-Shep Moyle

Editor’s Note: Last week, Jamie wrote about quitting your job and going “all in” on your startup. In case you missed it, we’re sharing a link here since, this week, Shep takes a look at the other side of quitting… knowing when to quit your startup and move onto something else.

I had a recently graduated MBA student reach out to me with a tricky question about his startup. And this wasn’t a student with a half-formed idea or a weekend project. This was a smart, talented, experienced professional who’d spent nearly two years building a real company that had four founders working remotely around the globe. As a result, alongside the standard firehose of investor conversations, product decisions, and team tensions, they constantly found themselves in late-night Zoom meetings and early-morning customer calls.

By this point, they’ve done many of the things we tell entrepreneurs to do. They have a product, they’ve sold it to customers, and they’ve listened to the market well enough that they’ve been able to successfully learn, pitched, refine, and keep going.

And now, after investing lots of time, money, emotion, and personal identity into their company, the question they wanted help with was painfully simple.

“How do we know when to quit?”

I paused on the founder’s phrasing. It wasn’t, “How do we know whether the business still has a path?” or “How do we evaluate the evidence?” or “How do we decide what’s next?”

It was: “How do we know when to quit?”

The emotion is what makes these decisions so hard for founders. They’re not just analytical. They’re personal. Deciding when to quit is wrapped in ego, identity, loyalty, sunk cost, and fear. Quitting sounds like failure. Quitting sounds like weakness. Quitting sounds like letting down your co-founders, your investors, your customers, your family, and maybe most painfully, the younger version of yourself who believed this thing was going to work.

I began my response the way I often do when I get asked this particular question. I told him, “The fact that you’re asking the question is clue number one.”

To be clear, that doesn’t mean the answer is automatically to stop. But it does mean something inside you is trying to get your attention. Entrepreneurs are famously good at ignoring reality when persistence is required. I’d even go so far as to say it’s part of their talent. But it can also become a trap. After all, there’s a difference between resilience and denial… grit and ego… believing in a vision and refusing to read the scoreboard.

So we went to the facts.

If I walked in as a board member or investor, what would the numbers tell me? What evidence do we have that this should continue? What do we have to believe to be true for this to become the company we imagined? What is the actual probability of reaching our short-term and long-term goals? Not the hoped-for probability or the founder-pitch probability. The honest one.

In this case, the world had changed. AI tools were emerging that fundamentally altered the competitive landscape, the customer need, and the urgency of the problem. At the same time, some important things hadn’t changed. The sales cycle was still long. Customer decision-making was still slow.

Then I asked a more personal question: “How does this venture serve your goals now?”

That’s a question we don’t ask enough. This student (and his cofounders) had already gained enormous value from the experience. He’d already learned strategy, fundraising, selling, pitching, customer discovery, team leadership, product development, and the reality of building a scalable enterprise. In other words, he’d certainly become a different kind of professional because of the attempt.

So the question became: What do you still have left to learn? Are you energized by the next mountain? Do you wake up excited for the next two years of this specific fight? Or are you staying because stopping feels embarrassing? Don’t confuse unpleasant decisions with hard decisions. Hard decisions require the analysis and the insights required for understanding. Unpleasant decisions are ones where we know the answer — we just don’t want to face the emotional consequences.

All businesses have a lifecycle. Some are short. Some are long. Some need a pivot. Some need more capital. Some need a different team. And some need an honest ending.

I know this personally. I made the painful decision to close my 97-year-old family business. I wasn’t because there wasn’t market or we were losing money or because we couldn’t have sold it. I closed it because I knew, if I was honest with myself, I didn’t have the fire in the belly to commit the next ten years of my life to making it work. I had already invested 32 years as an owner, CEO and Chairman. I had all the financial rewards and ego i could have ever imagined.

Was it difficult to make that decision? Absolutely. Was it the ending I imagined? No. But it was the right decision for me and for my family.

That’s the lesson I wanted this student to hear. You’re not quitting; you’re choosing. You’re not failing; you’ve gotten clarity. You’re not letting people down; you’re deciding what chapter of your book you want to write next.

Businesses come and go. Markets make sure of that. Products come and go, too. And people move on. And strangely, the world keeps spinning. What remains are the relationships, the scars, the lessons, the courage, and the person you became because you tried.

Because of that, entrepreneurship isn’t just about knowing when to persist. It’s about knowing the difference between persistence and denial. It’s about being brave enough to face the facts, and even braver to face yourself.

Sometimes the most entrepreneurial act is not starting the company. Sometimes it’s knowing when to let it go, take the learning, and go find the next mountain to climb.

-Shep

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Worth Your Time

-Jamie Jones

This week the White House released “Science: A New Golden Age,” a report that outlines a perspective (and series of recommendations) on the U.S.’s science investment priorities.

I’m not sharing the report because I’m expressing a policy opinion; I’m sharing it because this document is a map of where the money, talent, and infrastructure behind American innovation may be headed next. As an entrepreneur and innovator, you likely live downstream of these decisions.

The best founders I know are always looking for where the puck (and money) is moving. This report is a roadmap of exactly that.

-Jamie Jones

A recent alum asked me to hop on a call last week to walk me through a startup he’s building. He’s four or five months in — far enough to have had a handful of customer conversations (not nearly enough, if you ask me) — and he’s doing all of it around a full-time job that pays the bills. He walked me through what he’d built, and near the end came the question I get more than almost any other:

Should I quit my job and go all in?

I’ve learned to slow down when I hear that one, because it’s rarely the question people think they’re asking. On the surface, it sounds like strategy — runway, timing, risk. But most of the time, someone asking whether to go all in isn’t asking me to help them think. They’re asking for permission. To be told they’re brave.

It reminds me of students I wrote about recently who, underneath all their sharp questions for a visiting CEO, were really just asking her to promise everything would be okay. It’s human. But it’s also a tell — because “go all in” almost always carries a charge of impatience, a hunger not just for the business to work but for the identity of being a full-time, no-safety-net founder. And that hunger is a bad advisor.

Here’s what surprises people: the bet-everything founder is mostly a myth we tell after the fact. When Joseph Raffiee and Jie Feng tracked more than 5,000 people over fifteen years, the ones who kept their day jobs and built on the side were about a third less likely to fail than those who leapt. Adam Grant made the point famous in Originals; a separate paper put it bluntly in its title: “Don’t Quit Your Day Job. (Garcia-Perez et al.)”

The research helps unpack why you see a difference, which is that “going all in” isn’t a strategy but a resource decision. You pour your scarcest input, time, into the venture. And pouring more time into something that isn’t working yet doesn’t guarantee it’s going to work (sooner or at all), but you still have rent/mortgage due.

The day job, meanwhile, is protecting your judgment. A founder whose survival depends on the thing working this month can’t say no to a bad customer or wait for a real answer instead of a convenient one. Staying employed a little longer allows you to keep your head clear enough to read the evidence more objectively.

So the question I sent him home with wasn’t “are you ready?” It was: how will you know when there’s enough there-there? You should go full-time not when you are overwhelmed by the excitement and passion, but when hedging your time has become the bottleneck — when the demand is real and the only thing choking it is that you’re doing this at 6am before work.

Until then, continuing your full-time role while building your startup isn’t playing it safe because making real progress in the margins — under constraints, without permission — is the best test of whether there’s something there.

I didn’t tell him he was brave. I told him to go have twenty more customer conversations and try to secure 3-4 pre-sales before we talk about anyone quitting anything. Deep down, I think that’s the answer he was hoping for.

-Jamie

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Worth Your Time

-Aaron Dinin

I feel like a bit of a shill for putting this here, but I promise nobody is paying me. I just wanted to use the space this week to plug Jia Jiang’s new book, Easy Discipline. Jia, as a reminder, is a Duke Fuqua alum and the author of Rejection Proof, which I mentioned here a few weeks ago.

Rejection Proof found its way back on my radar after getting an advance copy of Easy Discipline. Now that the new book is officially out, I thought I could give that one a quick recommendation, too.

Specifically, I love the premise because it’s a strategy I’ve tried to live by for years. Jia argues that the most successful people aren’t necessarily the ones with the most willpower. They’re the ones who’ve designed their work so they actually enjoy doing it. Instead of relying on grit alone, they build systems and habits that make it easier to keep showing up.

As you’d expect, the book goes into much more detail — including plenty of practical advice on how to do that yourself. So if you’re someone who’s ever wondered why some people seem effortlessly disciplined while everyone else is white-knuckling their way through life, I think you’ll find it worth the read.

-Aaron Dinin

Every month, the Duke Innovation & Entrepreneurship team does some sort of team building activity. And this month, we did improv.

Sure, you might read “improv” and picture aspiring comedians standing on a stage pretending to be pirates while arguing with squirrels. And that’s definitely a manifestation of improv, but, at its core, improv is about entertaining and communicating. And it’s about learning to listen, react, collaborate, and build on the ideas of other people.

In other words, it’s a surprisingly useful skill for entrepreneurs.

For example, as we practiced improv together, one exercise, in particular, struck me as particularly valuable for entrepreneurs. So valuable, in fact, that you might consider trying it with a friend.

The person leading our improv session instructed everyone to pair up and have a simple conversation. The catch was that all our responses to each other had to begin with the classic improv phrase: “Yes, and...”

If you’ve ever done any improve before, you surely know what happened. Every conversation naturally expanded. Even when someone suggested something a little odd, nobody judged it. “Yes, and…” encouraged us to explore it and find unexpected ways to build on it.

Then the facilitator changed the rules. This time, every response had to begin with, “Yes, but...”, and the entire energy of the room changed almost instantly as the conversations started feeling like they were trying to move through tar. We made progress, but it was slow and argumentative.

After a few minutes of, “Yes, but…”, the facilitator changed the instructions again. We had to respond to each other by starting every phrase with, “No, because...”

That phrase absolutely killed the conversations. All ideas got rejected before they had a chance to become anything.

Finally, after a few minutes of “No, because…” we returned to “Yes, and...”, and the energy immediately came back into the room.

To be clear, I’m not telling everyone they should run around saying “Yes, and…” to everything. Sure, that works for improv. But entrepreneurs need to be more practical.

Instead, what caught my attention was how little it took to completely change the trajectory of an interaction. We weren’t changing the people or the ideas. We were just changing a couple words at the beginning of every sentence. But those two words completely changed what became possible.

It’s an interesting lesson for entrepreneurs because building companies is, fundamentally, a collaborative activity. You’re constantly responding to teammates, customers, investors, partners, and employees. The words you choose either invite people to keep building with you or (unintentionally) encourage them to stop.

Again, please don’t run around saying “yes” to every idea. Some ideas really are bad ideas. But there’s a meaningful difference between evaluating an idea and prematurely ending the conversation.

The best entrepreneurs I’ve met seem to understand that distinction. They’re remarkably good at creating conversations where ideas have room to breathe before they’re judged. And sometimes, enabling those conversations starts with something as simple as choosing “Yes, and...” instead of “Yes, but.”

-Aaron

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Worth Your Time

-Amy Wyron Robinson

This week I’ve been thinking about a piece from Wes Kao on what it actually means to be inspiring.

One idea in particular has stayed with me: we tend to describe arguments we agree with as “logical” and arguments we disagree with as “emotional.” In reality, emotion isn’t the opposite of logic. A strong argument with flat delivery is still strong, and a weak argument delivered passionately isn’t automatically going to win over the listener.

For entrepreneurs, this distinction matters. Founders often obsess over presentation skills, storytelling techniques, and stage presence. And they should! Those things matter. You should absolutely work on your delivery. But great delivery can’t rescue a flawed argument.

The best pitches succeed because the underlying logic is sound. The problem is real. The customer insight is compelling. The proposed solution makes sense. The business has a credible path forward. When those pieces fit together, passion amplifies the message. When they don’t, charisma can only carry you so far.

As you prepare your next pitch, please spend at least as much time strengthening the argument as you do polishing the presentation. Investors, customers, and partners may appreciate your enthusiasm, but they’ll ultimately decide based on whether your story holds together.

-Amy Wyron Robinson

I recently worked with a cohort of young entrepreneurs preparing to pitch their ideas. As always, I loved the coaching part.

I am in my happy place when I’m helping founders sharpen their story, clarify their thinking, and find the thread that makes an audience lean in. What I don’t love is judging.

In fact, being a judge is one of my least favorite jobs to be done.

I was reminded how little I enjoy judging when I was recently asked to judge a pitch competition sponsored by Inc. Magazine for high school entrepreneurs. The founders were eager. Their ideas were creative. But what jumped out at me most wasn’t the pitches themselves.

It was the other judges.

As we discussed the finalists, it became clear that we weren’t all evaluating the same thing.

Some judges rewarded great storytelling. Others cared more about opportunity size. Some cared most about execution and traction. Others were drawn to founders who demonstrated deep expertise and clearly knew their subject matter inside and out. And others cared more if the imaginary revenue projections were math-ing…

The same pitch could land completely differently depending on who happened to be listening and what their ear was listening for.

Which leads me to something every founder (and professor) eventually learns:

There is no universal definition of “best.”

We like to believe that competitions, investors, customers, and markets are objective. That if we just work hard enough, polish enough, and put in the reps, there will be a clear winner.

But entrepreneurship doesn’t work that way.

The “best” pitch isn’t a formula (although there are some very important boxes to check). It’s not a spell you’re casting on others. It’s a conversation between a founder and an audience, and every audience brings its own biases, experiences, agendas, and hard-earned scars.

An investor who spent years losing money on marketplace businesses hears a marketplace pitch differently than one who made a fortune investing in them.

A customer who has lived with a super specific problem for years sees huge potential where others see a narrow niche.

A judge who values potential will listen for different signals than a judge who values traction.

The goal, then, is not to create a pitch that every person will love.

That’s impossible.

The goal is to create a pitch so compelling that the right people can’t ignore you.

The founders who ultimately stood out in the competition didn’t necessarily have the most beautiful slides. They weren’t always the most charismatic, either.

They had ideas grounded in insight and evidence. They were clear and simple. They understood the problem deeply. They had practiced. They could articulate why the world should change and why they were the people to make that change happen.

Most importantly, their ideas felt inevitable.

They answered the questions the audience is asking, whether they say them out loud or not:

Why this?

Why now?

Why you?

As founders (and humans) we spend far too much time worrying about whether we’re the best at something.

There is no objective “best” pitch, founder, or startup.

There are only people trying to convince other people that a different future is possible, the time for that change is now, and you are the one person on earth to bring this vision to life.

-Amy

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Worth Your Time

-Shep Moyle

Sam Altman may have just given us a preview of the next era of entrepreneurship. In this article from Inc. Magazine, OpenAI is offering $2 million in OpenAI API tokens to startups in Y Combinator’s Spring 2026 batch in exchange for an undetermined amount of future equity. Not cash for equity. Not office space for equity. Not accelerator programming for equity. Compute for equity. That may sound like a clever startup financing idea. I think it is much bigger than that.

For decades, the answer to the startup resource question was obvious. Founders needed capital. They needed money to hire engineers, build software, buy infrastructure, acquire customers, and survive long enough to find product-market fit. But AI changes the math.

If a founder can use AI to write code, generate content, build prototypes, analyze markets, test ads, automate customer support, build internal workflows, and personalize products, then the scarce resource may no longer be only money. The scarce resource may be intelligence at scale. And intelligence at scale requires compute. So is compute becoming the new cash? I think the answer is yes, at least partially.

Cash still matters. Payroll matters. Sales matter. Customer acquisition matters. Legal fees, travel, distribution, data, and real-world execution still matter. But for AI-native startups, compute may become what manufacturing capacity was to industrial companies, what shelf space was to consumer brands, what server capacity was to internet companies, and what oil was to the twentieth-century economy. It is not just an expense. It is an input into possibility.

Would I take the deal? Maybe. But not blindly. If I were a YC founder, I would want to know what I was really giving up. Two percent of a company sounds small when the company is just an idea, a pitch deck, and a few people sitting around a table. It sounds very different if that company becomes worth a billion dollars. I would also ask whether the compute accelerates learning or simply subsidizes waste. Free tokens can make founders sloppy. The goal is not to use more AI. The goal is to learn faster, build faster, sell faster, and get closer to the truth faster.

I would ask whether I was becoming too dependent on one platform. If my product, workflow, cost structure, and roadmap are all tied to OpenAI, am I building a company or am I building a feature in someone else’s ecosystem?And I would ask what OpenAI sees that I may not. If OpenAI wants equity in hundreds of startups in exchange for compute, they are not just being generous. They are buying insight, option value, ecosystem influence, and a front-row seat to the next generation of AI-native companies.

This should also get the attention of venture capital firms. Not because OpenAI is replacing venture capital tomorrow. But because the value stack around startups is changing. Traditional venture capital offers cash, credibility, pattern recognition, networks, hiring help, and follow-on financing. That still matters. But what happens when a platform company can offer something more immediately useful? What happens when OpenAI, Anthropic, Google, Amazon, Microsoft, Nvidia, or Meta can say to a founder: we will give you the fuel to build? That is a different kind of capital.

In the AI era, money is necessary but less differentiated. What is scarce is unfair advantage. The real question for investors may become: what do you bring that helps this company learn, build, sell, or scale faster than anyone else? If the answer is only money, that may not be enough. Will YC companies take the deal? Many will. Of course they will.

Early-stage founders are resource constrained. Equity feels abstract. Compute feels real. Two million dollars of AI capacity could let a young company build more, test more, serve more customers, and try things that otherwise might be impossible.But the best founders will not treat this as free money. They will treat it as high-octane fuel. And high-octane fuel is only valuable if you know where you are driving. The dangerous founder response is, “Great, now we can use AI everywhere.” The disciplined founder response is, “Where can this compute create proprietary learning that compounds?”

The pricing question is also fascinating. Cash is easy to price. A dollar is a dollar. Compute is different. Its value depends on who is using it, for what purpose, at what stage, with what model, and with what outcome. For one startup, $2 million of tokens may be an expensive science experiment. For another, it may be the difference between a demo and a real product. For another, it may unlock an entirely new business model that could not have existed five years ago. So the real value of compute is not just its sticker price. It is its option value.

Compute allows founders to run more experiments, serve more users, train or fine-tune more systems, personalize more deeply, automate more workflows, and compress time. And in entrepreneurship, compressed time is often the most valuable thing there is. If you can learn in two weeks what used to take six months, you have not just saved money. You have changed the slope of the company.The bigger implication is that compute may only be the beginning. If compute can be traded for equity, what else can?

Data can be traded for equity. A hospital system, retailer, university, logistics company, or financial institution with proprietary data may become a strategic investor in startups that can turn that data into products, insights, and outcomes. Distribution can be traded for equity. The hardest thing in many startups is not building the product. It is reaching the customer. A company with trusted customer access may have something more valuable than a check. Workflow access can be traded for equity. Imagine a startup embedded inside a law firm, hospital, manufacturer, university, or sales organization, building AI tools around real pain points in real time. The company providing the workflow becomes an investor through access. Expertise can be traded for equity. Not advisory shares in the old ceremonial sense. Real expertise. A world-class doctor, engineer, operator, teacher, CFO, or sales leader can help train, validate, and shape a product in ways money cannot.

Brand trust can be traded for equity. In a world full of AI-generated noise, trust becomes more valuable. A respected institution or community can reduce customer hesitation and create legitimacy. Talent networks can be traded for equity. Access to elite builders, researchers, domain experts, and operators may become a capital source. Regulatory navigation can be traded for equity. In health care, finance, education, energy, and defense, knowing how to move through complexity is not a side service. It is a strategic asset. Customer commitments can be traded for equity. Early customers may increasingly say, “We will help you build this, test it, and buy it, but we want ownership.” Community can be traded for equity. A deeply engaged audience may be more valuable than an ad budget. Attention is everywhere. Trust is scarce.

That is what makes this story so important. The old founder question was, “How much money do I need to raise?” The new founder question may be, “What resource changes the trajectory of my company?” For some founders, that resource is cash. For others, it is compute. For others, it is data, distribution, trust, talent, credibility, customer access, regulatory insight, or speed. Entrepreneurship has always been about the pursuit of opportunity without regard to the resources currently controlled. But AI changes the resource map.

The founder of the future may not ask only, “Who will fund me?” The founder of the future may ask, “Who can give me the unfair advantage I cannot buy later?” I would not dismiss this OpenAI offer as a publicity move. I would also not treat it as charity. This is a platform company making a strategic bet that the next generation of startups will be built on AI infrastructure, and that owning a small piece of many of them may be very valuable. For founders, this is exciting and dangerous. For VCs, it is a warning shot. For universities, it is a wake-up call. For students, it is an invitation.

The tools are no longer theoretical. The cost of building has collapsed. The speed of experimentation has exploded. The definition of capital is changing. The distance between idea and product is shrinking every day. So the question is not just whether you would trade equity for compute.

The better question is this: If someone gave you $2 million of intelligence tomorrow, would you know what to do with it?

-Aaron Dinin

This week, a couple of us from Duke Innovation & Entrepreneurship sat down with Duke’s Vice Provost for the Arts to talk about ways our programs might collaborate.

To be clear, that part wasn’t new. We’ve been working with Duke’s arts community for years, and some of my favorite projects have come from those partnerships.

What was new was the context hanging over the conversation. Specifically… AI.

Like with most of you, I’m sure, the past few years have included lots of conversations with entrepreneurs, engineers, venture capitalists, and technologists about what AI might mean for the future of work. And one of the observations that seems to come up over and over again is that the careers we’ve traditionally considered “safe” — computer science, software engineering, technical knowledge work — suddenly don’t seem quite as safe as they once did.

At the same time, I’ve had plenty of conversations and read lots of thought pieces arguing the things we associate with artists (e.g. creativity, taste, originality, emotional resonance, etc.) are becoming more valuable because they’re harder to replicate.

I’m sure you’ve heard some version of that argument before. I realize none of this is groundbreaking.

Instead, what struck me was a realization that I’ve almost exclusively been discussing this stuff with other “tech people” and “business people.” I honestly couldn’t remember the last time I’d sat down with artists and asked them what they thought.

Do they agree with this narrative? Are they excited by it? Skeptical? Does it even match what they’re experiencing? Or is this just another story the technology world is telling itself about the future?

I don’t have answers. And my one meeting with the Duke Arts Provost isn’t exactly statistically significant. But it did remind me of something I think entrepreneurs forget surprisingly often. We spend lots of time talking about people instead of talking to them.

But remember, the best entrepreneurs don’t just form opinions inside their own bubbles. They deliberately seek out the people whose perspectives are missing from the conversation. And sometimes those perspectives confirm what you already believed. Sometimes they completely reshape how you think about a problem. Either way, having the conversation is a necessary step, and I feel like I need to start having this particular conversation about the impacts of AI on the arts with more people who are deeply invested in the arts.

In fact, I’d be curious to hear from some of you. If you work in the arts — or work closely with artists — how are these AI conversations landing where you are? Are you optimistic? Concerned? Rolling your eyes at the whole thing? Hit reply and let us know, or, better yet, drop a comment.

-Aaron

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Worth Your Time

-Jamie Jones

Do customers keep telling you your product is “really interesting,” but then you can’t close the sale? Are you getting meetings that feel great but then your contact goes silent?

If any of this feels familiar, this HBR piece is worth your time. The authors interviewed more than 250 founders across six continents, then compared the results to a similar study they ran a decade ago. They concluded that the sales playbook most founders are running was built for a market that no longer exists. Not today… not when sustainable competitive advantage is crumbling as every company has the tools to build rapidly.

The article both diagnoses the challenges that software startups face and offers a framework to think about changes you may want to consider to move from positive calls to closing the deal.

-Jamie Jones

Last week, I ran a design thinking workshop for the entire staff of the Fuqua School of Business. That’s 180 people.

I want to be clear about how ill-advised that is. Design thinking works because it’s intimate. Small groups, fast cycles, lots of back-and-forth. No one in their right mind runs one for the entire staff of a business school at once. But, the Dean (my boss) asked, and so how could I say no?

The topic was improving the student experience, and the room held just about everyone who makes Fuqua run. Building and maintenance. IT. Student services. Admissions. Marketing. People whose work shapes a student’s day in ways most of us never see. We mixed the tables on purpose, so that the people who sat together weren’t the people who already worked together. The Dean came to show she was invested in what the staff had to say. And then we asked everyone to dig into the same question from the wildly different vantage points of their actual jobs.

I went in thinking the value would be the ideas. And the ideas were good. The Dean and her team walked away with a real list worth acting on.

But that’s not the moment I remember.

The moment I remember is wandering between tables and overhearing things like “oh, I didn’t know that’s how classroom scheduling worked” and “wait, students are struggling with that?” People who had worked in the same building for years were learning, for the first time, how the other half of the operation actually functioned. They weren’t just generating ideas. They were building a map of the organization in real time, and building it together.

The next day, colleagues stopped me in the hall. Not to talk about the ideas. To tell me how much fun they’d had, and how nice it was to finally meet people they’d been emailing for years without ever sharing a table.

That’s when it clicked for me. While the workshop produced several interesting ideas, what it really produced was understanding, and connection, and a little more shared culture than we’d had the day before. While the excuse to come together may have been to generate new ideas, the real result was the community itself and our deeper understanding of each other and the organization.

If you are leading a team (especially founders, who are wired to optimize for output), you are likely obsessed with efficiently delivering a solution. And so the inefficient stuff, the part where people who don’t normally talk actually talk, the part where you stop “work” to come together for a half-day to connect and engage, gets cut first because it looks and feels like overhead.

But that inefficient stuff is often where the real value lives. A team that understands how the whole machine fits together makes better decisions for years. People who trust each other move faster when it counts. You can’t put that on a slide, which is exactly why it’s so easy to skip.

Sometimes the point isn’t the thing you set out to make. It’s everyone you made it with and the community and culture you built in the process.

-Jamie

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Worth Your Time

-Aaron Dinin

This week, I found myself messaging with Jia Jiang, author of Rejection Proof. For those who don’t know the story, Rejection Proof is the story of Jia intentionally getting rejected for 100 straight days.

That conversation brought back a fun memory. Years ago, when I first started teaching Learning to Fail, I assigned Rejection Proof to my students. At some point, they discovered Jia was a Duke alum and decided they wanted him to guest speak in class. So they did something that felt appropriately on-theme: they reached out and asked.

To their delight, he said yes.

This was back in the pre-Zoom era, so Jia joined us via Skype and spent time discussing the central lesson of his book… that rejection isn’t nearly as dangerous as we imagine it to be.

That’s an especially important lesson for entrepreneurs because entrepreneurship is, at its core, a profession built around hearing “no.” Customers say no. Investors say no. Partners say no. Employees say no. Sometimes the market itself says no.

The founders who survive aren’t necessarily the ones who avoid rejection. They’re the ones who stop treating rejection as evidence they should quit. Instead, they learn to see it as information, feedback, and an unavoidable part of building anything meaningful.

If you’ve never read Rejection Proof, it’s worth your time. And if you’re currently sitting on an email, pitch, proposal, or request you’re afraid to send because someone might reject it, consider this a sign you should send it.

-Aaron Dinin

After spending the past month teaching Duke in Silicon Valley, and another week on vacation in California with my family, I finally made it back to Durham.

For me, that meant a return to the office. But before that, I had to take my daughters to summer camp. By chance, both girls are starting new camps this week. Neither knows anyone, and neither has ever been before. So, as you might imagine, both were a little nervous when I dropped them off.

As we sat in the car before walking in, I found myself giving what I assume is a fairly standard piece of dad advice:

“Nervous is good.”

To be clear, I don’t mean debilitating anxiety is good. “Good nervous,” I explained, “is that feeling in your stomach when you’re about to do something that matters. It’s the feeling that comes from uncertainty mixed with hope, and the feeling that exists because you care about the outcome, which is a good thing.”

I went on to tell them something I often have to remind the entrepreneurs and students I work with: “If you’re never nervous, you’re probably not challenging yourself enough.”

What’s funny is that after dropping them off, I headed to the I&E office to prepare for a new class I started teaching this week, and, as I drove in, I realized I was feeling nervous, too.

At first, I was confused about why I felt that way. After all, at this point in my career, I’ve taught hundreds of classes. Plus, the class I’m teaching isn’t technically “new.” It’s a one-week online course for about 50 graduate students, and this is the fifth time I’ve taught it. I know the material. I know the activities. I know the pacing. By any reasonable standard, I should feel completely comfortable.

And yet, every single time I start a new class, I’m nervous. But I’m not nervous because I’m worried it’s going to go badly. I’m nervous because I want it to go well. I care whether the students learn something useful, and I care whether the discussions are engaging, and I care whether I’m bringing enough energy and preparation to justify asking these students to spend a week of their lives learning with me.

In other words, I’m nervous for exactly the same reason my daughters were nervous: The thing I’m doing matters.

I bring this up because, increasingly, I feel like the entrepreneurs I work with are treating nervousness like a signal something is wrong. They interpret uncertainty as evidence they aren’t ready, aren’t qualified, or shouldn’t move forward.

But most of the time, nervousness isn’t a warning sign. It’s a sign you’re doing something meaningful.

Whether you’re starting a company, launching a product, pitching investors, hiring your first employee, taking a new job, teaching a new class, or walking into a summer camp where you don’t know anyone… those experiences all involve growth. And growth tends to feel a lot like nervousness while it’s happening.

So if you’re feeling a little nervous about something this week, maybe don’t rush to make the feeling go away.

Maybe just take it as evidence you’re doing exactly what you’re supposed to be doing.

You’re growing, and that’s a good thing.

-Aaron

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Worth Your Time

-Amy Wyron Robinson

One of the most thorough and thoughtful pieces of startup content I’ve come across recently is Rob Snyder’s three-hour lecture, The Physics of Startups. When I transitioned from 20 years in early-stage startups to teaching entrepreneurship at Duke, I spent a lot of time searching for frameworks that matched what I had actually experienced in the field. Many felt either too simplistic or disconnected from reality. When I discovered Rob’s work, I had the uncanny feeling that he’d been looking over my shoulder for the last two decades.

His central argument is deceptively simple: customer demand is the only thing that really matters. He challenges much of the conventional startup advice around identifying “pain points” and offers a more nuanced and rigorous way of thinking about why some ventures gain traction while others don’t. Whether you’re a founder, investor, or entrepreneurship educator, this is one of the most thoughtful frameworks I’ve seen for understanding startup momentum and market pull.

-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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-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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-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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-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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-Aaron Dinin

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

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

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

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

Tools We’re Tinkering With

-Amy Wyron Robinson

Editor’s note: All resources suggested in this section are based on our opinions. These aren’t affiliate promotions and we don’t generate commissions.

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

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

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

-Aaron Dinin

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

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

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

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

From my perspective, though, it looked exactly right.

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

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

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

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

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

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

That’s how startup growth works!

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

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

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

Remember, in entrepreneurship, success takes time. Always.

-Aaron

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

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-Shep Moyle

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

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

Tools We’re Tinkering With

-Shep Moyle

Editor’s note: All resources suggested in this section are based on our opinions. These aren’t affiliate promotions and we don’t generate commissions.

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

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

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

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

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

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

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

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

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

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

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

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

-Amy

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-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.