Anyone Want Some Real Entrepreneur Office Hours?
Entrepreneur Office Hours - Issue #264
Help me answer a quick question: How many of you would be interested in joining me for a 60 minute “Entrepreneur Office Hours” Zoom where I’ll give you feedback and advice on your startup in exchange for letting me record and publish the conversation?
If you are, let me know here.
Now, for some background — This question stems from the podcast I’ve been testing for the past couple months with my friend, Chris Leithe, who also happens to be one of the smartest entrepreneurs I know.
So far, we’re two dudes talking randomly about entrepreneurship, and it feels a bit wasteful considering I get dozens of people reaching out every week for startup advice. We’ve started wondering: What if we spent our podcasts talking with actual entrepreneurs about their actual problems? You know… kind of like the title of this newsletter — Entrepreneur Office Hours.
Anyway, it could be a great idea. It could also be a terrible idea. Either way, as all of us entrepreneurs know, the best way to validate ideas is to test them. And Test #1, in this case, is the message you’re reading right now to find out how many of you are interested in participating . If you’d like to join an episode and share your startup (and it’s problems), fill out this form.
If there’s enough interest, I’ll be in touch.
Thanks!
-Aaron
Podcast: ThoughtWave Episode #9
How Should I Price My Product?
Pricing your product sounds simple — just pick a number, right? Wrong! In this episode of ThoughtWave, Chris Leithe and Dr. Aaron Dinin dive into the art and science of pricing strategies that actually work. They unpack everything from psychological tricks that make customers feel good about their purchases to the hidden dangers of pricing models that drive people away.
You’ll hear practical tips on avoiding the dreaded “ick” factor in pricing, why some luxury brands can charge 10x more (and sell better), and what entrepreneurs need to know about packaging their offerings for maximum impact.
If you're an entrepreneur, small business owner, or just curious about the psychology behind pricing decisions, you won’t want to miss this episode!
Listen now on: Apple | Spotify | Online
This week’s new articles…
The Terrible Advice Entrepreneurs Keep Giving Each Other
Being a successful startup founder doesn’t automatically make you great at mentoring other founders.
Strategies for Getting More Investors to “Swipe Right” on Your Startup’s Pitch Deck
For better or worse, fundraising and dating aren’t nearly as different as we’d all like them to be.
Office Hours Q&A
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QUESTION:
Aaron,
I’m running an early-stage startup, and I'm struggling to balance the daily 'do, do, do' with stepping back to think strategically. It feels like there’s always some urgent task demanding immediate attention. How do you handle the tension between constant execution and carving out time for big-picture planning?
Cheers,
Casey
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Startup life is basically one massive to-do list, so I get where you’re coming from. If you’re like most entrepreneurs, you feel like you’re on a hamster wheel that never stops spinning while you’re constantly putting out fires, answering emails, scheduling calls, fixing bugs…the list goes on.
One thing that’s helped me is forcing myself to schedule “big-picture time” just like I schedule a meeting or a phone call. Literally block out an hour or two on your calendar each week (or whatever cadence feels right), and treat it as non-negotiable. No email, no Slack, no phone. Think of it like a mini-offsite — even if you’re in the same office or on your couch at home. During that time, focus on the key strategic questions: Where are we going next? What’s our biggest bottleneck? Do we need to pivot?
You also might want to consider leaning on your team a bit more. After all, they’re the ones living and breathing the product every day as well as talking with the customers, so they’ve got valuable insights. Consider gathering everyone together for a quick “strategic huddle.” I’m not necessarily meaning anything fancy or time-consuming; maybe just 30 minutes of open brainstorming. This not only surfaces big ideas, but it also reminds everyone (myself included) why we’re doing what we do so we’re less likely to get stuck in busywork and forget about the broader mission.
Beyond that, be ruthless with prioritization. Not everything urgent is actually important. When you’re faced with a stack of tasks that all feel pressing, ask yourself: “Which one of these truly moves the needle for our long-term success?” Do those first. Delegating can also help. If certain tasks can be owned capably by others, let them own it. This will free up your headspace for higher-level thinking.
Finally, cut yourself some slack. Early-stage startups thrive on a certain level of chaos, and all entrepreneurs tend to feel like they’re barely keeping up. The fact you’re even thinking about balancing execution with strategy puts you ahead of many founders who never lift their heads from the grind. Consistency is what matters — regularly carve out time for the big picture, share that vision with your team, and the rest will fall into place.
Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer!