9 Reasons Being A Startup Founder Doesn’t Suck

We’ve all heard about how being a founder is the worst. Here are nine things I’ve learned that suggest otherwise.

9 Reasons Being A Startup Founder Doesn’t Suck
[Image: Martin Wessely via Unsplash]

Over the last few years I’ve read a number of articles about why being a company founder sucks. While I can empathize, I think we need more public dialogue about why being a founder is worth it, not just long-term but in the moment too.


In our entrepreneur-obsessed times, this state of affairs is ironic. We know plenty about the inspiring skill and vision of our star founders: Zuckerberg, Jobs, Musk, Dorsey, Branson, Bezos. We have intimate knowledge of their financial windfalls. But we don’t seem to know much about the day-to-day of a founder’s life beyond a now well-touted list of challenges. I hope to whittle away a bit at this silence by illuminating some of the more rewarding things about company making.

In 2010 Brian Schechter and I founded HowAboutWe began as an innovative online dating site and has since evolved into a company with a suite of products designed to help people fall–and stay–in love. Our Brooklyn-based company of about 75 people has raised $22 million and is growing more quickly than ever.

Brian and I–best friends since childhood–started HowAboutWe knowing essentially nothing about company building. We learned everything about product development, marketing, and sales on the job. I think this steep learning curve has only amplified and intensified my founding experience–particularly the many wonderful things about this rather peculiar job. Here’s my short list.

Constant Learning And Improvement

The most successful companies are the ones that are most effective at learning. Likewise for founders. Strong founders tend to be great learners. The other day a friend told me an inspiring story about watching Mark Zuckerberg grow as a leader while Facebook exploded; he described a young man who was constantly learning, constantly refining and iterating on his leadership style and studying the effects of the moves he made at the helm. This is in some ways the essence of company making: a crucible of perpetual, high-paced learning and improvement. For the curious-minded–those humans who thrive off attaining and applying knowledge–entrepreneurship is awesome.

Building a Culture Of Growth

A company is one of the most remarkable institutions for human growth. This is, interestingly, one of the least discussed aspects of companies and capitalism. I used to work in public service (education) and there, probably because there was very little money in the work, people talked endlessly about the personal benefits of their jobs. Much less so in business. But working at a company can be–and should be–an incredible growth experience.

In fact, I think one of the most important jobs of the founder is to create a culture in which each of your employees is having a life-enriching, perhaps even life-transforming, experience. This boosts morale, supports creativity, ensures retention, and increases productivity. It’s also better for the world.


You’ll Never Be Bored

Being a founder is not boring. And most founders hate boredom. There are 100 things happening at once. You are constantly shifting from context to context: from design review to strategy planning to recruitment to being on TV to fundraising to managing leaders. You need to be skilled at the big and the small, the human and the technical, the sale and the rigor, the drive and the execution. You won’t sleep much. Your to-do list is absolutely insurmountable. If you find this fun, well, then it’s fun.


The bonds forged with your cofounder(s) and team members in the fires of company making are strong and long-lasting. There’s a togetherness, a pride, and a no-bullshit mutual understanding that makes founder friendships glow. I’ve experienced this most clearly with my cofounder. When things are hard–and the path to success is inevitably hard–mediating challenges with another person can be exponentially more challenging than doing so alone. But if you can communicate well and stay open, if you can be honest and thoughtful, if you can avoid blame–then your relationship will flourish in the founding environment.

A Window

One of my favorite parts of running a company is the view it gives you into what’s happening on Earth. I think this is particularly true for Internet company founders right now, since the Internet is among the most impactful human inventions since, I don’t know, math. This knowledge of what’s happening is a gift. It’s a perspective that carries with it, I believe, a responsibility to stay humble and still figure out how to use your time and resources to genuinely move the lever for humanity.

Overcome Fear

Being a founder is an amazing opportunity to overcome fear–particularly the fear of failure. If you are a founder and are afraid of failing, it will be debilitating. You simply must find a way to overcome this fear. There are many stories that can lie behind the fear of failure: Perhaps you harbor some inner notion that perfection is required to attain worthiness, perhaps familial pressures or concerns about social status drive your fear, perhaps you are attached to material well-being, etc., etc., etc. As a founder, you must come to know what you fear and why. And, ideally, you will come to realize that the fear of failure is both deeply forgivable and always fundamentally delusional. All fear is.

Getting To Know Yourself

Building on my last point, founding a company is an incredible way of getting to know oneself. In my late teens and 20s I was a very serious meditator. Meditation is a profound tool for self-investigation. Starting a company is about as good.

Both activities–meditating and company making–provide you with a radical mirror. In both cases you don’t have to look at yourself. You can float through. But maintaining ignorance almost takes more work than seeing things clearly. Your strengths, your weaknesses–they are staring you in the face all day, every day when you are creating a company. And, if you are willing to look at yourself honestly–with both self-acceptance and also an indefatigable drive to grow–then this is a true boon.


Creating Value And Knowing It

The purpose of a company is to create value. And in modernity that value is determined very simply by whether other companies or humans will buy what you’re making. This simplicity is so honest. The result is that when you are creating something of value you feel that it’s deeply real. There are so few places where value and meaning take on such an indisputable air. I like that. I think founders tend to like that. It’s the feeling: I made this from nothing and I know that other people think it’s worth something.

Founder As Career Path

Today, possibly more than at any time in history, large numbers of high-competency people are genuinely considering founding companies. This is likely a good thing as it fosters innovation, builds social value, and creates new jobs. It’s also a fairly straightforward career choice. Some people decide to become engineers. Some teachers. Some founders. And yet, we know much more about what it’s like to be a teacher than we know about what it’s like to be a founder.

On the one hand, being a founder is a very public experience; we know a lot about founders in the same way we know a lot about celebrities. And yet, on the other hand–in a strange dichotomy–we know very little about founders, these private men and women who create and run our most influential institutions. We haven’t yet quite learned to see the founder as a human.

And we haven’t quite started thinking about the role of founder as a job, like other jobs, with its challenges and its boons. We should, though. Doing so would help existing founders and founders-to-be. And this, in turn, will help our companies, which I–along with many other founders–hope will help people everywhere.