10 Founders Share What Their Worst Boss Taught Them


You can learn from even the most frustrating experiences.

Hulton Archive | Getty Images

1. Communicate clearly.

1 / 10

2. Follow the golden rule.

2 / 10
Lucky Iron Fish

3. Have strong convictions.

3 / 10

4. Be a mentor.

4 / 10
Baked By Melissa

5. Follow through.

5 / 10

6. Connect with every employee.

6 / 10
Nicole Franzen

7. Leave your ego at the door.

7 / 10

8. Treat everyone with respect.

8 / 10

9. Don’t stand in the way of innovation.

9 / 10
Bloomberg | Getty Images

10. Have a clear vision.

10 / 10
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Staff Writer. Covers media, tech, startups, culture and workplace trends.

We’ve all had bosses that make us crazy -- whether it was a supervisor with a big temper, one that watched your every move or the one that never knew what he wanted. But even if at the time it was frustrating or demoralizing, there is an upside: You’ll never catch yourself being that kind of manager.

We caught up with 10 successful entrepreneurs who shared with us the lessons they learned from the worst bosses they’ve ever had.

Name: Daniella Yacobovsky
Company: BaubleBar
Lesson: One of the things I have learned is to communicate openly and honestly with the folks you work with. Try to understand where their requests and feedback are coming from and be open to feedback. When you’re first starting and you’re a small company, it’s definitely easier to do. As you grow and have more people, it is a harder thing to scale but that doesn’t take away it’s importance.

Read more about Yacobovsky: This Co-Founder of BaubleBar's Secret for Inspiration? Always 'Keep Your Eyes Peeled.'


Name: Gavin Armstrong
Company:  Lucky Iron Fish
Lesson: People who are bullies act that way because they are insecure about something else. They are very demeaning and not appreciative.

You want to be very respectful of people working with you. Remember they work with you, not for you. Be complimentary of their work, because they are putting a lot of time and effort into it.

Read more about Armstrong: This CEO Has Helped Thousands -- and He's Just Getting Started


Name: Merrill Stubbs
Company: Food52
Lesson: Being indirect about what you want or what you expect is a really terrible tactic for managing people. It makes them feel like the ground is shifting beneath them -- that's an impediment and distraction from people doing their best work.

Read more about Stubbs: The Life-Changing Book That Helps This Entrepreneur Think Big


Name: Melissa Ben-Ishay
Company: Baked By Melissa
Lesson: The importance of open communication. When I think of the worst boss I ever hard, I don’t think of just one person.

I didn’t have a mentor. I didn’t have someone who wanted me to succeed. I didn't have someone who took the time to sit down, have a conversation with me and help me be better at my job. So now, I really make the effort to be clear and honest with my employees and sit down with them and communicate.

Read more about Ben-Ishay: How Getting Fired Turned Into Sweet Success for This Entrepreneur

Name: Oliver Kharraz
Company: Zocdoc
Lesson: I learned to only make promises that I can keep. I remember how upset I was when promises were made to me that were not kept, and I promised myself that I wouldn’t do that.

Read more about Kharraz: This Founder Says to Succeed You Need to Question Everything

Name: Jennie Ripps
Company:  Owl’s Brew
Lesson: I learned how important it is to engage with my own team and also to ensure that there is buy-in across the board at an individual level.

Read more about Ripps: The One Thing This Entrepreneur Does Each Day to Stay Productive

Name: Tim Chen
Company: Nerdwallet
Lesson: Ego gets in the way of success. I worked at a hedge fund that had a real “Lord of the Flies” feeling. It was pretty crazy. The problem with ego is the best ideas don't win, because you have trouble facing the truth.

Read more about Chen: Nerdwallet's Founder Shares the Worst Advice He Ever Got

Name: Kyle Hill
Company: HomeHero
Lesson: The worst boss I had was actually a soccer coach I had in high school. I wouldn't say he was a bad coach, but he yelled at me a lot. I realized that was something I could not handle. So my dad ended up pulling me from the team. I didn't understand it at the time. I thought it wasn't a big deal, and I had a tough skin.

But my dad was adamant about this, he said, “I don't want people talking down to you because it hurts your self confidence. I need you to have the highest self confidence going into in everything you do in life; otherwise you're not going to want to do it.”

I think it lends itself to being treated with respect and dignity. My dad said, “You can be stern, you can bench my son, you can take him aside and tell him what he needs to improve on. But don't publicly reprimand him.”

Even to this day, I tell people, “If you're upset with me, whether it's my co-founder or an employee, talk to me like an adult.”

Read more about Hill: What This Founder Does to Stay Completely Focused

Name: Bastian Lehmann
Company: Postmates
Lesson: One thing I try to do is help the people that want to do more. I want to help them realize that when they are at Postmates.

The worst boss I ever had told me that I couldn’t do that. He was weak and afraid someone was more hungry than him. When I saw someone trying hard, and they gave it everything they had, that someone would not give them guidance and help them succeed.

Read more about Lehmann: This Founder Shares the One Trait He Looks for in Every Hire


Name: Heidi Zak
Company: ThirdLove
Lesson: The one thing I've noticed from having different types of bosses is that the best ones have a clearly articulated vision of what the team is working toward. You have to communicate it effectively and do it often. That's what I try to do; you can't say it too often.

Read more about Zak: This Founder's Best Advice for Entrepreneurs: To Succeed, Entrepreneurs Need to Get Comfortable with Being Uncomfortable


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