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8 Reasons Being A Startup Founder Isn’t As Terrible As People Say It Is!

8 Reasons Being A Startup Founder Isn’t As Terrible As People Say It Is!

Over the last few years I’ve read a number of articles — ForbesSF Gate,TechCrunchProduct Hunt Blog — about why being a company founder is awful. Most of these articles cite the relative dearth of public dialogue about the experience of creating and running a company. While I can empathize with this bent, I actually think more glaring is the lack of good content on the (non-financial) boons of being a founder.

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

A bit of background to begin… 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 raised $22 Mn and got acquired by IAC, summer of 2014.

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.

A final introductory comment about the most frequently touted benefit to founding a company: money. If you win, great. But you seldom win. It’s actually a pretty bad financial bet to become a founder. Statistically speaking, financial motivation isn’t a good reason to start a company. If you want to make lots of money, become a banker. People always forget this amidst the media’s obsession with the start-up winners and their wealth.

Ok, that said, here’s my short list of good reasons to become a founder…

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 deeply gratifying.

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.

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.


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. 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

Running a company gives you a specific view into what’s happening on Earth. I think this is particularly true for Internet company founders right now, since the Internet is such a revolutionary fulcrum for world transformation. This knowledge of what’s happening is a gift. It’s also a perspective that carries with it a responsibility and inspiration 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 a damn good way to get to know yourself. In my late teens and 20s I was a 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 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.

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.

Note: The views and opinions expressed are solely those of the author and does not necessarily reflect the views held by Inc42, its creators or employees. Inc42 is not responsible for the accuracy of any of the information supplied by guest bloggers.