What 25 Entrepreneurs, Investors and Celebrities Wish They Knew at the Age of 25

Photo credit multibriefs.com

Today is my 25th birthday. I’m not big into celebrating birthdays, but I use these yearly reminders that I’m getting older as an opportunity to reflect.

I’ve been fortunate to meet and interact with some amazing people during my short time as an entrepreneur. While I don’t ask my entire network for things often, I decided to reach out in advance of my birthday to see what they wish they would’ve known when turning 25.

Here are 25 of the responses I received to the question (email me at Cory@CoryLevy.com if you’d like to see all 50+):

Aileen Lee, Founder and Managing Partner of Cowboy Ventures

  • No matter how busy life gets, don’t fall out of the habit of regular workouts, reading, and regular quality time with friends and family
  • Over the years, there will be friends who have down periods — a bad work situation, a bad personal or health situation. Take the time to reach out, listen, help and support them no matter how busy you are
  • At the end of your life, it will likely be the ways you helped others, and the big memories/stories you were a part of — not the business triumphs — that will make you smile and feel like you had a life well lived
  • Live music and dancing. go no matter how old or busy you get, and go a lot before you have kids (if you are going to have kids)
  • When you get older, every piece of food that goes in your mouth makes you fat. so if you have a good metabolism now, enjoy it to the max! especially pasta. lots of pasta!!
  • Take time to learn about companies your smart friends join (it might be they are joining a public company whose stock has tanked, or a startup whose story is not well understood). if i’d invested in Amazon when my smart friends joined “that little book startup” or netflix when “the internet is going to put that CD company out of business” i would be writing this email to you from Bora Bora!

Albert Wenger, Managing Partner at Union Square Ventures

“I wish I had known more about relaxation and mindfulness techniques — would have been a lot easier to learn back then how to stay rational and not let my emotions hijack me (which still happens to me sometimes these days).”

Aria Finger, CEO of DoSomething.org

  • Life is LONG. The folks you work with/hang out with/partner with now will be in your life in 20 years. Be good to them. It will always come back to you.
  • Radical Candor. In a compassionate way. The old “Honesty is the best policy” gets used over and over again for a reason. It’s true.

Ashton Kutcher, Actor and Investor

Ashton Kutcher at the 2013 Teen Choice Awards Photo Credit: Getty Images
  • Spend more time contemplating, categorizing, and prioritizing that which you can do, that which you should do, and that what you must do!
  • Being serious doesn’t make you mature it just makes you serious.
  • Tackle big problems as long as you care enough to see them through.

Chris Sacca, Investor, Founder of Lowercase Capital

“The quicker you can stop seeking the approval of others the happier you will be.”

David Cohen, Founder of Techstars

“Don’t marry that woman! :-) (my first marriage was a divorce). in all seriousness, do it now, not later (whatever “it” is). life is short. shoot for the hole.”

Dustin Dolginow, Early Stage VC at Maiden Lane and Accomplice

“I was living in NYC when I turned 25. My wish is that I had been more purposeful about making, maintaining and deepening impactful relationships in my life. At the time, I was focused on chasing cool and absorbing the city life. It is remarkable how a single person can change your life. The really good ones are hard to find and it takes consistent effort. I learned that lesson when I moved to Boston with no good friends.”

George Zachary, Investor, Partner at Charles River Ventures

George Zachary

“When I was 25, there are SO many things I wish I knew.

If I had to say one it would be that no matter what you plan for or think you have control of in your life, things good and bad will come into it that are part of the human condition and cannot be avoided. In fact, they are opportunities (as I learned) to get a clearer picture on life which will lead you into unexpected paths that you never ever conceived of before. And it will be exciting.”

Jessi Hempel, Editor at Backchannel, Previously at Wired

“At 25, I wish I knew that I already had every single thing I needed to succeed at work, love, and life. Also, I wish I knew I was better looking than I’d ever be again, no matter how much I wanted to be thinner or prettier.”

Jeremy Stoppelman, CEO of Yelp

Yelp CEO Jeremy Stoppelman

“Here are some things I’d share with my previous self…

  • Over the next couple years your confidence should steeply climb as you nail down who you are and what you’re uniquely good at.
  • Spend less time at bars and clubs, you won’t look back on that as time well spent.
  • Time feels infinite at 25, but will feel finite by 35 (ok maybe 36). Enjoy and relish every minute of your youth!”

Josh Elman, Investor and Partner at Greylock

“I wish I understood that being a little more patient would help win the long game. The people who pushed for promotions and more responsibility didn’t do as well over the next decade as the ones who simply did awesome work and never complained. It all comes in time. Enjoy life along the way!”

Justin Mateen, Co-Founder of Tinder

Photo credit: Vinisha Mulani and Maddi D

“The time frame between 25 and 30 feels like a blink of an eye. You can never replace your youth so enjoy every minute of it by living in the moment.

1. Don’t be afraid to stretch beyond your comfort zone and take calculative risks… the worst that can happen is that you gain knowledge and that unique knowledge is exactly what gives you an edge over the average person.

2. An idea is just an idea. When and how you execute that idea is what makes it real.

3. Every journey has highs and lows. Maintaining your composure during the lows help position you perfectly to maximize the highs. 💪🏻💪🏻”

Kevin Hartz, Founder of Eventbrite

  • Take bigger risks
  • Surround yourself by the smartest people on the planet
  • Find something meaningful that has “legs” and work on it for decades. creating value Takes a very long time and requires persistence (Amazon, Google, Berkshire Hathaway)

Lake Dai, Venture Capitalist, Entrepreneur, Adjunct Professor

“Pursue something meaningful that you are passionate about. Join people with same value, same passion. Work hard towards it. Money should never be the goal.”

Matt Mullenweg, Founder of Wordpress

“I wish I’d known that it is okay to fail, okay to let someone go in either a personal or professional context, and important to take care of your health.”

Michael Jones, CEO of Science, Former CEO of Myspace

  • “Take more risks
  • Realize mediocre “things” take up the room to find great “things”
  • If whatever you’re doing is not only difficult but also feels like elements outside of your control are not supportive in your direction, you may be doing the wrong thing or doing the right thing at the wrong time.
  • Everything has a cost, know what you are willing to give up in order to get what you want.”

Mike Hopkins, CEO of Hulu

I wish I knew that I was capable of more, took more risks, understood that failure is a gift as long as you learn. Oh, and that Microsoft was a pretty good buy…”

Naval Ravikant, AngelList

Naval Ravikant

“I wish I hadn’t stressed as much about the future and just enjoyed the present. The future works out the way it’s going to work out — usually fine and mostly out of your control, whereas the present slips by, never to be recovered.”

Nancy Lublin, Founder and CEO of Crisis Text Line

“Things I wish I knew at 25:

  • That Apple was a good investment
  • How to cook a turkey
  • How to change a tire on my car
  • That my my friendships and work relationships will never be as important as my family (even the family I don’t like much)
  • How to read a financial spreadsheet”

Niko Bonatsos, Managing Director at General Catalyst

“Be more thoughtful about who I spent time with.”

Peter Diamandis, Entrepreneur and Innovator, Co-Founder of Human Longevity

1. Don’t do things to make money, do them because you love them… the money will come.

2. When it’s time to get married, find someone who has maximum in common with you, your best friend, who loves the same things… not your opposite.

3. Your passion and purpose are your most valuable assets in life.

4. Take the time to sit down with your parents, grand-parents, whoever is close to you and record their life story in audio, video, what ever… ask them hard questions.

Ron Conway, Investor, Founder and Managing Partner of Angel Investors LP

“I wish I realized the power of establishing meaningful relationships.
It ends up one of the biggest assets a person has (other than their reputation) is their relationship network.”

Sam Altman, Entrepreneur and Investor, President of Y Combinator

“Take more risk.”

Sean Rad, Co-Founder and CEO of Tinder

“Don’t feel the pressure to be perfect or have all the answers. Being a great leader means you’re able to chart a course, and surround yourself with a team who each have their own strengths and weakness, but together in concert you can arrive to the destination.

If we never faced hard moments, if we never had to overcome obstacles, then we would never learn, we would never grow. As much as it hurts in the moment, see the hard moments as opportunities to grow.”

Tyra Banks, Model, Producer, CEO of TYRA Beauty

“When I was 25, I wish I knew that that dude I was soooooo into that rejected me would one day chase me down but I’d be repelled by his lack of intellect (even though 15 years later, he still had an extremely beautiful face! But, that just ain’t enough anymore.)”

Questions for you (please answer in the comment section below or email me): What piece of advice do you think is the most helpful? If over 25, what do you wish you would’ve known? If under 25, what do you want to learn before you reach that age?


Cory Levy is an entrepreneur, investor, and thought leader on tech startups and entrepreneurship. As the Co-Founder and COO of After School — the largest teen-focused social network in the U.S. — Cory is helping redefine how young people connect, share, create, and engage in positive social change.

Cory is also the Founder of Internapalooza — the premier one-day event for Silicon Valley Interns to meet with and learn from successful entrepreneurs and tech companies.

Cory’s writing and entrepreneurial efforts have been featured and covered in Under30CEO, College Startup Magazine, Fortune, Fueled, VentureBeat, Bloomberg, and TechCrunch. Cory took an absence after studying CS at the University of Illinois to start the company with co-founder Michael Callahan. Connect with Cory on Twitter @Cory and on Facebook.