Is It Time for Entrepreneur Office Hours to Get an Upgrade?

Entrepreneur Office Hours - Issue #300

Photo by Patti Black on Unsplash

As I began to pull together this issue, I noticed something surprising: This is the 300th issue of Entrepreneur Office Hours.

Yikes… 300 issues. That’s a lot of entrepreneurial musing.

Truth is, when I sent the very first issue of EOH back on October 8, 2020, I had no grand plan. I just wanted to write a little something each week about entrepreneurship that could also serve as a way of sharing my articles for free (getting all of you around that pesky, Medium paywall). But I had no idea where it was going to go. And now, here we are, nearly five years later and 300 issues in.

In that time, my life has shifted significantly. Back then, I was much closer to the days of building venture-backed tech companies. These days I spend most of my energy on content creation, social media, and what’s become my signature teaching philosophy: Learning to Fail. That focus has shaped this newsletter, and most of what you read here covers what might best be described as the earliest stages of entrepreneurship — entrepreneurial mindset, the ideation phases, and “top of the funnel” stuff.

Of course, entrepreneurship is a lot bigger than just those things. And Entrepreneur Office Hours — at least in name — has always seemed like it ought to reflect more of that full journey.

This shortcoming is something I’ve been thinking about a lot lately. I feel like this newsletter, in its current form isn’t so much “Entrepreneur Office Hours” as it is “Aaron Dinin writing about what he wants to write about, which is mostly very early stage entrepreneurship and marketing.”

At the same time as my entrepreneurial interests have narrowed, I’ve watched Duke’s entrepreneurship program grow. When I first started teaching in Duke’s Innovation & Entrepreneurship program, I was the only full-time entrepreneurship faculty member. Now we have an incredible team who each bring their own expertise — venture capital, growth strategy, private equity, AI, and more.

So I’ve started wondering: what if Entrepreneur Office Hours wasn’t just me? What if I occasionally invited some of my colleagues to contribute their voices and perspectives? Would this become a richer resource for all of you if it represented more than one slice of entrepreneurship?

I don’t have an answer yet. In fact, that’s why I’m asking you. Do you like this idea? How would you feel if EOH evolved into something bigger? Or would you rather keep it just me, week after week, doing what I’ve always done?

Hit reply and let me know. I’d love to hear your thoughts.

-Aaron

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This week’s new articles…

Why Great Startup Founders Should Sound Boring

The best startup founders aren’t nearly as charismatic as most people think, and that’s a good thing.

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The Startup Skill Nobody Talks About (But Every Founder Needs)

When you’re building a company, the most important skills rarely have anything to do with your product.

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Office Hours Q&A

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QUESTION:

Hi Aaron,

I’m a few months into building my first SaaS product. I’ve been coding everything myself, and I think it’s finally good enough for early users. But I’m stuck on pricing. I don’t know whether to charge right away, offer a free trial, do a freemium model, or just keep it free while I get feedback.

How do you recommend thinking about pricing when you’re launching something new, especially when you’re not sure how much value users are actually getting yet?

Thanks,
Nate

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Lot’s of people act like there’s a science to startup pricing… like there’s some magic formula for figuring out how much to charge for a brand new product nobody’s ever used. But if there is, I haven’t found it.

I’ve seen people try all sorts of strategies. Some base their pricing on costs, which sounds logical until you remember that most early-stage startups are wildly inefficient. When you're small and building everything yourself, your per-user costs are probably awful. So basing your pricing on costs is kind of like basing the price of a car on what it would cost to build one by hand in your garage.

Others try to base their pricing on competitors. That can help anchor things, sure. But copying what someone else charges assumes your users, product, and value prop are all the same. They’re not. Pricing yourself to match someone else often just makes you look like a worse version of them.

Then there’s freemium or free trial models. Those can work — and they’re especially helpful if you need volume to learn from users — but it’s a slippery slope. If you’re not careful, “free for now” becomes “free forever,” and then you’re stuck trying to convince people to pay for something they’re used to getting for nothing.

So what’s the right answer?

Honestly… I don’t know. Nobody does. That’s the point.

Pricing isn’t a decision you get right. It’s a process you run.

The goal shouldn’t be to find the perfect price on day one. It should be to build a system that helps you discover the right price over time. That means charging something — even just a little — and seeing what happens. It means raising prices and seeing who churns. It means experimenting, observing, adjusting, and repeating.

Simply put, pricing is trial and error. It’s testing and learning. It’s how you figure out what your users actually value, how urgently they need it, and what they're willing to trade for it. And those are all things you’re going to have to figure out.

Don’t try to be right from the start. Just start trying.

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