20 Questions

32 Founders Share the Biggest Lessons They are Learning Right Now

Don't be afraid to admit what you don't know.
32 Founders Share the Biggest Lessons They are Learning Right Now
Image credit: Mikolette | Getty Images
Entrepreneur Staff
Staff Writer. Covers leadership, media, technology and culture.
16 min read

The most successful entrepreneurs are the first to admit that they don’t know everything. They are constantly stretching and challenging themselves.

They understand that the acceptance and application of new ideas and perspectives are not just invaluable elements for the growth and longevity of their companies. They are the things that will make them stronger leaders.

We asked 32 founders to share with us the kinds of new lessons they are excited to be learning right now.

 
32 Founders Share the Biggest Lessons They are Learning Right Now

Getting out of your comfort zone

Getting out of your comfort zone
Image credit: Angie Hicks

Name: Angie Hicks
Company: Angie’s List
Lesson: I’m always learning through change and how to manage change. That is one thing I tell people that I’m the anti-change person. But you have to learn how to evolve and work through it and guide teams through that process too. That’s one of the things I’m focusing on right now and something that is a continual thing.

Read more about Hicks: This Introvert Founder Swears by This Management Tip

 
32 Founders Share the Biggest Lessons They are Learning Right Now

Becoming savvier about numbers

Becoming savvier about numbers
Image credit: Bumble

Name: Whitney Wolfe
Company: Bumble
Lesson: I’m learning a lot about accounting. I’m not super math savvy, but I think it’s something that is incredibly important to any business. I’m working on that and learning more about different corners of the business. I'm really trying to educate not only myself but the rest of the team in categories they might not specialize in.

Read more about Wolfe: The Founder of Bumble Reveals How the 'Question of Nine' Can Help You Stay Focused

 
32 Founders Share the Biggest Lessons They are Learning Right Now

The importance of trial and error

The importance of trial and error
Image credit: Zola

Name: Shan-Lyn Ma
Company: Zola
Lesson: Every day I'm learning more about leading a fast-paced tech startup. I've learned the most from the many experiments we run within every function every day. We're all learning together. I used to think the great startups knew what they were doing and there were playbooks you could apply. I'm realizing that every situation is so different based on industry, people and timing. You need to test all the hypotheses and see what works for your particular case.

Read more about Ma: This Founder Has a 5-Minute Secret Weapon That Helps Her Focus Every Day

 
32 Founders Share the Biggest Lessons They are Learning Right Now

Raising a family

Raising a family
Image credit: Lyft

Name: John Zimmer
Company: Lyft
Lesson: I’m learning how to be a father. It’s super important, because I want to take great care of my daughter, but I also think that there is so much noise in today’s world. And the most important thing we do is raising a family and taking care of our kids, because I think they can have a really powerful impact. I want her to be happy and have a positive impact on the people and the world around her.

Read more about Zimmer: Lyft Co-Founder John Zimmer: 'You Should Never Veer Off the Path of Your Own Values'

 
32 Founders Share the Biggest Lessons They are Learning Right Now

How to grow a company culture

How to grow a company culture
Image credit: RewardStyle

Name: Amber Venz
Company: RewardStyle
Lesson: The value of our foundation. A strong foundation is what allows you to scale, allows you continued success and that comes back to planning as well. We're six years into RewardStyle, and I look at it from a technical perspective and also from a cultural perspective. This is the time where if we hadn't put the right things in place we would start seeing the company fracturing or breaking down. It's understanding the value of doing things right.

 

Read more about Venz: This Founder Shares the Mindset That Helps Her Stay On Track

 
32 Founders Share the Biggest Lessons They are Learning Right Now

Providing great customer service

Providing great customer service
Image credit: Box

Name: Aaron Levie
Company: Box
Lesson: It’s not so much new as something I’m diving into with more passion. I’m learning about how companies deliver world-class customer service. I’m learning from a range of businesses from Disney to Starbucks, reading a lot of books of those businesses and the founders of those organizations.

Read more about Levie: Why This Founder Says You Shouldn't Be Afraid to Go Big


 
32 Founders Share the Biggest Lessons They are Learning Right Now

A brand new language

A brand new language
Image credit: Masha Maltsava

Name: Jen Rubio
Company: Away
Lesson: I'm taking Mandarin and reteaching myself to play the the piano. I'm doing these things to remind myself that you are never too old to be learning new things.

Read more about Rubio: Use This Founder's Top Tip To Make Your Meetings Work For You

 
32 Founders Share the Biggest Lessons They are Learning Right Now

How to be more mindful

How to be more mindful
Image credit: BloomThat

Name: David Bladow
Company: BloomThat
Lesson: I’m in a meditation program, so I’m learning about mindfulness. The most important thing that an entrepreneur can do is put yourself in a place where your mind is sharp and fresh. Any practice the more you do, the better you get.

Read more about Bladow: This Founder Has 3 Simple Tips to Achieve Maximum Productivity

 
32 Founders Share the Biggest Lessons They are Learning Right Now

Finding a new hobby

Finding a new hobby
Image credit: Brit + Co

Name: Brit Morin
Company: Brit + Co
Lesson: My husband and I have committed to becoming better photographers together. We actually started off the year with a photo excursion to the Joshua Tree desert in southern California, and have also recently been to Iceland for a photo trip among volcanoes and glaciers. It’s such a fun way to learn something new, see the world and reconnect as a couple.

Read more about Morin: This Founder Shares the Secret to How to Make Your Business Last

 
32 Founders Share the Biggest Lessons They are Learning Right Now

How to get mentally stronger

How to get mentally stronger
Image credit: Pure Barre

Name: Carrie Dorr
Company: Pure Barre
Lesson: I’m learning more about the cognitive benefits of exercise. For a long time we've been focused on the physical benefits of exercise but the neurological benefits are really fascinating. It kind of ties in with aging gracefully. How can you live your best life into your 60s, 70s, 80s and beyond.

Read more about Dorr: This Founder Shares How to Tailor Your Schedule to Fit Your Brain


 
32 Founders Share the Biggest Lessons They are Learning Right Now

How to help others succeed

How to help others succeed
Image credit: Postmates

Name: Bastian Lehmann
Company: Postmates
Lesson: I’m learning right now to really work with a large group of people. While they all have the company in mind, they also have personal goals for their personal lives and careers. I find it fascinating to discover that and help people succeed in both.

One of the questions I ask in every interview is how can the company help them develop on a personal level? I think it’s a duty that we have. Someone who wants to work here for four years can take things from the company and those lessons can help him achieve goals and dreams in the future.

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

 
32 Founders Share the Biggest Lessons They are Learning Right Now

Teaching people how to be great leaders

Teaching people how to be great leaders
Image credit: Eventbrite

Name: Julia Hartz
Company: Eventbrite
Lesson: I have a strength in coaching leaders and keeping focused on the vision of the company. This is critical, because I can’t do it alone and I’ve surround myself with people who make me stronger and better. Build a tribe of teammates, advisors, investors, who will inspire you, push you and support you daily.

Read more about Hartz: The Day This Eventbrite Co-Founder Learned When to Speak Up


 
32 Founders Share the Biggest Lessons They are Learning Right Now

Balancing long and short-term goals

Balancing long and short-term goals
Image credit: Lucky Iron Fish

Name: Gavin Armstrong
Company: Lucky Iron Fish
Lesson: I'm learning to balance long-term objectives with short-term needs. It is really easy to get caught up in short term objectives -- sales, numbers, meeting quotas, managing your inbox. But you have to take some time to plan to achieve your long-term goals and figure out how to get there.

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

 
32 Founders Share the Biggest Lessons They are Learning Right Now

Staying informed on the latest social media trends

Staying informed on the latest social media trends
Image credit: Randi Zuckerberg

Name: Randi Zuckerberg
Company: Zuckerberg Media
Lesson: For me, I even see social media and technology as constant education. The tech is changing so quickly for someone like me. If I didn’t constantly work to keep educating myself, I wouldn't even be hired as a junior social-media manager today.  I’m constantly in a state learning, researching what’s going on, what the innovations are, what the social media platforms are doing. There is not day that goes by that I don’t try to educate myself in tech.

Read more about Zuckerberg: Why Everyone Can Use Randi Zuckerberg's Number One Focus Tip

 
32 Founders Share the Biggest Lessons They are Learning Right Now

Be a better communicator

Be a better communicator
Image credit: Nerdwallet

Name: Tim Chen
Company: Nerdwallet
Lesson: It’s really important to have a multi-disciplinary understanding of a lot of different things to come up with the best answers. I apply this at Nerdwallet. The thing that is important is to have people with different experiences contribute when relevant without too much noise. I’m learning about [building] a collaborative culture, how you facilitate communication and how we get to the truth.

 

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

 
32 Founders Share the Biggest Lessons They are Learning Right Now

Hiring and building a team

Hiring and building a team
Image credit: ThirdLove

Name: Heidi Zak
Company: ThirdLove
Lesson: Right now our business is growing very quickly, so I spend a good amount of time interviewing more senior people. The interview process is much longer for these hires, because it's important to find the people with the  right skill set, cultural fit and leadership skills. For me, it's learning how to effectively handle those interviews. That's something I've been focused on recently.

Read more about Zak: What This Founder Learned at a Farmstand Helped Her Bra Startup
32 Founders Share the Biggest Lessons They are Learning Right Now

How to scale a company sensibly

How to scale a company sensibly
Image credit: BaubleBar

Name: Daniella Yacobovsky
Company: BaubleBar
Lesson: One of the big things that we are learning right now is about continuing to scale up. How do you scale up as a business and do that in a collaborative and cross-functional way? We have grown tremendously in the past few years and one of the big lessons we have learned as a company is how to scale up and put processes in places that allow the company to continue to run smoothly but without tampering the creative spirit.

Read more about Yacobovsky: This Co-Founder of BaubleBar's Secret for Inspiration?

 
32 Founders Share the Biggest Lessons They are Learning Right Now

Providing nuanced feedback and advice

Providing nuanced feedback and advice
Image credit: GitHub

Name: Chris Wanstrath
Company: GitHub
Lesson: What I have been trying to do is to break down my skills, strengths and weaknesses, and get better at them by practicing. Then I check in with myself. I think I’ve always been good at giving black-and-white feedback, but I’m trying to get better at offering suggestions and minor feedback.

Read more about Wanstrath: This Founder Believes He Found the Answer for Burnout
 
32 Founders Share the Biggest Lessons They are Learning Right Now

Finding a better work-life balance

Finding a better work-life balance
Image credit: Stephanie Geddes

Name: Alex Friedman
Company: Lola
Lesson: To better articulate what I need, and make it happen. In a world where there is so much going on, I have to figure out how to advocate for myself in my own life and to make sure that I have the work-life balance I need.

Read more about Friedman: How You Can Use Your Computer Password to Make Your Aspirations a Reality

 
32 Founders Share the Biggest Lessons They are Learning Right Now

Trusting that who you hire will do the job you need

Trusting that who you hire will do the job you need
Image credit: Drybar

Name: Alli Webb
Company: Drybar
Lesson: Our company has grown so much over the last seven years, and we’ve hired so many people to take over a lot of areas. I don’t make every decision anymore, because we’ve brought on so many great, smart people to help us. But it is hard to let go. I struggle with it, but I find that if I trust in the people that we brought in and let people make decisions, even if they are the wrong ones sometimes, that is a learning process for me.

Read more about Webb: This Beauty Founder Shares the Secret Leadership Skill to Making a Company Thrive

 
32 Founders Share the Biggest Lessons They are Learning Right Now

How to lead people you may never meet.

How to lead people you may never meet.
Image credit: G Adventures

Name: Bruce Poon Tip
Company: G Adventures
Lesson: I'm trying to learn something that I'm calling inspired leadership. As a leader it's easy to lead people when they're all in the same room with you, but I have thousands of employees around the world now and more than 50 percent of them I might never meet in their entire careers with me -- and that's a completely different type of leadership. I want them to wake up every day, love the brand and work harder than they ever have. I want them to achieve that potential. I want them to love what they do. I realized that the future success of the company is going to be whether I can lead this way.

Read more about Poon Tip: I Was About to Shut Down My Business but I Changed My Mind. Here's Why.

32 Founders Share the Biggest Lessons They are Learning Right Now

How to build a space conducive to ideas.

How to build a space conducive to ideas.
Image credit: Casper

Name: Jeff Chapin
Company: Casper
Lessson: Most of my learning and thinking right now is about how to build and design the right office. I have to learn how to build a design culture, how to inspire people, how to enable them to come up with new ideas. It’s becoming larger and past the point where I actually know what everyone's working on. For long-term sustainability, we have to get that infrastructure and attitude correct.

Read more about Chapin: Behind a $100 Million Mattress Startup, Casper Co-Founder Shares Advice on Finding Success as an Entrepreneur

32 Founders Share the Biggest Lessons They are Learning Right Now

Take customer feedback into account.

Take customer feedback into account.
Image credit: Brooklinen

Name: Vicki Fulop
Company: Brooklinen
Lesson: I learn from our Brooklinen team and customers every day. And that's important because we're fortunate enough to have surrounded ourselves with really smart, creative and hardworking people. I want to listen, empower them and let their brilliant ideas come to the forefront and support them in executing those ideas. The same thing is from the customer. They are the people sleeping on the product and experiencing our business, our service our products, our advertisements and responding to it via email and social media. So, it's a constant listening, learning and analyzing, so that we can always serve them to the best of our ability and make things that make people happy.

Read more about Fulop: Use This Founder's Simple Email Strategy to Keep Burnout at Bay


 
32 Founders Share the Biggest Lessons They are Learning Right Now

Holding onto values as you grow.

Holding onto values as you grow.
Image credit: Nirav Tolia

Name: Nirav Tolia
Company: Nextdoor
Lesson: This idea of of being able to create a high- performance organization and do so in a way that's values-centric, embraces compassion and empathy. Also, being a conscious leader is something that's been a real game-changer for me as a CEO. I think it's critical, because I believe that it's the way that organizations will most likely to win.

Read more about Tolia: This Successful Entrepreneur Shares How You Can Build A High-Performing Company While Staying True to Your Values


 
32 Founders Share the Biggest Lessons They are Learning Right Now

Understanding that achieving big goals takes time.

Understanding that achieving big goals takes time.
Image credit: Frankie Marin

Name: Christene Barberich
Company: Refinery29
Lesson: I'm always practicing and trying to get better at patience. Most of the best and most influential things that have happened in my life have taken a longer time to cultivate than I ever thought they would. I think ambitious people have a warped sense of time; we expect everything to happen much sooner than it actually does.

Read more about Barberich: Why Your Done List is Just as Important as Your To-Do List


 
32 Founders Share the Biggest Lessons They are Learning Right Now

Establishing company culture continuity.

Establishing company culture continuity.
Image credit: Sarah Kauss

Name: Sarah Kauss
Company: S’well
Lesson: What I'm spending my time on right now is culture and learning how to be a great company as we grow and evolve. We grew really quickly, and it's been fun, but I don't want to lose the heart as we get processes and structure. I want to make sure that as a team we don't lose the magic.

Read more about Kauss: This Successful Entrepreneur Shares Why You Should Do The Thing You Dread Most First Thing Every Day

32 Founders Share the Biggest Lessons They are Learning Right Now

Embracing hobbies to clear your mind.

Embracing hobbies to clear your mind.
Image credit: Barbara Corcoran

Name: Barbara Corcoran
Company: Forefront Venture Partners
Lesson: What I'm learning now is how to dance. It's so delicious, this physical movement for the sake of not getting in shape or doing the right exercise but for the sheer joy of movement. I'm also trying to be a better gardener, but I've been doing that my whole life. There is always so much to learn there.

Read more about Corcoran: Shark Tank's Barbara Corcoran Explains Why You Must Make Time in Your Schedule For Fun

32 Founders Share the Biggest Lessons They are Learning Right Now

How to put the needs of others before yours.

How to put the needs of others before yours.
Image credit: Tristan Walker

Name: Tristan Walker
Company: Walker & Company
Lesson: I’m learning how to be the best father I can be. My son turned 3 in September. He's at this stage of his life where he remembers things, and you want to make sure that he's remembering the rights things. He's looking to me for the most positive reasons. So, it's an interesting experience for me to go through, because it forces me to be less selfish.

Read more about Walker: This Successful Entrepreneur Explains Why You Don't Need Billions to Build a Brand That Hits Home

32 Founders Share the Biggest Lessons They are Learning Right Now

How to build a company that inspire change.

How to build a company that inspire change.
Image credit: Payal Kadakia

Name: Payal Kadakia
Company: ClassPass
Lesson: I’ve been studying the work by Stanford professor BJ Fogg on behavioral design. He has a three step method for designing products to encourage behavior change. His method is thoughtful, methodical and impactful. I love building products to help people live better lives. It’s what we do at ClassPass and it’s my personal mission as well.

Read more about Kadakia: This Successful Entrepreneur Explains Why You Can't Succeed Unless You Invest in Yourself

32 Founders Share the Biggest Lessons They are Learning Right Now

How to make products that appeal all over the world.

How to make products that appeal all over the world.
Image credit: Melanie Perkins

Name: Melanie Perkins
Company: Canva
Lesson: Introducing Canva to more markets has been a huge and incredibly exciting learning experience for the whole team. We have conducted a lot of research into the design aesthetic of many countries and have deliberately created localised templates for various festivities and celebrations. For example, in the United States there is Halloween, but in Germany our design community would seek out Oktoberfest templates. I think it’s important to always put our users first -- what they need and what they look for -- to ensure Canva can be their one-stop-shop for all their design needs. It’s a learning process that never stops as design continues to evolve.

Rad more about Perkins: She Was Told 'No' 100 Times. Now This 30-Year-Old Female Founder Runs a $1 Billion Business.

32 Founders Share the Biggest Lessons They are Learning Right Now

How to get inside the mind of the customer.

How to get inside the mind of the customer.
Image credit: Zach Sims

Name: Zach Sims
Company: Codecademy
Lesson: We launched a data analysis course in December, and I take almost all of our courses, so I'm in the middle of it. As a CEO, understanding the metrics of your company is super important. I have a pretty good grasp of that, but I'm learning more about how to go even a level deeper and understand what we're doing, how well we're doing it and how we can better help our learners.

Read more about Sims: The Surprising Reason Why This Young Tech Entrepreneur Swears By Pen and Paper

32 Founders Share the Biggest Lessons They are Learning Right Now

Time management in the face of rapid growth.

Time management in the face of rapid growth.
Image credit: Squarespace

Name: Anthony Casalena
Company: Squarespace
Lesson: I'm learning to manage my time effectively at each phase of Squarespace's growth, and I'm making changes to how we run the company to continue to operate at scale. The way we operate and how I engage with an 800-person team is very different from how I did things at 200 or 50.

Read more about Casalena: The Founder of Squarespace Explains Why You Don't Want to Raise As Much Money as Possible

My Queue

There are no Videos in your queue.

Click on the Add to next to any video to save to your queue.

There are no Articles in your queue.

Click on the Add to next to any article to save to your queue.

There are no Podcasts in your queue.

Click on the Add to next to any podcast episode to save to your queue.

You're not following any authors.

Click the Follow button on any author page to keep up with the latest content from your favorite authors.

Add to Queue
  • 32 Founders Share the Biggest Lessons They are Learning Right Now
  • 1. Getting out of your comfort zone
  • 2. Becoming savvier about numbers
  • 3. The importance of trial and error
  • 4. Raising a family
  • 5. How to grow a company culture
  • 6. Providing great customer service
  • 7. A brand new language
  • 8. How to be more mindful
  • 9. Finding a new hobby
  • 10. How to get mentally stronger
  • 11. How to help others succeed
  • 12. Teaching people how to be great leaders
  • 13. Balancing long and short-term goals
  • 14. Staying informed on the latest social media trends
  • 15. Be a better communicator
  • 16. Hiring and building a team
  • 17. How to scale a company sensibly
  • 18. Providing nuanced feedback and advice
  • 19. Finding a better work-life balance
  • 20. Trusting that who you hire will do the job you need
  • 21. How to lead people you may never meet.
  • 22. How to build a space conducive to ideas.
  • 23. Take customer feedback into account.
  • 24. Holding onto values as you grow.
  • 25. Understanding that achieving big goals takes time.
  • 26. Establishing company culture continuity.
  • 27. Embracing hobbies to clear your mind.
  • 28. How to put the needs of others before yours.
  • 29. How to build a company that inspire change.
  • 30. How to make products that appeal all over the world.
  • 31. How to get inside the mind of the customer.
  • 32. Time management in the face of rapid growth.
Next Slide