A few years after university, I co-founded a startup to build a low-cost smartphone called Frank. The idea was to create a budget-friendly phone that challenged the industry giants, not just on price, but with a brand that stood for something. We marketed it as "Frankly, just a phone", a no-nonsense, anti-status-symbol device that could do everything people actually needed. And at first, it worked. Our crowdfunding campaign took off. We had a story, momentum, and a surprising amount of media attention. But behind the scenes, we were unravelling. We weren't a team. We were a collection of individuals moonlighting on a side hustle with no infrastructure. I had never built a team from scratch before. We recruited friends, made decisions fast, and tried to lead with vision alone, but without clear roles, systems, or accountability. We pushed back our launch date. Then again. And again. When we finally launched, our campaign looked polished, but everything under the hood was fragile. Then the pressure hit. Our product guy had miscommunicated specs. Our software wasn't ready. Our marketing team oversold features. We were bending under the weight of our own hype, and I to be honest with myself I didn't lead us through it well. I was pushy on timelines, headstrong about progress, and reactive instead of reflective. When conflict started brewing between team members, I didn't step in early enough. When cracks appeared, I tried to patch instead of pausing. Eventually, we refunded the majority of the funds and shut the project down. Two years of work. Over $80,000 of personal investment. Gone. But here's the lesson: A vision isn't enough. Leadership is about building the conditions for execution, not just inspiration. Frank failed not because we lacked purpose, but because we lacked structure. Trust. Feedback loops. Clarity. I learned the hard way that empowering people isn't just about handing them a title or task. It's about shaping a team that can communicate under pressure, adapt to change, and self-correct when things start to slip. That experience reshaped how I lead today. Because failure doesn't mean you're not a leader. It means it's time to learn how to lead differently.
Early in my career, I made the mistake of trying to do everything myself. When I started the Justin Landis Group, I felt that clients expected me to handle every detail of their real estate journey personally. I thought that was the only way to prove my value. It worked for a while, but eventually the pace became unsustainable. I was exhausted and the quality of my leadership suffered. Houses were still getting bought and sold, but I knew I wasn't building a team that could thrive long term. That was my failure. The lesson was clear: leadership isn't about being the hero in every transaction, it's about creating an environment where others can lead and succeed. Once I embraced that, I began empowering my team to step into bigger roles. I focused on training, trust, and letting go of control. The change was immediate. Clients still received exceptional service, and the group became stronger than anything I could have built alone. That experience taught me that building a great business in real estate means building people first. Houses may be the product, but the team is the foundation. Leadership is about trust, and that trust multiplies results.
I once promoted a person to management simply because they were my top producer. I thought being a star performer made them a top candidate to lead. Within two weeks, my DMs were blowing up, three staff members were threatening to quit, and I was $15,000 into bonuses, marketing disasters, and rehiring costs. The issue was I let my production numbers blind me to emotional intelligence and cultural awareness. I would go so far as to say leadership is never about "who earns the most" — it is about who can walk into a 10-minute hallway meltdown and de-escalate without being condescending or defensive. The lesson I learned is this: technical expertise does not scale culture. I now insist every manager prospect shadow frontline work for 30 hours before their first meeting or title. The second someone thinks they are above wiping a counter or answering a phone call, they are gone. Leadership is not glamorous because it is more about being the human trash can for everyone else's bad day and doing it with grace. Ever since I changed my mindset, turnover is under 8 percent and team reviews have increased by 300 percent. So much for "just promote the top producer."
Looking back on DataNumen's early days, one of our most significant failures became our most valuable lesson about leadership and market understanding. When we first started our business, I was confident that our technical expertise would naturally translate to business success. We developed and launched three products sequentially - UniView image browser, DLL to Lib development tool, and Advanced Zip Repair. The first two had disappointing sales, but I attributed this to inappropriate product type. The real wake-up call came with Advanced Zip Repair. Despite being a solid technical solution for corrupted ZIP files, we sold only 3 copies in the first six months. I was devastated and honestly considered not running business by selling software any more. As a technically-minded founder, I had fallen into the trap of believing that superior technology would automatically find its market. Facing what seemed like inevitable failure, I made one last desperate attempt. Instead of abandoning the product entirely, I decided to experiment with a different business model. The results were stunning - sales jumped from 3 copies in six months to over $600 in the very first month after the change. By the second year, we had consistent monthly revenue of over $2,000 from this single product. This experience taught me the most crucial leadership lesson of my career: technical excellence means nothing without market understanding. As a leader, I learned that my role isn't just to drive product development, but to bridge the gap between what we can build and what customers actually need and want to buy. This failure fundamentally shifted DataNumen's approach. We evolved from being purely technology-focused to balancing technical innovation with deep market insight. That first successful product became our foundation, and the lesson learned shaped our entire business philosophy moving forward - always validate market demand alongside technical capability. The invisible hand of the market taught me that sometimes the smallest adjustments in approach can yield extraordinary results, but only if you're humble enough to listen and adapt rather than stubbornly pushing forward with your original assumptions.
A big and painful failure from early in building Reclaim247 is an underestimation of how difficult it is to scale so quickly. We had built a good system around car finance and automotive claims, and as we began to take clients, demand grew far quicker than we had originally planned for. We had been thrilled to onboard as many clients as we could and sustain ourselves with demand, but we had scaled the business and grown operations far faster than our internal systems could keep up with the demand. On paper, it looked like success: revenue was up, inquiries were flowing. But behind the scenes, the cracks were obvious. Cases took longer to process, communication slipped, and a few clients felt the impact. Back then, I was relying on brute force and long hours to compensate for shortcomings. I learned in a rather unpleasant way that leadership is less about doing it all yourself or grinding harder. Instead, it's about building the right systems, being transparent when plans fall through and safeguarding the trust of your constituents. We had to slow down, re-engineer workflows, and put more emphasis on staff training and client updates before scaling again. The most important lesson was that leadership requires humility. Making mistakes is not fatal when you take ownership fast, speak candidly and use this to form a blueprint to improve. Ever since, I have made a personal rule for myself to only ever work towards sustainable growth and to make decisions with the team, rather than make decisions and then set out to reach higher and higher numbers. This has helped us not only to fortify our operation, but also made the culture of accountability and trust even more entrenched at Reclaim247. In retrospect, that failure was a blessing. It made me realise that growth at all costs is not sustainable growth. Sustainable growth is growth with resilience. Resilient growth is long-term growth that has been built on trust and well thought-out processes.
Failure is often painted as the opposite of success, but in entrepreneurship, it's a crucial part of the journey. Every misstep carries a lesson that shapes how we lead and grow. One of my most defining failures wasn't about losing money or missing a market opportunity—it was about how I underestimated the importance of transparent communication with my team. That experience reshaped my entire approach to leadership. In the early stages of building my business, I made a critical mistake: I kept challenges and setbacks to myself, believing I was protecting my team from unnecessary stress. My intention was good, but the result was damaging. When problems eventually surfaced, employees felt blindsided and disengaged. They told me later that they would have preferred to be informed earlier, even if the news was tough, because it would have given them a chance to help. The failure wasn't the setback itself—it was failing to trust my team enough to bring them into the problem-solving process. A turning point came when a product launch missed its target date due to supply chain delays. I initially chose to keep the details quiet, hoping to resolve it quickly. But when deadlines slipped further, the lack of transparency eroded confidence. After that experience, I began holding regular update meetings—even when the update was "we're still working through challenges." Surprisingly, this built more trust, not less. My team felt valued, respected, and empowered to contribute ideas. That shift improved collaboration and morale, even during setbacks. Research from Harvard Business Review emphasizes that transparency is a key driver of employee trust and engagement. Teams who feel informed and included are more likely to stay motivated and contribute solutions during crises. Conversely, withholding information—even with good intentions—creates uncertainty and disengagement. That early failure taught me the importance of trusting my team with the whole truth, even when the truth is uncomfortable. Leadership is not about carrying the burden alone—it's about creating space for shared ownership of challenges and solutions. Since embracing transparency, I've found that failures no longer fracture our momentum; instead, they become opportunities to strengthen collaboration. The most important lesson? Great leaders don't just celebrate wins with their teams—they invite them into the struggles, too.
I waited too long to grow. I kept holding off on hiring, telling myself I was waiting for the "perfect" moment. This slowed us down, burned out the team, and meant we missed a few great opportunities we just couldn't staff in time. What I learned is that leadership is not about perfect timing, it is about making clear bets and owning the results. Now I keep it simple: when pipeline and workload hit certain thresholds, we hire. We run 90-day growth plans with clear owners, budgets, and success metrics, and we check in every week. My advice to new owners is this: stop chasing certainty. Make the call with enough information, not all of it. Set some guardrails, share the plan, and move. You can always adjust a decision in motion, but you cannot steer a parked car.
Failure happens just about every day when you run a business. I don't mean that in a negative way...it's just part of the job. I would say almost all business owners learn how to run a business through daily trial and error. Some failures sting for a minute and fade away, but the ones that really teach you something are usually about people, not profits. For me, it was my employees where it seemed I failed the most, and learned my most valuable lessons. I've had moments where I thought I saw a situation clearly, someone made a mistake, something felt off, and I reacted based on what I knew at the time. But with experience, I learned things are rarely that simple. Sometimes years go by before you really understand what was happening behind the scenes. What that's taught me is to slow down and handle those moments with care. Be patient. Be fair. Even if you don't have all the details, treat people with respect so that, years later, you can look back and say, "Given what I knew then, I handled that as well as I could." When you build a team that trusts you and a culture that values understanding over snap judgments, everything gets stronger...the relationships, the morale, and the business itself. Because at the end of the day, a great company isn't built on flawless execution; it's built on people who feel seen, respected, and supported, even when things get messy. And where that success starts is with me.
Early in the development stage of my real estate company, I underestimated the speed at which little inefficiencies develop into massive setbacks. When our staff started assisting more clients with purchases and sales in various markets, our systems were not keeping pace. I was so intent on expansion that I neglected what it takes to maintain it. The absence of systems resulted in communication breakdowns, redundant work, and undue stress. It was not a single large error; it was a series of small ones generated by failing to slow down to lay a solid groundwork. The experience taught me that leadership is not scaling; leadership is making clarity. Real estate transactions are complex and emotional, and if your back-end operations do not equal the front-end promise, leadership fails. When I invested in training, technology, and structured workflows, my team was better able to spend its time on customer relationships and less on internal conflict. That adjustment raised our performance and culture in ways revenue alone never could.
A key failure in my entrepreneurial journey was launching a service without properly gauging market demand. Despite our team's dedication, the offering fell short, causing financial losses and reputation setbacks. This taught me the critical value of market research and the need for adaptability as a leader. You don't learn to walk by following rules. You learn by doing, and by falling over. I learned that as a leader, it is essential to listen to your customers, understand their needs, and be willing to pivot quickly based on feedback and market trends. By being open to change and continuously evaluating our strategies, we can stay agile and better meet the evolving needs of our customers.
A specific failure in my entrepreneurial journey was taking on too many projects at once without enough resources to deliver at our usual standard. Deadlines slipped, quality dropped, and it caused unnecessary stress for the team and the clients. The most important lesson it taught me about leadership was the need to set realistic capacity limits and communicate them clearly. Saying no or delaying a start date can be better than risking a rushed job that hurts relationships and reputation. Since then I've focused on careful project planning and honest timelines, which has improved client trust and kept the team motivated and confident in our work.
One of the biggest mistakes I made in my entrepreneurial journey was becoming a business coach for the wrong reasons. On the surface, it looked like ambition. But underneath, my subconscious driver was a need for approval — from my father, from society, from the image of being seen as "elite" or "capable." I equated money-making and entrepreneurship with worthiness. Because of that, I ran my business from an ego-driven script rather than an integrated one. Every rejection felt like a reflection of my inadequacy. Each "no" paralyzed me, fueling imposter syndrome. I avoided marketing, second-guessed myself constantly, and as a result, my business stagnated. The turning point came when I confronted my subconscious patterns. I began the deep work of rewiring my identity — shifting from someone who needed external validation to someone who recognized their inherent worth. Instead of chasing approval, I chose alignment with my true calling: helping others uncover their own subconscious scripts so they could find freedom from procrastination, self-criticism, and distraction. That shift transformed not only my business, but also my leadership. I learned that real leadership is not about image; it's about integrity. When I stopped fearing rejection and started leading from authenticity, I finally began marketing with confidence, attracting more clients, and making a greater impact. The lesson: if you lead from ego, you end up drained and stuck; but if you lead from authenticity, you create sustainable success.
In 2018, I started a web agency in Copenhagen and moved to Lisbon, Portugal, to grow it even more. We grew it to 10 employees and multiple clients, and it was all going great; at least, that's what it felt like. We signed for a new office and negotiated the contract period to one year. The month after, we realised how bad everything was looking, and we had to close everything down in a proper manner. It was something that really hit me hard, and I spent a long time trying to get over it. We had multiple colleagues whom we had to lay off. We were stuck with an office we never even got the keys to, but we had to pay for a year, and we had a super low income. We managed to get through it without going bankrupt, but I went down with stress, and it was a horrible period. All of this happened within a year, so it all went very fast, and we made so many mistakes. Looking back at it today, the number one lesson I take with me from this is: don't hire too fast. Back then, we hired and hired like we had way more work than we did, and we thought, Why not? Today, I do it very differently. I start by trying to automate as much as I can to free up time, and when I hit a limit after the automations, then I look into hiring, but not before that.
At the early developmental stage of our business, I rushed into a new city and expanded too quickly without a properly onboarded and trained local team. I thought enthusiasm and hustle are going to make up for a lack of systems and organized processes. The outcome of that experience was missed appointments, unhappy customers, and a valuable leadership lesson. I learned that scaling doesn't just happen because of opportunity; it takes preparation. As a leader, I came to understand that my job is not to push for growth at all costs, but rather make sure the people in-operation have the tools, processes, and confidence to deliver. I have never opened a new market since then without first investing in training and clear communication. That valuation helped me to establish my approach as a leader - having patience, structure and focus on empowering others to deliver before advancing.
Back in 2003, I convinced my entire team at CC&A to pivot from our successful HTML/Flash web development into what I was certain would be the "next big thing" - interactive CD-ROM presentations for corporate training. I was so confident in this direction that I had us turn down three major website projects to focus exclusively on this pivot. Within six months, broadband internet adoption exploded and streaming video made CD-ROMs obsolete almost overnight. We lost roughly 60% of our revenue that quarter and I had to let go two talented developers who'd been with us since the beginning. The failure taught me that leadership means balancing vision with pragmatism - never abandon your core competency until the new direction proves viable. Now when I see emerging trends, I test them as side projects while maintaining our bread-and-butter services. This approach later helped us successfully transition into SEO and digital marketing without risking the company. Most importantly, I learned to include my team in strategic decisions rather than making unilateral pivots. Their technical insights often spot implementation challenges I miss from the business side, and they're more invested in changes they help shape.
I learned the hard way about delegation when I tried to personally quality-check every single cake during our busiest Valentine's week. We had over 200 orders that week, and I insisted on approving each one before it left our Kings Cross kitchen. By day three, I'd created a massive bottleneck. Orders were backing up, my cake artists were waiting around for my approval instead of creating, and we missed 15 delivery windows. One corporate client's anniversary cake arrived 3 hours late to their event, and they posted about it on social media. That failure taught me that micromanaging doesn't equal quality control--it kills it. Real leadership means building systems your team can execute without you being the chokepoint. I immediately implemented quality checkpoints where our experienced decorators could approve their own work and their teammates' work. Now we fulfill over 50,000 orders annually because I learned to trust the people I hired. The best leaders make themselves replaceable in daily operations so they can focus on growing the business instead of strangling it.
After 15 years in SEO, my biggest failure happened when I launched an AI-powered content tool for SiteRank in 2023 without properly testing it with real client workflows. I was so excited about the technology that I rolled it out to 12 major clients simultaneously, promising 300% faster content creation. The tool worked beautifully in isolation but completely broke down when integrated with existing client systems. We had content formatting issues, keyword density problems, and worst of all--some AI-generated content actually hurt client rankings because it wasn't properly optimized for their specific niches. I had to personally call each affected client, take full responsibility, and spend three months fixing their campaigns manually while our team rebuilt the tool from scratch. We lost two major accounts and nearly $40K in revenue that quarter. The lesson was brutal but invaluable: as a leader, your excitement about innovation means nothing if you don't validate it through your team's eyes first. Now every new AI tool or process gets tested with our most experienced SEO specialists before any client sees it. My team has veto power over launches, which has prevented three similar disasters since then.
My biggest failure happened during my transition from solar sales to roofing in Idaho. I took on three major commercial projects in my first six months, convinced my solar sales experience meant I could handle any timeline pressure. All three jobs had weather delays, and instead of communicating proactively with clients, I kept promising we'd catch up - classic sales guy mistake. The breaking point came when a warehouse owner had to delay their grand opening because our TPO installation ran 10 days behind schedule. I lost that contract and nearly killed High Country Exteriors before it really started. The other two clients stuck with us but at reduced margins after I had to bring in emergency crews. The lesson wasn't about project management - it was about honest leadership. In solar sales, you could smooth-talk delays because installations were usually flexible. Roofing clients have hard deadlines tied to weather windows and business operations. Now I tell clients the worst-case scenario upfront and deliver early instead of making promises I can't guarantee. This failure taught me that leadership credibility comes from managing expectations, not exceeding them through luck. Our 4.6/5 customer satisfaction rating exists because clients trust our timelines, and we've never missed a promised completion date since implementing buffer periods in year two.
After years running Brisbane360, my biggest failure came during COVID when I tried to pivot too quickly into luxury private tours for wealthy locals while our bread-and-butter school and corporate clients were canceling left and right. I invested $25K in upgrading vehicles and marketing materials for high-end wine tours, convinced this was our lifeline. The wealthy demographic I targeted had completely different booking behaviors than my usual clients--they wanted last-minute flexibility and premium concierge services that my team wasn't trained for. We botched several bookings because my drivers, who were brilliant with school groups and corporate transfers, didn't know how to handle entitled customers who expected sommelier-level wine knowledge. I learned that panic-driven pivots without understanding your new customer base will burn cash and demoralize your team. Instead of chasing shiny new markets, I should have doubled down on what we did best--reliable, safe transport--and found creative ways to serve our existing client relationships during tough times. The real breakthrough came when I stopped trying to be something we weren't and started offering "COVID-safe family pod" transport for our loyal school families who still wanted day trips. Revenue didn't just recover--we built stronger relationships that carried us through the pandemic.
Running Scrubs of Evans for 16+ years, I've seen plenty of mistakes that shaped how I lead today. My biggest failure happened around year three when I decided to expand our inventory by 60% across all brands - IRG, Maevn, Healing Hands - without consulting my team. I was convinced that more variety meant more sales, so I tied up nearly $25,000 in inventory that just sat there collecting dust. The real gut punch came when my most experienced employee told me "Mark, we know our customers - they want quality over quantity, but you didn't ask us." She was right - I had gotten so focused on growth numbers that I stopped listening to the people who actually talked to our healthcare customers daily. That taught me leadership isn't about making the biggest decisions alone. Now before any major inventory or business moves, I gather input from everyone on my team first. They know our CSRA healthcare community better than spreadsheets ever will, and respecting that knowledge has kept us profitable for over a decade since.