Before Discretion Capital, I co-founded ZyraTalk - and I watched it nearly implode before we found our footing. We burned through runway chasing VC-track growth targets that, in hindsight, were never realistic for our actual metrics. The moment that sticks with me: sitting in a room realizing we had maybe 4 months left and no serious term sheets. The brutal truth nobody tells you is that the worst decisions get made in those final months when desperation sets in. We eventually sold, but I watched founders in similar spots take pennies on the dollar simply because they waited too long and negotiated from a position of zero leverage. What actually saved us - and what I now preach constantly - is making the hard cuts *early*, before the runway disappears. The companies I've seen bounce back are the ones that got to breakeven with 12-18 months of runway still left, then chose their next move. That's a negotiating position. Four months of cash is a fire sale. Running Discretion Capital now, I see this pattern repeat constantly. A founder comes to us with an offer in hand, exhausted, ready to take whatever's on the table. We recently worked with a team in that exact spot - the initial offer felt huge to them after years of struggle, but we found buyers who paid 2x that number simply because we created a real process instead of accepting desperation pricing.
I ran two startups before coming back to take over Southwest Cooling and Heating, and one of them quietly fell apart not from a dramatic crash, but from a slow bleed I kept rationalizing away. I stayed in it too long because I'd built my identity around it. What actually moved me forward wasn't a pivot strategy--it was taking a "boring" corporate job. Seven years at Bank of America's corporate office felt like a step backward at the time, but it's where I learned operational discipline and financial structure that I genuinely didn't have as a founder. When I took over our family's HVAC business, those years weren't wasted--they were the foundation. I came in seeing broken processes that everyone else had normalized, and I knew exactly how to fix them because I'd spent years inside a machine that ran correctly. The mental shift that mattered most: I stopped treating the "employee chapter" as failure and started treating it as paid education. If you're in that in-between place right now, be ruthless about what you're actually learning, not just what your title says.
My biggest failure was not an outright collapse but rather a slow-motion collapse of a product that we had spent two years creating. Our focus on making the "perfect" architecture led us to ignore how quickly the market had moved on. The moment it became clear we had run out of runway was a very heavy burden to carry, and I felt as though I had let down all of the people who trusted me with their careers. Rather than walking away from this situation, I turned the entire organization into a service-focused company based upon the same level of engineering discipline that had made our product too complicated. We no longer attempted to impose solutions but began to address immediate, and often messy, problems that other companies were experiencing. This transition required a complete resetting of my ego, as I went from being a "product founder" to a "service provider" and thus experienced a significant change in identity. What ultimately enabled me to move forward was to treat the failure as an extremely costly lesson learned. Based on research from the Harvard Business Review, "intelligent failure" contains the exact type of knowledge that must be leveraged to achieve success, which is precisely what we accomplished. By applying the lessons we learned from that failure, we created a sustainable global delivery engine that has thrived for more than two decades. Business failures are typically viewed as tragic events; however, in practice, they are generally a loud message indicating the need for change. The most critical element for success is simply needing to remain in business long enough to capitalize on the lessons learned.
I've built and lost businesses before landing where I am now with Champion Air. One that stung: I launched a venture where I had the right product but completely underestimated how much culture drives execution. The team wasn't aligned, accountability was fuzzy, and customers felt it. Revenue told the truth before I was ready to hear it. When it fell apart, I didn't immediately jump to a new venture. I spent real time asking *why* -- not operationally, but culturally. That's when I got honest with myself: I had built a business around systems, but not around people. That realization became the foundation of everything I've done since, including Champion Air, where "customer success starts with culture" isn't a tagline -- it's how we earned Lennox Partner of the Year and Circle of Excellence recognition (top 35 companies nationally). The mental shift that actually moved me forward was separating my identity from the failure. The business failed. I didn't. That sounds simple, but most founders I know can't make that distinction in the moment -- and it keeps them frozen. What I'd tell anyone mid-collapse: go build something *with* someone you trust. Running Champion Air alongside my son changed how I make decisions. Accountability to family hits different than accountability to investors. It slows down the ego-driven calls that tank companies in the first place.
When the Business Collapsed, So Did My Identity For two years I worked nonstop to create and build a seven step anti aging skincare line infused with CBD. I oversaw everything from concept to packaging and launch strategy. I was not just an employee. I was preparing to become a partner in the business. The product was scheduled to hit shelves nationwide. Two weeks before launch, the CEO and founder I had worked beside for ten years was arrested. What the world now knows as the largest female Ponzi scheme in U.S. history collapsed overnight. And so did my life. In one day I lost my six figure income, benefits, investments, and the career identity I had built for a decade. I had been serving as Senior Vice President of Special Projects. Suddenly there was no company, no launch, and no future that looked anything like what I had planned. People talk about bouncing back from failure. I did not bounce back. I was drowning. I went from an executive role back to a project manager position. I jumped industries, taking whatever opportunity would take me because I needed to survive. At the same time, COVID arrived, and I spent a long stretch feeling like I was walking through life without direction. The hardest part was the shame. I kept questioning whether I was ever as capable as I thought I was. Eventually something shifted in a small way. I started listening to podcasts from people who had gone through similar collapses. For the first time I realized what I was experiencing had a name. I was stuck. So I started writing about it. I created a blog called Let's Get Unstuck where I shared the truth about losing my identity and trying to rebuild it. What surprised me was how many people connected with those stories. Soon others began sharing their own. What started as a personal outlet has grown into a shared storytelling platform and podcast where people talk openly about moving from pain to purpose to power. The business never launched. That chapter of my life ended overnight. But losing everything forced me to build something that finally belonged to me.
A launch we were proud of flopped because we confused applause with demand. We had a polished website, a strong story and early sign-ups but almost nobody converted when it was time to pay. We spent months building before we asked the uncomfortable questions. The quiet checkout page was when everything fell apart. We bounced back by starting something smaller and testing first. We ran ten paid discovery calls and wrote down exact phrases people used. Then we built only what those phrases demanded. We also set a rule to have sales conversations every week. During the transition, we felt exposed because we could not hide behind building. Treating it like field research and not rejection, helped turn the next launch into steady growth.
Early on in my cleaning business, I made the classic mistake of trying to be the cheapest option in the market. I undercut every competitor to win clients, and it worked -- my schedule was packed within months. But I was burning through employees, cutting corners on product quality, and barely covering overhead. After about eight months I ran the numbers and realized I was actually losing money on some jobs when I factored in drive time and supplies. The turning point was losing a high-end client because they noticed we were using cheap cleaning products that left streaks on their marble countertops. They didn't just cancel -- they left a detailed review about it. That review stung more than any financial loss because I knew they were right. I raised prices by about forty percent, switched to premium eco-friendly products, and repositioned as a luxury health-conscious cleaning service. I lost roughly a third of my client base overnight. For two months I seriously questioned whether I'd made a fatal mistake. But the clients who stayed started referring people who valued quality over price. Within six months I was earning more with fewer clients, less stress, and employees who actually took pride in the work because we were using products and methods worth caring about. The failure taught me that racing to the bottom doesn't just hurt margins -- it kills the thing that makes your business worth running in the first place.
My first SaaS idea was a total flop. The hardest part was admitting nobody actually wanted it. But that failure taught me how to listen, and that's what made Bizness Apps and Acquire.com work later. The breakthrough wasn't another product. It was learning to figure out what people actually want before you spend months building it. If you have any questions, feel free to reach out to my personal email
We opened a satellite office in Dubai in 2019. One anchor client, promises of steady work, a signed lease, four new hires. Classic founder optimism. That client restructured internally three months in. Project shelved. Suddenly we were bleeding cash in a market with zero pipeline. I spent five months flying back and forth while the India operations suffered from my split attention. Revenue dipped 31% that quarter. Closed the office eight months later. Let go of people I had personally recruited. That part stays with you. What I took away was simpler than any business school framework. I had confused excitement with strategy. Dubai felt exciting. The anchor client made it feel safe. I built a plan around vibes instead of numbers. We expanded internationally again later, into 15 countries. The difference was boring and painful. Three confirmed clients before entering any market. Remote-first only. No physical offices. Expansion risk dropped roughly 80%. The question I ask before every major commitment now: what happens if the anchor disappears? That one question has saved us more money than any strategy framework.
I've built and sold five companies, but one of my earlier media ventures nearly broke me. We scaled fast, hired aggressively, and then lost our two largest clients in the same quarter. Payroll was due. The business I thought was worth $3-4M was suddenly worth nothing. What I actually did: I didn't pivot immediately. I went back to working *in* the business instead of *on* it -- producing TV shows on the road, including projects like Catfish and My Five Wives. Humbling for someone who saw himself as a "CEO." But that period forced me to rebuild from revenue, not from vision. The mental shift that changed everything was realizing the failure wasn't the business model -- it was that I had no systems, no recurring revenue, and the whole thing ran through me personally. When I lost those clients, there was nothing underneath. No foundation. Just personality holding up a house of cards. That lesson directly shaped how I run The Advisory today. When I see an HVAC or plumbing owner whose entire business runs through their cell phone, I know exactly what that fragility feels like from the inside -- because I lived it. Failure taught me what buyers now pay premiums to avoid.
We had the deck, the data, and the conviction, and almost nobody bought it. We invested heavily, believed we understood the problem, and assumed adoption would follow. Instead, sales cycles dragged and feedback conflicted. The moment it became clear was during a call with our most promising prospect. After weeks of engagement, they told us they could not justify the internal effort required to implement the product. The issue was not price or value. It was the operational lift their team would need to take on. That conversation exposed the real problem: we had overestimated urgency and underestimated the friction of adoption. After that call, I kept the team steady externally but started reassessing our assumptions internally. I went back to customers, revisited lost deals, and asked the questions we had skipped earlier. Those conversations made the pattern clear. We had built around logical value, but ignored the moment when customers were actually ready to adopt a new solution. The product made sense on paper, but the timing did not match how teams prioritized new tools. We responded by narrowing focus and cutting features that lacked confirmed demand. The roadmap was rebuilt around needs we could validate through direct customer feedback and real usage signals. That failure reshaped how we approach product decisions. Ideas still matter, but evidence now leads the process. The question we ask before building anything is simple: is the market ready to act or just ready to agree?
Before Software House, I tried launching a SaaS product for restaurant inventory management. Spent about $35,000 AUD of savings and 8 months building it with a co-founder. We thought it was brilliant -- automated stock tracking, waste prediction, supplier price comparison. The problem? We built the entire thing without talking to more than 3 restaurant owners. When we finally launched, we got 12 sign-ups in the first month. By month three, 9 had churned. The feedback was devastating but fair: restaurant managers didn't want another dashboard to check. They wanted something that worked inside the tools they already used. We'd built a standalone product for people who were already drowning in apps. The co-founder relationship also fell apart during this period. We hadn't agreed on equity splits properly, hadn't defined roles clearly, and the stress of a failing product amplified every small disagreement into a massive fight. We dissolved the partnership in month 10. What happened next: I took a contract developer job for about 6 months to rebuild my savings and my confidence. During that time, I paid close attention to what clients actually needed versus what they thought they needed. That listening skill -- which I completely lacked before the failure -- became the foundation of Software House. The thing that helped me move forward was accepting that the $35K wasn't wasted -- it was tuition. I learned that customer validation comes before product development, that co-founder agreements need to be written when everyone's still happy, and that market pull beats product push every single time. Software House exists because of that failure, not despite it.
Being the Partner at spectup, I have had a front row seat to startup successes and failures, and I've experienced a few of my own early missteps that felt much bigger at the time than they actually were. One project that stands out was an attempt to launch a boutique service connecting early-stage founders with specialized investor networks. The concept made sense on paper, but execution failed on several fronts: the market wasn't ready, our messaging didn't resonate, and we underestimated the effort required to build trust with investors who had entrenched relationships. When things fell apart, it was both humbling and disorienting. I remember staring at the spreadsheets one evening and realizing that the runway was gone, and our projections were just optimism. For a moment, the instinct was to pause, step back, and consider returning to a traditional employee role for stability. But instead, I chose to reflect on what had actually worked—our ability to structure deals, connect with founders, and think strategically about fundraising. That reflection became the foundation for spectup. I realized that rather than abandoning the entrepreneurial path, I needed to pivot the model toward what we do today: providing end-to-end capital advisory services for growth stage companies. We formalized processes, focused on traction and investor readiness, and scaled gradually instead of chasing a "big launch" prematurely. What helped me move forward was a combination of accountability and curiosity. I reached out to mentors and industry peers to debrief honestly, and I deliberately chose small wins to rebuild confidence. I also accepted that failure doesn't mean incompetence; it often signals misalignment between timing, execution, and market readiness. Over time, the lessons from that early failure became an asset: they informed how I structure deals, coach founders, and even approach risk when evaluating new opportunities. Ultimately, the experience reinforced that resilience is less about never failing and more about observing what actually works, learning, and pivoting decisively. It shifted my mindset from fearing failure to treating it as an iterative step toward building something meaningful and sustainable.
I spent 8 months convinced our content strategy was working because traffic numbers looked good. Blog visits were climbing. Social shares were steady. Then someone on my team asked a simple question. How many of these visitors actually signed up for anything? The answer was almost none. We were attracting people who wanted free advice, not people who wanted our service. I had to scrap 6 months of content and rebuild around topics that our actual paying clients asked about. The traffic dropped 40% but leads tripled. I guess the failure was confusing attention with interest. They feel the same in a dashboard but they are fundamentally different things.
My first version of ResumeYourWay failed. Not dramatically -- no big public implosion. It just quietly stopped working. I'd built the business as a generalist resume service. Anyone who needed a resume, I'd write it. Entry-level baristas, mid-career marketing managers, warehouse supervisors. I said yes to everything because I thought volume was the path to growth. And for a while, the numbers looked fine on paper. But the business was slowly dying underneath those numbers. My margins were terrible because generalist work is a race to the bottom -- there's always someone on Fiverr willing to do it cheaper. My clients didn't refer anyone because "she writes resumes" isn't memorable enough to mention at dinner. And I was burning out writing 15-hour days on projects that didn't actually require my specific expertise. The real failure wasn't financial, though. It was strategic. I'd built a business that could be replaced by anyone with a laptop and a grammar checker. I hadn't built anything defensible. What happened next wasn't a dramatic pivot. It was more like a slow, uncomfortable realization that I was wasting the one thing that actually made me different: I'd served in the military. I understood federal hiring. I knew how the GS system worked, what KSAs and ECQs actually meant, and why a brilliant military leader's resume could get auto-rejected by a government ATS. So I stopped taking generalist clients. Cold turkey. It was terrifying because I was cutting off 70% of my revenue with nothing guaranteed on the other side. For about four months, income dropped hard enough that I questioned the decision every single day. But then something shifted. The federal and military clients who found us started referring everyone they knew. Our close rate went up because we weren't competing with Fiverr anymore -- we were competing with nobody, because nobody else had our combination of military experience and certified resume expertise. We've now served over 110,000 clients with a 92% interview success rate. The lesson I keep coming back to: the first version of your business is almost never the right one. The failure wasn't that I built something wrong. The failure was that I kept running the wrong model for too long because the revenue made it feel safe.