Lose Battles, Not Wars

"Never give up" is flawed advice

Every founder thinks what they’re working on is their life’s work. In 2015, my life’s work was helping people network better at events. In 2017, It was helping startups get better at content marketing. In 2019, it was helping writers liberate themselves from content mills. And today, it’s helping outsiders get the bag💰. This is hypocritical though, right? How can someone have four of these in the span of a decade? It’s because we don’t want to live in a world where what we’re working on now doesn’t succeed.

With this mindset, founders go to great lengths to up their chances and stay in business, even when things are going quite poorly. I think this is where the common advice of “never give up” gets popularized”. No cash in the bank? Never give up! All your team quit at once? Never give up! Spending 14 hours a day working to make rent? Never give up! When the going gets tough, the good ole “never give up” should do the trick, right?

Maybe, but there’s the factor that never gets talked about…People who give the advice “never give up” don’t need to experience the repercussions of living through their advice. “Never give up” is easy to say, hard to do, and almost impossible to execute on once it needs to be said. It makes the person saying it feel good, yet it likely makes the founder that should have given up long ago feel even more conflicted. Because founders are fighters, we always think they can make it through the dark days. We’re optimists after all, and we’re working on our life’s work, right? Yet after three failed companies myself, each one a larger scale failure than the last, I have reformed my opinion here. Instead of “never give up”, my advice is now "Lose Battles, Not Wars”.

For me, the war is working on something that matters to me and to the world. From 8th grade when I put up the first video of me singing on Youtube, I decided I wasn't going to succumb to a life that sucks my soul. I was going to break free and make something of myself that I was proud of. Something that would transcend well beyond me and my family, and well after I die. This is the war I am fighting. The battles are each company I start. Every company I start is an effort to win the war.

When a company I founded fails, I get a job, spend a lot of time strategizing, plan my next attack, and go to battle once again as a smarter and more experienced general. The chances of me winning the war are greater because I am willing to throw up the white flag in battles I have no chance of winning. And let me tell you, as someone who’s been around the block, my passion for solving the funding problem burns just as strong as my passion for solving the networking problem in 2015. The problem isn’t what makes the founder. The founder is what makes the problem.

If you’re reading this and you’re on the brink of giving up, yes I could tell you to keep on going until you succeed, but I worry that if I did that, you would do damage so deep that you would lose the war altogether. So, my friend, I am giving you permission to give up. Wave the white flag. Lose the battle. Because only at that moment can you prepare for the next one.