Successful Startup

While news headlines focus on the glamorous success stories of startups, it’s important to understand the real journey of the most successful companies. With 90% of startups failing before making an impact, knowing how to navigate the highs and lows of the messy middle is crucial. While many guides focus on starting or ending a venture, it’s the ability to withstand the ups and downs that ultimately determines success.


Launching a new venture, whether it be entrepreneurial or artistic, is like embarking on a challenging journey. While starting out, you may share similar hopes and fears with others attempting to create something new. However, regardless of what you are trying to accomplish, you will inevitably encounter the messy middle.


The messy middle of any worthwhile endeavor is highly unpredictable and can feel like a rollercoaster ride of highs and lows. After the initial honeymoon phase, during which you are blissfully unaware of how much you don’t know, you will likely feel lost. This middle section is all about making progress, finding direction, and then stumbling and losing your way again. Your goal is to endure the lows, relish the highs, and continue to push forward to ensure each low is not as low as the one before it and each high is higher.


Although the mid-section may appear to be all downhills and uphills when you’re in the thick of it, over time, you will hopefully see an upward-slanted median leading to successful completion. This is what the journey to accomplishment looks like.


Consider the example of Scott Belsky, who founded Behance, an online platform for connecting professionals in creative industries. Belsky experienced his own messy middle for several years after launching the platform in 2006. During this period, there were moments when his entire project seemed on the brink of falling apart. Nobody beyond his employees cared or understood his idea, and those who showed interest only expressed doubt.


Belsky was so consumed with worry and self-doubt during this difficult stage of his business that he could only maintain an appetite by taking anti-nausea pills. Many entrepreneurs find it uncomfortable to discuss this difficult period in their lives, but it is the reality of the messy middle.


Creating Milestones: Staying Focused and Inspired During Your Entrepreneurial Journey

When embarking on a new entrepreneurial or creative venture, it can be difficult to stay motivated in the absence of external rewards. Humans tend to prefer short-term rewards, but these ventures often don’t offer immediate gratification. So, it’s essential to create your own short-term goals and reward system to stay motivated.


Setting milestones and celebrating each accomplishment can provide the much-needed sense of reward that keeps us going. For instance, when Scott Belsky founded Behance, he manufactured his milestones to keep his team motivated. When Google’s search engine failed to recognize Behance as a legitimate search word, he set a goal to get it recognized without autocorrecting it to “enhance.” When his team achieved this milestone, he made sure they all celebrated it with cheap Champagne.


Creating short-term goals and celebrating each achievement, no matter how small, can give us a sense of accomplishment and reward, which keeps us motivated. It’s essential to recognize the progress we make, no matter how insignificant it may seem. This recognition can help us stay on track and push us to reach our long-term goals.


As children, we were rewarded for learning and good grades, and as adults, we’re rewarded with a regular salary. In contrast, entrepreneurial and creative ventures take time and commitment, and there are often no immediate rewards. However, by manufacturing our own milestones and rewarding ourselves for each achievement, we can stay motivated and make progress towards our long-term goals.


Importance of Self-Awareness

Self-awareness is a critical component of success, especially during times of extreme highs or lows. While triumphs and failures impact an entrepreneurial project, they also affect the founder’s personal development. Being self-aware enables entrepreneurs to remain level-headed in tumultuous times.


During successful periods, the ego tends to take over, and decision-making can become impaired. Entrepreneurs may become overconfident and dismissive of valuable advice. Conversely, during difficult times, stress can cause insecurities to surface, leading to an unfair blame game. Blaming others for problems is a coping mechanism to avoid confronting personal weaknesses. Therefore, self-awareness is essential in both highs and lows.


Being self-aware also means being open to feedback and criticism. Successful founders are receptive to criticism and integrate feedback into their operations. They are proactive in seeking constructive criticism and insights to improve their ventures. Defensive founders, on the other hand, are unlikely to succeed. They become hostile to feedback and may miss out on valuable opportunities to improve their ventures.


Entrepreneurs should strive to remain self-aware by understanding how their emotional responses may affect their decision-making abilities. Being aware of their strengths and weaknesses allows entrepreneurs to address shortcomings and seek feedback to improve their ventures. Rather than getting defensive when receiving feedback, founders should embrace it as an opportunity to learn and grow. Ultimately, self-awareness is a critical component of success, both professionally and personally.


The Importance of Investing in Future Success

When it comes to business success, focusing on short-term gains can be tempting, but playing the long game is crucial. However, this requires shifting our mindset away from the usual principles of productivity and being willing to invest time, energy, and money in potential collaborations that may not pay off immediately. Bill Gurley, the investor behind prosperous startups like Uber, understands the importance of playing the long game and spends significant time exploring ideas and avenues that may not offer short-term profits but could yield fruitful collaborations several years in the future.


Unfortunately, many business leaders lack the foresight to play the long game, as was the case with Blockbuster’s rejection of a $50 million offer from Netflix in 2000. Blockbuster executives failed to consider the potential long-term benefits of this acquisition, leading to the company’s eventual bankruptcy in 2010.


To play the long game, you must be willing to lay the foundations for future accomplishments and opportunities. This may mean exploring ideas and relationships that may not seem productive at the time but could pay off in the long run. However, this requires patience, as most relationships take time to develop and pay off, if they ever do.


The key to playing the long game is to shift our focus away from short-term gains and adopt long-term focused behaviors. This means being willing to invest time, energy, and money in potential collaborations that may not pay off immediately but could yield significant benefits in the future. While it may be tempting to focus on short-term gains, history has shown us that those who play the long game are the ones who ultimately succeed.


Startup Brainstorming


Leveraging the Highs and Always Striving for Improvement

The “messy middle” of a project can be a challenging time, but it’s also an opportunity to optimize and improve. To achieve success, it’s essential to recognize what’s working well and build upon those aspects. Optimization is about constantly striving to do something better, rather than just fixing something that’s broken.


One way to optimize is through A/B testing, a method pioneered by companies like Google to improve web-based products. A/B testing involves comparing the performance of an original product (version A) to a changed version (version B) and using the better performing option. For example, an e-commerce website might change the color of its purchase button for some customers and see if it results in more sales. If it does, the change will be applied throughout the website.


A/B testing can also be applied to everyday life, such as testing different working habits or organizational strategies. For example, a team could experiment with meeting at a different time or using a new productivity tool to see if it improves their output. If the change is successful, it can become a permanent part of the team’s routine.


Optimization is about continuously improving and recognizing that there is always room for improvement. When something works well, it’s important to evaluate why it was successful and how that success can be replicated. By optimizing and building on what works, it’s possible to accelerate progress towards the finish line and achieve success.


Embrace the Messy Middle and Never Stop Innovating

To stay ahead, you must maintain an open mindset and resist the temptation to feel entitled to success. Success in any venture requires learning from mistakes and optimizing the things you do right. As you move towards the end of your project, it’s important to maintain the mindset that got you through the messy middle. This means staying open to new ideas and being willing to take risks.


During the early stages of a venture, you have the most flexibility because you haven’t yet accomplished anything, and you feel no sense of entitlement. You’re open to making mistakes and taking risks. This is when you’re likely to have fresh ideas and insights that can make a big impact.


Maintaining an open mindset is critical to long-term success. Facebook is an excellent example of a company that has done this well. Despite their huge success, they still behave as if they’re in the messy middle of their project. This mindset has enabled them to question existing assumptions and think of ways to do things better.


Facebook started as a university directory but evolved into a social network, a platform for accessing other applications and websites, and a respected medium for online communities and groups. Facebook’s success has been due to their willingness to keep evolving and to resist the temptation to feel entitled to success.


In conclusion, the middle of a project is a period of creativity and optimization that determines future success. To stay ahead, it’s important to maintain an open mindset and resist the temptation to feel entitled to success. Embrace the messiness and take it with you wherever your journey leads you next.


We are often taught that success in entrepreneurship starts with a great idea, followed by hard work and steady progress towards achieving our goals. However, this notion is flawed. In reality, the middle phase of any venture is the most challenging, filled with highs and lows and often without external validation. To succeed, you must learn to navigate this “messy middle” and optimize your efforts. While it’s not easy, doing so significantly increases your chances of success.


It’s essential to end your venture gracefully, even if it hasn’t ended in success. Many projects don’t turn out as expected, and disappointments are inevitable. But if you’re disappointed with the outcome, don’t shut down the project and move on quickly. The final phase is critical to maintaining your reputation with investors and shareholders. Instead, own the outcome, communicate with stakeholders, and finish gracefully. Avoiding difficult conversations may seem like the easy way out, but it can harm your reputation and future ventures.

Inspired by a book “The Messy Middle”; Scott Belsky

7 minutes read

Success in the Messy Middle: Lessons from Successful Start-Ups

To achieve success in the startup world, it's crucial to understand the real journey of the most successful companies and learn how to navigate the highs and lows of the "messy middle," where 90% of start-ups fail.