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5 Entrepreneurs Share Their Biggest Mistakes & Lessons

5 Entrepreneurs Share Their Biggest Mistakes & Lessons

Monday June 03, 2019,

5 min Read

When you try something new you are bound to make mistakes and that is OK! And a reality check here is that you are not the only one in the boat. Everyone has their own set of mistakes and failures. What important is that you learn from them and never repeat it. And what best is to come out openly and share them with others, because it might help someone by giving them analysis.

Yes, the experience is a great teacher but my friend there is no harm to learn from someone else’s’ experience too. There are people who have achieved a lot but all we see is their success, not the mistakes and failures behind. That’s a trap because what is visible is the glory and good and not the background which was tough and ugly. To investigate the back story is also important.

If you are an entrepreneur, we feel your pain as no one will tell you what to do and how to do. But don’t worry because some successful entrepreneurs have stepped out and shared their biggest mistakes. So, take a pen and make notes and don’t do what they did wrong. Following are the 5 entrepreneurs sharing their Biggest Mistakes & Lessons.

Satish Gaire, CEO at DirectPay / WooAgents / Podmio:

Satish Gaire Says that the mistake he made as a SaaS company is not starting off early. In early days, he was chasing perfection which he could never achieve. This delayed his product to get to market, causing a lot of loss. But he learned from it and has a suggestion for you

Satish Said: “These days, I work in a minimal viable product "MVP" style for my early state start-ups, my job is to get to market first even if it means that I have some bugs & less features. We fix the issues & add features as we go. To everyone starting out, just start & get it done. Don't wait for the perfect moment.”

Rossanna Figuera, Co-Founder and Ambassador of Good Things:

During the initial years of their company, one of company’s trusted team members violated security protocols and destroyed an important piece of equipment that cost the company thousands of dollars in lost revenue while jeopardizing several jobs.

She said: “I was under severe stress, and called a staff meeting and asked everyone to vote on the future of the reckless team member. This was too much to handle for my young, inexperienced staff. For a long time afterward, employee morale was at its lowest and it took serious effort to rebuild people’s trust back. I carried a feeling of failure for a long time”.

But the valuable lesson she learned was that leadership involves making the tough decisions that sometimes only you can make.

Saul Fleischman, CEO at a social media toolkit company RiteKit:

Saul Fleischman told that there was one mistake he made more than once. He allocated too much staff time to get PR for their self-funded startup’s products. Journalists have sold their souls to investors because they want early investment opportunities, freebies, and perks.

The key point he shared was- “If you bootstrap what you’re building, approaching major news portals is fruitless. They may present themselves as discoverers of tech breakthroughs but what gets their attention is who – other than the founders – have footed the bills. I know now to let the press come to us”.

Richelieu Dennis, Sundial Brands, New York City:

He somehow underestimated how difficult it would be to break the status quo. Dennis misjudged how ingrained traditional retailer segmentation strategies were and did not take in account that how long it would take to persuade retailers that historic and old segmentation approaches they follow need to be changed as they fail to fully serve all customers. 

But this didn’t set him back and he says- “I learned that even when something makes sense and is a more effective approach, it can be extremely difficult for people to depart from what they know and have always done. Generally, we look to take the road less traveled because we truly believe that just because something has been done one way doesn’t mean that it’s the best way”.

Hiten Shah, Co-Founder at KISSmetrics:

He and his co-founder spent $1,000,000 on a web hosting company that never launched. They thought that they were perfectionist so they just created the best thing they could without even trying to understand what customers need and cared about. But following the league, Hiten Says- “I have now learned to spend smart, optimize for learning and focus on customer delight ".


If any of the above sound similar to you that you were about to do or you are doing without realization then you know what to do now. Starting a new business is not easy and surely you will make mistakes but that is completely fine. What is important is that you don’t give up in a tough time and learn from your mistakes.

Success will come in your way if you truly believe in your business idea, learn from your own mistakes and other’s experience as well.