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."
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.
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.
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.
I'm the co-founder of Mercha.com.au and have been through the startup grinder for over two years now, so I've made plenty of mistakes worth sharing. My biggest failure happened early in our MVP phase with a head of marketing from a Melbourne construction company. We promised to call her after she ordered but never did, her order took longer than expected, and we went completely radio silent during the delay. She came back and tore us apart--rightfully so--for failing on basic communication promises. That failure taught me that leadership isn't about having the fanciest tech or perfect processes. It's about doing what you say you'll do, especially the simple stuff. We were so focused on building our "high-tech, high-touch" platform that we forgot the high-touch part entirely. The lesson completely changed how I approach customer relationships and team accountability. Now every first-time customer gets a personal call, and we've built communication checkpoints into every order process. That angry customer is still with us today because we owned the mistake, sent her flowers, and both my co-founder Sam and I personally called to make it right.
I made a mistake during the initial pitch to a highly considered potential client. I was overly confident in our prior successes and thought our previous portfolio would sell our services on its own. Because of this confidence level, I didn't dedicate enough time to preparing a pitch that addressed the specific challenges and needs of this client. When the pitch day arrived, I was somewhat surprised by their inquiries and concerns, and I struggled to address their expectations. Together, we made the conscious decision to move in another direction, and as a result, our team and my company suffered a setback in terms of self-fulfillment and professionalism. This moment proved to me the importance of preparation and customization in leadership. I realized, after the fact, that every client is different and brings unique insights to every interaction. Therefore, a special presentation is important to demonstrate our understanding of their individuality. The thought of losing a client is one we learn from, and I took the necessary steps to refine our process for client pitches. I learned more about the client before the pitch day, conducted stakeholder analyses, and developed client-facing presentations that directly addressed pain points. It became apparent that each of these measures not only yielded more winning professionals but also built a stronger and more cohesive team. It reinforced my understanding that effective leadership involves not only confidence in one's abilities but also a commitment to diligence and adaptability in every situation.
I once took on three simultaneous rehab projects thinking I could juggle them all while still working my day job as a Trust Officer--I was dead wrong. I ended up missing contractor meetings, making hasty material decisions, and one property sat half-finished for months because I was spread so thin. That taught me that leadership isn't about proving you can do everything; it's about being honest with yourself and your team about capacity limits and making strategic choices that set everyone up for success.
When Cafely was just starting out, I focused on hiring for potential and eventually hired for experience and leadership. Despite their lack of experience, they learned the workflow pretty easily. I didn't expect the more recent hires to treat their colleagues poorly though. One of them was assigned to lead the marketing team. And instead of giving constructive feedback, she only pointed out their mistakes, which weakened the team's dynamics and morale; even forcing one of them to file their resignation. That's when I realized I failed to foster a safe workplace environment. Working remotely made this more difficult, so one lesson this taught me was to be more hands-on with my team. Instead of limiting our communication through daily and weekly reports, I now do my best to meet them through quick huddles on Slack, just to casually go about their day and make them feel more valued at the same time.
Early in my career, I was helping a family through a difficult probate sale and focused solely on providing a fast, efficient closing, thinking that was the best way to help. The family felt rushed and unheard, and it nearly collapsed the deal. That experience taught me the most valuable leadership lesson: our service isn't about speed, it's about support, and true leadership means slowing down to meet people where they are emotionally, not just financially.
At the early stages of the Bay Area Board Up Team, I hired rapidly to a time when we were particularly busy — focusing on speed of hiring over the alignment of a new employee to the team culture. The hire didn't fit in with the team and made a complete mess of an important project, resulting in us losing money and our image. I learned that leadership is not about plugging holes fast, it's not even about building capacity fast; As Jeff Bezos put it building a structure and culture that is resilient to the inevitable bumps that will come along. That lesson made me appreciate taking my time, even when there is urgency. Now I hire intentionally, train thoughtfully and create time for authentic communication. In a crisis-based business like ours, healthy leadership is not just nice to have, it is the thing that holds everything up.
When we first started Madison County House Buyers, I assumed that because we offered a fair cash price, that was enough to close every deal. I focused purely on the numbers, often overlooking the emotional component of why someone might be selling their home. I quickly learned that true leadership involves understanding the human element behind every transaction; it's not just about crunching numbers, but about empathy, building trust, and truly understanding a seller's unique circumstances, which has led to many more successful and fulfilling deals.
After more than a decade in the Army, I tried to run my first few property renovations with a rigid, top-down command style, issuing orders instead of collaborating. It didn't work; morale was low, and mistakes were made because my team on the ground felt they couldn't speak up. It taught me that real leadership isn't about having rank--it's about building trust and empowering the experts you hired to make decisions, which creates a more resilient and effective team.
I selected a developer because he offered low prices and immediate availability. The project team failed to meet their deadline for client launch within the first month of work. I spent most of the night in Budapest's hotel lobby working on the code because the Wi-Fi connection was poor. The experience cost me my rest and my faith in him and threatened to lose the client. The most important thing I learned was that true leadership requires maintaining high standards even when you lack energy or face time constraints. The cost of hiring someone at a low rate becomes extremely high when you operate as a business leader.
My passion for design backfired on an early Airbnb project where I installed a gorgeous but impractical kitchen, leading to complaints from golf-week guests who couldn't even wash a pot. It was a crucial reminder that leadership isn't about creating what I think is excellent; it's about listening to your customers and building an experience that serves their real-world needs first.
One failure I experienced pretty early on was burnout due to a lack of a healthy work-life balance. I wouldn't necessarily call burnout a failure (so many people experience it and it can't always be easily avoided), but my failure was with not achieving a healthy work-life balance. I didn't prioritize it nearly enough, and I definitely naively thought it wouldn't be an issue. But, I learned the hard way that I needed to prioritize it for my own wellbeing. The better the balance, the better I performed as a leader.
My biggest error occurred when I attempted to handle everything personally during our initial construction period. I arrived at the construction site with tools such as paintbrushes and power drills because I wanted to demonstrate my resourcefulness. My physical presence at the site actually hindered the work progress. The contractor took me aside to explain that he understood my dedication but my physical presence obstructed his work. The experience taught me to trust the professionals you bring into your organization. My role required me to define the company direction while making quick choices and providing support to our team members. The project timeline remained intact after I removed myself from direct involvement and the construction work proceeded efficiently.
I experienced a time of pretty significant burnout early on in my entrepreneurial journey. I was simply overworking myself without realizing that my mind and body could only put up with that for so long. I ended up having to take some time off, with my team picking up my slack during that time. Though that time off was necessary, I definitely felt like I was failing. That experience taught me the importance of managing my workload effectively. Not only would I be affected if I didn't, but my team would be too.