, the grocery stores got cleaned out, schools shut down in advance, events were canceled/rescheduled, and so on. The entire city went into full “better safe than sorry” mode.

And then… the storm mostly missed us by a few miles.

Durham ended up with some freezing rain and a light dusting of snow, while Duke’s campus looked more inconvenienced than crippled. By the time you’re reading this on Tuesday morning, things will mostly be back to normal. No harm. No foul.

In these types of moments, the tempting thing to do is look back and say, “Well, that was an overreaction.” Heck, if I’m being honest, my first instinct in these scenarios is to roll my eyes and complain about the “giant nothing.” But then I have to remind myself of the very real challenge of making decisions inside of uncertainty.

The decision to shut things down wasn’t made because people knew the storm would be devastating. It was made because they didn’t know, and because the consequences of being wrong weren’t evenly distributed.

If the storm had hit as predicted and the region hadn’t prepared, the downside would have been enormous: stranded people, unsafe conditions, real harm. If the storm missed — as it did — the downside was relatively small: inconvenience, rescheduling, and a few days of mild embarrassment.

When you stop to actually think about the scenario, you realize what happened wasn’t poor decision-making. It was good risk management. And good risk management is a tricky skill.

In fact, entrepreneurs struggle with this exact dynamic all the time. We tend to evaluate decisions based on outcomes instead of information. If something works, we call it smart. If it fails, we call it stupid. But that’s the bias of hindsight.

Real entrepreneurship happens before outcomes are known, which means, effective entrepreneurs have to evaluate questions like:

What’s the worst case if I’m wrong?
What’s the cost of acting too early versus too late?
Which mistake is survivable?

In other words, the latest non-storm-of-the century (where I’m writing this from, obviously not for people farther north) is a helpful reminder that sometimes the right move looks like an overreaction only because things turned out okay. And sometimes success isn’t avoiding disruption — it’s choosing the kind of disruption you can live with.

That’s not a weather lesson. That’s an entrepreneurship one.

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Worth Your Time

-Amy Wyron Robinson

I've fully drunk the Kool-Aid on the importance of storytelling. I literally teach the course for Duke's I&E Graduate Certificate (“Narrative Design”). So of course I was thrilled to see this recent article highlighting the importance of storytelling in the WSJ — “Companies Are Desperately Seeking Storytellers.”

AI is making it cheaper and easier to build (yay!) and simultaneously is generating a tremendous amount of slop (less yay!). So at the exact moment there are tons of new innovations, the world is getting far noisier. Getting attention for your great idea / startup / innovation is just going to get harder. Your best chance of being heard is by crafting a story that's yours and yours alone, grabs our attention, holds it long enough to help us become believers, and pays it back in the end with value. Good luck to us all!

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.

Lummi is AI-based stock photography. You probably read that and thought, “Why do I need someone else to use AI to create photos for me when I can just ask my AI platform of choice to create images for free?”

However, if you’ve ever tried using those tools to create your own images, you know creating high quality outputs isn’t as easy as it seems. And it’s a particularly frustrating problem when you’re looking for the perfect image to drop into another piece of content (like, for example, this newsletter, or a pitch deck, or on a landing page), and you find yourself spending more time trying to create the perfect image than you spent creating the content where you’re using it.

That’s where Lummi becomes incredibly helpful. It’s high quality AI stock photos. It gives you a broader range of options than traditional stock photo sites (for example, a dog wearing glasses), but great quality without spending hours tweaking your prompt.

So if you use lots of stock photos (like, say, professors trying to spruce up your lecture slides), but you’re tired of the same old sites, Lummi could be your answer.

Inside the Office

-Amy Wyron Robinson

As part of my role at Duke, I mentor the Melissa & Doug Entrepreneurs, Duke’s premier program for student founders. Many of our students are navigating entrepreneurship for the first time, which means they’re not just building companies; they’re also figuring out who they’re allowed to be in the room.

I saw an example of this during the past week when one of my mentees came to office hours frustrated with early-stage sales. He wasn’t struggling with interest in the idea itself. He was struggling with how to show up.

When he introduced himself as a student working on a project, doors opened easily. Alumni, operators, and potential customers were generous with their time. They took meetings. They offered advice. They shared context. But when the conversation edged toward a possible commercial relationship, he felt awkward (almost dishonest!) like he was pulling a bait-and-switch. The shift from “I’m here to learn” to “I’m here to sell” felt forced and unnatural.

So he tried the opposite approach. He presented himself as a founder from the start. Clear value proposition. Direct ask. Professional posture. And suddenly, the meetings dried up. Without the student framing, he found it harder to leverage his network or get his foot in the door.

He felt stuck between two identities, both of which seemed to work (and fail) in different ways.

Together, we stepped back and reframed what sales actually is.

Sales isn’t about pushing your product across the table to someone else. And it’s not about convincing, cornering, or “closing.” At its core, sales is about sitting on the same side of the table as the other person, looking together at their problems, priorities, and constraints, and asking a simple question: Is there a way to create value here together?

Once you see sales that way, the identity tension dissolves.

It doesn’t actually matter whether you show up as a student working on an idea or a founder building a company. You’re not “pitch slapping” someone halfway through the conversation. You’re engaging in a genuine exploration: Is this problem real? Is it urgent? Are existing alternatives insufficient? And if so, could what you’re building help? And if all of that turns out to be true, how can we move forward?

That framing turns the conversation from a performance into a collaboration.

No one wants to waste their time. Not founders, and not the humans they’re talking to. But an open, honest conversation aimed at discovering whether real value exists is rarely a waste. As Rob Snyder, who teaches entrepreneurship at Harvard, describes it, the goal is to uncover PULL: a project that feels unavoidable and urgent, where the person on the other side is actively looking for solutions and dissatisfied with the lacking options available today.

If you can identify that PULL together, the path forward becomes obvious. If you can’t, you’ve still learned something essential, and you’ve done so without pretending to be someone you’re not.

For early-stage founders, especially students, the lesson is simple but hard-earned: sales isn’t about choosing the “right” label. It’s about choosing the right mindset. Sit on the same side of the table. Get curious. And let value, not identity, drive the conversation.

-Amy

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Worth Your Time

-Shep Moyle

Secrets You Can Learn From Your Customers is a conversation between Michael Seibel and Dalton Caldwell (of YCombinator) that explores one of the most underappreciated advantages early-stage founders have: direct, genuine relationships with their customers. The core idea is that the fastest way to learn what to build (and why) is to actually care about the people you’re trying to serve, and then spend real time with them. Yes, it seems simple, but it’s harder than it sounds.

Through stories from Airbnb, Brex, and Twitch, the video shows how breakthroughs rarely come from surveys, dashboards, or clever plans, but from founders who sit down, ask questions, and listen long enough to uncover insights others miss. If you’ve ever felt stuck, overconfident, or unsure what to do next, this is a powerful reminder that your customers are often sitting on a gold mine of information… if you’re willing to slow down and pay attention.

Tools We’re Tinkering With

-Jamie Jones

I’m the kind of person who will absolutely fixate on making slides look beautiful—because design does matter, and messy slides can distract from a great idea.

Unfortunately, as a founder, you can’t afford to burn hours perfecting formatting when the real leverage is in nailing your message. For me, Gamma has been a simple way to get both. Basically, you drop in your bullet-point outline, and it turns it into a polished deck. Best of all, you can export it straight into PowerPoint, which means you still own the content — your titles, your narrative, your positioning. Gamma just removes the design busywork so you can spend your time on what actually matters… clarity, credibility, and momentum.

Inside the Office

Last week, we hosted something called Startup Fest. It’s our annual Spring semester networking event where hundreds of students across Duke’s entrepreneurial ecosystem show up with ideas, half-ideas, résumés, curiosity, and a healthy dose of social anxiety. It’s loud. It’s awkward. It’s energizing. And it’s one of my favorite reminders of how entrepreneurship actually begins. Despite everyone’s obsessions with products and pitch decks, entrepreneurship starts with people trying to find each other. And that’s exactly what Startup Fest is for.

Toward the end of the event, I bumped into a student who’s in the early stages of launching a startup. He was sharp, thoughtful, and clearly frustrated. He’d been struggling to find a cofounder and was starting to convince himself it wasn’t necessary.

“Honestly,” he said, “with all these AI tools now… do I even really need a cofounder?”

I didn’t hesitate. “Yes. You absolutely do.”

That answer usually surprises people, especially right now. AI has made doing things by yourself easier than ever. You can design, code, research, write, analyze, and automate at a level that would’ve required a small team not that long ago. In that context, a cofounder might seem obsolete, but none of those things are the main job of a cofounder.

A good cofounder isn’t just someone who helps you execute. A good cofounder is someone who helps you focus by bringing complementary strengths. If you’re great at vision and customer conversations, you need someone who thrives in systems and execution. If you love building, you need someone who loves selling. Not because AI can’t help, but because humans still make judgment calls, prioritize tradeoffs, and decide what actually matters.

But even that’s not the most important reason.

Startups are hard in ways that don’t show up on product roadmaps. They’re lonely. They’re emotionally exhausting. They involve long stretches where nothing seems to work and no one is cheering for you. A cofounder is someone who goes to war with you… someone who can say, “This week sucked, but we’re not quitting,” and actually mean it. AI can optimize workflows. It cannot sit across from you and keep you moving when motivation collapses.

Plus — and this is a harder truth founders don’t always like hearing — finding a cofounder is a test. If you can’t convince one other person to commit years of their life to building this thing with you, how the heck do you expect to convince customers? Investors? Early employees?

To be clear, I don’t mean solo founders can’t succeed. Some do. But the difficulty of finding a cofounder isn’t a bug in the system. It’s a feature that forces you to articulate your vision clearly, listen, and… yes… sometimes even compromise. And it does all that while forcing you to prove — early — that your idea is compelling enough to inspire belief.

So yes, finding a cofounder is hard. But remember, it’s supposed to be. If finding a cofounder were easy, it wouldn’t be one of the most meaningful filters entrepreneurship has to prove you’re building something the world needs.

-Aaron

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Worth Your Time

-Jamie Jones

Founders love the lightning-bolt story: one insight, one pivot, one launch that flips the switch. This Fuqua Insights podcast episode — “Can 1% Improvements Transform Your Business?” — is a calm (slightly ruthless) counterpoint: the startups that win more often build a repeatable way to get a little better — over and over — on purpose. In other words, rather than trying to be brilliant, focus, instead, on getting a little better each day.

In the podcast, Duke Fuqua professor Sharique Hasan looks at how experimentation (often via A/B testing) becomes a pathway to compounding improvement. And it turns out to be especially important when you do it consistently.

By the way, one of the biggest value adds of Duke I&E — and why we're excited to keep expanding this newsletter — is that we’re embedded in a research university, which means the “how entrepreneurship actually works” lessons don’t just come from war stories. They also come from colleagues who study these questions rigorously and at scale, and we get to use spaces like this to translate that kind of evidence into practice.

Tools We’re Tinkering With

-Aaron Dinin

This week’s tool is simple, free, and wildly underused: Vidyard. Specifically, the Vidyard Chrome extension that lets you record a quick video of yourself and drop it straight into an email.

Most entrepreneurs default to walls of text when they need to explain something — a follow-up, a clarification, a pitch, a thank-you. But text strips out tone, context, and humanity. A 60-second video does the opposite. It lets people see your face, hear your voice, and understand intent immediately. In practice, that means fewer misunderstandings, faster alignment, and better relationships.

I used to love using Vidyard back when I was selling because it was a frictionless way to keep my face in front of potential customers. Now I actually use it to email students because they’re much more likely to actually watch video instructions than read anything I write in an email.

And by the way, Vidyard isn’t the only option. We’re not trying to sell you anything here… just being helpful. The important thing is sending videos rather than long emails. And Vidyard just happens to make that really easy. You click record, talk like a human, and paste the link. Simple.

By the way, I realize the irony of telling people they should be sending videos instead of long, text-heavy emails in a text-based newsletter. But even if some audiences prefer emails, most people default to video whether we like it or not, and the founders who win are the ones who communicate faster, clearer, and more humanly.

Inside the Office

Welcome to 2026! And welcome to an upgraded Entrepreneur Office Hours, now powered by the entire team at Duke Innovation & Entrepreneurship.

I’ve been hinting for a while that changes were coming, and this is the moment where those ideas turn into something concrete. The goal of this next version of Entrepreneur Office Hours is to make this resource more useful, more practical, and more grounded in the real work of entrepreneurship.

To do that, issues are going to consist of three core sections, with each one designed to give you something tangible you can think about, learn from, or try.

Inside the Office

Each issue will kickoff with short, real stories from the classroom or the entrepreneurial work we’re do alongside students and founders. This space is meant to highlight the kinds of moments we often see in our work with entrepreneurs — the moments where things don’t necessarily go as planned — and use those moment to surface a lesson worth carrying forward. After all, that’s a big part of what entrepreneurship education is (both the formal and informal kind)… it’s learning from experience.

Worth Your Time

Each week, we’ll share a piece of content we’ve found genuinely interesting or useful, including articles, podcast episodes, videos, or maybe even the occasional academic study (but, we promise, the kinds that have real world value). The goal here is to make sure EOH is connecting you with real knowledge about startups, markets, and the fundamentals of entrepreneurial decision-making under uncertainty, plus some helpful context for why it’s worth your time. (For the record, this is something I’ve been wanting to include for a long time, and I’m excited to finally share more than just my own articles.)

Tools We’re Tinkering With

Since entrepreneurship is as much about tools as ideas, we plan to start highlighting products, platforms, and services we’ve been experimenting with along with a short explanations of what they do, why they’re interesting, and where they might (or might not) fit into your entrepreneurial workflow.

Again, none of this is meant to be hype-y or prescriptive. This evolution is meant to better represent the kind of ongoing conversations at the core of entrepreneurial progress. It’s a set of ideas, resources, and experiments you can borrow from, push against, and, in hopefully valuable ways, adapt to your own work.

This week, I’m covering all the sections. However, starting next week, my colleagues will be chiming in and sharing, too. We’re all looking forward to this next chapter of Entrepreneur Office Hours. As always, thanks for stopping by, and send along any thoughts/questions/ideas to help us keep making this better.

— Aaron & the Duke I&E Team

P.S. As I make this transition, I’m sure I’m going to break some things. For example, I have no idea who’s going to be listed as the “sender” of this issue or how it might impact deliverability. But, as we all know, breaking things is an important part of entrepreneurship. Thanks, in advance, for tolerating the inevitable screwups of trying something new. It’s entrepreneurial progress in-action!

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Worth Your Time

-Aaron Dinin

As you all know, lots of my entrepreneurial attention over the last few years has shifted toward social media. But it’s not because I have a wandering eye and no longer care about entrepreneurship. It’s because social media creators are an incredible subsection of entrepreneurs.

Chief among those creators is Jimmy Donaldson, a.k.a. MrBeast. If you’ve not listened to any interviews with Jimmy, you really should. For my money, he’s one of the most thoughtful entrepreneurs in the world at the moment.

As an example — while I feel a little guilty for recommending this — his Diary of a CEO interview is filled with amazingly savvy insights. For example, this clip about “purple cows” is brilliant… especially if you take it beyond the context of creating videos and think about it more broadly in terms of products, marketing, customer acquisition, fundraising, and just about anything else you need to do to push your entrepreneurial vision forward.

FYI… it’s a little NSFW because of language!

(If you’ve got time for the full, 1.5 hour interview, you can find it here.)

Tools We’re Tinkering With

-Aaron Dinin

If I’m being honest, I’m not the right person to tell you about the coolest, latest, and most innovative tools in the entrepreneurial world. Heck, that’s a big reason I want other people helping me write this newsletter. Simply put, there’s a lot more in the world to tell you about than what I know, and adding additional perspectives is going to enable this resources to be more valuable.

However, since I’m in the driver seat for this issue, I’m going to share a tool I’m sure lots of you have heard of, but I’m not sure enough of you are using it: Airtable.

Or rather, not enough of you are using it to its full capability. Most people I talk with think of Airtable as a nicer spreadsheet or a lightweight database. While that’s technically true, it misses the point. Airtable isn’t about rows and columns — it’s about modeling how work actually happens. It lets you design systems around messy, real-world processes like content pipelines, research tracking, customer discovery notes, course development, partnership outreach, and all the half-structured information that entrepreneurs live inside every day.

At this point, Airtable has quietly become the backbone of my workflow. Nearly everything I do — classes, content, research, newsletters, collaborations, and long-term projects — runs through Airtable in some form. It’s where all my ideas live long before they turn into something polished, and it’s what helps me keep track of all those things as I push them forward.

If you’re not using Airtable… that’s fine. This isn’t an ad for it. Instead, find something equally powerful that can serve as the hub of your entrepreneurial workflow. I wish I’d been better about finding that tool earlier in my journey as an entrepreneur, and, I promise, it’ll help you, too.

One of the underrated perks of writing a weekly newsletter like Entrepreneur Office Hours is that, once a year, you get to write an end-of-year retrospective. It’s the easiest issue of the year! No new ideas required. No fresh anecdotes. No clever framing devices. You just look back at everything you wrote, pick a few favorites, link to them, and call it a day. It’s the content equivalent of leftovers — and I mean that in the best possible way.

Or rather… that’s the theory…

In practice, this issue somehow always takes longer than a normal one, and I’m not entirely sure why. I’m guessing it’s because the moment I start looking back, I see more than just links — I see context. I remember what was happening when I wrote each piece. Which ones came from class conversations, which ones came from student emails, which ones were born out of frustration, excitement, curiosity, or exhaustion.

Suddenly, what was supposed to be a quick “greatest hits” becomes an exercise in reflection. And reflection, as it turns out, takes time.

So yes, I didn’t have to come up with a brand-new idea for this issue. But I did end up re-reading lots of what I wrote this year, thinking about what resonated, what didn’t, and how my own thinking about entrepreneurship has continued to evolve. Which feels… appropriate, actually. After all, that’s what this newsletter has always been for me. I realize, functionally, it’s a place to share advice for all of you, but, for me, it’s a running record of ideas tested in classrooms, office hours, conversations, and real entrepreneurial work. Looking back on it all at once is a reminder of how much can happen in a single year, even when you’re just showing up week after week and writing one email at a time.

Below, you’ll find a handful of my favorite articles from the past year. If you missed them the first time around, I hope you enjoy them now. And if you’ve been reading all along, consider this a chance to revisit the ones that stuck with me the most.

Heads up… this will be the final issue of Entrepreneur Office Hours for the year. And that means I need to end with a huge thank you. Thank you for reading, replying, sharing, disagreeing, and sticking around. I genuinely don’t take that lightly.

I hope you have a restful, joyful holiday season and a happy new year. And when we’re back in 2026, we’ll be rolling into it with some big, exciting updates for EOH that I can’t wait to share.

See you on the other side.

— Aaron

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This week’s new articles…

If Your Startup Is Interesting You’re Doing It Wrong

The things that excite you most as a founder are also the most likely things to destroy your company.

I’m Still Surprised Founders Keep Making the Same Mistake

After 10 years teaching entrepreneurship, I can’t believe I’m giving the same advice to every founder I meet.

Top 5 Most Popular Articles of 2025

#5) The Slide You Need to Remove From Your Pitch Deck Immediately

The moment investors see it is the moment they stop listening.

#4) The Most Important Startup Skill Nobody Talks About

It’s an important life skill, too!

#3) Why Most Startups Fail Before They Ever Make a Sale

Inexperienced founders are always making the same mistake.

#2) The Best Entrepreneurs Are Smart Enough to Not Build Startups

What if you could be a great entrepreneur without ever have to deal with the challenge of launching your own company?

#1) The One Lesson About Startups No Business School Can Teach You

You’ll learn a lot in business school about building and running companies, but there’s one thing that’ll never happen.

When I start coaching a new founder, I don’t begin with their product.
I don’t ask about their market size, their roadmap, or their latest fundraising round.

I begin with three questions:

Who are you?
Why do you exist?
What do you really want?

You’d be amazed how many brilliant, driven entrepreneurs can’t answer them.

They can confidently tell me about their total addressable market. They can walk me through their next sprint. They can rattle off investor feedback and hiring plans. But when I ask what they truly want — as a human being, not as a founder — they pause.

And almost always, they say the same thing:

“That’s a really good question.”

And it is a really good question. Because, until you can answer those questions with clarity, you’re just renting someone else’s definition of success.

The Most Undervalued Competitive Advantage

Clarity isn’t a nice-to-have in entrepreneurship. It’s the foundation of everything:

• Your focus

• Your energy

• Your decisions

• Your culture

• Your resilience

Clarity is what separates momentum from motion, and it’s what keeps you moving when the world gets messy (which, by the way, it always does).

I’ve lived this. I spent three decades building and leading a company through every imaginable high and low. And the truth I learned during that process is the greatest danger to a founder isn’t failure. It’s drift.

Drift Is What Happens When You Lose Yourself

When you drift, you forget why you started. You begin chasing the urgent instead of the important. You measure yourself by everyone else’s scoreboard. And somewhere along the way, you lose the thread of who you are.

That’s when founders burn out, teams lose faith, and great ideas die. They don’t die from competition. They die from confusion.

So let’s go back to the Three Questions and how they help solve the problem of drift:

1. Who are you?

I’m not asking for your title. I’m asking about your identity — what you stand for when everything’s on the line.

2. Why do you exist?

I’m not asking for a mission statement. I’m asking what purpose would still matter to you if nobody ever noticed.

3. What do you really want?

I’m not asking about your exit strategy. I’m asking what success looks like when the applause fades.

If you can answer these questions honestly, you unlock something founders rarely talk about: Alignment.

Your decisions start matching your values, your team feels your authenticity, and your company becomes a reflection of who you are, not just what you do.

That’s the moment leadership shifts:

From external → internal.
From hustle → purpose.
From noise → clarity.

Before You Build Anything Else… Build This

Before you build your next product, hire your next team member, or pitch your next investor, stop and answer these three questions:

Who am I?
Why do I exist?
What do I really want?

Until you do, every strategy and metric sits on sand. But once you’ve done it, everything aligns. The right people find you, the right opportunities appear, and the work starts to feel less like grinding and more like living your purpose.

That’s the real lesson, that’s where founders become leaders, and that’s the clarity every entrepreneur deserves before chasing the next great idea.

-Shep

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This week’s new articles…

The Wrong Way to Build a New Startup

Inexperienced founders always make this same mistake, and it’s why so many new companies fail.

The Tragic Way AI Is Destroying 25 Years of Entrepreneurship Progress

In lots of ways AI has been great for startups, but there’s one huge problem founders are completely ignoring.

Office Hours Q&A

QUESTION:

Why do so many people seem to think they need a cofounder?

Every time I talk about wanting to start something, people immediately ask, “Who are you doing it with?” Like doing it solo isn’t even an option. I get startups are hard, but I’m not sure having a cofounder automatically makes things easier. But maybe I’m wrong?

- Jules

This is one of those questions I get asked a lot and I’ve answered it before. But I appreciate how you framed it — not as a demand for a cofounder, but as an honest wondering about whether going it alone is even possible.

Sure, it’s possible. But remember that startups are unbelievably difficult. Even the smallest ones. And not just emotionally difficult. I’m talking practical issues, too. There’s always more to do than one person can reasonably manage. You’re the CEO, the product manager, the marketer, the customer service rep, the salesperson, the janitor — all at once. That’s not just exhausting. It’s unsustainable. Heck… if you’re all by yourself, what happens if you want to go on vacation? Or what happens if you get sick!

Even if you could somehow handle the sheer volume of work, there’s still an even bigger problem, which is blind spots.

No matter how smart or experienced you are, you’ll always have gaps in perspective. You’ll miss things. You’ll overestimate things. You’ll solve the wrong problem. And, without someone else in the trenches with you, it’s very hard to catch those mistakes before they hurt you.

This ability to balance you is what a good cofounder brings. Having a cofounder isn’t just about more labor. It’s also more clarity, and sometimes even friction in the right places. In other words, it’s someone to tell you “no” when you’re too confident or “yes” when you’re losing steam.

To be fair, you don’t technically need any of that. But should you be open to finding one? Absolutely — especially if you’re already feeling the weight of going it alone.

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

A huge thanks to everyone who replied to last week’s newsletter with thoughts about what you’d like to see as I look for ways to expand and enhance Entrepreneur Office Hours. I got far more responses than I expected — thoughtful, kind, curious, and generous. I’m already working through the feedback and thinking about what it will look like to weave some of those ideas into future issues. Stay tuned!

In the meantime, I want to focus on one piece of feedback in particular.

Only one person — one! — sent a response saying he wanted more content on sales and customer acquisition.

Can I be honest with you?

I was disappointed.

And not disappointed in that reader — disappointed in everyone else. It should have been the number one answer. I should have opened my inbox to hundreds of emails saying: “Teach us how to get more customers!”

In other words, if this was a test… you all failed.

Yes… I’m joking (mostly). But it’s also something worth at least mentioning, and this felt like a good moment to remind everyone that sales and customer acquisition are the oxygen of entrepreneurship. They are the unglamorous, unsexy, non-viral work that actually determines whether you have a business or just a very expensive hobby.

Also — because I have access to the data on all this stuff — I see that anytime I write about sales, customer discovery, or acquisition strategies, the engagement is always noticeably lower. Fewer clicks. Fewer shares. Fewer emails. It’s as though everyone collectively says, “Oh yeah… that’s important, but I want the fun stuff.”

And I get it. Fundraising is sexy. Ideation is addictive. Product development is fun. We gravitate toward the glamorous parts of entrepreneurship like storytelling, branding, strategy, vision, leadership, creator psychology, and so on. Sure, those things matter, but let’s be clear: nothing matters if you don’t have customers.

Period. Full stop.

Sales is not the dessert course of entrepreneurship. Sales is the plate everything else sits on.

So maybe this is a moment for all of us — myself included — to do better. As I reshape Entrepreneur Office Hours with the help of my Duke colleagues, I want to make sure the “boring-but-crucial” parts of entrepreneurship get more attention. Yes, I’ll keep including the inspiring stories or philosophical musings, but I need to do a better job of bringing the practical, tactical foundations that determine whether something actually works in the real world. That’s an important change for me to make as a writer. And hopefully you also agree it’s important for you as an entrepreneur.

Onward!

— Aaron

Share Entrepreneur Office Hours

This week’s new articles…

The Real Cheat Code to Building Billion-Dollar Startups

To create the kind of world-changing company every young founder dreams about, you’ll need to find a different type of idea.

When to Walk Away From a Big Business Opportunity

What if it’s possible for an entrepreneurial opportunity be huge and, at the same time, not worth chasing?

Office Hours Q&A

QUESTION:

Hi Dr. Dinin,

I’ve been running a newsletter for about six months. I’ve got around 300 subscribers who are mostly people I know from LinkedIn or past jobs. I enjoy writing it, and the feedback has been good, but I’m not sure how to grow it beyond my personal network.

What are the best ways to get in front of new people when you don’t have a big platform yet?

Thanks for all your advice and content. I actually found you through your newsletter (which I love reading every week), so I figured this was the right place to ask.

—Jason

Bold move to ask my advice about a newsletter in my newsletter. Kind of makes me feel like I’m helping the competition…

But, sure, I’ll give this a shot.

Most people assume the hard part about newsletters is the writing. It’s not. The hard part is getting people to read the writing. And that’s especially the case when you’re not famous, not rich, and not buying ads.

Because of this, the best way to create a successful newsletter is to focus on building distribution habits to go alongside your writing habits. This means:

1. Use your newsletter like a high-quality bribe.
Your best bet for consistent growth is direct referrals. So start asking for them. Not in a spammy, begging way. Just wherever you can: In the newsletter; in your social media bios; in the footer of your emails. Get used to always having a link that tells people, “Hey there… I’ve got a newsletter!” You might feel a little desperate doing this, but, to be fair, you are desperate, so that’s to be expected.

2. Don’t promote your newsletter. Promote your ideas.
Nobody wants to “sign up for your newsletter.” But they do want to read the clever ideas you can’t stop thinking about. So pull out the sharpest line from each issue and turn it into a LinkedIn post. But don’t post the link. Post the insight, then let curiosity drive traffic back to the source.

3. Steal other people’s distribution (ethically).
Find five people whose audiences should be reading your stuff. Mention them in an issue. Quote them. Build something that flatters them and adds value for your readers. Then send it to them afterward. No ask. Just a heads-up. Some will share it. And, honestly, that’s the majority of the game. Rinse and repeat.

Also — and this is the part nobody wants to hear — growth is supposed to feel slow. It’s supposed to feel like nobody’s reading. The people who win are the ones who keep writing even when it feels like nobody’s in the audience.

So keep showing up. Keep publishing. Keep making the kind of thing you’d want to read even if it feels like nobody else is reading. That’s how you grow. From there it just takes time.

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