We asked industry experts to share one thing they wish they had done differently in the early days of their business—and what lesson they learned from that experience. Discover strategies that can help you avoid common pitfalls and accelerate your business’ growth.
- Conduct Thorough Due Diligence
- Prioritize Cultural Fit in Hiring
- Build Systems Before Scaling
- Start User Conversations Earlier
- Delegate Tasks to Drive Growth
- Implement Follow-Up Systems
- Use Data-Driven Hiring Practices
- Invest in a Proactive Financial Partner
- Create Sustainable Business Infrastructure
- Narrow Focus for Effective Scaling
- Implement Organized Project Management Systems
- Specialize to Streamline Operations
- Align Offerings with Client Needs
- Price Services Based on Value
- Balance Workload to Prevent Burnout
- Negotiate Shorter Contract Commitments
- Be Selective with Client Partnerships
17 Lessons Small Business Owners Wish They Knew Sooner
Conduct Thorough Due Diligence
Buying a toy business sounded like a dream—until it cost me $1.2 million in just two years. My story isn’t just about loss; it’s about the hard lessons that can save others from the same fate.
My biggest mistake? I let excitement override due diligence. The seller was enthusiastic, but when it came to real numbers, things got fuzzy. I bought the business using vendor finance, assuming cash flow would cover repayments. What I didn’t realize was that the warehouse was full of slow-moving, obsolete stock. The previous owners had bought inventory based on their own tastes, not customer demand.
I skipped proper due diligence, ignored red flags, and didn’t seek expert advice. Even when a bank turned down my loan, I just found another lender instead of asking why. Most of what I paid for was inventory—at cost. In reality, much of it was unsellable. I was stuck with someone else’s problem and no plan to fix it.
Key lessons:
1. Do your homework. Demand clear, independent financials and scrutinize inventory. If most of the price is tied up in stock, make sure it’s stock that will actually sell.
2. Cash flow is king. Don’t assume yesterday’s inventory will pay tomorrow’s bills.
3. Use technology. Inventory management tools could have saved me from costly mistakes.
4. Don’t let ego or optimism blind you. If the numbers don’t add up, walk away.
Today, I help others avoid these pitfalls by promoting smarter inventory planning. If you’re buying a business, don’t fall in love with the idea—fall in love with the numbers. And if you ever end up with a warehouse full of unsellable toys, at least you’ll never run out of birthday presents.
Experience is what you get when you didn’t get what you wanted. Sometimes, that’s the most valuable lesson of all.
Dominic Sutton
Founder, StockTrim
Prioritize Cultural Fit in Hiring
I’ve been a business owner for 18 years (and counting) now, and if there’s one thing I wish I had done differently early on, it was hiring purely for skill without evaluating cultural congruence.
We brought on a few high-performers who looked great on paper and delivered short-term results but didn’t align with our team’s working style or values. Over time, it created friction and slowed down our decision velocity.
Since then, we’ve baked in a values-fit filter into our hiring process. We assess things like communication tempo, feedback tolerance, and default collaborative posture—not just resume highlights. The lesson? You can’t scale a team on output alone. Culture isn’t a soft metric—it’s infrastructure.
Matt Bowman
Founder, Thrive Local
Build Systems Before Scaling
When I started my first business, I was all passion and hustle—burning the midnight oil, wearing every hat, and believing sheer effort would guarantee success. But I soon discovered a brutal truth: hard work alone doesn’t scale.
My biggest regret? Not building systems before scaling.
This mistake cost me time, money, and sanity. But the lesson I learned transformed how I operate. Here’s the breakdown—and how you can avoid the same trap.
Early on, I prided myself on being a “doer.” I handled sales, customer service, operations, and marketing—often on the same day. But as sales grew, so did the chaos:
- Missed deadlines from manual processes
- Customer complaints piling up
- Team confusion due to lack of clear workflows
I’d assumed systems were for “later.” But when a major client deal nearly collapsed from operational disarray, I realized: Growth without infrastructure is self-sabotage.
Why It Happened
- “I’ll Fix It Later” Mindset – Postponing documentation for “urgent” work.
- Underestimating Compound Inefficiency – Small time-wasters (e.g., 10-minute tasks done 5x/day) stole 40+ hours/month.
- Control Fear – Hesitation to delegate or automate.
The Fix: Building a Self-Running Business
1. Document Everything
- Created SOPs (Standard Operating Procedures) for key tasks like onboarding and refunds.
2. Automate the Repeatable
- Zapier for lead follow-ups.
- CRM tools (HubSpot) to track sales pipelines.
3. Delegate Relentlessly
- Hired a virtual assistant for admin tasks.
- Used ClickUp to assign work without micromanaging.
The Result
- 70% fewer customer complaints (clear processes = fewer errors).
- 40% less time spent on busywork (automation handled repetition).
- Revenue grew faster because I focused on strategy, not firefighting.
How to Avoid My Mistake
1. Audit Your Bottlenecks
- Where do you constantly put out fires? That’s your first system to build.
2. Start Small, But Start Now
- Pick one critical process (e.g., invoicing, client onboarding).
- Document it this week—even a rough draft is progress.
3. Use the “10X Rule”
- For every task, ask: “How could this run without me?”
4. Invest in Tools Early
- Project Management: Asana, Trello
- Automation: Zapier, Make.com
- CRM: HubSpot, Keap
Your job isn’t to work IN the business—it’s to build systems that let the business thrive WITHOUT you.
Kunal Verma
CEO, Centre for Fundraising
Start User Conversations Earlier
If I could go back to the early days of building my company, I would stop trying to perfect the product and start talking to users much sooner.
I spent months refining features and improving the resume scoring engine, thinking a better product would naturally drive growth. But people were signing up, stalling out halfway, and not converting. It wasn’t a tech issue. It was a communication gap. When I finally started having direct conversations with users, I realized they weren’t just looking for a tool. They wanted clarity. They wanted to know why their resume needed work and what steps to take next. That insight changed everything. I rebuilt our onboarding, added more guidance, and made the experience feel less like software and more like support. Usage went up and so did retention.
What I learned from this experience is that waiting too long to listen to your end users will make you end up perfecting a product people don’t need. The only way to build something people actually care about is to build it with them, not for them.
Stephen Greet
CEO & Co-Founder, BeamJobs
Delegate Tasks to Drive Growth
I’ve had more than my fair share of “wish I’d done that differently” situations—but there is one that stands out.
Early on, I neglected to focus on delegation at all. I believed that I was keeping costs low and maintaining control, but in fact, I was holding things back. From customer service to marketing to project management—every area was spread too thin, and the consequences were evident. Projects took longer to complete, responses to customers came slowly, and growth came to a halt.
The breakthrough came for me when I chose to hire someone to manage just one thing—our scheduling system. Soon, our booking process was smoother, and customer satisfaction soared. That single modification enlightened me to the potential of delegation—its ability not only to save time but also to drive growth.
Lesson learned: Invest in people earlier. Even a part-time hire or contractor can help. You can’t grow the business without freeing yourself from being the constraint. Delegating doesn’t equate to losing control—it just gives your business space to expand. That is something that I would advise every new founder over a cup of coffee without hesitation.
Evgen Kushnirchuk
Chief Product Officer, CEO, Roof MySpace
Implement Follow-Up Systems
In the early days, I was doing it all—estimating, managing crews, running supply runs, answering the phone, and even chasing down invoices. I thought that was just how it had to be. But the truth is, I was so deep in the day-to-day operations that I couldn’t keep up with the details that matter—follow-ups, callbacks, and quality checks after the job.
There was one client in particular, someone for whom we’d done a full roof the year before. They called about a small issue—nothing major, just a flashing detail that needed to be looked at. I meant to send someone out, but I kept pushing it off, buried under new jobs and emergencies. Weeks passed, and by the time I circled back, they’d already hired someone else to fix it. They never called us again.
It was a gut punch—not because of the lost money, but because I realized I’d let down someone who trusted us. That moment forced me to face the difference between staying busy and actually building something sustainable. After that, I put systems in place—real ones. I hired office help. I built in time for follow-ups and made sure no one fell through the cracks.
The lesson? Doing everything yourself might feel like control, but it can cost you the relationships that matter most.
Dylan Manale
Contractor | Founder, Lone Wolf Roofing
Use Data-Driven Hiring Practices
If I could go back and do one thing differently in the early days of my business, it would be this: I would have trusted the data, not just my gut when I was making hiring decisions.
When you’re an entrepreneur making your first few hires, every decision is magnified. You’re not just adding one more person, you’re doubling your workforce. That hire isn’t a nice-to-have; they’re 50% of your company. And in those moments, it’s easy to lean on instinct, on how someone feels in an interview or whether you “click.”
But what I’ve learned is that instincts can be misleading. You don’t need just a good vibe. You need competence, alignment, potential, and a solid idea of what it actually takes to be successful in the position. And that’s where data comes in.
Today, I hire with structure. I use clear role definitions, competency data, and proven success indicators. Because when you’re building something from the ground up, every person counts, and every mismatch costs more than just time. It costs momentum, culture, and trust.
The lesson? Confident hiring isn’t about guessing or instinct. It’s about knowing. Know who you need. Know what success looks like. And use tools like competency assessments that give you a full picture of a candidate, not just a first impression.
Linda Scorzo
CEO, Hiring Indicators
Invest in a Proactive Financial Partner
In the early days of my business, I wish I had brought in a proper accountant much sooner. Not just someone to do the books or file the returns, but someone I fully trusted to give me the best advice on how to structure the business, manage cash flow, and stay on top of our financial strategy. I naively assumed that a decent cloud-based tool and a bit of common sense would be enough. But looking back, I was underestimating just how much pressure cash flow can create when you’re trying to grow a business, pay yourself and a team, and invest in marketing and operations all at once.
The accountant I first worked with was more reactive than proactive. They did what I asked, but never advised on what I should be doing. I didn’t realize until later that what I really needed was a financial partner who’d challenge me, flag risks before they became problems, and help me make better decisions on everything from pricing to forecasting. When I eventually found the right person, the difference was night and day.
The lesson is that trust and quality in that role are everything. If I could go back, I’d invest more time in finding someone who not only understood the numbers but also understood my ambitions and had the experience to help me reach them. A good accountant doesn’t just save you money; they give you clarity and confidence.
Adam Whittaker
CEO, Manifest New Business Ltd
Create Sustainable Business Infrastructure
Passion Is Fuel. Systems Are the Engine.
The shift that helped me scale without sacrificing purpose or peace.
I knew how to lead others. What I didn’t know—yet—was how to lead a business built around me.
That was the wake-up call in the early days of launching my consulting company. After decades of success leading schools, turning around struggling districts, coaching high-level executives, and building award-winning teams—I thought I was ready. I had relationships, results, and a reputation for delivering real change. But when I stepped into business ownership, I quickly realized that being good at the work doesn’t automatically mean you’re set up to grow the work.
I hit the ground running. I took on every opportunity. I customized every offer. I gave every client everything I had. And while that earned early wins, it wasn’t sustainable.
I had built momentum—but not structure.
Lesson one: Working in the business is not the same as working on the business.
Lesson two: Stop trying to do it all alone.
There’s a trap many early-stage entrepreneurs fall into—we believe that hustle is the holy grail. That if we just work harder, longer, and smarter, we’ll break through. But I learned the hard way that hustle without structure leads to burnout, bottlenecks, and blurred boundaries.
So I made the shift.
I clarified my offers. I built workflows and automations. I brought on people with the right skills and tools to do what I couldn’t—or shouldn’t—do alone. I invested in infrastructure so I could lead my business like I’d led every high-performing team before: with vision, focus, and intention.
That decision changed everything.
Now, I coach and consult at scale. My business doesn’t just reflect my values—it runs on them. And most importantly, it allows me to focus on the work that fuels me: deep coaching, strategic thinking, visionary planning, and meaningful connection.
Because of the systems and support I’ve built, I’m more engaged, focused, and fully present in every interaction. I no longer operate from a place of exhaustion—I lead from a place of alignment.
So here’s my message to fellow entrepreneurs: Passion will get you moving. But systems will keep you going.
Don’t build a business just to stay busy. Build a business that’s sustainable, scalable, and deeply aligned with who you are and what you’re here to do.
Because the goal isn’t to do everything.
The goal is to build something that actually works—without breaking you.
Gearl Loden
Leadership Consultant/Speaker, Loden Leadership + Consulting
Narrow Focus for Effective Scaling
I’ve built five companies, and if I could go back to the beginning of my first one, I would have narrowed my focus much earlier instead of trying to serve everyone who showed interest.
In those early days, I believed that saying yes to every project was the smart move. I thought more clients meant more revenue, and more revenue meant growth. But what actually happened was the opposite. Every new client type came with a different set of needs. That forced me to reinvent my playbook every time. It made it harder to create repeatable systems, harder to market effectively, and harder to deliver consistent value. I was chasing growth, but I was building nothing.
The turning point came when I got honest about who I could help best. I defined a specific customer, a specific problem, and shaped my offers around that. From that moment on, everything got easier. The right clients started finding me, my systems became sharper, and I was able to scale with less stress and more control.
In simplest terms: When you try to help everyone, your value gets watered down. But when you commit to solving one problem really well, you create clarity, and that clarity is what will allow your business to scale.
Jeff Mains
Founder and CEO, Champion Leadership Group
Implement Organized Project Management Systems
Since leaving the military in 2014, I’ve started three very different businesses—an FMCG brand, a self-care subscription box, and now, a digital marketing company.
The biggest lesson I’ve carried from the first two? Don’t build your business inside your own head.
This time around, I hired an organizational coach early on to help me set up business systems in a project management tool. No more scribbled notes, endless Google Docs, or chaotic to-do lists on the back of old to-do lists. Everything now lives in one place. Every offer, every piece of content, every recurring task—all broken down into bite-sized, manageable steps, each with deadlines and ownership.
It sounds simple, but it’s completely changed how I operate. Now, instead of feeling like I’m constantly reacting or scrambling to remember what I said I’d do, I open my PM tool and it’s all right there. Launches feel doable—I can see deadlines weeks out. I know what I have to do daily, as the bare minimum, to move my business forward, so when school holidays hit or I have a sick kid, my business isn’t derailed. I can roll with the punches.
Smart, strategic systems early on = peace of mind, better decisions, and more momentum.
Alexandra Johnson
Founder, She’s a Peach
Specialize to Streamline Operations
I believe one of the biggest mistakes we made early on was trying to serve everyone instead of narrowing our focus. We took on clients across too many industries with wildly different needs, thinking more variety meant more opportunity. In reality, it stretched our resources thin and diluted the quality of our work.
The turning point came when we decided to specialize in content for B2B tech and SaaS companies. Once we focused, everything got easier: our messaging clicked, our workflows streamlined, and referrals doubled. We became known for something specific, not just “content in general.”
The lesson? Clarity beats range in the beginning. But now, with the right team and infrastructure in place, we are able to manage a broad mix of industries confidently and effectively. What used to feel chaotic now runs with clarity and purpose because we grew into it the right way.
Vaibhav Kishnani
Founder & CEO, Content-Whale
Align Offerings with Client Needs
If there’s one thing I would approach differently, it would be how long I held onto the idea that strategy alone could scale a business. In the early years, I leaned heavily on my experience as a consultant—delivering advice, not execution. We saw some success, but when our largest client walked away, it exposed the fragility of that model. It forced me to lay off the entire team.
That moment, while difficult, was also clarifying. Talking with past clients, I realized they didn’t just need direction; they needed execution. That insight sparked a shift from consulting to a full-service sales delivery model. We started offering end-to-end outbound sales packages, and the response was immediate. That’s when we truly started to scale.
The lesson? Build for real-world needs, not just your expertise. Once we aligned our offering with what our clients actually needed to grow, everything changed.
Vito Vishnepolsky
Founder and Director, Martal Group
Price Services Based on Value
One thing I wish I had done differently in the early days was charge more—sooner.
I priced based on fear, not value. I told myself I needed to “earn trust first” or “build a portfolio,” but all I did was train clients to expect high quality for low cost. That put me on a treadmill—busy, booked, and underpaid.
The lesson? Undervaluing your work doesn’t lead to more opportunity—it leads to burnout. The right clients don’t want cheap. They want clear outcomes, real support, and someone who respects their own time and energy.
Once I raised my prices to match the impact, everything changed. Fewer clients, better relationships, more margin to actually grow the business. If you’re good at what you do, the sooner you reflect that in your pricing, the faster you’ll attract the people who see it too.
John Mac
Serial Entrepreneur, UNIBATT
Balance Workload to Prevent Burnout
I wish I hadn’t stretched myself so thin! I think this is unfortunately a pretty common experience for CEOs and startup teams. There is a difficult balance to strike between expanding your team to have enough people to take on all the work and not hiring too many people prematurely in case things don’t pan out as you hope. To deal with the latter, I definitely took on a lot more work and responsibilities in those early days, which made me feel pretty burnt out. When you’re burnt out, you can’t do your best work, and I learned that the hard way!
Seamus Nally
CEO, TurboTenant
Negotiate Shorter Contract Commitments
I would have pushed really hard for no mandatory minimum length on contracts, or to shorten mandatory minimum lengths on contracts. I’ve done extra due diligence before signing or working with a firm. If you sign a $5,000 a month agreement with somebody, and you’re locked in for 12 months, then they’ve essentially guaranteed themselves $60,000, whereas with a three-month contract, you’re capping your potential loss to $15,000.
Christian Perry
CEO, Undetectable AI
Be Selective with Client Partnerships
One thing I wish I had done differently in the early days of my business was getting clearer on the type of clients we wanted to work with and being braver about saying no to the wrong ones.
Think of it like this: if you’re a luxury car dealership and a rusty old banger rolls in asking for work, and you say yes, you’re sending a message: “This is the kind of vehicle we serve.” People see it in your yard, they tell their friends, and before you know it, your reputation is built around fixing rusty cars instead of selling high-performance ones.
It’s incredibly hard to say no when you’ve got a mammoth payroll staring you down every month. I was so focused on making ends meet and hitting sales targets that I often said yes to clients who weren’t aligned with our values, lacked growth potential, or simply weren’t the right fit—just to prove we could win the work or avoid short-term revenue gaps.
Those projects filled the pipeline, but they drained the team, diluted the brand, and distracted us from the work that really lit us up.
The lesson? Growth isn’t just about more. It’s about better. Being selective isn’t arrogance; it’s strategy. Once we narrowed our focus and got ruthless about fit, we did our best work, our team thrived, and the business scaled far more sustainably.
Kathryn Strachan
Author, Scaling Success: How to Build Brands that Break Barriers
