Get All Access for $5/mo

What 9 Successful Entrepreneurs Wish They Had Done Differently From not connecting to a mentor to not selling sooner: Even uber-successful people have regrets.

By Alex Turnbull Edited by Dan Bova

Opinions expressed by Entrepreneur contributors are their own.

In 2004, many of us had the opportunity to become shareholders in Google for the very first time. Most of us passed on that offer. Had we decided to invest, by cashing out today, we would make more than $5 for every dollar we put in. To me, that's a regret.

Related: Bono Regrets Putting U2's New Album in Your iCloud Library

And it's not my only one: We've all made decisions (or failed to make decisions) we wish we could take back. Even the most successful entrepreneurs are no different. I asked nine founders about their biggest regrets in business. And I learned a lot from what they shared. I hope you do, too:

1. Hiten Shah, KISSmetrics and Crazy Egg

Regret: Not looking for problems.

"Most of my early failures were a result of building things people didn't want. What I would have done differently is to find the right problem to solve for customers before writing a single line of code. It would have saved me a countless amount of time and resources." -- Hiten Shah

2. David Hauser, Grasshopper

Regret: Not investing in culture.

"I wish I had focused more time, thought and money into the company culture from day one. I have since discovered this to be the most important factor in the success of scaling any business. Core values, core purpose and integrating these into everything will give the largest returns you will ever see as a founder." -- David Hauser

3. Noah Kagan, AppSumo

Regret: Not connecting with a mentor.

"I would have gotten a mentor who's done the things I wanted to accomplish in the future. Why not learn from someone who's already done the things you want to do? People will read this and still not do anything. Instead, send one email to the person you respect in business the most, asking for a chat. You'll be surprised how much it energizes you and helps you succeed." -- Noah Kagan

Related: 10 Instinctive Decisions You Will Regret Forever

4. Dharmesh Shah, HubSpot

Regret: Not selling sooner.

"One of my bigger regrets in my first startup is hanging on to it too long. I ran that company for about 10 years. I had acquisition offers along the way, but the valuations never matched my growth projections. I probably held off on selling that company for three to four more years than I should have. I knew that I was no longer excited about the industry, and had aspirations to do something different -- and hopefully bigger. Eventually, I did sell the company, which freed me up to go back to MIT for graduate school -- and ultimately start HubSpot. If you're heart's not in it, be willing to make the sacrifice to let something go so you can free yourself up for whatever new things are ahead." -- Dharmesh Shah

5. Andrew Warner, Mixergy

Regret: Not asking for feedback.

"When I got my first customers at Mixergy, I was embarrassed to ask them why they bought and what I could do to improve Mixergy for them. I thought they were going to tell me that there were too many things to improve because my site sucked. When I finally started calling them, I heard about a lot of things that needed improving, but my customers really liked me and my work, and many of them offered to help improve what wasn't working the way they wanted." -- Andrew Warner

6. Wade Foster, Zapier

Regret: Not trying new things in school.

"I would have definitely experimented with more stuff in high school and college. Programming, science, selling: I was a bit too shy and nervous about my social image to try different things, and I ended up having some catching up to do." -- Wade Foster

7. Adii Pienaar, WooThemes and Receiptful

Regret: Not living in the moment.

"I was obsessed about always moving from point A to B to C, which meant I was never really present in any given moment. This also meant that the highs on the rollercoaster ride were fleeting, and the lows, always brutally around-the-corner. I've since learned to enjoy the journey itself (more than the destination) and appreciate small victories and special moments much more." -- Adii Pienaar

8. Mike McDerment, FreshBooks

Regret: Not being focused.

"In the early days of building FreshBooks, I struggled to find focus. As an entrepreneur, you see opportunity everywhere. It's in your DNA -- your business becomes a hammer, and everything looks like a nail. I could see an infinite number of paths that the company could take. I was fortunate enough to have a good advisor who taught me an invaluable lesson before I managed to killed the company. He said, "Mike, there's a four-letter word in business: FOCUS. If you don't focus, you'll be drowning." He encouraged me to pick one thing and go as deep as possible… and [to do that] just when I thought it was deep enough, to push harder, because you can always go a hell of a lot further than you initially think." -- Mike McDerment

9. Jason Lemkin EchoSign

Regret: Not picking a committed co-founder.

"Never co-found a company with anyone, no matter how talented, that isn't committed for at least seven-to-ten years. It takes that long to build anything that really matters." -- Jason Lemkin

Related: 5 Inventors Who Regret the Products They Created

Alex Turnbull

Founder and CEO, Groove

Alex Turnbull is the founder and CEO of Groove, a customer support app for startups and small businesses. Follow Groove’s journey to $500,000 in monthly revenue on its blog.

 

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Editor's Pick

Science & Technology

5 Automation Strategies Every Small Business Should Follow

It's time we make IT automation work for us: streamline processes, boost efficiency and drive growth with the right tools and strategy.

Business Process

How CEOs Can Take Control of Their Emails and Achieve Inbox Zero

Although there are many methodologies that leaders can use to manage their emails effectively, a consistent and thought-through process is the most effective way to systemize and respond to emails and is a step of stewardship for the effective leader.

Business News

Former Steve Jobs Intern Says This Is How He Would Have Approached AI

The former intern is now the CEO of AI and data company DataStax.

Side Hustle

'Hustling Every Day': These Friends Started a Side Hustle With $2,500 Each — It 'Snowballed' to Over $500,000 and Became a Multimillion-Dollar Brand

Paris Emily Nicholson and Saskia Teje Jenkins had a 2020 brainstorm session that led to a lucrative business.

Marketing

5 Critical Mistakes to Avoid When Giving a Presentation

Are you tired of enduring dull presentations? Over the years, I have compiled a list of common presentation mistakes and how to avoid them. Here are my top five tips.

Leadership

Visionaries or Vague Promises? Why Companies Fail Without Leaders Who See Beyond the Bottom Line

Visionary leaders turn bold ideas into lasting impact by building resilience, clarity and future-ready teams.