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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

Benjamin Kwan, Co-Founder of TravelClef

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Making music to create a life for his family, Benjamin Kwan, started an online tuition portal and his music business grew from there.

What’s your story?
I am Benjamin and I’m the Co-Founder of TravelClef Group Pte Ltd, a travelling music school that conducts music classes in companies as well as team building with music programmes. We also run an online educational platform which matches private students to freelance music teachers. We also manufacture our own instruments. I started this company in 2011 when I was still a freshman at NUS, majoring in Mechanical Engineering.

I was born to a lower income family, my father drove a taxi and was the sole breadwinner to a family of 7. I have always dreamed of becoming rich so that I could lessen the burden placed on my father and give my family a good life.

After working really hard in my first semester at NUS, my results didn’t reflect the hard work and effort I put in. At the same time, I was left with just $42 in my bank account and it suddenly dawned on me that if I were to graduate with mediocre results, I would probably end up with a mediocre salary as well. I knew I had to do something to gain control of my future.

During that summer break, I read a book “Internet Riches” by Scott Fox and I knew that the only way I could ever start my own business with my last $42 would be to start an online business. That was how our online tuition portal started and after taking 4 days to learn Photoshop and website building on my own, I started the business.

What excites you most about your industry?
Music itself is a constant form of excitement to me as I have always been an avid lover of music. As one of the world’s first travelling music schools, we are always very eager and excited to find innovative ways to a very traditional business model of a music teaching.

What’s your connection to Asia?
I was born and raised in Singapore and I love the fact that despite our diversity in culture, there’s always a common language that we share, music.

Favourite city in Asia for business and why?
Hands down, SINGAPORE! Although we are currently in talks to expand to other regions within Asia, Singapore is the best place for business. I have had friends asking me if they should consider venturing into entrepreneurship in Singapore, my answer is always a big fat YES! There’s a low barrier of entry, and most importantly, the government is very supportive of entrepreneurship.

What’s the best piece of advice you ever received?
I have been blessed by many people and mentors who constantly give me great advice but right now, I would say the best piece of advice that I received would be from Dr Patrick Liew who said, “Work on the business, not in it.” This advice is constantly ringing in my head as I work towards scaling the business.

Who inspires you?
My dad. My dad has always been my inspiration in life, for the amount of sacrifices that he has made for the family and the love he has for us. He was the umbrella for all the storms that my family faced and we were always safe in his shelter. Although my dad passed away after a brief fight with colorectal cancer, the lessons that he imparted to me were very valuable as I build my own family and business.

What have you just learnt recently that blew you away?
You can not buy time, but you can spend money to save time! With this realisation, I was willing to allow myself to spend some money, in order to save more time. Like taking Grab/Uber to shuttle around instead of spending time travelling on public transport. While I spend more money on travelling, I save a lot more time! This doesn’t mean that I spend lavishly and extravagantly, I am still generally prudent with my money.

If you had your time again, what would you do differently?
I would have taken more time to spend with my family and especially my father. While it is important to focus our time to build our businesses, we should always try our best to allocate family time. Because as an entrepreneur, there is no such thing as “after I finish my work,” because our work is never finished. If our work finishes, the business is also finished. But our time with our family is always limited and no matter how much money and how many successes we achieve, we can never use it to trade back the time we have with our family.

How do you unwind?
I am a very simple man. I enjoy TV time with my wife and a simple dinner with my family and friends.

Favourite Asian destination for relaxation? Why?
Batam, it’s close to Singapore and there’s really nothing much to do except for massages and a relaxing resort life. If I travel to other countries for shopping or sightseeing, I am constantly thinking of business and how I can possibly expand to the country I am visiting. But while relaxing at the beach or at a massage, I tend to allow myself to drift into emptiness and just clear my mind of any thoughts.

Everyone in business should read this book:
Work The System, by Sam Carpenter. This book teaches entrepreneurs the importance of creating systems and how to leverage on systems to improve productivity and create more time.

Shameless plug for your business:
If you are looking for a team building programme that your colleagues will enjoy and your bosses will be happy with, you have to consider our programmes at TravelClef! While our programmes are guaranteed fun and engaging, it is also equipped with many team building deliverables and organizational skills.

How can people connect with you?
My email is [email protected] and I am very active on Facebook as well!
https://www.facebook.com/benjamin.christian.kwan

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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Entrepreneurship

Before you enter a Startup or before you choose your founding team or new hires read, “Entering Startupland” by Jeff Bussgang

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Before you enter a Startup or before you choose your founding team or new hires read “Entering Startupland” by Jeff Bussgang.

Jeff knows how to spot and groom good culture, as the book session was held in Zestfinance a company he invested in and now, “The Best Workplaces for Women” and for “The Best Workplaces for Tech”, by Fortune.

These are the questions during the Book Launch.

How to know if a hire including the founder is Startup material?
Jeff says to watch for these qualities.

First, do the hires think like an owner?
Second, do the hires test the limits, to see how things can it be done better?
Are they problem solvers and are biased toward action?
Do they like managing uncertainty and being comfortable with uncertainty? And comfortable with rapid decision-making?
Are they comfortable with flexible enough to take in a series of undefined roles and task?

How do we know if we are simply too corporate to be startup?

Corporate mindsets more interested in going deep into a particular functional area? These corporate beings are more comfortable with clear and distinct lines of responsibility, control, and communication? They are more hesitant or unable to put in the extra effort because “it’s not my job”.

If you do still want to enter a startup despite the very small gains at the onset, Jeff offers a few key considerations on how to pick a right one.

He suggests you pick a city as each city has a different ecosystems stakeholders and funding sources and market strengths. You have to invest in the ecosystem and this is your due diligence. Understand it so you can find the best match when it arises.
Next, to pick a domain, research and solidify your understanding with every informational interview and discussion you begin. Then, pick a stage you are willing to enter at. They are usually 1)in the Jungle, 2) the Dirt Road or 3) the Highway. The Jungle has 1-50 staff and no clear path with distractions everywhere and very tough conditions. The Dirt Road gets clearer but is definitely bumpy and windy. Well the Highway speaks for itself, doesn’t it?

Finally Please – Pick a winner!

Ask people on the inside – the Venture Capitalists, the lawyers, the recruiters and evaluate the team quality like any venture capitalists would. Would you want to work for the team again and again? And is the startup working in a massive market? Is there a clear recurring business model?

After you have picked a winning team and product, how would you get in through the door?

You need to know that warm introductions have to be done. That’s the way to get their attention. Startups value relationships and people as they need social capital to grow. If you have little experience or seemingly irrelevant experience, go bearing a gift. Jeff shared a story of a young ambitious and bright candidate with no tech experience who went and did a thorough customer survey of the users of the startup she intended to work with. She came with point-of-view and presented her findings, and they found in her, what they needed at that stage. She became their Director of Growth. Go in with the philosophy of adding value-add you can get any job you want.

And as any true advisor would do, Jeff did not mince his words, when he reminded the audience that, “If you can’t get introduced you may not be resourceful enough to be in startup.”

Startupland is not a Traditional Career or Learning Cycles

Remember to see your career stage as a runs of 5 years, 8 or 10 – it is not a life long career. In Startup land consider each startup as a single career for you.

Douglas Merrill, founder of Zestfinance added from his hard-earned experience that retention is a challenge. Startup Leaders to keep your people, do help them with the quick learning cycles. Essentially from Jungle to Dirt road, the transition can be rapid and so each communication model that starts and exists, gets changed quickly. Every twelve months, the communication model will have no choice but to break down and you have to reinvent the communication model. Be ready as a founder and be ready as a member of the startup.

Another suggestion was to have no titles for first two years. So that everyone was hands-on and also able to move as one entity.

Effective Startupland Leaders paint a Vision of the Future yet unseen.

What I really enjoyed and resonated with as a coach and psychologist was how Douglas at the 10th hire thought very carefully what he was promising each of his new team member. He was reminded that startups die at their 10th and their 100th hires. He took some mindful down time and reflected. He then wrote a story for each person in his own team and literally wrote out what the company would look like and their individual part in it. In He writing each of the team members’ stories into his vision and giving each person this story, it was a powerful communication piece. He definitely increased the touch points and communication here is the effective startup’s leverage.

Douglas and Jeff both suggested transparency from the onset.

If you think like an owner and if you think of your founding team as problem solvers. Then getting transparent about financials with your team is probably a good idea. As a member of a startup, you should insist on knowing these things
Such skills and domain knowledge will be valuable. There is now historical evidence of people leaving startups and being a successful founder themselves because they were in the financial trenches in their initial startup. Think Paypal and Facebook Mafia.

What drives people to enter a startup?

The whole nature of work is changing. Many are ready to pay to learn. Daniel Pink’s book Drive showed how people are motivated by certain qualities like Mastery, Autonomy and Where your work fits into big picture. Startups do that naturally. There is a huge amount of passion and the quality of team today and as it grows then the quality of company changes.

The Progress principle is in place, why people love their startup jobs is not money rather are my contributions being valued? Do I see a path of progress and do I have autonomy over work and am I treated well?

Find out more about StartupLand on Amazon

And learn from Zestfinance

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