May 19, 2024

14 things you better love before becoming an entrepreneur

Imagine somebody asked you to write on a piece of paper the things you love doing. If what came to mind was “partying, hanging out with friends, going to the beach, meeting new people, traveling,” you might ready to go on vacation or spring break.

If on the other hand, you wrote “learning, making decisions, listening, risk, selling, working hard and building something from nothing,” you might be ready to be an entrepreneur. Through my experience I learned about the less glamorous yet truly valuable things entrepreneurs do with their time.

So if you’re thinking about starting your own company from scratch, here are the things you better love – or at least learn to tolerate on a daily basis.

1. Recruiting

Building a team is key to success. Of course, you want to work with rockstars (sans the diva factor) that believe in your vision, are easy to spend long days with, willing to take on risks and work hard for little pay. So does everyone else.

You are competing with other talented startups and, more importantly, with big companies and their large budgets for a scarce resource. This makes recruiting hard.

You’ve heard that investors “bet on teams.” This makes perfect sense since your product or idea might change. One thing you don’t hear as much is that investors look at your team to measure up your ability to sell.

Founders need to sell, and your ability to sell your vision to good cofounders and employees is social proof for the investors. It shows investors that someone else was willing to share the risk with you before you ask them to do so.

Look for teammates as you go and as early as possible. Not only will you increase the odds of finding partners earlier on, you’ll also practice your sales chops and get the realest feedback on your pitch.

2. Fundraising

Ah, fundraising… some CEOs hate it, and some love it. Like everything in life, if you find you are good at it, you are more likely to enjoy it.

Bottom line is, the vast majority of startups raise outside money. Fortunately, you can bootstrap both product and distribution with a lower budget than ever before.

Not everyone can afford to or wants to invest their own money (in addition to their time) into their startup, and many companies need outside funding to scale. Once you are doing well, funding feels less like asking for money and more like choosing it. But you might still need some funding to help you get there.

Luckily, accelerators provide a good platform for kicking off your fundraising efforts and there are more accelerators now than ever before (500 Startups, TechStarsand YCombinator are some of the leaders).

AngelList is also a great platform that you can leverage to drive or track your fundraising efforts. Keep in mind that fundraising will be disruptive to your product development and marketing. Not only because it takes a lot of time but also because while you’re fundraising, you think about your investor leads, intro requests, upcoming meeting and your pitch deck instead of the product, marketing and growth.

The silver lining is that fundraising is a great way to get feedback, meet potential advisors and help distill your pitch.

3. Customer support

You might be thinking “we’ll outsource customer support because as CEO, my time is too precious to help customers figure out how to navigate my site or retrieve their password.” Think again.

The reason you will do customer support is because you will quickly discover how valuable it is for learning from your customers about their needs and about your product.  There is no better way to do that than a real conversation or live chat with someone using your product.

“Talk to your customers” is in startup rulebooks 101 for good reason. There’s so much value in talking to customers and more importantly, listening to them.

The educational value is just one reason you will be doing customer support. Another reason is because you might be the person that will do it with most heart, and we all want to Zappify our brand’s customer experience.

Will you be doing support forever?  Of course not.  Sooner or later you will need to let go and delegate, so you have more time to do more important things. But delegating and managing a job you’ve done is much easier than one you haven’t.

4. Tradeshows

Get ready for fluorescent lights, overpriced hotels, tradeshow food and spending long hours on your feet.

For most industries, tradeshows and conferences are important. They are a place to kick off or develop relationships with industry press, with other companies for partnerships, and depending on the industry, with buyers or vendors. They may even help you spark or maintain friendships.

You don’t want to become a Conference Ho, but you better be ready to hit the floor a couple of times a year. When you look back, you might realize just how valuable those trips were.

5. Working long hours

Thanks to Hollywood, some people think being an entrepreneur is like the movie “The Social Network” where 20 percent of it is work and 80 percent action.

The reality is, you must be prepared to grind five times harder than you ever have while working for someone else. My co-founder and I typically work 80+ hours a week. While we were at 500 Startups surrounded by 27 other companies, we were pleasantly surprised to find this is standard practice in Silicon Valley.

The wonderful thing is if you do something you are passionate about, it doesn’t feel like work, it feels like an opportunity. It’s as if you are on a mission and time just flies.

6. Making tough decisions

When was the last time you had to make an important decision? As a founder, you are constantly hitting crossroads, where it’s on you to decide which road to take.

This happens with product (which features to build and which not), fundraising (if and when and from whom), partnerships, business model types, pricing, which attorney to work with, who to hire and so many more. You must learn to feel comfortable making important decisions.

While you may have good advisors and brain trust around you, it’s on you to make the call and there’s often no clear right or wrong, or at least no way to know until much later. It’s easy to criticize other entrepreneurs or your current boss from the bleachers. But being a founder puts you ‘in the arena’ and that doesn’t happen every day as an employee.

7. Flying

I don’t know anyone who likes to fly. I do know two pilots who love their job. But both confided that they can’t stand flying as passengers either.

Thing is, not everyone will come to you and you’ll need other people’s help, especially when you are starting out. You’ll have to fly to tradeshows or conferences, meet investors, recruit, meet your contract employees, pitch at events and more.

One thing I’ve learned is to optimize for flight comfort (total flight length and takeoff time, for example) rather than for saving $100. You won’t know where that $100 is in three months but your time, alertness in those meetings and resilience to not burn out will make or break you.

8. Being broke

The two primary paths of starting a startup are bootstrapping or raising outside funding. Sometimes the former leads to the latter. When you are bootstrapping you are often living off savings and probably aren’t taking a salary. After you raise outside funds you’ll take a salary but it probably won’t be flashy.

Investors rightfully expect you to be prudent with their money. Either way, you’re unlikely to be ‘living large’ during the first years of your startup.

It’s not uncommon in Silicon Valley for entrepreneurs with millions of dollars in the bank to live a humble lifestyle. So even if you’re thinking of becoming an entrepreneur for the payout (and hopefully you’re not), be prepared to pay your dues.

9. Risk

If there’s one word that defines startups besides ‘growth,’ it’s ‘uncertainty.  You are always at the whims of the market, your users, your runway, investors and your hustle. It’s difficult to plan for the future when you don’t know if the thing that currently consumes your life will be alive in eight months.

Whether you’ll have growth or not next month. If that experiment you’re running with the business model will pay off or bite you in the ass.

Be prepared to develop thick skin and put on those blinders. Your goal is to stay focused on the mountain-top while getting over the hump right in front of you and being prepared for the one hiding behind it.

10. Moving fast

Your most valuable resource as an entrepreneur is time. You are racing against the clock trying not to run out of money, not to be beaten to market by competition, to minimize your opportunity cost and to grow fast.

Since you probably aren’t starting the journey with lots of money, you will wear many hats. This leaves you with very little time.

I’m a musician and have had weeks go by without playing. I’ve seen my friends and family less than I’d like. I’ve watched a handful of movies in the last 12 months, when I used to watch a one or two a week (trailer binging is still allowed though it’s about a fulfilling substitute as donuts are to a good Italian meal).

Get ready to disappear, to go underground. Get ready to lose sleep. You know your friends who recently had kids, and suddenly they are never to be seen and always tired? Yeah, that’s going to be you if you embark on this journey.

Having a startup is like having a baby. But so many parents say, it’s one the most rewarding things they have ever done and would do it again in a heartbeat.

It’s one of the few times in life you’ll go so deep, you’ll get lost in it and return to the real world with a sparkle of wisdom in your eyes.

11. Learning new things

Learning is one of the most rewarding parts of being an entrepreneur. Statistically, most startups don’t succeed. However, what all entrepreneurs ‘win’ at is a huge new basket of experience and skills.

Having to wear many hats – marketing, HR, accounting, pricing, biz dev, pitching, product management and more, forces you to learn a lot in a short amount of time.

Fortunately, there is a ton of info readily available to you. The culture in the startup world today is one of transparency and that’s an amazing advantage.

As pressed as I am for time, I spend a couple of hours every day reading (and the rest of the day doing). You’ll need to be in output mode, but you’ll also get to be in input mode absorbing knowledge, and that’s rewarding.

Founding a startup is like an MBA on speed with more doing and with real stakes.  It’s hard to choose only a few but some of my favorite resources for getting acquainted to ‘Startup thinking’ are:

  • Sam Altman
  • KissMetrics
  • QuickSprout
  • Groove HQ
  • Startup Moon
  • Both sides of the table
  • Paul Graham
  • Moz
  • Steve Blank

12. Selling confidently

If you don’t like selling, maybe business isn’t for you. If you don’t like speaking in front of an audience, you probably shouldn’t become a CEO.

You will need to sell your vision and leadership to your team, sell your product to your users and sell it all to your investors and accelerators. You will likely participate in pitch/demo days in front of an audience. You’ll be asked to do interviews (if you are lucky).

Don’t be a used car salesman, but don’t be too shy or it will get in your way. I always thought that Richard, CEO of Pied Piper from HBO’s “Silicon Valley” would have an uphill battle in the real world.

Even if you don’t have it naturally, being a founder gives you a great opportunity build confidence. Not necessarily through success, but because you’ll learn to find and bring out that confidence from within you very fast in order to stay in the game.

13. Dealing with contracts, legal, accounting

If hearing these words make your eyes roll to the back of your head, you’re not alone. Fortunately it’s easier than ever to get legal documents drafted and do accounting thanks to sites like UpCounsel, WaveAccounting, inDinero and the availability of legal document templates like the 500 Startups’ Kiss investment documents.  There couldn’t be an easier time to do this.

14. Adapting

One of the greatest things being an entrepreneur can do for your character is teach you to adapt – to be open to data and feedback. Being stubborn about your vision regardless of new information you learn can be a hindrance to success. That’s an important part of the Lean Startup methodology that many in the startup world subscribe to.

You don’t want to be a flip flopper, but you do want to be open to adjusting your course. Being nimble is an advantage you have compared to bigger companies.

Big ships take longer to change their course. Learning to be wrong will allow you to find your way as a leader and a person.

At SoundBetter we continually do experiments. We start with a hypothesis about what might work and then make a point of letting the data and customer feedback have a real voice in determining whether we were right or wrong.

As an entrepreneur you are doing the work of a whole company.  In the early days you are running a triage and you will most likely find yourself delving in many of the things on this list. If you are fortunate, you’ll find one or two other people who will go on the journey with you.

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