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8 Successful Entrepreneurs Give Their Young Selves Lessons They Wish They’d Had Known Then



Looking at the success trajectories of today’s disruptors–from Pandora cofounder Tim Westergren to Wikipedia’s Jimmy Wales–it’s easy to think that they had everything figured out from a young age. But many of today’s success stories learned lessons later in life that they wished they had known as they were beginning their careers. The eight investors and entrepreneurs below share the advice they wish they had gotten in their early twenties.

Tim Westergren: Avoid the risk of not trying and the regret of wishing you had.

Tim Westergren, the founder and Chief Strategy Officer at Pandora, said if he could offer his younger self one piece of advice, it would be to realize from an early age that it’s far more haunting to live with the regret of having not followed your instincts–even when those instincts required a diversion from the beaten path–than to have followed your gut and failed. Luckily for Westergren, he was one of the few who did follow his passions and that pursuit led him to found a company with a market cap of $2.5 billion.

“Be sure to ‘notice’ ideas when you have them. Stop. Take the time to consider them seriously. And if your gut tells you they’re compelling, be fearless in their pursuit,” Westergren said. “For most people, the idea of chasing a personal passion or being entrepreneurial is simply something they don’t think of themselves doing. We’re so programmed to walk well-trodden paths. But, we live life only once. So, rather than avoiding the risk of trying, avoid the risk of not trying. Nothing is more haunting than thinking, ‘I wish I had…’.”

Jimmy Wales: Spend wisely early in life so you can achieve the financial independence to follow your dreams.

Jimmy Wales, the founder of Wikipedia–which according to its own Wikipedia page is a collaboratively edited online encyclopedia–said the advice he would share with the younger generation is to be strategic and thoughtful with expenses at an early age so that you can afford to pursue your passions.

“I think one of the things that most 21-year-old people should do is to recognize now that you can make life choices which control your expenses, and that controlling your expenses is one of the most crucial steps toward the kind of financial independence that you need in order to follow your dreams in the future. Whether it is a change of job, or an entrepreneurial dream, the less you NEED to spend each month, the easier it is to follow those dreams. There are several rules of thumb that can help with this, but one of my favorites is to never go into debt to finance any kind of luxurious consumption. Only go into debt if necessary for some kind of investment, like student loans, for example.”

Bill Ready: Surround yourself with great people and be fearless in pursuit of game-changing ideas.

Bill Ready, the CEO of Braintree–the mobile payments platform for online and mobile commerce that counts companies like Uber, Airbnb, and Fab as clients–shared two key pieces of advice that he wish he had known when he was younger.

“There are two main things I wish I had known when I was 21,” Ready said. “Back in the late 1990s when I was a 19-year-old engineer at Netzee–much like other bright, young, ‘hot-shot’ engineers today–I had this sense that I knew everything, and I didn’t realize the importance of really listening to those who were more experienced. What I have realized since then, is that one of the most important things you can do is to surround yourself with great people, and to listen to them. The second piece of advice I would give is to be fearless. Don’t be afraid to pursue revolutionary ideas, and don’t hold back simply because you’re going up against seemingly unconquerable competitors in your market space. At Braintree, many of our competitors are huge, established companies in the market with market caps in the billions–but we’re not afraid of going after them.”

Alexander Ljung: Realize the power of simplicity.

Alexander Ljung, the cofounder and CEO of SoundCloud–the popular audio platform that has raised more than $63 million in venture funding, according to CrunchBase–shared the importance of learning the power of simplicity in today’s complex world.

“In recent years, T.S. Eliot’s reported quote–‘If I had more time, I would have written a shorter letter’–has stuck with me when making numerous decisions specifically around leadership, design, and product. The advice I would offer my 21-year-old self is to remember that it takes more mental (and sometimes physical) bandwidth to create something simple or communicate something complicated in basic terms, but ultimately, that’s a lot nicer for the user experience,” Ljung said. “It’s not about building every feature or understanding everything the first time around. It’s about creating the best, tailored experience for your community and company. I’d remind myself of the importance to leverage design as a decisive advantage and to not be afraid to challenge people to break down their knowledge into easily digestible, clearer statements.”

Philippe Courtot: Focus on what makes you truly happy.

Philippe Courtot, the CEO and Chairman of Qualys–the enterprise cloud security firm that went public last year–emphasized the importance of doing what makes you happy; pursuing what actually makes you happy ensures that you’ll put the needed energy, time, and resources behind your work.

“If I had one piece of advice to give my younger self it would be to stop doing what makes you unhappy and focus on what makes you truly happy,” Courtot shared. “This philosophy, strongly advocated by the Dalai Lama, seems simplistic but its power lies in the fact that it forces you to reflect on what is really important to you and not be distracted by what other people think. If I could give myself one more advice it would be to not be afraid of trying. This builds on the first piece of advice, as we can only learn what makes us happy or unhappy through our own experiences.”

Bing Gordon: Work as hard as you can, and then work harder.

Bing Gordon, a General Partner at Kleiner Perkins Caufield Byers–who counts Twitter, Spotify, and Path in his portfolio of investments–was frank in his advice. Ultimately, hard work is what is going to make you successful. That, and the added benefit of having an influential mentor to help guide you on the path to success, is the combination that will get you to where you want to go.

“I’ve always regretted that I didn’t start working in business until I was 28 years old,” Gordon shared. “After decades of hiring college grads, I’ve learned that the people who get the most opportunities also start fast. They overachieve from the very beginning. They ask the best questions and always seem to have good ideas. As one Hollywood producer once said, ‘Work as hard as you can and then work harder.’ But the number one piece of advice I would share is to recruit a mentor. Find someone you admire who is at least one generation older, and has no direct authority over you. Lack of context and perspective can cost you months and years–with a bad career choice, an unwise relocation, short-term negotiating posture, and, generally speaking, sophomoric thinking. Jeff Brenzel, Dean of Admissions at Yale, has the best advice on how to recruit a mentor: ‘All professors desire acolytes; so carry their favorite book of theirs under your arm, and go introduce yourself with a question about their book.’”

Paul Bennett: Take the time to listen.

Paul Bennett, the Chief Creative Officer at IDEO–the highly creative global design consultancy that has done work for clients from Samsung to GE–said the one piece of advice he wished he had known in his early twenties, was to focus on listening rather than rushing to come up with a quick, yet uninformed, response.

 “Listen more,” Bennett advised. “For most of my twenties I assumed that the world was more interested in me than I was in it, so I spent most of my time talking, usually in a quite uninformed way, about whatever I thought, rushing to be clever, thinking about what I was going to say to someone rather than listening to what they were saying to me. Slowing oneself down, engaging rather than endlessly debating and really taking the time to hear and learn is the greatest luxury of becoming older.”

Scott Weiss: Surround yourself with leaders in your field.

Scott Weiss, a Partner at Andreessen Horowitz–who counts Platfora, Quirky, and Skout in his portfolio–emphasized the importance of learning in the workplace, and pointed out that smaller companies are great places to learn and grow.

“Whatever vocation you decide on, track down the best people in the world at doing it and surround yourself with them. Aim high and be ridiculously persistent. Your happiness is at the intersection of your passions and learning from great people. Working at a big company sucks–avoid it. Smaller companies are 10 times better for learning. Be generous with your time and money–it has an amazingly fast payback. Be in the moment with everyone you love–and this frequently means tuning out work completely. And drive slow in parking lots.”

This article was written by Grace Nasri.


Women on Top in Tech – Dawn Dickson, Founder and CEO of PopCom, Inc. and Founder of Flat Out of Heels



(Women on Top in Tech is a series about Women Founders, CEOs, and Leaders in technology. It aims to amplify and bring to the fore diversity in leadership in technology.)

Dawn Dickson is the Founder and CEO of PopCom, Inc. (formerly Solutions Vending, Inc.), the company behind PopCom Kiosks and the PopCom API, which provides a software solution to make vending machines more intelligent. She created the company after her own struggles to find vending machines that could sell her roll-up flat products, Flat Out of Heels, at high-traffic areas like airports.  She was awarded First place in the PowerMoves NOLA Big Break pitch Competition and second place in the 2016 SBA Innovate Her Challenge.

What makes you do what you do? 
I love solving big problems and working with amazing people to get it done.

How did you rise in the industry you are in?
After working in the vending industry for three years selling Flat Out of Heels in vending machines in airports and nightclubs, I was frustrated with the lack of data I was able to collect from my hardware. I also wanted more engaging and interactive experiences for my customers and after speaking with several retailers they felt the same way. That is when I decided to focus on PopCom and developing a software solution to solve the data problem in self-service retail.

Why did you take on this role/start this startup especially since this is perhaps a stretch or challenge for you (or viewed as one since you are not the usual leadership demographics)? 
The fact that I am not the usual, leadership demographic is the main reason why I was up for the challenge. The industry is in need of a change and I believe someone with a unique and different perspective and experience is needed. I look forward to collaborating with the industry leaders and veterans to build a product that everyone loves and finds value in.

Do you have a mentor that you look up to in your industries or did you look for one or how did that work? How did you make a match if you did, and how did you end up being mentored by him/her?
I am involved in several different industries and sectors – retail, self-service retail, hardware, software…so I have to learn a lot of information quickly.  There are several people that I look up to, follow their career, and seek advice from. I was fortunate to be able to participate in some of the country’s top accelerator and entrepreneurship development programs, including Techstars, Canopy Boulder, and the BIxel Exchange – the mentorship and network I gained from these programs has been invaluable and very instrumental in our progress.

Now as a leader how do you spot, develop, keep, grow and support your talent? 
I have learned that spotting talent takes time, it takes patience, and building relationships with people and networks to meet new people, most of my connections come from introductions. I focus on finding the right fit for the company culture, there is a lot of great talent out there, but the culture is different, I want us to be on the same wavelength. I am fortunate to have met some great people through the programs I was in that came on as mentors, advisors, and eventually full time team members. I take time to get to know my team individually and understand what their personal goals and ambitions are, ask them what their dream job looks like, understand their needs so they can be happy at work and be fulfilled. I believe in self-care and making mental health a priority, if a person is good within themselves they radiate positivity and are more productive.

Do you consciously or unconsciously support diversity and why?
I am a black woman so I am diversity. Naturally, we attract people we can relate to and have things in common, so I found that my team was heavily female and my diversity initiative was finding more men…when I thought about it I found it funny. Now I have a balanced team of men and women from diverse backgrounds, experiences, and perspectives which is exciting.

What is your take on what it takes to be a great leader in your industry and as a general rule of thumb? 
To be a great leader you have to be a team player, my rule is I never ask someone to do something that I would not do myself. I also have a rule to give the team the freedom and flexibility to work when and how they are most productive. That means some of us working different hours and being in the office different days, but happy team builds the dream!

Advice for others?
My advice is never give up if you believe in it. I started my company selling shoes in vending machines in 2011, it took me 7 years, a few failed hardware attempts, and many people telling me it would not work because the market was not ready. I was patient and what I believed would happen is happening. In May PopCom is bringing the PopShop to market, a next gen smart vending machine to sell and sample products. Our API will be ready in July and for the first time vending machine and kiosk owners can understand their conversion rates and have the level of data and analytics available that eCommerce stores have, but better. It has been a long journey and I feel it is just getting started, but I am only here because I never gave up.

If you’d like to get in touch with Dawn Dickson, please feel free to reach out to her on LinkedIn:

To learn more about PopCom, please click here.

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Callum Connects

Elaine Zhou, Co-Founder of China Women Equipping Center



Elaine went on a journey of self discovery and once she knew her true self she could be successful in her own business.

What’s your story?
I am very proud of where I came from and I am grateful for where I am living and working today. Singapore is my adopted home and it is my aim to always contribute to and serve this country and its people.
Twelve years ago, I moved to Singapore for an internship opportunity. I was twenty one years old and I didn’t have any friends, I didn’t speak English, I didn’t understand the culture or the customs. Everything was new and strange to me. Everything was difficult, but my parents had tremendous faith in me.
My parents have worked diligently on the family farm to raise us and send us to college. My parents had a huge influence on me. The important things I learnt from them are to love, to never give up, to be a hard worker and to have a can-do attitude. These are the qualities that I embrace in my daily life.

What excites you most about your industry?
We offer more than just training. Our business is a resource to be leveraged for transformation, improved teamwork, leadership behaviours, communication skills, relationship skills, coaching skills and increased job satisfaction and productivity.
Our passion and purpose is to help people grow as leaders and to create tremendous results by serving others well. We take people to daring destinations, beyond their imagination.
My greatest joy is to see people grow, change and transform and live a purposeful life; this is what motivates me to do more and do it well.

What’s your connection to Asia?
I was born in China and I have spent all my adult and professional life in Singapore.

Favourite city in Asia for business and why?
Singapore and China.
Singapore is a very sophisticated and systematic country. It is a structured and highly efficient business environment and people are generally nice and honest. Also, the convenience and diverse culture is a great advantage for people who want to settle down there, no matter if they are from the East or West. You always feel at home in Singapore.
I also like China because of its fast growth. The population and the market is here. However, it takes time to settle in because of the language barrier and the very different traditional culture. But you will also find it is very interesting and you’ll want to learn more about China. The people are nice if you know them well. It is always about relationship first and business second, and when you are in a business meeting, you really have to master the skill of “reading the air.” It is a skill to let people know and understand you; your values, your background, why you think in that way or why you do or do not do certain things. Doing business in China is like swimming in the ocean; it is an abundant ocean and it is full of risks. Always know your values and stay true to yourself and make decisions close to your heart. It will help you see things more clearly and get things done in a way that doesn’t violate your values.

What’s the best piece of advice you ever received?
“Be yourself, Elaine.” That is the best advice I have ever received. It was a big ‘aha’ moment for me. It was also the moment I truly and honestly looked within myself. I realized that when I am being my true self, and not trying to be someone else, I am able to connect with people instantly in a genuine and authentic way. It is a great feeling.

Who inspires you?
There are so many people who encourage me, lift me up and challenge me everyday. My mentor, John Maxwell who helped me discover my purpose in life; Michael Griffin, for his passion for Christ which is contagious and Wayne Dyer, my spiritual mentor who passed away in 2016. Also, people who are living with a purpose and striving everyday for their dream, they really inspire me. My clients, mentees and students. When I see that joy and peace in them, that inspires me to do more and do well. My team inspire me, especially when they said, “Elaine, I joined the business because of you.” They inspire me to make it work for the team and the business because it is beyond my own self interest. I am grateful for having so many people in my life who inspire me.

What have you just learnt recently that blew you away?
China is a big country, we all know that, and it is also an internet giant. Recently on a team meeting, one of the directors who manages a successful beauty business, shared with us, that everybody is on the internet, especially on WeChat. People are obsessed with online communities – for ordering food, getting taxis, forging relationships, connections and friends. Almost anything and everything can get done online. But right now, there is a new trend; more and more people want the “offline” experience. It usually takes one to two hours from one place to another in Beijing, but people want to make the effort to have a real connection with other people, to attend networks, seminars, workshops and business meetings.

If you had your time again, what would you do differently?
I started my first business when I was 24 years old, it failed. One year later, I started my second business and after a year and a half, I closed down the operation. After several painful experiences and two failed businesses, I started to look within myself, and seriously and intentionally invested in my personal growth at the age of 28. If I could turn back time, I wish I could have grown a lot earlier. I strongly believe that the level of our success is determined by the level of our self growth and we are always learning, everyday. But I also understand it is not the only way to live. I also consciously and intentionally try to live in the now. It is a beautiful and great way to live. In fact, I am grateful for what I have gone through; the pains, setbacks and challenges in my earlier life.

How do you unwind?
I like to stay connected with nature. For example, taking a walk barefoot on the grass and smelling the roses on the street. Having a beer or coffee along the riverside with friends; reading a good book; hunting for nice restaurants; swimming or running.

Favourite Asian destination for relaxation? Why?
Thailand – nice beaches, food and people.
Bali – fantastic beaches and food, great people.
Malaysia – Nice food and people, particularly Langkawi, Penang and KK.
Of course Singapore, it is always a place dear to my heart. It’s my home.
There are a lot of other interesting places in China which I am still exploring.

Everyone in business should read this book:
The Law of Success by Napoleon Hill
The Science of Getting Rich by Wallace Wattles
The Power of Now by Eckhart Tolle
Tao Te Ching: Change Your Thoughts, Change Your Life by Wayne Dyer
Developing the Leaders Within You by John C.Maxwell
Start with Why by Simon Sinek
These are some of the books that truly transformed my thinking and shaped my values.
I used to read a lot of different types of books, from sales, marketing, branding and management to different business models. I found it is really hard to master all of it and I was not optimizing my own strengths.
Entrepreneurship is a skill to be learnt. But it is really important to recognize what we are good at and what we are not so good at. We can not be everything.
Entrepreneurship is a journey of self-discovery and soul searching. It is all about learning and striving. We should try and always remember why we started our business in the first place.

Shameless plug for your business:
The China Women Equipping Center, is something both my team are I are very proud. We have put our hearts and souls into it, to help women in China grow and transform. As a developing country and with the rise of China, people are not lacking in money, everywhere is full of opportunity, but the challenge is the civilizations, values and faith. In fact the Chinese government puts a lot of effort into improving and shaping the international image to ensure it is making progress. But people are still facing a lot of pressure, especially women.
One of our business partners who is runs traditional Chinese medicine retail stores, shared that 80% of his patients are female, and the reason they are coming to see him are anxiety and depression.
Our China Women Equipping Center creates a safe and comfortable environment for women to help build their values and characters. My local team and I are very passionate about our mission and purpose. Beijing is our headquarters in China. We are planning to take three to six months to establish our business in Beijing and grow and expand to other major cities in China after that.

How can people connect with you?

This interview is part of the ‘Callum Connect’ series of more than 500 interviews

Callum Laing is an entrepreneur and investor based in Singapore. He has previously started, built and sold half a dozen businesses and is now a Partner at Unity-Group Private Equity and Co-Founder of The Marketing Group PLC. He is the author two best selling books ‘Progressive Partnerships’ and ‘Agglomerate’.

Connect with Callum here:
Download free copies of his books here:

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