"Had to make a lot of mistakes" — Shark Tank mentor Daymond John reflects on his entrepreneurial journey

On February 5, 2025, Shark Tank investor Daymond John shared a post on Instagram about his entrepreneurial journey. His caption encouraged business owners generating over $1 million in revenue to join an exclusive event for training, networking, and strategy development. He talked about the importance of learning from experienced entrepreneurs rather than waiting for opportunities.

At the event, CEO Day with Daymond John, he spoke to fellow entrepreneurs about his early struggles in business. Reflecting on his past, he said,

"I wish I had groups like this. When I was coming up, I had to make a lot of mistakes. I had to close the business three times from '89 to '92."

Shark Tank star Daymond John added that when he first got his shot and had money in the bank, he ran through $20 million of liquid. He added that he saw it happen every single day.

---

Shark Tank star on overcoming early struggles and Dyslexia

Shark Tank mentor Daymond John has often spoken about his challenges in school. In a past Instagram post that he shared on April 14, 2021, he put a vintage photo of himself and revealed that he struggled academically due to undiagnosed dyslexia. He mentioned that he grew up thinking he wasn’t smart enough because he only discovered his learning disability after graduating high school.

The caption said,

"He got made fun of, doubted, and mocked for choosing to pursue an industry that was different than the status quo of everyone around him⁣. He worked over 80 hours a week to make his dreams come true." ⁣

He also faced skepticism from others when he decided to start his clothing brand, FUBU. His persistence paid off, turning FUBU into a well-known apparel brand. Reflecting on this, he has encouraged aspiring entrepreneurs to keep pushing forward despite setbacks.

In an interview with the Yale University Center for Dyslexia & Creativity, John explained that while he struggled with reading and language arts, he excelled in math and science. He shared that he would quickly grasp concepts in those subjects, earning high grades. However, he found reading exhausting and faced challenges with spelling simple words.

“Literally, I couldn’t spell the word ‘because’ for 4 or 5 years. I wouldn’t know how to spell my middle name, Garfield. When I read a book, I got tired,” he said.

Recognizing his strengths, the Shark Tank star adapted his learning methods. He took part in a co-op program in high school, alternating between working for a week and attending school for another. This experience introduced him to the business world early, giving him valuable insights into real-world commerce.

---

Business success and lessons learned

Daymond John has stated that business success requires discipline, financial literacy, and strategic decision-making. Speaking about financial responsibility in an interview with CNBC in 2016, he said,

"It’s not about how much money you make; it’s about how much you keep. I’ve seen people earn millions and lose it all because they didn’t have the right mindset."

John also believes in the power of mentorship. In an interview with Forbes in 2015, he credited much of his success to surrounding himself with the right people and continuously seeking knowledge. He said the most "successful" entrepreneurs understand that they don’t have all the answers. They "seek out" mentors, stay humble, and keep learning every day.

---

New episodes of Shark Tank season 16 air every Friday at 8 pm ET on ABC.