9 successful entrepreneurs share their best career advice

Coffee meeting friendsShutterstockSurprisingly, ‘drink a lot of coffee,’ didn’t make the cut

When Chris LoPresti decided that he wanted to launch a startup, the first thing he did was reach out to a bunch of other Yale alumni entrepreneurs for advice.

To his surprise, he recieved a veritable flood of tips, tricks, and words of wisdom.

LoPresti gathered all the suggestions together to publish a book called “Insights,” for which he’s donating all proceeds to other young entrepreneurs.

We got permission to publish some illustrations and excerpts from the guide here.

Check it out:


'Early on in your career, put yourself in situations where you are the dumbest guy in a room of experts or star performers,' Ning Liang, who cofounded HealthSherpa says. 'Then, drop your ego, work hard, and learn from your superiors. Repeat this with a few different fields of sufficient diversity and you'll be in great shape to start a company.'


'Starting a business worth starting is inevitably going to be a long hike, so you better find a way to enjoy it,' says Jordan Silbert, who founded Q Drinks. 'In fact, make having a good time a high priority for you and your team. I've learned that one of the biggest risks you face as an entrepreneur is giving up because the struggle is not worth it -- everything is going to be harder and take longer than you expect when you're starting out. But if you're willing to push on long enough, you will usually win. So figure out a way to make it fun.'


Here's some advice from Casey Gerald, who cofounded MBAs Across America:

'The first Christians stole half of a book from Judaism. The founding fathers stole ideas from the British, the Romans, and Enlightenment philosophers. Even The Beatles stole! If it was good enough for Jesus, George Washington, and Paul McCartney, it's good enough for you. As you try to make something out of your great idea and kickass team, don't waste time trying to reinvent the wheel. Use the wheels that already exist and invent something else. Austin Kleon's book, 'Steal Like an Artist,' is a great guide to stealing in the most productive, ethical way possible.'


'As a first-time entrepreneur, you have to realise from the start that you do not have all the answers,' says Justin Borgman, founder and CEO of Hadapt. 'In fact, you do not even know the right questions to ask most of the time. But that is all ok because this is going to be an incredible learning experience. If you approach the company-building process with this attitude, you are going to be more willing to acknowledge your mistakes as they occur and treat them as valuable lessons rather than failures. Believe me, there will be many of these 'lessons' along the way.'


Sander Daniels, cofounder of Thumbtack, never planned on being an entrepreneur. But when two friends decided to start a company, they asked him to join. To do it, he would have to drop his cushy law job and move with his wife and child to San Francisco.

Here's why he was happy he made the leap:

'I was very close to missing out on this opportunity. However, the last-second decision to jump at it opened a whole world of professional fulfillment that I didn't realise existed. I wish I hadn't been so conservative in my early career decisions and had jumped at this opportunity sooner. I didn't realise the intangible benefits of taking risks, and finally doing so has transformed my entire life -- personally and professionally -- for the better. Seizing the opportunity to help start a company is one of the best decisions I have ever made.'


'It's almost impossible not to shake your reflexive snobbery, your hard-won expectation that everything you touch will be gilded and glamorous,' TV writer and producer Rob Long says. 'But building something -- whether a television show, a business, or an iPhone app -- takes a certain amount of grubby ambition. It takes humility. It takes a willingness to do something that sounds unfancy and unglamorous and risk the most status-killing thing of them all: failure. In any endeavour, it's not failure you should fear. It's snobbery.'


'It's this simple: make a list of a few dozen people you want to meet, and send them an earnest and genuine email asking for their advice,' says Thumbtack cofounder Jonahtan Swanson. 'Repeat -- forever. Some people will ignore your email, but you will be surprised by how many very prominent people will respond and be willing to help. Be diligent about sending thank you emails, following up with updates, and reconnecting when the time is right. Be genuine, and offer to help them whenever you can. Some conversations will be dead ends, but many will be fruitful. Some won't show dividends immediately, but will prove valuable months or years later. Rand Fishkin calls this practice 'manufacturing serendipity.''


'If you want to be very successful in your chosen career, you want to ask yourself every morning, 'What can I accomplish today to help me move closer to reaching my goals?'' Sharper Image founder Richard Thalheimer says. 'If you don't do anything that particular day to move closer to your goals -- however small an accomplishment it may be -- then you have effectively wasted that day. You really did not accomplish anything that day, in terms of your entrepreneurial goals.'


The cofounder and CEO of Whistle says that the best founders act on intuition rather than emotion:

'At any small and growing company, you have to make decisions quickly and with incomplete information. Small business owners and technology entrepreneurs often talk about 'gut' or 'hunch' that guided them down a certain path during pivotal points for the organisation. As a younger CEO, this particularly feels like the case. But it's important to distinguish that feeling from fact-based hypotheses. If you make decisions based purely on emotion -- whether negative ones like fear, anger, disappointment, or positive ones like excitement, joy, even love -- your decisions will be entirely gut, and you'll often overreact or over-adjust in a moment of crisis.'

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