I Learned These 5 Lessons the Hard Way So You Don't Have To

Entrepreneur

2 days ago

Starting a business has been one of the most exciting and fulfilling chapters of my life — but it's also been unpredictable, humbling and often much harder than it looks from the outside. Here are a few pieces of hard-earned wisdom I wish I'd known from day one.
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Almost 20 years ago, when my business was still in its infancy, I posted a job listing that read: "New software company needs someone to answer phones and emails, lead sales, support clients and manage my correspondence while I'm away. No salary, no benefits, commission-only position." I was earning modest revenue from the software product I had built, but between support tickets, sales inquiries and product development — on top of my full-time job — I knew it was time to hire my very first employee.
Looking back now, it's a miracle that anyone responded. But one person did — cautiously — and that first hire became one of our longest-standing employees. While I don't regret how it turned out, I've learned a lot since then, including how many great potential candidates I likely scared off with that off-the-cuff ad. Like many early entrepreneurs, in the beginning, I relied more on instinct and grit than experience and strategy.
Starting a business has been one of the most exciting and fulfilling chapters of my life — but it's also been unpredictable, humbling and often much harder than it looks from the outside. Along the way, I've learned so many valuable lessons — many of them the hard way. Here are a few pieces of hard-earned wisdom I wish I'd known from day one.
Related: I Wish I Knew These Four Things Before Starting My Own Business
1. Build a business that fuels you every day
Lesson number one: You have to love what you are doing. If you don't, burnout will sneak up on you fast. Starting a company just because it sounds exciting, because you love the idea of entrepreneurship, or because you want to be your own boss isn't enough — the initial energy will only take you so far. The day-to-day grind of entrepreneurship is full of problem-solving, setbacks and way too many hours. Without a genuine passion and drive for the problem you're solving or the work itself, you'll likely lose momentum or exit early.
Every task won't thrill you, but the bigger picture should. Keep asking yourself: Am I excited to get to work today? If the answer is yes more often than not, you're on the right track — and much more likely to find sustainable success.
2. Get comfortable doing it all — until you don't have to
In the early stages, being hands-on in every part of the business is the fastest — and cheapest — way to understand your operations from the inside out. You'll quickly learn what works, what doesn't and what to delegate as you grow. When I started my software company, I relied heavily on my lived experience and basic understanding of accounting, business administration and programming. While many entrepreneurs choose to work with a partner or team from the start to fill in the gaps, I was able to build the software, manage day-to-day operations and grow the business without outside help or funding. This set me up to keep the company entirely bootstrapped, and we still are today.
Today, even with nearly 20 employees, having a diverse skill set continues to serve me. I no longer have to do everything myself, but I can sit in on a development meeting and assess whether projections are realistic. I understand our financial picture and tax liabilities well enough to make informed decisions and keep costs down. Evaluate your own transferable skills and embrace the opportunity to learn what you don't know yet. The all-hands-on-deck approach isn't sustainable forever, but the more you immerse yourself now, the better equipped you'll be to hire, lead and scale with confidence.
Related: 5 Things I Wish Someone Had Told Me Before I Became a CEO
3. Always look for the win-win (or create it)
It has never made sense to me to enter into any business relationship unless both parties leave better for it. There are two outcomes in any negotiation: the objective value (the material outcome of the deal) and the subjective value (how each party feels about the outcome). In my experience, I've learned that subjective value is often far more important because how someone feels about a partnership shapes their openness to working with you again.
I always strive to build long-term relationships with my employees, vendors, partners and customers, so I lean far more on the subjective outcome of any negotiation, prioritizing trust and mutual respect over short-term gains. If you can consistently create outcomes where both parties feel heard, valued and satisfied — even if compromises are made — you'll build a reputation that opens more doors than any one-sided deal ever could.
4. Step up and speak out
If you want to be part of a meeting, a project, an event or a speaking engagement — don't wait to be invited. Early in my career, I often assumed that if people saw value in my work, they would ask me to contribute. But after a decade of climbing the corporate ladder and two more building my own business, I've learned that the most valuable opportunities rarely land in your lap — you have to actively seek them out.
Positioning yourself as a thought leader takes eagerness, interest and the confidence to put yourself forward — even before you feel entirely ready. Whether you're pitching an idea, volunteering to lead or reaching out to collaborate, owning your voice and making it known is a powerful tool to have on hand. Especially for entrepreneurs launching new ventures, visibility and credibility are critical to building brand recognition. The opportunities are out there if you want them — you just have to go after them.
Related: Want to Be an Entrepreneur? Start With These 4 Simple Steps.
5. Lead with honesty and integrity
It may sound simple, but sadly, honesty and integrity are in short supply in today's business environment. To me, these are non-negotiables for building a company that earns long-term trust. Treat your employees, customers, partners and vendors with the same respect and honesty that you'd expect from them. I push my team to take it one step further and go above and beyond to do the right thing for our customers — whether anybody would notice or not. If this standard becomes part of your company culture, over time, it will define your brand.
I believe this leadership approach is one of the core reasons why our employees have an average tenure of eight plus years, why we've maintained the same high-quality vendors for over a decade, and why our customer turnover is exceptionally low. When a customer knows your business operates with such high integrity, they won't turn anywhere else because they know they won't find that level of service anywhere else. In a competitive marketplace, this might just be your strongest differentiator.
No two entrepreneurial journeys are the same, but the foundation you build your business on will shape everything that follows. The lessons will come at you fast, but wisdom only sticks if you're willing to learn as you go. Lead with purpose, stay curious and never stop refining your strategy.