Entrepreneurs

Why Steve Jobs and Other Leaders Maintained An Underdog Attitude After StartUp Success


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Scrappiness has come to define . Startups adopt a relentless and dogged approach to growth that takes setbacks and churns them into successes. As I’ve seen from my own humble small beginnings, this kind of culture has come to mean more than that for companies looking to scale.

With 56 percent of employees valuing workplace culture over salary, a scrappy atmosphere could mean the difference between a beginning business that fades into obscurity and one that evolves to meet the challenges of tomorrow.

There’s possibility in adversity

A tough culture is critically important to constructing a that can go the distance. Employees that experience the benefits of a scrappy culture will be more motivated to contribute to a startup’s early growth period and that environment will cultivate a go-getter attitude that multiplies over time.

On the flip side, a toxic culture can gradually eat away at a startup’s trajectory. According to one study, 72 percent of employees said corporate culture influences where they choose to work.

That’s why startups can — and should — maintain that vibe, even as they continue to scale. Scrappiness is about keeping an underdog mentality (and we all know how much humans love Cinderella stories). People routinely vote for underdog candidates and support them in sports because they relate to the challenger. This mentality makes the excitement of the chase more significant and ends up making the eventual victory feel that much better.

Related: Winners Know It’s Always Better to Be the Underdog

I’ve seen firsthand how entrepreneurs can benefit from staying scrappier for longer. The companies I’ve worked with that have maintained this culture manage to appear more authentic to their audiences by stoking this mentality and their employees’ loyalty. A “never satisfied” mentality can help drive your small company over the top.

Keep the chip on your shoulder

A scrappy culture is easier to create at the outset of startup life, when the team is manageable and everyone’s back is against the wall. But the key to scaling successfully is finding ways to maintain this attitude at every stage of your company’s life.

Here are three strategies to deploy, even when you’re moving up in the world.

1. Offer employees their own stake

Encouraging employees to take on new challenges, create new efficiencies and take ownership of their processes is a great way to keep your team motivated.

Certain kinds of leadership can be detrimental to this sense of ownership and the that comes from it. Micromanaging, for example, can make employees feel helpless and uncreative. During his first stint with , was a notorious micromanager. But when he returned to the helm in 1997, Jobs flipped that mentality by adopting a startup mindset that encouraged employees to act without input from higher-ups.

Create a workplace atmosphere in which creativity and autonomy are celebrated. Tear down silos and snip red tape so your team feels empowered to act and push the company forward.
Related: How to Strike a Balance Between Micromanaging and Under-Managing

2. Don’t shy away from details

Young companies need to manage their expenses carefully because they’re not yet making a profit. Before ShipMonk grew enough to open our headquarters, critical team members — including myself and our chief revenue officer — personally laid down epoxy flooring throughout our office.

We didn’t need to rely on outside contractors. Staying consistent with our bootstrapped origins, we took matters into our own hands and laid the floor ourselves. Who’s to say you can’t keep this mentality as you scale? Just because you’re growing the team and achieving more significant projects doesn’t mean you have to invest in a vast office space or outsource all the handiwork to others.

Think about how you can reuse or re-purpose existing resources to keep your costs low and ambitions high. Encourage current staff to keep an eye out for promising talent, giving them the freedom to find ways to modify and improve existing resources and practices.

For example, perhaps you could reshuffle your existing space to make it more relaxing rather than moving to an office with a nap room? Do recruiting practices and internal policies need to be revisited? Empower your team to tackle internal tasks themselves.

Related: 8 Bulletproof Ways to Bootstrap Your Business

3. Give people their flowers

In the early days of any up-and-coming enterprise, the lows are low — but the highs are exceptionally high. There’s reason to celebrate whenever you make a sale, sign a contract or notice a spike in website traffic. At this time, employees are more likely to feel motivated and rewarded, which keeps them striving toward more.

When the initial buzz wears off, this inspiration can be hard to find. Keep the party going by celebrating large and small wins regularly. According to a SurveyMonkey study, 82 percent of employees are happier when their companies recognize their efforts.

We regularly treat our employees to company outings and activities. We recently rewarded our sales and marketing teams for their work with a team dinner and an ax-throwing outing. This isn’t just a vague morale boost; research shows that celebrating achievement is strongly linked to employee retention.

This is the attitude you need to succeed at any business stage, but it can be particularly valuable as you reach the tricky scaling phase. If you want employees to keep hustling, help them feel ownership over their work and see that they’re making an impact — do so by encouraging their inner scrappers.

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