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As a serial entrepreneur, I learned the hard way what not to do as a startup founder. From copying instead of innovating to picking strategic investors too early, I’ve made too many mistakes that have cost me time, money, and sleepless nights. But through these setbacks, I’ve gained invaluable insights that have helped me succeed in my later 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 honest, I was not prepared for this. After some initial 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 smarter decisions, stay competitive, adapt to challenges, and attract and retain top talent. Reading and talking to inspiring people boosts creativity and allows founders to think more innovatively.
Here’s what I do:
I book 30 minutes in advance to read blog posts and newsletters. I listen to podcasts when I exercise. And I have a personal key result: reading four business books in one quarter.
I don’t know how many times I’ve completely screwed this up. Everything was important; The next keynote, fundraising, a unique opportunity to collaborate with a large corporate, the launch of a new (absolutely needed) feature… It’s important to focus on what’s important; This allows a founder to prioritize the most important tasks and reach the startup’s goals within their limited time and resources. The most relevant success factor is to focus on number one. If you’re pre-product-market fit, focus on getting there. If you’re seeing traction, focus on scaling.
Here’s what I do:
I spend two hours every day on my number one thing. But first, you need to figure out what’s most important to you, and that’s why I recommend creating 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, which causes a company to lag behind competitors. I was never 100% satisfied with the state of the startups I was leading, but I was sometimes a little too satisfied and therefore, not hungry enough.
What shall I do:
I define 2-3 ambitious but realistic goals and focus primarily on these. It doesn’t matter if it’s a sale goal or a house in Tuscany, only one thing matters: I really want to achieve them.
I always thought that a board of directors and my network was enough, but only at TRIQ, we implemented an advisory board. From then on, I would never miss it again. It is flexible and complementary; You’ll get expertise from people you could never hire.
What shall I do:
At GROWTH UNTLD, I’ve had an “informal” advisory board from the beginning, and now I’m making it official.
I am officially a stubborn person. It turns out from such an assessment. And this can become a disadvantage when you do not listen to others and wish the impossible. But often, you are considered stubborn, for example, when it comes to best practice frameworks like OKRs, experimentation, consistency in communication, or adherence to processes.
What shall 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 maximum freedom to my employees, but I am very conscientious and demanding regarding following procedures and using these frameworks.
I hear it so often that founders look for strategic investors, even in the early stages. Now listen closely: I did it, and it was a complete mess. A strategic investor can block many opportunities, determine your exit, or in the worst case, kill your startup.
What shall I do:
Seek strategic investors only after your strategy is clear. Do it later in the round when you are already planning your exit. If you still see a great opportunity, forge a strategic partnership or craft a shareholder agreement wisely.
I can’t argue with hiring great people. But an organization is a team and not a game of individuals. I’ve tried this “laissez-faire approach” several times and always failed. Leading people can be exhausting, especially giving (and receiving) feedback.
What shall 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? well, what should we do? Suddenly it becomes easy to lead.
Neglecting agreed upon milestones can hurt the company/founder’s reputation (especially with investors), lower team morale, result in missed opportunities, have financial consequences, and There may even be legal implications. I am a moonlighting boy who sets almost unattainable goals; It was never a good idea to communicate with them.
What shall I do:
I only communicate 70% of my “secret goals” and keep my promises. It helps me deliver and keeps me motivated. Founders must prioritize meeting milestones to maintain the trust and support of investors, team and stakeholders.
In one of my previous startups, where I was the CEO, we had about 5 million active users and could not build a sustainable business model. Is it product-market fit? No. PMF is achieved when your customers pay enough for your solution to be profitable (at least in the future). So we had to lift and lift and lift. This whole thing inspired me to help startups do better.
What shall I do:
I test my idea without making 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 the 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 in particularly stressful times. Then, we know when the person is simply operating on autopilot; We have patterns when we are under stress and return to them over and over again.
What shall I do:
First, I learned the importance of picking the right co-founders or key players on a team. I usually do an assessment to understand if the person is perfecting team skills, how they behave in stressful times, and when they are in their strength areas. My duty as a founder is to ask for help when I am stressed and to provide help when I know someone needs it.
Photo by Austin Distel on Unsplash
I’m a fairly good salesperson and have always struggled with communicating my vision to others, which is the problem with many founders.
What shall I do:
Embrace founder-led sales instead of growing too fast: Founders often believe that hiring a sales team will lead to 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 with respect to the product. That’s why it’s essential that I define process, create a playbook, attend sales meetings, provide feedback, and feed the build-measure-learn loop before scaling.
I sometimes got hired based on a good CV and failed. While a good CV can indicate that a candidate has the skills and experience needed for the job, it doesn’t mean they’ll 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 recruiter can doom your startup.
What shall I do:
While a candidate’s CV should be considered as 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 have been fearless in firing employees who do not align with company values.
The last thing a startup lacks is opportunity; Therefore, you should say no more than yes. It is 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 lack of resources, ultimately hurting your business or personal goals.
What shall I do:
Saying no to opportunities can also help you prioritize your time and resources. When you have a clear understanding of 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 prioritize, and I use it daily. And, of course, if you’re pre-product-market fit, then reaching the PMF is all that matters.
As a founder, it’s not uncommon to rely on your intuition or gut feeling when deciding which features or products to implement. Ultimately, 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 affect the success of your product or company: it can result in products that don’t meet your customers’ needs. or which fail to gain traction in the market. market.
What shall I do:
The key is to balance your intuition with data-driven decision making. This means using customer feedback, market research and analysis to make decisions. Testing ideas at scale and running experiments allows me to validate my assumptions and make data-driven decisions before implementing something big.
As a working person, it’s easy to get caught up in the demands of work and neglect self-care. I’ve been there myself, feeling stressed and tired from overworking and not caring about my own needs. It is 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, decreased immunity, and even physical and mental health problems. When you’re not taking care of yourself, you feel stressed, overwhelmed, and unable to perform at your best.
What shall I do:
I exercise regularly, eat a balanced diet, and set aside time for relaxation and self-care. I have a gym membership and I do cardio and strength training four to five times a week. 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 intake of sugar, which can affect my energy levels and mood. I set aside time each week to do activities that help me relax, like reading or taking a bath. I recently bought a sauna for my home; A great way to relax and reduce stress.