Business
Think Working 14-Hour Days Sets a Good Example? This CFO Says It’s Actually a ‘Terrible’ One.
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Published 10/21/2026 10:17:24 AM
CFO of $157B Company Says Not to Work 14-Hour Days
Key Takeaways
- Gina Mastantuono, president and CFO of software company ServiceNow, says CFOs can learn from how elite athletes approach their jobs.
- She said performing at a high level means making time for recovery, not just pushing harder.
- Her message challenges a stubborn corporate mindset that the more you work, the more committed you are.
Working long hours and barely sleeping sets a poor example for the people you lead, even though the habits still pass for dedication in the executive suite, says one CFO. You may see an impressive work ethic, but your employees may just see an implied, unwritten expectation to adopt the same unhealthy practices.
Gina Mastantuono, president and CFO of Fortune 500 software company ServiceNow, says CFOs can learn from how elite athletes approach their jobs. Performing at a high level means making time for recovery, not just pushing harder, she said. ServiceNow has a market capitalization of $157 billion.
Mastantuono shared her perspective at a Fortune event earlier this month, which brought leaders together in Santa Barbara, California. Joining her on the panel were Olympic championJanet Evans and Deloitte’s U.S. sports chief commercial officer and women’s sports leader Alicia Hatch.
Mastantuono said on the panel that she has championed fitness as a way to support both personal health and effective leadership. Her message challenges a stubborn corporate mindset that the more you work, the more committed you are.
“There’s always been this idea that if you have to work 14-hour days and get four hours of sleep, that shows you’re working the hardest and deserve the most,” she said. “That is such a terrible example for the people around us.”
Mastantuono said recovery is part of the work of performing well, not something to squeeze in when the hard work is over. The same idea that applies to physical exercise carries into the office: Workers all the way up to the C-suite have to balance pushing hard with time to recharge.
Learning from playing sports
Making time to recharge has changed how Mastantuono works and leads. She has achieved a healthier balance between her job and her personal life, become a more attentive listener and is able to stay calm under pressure. Her team benefits from that steadier approach too.
“When we do focus on taking care of ourselves, then we are much better bosses, much better colleagues, much better parents,” she said.
The parallels between sports and leadership don’t end with recovery. Athletes also practice making tough calls in real time and adjusting to unexpected situations.
Hatch asked the audience to consider how often they make consequential decisions without all of the facts and with “a lot of people watching.” “We face this every single day,” she said.
She pointed out that 94% of female C-suite executives played sports growing up. “There’s a reason for that,” she said. In her view, playing sports provides a rehearsal for the demands of leadership and hones the ability to make decisions under pressure.
Sports are “an amazing simulator” for “performing continuously, even with changing circumstances,” Hatch said.
Evans added that athletes learn to stay committed to a goal without getting locked into a single way of reaching it. That adaptability, paired with the willingness to take risks and push through setbacks, prepares them to pursue ambitious goals as leaders, she said.
Key Takeaways
- Gina Mastantuono, president and CFO of software company ServiceNow, says CFOs can learn from how elite athletes approach their jobs.
- She said performing at a high level means making time for recovery, not just pushing harder.
- Her message challenges a stubborn corporate mindset that the more you work, the more committed you are.
Working long hours and barely sleeping sets a poor example for the people you lead, even though the habits still pass for dedication in the executive suite, says one CFO. You may see an impressive work ethic, but your employees may just see an implied, unwritten expectation to adopt the same unhealthy practices.
Gina Mastantuono, president and CFO of Fortune 500 software company ServiceNow, says CFOs can learn from how elite athletes approach their jobs. Performing at a high level means making time for recovery, not just pushing harder, she said. ServiceNow has a market capitalization of $157 billion.
Mastantuono shared her perspective at a Fortune event earlier this month, which brought leaders together in Santa Barbara, California. Joining her on the panel were Olympic championJanet Evans and Deloitte’s U.S. sports chief commercial officer and women’s sports leader Alicia Hatch.
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- Joe Spector, 45, is the CEO of Dutch, an online veterinary care service.
- In a new interview, Spector shares how he went from living on food stamps to becoming CEO of his own startup.
- Spector also co-founded $9.3 billion telehealth startup Hims & Hers.
Joe Spector and his family immigrated to the United States from the former Soviet Union, now Uzbekistan, in 1990, when Spector was 10 years old. When they arrived in Fremont, California, the family lived in low-income housing and relied heavily on welfare and food stamps as they adjusted to their new life.
“Coming to America was like going to Mars,” Spector tells Entrepreneur. “It’s really a different planet.”
Basic things like culture and clothing were different, but Spector also noticed a difference in the classroom. In the Soviet Union, kids were told not to ask questions, but in the U.S., teachers encouraged students to ask questions and be curious.
“That alone highlights the freedoms that we have in this country,” Spector says.
Spector’s limited finances played a role in major life decisions, like deciding to finish college — which he was paying for himself — in three years instead of four.
After graduating from the University of California, Berkeley, with a degree in business in 2001, Spector moved to New York to work for JPMorgan as an investment banker. He ended up making over $200,000 in salary at just 25 years old.
“I made money to justify the sacrifice my parents made to come to America,” he says.
After five years at JPMorgan, Spector left to obtain his MBA at the University of Pennsylvania’s Wharton School of Business. It was in business school that he found a community of entrepreneurs, some of whom were also immigrants. “I think seeing that is the first time I truly realized that I could be an entrepreneur as well,” he says.
Related: She Moved to the U.S. at 17 and Worked at a Gas Station — Then Became CEO of a $1 Billion Brand
Spector graduated from Wharton in 2007 and spent the next decade in the San Francisco Bay Area building businesses, including a failed dating website, and working at various startups in sales and business development roles. He honed his network and his skills.
In 2017, Spector co-founded telemedicine company Hims & Hers, an over-the-counter prescription drug startup, now a publicly traded $9.3 billion company.Spector says his starting salary at the company was $150,000 in 2017, and he made $210,000 when it went public in January 2021.
His salary might seem below average for a fast-growing Silicon Valley startup, but Spector believed in the mission of Hims & Hers: to make healthcare more affordable.
“I think generally anything around healthcare affordability is meaningful to me, having grown up on welfare and food stamps when my family first came to the United States,” Spector says.
There was only one issue, and it wasn’t the salary or mission — Spector was senior vice president of strategic initiatives at Hims & Hers, not CEO. The chief executive title belonged to his co-founder, Andrew Dudum.
“Look, at Hims, I wasn’t the CEO,” Spector says. “Ultimately, I wanted to build a business with a point of view and intentionality on culture that I couldn’t have when I was at Hims.”
Spector decided to leave Hims & Hers in February 2021, one month after it became a publicly traded company. He had spent his whole career at early-stage companies, and says feeling like he was a “cog in a wheel” at a big public firm was unappealing.
Spector went on to found Dutch, a telehealth platform connecting pet owners to veterinarians for a single annual subscription fee. Spector’s decision to pursue Dutch came from personal experience. His family adopted a corgi named Eddie during the Covid-19 pandemic. Very quickly, the vet bills racked up — Eddie got into some trail mix, leading to a $2,000 urgent care vet visit.

From his experience building Hims & Hers, Spector predicted that pet healthcare could be more affordable, leading to his idea for Dutch, a platform that charges a flat fee for unlimited telehealth vet care. Dutch offers a year of care, with unlimited virtual calls with a veterinarian for up to five pets, for $132.
Spector launched Dutch in July 2021 after raising $5 million in seed funding from Forerunner Ventures. As CEO of Dutch, he now makes $280,000 a year, a step up from his salary at Hims & Hers. More importantly, he views his work at Dutch as a “more important calling” than what he was doing at previous companies.
“At Dutch, 50% of our clients report that they haven’t been to a vet in over three years,” Spector says. “It’s crazy. In terms of giving back, it’s a more incredible opportunity than anything else I’ve done.”
Related: His College Side Hustle Made $12,000 on Amazon in 2 Weeks — Then It Surpassed $250 Million
The startup has seen its revenue double year-over-year for the past three years and is now “almost profitable,” according to Spector. “We’re getting there,” he says.
Spector describes the most fulfilling aspect of building Dutch as the excitement and satisfaction of solving new challenges.
“I love being part of something new,” he says. “That’s the hardest part, but it’s also just the most professionally satisfying when you figure things out for the first time.”
Related: My Business Tapped Into a Misunderstood Market and Made $760,000 in Year 1§
Opinions expressed by Entrepreneur contributors are their own.
Key Takeaways
- Focus on these three things to successfully build a culture of curiosity.
I believe that a culture of curiosity pays dividends to not only any organization but also any relationship. In my work with my clients, especially when coaching co-founders and leadership teams, I see that nothing creates disconnection faster than an attachment to being right. There’s nothing wrong with pursuing the right answer or having conviction in a point of view, but the danger is when a point of view becomes connected to our own egos and identities. This is not the search for what is right, but rather an individual righteousness that flies in the face of truth.
Curiosity, on the other hand, fosters connection and builds up relationships. It creates space for innovation and creativity. It allows, still, for strong perspectives, but it creates the openness to evolve. It is the lifeblood of healthy, adaptable organizations.
So how, then, can we each take the responsibility to be curious, role modeling that for our teams and our peers? Three things have come into focus time and time again, three ways of helping to invite more curiosity into the workplace: staying present in the here and now, separating observation from imagination and letting go of binary thinking.
Related: A Culture of Curiosity Is the Key to Building a Company That Learns to Improve
Staying present in the here and now
I often say that “the past tense is the language of blame.” It’s incredibly hard to have a grounded, curious conversation when we’re pulling in stories and arguments from the past. The same goes for spending too much time in the future tense. Sure, we need to learn from past mistakes and plan for future considerations, but these conversations should be grounded in the present around what we can learn or what we can do now.
The risk of being too past-focused is that we end up arguing about our own versions of history and the he-said-she-said. The risk of being too future-focused is that we speak in hypotheticals, usually focused on our own supporting facts and data. Again, there’s nothing inherently wrong with looking to the past or future, but to foster curiosity, try staying in the here and now. Lean into your own present-focused statements around your beliefs and feelings.
Separating observation from imagination
An observation is anything that could be played back on a video recording. It doesn’t mean it’s 100% correct, as a lot of research into the accuracy of memory shows, but it is objective in nature. An imagination is any story or judgment that we make up about our observations. It’s inherently subjective in nature and grounded in our own assumptions.
It’s helpful to keep the distinction in mind and to categorize our thoughts into one of the two camps. The implication here is that, while we can be reasonably confident in our observations, we must create some space for curiosity when our imaginations make up a story. Even more powerful is to use this language in practice. Call out your observations and imaginations out loud — for example, “I saw your eyebrows raise when I shared my quarterly results, and I’m guessing that you’re surprised.”
Related: Cultivating Curiosity Is What Drives Innovation
Letting go of binary thinking
The risk of binary thinking, or thinking in black-and-white, absolute terms, is that we might oversimplify a complicated idea and miss other perspectives. I see this most often when it comes to receiving feedback. The natural human response, when we get a piece of feedback, is to ask “Is it true or not?” Implicitly, we’re putting the feedback into either the “true” bucket or the “false” bucket. In doing so, we’re missing out on the precision of asking “Which parts of this are true?”
The latter approach invites openness and learning, while the former does not. It can be difficult to spot binary thinking, as it’s an easy default for our thought processes. But anytime we can spot it, we create an opportunity to expand the conversation away from either/or and into curiosity.
There are many ways to foster more curiosity in our organizations and relationships, but start with trying to stay present in the here and now, separate observation from imagination, and let go of binary thinking. Importantly, these are all things that we can do ourselves. We can take ownership of creating the culture we want and invite others into it as a result. Start by choosing just one of these three ideas and, with it, one commitment or action that you can do each day for the next few weeks. See what happens, and build on what works.
Good luck on your journey.
Key Takeaways
- Focus on these three things to successfully build a culture of curiosity.
I believe that a culture of curiosity pays dividends to not only any organization but also any relationship. In my work with my clients, especially when coaching co-founders and leadership teams, I see that nothing creates disconnection faster than an attachment to being right. There’s nothing wrong with pursuing the right answer or having conviction in a point of view, but the danger is when a point of view becomes connected to our own egos and identities. This is not the search for what is right, but rather an individual righteousness that flies in the face of truth.
Curiosity, on the other hand, fosters connection and builds up relationships. It creates space for innovation and creativity. It allows, still, for strong perspectives, but it creates the openness to evolve. It is the lifeblood of healthy, adaptable organizations.
So how, then, can we each take the responsibility to be curious, role modeling that for our teams and our peers? Three things have come into focus time and time again, three ways of helping to invite more curiosity into the workplace: staying present in the here and now, separating observation from imagination and letting go of binary thinking.
§
Opinions expressed by Entrepreneur contributors are their own.
The following excerpt is from Scott Duffy‘s book Breakthrough. Buy it now from Amazon | Barnes & Noble | Apple Books | IndieBound
How do you inspire people to open their minds in a way that unlocks the creativity within your organization and achieves the best results? Let me share a story about how a former colleague in the advertising industry attained legendary status for his ability to unlock creativity (and have a great time in the process).
His goal was to change the way products were marketed in his client’s business. He wanted his team to think in entirely fresh ways about their jobs and change the way their product was viewed. To that end, he took the whole creative and account team to Las Vegas.
He told them almost nothing about the trip. The team arrived in Vegas, and for three days, he told his team, there was nothing on the agenda other than having fun. So they went out eating, drinking, gambling, clubbing.
Related: 7 Ways to Make Outsourcing a Success Time After Time
On day four, he gathered the group and told them, “We need to change the way products are marketed in this industry. We need to be creative, different, unique. We need to appeal to our client’s core young male audience — and they play lots of video games.”
While he was speaking, video game systems were being installed in team members’ rooms. For the next three days, he instructed, their job was to play video games. They were supposed to think about the whole experience of playing a game, including the graphics, the sounds, and the characters that appealed to the target audience. He wanted them to consider how game designers presented content, how they manipulated the look and feel of the product for the customer. He asked them to pay attention to the scoreboards, sound effects, and every other little trick the game designers had devised. Most of all, he wanted his team to think about how his client could build upon video game innovations to make their real-life products win over a new generation of customers.
After three glorious days in the sun, his team wasted no time in unleashing their creativity and changing the way people used their client’s products. In short, they came up with a unique look that separated them from everyone else in the industry.
Related: The 13 Factors That Make a Strong Partnership
Could his team have accomplished the same results playing games back in their New York offices? I doubt it. By taking his team to Las Vegas, he shifted them from work mode to play mode. He put people together who normally did not have much time to interact in a social setting. The days of partying in Las Vegas brought them closer, building camaraderie and a sense of teamwork. Two guys in a hotel room playing a video game see their jobs differently than they would if seated in adjacent offices at their computers.
I’m not saying you need to take your team to Vegas (or anywhere else) for six days. But to foster creative teamwork, you need to find a way to get them out of the office mindset and break down their natural resistance. You need to tap the genius within each of them on a regular basis. Being creative applies to all aspects of your business, from building something cool to breaking down barriers when trying to sell your product.
You can tap your employees’ creativity by following these recommendations:
Get groups together.
When you’re launching a new business or product, team members are busy. All of them have their heads down, focused on what they’re responsible for. Most of their time is spent working with other people in their department. The creative and technical people don’t get much time to interact. There are ways to change that.
At Xoom, we had pizza and beer at 3 p.m. every Friday. People from different groups got to interact in a social environment. As the company grew, those Friday afternoons offered an opportunity to meet new team members, and together we evolved a shared vision of the company. Even if people with different responsibilities looked at the company in different ways, over beer and pizza, we came up with some of our most creative — and collaborative — ideas.
Get out regularly.
Do something outside the office at least once a quarter. The activity doesn’t have to be expensive or extravagant. You might schedule a happy hour, miniature golf, or go-cart racing. Whatever it is, getting people to engage in a new setting can build relationships and inspire creativity. By gettingyour employees out of their comfort zones and getting them to interact with one another can open their eyes to new possibilities.
Related: Are These 5 Tasks Part of Your CEO Job Description?
Encourage experimentation.
Declare that for a few hours every month, no one’s allowed to use their computer or smartphone. In place of screens, issue every employee a notebook and ask them to spend the time writing, sketching, and diagramming their thoughts and ideas on how to improve and innovate the business. The novelty of putting pen to paper will force them to think in a different way. After the exercise, encourage them to tear pages out of their notebooks and post them on a brainstorming wall.
Encourage risk.
You win some, you lose some. But people need to be encouraged to take risks and be creative. They need to know that even if something doesn’t work, these experiences are all a valuable part of growing a business. One way to do this is to encourage your team to experiment with side projects. Many of these will fail, but odds are one of them may turn into your next big idea. And if they try something that doesn’t work, there’s no concern that it will put the entire operation — or the person’s job — at risk.
If something doesn’t work, still celebrate that your team took a shot.
People who are the most successful and creative are the ones who take risks. They try, they fail, and they learn from their mistakes. Create a culture where taking a shot at something new is celebrated, as long as something is learned.
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Opinions expressed by Entrepreneur contributors are their own.
Key Takeaways
- High-performing entrepreneurs avoid constant reactivity by filtering distractions and focusing their mental energy on decisions that drive meaningful outcomes.
- Build reflection and recovery into the workday. Create micro-pauses to question assumptions, reassess direction and examine whether momentum is still aligned with purpose.
- Simplifying workflows, reducing friction and staying close to customers and operational realities help entrepreneurs make better decisions and sustain long-term results.
Spend enough time building companies, and in my case, navigating both medicine and entrepreneurship, and a counterintuitive pattern begins to emerge. The people who consistently deliver are not the ones operating in a state of constant visible intensity.
In fact, many of the highest-performing founders I’ve encountered appear surprisingly controlled. Sometimes even uneventful from the outside.
The separation happens in quieter ways.
It reveals itself in how they protect attention, structure decisions and preserve energy for moments that genuinely matter. These are not dramatic habits. They are small, repeatable behaviors that compound silently while nobody is paying attention.
Over time, I’ve come to believe that in high-pressure environments, habits become infrastructure. And entrepreneurs who consciously build that infrastructure create an advantage that is extraordinarily difficult to replicate.
1. I’ve learned that attention is a precious resource.
Earlier in my entrepreneurial journey, I believed responsiveness was synonymous with effectiveness. Every message deserved attention. Every meeting felt important. Every opportunity seemed urgent.
That instinct becomes expensive very quickly.
Over time, I developed the discipline of deliberate non-engagement. I let things pass. I delay responses. I opt out of conversations that do not meaningfully influence outcomes.
This is not simply about selectivity. It is about cognitive preservation.
Every input competes for mental bandwidth. When attention becomes fragmented, thinking loses depth. Decision-making becomes reactive rather than strategic.
Some of the most effective entrepreneurs I know are exceptionally disciplined about what they refuse to engage with. They understand that clarity is achieved by filtering aggressively and protecting attention with intention.
2. I integrate thinking directly into execution.
There is a common assumption that meaningful thinking happens away from work, during retreats, long breaks or isolated strategy sessions. My experience has been different.
Some of the clearest strategic insights I’ve had emerged in the middle of execution itself: between meetings, immediately after difficult conversations, during transitions between decisions.
I’ve learned to create deliberate micro-pauses throughout the day. Brief moments to question assumptions, reassess direction and examine whether momentum is still aligned with purpose. Without those interruptions, execution continues, but direction quietly deteriorates. Decisions become incremental. Activity increases while clarity declines.
In medicine, this distinction matters enormously. A clinician moving quickly without periodically reassessing the situation can continue executing flawlessly in the wrong direction. Entrepreneurship is not very different. The discipline is not in stepping away from execution entirely. It is in embedding reflection inside it.
3. I design my days to reduce friction.
For years, I optimized aggressively for output. More meetings. More calls. More visible productivity. It felt efficient. It was not sustainable.
The real shift came when I stopped asking, “How do I get more done?” and started asking, “How do I make important work easier to sustain consistently?” That subtle distinction changed how I operate. I simplified recurring decisions. I standardized workflows. I removed unnecessary complexity from my day. I became far more intentional about where cognitive energy was being spent. Over time, the day itself began to feel lighter, despite the workload remaining demanding.
This principle is deeply connected to behavioral science. Human beings consistently underestimate the effect of friction on execution. Even small amounts of unnecessary complexity quietly drain decision quality over time.
When execution becomes smoother, energy is preserved. When energy is preserved, judgment improves.
The entrepreneurs who sustain performance over long periods are often not working less. They are operating inside systems designed to reduce unnecessary resistance.
4. I stay uncomfortably close to reality.
As organizations grow, abstraction becomes seductive. Dashboards replace direct observation. Summaries replace raw information. Layers absorb operational complexity. Distance begins to feel efficient. I’ve learned to resist that instinct deliberately.
Even today, I make it a point to stay close to customer conversations, unfiltered feedback, operational friction points and the realities of execution on the ground. In healthcare, distance from reality can become dangerous very quickly. Clinical decisions made from incomplete or abstracted information carry consequences. I’ve found the same principle applies to leadership and innovation.
The founders who remain closely connected to what is actually happening tend to make fewer unforced errors. Their judgment sharpens because it remains grounded in reality rather than interpretation. As companies scale, proximity becomes uncomfortable. But it also becomes incredibly valuable.
5. I protect energy through deliberate, short resets.
Burnout is often discussed as a function of long hours, with recovery framed primarily as vacations or extended time away. I think the issue is more immediate and more physiological than that.
Over the years, I’ve become increasingly deliberate about building short resets into the middle of demanding days. A pause between meetings. A brief walk before a major decision. A few minutes of silence after an intense interaction. These moments appear insignificant in isolation. Their cumulative effect is substantial.
Without resets, cognitive residue accumulates. Attention narrows. Emotional regulation weakens. Decisions become rushed without us fully realizing it. Harvard Business Review says that it’s important to “create several moments to pause over the course of your workday. By doing so, there will be a cumulative benefit, as you’ll be able to more effectively manage your energy and capacity, helping you to be more resilient.”
I’ve found that a few intentional minutes of recalibration can restore clarity more effectively than pushing through another uninterrupted hour.
The advantage few people talk about
None of these habits is particularly complicated. They do not require sophisticated tools, large teams or dramatic lifestyle overhauls. That is precisely why they are often underestimated.
Most entrepreneurs search for leverage in strategy, funding, technology or talent. Those variables matter immensely. But daily operating behavior quietly determines how effectively those advantages are ultimately used. Over time, the divergence compounds.
One founder operates in a state of constant reaction. Another operates with protected attention, preserved energy and deliberate clarity. Across decisions, across quarters, across years, that difference becomes profound.
Where I would start
If my own journey across medicine, innovation and entrepreneurship has taught me anything, it is that meaningful change rarely begins dramatically. It begins precisely.
Ignore one unnecessary input. Remove one source of friction. Create one intentional pause inside the day. Then observe what changes. Small adjustments, repeated consistently, reshape how we operate. And ultimately, how we operate shapes what we build.
Entrepreneurship celebrates visible milestones, funding rounds, launches, acquisitions and public wins. But the foundations of those outcomes are usually far less visible.
They exist in the quiet architecture of the day. In the systems that either preserve energy or quietly deplete it. The entrepreneurs who separate themselves over time do so because they learn to operate differently, long before anyone notices.
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Opinions expressed by Entrepreneur contributors are their own.
Key Takeaways
- Reflecting on a decade of experience as a CEO, offering insights gained from building and growing a successful business.
On the heels of my business’s 10-year anniversary, I’ve been reflecting on the journey and the many lessons I’ve learned in my decade as CEO. Below, I’ll share the ten most profound takeaways — the ones I wish I’d known in the early days of entrepreneurship. Apply them to your journey if you’re on a similar path!
1. Have clear expectations and consistent accountability
In my mind, these two factors are the foundation of successful leadership. Without clear expectations, your team members might not understand what you actually want from them, and their definition of success may not align with yours. Without consistent accountability, they won’t meet those expectations and will have a harder time learning how to improve.
Establishing clear, consistent communication ensures everyone is on the same page and moving towards the same goals.
Related: I Wish I Knew These Four Things Before Starting My Own Business
2. Understand evolution vs. revolution for leadership hires
When it comes to hiring for leadership roles, make sure you understand the roles you actually need. My best advice is this: Hire a manager when you need evolution and an executive when you need revolution.
I’ve learned (the hard way!) that all leadership hires are not created equal. A growing organization will eventually need both, but understanding whether you’re looking for evolution or revolution will help you make more strategic hiring decisions.
3. Know that company culture runs deeper than “fun”
Fun is an element of company culture, and I do believe you should invest in it — whether that’s through team breakfasts, team outings or other activities beyond just work. But true culture is about creating an environment where everyone feels valued and supported, and that goes beyond just having a good time together.
If you want to foster a company culture that doesn’t rely on throwing parties or catering lunches, be mindful of the little things, too: how your leadership team answers hard questions, how you balance transparency with protecting your team from hard truths and how you treat people day-to-day. Your employees will notice all of these details, and they really add up.
4. Expect everything to cost twice as much and take twice as long
Over the years, I’ve come to expect everything — from new projects to hiring decisions to new products — to take longer and cost more than I expect. And even when I try to apply this lesson ahead of time, I’m still likely to underestimate.
Planning with this principle in mind can help manage expectations and reduce frustration when things don’t go exactly as planned. A buffer is a good thing!
5. Hire a coach
My two co-founders and I started working with an executive coach about eight years into running the business, and I wish we’d done it sooner.
Coaches help you find your leadership blind spots, offer an impartial sounding board when you face challenges and help other members of your team level up alongside you. It may take time to find the right person for your needs, but in my experience, it was worth the effort.
Related: 8 Important Lessons From Leading Entrepreneurs
6. Co-founders are everything
Co-founders are the people with whom you can share your truest experiences: your deepest fears, your most outlandish concerns and your greatest triumphs. A strong co-founder relationship is crucial for enduring the highs and lows of entrepreneurship.
Find the right people to hold you accountable, balance out your skill set and make the experience of running a business a little less grueling.
7. It sucks, but it gets better
In Lemonlight’s early years, I was regularly working 14-hour days, putting out constant fires and feeling like my to-do list was never-ending. Today, the company runs pretty smoothly with the structures and people we have in place, allowing me to focus on big-picture thinking and finding areas where my expertise is helpful.
I won’t sugarcoat it: Starting a business is hard. But if you just take it one day at a time, it really does get easier.
8. A little progress every day is impactful
Speaking of taking it one day at a time, little progress every day adds up. We’ve had days where the wins and milestones were especially noticeable, but most of the last 10 years has just been moving the needle forward a little bit at a time.
Ten years later, somehow that amounts to 20,000+ videos, 5,000+ clients and 150+ team members. The progress isn’t always noticeable, but it’s always there. Consistency is powerful!
9. Financial acumen is important
Having solid finances is a major component of entrepreneurship, and while it’s important to find experts you trust to support you, it’s also essential to have some personal understanding of your business’s finances.
Being able to read and understand your primary financial statements, track your key performance indicators and move the needle towards your financial goals is invaluable. Don’t just trust someone else to get it right, especially early on when you probably can’t afford world-class help.
Related: 4 Lessons That Most Successful Entrepreneurs Had to Learn the Hard Way
10. You don’t save money if you spend it elsewhere
In the early years at Lemonlight, we were conscious of every dollar we spent, but we had a bad habit of “saving” money in one area only to spend it in an unproductive way elsewhere. We’d pat ourselves on the back for cutting costs, but that money wasn’t actually helping our bottom line.
If you find an opportunity to save money, make sure those savings stay saved — or, at the very least, they’re spent on something with real value. Don’t fall into the trap of thinking you’ve done a great job just to waste that money somewhere else. Real savings should strengthen your business, not just get shuffled around.
Entrepreneurship may be framed as a solo effort, but the reality is you don’t have to figure everything out on your own. I hope these lessons from my business can help you skip some of the uncertainty in yours, making progress without quite as many roadblocks.
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Opinions expressed by Entrepreneur contributors are their own.
Entrepreneurship is a wild ride, and it’s not for the faint of heart. If you are reading this article, you were born to shake things up and pave your own way. And as some of the most successful entrepreneurs in history have said, the key to success is to just start. Here are 15 inspiring lessons from legendary entrepreneurs.
1. “Just start.” — Eric Ries, author of The Lean Startup
The hardest part of any journey is the first step, so why not just take it and see where it leads? Don’t wait for the perfect moment or the perfect idea. If you don’t start, you’ll never finish.
2. “What would you do if you weren’t afraid?” — Sheryl Sandberg, COO at Meta
Turn fear into your motivation. Strive for more.
3. “The biggest risk is not taking any risk.” — Mark Zuckerberg, founder of Facebook
Taking risks is like jumping into a cold plunge—it may be uncomfortable at first. Ultimately, it will help you achieve your goals.
4. “You must do the things you think you cannot do.” — Eleanor Roosevelt, former First Lady
Reach beyond our perceived limitations and strive for greatness.
Related: Sign up for a one-on-one mentor session with a startup expert
You are capable of achieving more than you think is possible. You are probably operating at a 3/10 when you realistically can ramp to an 8/10. With hard work and determination, you can push through any barrier and come out stronger on the other side. So dream big and never give up!
5. “You don’t learn to walk by following rules. You learn by doing, and by falling over.” — Richard Branson, founder of Virgin Group
You’ll learn to take the right risks and be prepared for the occasional stumble. After all, there’s no better way to learn than by doing and getting back up again.
6. “If you’re not stubborn, you’ll give up on experiments too soon. And if you’re not flexible, you’ll pound your head against the wall and you won’t see a different solution to a problem you’re trying to solve.” — Jeff Bezos, founder of Amazon
Flexibility and stubbornness are both essential traits for entrepreneurs, so make sure to keep them in balance. With the right combination of boldness and patience, you’ll be well on your way to achieving success!
7. “If you can’t fly then run. If you can’t run then walk. If you can’t walk then crawl, but whatever you do you have to keep moving forward.” – Oprah Winfrey, media mogul
You should never give up, no matter how hard the journey may be.
Regardless of the challenges and obstacles that stand in your way, you can find a way to move forward. You all have the power to keep pushing, no matter what.
8. “My life didn’t please me, so I created my life.” — Coco Chanel, fashion icon
You can do anything you set your mind to. Don’t let life just happen to you—make it happen.
9. “Fail often so you can succeed sooner.” — Tom Kelley, IDEO partner
Failure and success are tied. More at-bats will help you iterate faster and learn more. Failing often will help you get closer to success – no matter how small the success, it’s still a step in the right direction.
10. “The way to get started is to quit talking and begin doing.” — Walt Disney, co-founder of the Walt Disney Company
Put Walt’s words of wisdom into action — stop talking and start doing! Success is within reach if you take the first step and learn from your mistakes along the way.
11. “In the modern world of business, it is useless to be a creative, original thinker unless you can also sell what you create.” – David Ogilvy, advertising executive
We’ve heard this before. Spencer Rascoff preaches that all entrepreneurs need to be salespeople. Able to sell your business, your product, and your company vision.
12. “The best way to predict the future is to create it.” — Abraham Lincoln, former US President
Abraham Lincoln is a man who knew a thing or two about making history.
Don’t wait for life to happen to you, make it happen. It’s a reminder that we’re all capable of creating our own destiny and that the future is ours to mold.
13. “Fearlessness is not the absence of fear. It’s the mastery of fear. It’s about getting up one more time than we fall down.” —Arianna Huffington, editor-in-chief of The Huffington Post
Don’t shy away from fear. Face it head-on.
It’s an ongoing battle of getting up even after life knocks us down.
14. “Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do.” – Steve Jobs, former CEO of Apple
Let’s face it, work takes up a big chunk of our lives, and the only way to make that time meaningful is to do something that you truly believe in.
15. “In whatever you do, you’re not going to stand out unless you think big and have ideas that are truly original. That comes from tapping into your own creativity, not obsessing over what everyone else is doing.” —Sophia Amoruso, founder of Nasty Gal
Making an impact requires more than just following the status quo; it calls for embracing your own innovative ideas. To truly stand out, you must be willing to take risks and unleash your creative potential.
The key is to focus less on what others are doing, and instead aim to generate unique solutions that can make a real difference. Only then will you be able to make a meaningful mark on the world.
Related: Sign up for a one-on-one mentor session with a startup expert
16. “Be patient with yourself. Self-growth is tender; it’s holy ground. There’s no greater investment.” — Stephen Covey, author of “The 7 Habits of Highly Effective People”
Not an overnight success? Then, you are not making the headlines. It can take time to get things up and running and that is OK.
Don’t be too hard on yourself.
17. “Your most unhappy customers are your greatest source of learning.” — Bill Gates, co-founder of Microsoft
From my time pre-IPO at Uber, Instawork, and Intro, I’ve learned that your customers build your product roadmap. Listen to them.
18. “The best time to plant a tree was 20 years ago. The second best time is now.” — Chinese Proverb
In life, it’s best to take action as soon as possible.
The best time to plant a tree was 20 years ago because it would have had time to grow and mature by now. However, the second best time to plant a tree is now, even though it won’t be as mature as it would have been 20 years ago.
The same goes for any goal or task, the earlier you start, the better the outcome will be, but it’s never too late to start, and the present is always the second-best time to start.
