Entrepreneur Office Hours: Issue #206

Cleaning up all my the messes of a "fail fast" entrepreneurship

You may have noticed some slight changes around here over the past few weeks. Most obviously, the color scheme flipped from a pink-ish orange to a blue. That’s all part of an attempt to take what’s been a labor of love for the past few years and make it bit more organized.

Simply put, I posted my first article on Medium four years ago this month. When I began, I never expected things to get this far. Now I’m looking back at the haphazard way I’ve built things — including 400+ articles and 200+ newsletters about entrepreneurship with millions of views on them — and I’m realizing maybe I need some better organization. In a way, I suppose I’m living my core entrepreneurial, “fail-fast” values… get something ugly and dirty into the world as quickly as possible, figure out if people want it, and then go back and polish the thing once it’s been proven valuable.

That polishing begins with a new AaronDinin.com website. I just launched it, and I’m still too much of a code nerd to let anyone else build websites for me, so I coded it myself. In other words, I’m sure it has lots of bugs, and I could use the help of a few thousand friends to make sure it’s working properly, so, when you have a moment, would you mind taking a look and letting me know if you notice anything broken (including the forms)?

I’m also going to work on improving this newsletter. Since the inception of Entrepreneur Office Hours, I’ve mostly just been linking to the articles I’ve published elsewhere and answering reader questions. But maybe I can do more? Don’t be surprised to see me experiment with some new things in here as I try to figure out what could be valuable, and, as always, your feedback is appreciated.

Lastly, I’m going to work on organizing my article archives. As I mentioned above, I’ve published hundreds of articles about entrepreneurship, and while they’re not all gems, some have good info in them, and I need to make them more accessible, especially to new readers, so I’m going to figure out a way to do that, too.

What does all this mean for you? Nothing particularly actionable, I suppose. I mostly just want to thank all of you for your incredible support over the last four years. Thanks for reading, thanks for sharing, thanks for your comments and feedback and ideas and support and everything else. I’ve spent lots of years building lots of companies, but building this community has been, by far, the most rewarding work of all, and that’s thanks to all of you.

I’m grateful…

-Aaron

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Office Hours Q&A

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QUESTION:

Dear Dr. Aaron,

I am working on a startup idea for an online tutoring marketplace connecting students with tutors. But I am confused how to validate properly whether students and tutors will use this platform and want to do as such before building the full website and app.

I am wondering what creative suggestions you would have for testing the viability of this marketplace concept in a cost effective manner? What validation experiments have you tried when first starting similar ventures?

I eagerly await your insights. They will be greatly helpful for this first-time founder.

Sincerely yours,

Ravi

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I’m glad you’re thinking about testing and market validation before building the app itself. Far too many founders focus on building a complex platform on Day #1 before proving basic viability. The fact that you already understand and appreciate the importance of doing validation work tells me you’re a mature first-time founder.

As for how I’d suggest testing a project like you’ve described, the big issue here for me isn’t whether or not the idea is viable. Students have needed tutoring help for who-knows-how-many years. Plus, new students are being created every day, so it’s not like the market is going to dry up anytime soon.

With this in mind, if I’m considering a startup like you’re describing, the big question I’d want to answer for myself is whether I can find a scalable, replicable way of getting users. And, really, the question isn’t whether or not you can get tutors. If you have a huge marketplace of students looking for tutors, you’ll be able to get tutors. The issue is whether or not you can get students. How are you going to prove that?

Honestly, I don’t know. I can certainly give you answers that seem smart or thoughtful and will make you feel good, but they won’t necessarily be genuinely helpful in solving the main problem you have.

For example, I took your question and asked it to ChatGPT. Its response focused on manually creating a few tutoring matches to prove the model, suggesting:

• Recruit 5-10 tutors in a particular academic subject by reaching out to top performing students.

• Recruit 20 students needing tutoring help in that same subject through local outreach.

• Manually pair each student with an appropriate tutor based on availability, subject, level, etc.

• Introduce the matches over email and have them schedule sessions on their own.

• Observe if they are able to successfully self-coordinate and complete the tutorial sessions.

• Interview both sides afterwards to understand pain points in the process.

That answer sounds good, but it’s lame. It’s also the kind of answer you’re going to get from most “startup experts.”  For me, the above process only proves that people want tutors, but we already know that. It doesn’t help you prove you could get students onto a tutoring platform at scale, which is a much harder problem.

I suppose if I’m in your position I’d take some sort of “influencer” approach. I’d try to personally build an audience using social media giving tips/tricks/advice/hacks for students. Once I figured out how to capture a student-centric audience, I’d promote some other tutor and e-learning brands to them (possibly using an affiliate program to make some extra $$$) and see if I can push that audience to some sort of online learning program. Alternatively, I might attempt to create some social media ads that push people to an e-learning program.

Either way, my goal would be to prove I can access students at scale and push them toward purchasing some sort of related tool. If I could do that, I’d have the validation I need to justify building my own platform. If I couldn’t… it would be back to the proverbial drawing board.

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