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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

Mikyung Kim, TV Commercial Producer

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Mikyung Kim is a savvy producer who runs her own TV and print production business, based in Hong Kong.

What’s your story?
I am a TV commercial and print producer working with advertising agencies and brands to bring their communication needs to the screen. My background is in film production and I started my career in Hollywood working with Oscar winning directors Michel Gondry and Alejandro González Iñárritu. Before starting my own company last year to produce content directly with agencies and brands, I was with Ogilvy & Mather Hong Kong for nearly five years as the Senior Producer and Head of TV running the film production department.

What excites you most about your industry?
How it’s constantly evolving! Every day is different and it’s certainly never boring. I love that it’s a creative industry and that my job involves talking to people with creative minds on how we can bring a story on paper to life. It’s exciting that the advertising industry places high value on the creativity and effectiveness of content. I’ve produced a few commercials that creatively push the envelope with fun and sometimes wild ideas that have converted into positive brand awareness. Ever heard of KFC Finger Lickin’ Good…Nail Polish that yes, tastes like chicken? https://www.adweek.com/creativity/kfc-just-made-edible-finger-lickin-good-nail-polish-yeah-tastes-chicken-171245/

What’s your connection to Asia?
I was born in Seoul and raised in Hong Kong until graduating from high school at HKIS. I spent my university years in Boston at Emerson College and worked in Los Angeles at Anonymous Content and Partizan Entertainment. But on a brief visit back to Hong Kong in 2010, I decided to move back and continue my career here, and it was the best decision I ever made.

Favourite city in Asia for business and why?
Hong Kong is my home so it will always be my favourite city for business and for me personally. What I love about Hong Kong is that while I am based here, I can actually work with agencies and brands from anywhere in APAC. If I need to attend an important meeting, I can just hop on a quick flight easily. I spent most of 2017 working in Seoul with Korean agency Cheil and Samsung, and currently I am working with Japanese agency ADK and Toyota based in Singapore.

What’s the best piece of advice you ever received?
“Fake it until you become it,” from Amy Cuddy’s TED talk. Worth a watch. This helped me early in my career when I felt like I was under qualified for the job I was in. I learned to fake my confidence and fake a powerful body language until I truly felt that confidence became something real. It was nerve wracking at first but it worked and now I don’t have to fake it.

Who inspires you?
My friends. Noelle who worked part time jobs while being a full time student to pay her own tuition while we were in college together. Osti who is a lawyer focused on supporting developing nations and a board member of Redress, an environmental NGO working to reduce waste in the fashion industry. Vanessa who runs a real estate company, co-owns the gym Crossfit Asphodel, started a health foods business called Quo and NGO The Keep Moving Project to promote wellness in our community. Cathy who will be the first Asian woman to direct a big budget superhero film starring Margot Robbie with Warner Bros and DC. And too many more to name!

What have you just learnt recently that blew you away?
5.2 million plastic bottles are thrown away in Hong Kong every day. Plastic pollution is a major issue for the environment and we as responsible citizens can do our small part by reducing our consumption of unnecessary plastic. I do mine by having a water filter at home and carrying my own reusable water bottle with me everywhere I go. I love the brand Hydroflask because the stainless steel material keeps water hot or cold for hours, so I don’t feel tempted to buy a cold water at 7-11 on those hot, humid days we have here.

If you had your time again, what would you do differently?
About five years ago I purchased my very first stock and put one month’s salary into it, which at the time was a lot of money for me. Knowing how that stock has performed now, I would have put all my savings into it.

How do you unwind?
Exercise is essential in my daily life to help clear my head and de-stress. My go to is a workout at Crossfit Asphodel, running outdoors, yoga and hiking. But a glass of red wine and live music at Soiree in Soho on Sunday night works pretty well too!

Favourite Asian destination for relaxation? Why?
One of the best trips I ever took was to the island of Lombok in Indonesia. Two girl friends and I did a 3 day 2 night hiking and camping trip to summit the Mount Rinjani Volcano. It was physically challenging but mentally relaxing. There was no cellphone reception, no distractions, we had the company of nature and nights with skies full of shooting stars. It was pretty magical. We then went to the Gili Islands for a few days of scuba diving, yoga and sitting on the beach doing nothing but sipping on coconuts. That was pretty relaxing too.

Everyone in business should read this book:
“Nice Girls Don’t Get the Corner Office” by Lois P. Frankel and “Lean In” by Sheryl Sandberg. Essential reads for every working woman and/or man who wants to know how to support the working women in their life.

Shameless plug for your business:
I am a TV commercial and print producer that can plug into an existing advertising agency or brand team to produce their communication needs. Many advertising agencies these days are scaling down so they have creative directors and account services but may not have an in-house producer, so I can fill that gap by becoming a part of the existing agency team. For brands that want to produce content directly without involving an agency, I can also bridge the gap by bringing my production knowledge in-house and working as part of the marketing/brand team and liaising with the other departments in the company such as product team and ecomm.

How can people connect with you?
They can email me at [email protected]
or visit my website at mkimproducer.com

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

Renne Ballard, Owner of Renée Ballard Communications

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Renne Ballard runs a social media agency working with business women, helping them find their business’s voice.

What’s your story?
I began my career in PR/communications ten years ago in Australia, after arriving home from two years in Dubai. In Dubai I was working for Emirates Airlines as a flight attendant and flying around the world non-stop for two years. This really sparked my interest for how people communicate. I started out as a community manager for an online advertising company, then moved into the corporate world of outdoor advertising, managing internal and external PR and communications. After having a baby four years ago, I decided to leave the safety net of corporate, and stride out on my own. I now run a social media agency and I specialise in working with business women, helping to find their business’ voice so they can use social media to achieve their business goals.

What excites you most about your industry?
I love the open accessibility online provides. It’s free for businesses to get online and connect with their target audience. Twenty years ago, advertising and PR was insanely expensive and quite elitist, but through incredible platforms like Facebook or Twitter, any business can connect with who is looking for their product/solution. Social media is particularly effective for small businesses because they have the edge when it comes to authenticity and a clear voice.

What’s your connection to Asia?
I’m in Hong Kong because I’m a trailing spouse. I know it’s such a daggy term, but I love it, it makes me sound so dedicated to my husband! Alas, we came to Hong Kong for my husband’s work. He’s the Design Director of Asia for an international retail design agency. We’ve been here for almost two years and it’s been a huge learning curve in terms of business and culture. We love the fast-paced nature of Hong Kong and the fact that everything is open late – it suits me perfectly because I’m nocturnal.

Favourite city in Asia for business and why?
That’s easy, Hong Kong. It’s the perfect blend of start-ups and mothership-sized institutions. I love the small business side, watching the collaborations between workshare spaces with galleries, networking groups and foodies; it’s a hothouse of creative partnerships here.

What’s the best piece of advice you ever received?
When you’re are feeling scared about your next step, lean in and feel the difference. Is it fear mixed with excitement? Or fear mixed with dread? Always go with the former and cut loose the latter.

Who inspires you?
I love Tamara Mellon (Jimmy Choo founder). She has created multiple empires and she never stops trying new business models and pushing her limits. It helps that I love shoes too.

What have you just learnt recently that blew you away?
I just turned 40 years old. At best, I’m probably halfway through my life. It makes me constantly question, “Am I where I want to be?”

If you had your time again, what would you do differently?
I would have asked more questions to the people I looked up to, and listened less to the people telling me I won’t achieve my goals.

How do you unwind?
In this day and age, it’s scandalous to say, but I love sunbaking. At any chance, you’ll find me poolside, laying in the sun in a trance-like state.

Favourite Asian destination for relaxation? Why?
Northern Danang in Vietnam. We were there at Christmas, at the foot of the mountains and it was beautiful. Heaps of wildlife and jungles and enough five star resorts that I was never parched once.

Everyone in business should read this book:
‘The E Myth’ by Michael Gerber. It’s an oldie but a goodie because it succinctly outlines how to transition from a one person operation to a global business like McDonalds. Once you see how important systems and processes are, you can recognise shambolic companies a mile off.

Shameless plug for your business:
Renée Ballard Communications is a social media agency that works with business women who are ready to make social media work for them. We create effective, powerful social media strategies that are tailored to the people who will be breathing life into them. We hand on heart promise to never use annoying, marketing buzzwords and that we value laughter above everything else.

How can people connect with you?
[email protected] or www.reneeballard.com or +85296670115

Twitter handle?
@ballard_comms

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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