Sahil is the founder and CEO of Gumroad. Gumroad exists to help every creative earn a living selling the stuff they make directly to their audience. Previously, he was an early employee at Pinterest. In his spare time, you can find him thinking and pondering life’s most valuable questions and also a painting which we will talk about at the beginning of the episode. Failure is something that we cannot avoid so, what to do if you fail? I’m here to tell you about that.

This was one of those episodes where I did a ton of research and only asked about half of what I originally wanted to ask. We went down several rabbit holes and it was awesome. Sahil was an incredible guest. He’s really offing smart. He’s self-aware and thinks about the things that matter most to him.

We talk about his most recent claim to fame which is his Medium articles. But we also talk about transparency, getting funding, ego, importance or lack thereof of numbers, wasted time, and sending over 200 million dollars to creators.

Here are,

Some tips to cope with failure!

We all experience to fail once in a while. It’s not something you can avoid. But the experience to fail in life is something that we all need to face in order to earn. But what do we do if we fail? Here are some things you can do to, not fail, but instead, accept it.

Be constructive and learn from this situation

Instead of seeing it as a major setback, think of it as vital input that you can utilize to better.

I’ve discovered that asking myself better questions instead of the typical ones that throw you into a downward spiral is the simplest and most effective method to do so. Instead of becoming caught in denial, negativity, or apathy, the crucial thing is to begin thinking about the problem from this perspective and to be constructive about it.

Make a commitment to being willing to respond to the deeper lessons

This is when being a willing student of life comes in handy. You will repeat your mistakes if you believe you know everything and that life has nothing to teach you. Learning a new perspective on problems could be the key to your next achievement. It’s a humbling experience to learn anything new. You become aware of everything you didn’t know previously. When you notice gaps in your knowledge, take advantage of the opportunity to develop and adapt.

Consider your failure to be constructive feedback. Determine the cause of the failure and whether it was beyond your control. After you’ve gathered all of the information, consider what you can take away from the experience and what modifications you could make to obtain a better outcome next time.

Get support from others

Talking to a close friend or family member might help you cope with the numerous emotions that come with a failure. Receiving assistance will assist you in accepting your failure, gaining perspective, and finding the motivation to try again.

Look for opportunities to learn from people who are already where you want to go. Read books about how business people dealt with failures and how they overcame them. Use their experiences to elicit enthusiasm or motivation to overcome your setback.

Become transparent with yourself

Transparency is essential. When mistakes are made, it is important to forgive people, including oneself. However, you cannot forgive yourself for not being honest with yourself. And as long as you minimize the fault, you won’t be able to totally forgive yourself. This does not imply that you are too critical of yourself, but it does imply that you are truthful. Rather than convincing yourself that your company is collapsing because one boss made terrible judgments, be honest with yourself and consider your involvement in the problem.


Being able to make an appropriate judgment is an important part of ensuring that you don’t get up in a position like this again. A barrier to the truth exists as long as you hold back and rationalize, justify, or minimize your flaws. And there’s that stumbling block.

Move forward

While it’s critical to properly absorb what occurred and gather any essential points, it’s also critical to accept the situation and move on. Acceptance implies that you are aware that you have reached a stumbling block or a temporary setback and that you must now find a solution to the problem.

Sit down and devise a strategy for putting what you’ve learned into practice and moving forward. Recognize that achieving a goal almost always necessitates challenge, progress, and even failure.

Let it out

Another effective strategy to deal with the emotional aftermath and thoughts that follow a failure is to not bottle it all up inside. However, by discussing it with someone close to you, you can bring it into the open.

You can sort things out for yourself, help yourself accept what happened instead of pushing it away, and release that inner pressure by ranting about it while the other person just listens. You can see the subject from a different perspective and through the eyes of someone else by having a talk about it.

This person can assist you in regaining your sense of reality, encouraging you, and possibly even assisting you in finding a path forward.

Find motivation and encouragement

A talk with a close friend or family member might be quite beneficial. Another option is to learn from others who have already gone where you wish to go.

In books, websites, and online forums, find out how they dealt with failures and low periods before or during their achievement. You can also simply tap into someone else’s enthusiasm or energy by listening to a podcast or audiobook for 30-60 minutes. This may or may not be relevant to your current problem, but it can help you adjust your mood and perspective back to positivity.

Take action

The strategy you devise will only be the beginning. You can make course corrections along the route if necessary.

So there’s no need to make it perfect. Attempting to do so can be a way to delay because you are afraid of failing again or because it is difficult to get back on your feet after this traumatic and disorienting experience.

Break down your plan’s initial steps into small chunks, then act on just one of them. If you’re still having trouble getting started, take a modest step forward, say 1-5 minutes. Make it simple for yourself to get started and go ahead again.

Final Thoughts

Those are the things to do if you fail. Now, break down your plan’s initial steps into small chunks, then act on just one of them. If you’re still having trouble getting started, take a modest step forward, say 1-5 minutes. Make it simple for yourself to get started and go ahead again.