5 Tips for New Entrepreneurs That Don’t Just Tell You To Fail First

The hallmark of a successful entrepreneur is being able to transform a misstep into an opportunity.

Written by Slavik Markovich
Published on Sep. 28, 2023
5 Tips for New Entrepreneurs That Don’t Just Tell You To Fail First
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Ask any startup founder for advice and you’ll hear many of the same platitudes: fail fast and break things. Hire people smarter than yourself. Eat your own dog food. Of course, only until you take the plunge and put the work in will you actually begin to figure out your own formula for success.

Every startup founder will make their share of large and small mistakes along the way. But it’s the ones who are able to take an honest look in the mirror and recognize their shortcomings who are most often able to build something of value. Below, I outline my recommendations for what to do when embarking on an entrepreneurial journey.

5 Tips for Starting Out as an Entrepreneur

  • Give your team space for autonomy.
  • Listen to your customers and change course accordingly.
  • Raise more capital than you think you’ll need.
  • Put your ego aside.
  • Keep a healthy work-life balance.

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Let Your Team Decide Their Own Path

One of the most enduring lessons I took from my time in the Israeli Defense Forces is the importance of ensuring everyone on the team understands the primary objective without having to explain the steps needed to achieve it. If a commanding officer tells a soldier to “take that hill,” the officer doesn’t give them instructions on how to do it, but expects the soldier to accomplish the mission somehow, some way. 

In business, this same mindset, which encourages individual team members to take initiative and responsibility for their actions, helps build a broader culture of empowerment. Giving team members a clear goal, but the freedom to define how they achieve the goal for themselves, provides an opportunity for real growth and development. 


Be Flexible to Change

Following the exit of my first company, it didn’t take too long for my co-founders and me to begin working on our next idea for a startup. After spending months building a working prototype that we believed solved a real problem, we confidently went to a big trade show to demo it to a number of industry security executives, only to be surprised and disappointed to see the executives’ lack of interest. 

But, instead of closing up shop, we went back to the drawing board. We quickly realized that you can’t build a great product in a vacuum; you need to listen to customers to ensure you’re solving real problems and bringing value.

So, we followed up with the executives we met with at the trade show and asked for time to observe their security operations. Once we better understood the issues they faced, we were able to pivot and create a new product our customers would actually buy. 


Raise More Than You Think You’ll Need

I first moved to the U.S. in 2008 right as the financial crisis was unfolding. Suddenly, raising money from the venture capital community became very challenging. Given the uncertain economic environment, funding rounds were down, customers were conserving cash and we were left with no choice but to lay off a third of our workforce. This was one of the lowest moments in my career, knowing that people who relied on me for a paycheck would be suddenly out of work. 

Raising early rounds of capital can be frustrating and requires an enormous investment of time and energy — time that you could be spending talking to customers and building your product. That’s why I recommend raising more than you think you’ll need in these critical early stages in order to account for the market uncertainties that are impossible to predict. Even the best laid plans go awry, so the more capital you can raise in the early stages, the more likely you’ll be able to live to fight another day. 


Listen to Your Team with Humility

My current startup includes myself and seven other very smart and opinionated co-founders, many of whom I’ve worked with for over two decades. As you might imagine, having eight strong personalities leading a young company comes with its own challenges. 

I’ve learned that the best teams cover each others’ blind spots. Every entrepreneur must have confidence in their strategy and vision, but they also need to have the ability to recognize where their talent is best served and where someone else should step in. The ability to let go of your ego is hard, but necessary, to create a culture where even the quietest voices get heard. 

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Take Time For Yourself

Every entrepreneur understands that building a successful venture requires an inordinate amount of grit and determination. Like so many other founders, I was burning the proverbial candle from both ends growing my first startup and didn’t make enough time for my family and hobbies. 

While this might be necessary at times, be mindful of the consequences of ignoring a healthy life-work balance. Not only will working non-stop take a toll on your physical and mental well-being, it will likely impact your creativity and productivity in the long run.


What’s the Hallmark of a Successful Entrepreneur?

As anyone who has started up a new venture knows, there is no roadmap. But there are guideposts that can help you along the way. It’s important to remember that whatever stage you might find yourself in your journey, you will make mistakes. The ability to transform those missteps into opportunities is the hallmark of every successful entrepreneur.

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