Dear founder,
Let’s dive into a piece of entrepreneurial advice that’s highly irritating and very dangerous. Today I want to talk about the one that I get so much: “Don’t give up. Don’t ever give up. Force yourself, grind it out.”
This advice is very dangerous because it builds on the founder’s capacity to struggle through challenges, but it uses this for the very wrong reasons.
And before we get to that, a word from our Sponsor, Paddle.com. Im using Paddle as my Merchant of Record for all my software projects. They take care of all the taxes, the currencies, tracking declined transactions and updated credit cards so that I can focus on dealing with my competitors (and not banks and financial regulators). If you think you’d rather just build your product, check out Paddle.com as your payment provider.
The Hidden Danger of Persistence
Here’s what makes this particularly dangerous: “Don’t give up” is really, really useful advice—until a certain point. After that, it becomes extremely dangerous. And the problem is that, as a founder, you do not know where that point is. You only ever know where that point was in retrospect, and even then, things are complex. Things are highly codependent, interdependent. So you don’t even know what caused that point to appear in your journey.
It takes a couple years after you stop a business, sell a business, or grow a business and become successful—it takes a long while for you to figure out why things happened the way they did. Because a lot of the reasons for success or failure are not even intrinsic to your project. They’re mostly part of the market, or part of technological advancement, or the actions of competitors—or the inaction of your competitors. There are so many reasons why things work or don’t work, or things shift and make things possible or impossible, that you will never really know in the moment.
When “Don’t Give Up” Actually Works
“Don’t give up” is a good motivational thing to use when you struggle with the initial pains of establishing an understanding of your market. You don’t know much, and it takes a while for you to learn all the nuance of it. So when you don’t really see what you want to see for the first couple weeks or months, that’s fine. Some things just take a long time.
Particularly as you’re building a software business with more enterprise, the bigger clients—certain things just take a while. I’ve had lots of clients or customers in the pipeline for PodScan that I reached out to, they did a trial, nothing happened for a couple months, maybe even years, and then they subscribed because they operate on their own timelines.
The Timeline Problem
The thing is, so do you. And you not giving up on a timeline that does not have millions of dollars of budget behind it to slow things down—that is actually quite dangerous. It becomes detrimental to your business to be stubborn when it means that you’re running out of money, or that you are trying to force a particular approach into a market for too long, when you should just be experimenting more.
The Real Solution: Experimental Persistence
And I think this is the solution to this advice that makes it actually usable: Don’t give up, but do different things—and maybe opposing things—at the same time.
If you are trying to make money in a particular market, and you just struggle and there are not enough customers, or retention is horrible and people quit, two things could happen:
- Things could just change for your customers, so that their retention all of a sudden increases, and they stop churning, and they find value in your product. That’s kind of the hopeful, wishful thinking “don’t give up.”
- Or you could make changes. You could change your positioning, you could change your features and your product, or your approach to educating your customers so that they then can develop this newfound appreciation of your business.
And you never know which one of these will be the successful one until you try both at the same time.
The Power of Parallel Experiments
Constant experimentation at the same time, while still only running a limited number of experiments, is the antidote to pointless “don’t give up.” If you see no changes in one of the approaches and some changes in the other, then you know that you’re dealing with a particular problem. But if you see changes in both—if you run experiments with some customers, present a new interface and a new approach to business to some and the same old stuff to the others, and both of them increase retention or decrease churn or subscribe all of a sudden—then it had nothing to do with your product. It had everything to do with the situation of your customers.
Think about changes in regulations in the market that were not to be anticipated, or new competitors joining a market, or some competitors dropping out of a market. All of a sudden, everybody who was a client of theirs is looking for a solution that looks a lot like theirs, and now you’re able to provide it. But until that competitor moved upmarket or changed their pricing or something, there was no reason for anybody to move over to your product. And those are things that you need to constantly look at.
Giving Up the Right Things
Giving up, generally, does not mean to give up the whole thing. You might just give up an assumption. And maybe that’s the thing. Maybe giving up is not about giving up doing the business, giving up entrepreneurship, but it’s giving up your long-held assumptions—the things that you thought were true, because they’re not necessarily true. They’re just true in your mind because of the experience you have. But your experience is limited to your own life. Only you know about you. Only you have ever had your own experiences. Other people have not, and they might not see the world the same way as you do.
The Landing Page Revelation
I remember a Twitter conversation with somebody who was talking about Pieter Levels and his—well, let’s call them not extremely modern—landing pages for his products. And that person was saying, “I cannot believe somebody with landing pages that look this old, that are not modern at all, is making this crazy amount of money a month.”
Some of the replies were like, “Yeah, you just don’t understand landing pages.” But one of the replies that I really enjoyed, and then kind of chimed in on, was: “Yeah, and you already started wondering about why that is the case. Now maybe you should just ask yourself why you think that a beautiful landing page actually makes more money—because it doesn’t, as proven by this example.”
The Final Truth
So there’s the assumption that you may have, or might have had for a long while, that might just be wrong.
Give up the assumptions and try others. Run a control group to see if the assumption might have actually held true. Don’t give up the business, but give up your assumptions.
That’s the real lesson here: persistence isn’t about blindly pushing forward with the same approach. It’s about persistently experimenting, persistently questioning your assumptions, and persistently adapting based on what you learn. The founders who succeed aren’t the ones who never give up—they’re the ones who know what to give up and when.
So the next time someone tells you “don’t give up,” remember: they’re half right. Don’t give up on your business. But absolutely give up on the assumptions that are holding you back from finding what actually works.
We're the podcast database with the best and most real-time API out there. Check out podscan.fm — and tell your friends!
Thank you for reading this week’s essay edition of The Bootstrapped Founder. Did you enjoy it? If so, please spread the word and share this issue on Twitter.
If you want to reach tens of thousands of creators, makers, and dreamers, you can apply to sponsor an episode of this newsletter. Or just reply to this email!
