Win Or Learn: The Entrepreneur's Mindset

Forbes

27-05-2025

Daniel is an entrepreneur, founder & CEO of MyOutDesk devoted to providing growing companies with proven, reliable virtual assistants.
The common framing around failure in entrepreneurship—of things being win or lose—doesn't work for me. You're either winning or you're learning, and learning is iterative and 'the entrepreneur's mindset.'
I've been establishing, growing and selling businesses for almost 20 years, and that's the mindset I decide to approach every entrepreneurial endeavor with. I know 18% of small businesses fail within their first year (and 50% within the first five), but I also know there are a lot of people like me out there who also decide every day to pursue a passion or idea that's as likely to fail as it is to succeed.
That decision is the first of a million-plus decisions entrepreneurs have to make. And there are just as many different routes that could get them where they want to go. As someone who's faced the inevitable decision paralysis countless times and worked with thousands of entrepreneurs who've experienced the same, I've learned a few tricks for turning decision paralysis into progress—because action, even if in the wrong direction, is better than stagnancy.
Is taking the initial leap the hardest part … or everything that comes after it? Well, that's for each founder to decide. What isn't up for debate is that the decisions made during the ideation and planning phases of the entrepreneur have the power to significantly impact future business success.
Product-market fit is paramount. Find a clear path to customer demand, and offer customers a value proposition that no other company can. While your business idea must be unique, the elevator pitch for it can be formulaic: I provide this (product/service) for people (describe the person/customer/business) that want (outcome). In its simplest form, business is humans helping other humans; if you're good, then the business will grow.
To be good, you must commit to a pursuit of mastery. A dedication to your business's growth and development is a dedication to your own personal growth and development as well. Ongoing education and improvement in marketing, operations and delivery are critical, but sales mastery is nonnegotiable as founders are constantly selling their vision to customers, investors and employees.
Consider whether a blended workforce is the right choice for you. It can be a good idea to hire internal staff for the most technical and high-value tasks, and hire outsourced staff for the process-based tasks. (Disclosure: My company helps with outsourcing, as do others.) But for many entrepreneurs, the first 'hire' should be a technology system like a CRM or ERP platform that supports those team members and you in every business decision from customer acquisition to product or service distribution. This kind of blended model that employs physical, virtual and digital team members takes advantage of the strength of AI in its current era and gives humans the ability to leverage that technology to help better the business.
Some of the most common entrepreneurial decisions are the most difficult to make because there's no right or wrong answer or one answer that fits every entrepreneur. The good news is, in my experience, it's less about what you decide and more about how.
Separate CEO from self. It's your business, but the business is not you. It should be treated as its own entity, and decision-making should be based on what's best for the company, not the individual(s) running it, because those are not always one and the same. Founder compensation is a good example. While taking a salary is typically preferred from a personal perspective, it may not be best for a new business that still has entry-level revenue and weak financial stability. As the business grows and scales, so can the market value (and salary) of the CEO.
Focus on the long term. I've learned that effective leaders prioritize the long-term health and mission of the business above personal gain or convenience. They lead 'from the front,' never asking employees to do something they wouldn't be willing to do themselves. This approach can foster trust, build credibility and effectively motivate teams to stay the course in the short term for better results in the long run—results that everyone on the team will professionally and personally benefit from.
Do the due diligence to turn curiosity into context. Ask questions. Understand the 'what' and the 'why' of every situation, be it managing employee performance or evaluating pitches promising grandiose visions. As a founder, you'll inevitably possess a broader context than individual contributors and must tailor your communications and operations decisions to reflect that big-picture view.
Be okay with saying no—strategically. It's a necessary skill for leaders to protect their business, their time, the team doing the work and the customers they serve. Establishing guardrails early on and sticking to a disciplined evaluation process when determining things like whether or not to hire friends and family or take on investors can prevent biased decision-making based on familiarity or immediate appeal instead of true business and customer needs.
Often, situations are less about the decision and more about how you approach making it—less about a founder's checklist and more about a founder's willingness to take risks.
While market opportunity and product-market fit are paramount, successful entrepreneurship often stems from an innate drive and passion for pursuing a vision. It takes courage, commitment and an inner self-assuredness to turn a gut feeling into a foundation for a profitable venture, not another failure statistic.
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