What It’s (Actually) Like To Be an Entrepreneur

It’s never been easier to become an entrepreneur and start your own company — and for many people, it’s never been more necessary. There’s no mistaking the ways the COVID-19 pandemic has upended people’s lives, and the industries they work in — and if you’re one of the millions of unemployed people in America, you’re probably looking for ways to make money that isn’t reliant on a boss or a major corporation. What if you were the boss? And, could you scale a company properly, even in one of the worst recessions in modern history?

Before I founded my own company, I cut my teeth at a major ad agency. I learned how to be an adult there: How to work a job, how to send an email, how to make an argument in a tight way, that kind of thing. And while I learned a bit about how big advertising works, I also learned how it doesn't work. I had a lot of instincts — even as a very young person — about how the way things “are done” didn’t feel right to me, or make a lot of sense. I had this private theory that the industry is going to collapse… and I was right. Thanks to the internet, social media, COVID, and more, agencies of old are just crumbling into the ocean and creating room for the entrepreneur era to take even firmer hold.

I founded The Hub in 2015, after a period of intense struggle at my job creating content for a doomed startup. I'm not religious nor am I a guy who believes the universe has a way of telling me things, but I've had a few moments in my life that feel almost like there was divine intervention or like a lightning bolt just struck: The Hub was one of those moments — but that doesn’t erase the amount of work, sweat, and tears I’ve put into the company over the years. Throughout, my macro instincts about how to build a company were dead on, but thousands and thousands of smaller instincts and decisions and thoughts were completely wrong — and continue to be. It’s all about recalibrating as you go, and about sharing your knowledge about what you’ve learned along the way so that other people can benefit, too.

1: Find Inspiration in Your Frustrations

One of the biggest lessons I learned while working for other people is that no one knows what they're doing. I saw this happen in real time through the company I worked at after I left the ad agency, which was once valued at $40 million and ultimately sold for $5 million two years later.

While I was there, no one I reported to had any time to worry about what I was working on — they simply had way bigger problems. At first that was really scary because I had always had structure, whether that was at Princeton University, where I went to college, or at an agency where my boss had a boss who had a boss and so on. All of a sudden, there was basically no one to tell me what to do or what not to do, and I had a couple of sleepless nights about that. 

I knew that I had things to accomplish. I had no idea how to accomplish them. I had no leadership, the company was burning. It was very stressful, and I considered quitting. But I also, for the first time, felt immense ownership of my goals, so I stuck it out.

Everything came to a head when I was sent down to a filming project on location, which was a disaster. I stayed up all night figuring out how to fix it, and it was really vindicating that I solved the problem. While my bosses didn’t really care, it was a big moment for me to realize that I can look fear in the face, and from that moment on, I started running towards the fire instead of running away from it. 

The entrepreneur in me was sort of awakened in that moment. It had always been there — I always had schemes and projects, even when I was a little kid. But I think that person was made dormant through the years, and was only awakened when everything around me was on fire. So when the idea for The Hub, a marketplace and meeting place for creators and brands alike, came to me, everything made sense and  I knew I had to run toward it.

2: Make the Most of Every Dollar

When I started The Hub, I did so with a $20,000 investment, which included $4,000 of my own money, and a $16,000 loan my dad had given me when the company I worked for decided to default on paying its content creators, many of whom were very young. That didn’t sit right with me, so I asked my dad to lend me the money — and then when it came time for me to quit, after two months of working for free, I asked him to be my seed investor.

At the time, there were only a few of us building our community, and being really scrappy because we had to be. We were just wide-eyed and excited about what we were doing. We believed in something. I paid three creators $250 a week out of that initial $20,000, and we had hundreds of meetups and events and gallery shows with some of social media’s first influencers. We made that $20,000 last about six months, during which time we grew our Instagram to over 100,000 followers and grew an email list of over 6,000 people that became the first members of the hub as it exists today. We built a very loyal base of followers, many of whom are still photographers on our platform today. We laid the groundwork not only for a customer base, but for a community.

But even though we had limited funds, we never compromised on quality. We see it in every industry, from food to fast fashion: there's this trend towards mass producing and a highly-processed product. The same thing has happened with content and influencers. But in the very early days, I stressed the need to build a moat around quality, around community, around things that I knew would be rarer and rarer commodities. 

Especially if you’re starting a company in a recession, be doubly cautious with every dollar you spend, and consider launching in a smaller, more modest way. Use this time as an impetus to build a company as tightly and modestly as you possibly can. When the market starts improving, the sea will be rising with you. With all your discipline and knowledge and understanding of how the world and entrepreneurship works, you'll be doubly successful.

If you don't have $1,000 in the bank, you probably can't start a company right now. But if you have that or more, you definitely can. It’s never been easier to lay the foundation, and there are plenty of ways to beta-test your product without investing any money at all. Can you use a Google Sheet instead of sinking money into an app you’ll have to redesign over and over again? Maybe don’t go to a software platform, or build a website off the bat. Get your idea out into the world in the cheapest, simplest way, and aim to spend less than a hundred dollars a week. In that era of discovery, you'll either decide you're not an entrepreneur and you'll quit, or you'll use that stress as fuel to keep yourself going.

3: Your Team Is Everything

A lot of people think entrepreneurship is a very lonely grind, but the simple truth is, it doesn’t have to be that way.

I said in a talk recently that if you don't give away 60% of your company as a founder, you're doing it wrong. You never want your company to be informed by an n of one, so if you start a company with someone, you each have 50 ownership. Your first employees, or an investor or advisor that you really respect might get three, four, five, six percent each.

In my case, I used money out of insecurity, rather than defensiveness. I didn’t want other people to have to take on risk. People who believe in you and what you’re building will be willing to work for cheap or free, but I’ve always paid market rate or over because I know that it's scary to join a fragile company. I’ve only fixed my own methodology in the last six months, and I chalk that up to slowly trusting people, and slowly letting them in. 

Now, my team is very close and we would bleed for each other, because we know what it takes to make our company work. And I have learned in real time that etting people carry the load for you actually isn't an inconvenience for them, but gives them purpose and meaning too. 

4: Say “No” to Things

Napoleon very famously wouldn't open his mail for two weeks, because he believed most of the things in those letters would work themselves out. If, after those two weeks, he opened his mail and something was still relevant, then he would act, but 80 percent of the things were actually irrelevant at that point. Imagine if we did that to the emails and text notifications piling up in our inboxes every day. How much more time would we have to just get down to work?

There are so many things you can do as an entrepreneur — I know, because I did them all and sprayed energy around. But if I just said “no” to most things and been very focused, that would have served me much better. 

5: Start Small, and Stay Humble

If you can delay instant gratification and not worry what other people think, start really, really small because your mistakes aren't magnified. If you start really big and you do really big, aggressive things, you’ll be way off when you’re wrong. And you will be wrong. 

Don't be so insecure that you have to hit the ball as hard as you can, right out of the gate has almost assuredly you'll end up in the bushes. Because, look: The hole-in-ones don’t happen. We hear stories about Facebook or Airbnb, but it's never as easy as it seems. It's never like someone just woke up successful one day. There was always a lot of hard work underneath that.

Entrepreneurs get spun by their ideas all the time: You start out cocky, and you’re like, “I have a great idea, everyone thinks it’s a great idea, and I've made 20 sales.” But something will always happen, and you have to be prepared to handle that setback. If you go in with an appropriate respect for the craft of entrepreneurship, you'll be more ready when you get hit.

I know firsthand that you need a combination of opposing forces to make it as an entrepreneur: A deep belief or passion for your idea, and a deep humility for when you get told no. If you're too cocky, you'll fail because when you get negative feedback, you don't deal with it well, but if you're too weak and too receptive to the feedback, you'll just get pounded into the ground. The hardest thing about entrepreneurship is walking that tightrope between deeply believing and also being humble enough that when you're wrong, you can admit it without any insecurity and learn from it. Finding that balance helps you be less afraid to fail. 

6: You Will Never Stop Working Really Hard

Entrepreneurship is life, and it’s the longest of journeys. You can’t hack the work, and you have to remember that what you do behind closed doors speaks volumes as to who you truly are. There are glamorous moments as an entrepreneur for sure, but those moments often belie the reality, which is showing up every day and working really hard.

I've had probably 20 or 30 moments where I was like, “This is it. This is the moment where we go from cruising along to the big time. This is the moment where it gets easy.” It's never gotten easy. Every day has been challenging, and every day has been showing up and chopping wood. 

All of that hard work separates the people with ideas from entrepreneurs. There are people that never work hard at all and they would lose right away as an entrepreneur, while others might fake it or work hard for the momentary optics. They fail, too. The only people that succeed are the people that quietly and humbly show up. They don’t let losses or setbacks stop them. They push through their disappointments and consistently show up again. They know that anything worth building takes time. 

As an entrepreneur, you constantly have to calibrate. You have to learn what it feels like to trust yourself. You have to take feedback, and trust other people. And learning how to do all of these things can be really hard. I’m constantly working at it still.

Everything that I’ve learned, I wish I could go back and tell myself, but paradoxically it's through failure that I’ve learned some of the most valuable lessons. If you get burned a couple of times, you've also learned real lessons from really being in the trenches. Part of me wants to go back and tell my old self all the things to avoid. But part of me is happy that I didn't avoid those things, because it made me so much better and smarter and stronger now as an entrepreneur — and as a person.