45 Things nobody tells you about starting a startup

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You’re either really broke or really rich.

Everyone will think you’re broke when you start your business. They’ll view a startup as a struggling side hobby. You’ll always be considered broke and just getting by. When you make one notable achievement, it’s the opposite. On the flip of a dime, people will think you’re rich. People will think your business is a huge success and you’re rolling in the dough. You’re rich, or broke… never in between.

You will never stop working.

You will work in the morning. You will work at night. The weekend will be workdays. And getaways won’t get your mind away from business. Somehow, you’ll always be working or thinking about your business. Customers, investors, and employees won’t refrain from treating you as 24/7 on call.

You will have anxiety.

Every day will bring a new laundry list of tasks waiting to be done. There will be a myriad of problems that need your attention. And you’ll be pushing daily to reach a handful of goals that are just around the corner. All these things create the sad reality of entrepreneurial anxiety that weighs on your mind.

Nobody will tell you your idea sucks.

Everyone will want you to share your idea, but most people will never share their thoughts. They’ll be courteous and tell you how it’s such a great idea. But the people who think you’re crazy won’t say a word. Your closest friends and family will watch you throw away a promising career to start the Uber for picking up dog shit, and never say a word.

You will be misunderstood.

You’ll spend a lot of time answering questions. People will ask why you chose the idea. They’ll ask why you work non-stop. They’ll ask any and everything. And no matter how much you explain, nobody will truly understand what you plan to do, why it matters, and how you plan to do it.

Successes will be short-lived.

There will be small successes here and there. You will enjoy celebrating the 100 customer milestone. But every celebration will be cut short by the realities of growing a business. Some new problem, complaint, or failure will be there to bring you back down to earth.

When you aren’t growing your dying.

You’ll always be anxiously thinking about the growth of your company. When you aren’t growing fast enough you will slowly be dying. It will be a matter of when your business fails not a matter of if. Customers will cancel, clients will switch providers, and revenue will decline. So you will always obsess over growing month over month.

When you aren’t growing you’re irrelevant.

The entire business world only cares about growth. No matter how great your idea, if you aren’t adding hundreds of thousands of users/customers you don’t exist. Journalists won’t cover you. Businesses won’t partner with you. But when you are growing, you’re the next hot thing. So you’ll feel like shit when you can’t grow consistently.

No employee will care as much as you.

You can spend days and days searching for the perfect hire, but they’ll never be perfect. When you find someone with the skills, they’ll never have the passion to follow. They’ll do just enough to get by. And don’t be surprised if a month later they jump ship to the next shiny startup.

You will start talking about business all the time.

People will hate that you can’t turn it off. When it’s time to play and relax, you’ll somehow relate it to business. Your mind will get wrapped up in business just out of habit. Every other conversation will be about new milestones or outlandish customer complaints. Eventually your friends will get sick of hearing about LTV’s and CAC’s.

You will set million dollar ideas on the backburner.

Your entrepreneurial spirit will never die. You’ll have amazing business ideas on a daily basis. And you’ll resent the fact that you can’t start them all. They won’t get the attention they deserve. So you’ll end up giving them away to friends, family, and aspiring entrepreneurs. Or you’ll put million dollar ideas on the backburner, and over the years watch some of them become thriving startups led by other entrepreneurs.

You will feel bad when taking breaks.

You’ll work yourself to the brink of exhaustion trying to sustain growth. Then you’ll need to take a break to recover and refresh. But every minute of every day not being productive will make you feel bad. As you watch other entrepreneurs hustling day in and out, you’ll convince yourself you don’t need any breaks or vacations.

There will be no time for breaks.

No matter how much you want or need a break, you won’t have the time for it. You’ll fall behind on important tasks. Employees and assistants will remind you of the many things they need you for. Whenever you want a break, there will be more going on in your startup than ever before. You will have to fight and claw for the time to take breaks when you really need them.

You’re always one decision away from failure.

At some point you’ll start finding traction. Employees will be happy and productive. Financial projections will have investors and family cheering you on. You’ll be over the moon and optimistic about the future. But then you’ll read articles of one bad PR scandal ruining the best companies. And there will be a dark cloud forever looming over you. It will remind you every day that one bad partnership, one sexual harrasment claim, or one bad product launch can destroy everything you’ve built.

You will obsess over your personal brand.

You’ll wake up one day and notice everyone addresses you as the entrepreneur. Not just a entrepreneur, but the entrepreneur that helps hundreds of kids. Or maybe you’re the owner of an awesome app giving moms more free time. And then you’ll have a personal brand over night. You’ll overthink posting that round of shots at the bar with friends. You’ll spend nights trying to delete every commment from your social media that could even slightly offend moms, kids, or anyone. And you’ll forever be stuck tip-toeing around this personal brand and your true life.

You will obsess over your business brand.

The business will develop a life of its own. Your thoughts and feelings will be second to thoughts of the business. And you’ll find yourself debating with coworkers on, “what would your business do”. You can’t hire the people you like, but only someone that fits your startups brand. You can’t make purchases for anything that doesn’t fit the business brand. And you’ll find yourself tip-toeing around doing anything related to the business brand.

You will feel insecure about your product.

No matter how many compliments you get you’ll think about all the work you need to put into the product. You’ll spend months and years improving it. You’ll take feedback and make every feature your customers ask for. And even after your newest launch, you’ll go to sleep thinking how underpar your product is. Sometimes you’ll wonder why anyone ever paid you for your hackjob of a product.

Angry customers will make you feel like a con artist.

You’ll hear about every email with a negative message. Every customer service rep will forward angry complaints to your inbox. And regardless of how unreasonable or unjustified the complaint or criticism you’ll take it personally. They won’t say it but somehow indirectly they’ll accuse you of flat out robbing them. And somehow you end up feeling like a criminal for the rest of the day.

Happy customers will make you feel like a blessing.

You’ll never hear about the great reviews and feedback. Your customer service reps will always glide over it with a vague summary. But when you happen to glance through emails and read a glowing review from a grateful customer, it’ll hit you. There will be a feeling of joy that someone has been positively impacted. Every bad review will fade away. And you’ll think you’re steve jobs or jeff bezos for a few minutes.

You will never have enough money.

No matter how positive your cashflow becomes you’ll need more margin. No matter how many investment rounds you close, you’ll need to raise more. Even when the money is coming in everyone will tell you how much more successful the startup could be. They’ll say just attend this expo, just try this marketing plan, or just partner with this business. And somehow, no matter how many ideas there are to grow faster, they’ll all require lots of money.

You will lose friends that aren’t productive.

Your hobbies will change drastically. You’ll find yourself only ever doing one of two activities. Working on your business or thinking of what work you need to do for your business. Friends that like to chill, spend money, and gossip will become hard to be around. They’ll want more participation from you and you’ll want to dip off to be productive. Eventually, the friends that never really have productive things to do become acquaintances.

Your family will treat you differently.

Some of your family will think you’re rolling in dough the moment you get funding. They’ll expect you pay for all kind of luxuries they didn’t expect before. Other family members will feel inferior talking to you. They’ll be scared to ask you for help or advice and think they have to be better than you essentially becoming your rival.

Your customers will never be satisfied.

No matter what feature you release there will be another feature people are begging for. No matter how many bugs you fix, they’ll be another bug your customers complain about. And they’ll never think this is the perfect product and exactly what I need. “They’re doing you the favor doing business with you and you’ll forever be in their debt.” Not the other way around.

The thought of quitting will linger in your mind.

Everytime you see a colleague graduate with a degree, get a high-profile job, or travel to a desirable country you’ll think about what your life might have been on the normal path. When things get tough, you’ll question when is the right time to quit. When AI, dropshipping, or on-demand apps get wildly popular you’ll contemplate scratching everything for a more trendy business idea.

Everyone will undervalue your startup.

No matter how many milestones you hit, everyone will judge you based off your numbers and your numbers alone. When you think of the years of sacrifice, investors, family, and customers will only see engagement numbers, user count, and pricing. Nobody will value your startup what you feel it deserves in your heart. Whatever you value it, they’ll cut it in half… twice.

You will laugh at serious things.

When you see how little money you have left in the bank you’ll want to cry. When you see how many users are cancelling every month you’ll want to scream. And when you see how well your competitors are doing you’ll want to rip your hair out. But over time all you be able to do is laugh and keep it moving. Nothing phases you anymore and everything is just a good joke to laugh at.

You will start leisurely spending money.

When you realize that you have no other sources of income you’ll panic. You’ll start charging things on the business card to save costs. Everything you need to survive will suddenly become “meals and entertainment”. And you’ll stop keeping count of how much you’re spending because you’re scared to check your accounts.

Your goals will take 3 times longer than you expect.

You’ll set goals that are completely realistic at the time. But as the year goes on a million things will start to break. You’ll spend all year putting out fires and fixing random problems. And the simple goals that should of been quick and easy will now take years to reach because you’re juggling twelve other things.

Your failures will hurt 3 times more than you expect.

You’ll get one small win in the beginning. People will congratulate you on the success. You’ll get a big head and think you’re invincible. Then when you least expect it life will smack in you down to the floor and humble you. You’ll sit and rethink while you’re down. And everything will hurt three times worst than you expected because you’ll feel like everyone saw you fail.

You’ll become a lot more boring.

When it’s time to have fun you’ll feel like a lost puppy. You won’t know what clubs or parties are the good ones. You won’t know what tv show everyone’s talking about. And you’ll be the only person that doesn’t laugh at memes because you just don’t get them. Your friends will silently label you the workaholic and stop inviting you to events that are supposed to be fun.

You’ll either lose or gain lots of weight.

You’ll spend lots of time on calls, on your laptop, or on your phone handling business. As such, you’ll either be so busy working that you literally forget to eat everyday and start losing bodymass. Or you’ll spend so much time sitting and looking at screens that you snack and stress eat. Two years later you’ll be completely out of shape and overweight.

The smallest things will stress you out.

Your business will put you through a rollercoaster of emotions. One day you’ll be closing a big deal. The next you’ll be losing tons of users or getting cursed out by an angry customer. As such, you’ll be on edge almost all the time. Everytime your phone rings or you get an email notification you’ll get stressed and think the worst of the worst.

You’ll travel more for business than pleasure.

You’ll be on and off planes all around the world meeting investors, recruiting team members, or selling to potential customers. You’ll visit many new places but be stuck in business mode with no time to explore or relax. You’ll start to think of the word “travel” as a business process rather than something people do for leisure.

You’ll start to overthink the value of products you buy.

You’ll pick a price that you feel is fair for the product you sell. Then you’ll get complaints from customers that you’re charging way too much. Other customers will praise you for selling a product thats so cheap and affordable. You’ll probably change your pricing model many times and become more price sensitive. Everytime you go out to buy things as a customer you’ll wonder if you’re getting a good value and what’s the profit margin for the owner of that business.

When business is well, everyone will assume your life is well.

You’ll get used to being treated like an extension of your business. When things are going well with your business with growing numbers you can’t be sad or depressed. And when things are going bad you’ll get random check up texts because everyone assumes you’re sad and depressed.

When you get investment, everyone will think you’re rich.

The moment your investment hits your bank account, people will think you just won the lotto. Everyone will expect you to pay for things and want to become your friend. And if they don’t want to be your friend they’ll want a job. They’ll expect you to drive a nice car and eat at the best restaurants. If you ever act cheap or try to save money they’ll think your business is failing.

You will never get investments when you need it.

You’ll set a specific period of when you’re raising your round of investment. You’ll bust your ass on calls, emails, and meetings nonstop. And no matter how hard you pitch, it will be impossible to get a term sheet. Then when you figure things out and are finally growing organically, investors will start lining up at your door. The term sheets will come flying in back to back.

You’ll always be one decision away from being filthy rich.

After the first few years of growth things will start to fizzle out. The growth will hit a peak and your startup will become stagnant. You’ll fight and claw to get new customers and revenue on a consistent basis. Then out of desperation you’ll start trying and everything you see or hear to keep growing. You’ll be one decision, business partnership, or marketing strategy away from exponential rocketship growth.

Your dating life will become non-existent.

No matter how many dating apps you download, you’ll never get enough dates lined up. And if you do get enough dates lined up, people will stop communicating with you because you flake pretty much every weekend. You’ll have to sit by and watch as all your friends meet interesting people and rub all their love stories in your face.

Your significant other will feel neglected.

You’ll get so caught up with business that you’ll forget important dates and holidays. You’ll feel self-conscious and guilty that you’re not putting enough energy into your relationship. Then your signficant other will start to notice small things like how much you’re on your phone or how late you come to bed. And even if you have been doing good in the relationship, psychologically it becomes a self-fulfilling prophecy.

You’ll get many resumes from underqualified friends.

Regardless of if you have funding or not, friends will look to you as a resource. They’ll want to apply for a job at your company and expect some type of special treatment. If you don’t hire them, it will make things awkward. If you do hire them, it’ll be more awkward when you realize they’re highly unqualified for the job. And you’ll spend hours researching how to reject or fire friends without hurting relationships.

You’ll get no resumes from qualified prospects.

No matter how many job boards you sign up for, you’ll be dealing with highly unqualified leads. You’ll search everywhere from your rolodex to craigslist for just one qualified candidate. Eventually you’ll decide to start trying to steal employees from competitor startups, hiring friends, or just doing everything yourself.

Competitors will rip you off.

You’ll go from being paranoid that everyone wants your ideas to realizing that nobody cares. Then as soon as you start making money with your ideas, competitors will take notice. Everything you do will be copied, duplicated, and iterated on. Many times it will be executed much better than the way you did it originally. And you’ll end up paranoid again about the features and strategies you use.

Everyone always brings up your business.

The first thing people will ask when seeing you is, “How’s business?” It will become more important than your name and what’s going in your life. You’ll get so used to answering the question that you have a preset response on all the great things you’ve accomplished lately. When things are going up in flames, you’ll still tell people about all the great things you’ve accomplished even though it was years ago.

Nobody wants to actually know details of your business.

No matter how genuine people seem, they’ll only ask about your business as a courtesy. The moment you start telling them about KPIs, CACs, and marketing funnels they’ll start zoning out. They’ll silently pity you for always being so business oriented and never having an off switch. You’ll then forever start giving people a basic cliche answer when they strike up conversation about business with you.

These are just a few of the main things people don’t tell you about starting a startup. The only thing I left out is how despite all these things, true entrepreneurs will find ways to keep pushing day after day. The others will likely quit because of one of the reasons above. The question is… which one are you?

Thanks for reading. Comment anything I missed below.

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