7 min read
woman teaching a lesson

13 Lessons From the Experiences of Self-Made Billionaire Founders

Startup founders and CEOs face many challenges: raising venture capital, building a founding team, developing products that can survive a competitive marketplace, getting their name out there, and more. It’s no surprise that the prospect of launching and surviving in the competitive world of startups can be daunting. 

But it’s not impossible. There are shining stars — unicorn leaders, if you will — that seem to get it right. Of course, their success didn’t come without trials and tribulations, but it can appear that way on the surface. We’ve turned to a cohort of self-made billionaire startup founders to gather advice and lessons based on their years of experience in the startup world. 

If you’re a startup founder that’s looking for advice on how to build your team of directors and officers or maybe you’re still in the ideation stage as an entrepreneur, here are 13 lessons from iconic startup leaders to point you in the right direction.

1. Stick to your mission. 

Elon Musk has stood behind his mission of “accelerating the advent of sustainable transport and energy” at all costs. This has been the case even when it’s meant announcing layoffs and other abrupt shifts for the good of the company. And while some of his choices as CEO have been criticized, there’s nothing quite like his relentless pursuit of developing technology that best serves humanity.

Not only is his loyalty to the company mission an excellent lesson for entrepreneurs, but it’s also a large component of what’s helped him achieve icon status among the Millennial generation — they value his positions on renewable energy and investments in the future of the world. Simply put, this has helped him earn loyal followers who appreciate his dedication.

elon musk lessons

2. Choose sustainability and quality over superficial battles. 

When you’re on the path to success, it’s easy for others to compare you to competitors. Instead of struggling to keep up with “outsider” impressions of what your company should be, remember your priorities.

With Xiaomi competing against tech giants like Apple and Samsung, they’re expected to grow fast. Founder Lei Jun believes that’s not sustainable, reminding the public that Xiaomi is only a five-year-old startup. Instead of pressuring his team to grow at a rate that’s not right for his company, he remains grounded to his vision of what Xiaomi should be — an electronics company that produces products that wow people. 

Lei Jun advice

3. Entrepreneurship is about becoming a problem solver. 

Solving for an existing problem is at the core of many startup stories on this list, but specifically that of Jan Koum and WhatsApp. Back in 2009, Koum and co-founder, Brian Acton came up with the cross-platform messaging service purely out of necessity — so they could stop missing calls on their smartphones.

They didn’t actually set out to build a company, rather an app that could let their friends know whether or not they were available, thanks to an easy-to-use feature called “Status.” But as it happens with great ideas, WhatsApp caught the attention of users and investors to become a preferred communication tool for business and personal users across the globe.

jan koum advice

4. Perfection is a never-ending process.

While DJI dominates the consumer drone industry, its founder and the world’s first drone billionaire Frank Wang is a long way from reaching his desired level of perfection. Wang brings to the table a sense of Japanese craftsman mentality — constantly striving for perfection. 

The 35-year-old drone overlord will be the first to tell you that DJI is a long way from reaching “perfection” and always looking for ways to improve their products. It should come as no surprise that DJI is a consumer’s choice for those who wish to be sky pilots. 

frank wang advice

5. Be decisive in cutting toxic staff.

Jack Dorsey, founder and acting CEO of Twitter and Square, admits one of his early weaknesses was being too slow to move out toxic staff who had a negative impact on the business and culture. After all, business is largely about the quality of its people.

Regardless, it’s true that one of the most notorious companies in the world has the same problem as any other company: human resources. Dorsey’s suggestion is to be decisive when removing toxic employees — the remaining team will rise to the challenge and fill in any gaps.

jack dorsey advice

6. When you make mistakes, own them and apologize. 

If Silicon Valley had a bad boy icon, it would be Evan Spiegel, the founder of Snapchat. While he’s earned quite a reputation from Snapchat’s success, he’s not without fault. 

In 2014 Valleywag leaked a series of emails from Spiegel’s college days. The NSFW conversations between him and his fraternity brothers included a slew of misogynistic jokes and anecdotes that circulated quickly, showing a side of him that most would consider sexist, racist, and homophobic. In response, Spiegel issued an apology expressing his remorse for the emails. 

While you can’t undo mistakes, apologizing and owning them publicly is always the most responsible course of action.

evan spiegel advice

7. Be prepared to bootstrap marketing strategies.

Today, Airbnb is a common household name, but back in 2008, the startup was struggling to get enough visibility to attract capital. Broke and in debt, Brian Chesky, Nathan Blecharczyk, and Joe Gebbia decided to launch Air Bed & Breakfast (again) during the Democratic National Convention in Denver — this time armed with a bootstrapped marketing strategy.

The team transformed cereal boxes into Obama O’s and Cap’n McCains and sold them on the streets for $40 bucks a pop. Each one came with a limited-edition number and information about the company. Their bootstrapped marketing strategy netted them $30,000 to put toward the company.

brian chesky advice

8. Meet your users where they are.

In its early stages, Dropbox was a cloud sharing service that people didn’t know they needed. So, in an effort to boost growth, founders Drew Houston and Arash Ferdowski created awareness by sharing the startup on sites like Digg and Reddit — these became huge sources of traffic and a way to grow interest in the company.

Their remarkable growth hacking video titled “Google Drive killer coming from MIT startup” got 1,506 Reddit upvotes and 12,000 Diggs, which catapulted it to the first page. In turn, this jumped the beta waiting list from 5,000 to 75,000 overnight — solving the company’s “getting started” problem.

drew houston quote

9. Not all founders can take their company to the next level.

Travis Kalanick, founder of Uber, is no doubt a visionary that transformed the taxicab/ride-hailing transportation business. That said, an entrepreneur with a great idea is not always the individual with the skills, values, and temperament to run and grow the company in the long run. 

Kalanick was ousted as CEO in the summer of 2017 for numerous ethical and moral reasons. In short, if the founder CEO isn’t cutting it regarding tone, ethics, and culture, make a change before change is forced upon you by the company’s investors.

travis kalanick

10. Build a legacy through succession planning. 

Few people stay in the same job forever — even company founders. Regardless of whether you hope to sell your company or plan on maintaining your role until you retire, you undoubtedly want it to succeed after you’re gone. 

Establishing a succession plan is a way to ensure that your organization is ready to build on your foundation by finding a qualified individual to take your place. Billionaire Danish entrepreneur, Janus Friis, is one such example. As a serial entrepreneur with numerous tech ventures to his name, he knows a thing or two about building management teams that will take care of things in their absence. 

janus friis quote

11. Lead by example.

This may come as an obvious lesson, but leading by example is just as important for building a solid foundation as any other lesson on this list. One such founder, Cheng Wei of Didi Chuxing, the billion-dollar mobile transportation platform, is devoted to this strategy.

Cheng Wei’s ideas often align with military analogies. As he wrote in a personal blog, “Training alone won’t make employees grow up.” He’s also been known for referencing speeches on leadership from executives such as Alibaba founder Jack Ma, Baidu’s Robin Li, and Microsoft’s Bill Gates — all lessons he’s used in his delegation of powers at Didi.

Cheng Wei quote

12. Surround yourself with talent, even if you don’t have a defined role for them yet.

One upon a time, Pinterest was an invite-only community — even its first users were design bloggers recruited by founder Ben Silbermann. He advised these invitees to only extend admission to people they knew with unique ideas and creative minds. 

Of course, as the company grew, the invitation requirement was removed from the site. But Silbermann continued to build the company with people who were uniquely talented and creative — bringing them on board for their strengths, even if he didn’t have an immediate role for them. Those key hires infused the company with innovative thinking and repeatedly found solutions to problems that seemed unsolvable.

ben silbermann quote

13. Success can come at any age.

The founders of Stripe, John and Patrick Collison, grew up in a small village in central Ireland, teaching themselves to code at a young age and competing with each other. Patrick graduated from high school at 16 and enrolled at MIT. His brother John followed him to the US a few years later, enrolling at Harvard. 

They both dropped out of college in 2009 to head to Silicon Valley to start what would become Stripe. Fast forward to 2018 and John Collison became the world’s youngest self-made billionaire at 27, proving that success can come at any age.

john collison quote

download infographic button

In today’s competitive startup world, founders must always look for ways to improve their company (both internally and externally) if they want to take things to the next level. 

Whether you’re learning how to navigate the complex ecosystem of venture capital funding or you’re looking to cover your business with the right insurance policy, there’s a lot to consider. Embroker can help you check those boxes and make sure you safely navigate the ins and outs of startup insurance along the way.