Entrepreneurial Mindset: Setting the record straight

Starting a business is exciting, it’s a new venture in something that you’re passionate about and you believe in. However, for every inspiring success story you hear about, there are probably nine other startups that failed. That’s because creating a successful startup is gruelingly hard work. Many of the successful founders aren’t successful on their first try. I’ve had my own share of failures, which gave me the experience that led to Hubstaff.

Launching a failed startup isn't always a mistake. It's an experience. Click To Tweet

There are a few things I learned the hard way after more than 12 years of running and managing a remote startup. You need to cultivate a tough entrepreneurial mindset and unique set of skills to be able to survive launching, leading, and sometimes burying a startup. The job tests my skills everyday, and this post is going to cover a few challenges that I’ve had to face while starting and growing Hubstaff. I go over how the challenges have shaped my entrepreneurial mindset beyond what I expected.

There are no safety nets

Entrepreneurs do not have the luxury of being risk averse. When you are part of someone’s team, you have clear direction, work boundaries and financial security. Typically, employees will have a supervisor and maybe even someone above the supervisor whom they can turn to for advice or help when facing challenges. Someone will always be there to tell an employee what to work on for the most part.

Employees have clear work boundaries and a steady paycheck. In the morning they clock in and at the end of the day, they can clock out and leave stress at work. Every month (or whatever payment timeline the company uses) a reliable paycheck will make its way into employees’ pockets, regardless of what happens with the company revenue or expenses. When you’re an entrepreneur, you don’t have any of that, which means you need to learn to be okay with risk.

With great responsibility comes… Even more responsibility

Founders are in charge of the business, and no one is going to tell them what to do. Click To Tweet

Founders are in charge of the business, and no one is going to tell them what to do. Every moment is crucial for founders, because they are always on the clock but also have to learn to balance work and personal life. A founder doesn’t have a manager or mentor at the company who’s been in the position before or knows what that particular job is like.

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You need to learn quickly or fall on your face

Once you’ve got your startup going and growing, you’ll have to learn on the go even if you know everything there is to know about your product. Once your team expands you’ll have to learn about talent management. When your first customer complaint comes in you’ll need to learn about issue resolution. When the project management software you’ve been using no longer meets all your needs you’ll have to learn about the alternatives and research what’s the best fit for your team. And you’ll need to learn all of this quickly, or face the consequences. Being a founder is so hard because to succeed you need to develop the right entrepreneurial mindset through experience and experimentation. Often, you have to learn on the job.

Founders develop an entrepreneurial mindset through experience and experimentation. Click To Tweet

The entrepreneurial skills every founder needs to develop

  • Drive – As a founder, no one is going to make you go to work at 6 a.m. or even 11 a.m. You have to want your company to succeed and be willing to pour time and effort into it. No one else is pressuring you to make the next move for company growth. Generally, if your focus is money, your business will fail. You need to have the drive and desire for something more.
  • Focus – Many people don’t have the ability to focus on what really matters to the success of a company. They could let distractions interrupt their thought processes, or allow other people to force their schedules upon them. Founders need to be able to create their own schedules around what works for them and allows them to focus on the core company strategy.
  • Decisiveness – It’s hard to tell if a decision was good or bad immediately after making it. Founders need to be able to overcome doubts and hesitations to make a decision, even in the face of uncertainty. Usually only time will tell if what you’re doing is right, so founders often have to learn to be comfortable with that uncertainty.
  • Independence – Founders must be alright being alone. In general, a founder will push harder than anyone else on his or her team, and has to be comfortable putting in the extra work alone. You can’t rely on someone else for success. If you want something, you have to take the initiative and go out and make it happen.
  • Genuineness – You have to genuinely take pride in your craft and your product. When you think about what you and your team built, there should be a sense of accomplishment and a certainty that your product is quality. If you don’t care about what you’re offering others, your customers will soon find out.
  • Flexibility – Entrepreneurs have to be comfortable handling multiple facets of a company. You may have to set up the books, manager sales, contact developers, handle customer support, speak with customers, manage the product and more. In order to be a successful founder, you need a diverse set of skills and the flexibility to play different roles.

  • Product and Market Understanding – A founder needs the ability to understand what the market needs and wants. Then, how to build a product to satisfy that need. You should have skills within the industry or at least a plan to get them.

The entrepreneurial mindset that founders need

The points below are going to have to be your motivators. They need to be what gets you up in the morning, ready and eager to do a good job no matter how you’re feeling.

The best entrepreneurs understand the value of execution. Click To Tweet
  • I must earn my living – If you’re a founder, no one is going to give you money. You have to earn it. You earn it by creating more value for the market than you are asking for in return. Value creation is difficult; it takes creativity and ingenuity.
  • I must plan my success – No one will tell you what to do each day. It’s completely up to you. Some people enjoy this aspect of being a founder and others hate it, but it’s up to you to build a plan and execute on it.
  • I can make good decisions – There are 1,000 decisions that you need to make every day as a founder. this requires flexibility and the ability to constantly shift. What puts even more pressure is the knowledge that the choices you make determine the success of your company, which ultimately determines your success as a founder.
  • I must prioritize my tasks – You need to know what tasks are worthwhile, which ones have high potential, and which ones will be a waste of your time. Learn about how we determine our priorities at Hubstaff here.
  • I must learn from my bad decisions – Most people are not OK with failure. It’s hard not to take failure personally. I’ve had more failures than successes, but my failures often lead to my successes. I fail every single day, multiple times. More than 90 percent of businesses fail for a reason, and it’s hard. But it’s something you have to learn from.
  • I can overcome obstacles – There are going to be problems in any business. You have to be OK with fires and you have to know how to deal with them. Fires do arise, and when they do it’s imperative you get through them and continue building your business.
  • I can make it happen – The best entrepreneurs are doers. They understand the value of execution, and will get things done when they need to be. Strategy and planning is necessary, but execution is where they come together to make something that counts.

Am I doing this right?

You will always wonder about whether you’re doing something right or not.

Every founder at some point, and in my case multiple points daily, has asked the question “am I doing this right?” Is this the best decision I could have made? Should I have worked harder to close that client? Do I have the right set of entrepreneurial skills to make it? Should I have hired that second customer support person? Should I make my product available in a different language?

There is no 100 percent right or wrong way to be a founder Click To Tweet

The fact of the matter is, there is no 100 percent right or wrong way to be a founder and sometimes that’s a pain point because you can never be sure of what you’re doing. I’m constantly asking myself whether I’m “doing it right.” That is the sign of a good entrepreneurial mindset because it means you’ll never stop growing and learning.

The bottom line

I found that being a successful founder comes down to desire and confidence. When you’re a founder, you have the desire to reach the end goal more than anything else in your life. To be successful, you have to have confidence that you are making the right decisions for your company, and then you must execute those decisions.

In the end, despite all the challenges and uncertainty, there’s nothing I’d rather do than be an entrepreneur.

What about you?

What important entrepreneurial mindset did we miss? What challenges do you face as a founder and what skills do you think are valuable for success?

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  • Anton Sekatski

    Thanks for this article Dave, it helped me a lot. I thought I was alone asking this questions and dealing with pressure.

    I honestly think there is a myth came from the mass media which tells us that entrepreneurship is something soooooo easy as pressing a button.

    And when you just start doing it, you find yourself in all this situations when you are flooded with decisions, events and information. At that moment, you literally want to quit… but then, maybe an hour or a day later, something happens inside and you just stay and start making things right.

    Now, I’m starting to understand that it’s a normal process of being an entrepreneur.

    • Yeah, for sure it’s normal. I think I’ve gone through it with every business. The nice thing is that now I expect it. Each business ends up being different though and presenting a little different problems that hit you a different way. It’s very interesting and not meant for everyone for sure.