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

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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.

Callum Connects

Denise Mossis Kipnis, Founder & Principal of ChangeFlow Consulting

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Denise Mossis Kipnis’ curiosity in people and the world, lead her to set up ChangeFlow Consulting.

What’s your story?
I’m driven by curiosity. Having been the only one in a room who looks like me for most of my life, I developed a curiosity about who stays, who leaves and who thrives in minority/majority situations including when and how connection and collaboration happen. I was a systems thinker long before I knew what that was, always asking why and so what; and seeing the pieces, the whole, and the places in between. So helping people and organisations move through the complexity of transformation feels natural to me.

What excites you most about your industry?
I see change and inclusion as two sides of the same thing; I don’t practice one without the other. Some people see change as death, as loss, as exhausting. And it can be. But I see in the work I do as an opportunity for something new or hidden to emerge. When an organisation understands that it is first a group of people, who themselves represent and belong to groups of people, and it begins to tackle what it would mean to understand and learn from all that talent, all that diversity, to have them all working for and not against the organisation, to truly unleash all that their people have to offer; that’s magic.

What’s your connection to Asia?
Change and inclusion are personal values as well as professional strengths. For me, living and working outside of the States was a bold experiment to see whether any of the stuff I’d learned about change and inclusion would work outside of the US. My husband and I targeted Asia specifically: it would be the greatest contrast, culturally speaking, for me; and a unique career springboard for him.

Favourite city in Asia for business and why?
Although I’ve practiced in other cities, I am biased towards Singapore. In some ways it’s what Los Angeles is to the rest of the United States, a microcosm of sorts. The regional/global nature of it means that so many different nationalities and cultures are represented. As a result of this mix, you never know what you might get. In some situations, cultural dynamics are obvious, sometimes subdued. The variability is compelling.

What’s the best piece of advice you ever received?
“Never ask anyone to do anything you wouldn’t do yourself.” Michael Rouan.

Who inspires you?
Often it’s a “what” not a “who.” I can get inspiration from a passage in a book or a situation in a movie, as well as a turn of a phrase or watching people interact. I often make the biggest connections between the various threads I’m working on when I’m sitting in someone else’s event.

What have you just learnt recently that blew you away?
I’m honestly not blown away by much. Instead, I’m struck how circular things can be: ideas often come back around with a slightly different twist and I watch the way it shakes things loose for people. I recently sat through a workshop on Self as Instrument, and despite being thoroughly versed already, I learned something. In preparing for a panel on design thinking, I unearthed a new language to describe things.

If you had your time again, what would you do differently?
You’ve caught me at a good time. I’m sitting in appreciation and gratitude for all my experiences, because I wouldn’t be who I was today if all that has happened, didn’t. And yet one thing comes to mind: It wasn’t until I redesigned my website two years ago (shout out to Brew Creative!) that I realised I hadn’t made explicit agreements with my past clients as to what I could share publicly about our engagement, or whether I could use their logos in my promotional materials. In my business, confidentiality is so important, and yet I need to be able to talk about the work as reputation and experience leads to the next success, and so on. It turned out a lot of the contacts I had known had left the organisations where the work was done, so they couldn’t help at that point. So the practice I’m carrying forward is to get those agreements up front, and to make sure my relationships in client systems are broad as well as deep.

How do you unwind?
Science fiction, puzzles, wine.

Favourite Asian destination for relaxation? Why?
Home. I don’t travel to relax, I travel to learn and explore.

Everyone in business should read this book:
Built to Change, by Ed Lawler and Chris Worley. To my knowledge, it’s the first pivot from advising organisations away from stability and toward dynamism, from strategic planning to strategizing as an action verb; to blow up the traditions and rigidity that impede organisations from developing change capability.

Shameless plug for your business:
We’re taught that there are two kinds of people: those who see forests, and those who see trees. There is a third type, my type, and we see the ecosystem. Worms, climate, birds, the spaces in between. This is the perspective organisations need to be successful in solving complex problems and thriving in change.
ChangeFlow uniquely blends four disciplines (two of which are multi-disciplinary in themselves): organisation development, culture and inclusion, change management and project management.

How can people connect with you?
Facebook: https://www.facebook.com/ChangeFlowConsulting/
LinkedIn: https://www.linkedin.com/in/dmorriskipnis/
LinkedIn Company page: https://www.linkedin.com/company/4862954/
Email: [email protected]
Website: http://www.changeflowconsulting.com

Twitter handle?
@ChangeFlow

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:
twitter.com/laingcallum
linkedin.com/in/callumlaing
Download free copies of his books here: www.callumlaing.com

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Callum Connects

Agnes Yee, Legal & Compliance Recruiter of Space Executive

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Agnes Yee started Space Executive in Singapore, which is a hub for businesses in some of the world’s fastest growing economies.

What’s your story?
After graduation, I joined a design media company as a Business Development Executive, during the era when ‘reading a magazine online’ was unheard of. I believe that laid the foundation for being unfazed by rejections.

I fell into recruitment pre-GFC and rode the highs and lows in the early years. A decade later, I decided to set up my own recruitment company, partly because I could. I’m acutely aware of the face that being an Asian female in Singapore is sometimes a privilege, and that many women in the world are living a very different existence.
Thereafter, we joined Space Executive as part of a merger. I am currently the Partner of Space Executive, a recruitment company focused specialist disciplines, including Legal, Finance, Digital, Sales and Marketing and Change. We also run Space Ventures, a venture capital business, which invests in seed and pre-series A businesses.

What excites you most about your industry?
On a daily basis, we’re influencing how one spends a third of their day. It is interesting how the Internet has transformed the industry, and I’m excited to see how we can harness technology to bring us to the next phase of this business.

The VC is an extension of applying our skills and experience in reading people. We very much invest in the people as much as the idea. Being a native Singaporean, it’s been exhilarating watching Southeast Asia becoming a hotbed of ideas; and young entrepreneurs simply daring to dream.

What’s your connection to Asia?
I’m a born and bred Singaporean. I love that I speak both English and Mandarin, grew up playing with Indian friends and eating Malay food.

Favourite city in Asia for business and why?
Singapore for the low barriers of entry to set up a business, but has to be China (and Hong Kong) for their hunger and constant innovation.

What’s the best piece of advice you ever received?
青春不要留白 which translates to ‘Don’t waste your youth.’

Who inspires you?
Anyone who has gone against the grain.

What have you just learnt recently that blew you away?
It wasn’t recent but reading the article on https://waitbutwhy.com/2015/12/the-tail-end.html never fails to blow my mind how little time we have left. Charting our lives in weeks, and realising I only have enough time left to enjoy 60 Christmas turkeys, read 300 books (all if I’m lucky); and mostly, I’m left with the last 5% of the time that I spend in-person with my parents.

If you had your time again, what would you do differently?
I’m cognisant that every decision I made in life has brought me to where I am today, and I wouldn’t change one thing. But I’d really like to have had more time to travel.

How do you unwind?
Exercise and wine.

Favourite Asian destination for relaxation? Why?
Trekking any mountain in Asia. It brings us back to the most basic. To overcome elements of nature and our own mind.

Everyone in business should read this book:
Start with Why, Simon Sinek

Shameless plug for your business:
Space Executive started in Singapore, a hub for businesses in some of the world’s fastest growing economies. We assist organisations in accessing a targeted and specialised, and often times transient talent pool.

Out of Singapore, we have recruited across 14 countries; and have embarked on our global expansion plans with offices in Hong Kong and London this year, and US, Japan and Europe in the following years.

Space Ventures provides funding, management and financial guidance to young businesses with original ideas. We have invested in peer to peer lending platforms, credit scoring, social media education, and other start-ups spanning diverse industries. We are always interested in hearing more about new ideas.

How can people connect with you?
https://www.linkedin.com/in/agnesyee/

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:
twitter.com/laingcallum
linkedin.com/in/callumlaing
Download free copies of his books here: www.callumlaing.com

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