The Dirtiest Job You'll Ever Love: Why Chaos Builds Success

Forbes

16-07-2025

The best entrepreneurs embrace the chaos.
Most professionals try to avoid career chaos. What could be more natural than trying to stay as far as possible from uncertainty, rejection and failure?
Unless, of course, you want to build a company. Those negative waypoints are exactly the things entrepreneurs learn to love.
There are good reasons any leader should learn to embrace discomfort, entrepreneur-style, even if you're leading within an established organization. After all, every career journey crosses some rough patches, particularly in an economy undergoing the kinds of upheavals that are everywhere these days.
Here are 6 counter-intuitive principles that all successful founders follow, consciously or not. They can help you through any messy career passage.
Love the journey
Founders know they won't have the wherewithal to withstand the blows of entrepreneurship if they don't love what they're doing. The blows are inevitable. What matters is how you respond.
Kass and Mike Lazerow - the husband and wife duo who built Buddy Media and then sold it to Salesforce for $750M - have written a book dedicated to that. Their book, Shoveling $hit: A Love Story About The Entrepreneur's Messy Path To Success, outlines 50 lessons they learned through their company's many hair-raising ups and downs.
Gary Vaynerchuk, serial entrepreneur, agrees that you need to love the journey for its own sake. 'If you don't like it, it won't work. If you're doing a business for the money it's the number one strategy that makes people fail. It's not a hokey thing to say you have to enjoy the journey.'
Love losing
Part of the journey includes failure, mistakes, and just downright dirty work.
'One of my favorite things about entrepreneurship is when I lose,' Vaynerchuk said. 'Because I think it allows me to not get as the amazing poet once said, high on my own supply.'
You also have to love figuring out what won't work and be able to drop it.
As Mike Lazerow puts it: 'We love throwing things away. We love the pivot.'
When you're willing to see past work and ideas as just that–past–and not as something that needs to be justified, you allow yourself to see what will work in the future. You can focus then on that, without being anchored to the past.
Love the competition
Jim McKelvey, cofounder of Square, credits an aggressive move from Amazon in part for the success of the company.
When Square was a young vulnerable startup, Amazon announced a competitive product. It was 30 percent cheaper and had all of Amazon's power behind it.
'We didn't have their scale or their servers or their talent or their brand name,' he said. 'We don't have a listening device in everybody's home. We just don't compete very well head to head with Amazon especially when they're undercutting our price.'
What did the team do? Nothing. 'We aggressively did nothing against Amazon,' he said. 'The miracle is that our strategy (of doing nothing) was successful.
Amazon ultimately got out of the market and when they did so they mailed a Square reader to all of their customers.
'We got market validation and all of their customers,' he said.
Sometimes waiting out a huge competitor that doesn't have your passion is the best strategy to help mature a new market.
Love fundraising
Plenty of founders are visionaries first and foremost. They enjoy the process of thinking about what they want to build and working with their teams on the product.
But that's not enough. You have to love to pitch.
As an entrepreneur, you're selling all the time. You're selling to customers, of course. You're also selling to employees and to investors to get them to invest their money in you and your idea.
Liz Zalman, multiple time founder and co-author of Founder vs Investor taught this to herself.
'I used to hate fundraising,' she said. 'But since then I've figured out it's essentially a sale. I am selling a vision to somebody who has capital and I want their money. And so the question is simple: what are the things that I need to say in a particular order in order to get them to agree to give me that money?'
Rahul Vohra, cofounder of Superhuman (acquired by Grammarly) has also learned to embrace the process of pitching. In fact, when he's down, he pitches himself. 'It's very easy to lose sight of a ginormous opportunity because you're just dealing with the day-to-day,' he said. 'One trick that I would highly recommend to all founders is to go back to your last fundraising deck and literally pitch yourself. Read through it and you'll be like, oh yeah, yeah, this rocks, we are going to be a huge company.'
Love the mission
You go through tremendous mood swings as a founder, sometimes in the span of an hour. You win a major customer and get a big rush. Then a key employee quits, and you wonder if that will start a stampede out the door.
The emotional ups and downs are challenging, so you have to hold onto your north star. You have to remind yourself of your mission.
Gusto cofounders Joshua Reeves and Eddie Kim talked about the reason they started Gusto, which helps small and medium businesses get HR benefits.
'Both of our families worked at small businesses and we really believed there was an opportunity to make that experience so much easier and simpler,' Reeves said. 'We saw how many owners were in pain or frustrated. That's actually what got us most excited.'
Love the pattern more than the idea
Knowing if you have an idea that can go all the way is learned through experience. You have to learn from your mistakes and use your hard-won insights to see patterns.
Kass and Mike Lazerow created the 'Go Gauge" as a framework for you to be able to see if your startup has legs.
The Go Gauge is:
Before you fall in love with your idea, you can run it through the go gauge to see if you can build a business out of it. Even if you have checked all these boxes, success is not guaranteed. The only thing that's guaranteed is that there will be plenty of dirty work along the way. The advice of these successful founders is: Make sure you will love it.