10 Entrepreneurs on the Mistakes That Ultimately Made Their Businesses Stronger
Every entrepreneur has a moment they would rather forget. A rushed deal. A mishandled launch. A system trusted for too long. At the time, these moments feel like pure failure, expensive, stressful, and sometimes career-defining in the worst possible way.
But when you talk to experienced founders, a different pattern emerges. The mistakes that hurt the most often become the ones that reshape how the business operates. They force better systems, clearer positioning, stronger boundaries, and more resilient models. In hindsight, many entrepreneurs trace their long-term success back to a decision that went wrong.
To understand how those turning points actually unfold, we asked entrepreneurs to share the business mistakes that changed everything for them. Their stories span partnerships, pricing, marketing, product launches, financial oversight, and growth strategy. In each case, the failure exposed a weakness that could no longer be ignored.
1. Rushing Into a Major Partnership Without Proper Vetting
Our biggest failure happened about 15 years into running Altraco when we took on a major Fortune 500 client without properly vetting a new factory relationship in Southeast Asia. The factory promised capabilities they didn’t have, and we didn’t do our usual deep due diligence because we were rushing to meet the client’s timeline. We ended up with 40,000 defective units sitting in a warehouse and nearly lost a $2M account.
That disaster completely changed how we operate. We now require in-person factory visits before any new partnership, no exceptions, even if it means saying no to opportunities. We also implemented multiple-point testing throughout production instead of just final inspection, which catches problems when they’re fixable instead of catastrophic. Our on-time delivery rate is now 99.6%, specifically because we learned to slow down the front end.
The counterintuitive lesson was that saying “no” or “not yet” to clients became our competitive advantage. When prospects push for faster timelines than our vetting process allows, we walk them through exactly what happened with those 40,000 units. Most choose to wait. The ones who don’t usually come back a year later after getting burned elsewhere.
That one failure cost us about $180K in air freight, rework, and lost margin, but it saved us from becoming another commodity sourcing company that just connects clients to factories and hopes for the best.
Albert Brenner, Co-Owner, Altraco
2. Pouring Money Into Ads Before the Business Was Ready
I spent tens of thousands of dollars on Meta ads when I first launched, trying to force growth before my business was actually ready for it. The result was brutal: traffic, lots of it, conversions, zero.
At the time, IG business guru influencers had me believing Meta ads were the shortcut. What I didn’t realize was that ads only amplify what already exists. I hadn’t built a site that converted, a message that clearly explained why we were different, or the kind of trust parents need before buying something for their kids.
That failure forced me to stop chasing quick success and start building fundamentals: a site designed around real customer questions, deep educational content, and long-term SEO instead of quick wins. I rebuilt the business from the ground up with conversion, clarity, and trust at the center.
Today, the majority of our traffic is organic, our customers arrive already aligned with our values, and we have a real, sustainable business, not one propped up solely by ad spend. Losing that money was painful, but it taught me a lesson I now share with every founder I meet: ads don’t create businesses, foundations do.
Anastasia Vasilieva, Sustainable Fashion Brand Founder, Treehouse
3. Undervaluing My Work by Failing to Ask for What It Was Worth
My journey of entrepreneurship started when I made a huge mistake. After completing several rounds of interviews for a job, it was time to discuss compensation. I knew I was undervalued at the place I was working at the time. I was making 40-something thousand and knew that I should have been making mid-50-something thousand. So, I decided an annual salary of 60,000 was my minimum. I would ask for 68, be thrilled with 65, but still accept 60.
So when the recruiter called me to discuss compensation, I repeated in my head, “68. 68. 68.”
I was already nervous to ask for this amount. Nobody likes negotiating salary, and in the place I was working, I had my completed and signed contract ripped up in front of me and was handed a lower salary (yes, it was illegal).
Then, instead of the expected question of annual salary, the recruiter asked for my hourly rate as a contractor.
I blurted out the number I had been practicing. “68.”
He went quiet and did some calculations. “Hmm, so that comes to about $130,000 a year.”
Luckily we were on the phone, because if we were on a video call, he would have seen me go bright red with a dropped-jaw.
“Well, when you put it like that…” I started to say.
He said, “I’ll talk to the hiring manager and see what he says.”
We hung up, and I threw myself on the couch, shaking my head. I couldn’t believe I just asked for $100,000. That was more than twice what I was making! Who did I think I was?! I totally blew it.
A few days later, prepared to apologize and ask for a more reasonable number, the recruiter called me back and offered 62. That came out to around $120,000.
I was in shock, but elated. That moment really solidified it for me. The world reacts to how you show up in it.
If I had said the number I thought I was worth, I would have gotten half of what the employer would have valued me at.
If I had undersold myself like that, the hiring manager may have also seen me as less valuable.
I would have shown up as less valuable and continued to be seen as less valuable.
Cluelessly continuing the same job negotiation, the recruiter asked if I was registered as a sole proprietor or a corporation.
The recruiter suggested I register as a Corporation.
By the end of this very cluelessly-entered negotiation, I was a 6-figure business owner.
Making this mistake created a 6-figure business owner. It taught me to show up as if I was worth more than I believed — and that, when I did, the world agreed!
Roxanne Nicolussi, Founder, The Big Bold Consulting Company
4. Assuming Visibility Alone Was Enough to Protect the Business
One failure that became a turning point for my business was assuming that visibility lived in platforms rather than in identity.
Early on, I invested heavily in content and distribution without fully protecting the identity architecture behind it. When a major disruption hit and impersonation sites appeared, I realized that what I had built was visible, but not resilient. Traditional takedowns were slow, and platform control alone wasn’t enough.
That failure forced a reset. I stopped optimizing for reach and started building for recognition. Instead of chasing channels, I focused on establishing a stable, authoritative identity that AI systems and search layers could consistently recognize as canonical.
That shift changed everything. As my work became visible across AI systems, that visibility also became protection. When false versions surfaced, the real signal surfaced faster. Authority resolved confusion before enforcement ever could.
The result was a fundamentally different business. Recovery didn’t require starting over, because the identity signal already existed. Today, everything I build is anchored in the same principle: growth compounds fastest when your business is recognized for who it is, not just where it appears.
What initially felt like a failure became the moment I built something durable instead of merely visible.
Susye Weng-Reeder, Founder and CEO, Susye Weng-Reeder, LLC
5. Skipping Customer Validation Before a Major Product Launch
LINQ Kitchen’s major misstep occurred after we introduced our new luxury cabinet product line, which we thought would be enough to differentiate us from other competitors. However, due to overconfidence, we bypassed the normal process of sampling the new product with a small number of customers before its mass distribution. When we did receive some of the first customer comments about the new cabinets, the results were unimpressive. Customers reported problems with functional performance and significant discrepancies between the product’s price point and what they expected to pay. Due to negative customer response and rising inventory levels, we faced considerable backlash.
As a result of these failures, we decided to revise our product development methodology completely. Rather than adopting an overly rigid development cycle, we adopted a “test & learn” development process that allows us to create prototypes and collect real-time feedback from consumers before fully launching the final version of the product. The way we responded to our customers made a new dynamic within the company, giving us a direct line of communication with our consumers and enabling us to incorporate their opinions into our offerings. The lessons learned from this experience have significantly altered how we develop products, leading to more successful product launches, a better understanding of our consumers, and a more precise understanding that incorporating consumers into the product development process is no longer optional for long-term, sustainable business growth.
Josh Qian, COO and Co-Founder, LINQ
6. Building the Business on a Single Sales Channel
One of the biggest turning points for my business came from what felt like a failure at the time: relying too heavily on a single sales channel—Amazon.
Early on, my products gained traction quickly, and it felt like a golden ticket. But without warning, Amazon removed listings I had invested months into developing, leaving me scrambling and losing revenue overnight.
That was a real setback, and at first it felt like a failure. But it forced me to rethink how I was building my business. I realized I hadn’t created a sustainable brand—I had built dependence on one platform. That experience pushed me to build our own ecommerce presence and expand into a curated marketplace for women-focused wellness brands. That pivot, born from a painful failure, ultimately made Bona Dea Naturals stronger and more resilient.
Jessica Rich, Owner, Bona Dea Naturals
7. Competing on Price Instead of Value
What shook my confidence was the “Race to the Bottom” disaster. I started out under-pricing all competitors in an attempt to gain market share. Instead of fast growth, I landed diva clients with peanuts budgets that were sucking us dry. We are killing ourselves and hardly getting ahead, barely breaking even that almost led to an all-out collapse.
This forced us to Premium-Position. We doubled our fees and sold nothing but high-value outcomes. And to my astonishment, as we drew in higher-quality clients who valued our expert abilities, sales began to rise. That failure showed me that your price does not just determine who can pay you; it determines the entirety of the types of clients that you have.
Geremy Yamamoto, Founder, Eazy House Sale
8. Building a Business Model That Wasn’t Sustainable Long-Term
One failure that became a turning point for me was realizing I had built a version of “success” that looked impressive externally but wasn’t sustainable internally. I overcommitted: too many projects, too much pressure to perform, and a pace that quietly normalized burnout until I hit a wall and had to admit my systems weren’t designed to support the life I wanted. That moment forced me to rebuild my business around clarity and leverage: tighter positioning, clearer boundaries, and repeatable frameworks rather than constant reinvention. The failure wasn’t the workload—it was the model—and changing it became the foundation for everything I’m building now.
Kristin Marquet, Founder & Creative Director, Marquet Media
9. Prioritizing Growth Tactics Over Listening to the Community
One early failure was focusing too much on growth tactics instead of the people we were trying to serve. We chased trends and visibility before fully listening to our community, and engagement suffered as a result. That turning point forced us to slow down, put our customers at the center of every decision, and build based on real needs. Once we led with community first, clarity followed, trust grew, and the business began to move forward sustainably.
Mandi St. Germaine, Co-Founder, MBS | The Woman Beyond the Cape
10. Handing Off Financial Oversight Without Enough Accountability
One significant failure that became a turning point for my business was related to tax issues caused by the accounting practices I entrusted to a CPA and bookkeeping service. This resulted in substantial financial problems, including levies and legal complications. It was a challenging experience, but it taught me the importance of diligent financial management and thorough oversight, ultimately helping me to implement better practices moving forward.
Aleina Almeida, CEO, Meridian International Sourcing Group
What stands out across these stories is how founders responded once the damage was clear. The turning point was rarely the failure itself. It was the decision to slow down, reassess assumptions, and rebuild with intention instead of urgency.
In many cases, the lesson was counterintuitive. Saying no became an advantage. Raising prices attracted better clients. Focusing less on growth created more stability. Letting go of control in the wrong areas exposed where control actually mattered most.
For entrepreneurs reading these stories, the takeaway is not to avoid mistakes at all costs. That is rarely possible. The real risk is repeating them or refusing to learn from them. The founders featured here didn’t just recover from failure. They used it to build businesses that were clearer, stronger, and far more resilient than what existed before.
