Why I’m Not Celebrating a Big Startup Milestone — I’m Using It To Hit a Bigger One

Joe Procopio
4 min readMar 30, 2022


My startup is about to hit a big milestone, and I have a big problem.

As Teaching Startup — my two-year-old project to democratize startup advising by making it actionable and affordable — inched closer to the 100th issue of its answers-and-advice-packed newsletter, it became clearer and clearer to me that this wasn’t cause for celebration.

The problem? Teaching Startup isn’t valuable enough to its member entrepreneurs. Not by my standards.

This isn’t a crisis or a catharsis. This isn’t that kind of post. This is about why I halted a particularly marketable milestone in the lifecycle of my startup to instead push the accelerator on increasing customer value.

So instead of a flashy, self-congratulatory 100th issue SPECIAL EDITION, we’ll be running a targeted, tactical member survey. Instead of members clicking open the newsletter and wondering how we were going to address our own success, I want them thinking about how they can help us make the product better.

Here’s why this kind of thinking matters to you and your startup

Teaching Startup is what I’m calling a meta-startup. It’s a real, profitable business, but it also serves a second life as a real-world example of some of the concepts we address within its own pages.

In other words, it’s ridiculously effective for me to say, “So you know how Teaching Startup does X? Let’s talk about why we do that.” Examples help make answers exponentially clearer.

So while our member entrepreneurs don’t have a front-row seat for how I use those concepts at Spiffy, where I’m head of product, or how I used them back at Automated Insights, where we exited to private equity, they get to watch those concepts play out in real time with the very product they’re using and paying for.

It’s not the secret sauce of Teaching Startup — that’s delivering answers to real questions in a semi-automated form of high-value, low-cost advising. But it makes it more real to be able to see those answers in action.

The first (and only the first) 100 weeks

Teaching Startup has been delivering and archiving answers to real entrepreneur questions for 100 weeks — actually quite a bit more than that because we did a long, real-time beta prior to launch. But this week marks official issue #100.

I don’t celebrate those kinds of milestones externally, and not much internally either. It’s like celebrating a win in the semi-finals. The mission isn’t over yet. And further, I don’t celebrate vanity metrics like number of issues, or even the anniversary of how long we’ve been in business. I celebrate numbers of customers, revenue, and LTV.

Furthermore, the members ( or “customers” — but I hate using that term as it relates to Teaching Startup) and I are in this together, along with the other advisors who (get paid to) spend their time answering questions and the handful of folks who (get paid to — again, this is a real business) help make the infrastructure happen.

We all need to work together to prove that this model can succeed, that we can address this gap in entrepreneurship where traditional startup education is mostly reheated motivation and you either don’t have money so you read someone’s free posts (like this one), or you do have money and can afford the time of someone who has been there and done that — at hundreds of dollars per hour with a lot of small talk and scheduling problems in between.

I need to be relentless about that mission succeeding. And I can’t do it without the members telling me what is working, what isn’t working, what they need, and how to deliver it to them. Then I need to figure out how to make real value economically feasible.

This is the mission of almost every startup

I’m not in this to celebrate 100 issues. I’m going for 1,000 issues. I’m going for lifting the prospects of success for tens of thousands of entrepreneurs. And I’m not talking about 10,000 pitch decks (which is lazy) or 10,000 IPOs (which is crazy).

I’m talking about 10,000 missions accomplished — the life-goal of bringing an idea and a belief to reality. It’s about success, however you define it. So I need to know how you define it. And instead of patting ourselves on the back at 100 issues, I want you to focus on 15 questions we’d really like answers for.

We’ll pat ourselves on the back the following week, because there’s a no-brainer marketing opportunity there. But customer value, that’s what really matters. That’s the point I need to get across.

By the way, you can get in on helping us help you if you join Teaching Startup this week. You get a 15-day free trial and your first paid month for just $5 by joining with invite code MEDIUM.



Joe Procopio

I'm a multi-exit, multi-failure entrepreneur. NLG pioneer. Building TeachingStartup.com & GROWERS. Write at Inc.com and BuiltIn.com. More at joeprocopio.com

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