As a serial entrepreneur, I’ve learned the hard way what not to do as a startup founder. From copying myself instead of innovating to picking strategic investors too early, I’ve made plenty of mistakes that have cost me time, money, and sleepless nights. But through these failures, I’ve gained invaluable insights that have helped me succeed in my subsequent ventures.
In this blog post, I’m sharing 15 epic failures I’ve experienced as a founder and the lessons I learned from them. Whether you’re a first-time founder or a seasoned entrepreneur, these lessons can help you avoid some of the most common pitfalls in the startup world.
I started my first business in my early twenties. And to be frank, I was not ready for it. After some early successes, I started copying myself instead of innovating — a VERY BAD IDEA. I first had to learn how to learn, and learning helps startup founders make better decisions, stay competitive, adapt to challenges, and attract and retain top talent. Reading and talking to inspiring people enhances creativity and allows founders to think more innovatively.
Here’s what I do:
I book 30 minutes early to read blog posts and newsletters. I listen to podcasts when I exercise. And I have a personal key result: reading four business books a quarter.
I don’t know how many times I totally screwed this up. Everything was important; the next keynote, fundraising, a unique opportunity for collaboration with a big corporate, the launch of a new (totally essential) feature… It’s crucial to stay focused on what matters; It allows a founder to prioritize the most critical tasks and reach the startup’s goals within their limited time and resources. Focus on the number one thing is the most relevant success factor. If you’re pre-product-market fit, then focus on getting there. If you’re seeing traction, then focus on scaling.
Here’s what I do:
I spend two hours each day on my number one thing. But fore and foremost, you need to understand your most important thing, and therefore I recommend having a one-page strategy with your one-year goals and using OKRs for its execution.
Being comfortable with the status quo can lead to complacency, causing the company to fall behind competitors. I was never 100% satisfied with the status of the startups I was leading, but I was sometimes just a little bit too satisfied and, therefore, not hungry enough.
What I do:
I define 2–3 ambitious but realistic goals and focus mainly on these. No matter if it’s a sales goal or a house in Tuscany, The only thing that matters: I really want to achieve them.
I always thought that the board of directors and my network were enough, but only at TRIQ, we implemented an advisory board. Since then, I would never miss it again. It’s flexible and complementary; you will get expertise from people you could never hire.
What I do:
At GROWTH UNTLD., I had an “unofficial” advisory board from the start, and now I’m building it officially.
I am officially a stubborn person. That’s what an assessment revealed. And this can become a disadvantage when you no longer listen to others and wish for the impossible. But often, you’re supposed to be stubborn, for example, when it comes to best practice frameworks like OKRs, experimentation, consistency in communication or adherence to processes.
What I do:
I have developed a detector for situations where I tend to be stubborn without any reason and always try to speak less and listen more. Additionally, I seek feedback and aim to grow daily as a person, entrepreneur, and advisor. On the other hand, I give my employees maximum freedom, but I am very conscientious and demanding regarding adhering to processes and using these frameworks.
I hear it so often that founders seek strategic investors, even in the early phases. Now listen closely: I did it, and it was a total mess. A strategic investor can block many opportunities, dictate your exit, or, worst case, kill your startup.
What I do:
Only seek a strategic investor after your strategy is crystal clear. Do this in a later round when you already plan the exit. If you still see a great opportunity, build a strategic partnership or structure the shareholder agreement wisely.
I can’t argue with hiring great people. But an organization is a team and not a game of individuals. I took this “laissez-faire approach” many times and always failed. Leading people can be exhausting, especially giving (and receiving) feedback.
What I do:
I set strategic goals and align the team with the OKR framework, which is the main content of 1-on-1 and team meetings. Are we on track? No? Okay, what do we need to do? Suddenly, leading becomes easy.
Missing agreed-upon milestones can hurt a company’s/founder’s reputation (especially with investors), decrease team morale, result in missed opportunities, cause financial consequences, and even lead to legal implications. I’m a moonshot guy who set almost unachievable goals; communicating them was never a good idea.
What I do:
I only communicate 70% of my “secret goal” and keep my promises. This helps me deliver and keeps me motivated. Founders must prioritize meeting milestones to maintain investor, team, and stakeholder trust and support.
In one of my previous startups, where I was the CEO, we had around 5 million active users and could not build a sustainable business model. Is this product-market fit? No. PMF is achieved when your customers pay enough for your solution to get profitable (at least in the future). So we had to raise and raise and raise. This whole thing inspired me to help startups do it better.
What I do:
I test my idea without building a product; only then, when I understand the value prop, do I start building and improving it with customer feedback. I focus only on finding PMF at this stage. You can read more about my approach in this article.
Working with a co-founder can be intense. Specific charter characteristics only emerge over time and become established, especially in stressful times. Then, when the person is only functioning on autopilot, we know this; we have patterns when we are under stress and fall back into them repeatedly.
What I do:
First, I learned the importance of choosing the right co-founders or key players in a team. I usually conduct an assessment to understand if the person is completing the team’s skills, how she behaves in stressful times, and when she’s in her power zone. My duty as a founder is to seek help when I’m under stress and provide support when I realize someone needs it.
I can sell quite well and have always struggled to communicate my approach to others, which is many founders’ problem.
What I do:
Embrace the founder-led sales instead of scaling too fast: Founders often believe hiring a sales team will result in more sales. But the company is still learning and improving the product; this iterative process is challenging for salespeople to manage. The founder best understands what works and what can be done regarding the product. So it is essential that I define the process, create a playbook, am present in sales meetings, give feedback, and feed the build-measure-learn loop before even scaling.
I sometimes hired based on great CVs and failed. While a great CV may indicate that the candidate has the necessary skills and experience for the job, it does not necessarily mean they will be a good fit for your team or your startup’s culture. As a founder, hiring is one of your most important responsibilities: one bad hire can kill your startup.
What I do:
While a candidate’s CV should be considered part of the hiring process, it should not be the only factor you rely on. You should also consider their personality, work ethic, and communication skills. Additionally, I involve the team in every hiring decision and became fearless in firing employees who do not align with the company’s values.
The last thing missing in a startup is opportunities; therefore, you must say no more than yes. It’s important to remember that not all opportunities are created equal. Saying yes to every opportunity that comes your way can lead to a lack of focus and a drain on resources, ultimately harming your business or personal goals.
What I do:
Saying no to opportunities can also help you to prioritize your time and resources. When you clearly understand what is important to you, you can focus your efforts on those areas and make the most of your resources. Having a one-page strategy helps me understand the priorities, and I use it daily. And, of course, If you’re pre-product-market fit, reaching PMF is everything that counts.
As a founder, it’s not uncommon to rely on your intuition or gut feeling when deciding what features or products to implement. After all, intuition can be a powerful tool for generating new ideas and anticipating customer needs. However, relying too heavily on intuition can be a risky approach, especially when making decisions that will impact the success of your product or company: it can result in products that don’t meet your customers’ needs or that fail to gain traction in the market.
What I do:
The key is to balance your intuition with data-driven decision-making. This means using customer feedback, market research, and analytics to inform decisions. Testing ideas and running experiments at scale allows me to validate my assumptions and make data-driven decisions before implementing something big.
As a hardworking individual, it’s easy to get caught up in the demands of work and neglect self-care. I’ve been there myself, feeling stressed out and on the brink of burnout due to overworking and not caring for my needs. It’s important to recognize that taking care of yourself is not a luxury but a necessity. Neglecting self-care can have serious consequences, including decreased productivity, lowered immunity, and even physical and mental health problems. When you’re not taking care of yourself, you’re more likely to feel stressed, overwhelmed, and unable to perform at your best.
What I do:
I exercise regularly, eat a balanced diet, and set aside time for relaxation and self-care. I have a gym membership and work out four to five times weekly, doing cardio and strength training. In addition to exercise, I also pay attention to my diet and eat nutritious, whole foods. I try to avoid processed foods and limit my sugar intake, which can impact my energy levels and mood. I set aside time each week to do activities that help me unwind, such as reading or taking a bath. I recently purchased a sauna for my home; a great way to relax and reduce stress.
