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Everything I Learned About Cultivating an Entrepreneurial Mindset: How to Overcome Challenges, Set Goals, and Build Your Dream Business

Written by: Taylor Cromwell
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BUSINESS STARTUP KIT

9 templates to help you brainstorm a business name, develop your business plan, and pitch your idea to investors.

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I never set out to be an entrepreneur ¡ª I just wanted to write. But going freelance taught me I was running a business, whether I owned that title or not. The most important shift I've made since then is learning to think like an entrepreneur, not just a freelancer.

That mindset change is what turned this into something sustainable. It¡®s the difference between a side project that burns you out and a business that supports your life. Thinking like an entrepreneur doesn¡¯t mean building a unicorn startup ¡ª it can be a solo creative business, local brand, or small team doing work you love.

In this article, I¡®ll break down what the entrepreneurial mindset actually looks like and how I¡¯ve developed it over time. Whether you're freelancing, building something new, or figuring it out as you go, I hope this gives you a framework to build from.

Table of Contents:

  • What is an entrepreneurial mindset?
  • Entrepreneurial Mindset Characteristics
  • Employee vs. Entrepreneur Mindset
  • How to Develop the Entrepreneurial Mindset
  • Entrepreneurial Mindset Quotes
  • Entrepreneurial Mindset Examples
  • Anyone Can Have An Entrepreneurial Mindset

When I first started working for myself, I didn¡¯t call myself an entrepreneur. I wasn¡¯t trying to build the next big thing ¡ª I just wanted to write and get paid well to do it. But pretty quickly, I realized that freelancing wasn¡¯t just about delivering work. It was about making decisions. Taking risks. Setting boundaries. Thinking ahead.

And that¡¯s really what the entrepreneurial mindset is: it¡¯s how you approach uncertainty, growth, and responsibility. It¡¯s how you handle the inevitable challenges ¡ª because they will come ¡ª and how you show up anyway.

It¡¯s not just for startup founders or people trying to raise a round. You can have an entrepreneurial mindset whether you¡¯re running a solo business, launching a side project, or managing your role inside a bigger company. It¡¯s about how you think, not just what your job title is.

In my experience, the entrepreneurial mindset looks like:

  • Taking ownership over your time and outcomes
  • Looking for solutions instead of waiting for instructions
  • Being willing to bet on yourself, even when it¡¯s uncomfortable
  • Getting clear on what you¡¯re building ¡ª and why

It¡¯s a mindset that gets stronger the more you use it. And it¡¯s the difference between reacting to your work and intentionally building something that lasts.

Entrepreneurial Mindset Characteristics

One thing I¡¯ve learned: before you write a business plan or lock in your first client, you¡¯ve got to get your head in the right place. And that starts with mindset.

Thinking like an entrepreneur doesn¡¯t mean having all the answers. It means being willing to figure things out even when things get hard, unclear, or overwhelming. You have to train yourself to stay focused on the bigger picture while navigating the day-to-day. And most of that work? It happens in your mindset, long before it shows up in your results.

Here are a few key traits that have shaped the way I show up, and the ones I¡¯ve seen make the biggest difference in others, too:

develop an entrepreneurial mindset: set clear goals, prioritize learning, reframe failure, and embrace risk

1. Self-Drive

No one¡¯s coming to hold you accountable. Especially when you¡¯re self-employed or building something from scratch, you are the one who has to stay motivated, keep showing up, and make decisions daily. Self-drive doesn¡¯t have to mean grinding nonstop; it means you care enough to stay in motion, even when no one¡¯s watching.

Whether it¡¯s carving out time to learn something new, pitching that one dream client, or just sending the follow-up email you¡¯ve been avoiding, forward motion adds up.

2. Flexibility

Things won¡¯t always go the way you planned. (They rarely do in my experience!) And I¡¯ve found that the most resilient people are the ones who know how to adapt without losing their direction.

Being flexible might mean changing your offer, adjusting your messaging, or scrapping a strategy that used to work. But it also means staying open to feedback and letting your business evolve alongside you.

3. Creativity

Creativity isn¡¯t just for designers or writers; it¡¯s a core part of problem-solving in business. Whether you¡¯re figuring out how to market something new, refining your customer experience, or deciding how to price your offer, creative thinking gives you an edge. I¡¯ve relied on my creative problem-solving skills nearly every day since starting my own thing.

4. Authenticity

One of the hardest ¡ª and most important ¡ª parts of entrepreneurship is staying grounded in who you are. It¡¯s easy to get swept up in what everyone else is doing. But the businesses I trust most are the ones that feel real, consistent, and values-driven.

So that¡¯s something I¡¯ve tried to focus on most while building my business: trying to find a way to grow in a way that feels true to me and aligns with my core values and goals.

5. Tenacity

According to data from , only 28% of businesses are profitable within their first year of starting; 36% are super profitable within two years of operation.

What does this data tell me? Well, in short, it proves that entrepreneurs have to have the tenacity to keep trying if they want to see the results they¡¯ve dreamed of. Going through setbacks (i.e., low sales or lack of brand visibility) can chip away at your confidence, but true entrepreneurs understand that it¡¯s all a part of the job.

Employee vs. Entrepreneur Mindset

One of the biggest mindset shifts I had to make when I started working for myself was unlearning how I¡¯d been trained to think as an employee. I didn¡¯t realize how much that mindset had shaped my default approach: waiting for direction, assuming someone else set the rules, and reacting instead of leading.

But once you¡¯re on your own, no one¡¯s handing you a roadmap. You are the roadmap. That means taking full responsibility for the wins and the losses. It means deciding what needs to happen next ¡ª and then doing it. That¡¯s what separates employees from entrepreneurs: ownership.

Here are a few of the biggest differences I¡¯ve seen (and lived through) when it comes to how entrepreneurs and employees think:

employee mindset vs entrepreneur mindset

1. Entrepreneurs prioritize ruthlessly.

When you¡¯re an employee, your priorities are usually handed to you. You¡¯ve got a manager, KPIs, a checklist. There¡¯s structure. But when you¡¯re running your own thing, every decision is on you.

There¡¯s no boss telling you what to work on first. You¡¯ve got to look at everything ¡ª from taxes and invoices to sales calls and client delivery ¡ª and decide what¡¯s actually going to move the needle. If you »å´Ç²Ô¡¯³Ù learn how to prioritize, you¡¯ll end up buried in busywork that looks productive but doesn¡¯t move your business forward.

2. Entrepreneurs »å´Ç²Ô¡¯³Ù fear failure; they expect it.

One thing I¡¯ve learned from studying great founders (and just living through it myself): failure is part of the process.

Entrepreneurs experiment constantly. Some things work. Some »å´Ç²Ô¡¯³Ù. You can¡¯t let every misstep derail you. You have to be able to say, ¡°Okay, that didn¡¯t work. What¡¯s next?¡± and keep moving.

I remind myself of this all the time: no one taught me how to run a business. I¡¯m learning as I go. And honestly, that¡¯s what entrepreneurship is ¡ª figuring things out in real time, making decisions, and adjusting when things shift.

3. Entrepreneurs solve problems.

As an employee, it¡¯s easy to default to asking, ¡°What should I do?¡± But when you¡¯re an entrepreneur, the better question becomes, ¡°What needs to get done?¡±

As ¡°Entrepreneurs are not just business owners ¡ª they are problem solvers. They wake up asking, ¡®How can I create value today?¡¯ They look for pain points, inefficiencies, and unmet needs. And they »å´Ç²Ô¡¯³Ù wait for permission to act. They take responsibility for shaping their future.¡±

It¡¯s about seeing the bigger picture and finding solutions, whether that¡¯s improving your client onboarding, fixing a broken system, or setting your own payment terms instead of letting vendors decide. That proactive thinking is what keeps your business growing and sustainable.

4. Entrepreneurs aren¡¯t threatened by people more intelligent than them.

One of the best mindset shifts I¡¯ve made is learning to treat people who are further ahead as inspiration, not competition. When you¡¯re building something on your own, it¡¯s easy to get caught up in comparison or feel intimidated by people who seem to have it all figured out. But the entrepreneurial mindset flips that.

I want to be around people who are smarter, more experienced, or a few steps ahead because that¡¯s where the real learning happens.

Early in my journey, I definitely struggled with this. I felt like I had to prove I was capable or already knew what I was doing. Now, I realize that humility is one of the most powerful tools you can have as an entrepreneur. You can¡¯t grow if you¡¯re clinging to your ego.

The founders I respect the most are the ones who ask questions, listen deeply, and surround themselves with people who challenge them to think bigger.

5. Entrepreneurs own all their decisions ¡ª good and bad.

When you work for yourself, there¡¯s no one else to hide behind. Every choice you make ¡ª what you take on, what you ignore, how you price, how you deliver ¡ª is on you. That can feel heavy, but it¡¯s also empowering.

I¡¯ve made decisions I later regretted, projects that drained me, pricing that didn¡¯t make sense, and time I spent in the weeds instead of thinking long-term. But owning those moments without spiraling has been an important lesson for me.

Pro tip: My advice for preventing stressful business things before they happen? Create a business plan that outlines everything, from your business name to how you¡¯ll pitch your business to investors. I recommend using if you want to organize your thoughts with easy-to-follow, easy-to-share templates.

How to Develop the Entrepreneurial Mindset

Most advice about building an ¡°entrepreneurial mindset¡± is vague at best. People love to say things like ¡°Take risks!¡± or ¡°Think like a founder!¡± but rarely break down what that actually looks like in real time, especially when you¡¯re building something solo, without a blueprint.

So here¡¯s my version. This is what developing an entrepreneurial mindset has looked like for me over the last few years: the shifts I¡¯ve made, the systems I¡¯ve built, the ways I¡¯ve learned to make better decisions, and the risks I¡¯ve taken that didn¡¯t always feel smart in the moment.

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1. Start by prioritizing revenue ¡ª then build around what works

In the beginning, I was focused on the kind of work I wanted to do: writing articles I loved, working with brands I admired. But I quickly realized that was still coming from an employee mindset, where fulfillment was the goal and revenue was someone else¡¯s problem.

Shifting to an entrepreneurial mindset meant flipping that: I had to treat revenue as the primary focus. What types of projects could actually fund the business? What did I need to earn in a month to pay myself, cover expenses, and reinvest in growth?

That meant tracking time, calculating profit margins, and paying attention to what was actually working, not just what I felt like doing.

Try this:

  • Do a time audit for one week. Write down what you¡¯re working on and how long it takes.
  • Match that list with the income tied to each activity.
  • Ask yourself: What¡¯s earning money? What¡¯s just ¡°work¡±?

Reflection prompts:

  • If you had to double your income without working more hours, what would you do differently?
  • Which of your current services or tasks are most aligned with your long-term business goals?
  • Are you spending more time ¡°working¡± than actually running the business?

2. Learning is a constant.

One of the fastest ways to grow as a business owner is to admit what you »å´Ç²Ô¡¯³Ù know and stay open to learning at every stage.

When I first went freelance, I was mostly focused on figuring out how to get clients, raise my rates, and manage my income without panicking. So I read every article I could find, listened to podcasts from people who were a few steps ahead, and watched how successful solopreneurs operated. But the deeper I got into business, the more I realized that learning isn¡¯t just for beginners. It doesn¡¯t stop once you hit six figures or land a dream client. It becomes more essential the further you go.

At the start, it was survival learning. Now, it¡¯s strategic learning ¡ª figuring out how to scale sustainably, build systems, grow a brand, etc. This happened because I kept listening, investing in coaching, joining communities, and following curiosity. Books like Entrepreneur Revolution by Daniel Priestley gave me language for what I was experiencing. Conversations with peers helped normalize the messy middle. And paid groups gave me access to people who were building real businesses.

Try this:

  • Pick one learning channel to commit to for the next 30 days: podcast, book, or email newsletter.
  • Identify a peer or mentor you admire and reach out with a thoughtful question.
  • Set a learning goal that matches your current stage. (e.g., ¡°I want to better understand personal branding,¡± or ¡°I need to streamline my systems.¡±)

Reflection prompts:

  • What problem are you currently stuck on that someone else has already solved?
  • Where in your business do you feel least confident, and what would it look like to learn your way out of that discomfort?
  • Are you prioritizing learning with the same intention you give to earning?

3. Know that pivoting isn¡¯t failure.

Failure isn¡¯t something you outgrow. It¡¯s something you learn to work with.

In my business, some of the biggest breakthroughs came right after things didn¡¯t work. I¡¯ve pivoted service offerings, walked away from clients, shut down ideas I thought would be game-changers, and each of those moments taught me something I couldn¡¯t have learned any other way. The earlier you accept that failure is part of the job, the easier it becomes to keep going.

The shift here is mindset: you stop seeing mistakes as signs that you¡¯re bad at this, and start seeing them as part of the data set. What didn¡¯t work? Why? What would you try differently next time? That curiosity is the root of resilience.

One example: I used to offer ghostwriting for LinkedIn. At one point, it felt like the perfect fit. But then AI tools exploded, the market shifted, and I realized I didn¡¯t actually enjoy the work anymore. Rather than forcing myself to stick with it, I chose to pivot. I stopped offering that service and leaned into more strategic, narrative-focused work that aligned with where I wanted to go. Was it scary to let go of a consistent revenue stream? Of course. But that ¡°failure¡± helped me plot my next step.

Try this:

  • Write down one recent mistake or ¡°flop¡± in your business. Underneath it, list three things it taught you.
  • Create a ¡°Failure Archive¡± folder ¡ª seriously. Keep notes on things that didn¡¯t work and why. Revisit it every quarter.
  • Normalize it: share a small failure story on social or with a peer. You¡¯ll be surprised how many people relate.

Reflection prompts:

  • What¡¯s something you¡¯re afraid to try because you »å´Ç²Ô¡¯³Ù want to fail?
  • When was the last time a ¡°mistake¡± led to something better?
  • How would your business change if you treated failure as feedback instead of final?

4. Create systems that help you tolerate risk.

People often talk about entrepreneurship like it¡¯s all about risk ¡ª quitting your job, maxing out your credit card, leaping before you¡¯re ready. But that¡¯s not how most successful entrepreneurs operate. The ones I admire (and try to emulate) »å´Ç²Ô¡¯³Ù take reckless risks. They build systems that make risk possible.

For me, risk tolerance has always come down to stability. I¡¯m willing to invest time, energy, and even money into something uncertain only if I¡¯ve built a solid enough foundation to support it.

When I decided to launch a newsletter, , I wasn¡¯t monetizing it right away. But I had built a stable client base that covered my financial needs. That gave me the breathing room to experiment. I knew roughly 80% of my income was secured for the next few months, which made that creative risk feel manageable.

The same principle applies to product development, taking on bigger clients, or changing your pricing. It¡¯s not about avoiding fear ¡ª it¡¯s about designing your business to carry that fear without collapsing.

Try this:

  • Audit your revenue: How much of your income is predictable? Where could you build more stability so you can take creative risks?
  • Block out time each week for ¡°non-revenue¡± work that might pay off long-term (e.g., a new offer, content creation, or partnerships).
  • Before taking a big leap, ask yourself: What¡¯s the worst-case outcome? What¡¯s the best-case scenario? And what would it take to recover?

Reflection prompts:

  • What¡¯s one risk you¡¯ve been avoiding? What would make it feel safer to try?
  • Are you holding back out of fear, or do you just need a stronger foundation?
  • What¡¯s a calculated risk that¡¯s paid off for you already?

5. Stop thinking like a scrappy solo operator and start thinking like an investor.

One of the most important mindset shifts I¡¯ve made in the last few years is this: I stopped treating every expense like a threat and started thinking about investments in terms of return.

When you¡¯re operating from an employee or scarcity mindset, it¡¯s easy to see every tool, subscription, or service as ¡°extra.¡± I used to hesitate before spending $20/month on software, even if it saved me hours of admin work. I¡¯d agonize over investing in coaching or joining a paid community, thinking I should be able to figure this out on my own.

But the truth is, those investments are exactly what helped me level up. When I started putting real money into tools that saved time, systems that reduced friction, and relationships that expanded my network ¡ª I saw my business shift. I wasn¡¯t just doing more work. I was doing smarter work. And I was building something with long-term value.

The entrepreneurial mindset here is simple: stop optimizing for today¡¯s savings and start optimizing for future leverage.

Try this:

  • Do a cost vs. ROI review: What tools or services are you using that actually save time or generate income? Which ones are draining resources?
  • List 2¨C3 areas of your business where you could buy back time (e.g., bookkeeping, scheduling, editing). Could you automate, delegate, or upgrade your tools there?
  • Set an ¡°investment budget¡± for the next 30 days. Even $100 can make a huge difference.

Reflection prompts:

  • Where are you still operating from a scarcity mindset ¡ª and what would it look like to shift that?
  • What¡¯s one area of your business where you¡¯re spending too much time doing something a tool or expert could do faster?
  • How might your business change if you treated yourself like your most valuable asset?

6. Redefine what ¡°entrepreneur¡± means.

A lot of people hesitate to call themselves entrepreneurs because the word feels loaded. It brings to mind venture capital, Silicon Valley, 10X growth, and pitch decks. But that narrow definition leaves out millions of people who are building real businesses on their own terms.

When I first went freelance, I didn¡¯t think of myself as a founder. I thought I was just a writer working for herself. But over time, I realized that I wasn¡¯t just delivering work ¡ª I was setting vision, managing operations, building relationships, experimenting with new revenue streams, and shaping a business that could actually support my life. That¡¯s entrepreneurship.

I¡¯m passionate about expanding this definition so more people can see themselves in it. You »å´Ç²Ô¡¯³Ù need a co-founder or funding to build something meaningful. You can be a solo creator with a strong newsletter, a service provider with a niche audience, a digital product seller with a unique point of view. What matters is that you¡¯re taking ownership of how you earn a living, and that¡¯s a powerful thing.

Try this:

  • Write down your definition of entrepreneurship. Not the textbook one ¡ª the one that feels true for your life and goals.
  • Audit your business through this lens: Are you operating like a founder or just a freelancer? Where are you still playing small?
  • Follow and study entrepreneurs who »å´Ç²Ô¡¯³Ù fit the mold. See how they¡¯ve built systems, brands, and communities around who they are.

Reflection prompts:

  • What¡¯s held you back from calling yourself an entrepreneur?
  • What would it mean to fully own that identity, even if your business looks different from the traditional model?
  • Where are you already thinking like a founder, even if you haven¡¯t claimed the title yet?

Entrepreneurial Mindset Quotes

Sometimes (especially depending on the day you¡¯re having), motivation doesn¡¯t come from within. Sometimes, motivation comes from hearing someone else¡¯s take on success. Or struggle. Or just trusting the process. My point is this: It helps to hear someone else¡¯s take on how they made things happen when things got tough.

Whether you¡¯re looking for an alternative view on resilience or just need a pick me up, here¡¯s a curated collection of quotes I put together that I hope helps you see the entrepreneurship grind in a slightly different light:

On Perseverance

  • ¡°I¡¯m convinced that about half of what separates the successful entrepreneurs from the non-successful ones is pure perseverance.¡± ¡ª Steve Jobs
  • ¡°If you just work on stuff that you like and you¡¯re passionate about, you »å´Ç²Ô¡¯³Ù have to have a master plan with how things will play out.¡± ¡ª Mark Zuckerberg
  • ¡°There are no secrets to success. It is the result of preparation, hard work and learning from failure.¡± ¡ª Colin Powell
  • ¡°Have the end in mind, and every day make sure you¡¯re working towards it.¡± ¡ª Stephen Covey
  • ¡°Life, especially the life of an early-stage entrepreneur, is full of gigantic ups and downs. Make sure you »å´Ç²Ô¡¯³Ù let yourself get too high or too low. It¡¯s a marathon, and you just have to keep your legs moving at a steady pace.¡± ¡ª Chieh Huang

On Work Ethic

  • ¡°Work like there is someone working 24 hours a day to take it all away from you.¡± ¡ª Mark Cuban
  • ¡°Obsess to find ways to win. Work ethic separates the great from the good.¡± ¡ª Kobe Bryant
  • ¡°Getting in the 99th percentile takes focus and hard work. You won¡¯t get there without a strong work ethic.¡± ¡ª Brett Adcock
  • ¡°Hard work pays off. Hard work beats talent any day, but if you¡¯re talented and work hard, it¡¯s hard to be beat.¡± ¡ª Robert Griffin III
  • ¡°A great work ethic isn¡¯t about working whenever you¡¯re called upon. It¡¯s about doing what you say you¡¯re going to do, putting in a fair day¡¯s work, respecting the work, respecting the customer, respecting coworkers, not wasting time, not creating unnecessary work for other people, and not being a bottleneck.¡± ¡ª Jason Fried

On Taking Risks

  • ¡°Embrace accountability and take business risks under your own name; society will reward you with responsibility, equity, and leverage.¡± ¡ª Naval Ravikant
  • ¡°If I¡¯d been less willing to risk being misunderstood, Amazon would still be a bookstore.¡± ¡ª Jeff Bezos
  • ¡°Fearlessness is like a muscle. I know from my own life that the more I exercise it, the more natural it becomes to not let my fears run me.¡± ¡ª Arianna Huffington
  • ¡°There is no innovation and creativity without failure. Period.¡± ¡ª Bren¨¦ Brown

On Handling Failure

  • ¡°The only thing worse than starting something and failing¡­ is not starting something.¡± ¡ª Seth Godin
  • ¡°It's fine to celebrate success, but it is more important to heed the lessons of failure.¡± ¡ª Bill Gates
  • ¡°Success is not final, failure is not fatal: it is the courage to continue that counts.¡± ¡ª Winston Churchill
  • ¡°Do not be embarrassed by your failures, learn from them and start again.¡± ¡ª Richard Branson
  • ¡°The important thing is not being afraid to take a chance. Remember, the greatest failure is to not try. Once you find something you love to do, be the best at doing it.¡± ¡ª Debbi Fields Rose

On Motivation and Drive

  • ¡°There are lots of bad reasons to start a company. But there¡¯s only one good, legitimate reason, and I think you know what it is: It¡¯s to change the world.¡± ¡ª Phil Libin
  • ¡°All humans are entrepreneurs ¨C not because they should start companies but because the will to create is encoded in human DNA.¡± ¡ª Reid Hoffman
  • ¡°People often say that motivation doesn't last. Well, neither does bathing¡ªthat's why we recommend it daily.¡± ¡ª Zig Ziglar

On Leadership

  • ¡°Empathy isn¡¯t a soft skill; it¡¯s the hardest skill we learn.¡± ¡ª Satya Nadella
  • ¡°The secret to successful hiring is this: Look for the people who want to change the world.¡± ¡ª Marc Benioff
  • ¡°Leadership is not about titles or positions, but about active participation, learning from where systems fail.¡± ¡ª Bill Gates
  • ¡°Leadership is not about being in charge. It is about taking care of those in your charge.¡± ¡ª Simon Sinek

Entrepreneurial Mindset Examples

In my experience of chasing big goals, it¡¯s always been helpful to see people who¡¯ve made their dreams plausible and attainable regardless of the odds they faced. There¡¯s a lot we can learn from their story, too.

Check out these folks whose entrepreneurial mindset took them pretty far:

1. Sam Altman ¡ª CEO and Co-Founder of OpenAI

Before becoming the face of one of the most influential AI companies in the world, Sam Altman was already known for his ability to spot patterns, make bold bets, and rally smart people around ambitious ideas. As a former president of Y Combinator, Altman spent years studying what makes startups succeed and what makes founders tick.

But what makes Sam a true example of entrepreneurial mindset isn¡¯t just his technical intelligence ¡ª it¡¯s his clarity, conviction, and willingness to take calculated risks in the face of uncertainty.

In his widely read essay Altman breaks down the ingredients of outsized achievement. His advice? Be internally driven. Stay focused. Don¡¯t wait for permission. And never underestimate the compounding power of effort over time.

sam altman¡¯s how to be successful is essential reading for entrepreneurs

Some of my favorite quotes:

  • ¡°Self-belief is immensely powerful. The most successful people I know believe in themselves almost to the point of delusion.¡±
  • ¡°Entrepreneurship is very difficult to teach because original thinking is very difficult to teach. School is not set up to teach this¡ªin fact, it generally rewards the opposite. So you have to cultivate it on your own.¡±
  • ¡°I will fail many times, and I will be really right once¡± is the entrepreneurs¡¯ way. You have to give yourself a lot of chances to get lucky.
  • ¡°People have an enormous capacity to make things happen. A combination of self-doubt, giving up too early, and not pushing hard enough prevents most people from ever reaching anywhere near their potential.¡±

Takeaways from Altman¡¯s mindset:

  • Think long-term, but move fast. Altman emphasizes urgency without sacrificing vision.
  • Bet on yourself early. The sooner you commit to building, the more time you have to compound.
  • Curiosity is a superpower. The best founders, in Altman¡¯s eyes, are relentlessly curious.

6. Sophia Amoruso ¨C Founder of Nasty Gal and Business Class

Sophia Amoruso¡¯s rise is the kind of story that became internet legend. She started Nasty Gal as a vintage eBay shop run out of her apartment. In just a few years, she scaled it into a $100M+ fashion brand and inadvertently helped define a new wave of online entrepreneurship. But what really sets her apart isn¡¯t just the rise. It¡¯s how she¡¯s handled what came after.

Following Nasty Gal¡¯s high-profile bankruptcy, she went on to found Girlboss, then later Business Class, an online course for founders looking to build practical, profitable businesses on their own terms.

She¡¯s spoken candidly about her missteps, growth, and the way she had to redefine success ¡ª first as a breakout founder, then as a wiser, more grounded entrepreneur in her 30s.

Her entrepreneurial mindset is deeply rooted in self-awareness, resilience, and reinvention.

sophia amoruso¡¯s substack

Takeaways from Amoruso¡¯s mindset:

  • Use failure as a pivot point. She didn¡¯t stop building after Nasty Gal¡¯s downfall; she used these lessons to create Business Class and eventually launch her own venture fund.
  • Define success for yourself. Amoruso¡¯s journey reminds us that success isn¡¯t static, and it can look different for you at different stages.
  • Your story is your asset. She¡¯s built a brand by being transparent, imperfect, and in motion. In just a year, has become essential reading for aspiring entrepreneurs.

Anyone can have an entrepreneurial mindset.

Hopefully this has been helpful or even a little inspiring, especially if you¡¯re thinking about stepping into the entrepreneurial world. It¡¯s not some mysterious gift people are born with. It¡¯s a way of thinking you can learn. There¡¯s no one type of person who gets to be an entrepreneur. It all comes down to how you approach problems, take ownership, and keep improving.

One of the best ways to grow is to study people who are a few steps ahead, whether that¡¯s someone like Sam Altman or Sophia Amoruso, or people in your own network and community. There¡¯s something to learn from everyone if you¡¯re paying attention.

That¡¯s the part I come back to again and again: entrepreneurship is possible ¡ª and powerful ¡ª for anyone. You »å´Ç²Ô¡¯³Ù have to wait for permission. You just have to start.

Editor's note: This post was originally published in March 2021 and has been updated for comprehensiveness.

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