-Amy Wyron Robinson

Every spring, I watch my students stress about internships.

Applications. Interviews. Rejections. LinkedIn announcements. Comparisons. The pressure is immense. Internships have become a currency of college achievement, and the assumption is simple: the better the internship, the better your future.

Lately, though, I’ve found myself wondering whether we’ve become a little too focused on climbing someone else’s ladder.

Twenty years ago, I landed what felt like a dream internship with a large global organization in Washington, DC. Every morning, I walked down 17th Street straight past the White House on my way to the office. I remember feeling like I was on top of the world. I was working for important people doing important work in an important city. Isn’t this what it’s all about?

To put a cherry on top of the summer, the organization sent me to its flagship conference, basically the equivalent of that industry’s World Cup. High profile people were there from all over the world. This was it - the proverbial “room where it happens.” And I, the intern, had been given the privilege to be a fly on the wall, getting a sneak peek into what my future might hold.

And I remember sitting in the back of that room, looking around, and having a surprisingly clear thought:

If this is the view from the top of the mountain, this is not the mountain I want to be climbing.

Nothing was wrong with the organization or the people. Many of them were extraordinarily talented and successful.

I just couldn’t see myself there. It wasn’t “me.”

Looking back, I wish I had spent at least one summer working on a startup idea with friends instead.

Not because the startup would have succeeded. Most don’t.

But because I would have learned more by doing than waiting to be told what to do.

When you’re building something from scratch, you have to figure things out for yourself. You talk to customers. You test assumptions. You hear feedback you don’t want to hear. You discover whether the problem you’re solving actually matters to anyone besides you.

You learn how to navigate ambiguity rather than wait for instructions.

Most importantly, you learn how to learn.

When we’re young, we often assume knowledge lives somewhere “out there” and that our job is to find the right expert, company, or internship to give us the answers.

Entrepreneurship teaches a different lesson.

The answers are often uncovered through curiosity and directed action. You learn by taking a step, observing what happens, learning what you have to learn, and taking another. The skill isn’t already knowing. The skill is figuring things out.

As I think about today’s students, I wonder if this mindset is becoming even more important. AI is already reshaping entry-level work. Many of the jobs that once served as apprenticeships may look very different in the years ahead.

So perhaps the question isn’t only, “How do I get the most prestigious internship?”

Perhaps it’s also, “How do I become the kind of person who can create opportunities when they aren’t handed to me?”

Internships can be incredibly valuable. Mine certainly was. It taught me something I couldn’t have learned any other way: success isn’t about reaching the top of a mountain. It’s about discovering whether it’s your mountain in the first place.

And sometimes the fastest way to find your mountain is not by working for someone else’s dream, but by spending a summer exploring one of your own.

-Amy

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Worth Your Time

-Aaron Dinin

In class last week I was chatting with a student who was a bit too focused on how much money he thought he could make building a Silicon-Valley-style venture-backed company. In response, I explained that if his primary goal was simply making money, he’d probably be better off spending five years learning the HVAC business and then starting his own repair company.

To be clear, that’s by no means an easy path to wealth. But people are always going to need air conditioning, and, right now, the world doesn’t have enough skilled humans to install and repair them. Simply put, it’s a safer bet than whatever brilliant app he might have been planning.

A few days later, the student sent me this article from Andreessen Horowitz, and I thought it did a great job explaining the underlying economics. The piece explores why things like air conditioners have become relatively inexpensive while the services required to install, maintain, and repair them have become increasingly valuable. The short version is that technology and globalization tend to drive down the cost of products, but local expertise remains stubbornly scarce.

It’s a good reminder of the underlying reasons why every opportunity doesn’t look like Silicon Valley and also why some of the best opportunities are hiding in plain sight inside industries most people ignore. Entrepreneurs often chase whatever is trendy because that’s where attention is. Meanwhile, enormous businesses are constantly being built around solving unglamorous problems for customers who desperately need help.

-Aaron Dinin

In general, I’m not a huge fan of bringing guest speakers into my classes.

This isn’t the place to unpack all my reasons, and I realize I’m a bit on an island with this opinion. The short version is that most guest speakers end up talking at students rather than engaging with them, and I’m not convinced that’s the best use of classroom time.

However, I do have one major exception: venture capitalists. I love when venture capitalists are able to visit my classes, and one of the advantages of teaching Duke in Silicon Valley this past month is that I’ve gotten to bring in quite a few guests with venture capital backgrounds. In fact, we just had one visit us today, and as I listened to him describe his work, I found myself reminded of something I wish more young entrepreneurs knew. Simply put, I think Investors are one of the most misunderstood parts of the startup ecosystem.

The issue stems from the fact that aspiring founders usually encounter venture capital through media. They watch Shark Tank, they read TechCrunch, and they hear stories about founders raising millions of dollars, and, as a result, they assume investors are basically magical money people sitting around waiting to fund brilliant ideas.

But that’s not what venture capital is. Venture capital is a business model. And understanding that business model is incredibly important for founders because it changes how you think about fundraising.

Take the investor who visited my class. From the outside, students see someone with “venture capitalist” in his title and imagine he spends his days deciding which startups deserve money. But his firm is only a few years old, which means, when he described his actual work, it sounded surprisingly familiar.

He’s networking. He’s building relationships. He’s fundraising. He’s promoting his firm. He’s managing operations. He’s trying to create deal flow. He’s producing content. He’s hosting conversations. He’s building a reputation.

In other words, he sounds a lot like an entrepreneur. And that’s not a coincidence. He is an entrepreneur. His startup just happens to be an investment vehicle, and instead of selling software or consumer products, he’s selling capital and expertise.

That’s why I think it’s so valuable for students to meet investors early. Before you have a chance to meet a lot of VCs, you tend to assume they’re the “important ones” because they’ve got millions — perhaps even billions — of dollars to spend. But once you get to know a few of them, you quickly realize venture capitalists are building businesses, too. As a result, fundraising starts looking very different. You stop treating investors like mysterious gatekeepers who need to be convinced to bless your startup. Instead, you start asking why a particular investor might want to partner with your company?

That’s a much more useful way to think about fundraising because the best venture relationships aren’t really about money. They’re about fit.

In fact, “invest in” may not even be the best phrase.

“Partner with” is probably better. And the best founders understand this.

They don’t walk into fundraising conversations assuming they’re the only ones being evaluated. They recognize both sides are trying to determine whether a partnership makes sense for the two businesses that, at their core, are still just working hard to exist. And it becomes one of the most important lessons young entrepreneurs can learn about fundraising.

After all, venture capital isn’t magic. It’s a market. And markets work best when both sides understand what the other is actually trying to accomplish.

-Aaron

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Worth Your Time

-Jamie Jones

My “Worth Your Time” this week isn’t a book, an article, or a podcast. It’s a mindset. Specifically, it’s about doing something that feels like a waste of time because it’s so inefficient, and recognizing that the inefficiency is exactly the point.

I learned to code in 1995. Fortran 77, a language so dead it’s basically a fossil, then later C++ and HTML. That was decades ago. Which means for most of my career, “building something” has been about partnering with a technical person to bring a vision to life, not necessarily doing it myself.

So lately I’ve been forcing myself to roll up my sleeves. Setting up my own design guidelines and guardrails in Claude. Fumbling through installing OpenClaw and trying to build agents. Installing a VS Code terminal and “writing” software. And Failing. A lot.

The thing is, everyone seems to be talking about the value of these tools, but far fewer are actually teaching themselves to use them. They aren’t getting curious or pushing the boundaries to see what they can and can’t do well. And I get it, being a beginner again is slow and frustrating and deeply inefficient. But that struggle is where the learning lives--and I’ve learned a ton over these past few months.

Don’t just talk. Roll your sleeves up and take the time to get uncomfortable being a learner. It’s 100% worth your time.

-Aaron Dinin

After class this week, a student asked if I’d share some advice for promoting his startup through social media.

Since I spend more time obsessing about social media content strategies than any 40-something probably should, I was happy to chat. I immediately began describing the process he’d need to follow to figure out what kinds of content might resonate with his target audience. Then we discussed building a production schedule so he could post consistently. Then we got into the realities of learning editing software, experimenting with formats, studying analytics, iterating based on feedback, and generally treating content creation like an actual operational function of the business instead of an afterthought.

When I finally stopped talking, he just stared at me for a few seconds with an unsettling mixture of confusion and mild horror. Then he confusedly asked:

“But… isn’t that a lot of work?”

I laughed. Yeah… of course it’s a lot of work. That’s why startups are hard!

One of the biggest misconceptions young entrepreneurs have is that the hard part of entrepreneurship is building the product. And, to be fair, building products is hard. But it’s also the part most entrepreneurs enjoy. You get to tinker with features, refine designs, solve technical problems… basically all the stuff that feels productive and intellectually satisfying. It’s also all the stuff that gives you the comforting sensation you’re making meaningful progress.

But businesses aren’t built from products alone.

Businesses are built from customers.

Unfortunately, getting customers usually involves doing a bunch of work that feels repetitive, uncomfortable, uncertain, and deeply unglamorous. That includes sales, marketing, and everything that goes into those kinds of things. It’s exhausting, time-consuming, slow-moving stuff like follow-up emails, content creation, networking, and customer support. Basically, it’s all the work where you’re asking people to care about something before they have any reason to, which is why it’s such a huge grind.

In fact, the grind of customer acquisition is the main reason so many startups stall out early. Founders convince themselves they’re “working hard” because they’re constantly improving the thing they built while happily avoiding the much scarier challenge of trying to get other humans to actually pay attention to it.

But attention is the job.

And distribution is the job.

Learning how to consistently reach, persuade, and retain customers is the job.

Yes, the product matters. Obviously! But entrepreneurs love to romanticize building while underestimating how much effort goes into convincing the world what you built deserves to exist in the first place.

Unfortunately, this less glamorous part of entrepreneurship doesn’t have a shortcut. But that’s OK, because if there was, successful startups wouldn’t be as valuable, and everyone would have one. In fact, it’s why the real value in entrepreneurship is being able to get customers.

-Aaron

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Worth Your Time

-Aaron Dinin

The article I’m sharing here is worth your time, but not for the reasons we normally share articles in this particular space.

I was browsing headlines this week when I stumbled across this title from Wired: “A Fundamental Principle of Aeronautical Engineering Has Been Overturned.” And even though I know essentially nothing about aeronautical engineering, I immediately clicked. After all, “fundamental principles being overturned” seems important, right?

However, the more I read, the more I realized the article isn’t really about overturning a fundamental principle. It’s mostly about research being done that’s refining our understanding of something scientists already mostly understood. In other words, the headline is doing what headlines increasingly seem to be doing in the digital age… it’s stretching reality in whatever ways it needs to in order to capture our attention. But that’s exactly why I think the article is so interesting from an entrepreneurial perspective.

On one hand, I’m fascinated by how often supposedly settled truths evolve over time. Science, technology, and business all move forward by challenging assumptions people once treated as obvious. And entrepreneurs have to constantly do the same thing. After all, industries change the moment someone questions a “fundamental principle” everyone else took for granted, and that’s when the best opportunities emerge.

On the other hand, this article is also a reminder that novelty itself has become part of the attention economy. Simply put, a title like “Researchers continue refining an existing aerodynamic model” doesn’t generate clicks in the same way “A FUNDAMENTAL PRINCIPLE HAS BEEN OVERTURNED” does.

That tension — the tension between genuine innovation and the performance of innovation — is everywhere right now. AI headlines do it constantly. Startup founders do it. Investors do it. Media outlets definitely do it. Everyone is competing for attention, which means everyone is incentivized to frame change as revolutionary, even when the truth is often more incremental and nuanced.

But the future usually doesn’t arrive in one dramatic breakthrough that instantly destroys everything we thought we knew. More often, it arrives through a thousand small refinements that, over time, quietly reshape the world. And the most successful entrepreneurs tend to be the people who notice those refinements early.

That’s ultimately why I found this article so interesting. I don’t particularly care that aeronautical engineering got “overturned.” But I do care about how the article reveals something important about the modern entrepreneurial environment. We live in a world where attention rewards certainty, novelty, and dramatic framing, even though progress itself is usually messy, incremental, and ambiguous. And if you can learn to separate the performance of disruption from the actual mechanics of change, you’ll have a much clearer understanding of where real opportunities are emerging.

-Aaron Dinin

As I write this, we just wrapped up the first week of the Ronald & Carrie Ludwig Duke in Silicon Valley Program. And while I’m tempted to spend the next month using this space to brag about how great it is, I promise I won’t keep writing West Coast updates like I’m some sort of travel blogger.

However, I do want to take a moment to share one brief story about something that’s become a bit of a tradition.

Every time we bring a group of students out for Duke in Silicon Valley, one of the first visits we make is to the historic HP and Google Garages. For those of you who don’t know, the HP Garage is where David Hewlett and Bill Packard started their eponymous company back in 1939, and it’s now considered the “birthplace of Silicon Valley.” The Google Garage is where Larry Page and Sergey Brin first launched Google.

And as you can see from the photo at the top of this issue, these aren’t particularly auspicious places. In fact, visiting them is usually somewhat awkward and disruptive since it involves bringing a big tour bus and a bunch of students into a very quiet suburban neighborhood. It’s definitely raised more than a few eyebrows.

But that unsuspecting suburban setting is also a huge part of the point of the visit.

Sure, we spend the bulk of the program visiting the campuses of some of the largest and most successful tech companies in the world, and those campuses are wildly impressive. But I love bringing students to a place like the Google Garage and ask them to imagine what it would have felt like to be building Google back then. I mean, sure, today we hear “Google” and think of… well… Google. One of the most powerful companies on Earth. A product so dominant its name became a verb.

But none of that was guaranteed.

Back in 1998, it was just two graduate students working on a search engine in a garage. They weren’t surrounded by the Google mythology, and they certainly weren’t guaranteed any type of meaningful success. Heck, they didn’t even know if anyone would care. If anything, the startup probably looked a little ridiculous to outsiders. “You’re making another search engine?” doesn’t exactly sound like the beginning of a trillion-dollar company.

That’s the strange thing success does in hindsight. It compresses uncertainty. Once something works, we retroactively treat the outcome as inevitable, as though we should have seen it coming all along.

But entrepreneurship never feels inevitable while you’re inside it.

Instead, entrepreneurship feels awkward, unclear, and… small. It feels like wandering around a quiet suburban neighborhood trying to convince yourself something important might someday happen there.

That’s why I like taking students to the garages early in the program. I promise, it has nothing to do with romanticizing Silicon Valley mythology. It’s because I want them to understand how ordinary extraordinary things usually look at the beginning.

The startups that change industries rarely feel important at first. The founders rarely feel certain. And the environments where those companies begin often look laughably unimpressive compared to the stories we later tell about them. And that’s an important entrepreneurial lesson because most people quit long before anything looks meaningful. They assume that if success were really possible, it would already feel bigger, clearer, or more obvious.

But it usually doesn’t.

Remember that most of the time, building something meaningful just feels like doing weird work in unremarkable places while hoping the future eventually catches up to your vision.

-Aaron

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Worth Your Time

-Amy Wyron Robinson

As a professor doing my best to teach in the age of Gen AI, I’ve been thinking a lot about how my students can use it to supercharge their thinking rather than replace it.

In this article, notice how Mark Cuban draws a sharp distinction recently between “people who use AI so they do not have to learn anything, and people who use AI so they can learn everything.” Another way to think of it is the difference between using AI to optimize your workout versus sending AI to the gym for you. Only one of those approaches builds muscle…

And guess what Cuban calls the number 1 skill for entrepreneurs, employees, and students?

Curiosity.

Not prompting acumen. Not tool fluency. Curiosity.

For good or for bad, AI does not create a curiosity muscle. It just rewards whatever entrepreneurial mindset you already bring, and punishes the absence of it faster than any technology that came before.

-Aaron Dinin

This week we’re kicking off The Ronald & Carrie Ludwig Duke in Silicon Valley Program (a.k.a. Duke in Silicon Valley). It’s a monthlong summer program where we bring 24 Duke students out to the Bay Area to explore the startup and technology ecosystem up close. In other words, I’m about to spend the next month running around the center of the startup universe with a couple dozen Duke students, and it’s one of my favorite things I get to teach all year. That’s partly because Silicon Valley is fascinating, and partly because I don’t think enough people stop to ask why it’s fascinating.

Most people approach Silicon Valley like tourists visiting some sort of entrepreneurial holy land. They come expecting inspiration and certainty. The garages… Sandhill Road… the billion-dollar unicorns. And, to be fair, some of the mythology around all that stuff exists for a reason. Silicon Valley really has produced an extraordinary concentration of companies, technologies, and wealth.

But the reason I love teaching Duke in Silicon Valley is because I don’t think Silicon Valley is most interesting as a place to admire. I think it’s most interesting as a place to interrogate.

Silicon Valley is more than just a geographic region. It’s a story about innovation, a story about risk-taking, a story about disruption, and a story about brilliant founders changing the world from garages and dorm rooms and tiny apartments. And, like all powerful stories, it shapes behavior while changing what people believe is possible. At the same time, it attracts talent, capital, ambition, and attention. Heck, entire industries — and frankly, entire careers — have been built around the gravitational pull of that narrative.

But stories are complicated things. They illuminate certain truths while obscuring others. They make some outcomes feel inevitable while simultaneously erasing the thousands of failures surrounding the few success stories we all remember. They create aspiration, they create pressure, they inspire people to build companies, and, as a byproduct, they also convince people there’s only one “correct” way to build them.

Because of all that history and complexity, when I teach Duke in Silicon Valley, I try to approach Silicon Valley through more of what might best be described as a traditional liberal arts lens. By that I mean I don’t want students to simply absorb the mythology. I want them to analyze it and question it while understanding how narratives shape ecosystems and how ecosystems shape human behavior.

Those fundamental human behaviors… those are the things that teach the deeper entrepreneurial lesson. Great entrepreneurs don’t just understand products and markets. They understand the stories people tell themselves about status, success, technology, work, identity, and the future. And if you can understand the stories driving an industry or a culture, you can often understand where that culture is headed long before everyone else does.

And that’s ultimately what makes Silicon Valley so valuable to study. Silicon Valley is more than just the world’s epicenter of startups and technology and innovation. Silicon Valley is a place that shows how powerful a story can become when enough people decide to believe it.

-Aaron

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Worth Your Time

-Aaron Dinin

Since I’m currently out in California teaching Duke in Silicon Valley, this week’s recommendation is designed to give you a taste of the region. I’m suggesting Alice Marwick’s Status Update.

On the surface, it’s a book about social media and self-branding during the early Web 2.0 era. But underneath that, it’s really an anthropological study of Silicon Valley itself. Marwick was a doctoral student at NYU when her partner took a job in the Bay Area, and she ended up embedding herself in the Valley during the rise of Twitter, Facebook, startups, and the now-familiar “personal brand everything” culture that emerged alongside them.

What makes the book so interesting is that it captures Silicon Valley as both a technology hub and a social system. And even though it’s focused on the Web 2.0 days of startup culture, the same issues of status, visibility, hype cycles, networking rituals keep cropping. Reading it now is fascinating because you realize the technologies change, but the psychology of the ecosystem mostly doesn’t. One decade it’s social media. Then crypto. Then AI. There’s always a new wave, a new vocabulary, and a new promise that this time everything is changing forever.

Sure, sometimes things are changing forever. But Marwick’s work is a good reminder that understanding an entrepreneurial ecosystem means understanding the humans inside it. After all, that’s usually where the best stories are hiding.

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.

Most AI tools still require you to be the operator… you prompt, copy, paste, and stitch things together. Manus is different. It behaves like an autonomous AI agent that can take a goal and execute a series of steps on its own. You don’t just ask it questions; you assign it outcomes.

What makes this compelling for entrepreneurs is the shift from assistance to delegation. I’ve used Manus to run market scans across industries, generate and refine customer segments, draft outreach sequences, analyze competitor positioning, and prepare early pitch materials, all in one continuous workflow. Instead of managing ten tools and a dozen prompts, you give Manus a brief: “Help me validate this market and identify the first 50 customers,” and it gets to work.

The real power here is leverage. Early-stage founders have plenty of ideas, but they time. Manus acts like a tireless junior operator who can research, synthesize, and iterate while you focus on judgment and decisions. It’s not perfect, and it still needs direction, but it dramatically compresses the distance between strategy and execution. For entrepreneurs trying to move fast, test assumptions, and do more with fewer people, this is a glimpse of how startups will actually be built going forward.

-Aaron Dinin

Earlier this week we celebrated the retirement of Jon Fjeld, one of Duke Innovation & Entrepreneurship’s former directors and someone who spent a lot of years with me serving as a boss, mentor, and reliable source of advice.

At the end of the event, as people were saying their goodbyes and filtering out, I mentioned I’d love to grab lunch sometime soon. Jon and I hadn’t caught up in a while, and I had a couple projects I’d been meaning to get his perspective on.

Jon laughed and said something along the lines of, “Happy to help, but I’m not sure how useful my thoughts are anymore. I’m getting old.”

It was clearly a joke, but it stuck with me because, the older I get, the more I appreciate the value of “getting old” in a way I just couldn’t seem to understand as a young entrepreneur.

Back when I was first starting my entrepreneurial career, I was convinced I was the smartest person in every room. I thought I understood how things worked. Or, at the very least, I assumed I could figure anything out if I just tried hard enough. As a result, whenever someone told me I lacked experience, I usually heard that as a limitation I needed to push past rather than something I needed to respect.

Fast forward two-plus decades, and even though I almost certainly do know more than I did back then, I feel like I know so much less.

Or, more accurately, I have a much clearer sense of how much I don’t know. I see the edge cases and the tradeoffs that are likely to impact every decision. And I understand how often things that seem obvious at the beginning turn out to be far more complicated in practice.

Thanks that heightened awareness, I find myself craving the perspective of people who’ve been through it before — people like Jon.

And, yes, I promise, there’s an entrepreneurial lesson buried in this shift. It’s a lesson about learning to prioritize experience as quickly as possible, which is something young entrepreneurs struggle with.

Heck, it’s something young people, in general, struggle with. Just look at how quickly they ignore everything their parents say (myself included!).

While I realize, in some respects, that confidence of youth is an asset. After all, in the startup world, you kind of have to believe you can do things you’ve never done before, or you’d never start. However, over time, the skill that starts to matter more than confidence is judgment. And good judgment tends to come from a mix of experience, reflection, and, maybe most importantly, listening to people who’ve already seen versions of the problems you’re trying to solve.

-Aaron

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Worth Your Time

-Shep Moyle

Harvard Business School professor Karim Lakhani is researching how AI is transforming work, companies, and strategy. He argues AI is more than just a tool you use; it’s a teammate you collaborate with. And this goes far beyond automation or efficiency; it changes how decisions are made, how organizations learn, and how startups can compete at scale.

As part of that work, in this video Lakhani posed a provocative idea for entrepreneurs about how AI can drive the marginal cost of expertise down toward zero. In practical terms, that means the smartest and deepest knowledge in a domain is no longer scarce or expensive — it becomes more widely accessible through AI assistance. And when expertise becomes abundant, competitive advantage shifts from having knowledge to knowing how to apply it faster and more creatively than anyone else. He also highlights research showing that individuals working with AI can be as effective as entire teams working without it—a transformative insight for startups where resources are limited.

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.

As Duke I&E’s programming has grown, so has the complexity of keeping it all moving. At some point, managing workflows out of our inboxes, spreadsheets, and Slack messages stopped scaling (and adding headcount wasn’t possible… or even the right answer). So, we introduced Basecamp, a project management tool that has been just the right fit for our team. Sophisticated enough that it does the job, but simple enough that we’ve been able to drive adoption across the organization.

All of our information for each project is stored in a single location that anyone on the team can access. The portfolio view allows me to see where every project across the team stands. All of this without chasing anyone down for a status update or annoying them for a lost bit of information I can’t find in my inbox.

The real kicker is the ability to template recurring projects/tasks. We’ve built out SOPs for our major programs — pitch competitions, workshops, mentor office hours — so if someone’s unexpectedly out the week before a big event, the playbook already exists. Someone can step in without starting from scratch.

Having the right infrastructure in place has allowed for less scrambling and enabled smoother and more consistent workflows.

-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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Worth Your Time

-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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Worth Your Time

-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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Worth Your Time

-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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-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.