We asked business leaders how they turned financial setbacks into opportunities. Here’s what they learned about recovering and making better decisions.
One financial mistake I made early in my first business, an e-commerce company, was underestimating both the time and money it would take to get everything off the ground. While I thought I had a solid plan, I quickly realized that only about 20% of my initial expenses were ones I had predicted. The rest came from adapting to customer needs, upgrading processes, and investing in technology I hadn’t anticipated. This isn’t because I lacked planning skills; it’s because business evolves in ways you can’t always predict.
To overcome this, I started building in buffers for both time and money. I assumed every task or project would take at least 20% longer and cost 20% more than I initially estimated. I also ran multiple models to plan for best-case, worst-case, and likely scenarios. Lastly, I “lied” to myself about deadlines and budgets, setting earlier completion dates and stricter spending limits to keep myself ahead of schedule and under budget.
My advice? Don’t get discouraged if things take longer or cost more than you anticipated—that’s part of the journey. Instead, plan for flexibility and use those unexpected challenges as opportunities to learn and grow. Remember, building a business you love is worth every hurdle along the way.
Meg Wheeler
Founder + CEO, The Equitable Money Project
I used to keep my savings tucked away in an envelope or a basic checking account, assuming it was the safest choice. I’ll admit, I even worried about the bank literally going up in flames—call me crazy! Eventually, I realized we don’t naturally get ‘money lessons’ in life, so I decided to teach myself. Once I discovered that time is money’s best friend and embraced ‘set it and forget it’ by investing in index funds and high-yield accounts, my savings started working for me. My advice is simple: start somewhere, no matter how small, and learn as you go. Don’t fool yourself into thinking you don’t have time—begin investing today and let the magic of compound interest work in your favor.
Simi Mandelbaum CFT-I, AFC, FBS
CEO and Founder, PROSPR Financial Wellness LLC
One HUGE financial mistake I made back in the 2000s when I was first in business was not tracking my money and this led to me making some poor choices and getting into a bad financial situation… It’s important to not just track what’s coming in and going out but to track and understand your sales pipeline. When you’ve got a clear idea of lag measures (what’s happened) AND lead measures (the activities that lead to the lag measures) then you can take remedial action fast if the numbers aren’t looking as good as you want. Generally speaking your accountant is only going to talk with you about the lead measures – that’s why I provide my clients with a simple tracker based on their business model and hold them accountable to it. It often requires a change in mindset to achieve this change in focus… Yet the relief business owners feel and the improvements they see in their sales and profits is worth it!
Una Doyle
Business Strategist and Coach, CreativeFlow.tv Ltd
One financial mistake I made was not building a sufficient emergency fund early in my career, which left me vulnerable when unexpected expenses hit. At one point, a major car repair wiped out my savings, and I had to rely on credit cards to cover the costs, which created unnecessary debt. The stress from that situation taught me the importance of prioritizing savings, no matter how small the contributions might seem at first.
To overcome it, I automated my savings by setting up a separate account and transferring a fixed percentage of my income each month. I also made paying off the credit card debt a top priority by cutting unnecessary expenses and focusing on high-interest balances first. My advice to others is to treat building an emergency fund like any other essential expense—start small, but stay consistent. Having that financial cushion gives you peace of mind and flexibility when life throws unexpected challenges your way.
Erik Hemingway
Founder, Nomad Capital
In my late teens, I launched a personal training studio, fueled by passion and a belief that hard work alone would guarantee success. I had checked off many of the essential boxes – securing space, acquiring equipment, and refining service offerings. But one critical oversight became a defining lesson: I underestimated the importance of having a sufficient financial allocation for business operations and marketing.
Like many first-time entrepreneurs, I believed that “if you build it, they will come.” This mindset led me to allocate most of my funds toward startup costs, leaving little for ongoing operational expenses and strategic marketing efforts. As cash flow issues mounted, it became clear that even the best products or services require visibility and a steady flow of customers to sustain growth. Without a dedicated marketing budget, I was relying too heavily on word-of-mouth, which wasn’t enough to drive consistent revenue.
The realization came with a heavy dose of humility. I shifted my focus from day-to-day survival to long-term planning. I sought mentorship from seasoned business owners and enrolled in formal business education, which provided the financial literacy I had been missing. I learned to analyze cash flow projections, allocate a set percentage of revenue toward marketing, and prioritize operational reserves. In future ventures, I built marketing and operational budgets into the financial foundation of every business plan.
Advice for Others
Looking back, that experience shaped how I approach financial planning today. It taught me that passion must be paired with financial prudence and that visibility drives viability. My advice? Don’t just plan for your launch – plan for your longevity.
Chad Harmer
Founder, CIO, Real Estate Broker, and Financial Planner, Harmer Wealth Management
My biggest financial mistake came after unexpectedly making my first million through CPA marketing. As someone who grew up with limited means, this sudden success inflated my ego, and I immediately upgraded to a luxurious lifestyle, convinced the money would keep flowing.
When my ad campaigns were halted a year later, my income dried up, but I couldn’t accept reality. Instead of adjusting my spending, I continued splurging on material possessions, desperately trying to maintain the illusion of success.
The journey to overcome this mistake was long and humbling. It took years to accept that my success had been largely circumstantial rather than skill-based. Through extensive reading on personal development and finance, I’ve learned that life is a continuous journey of growth and learning from our mistakes.
For those facing similar situations, I have two pieces of advice:
First, if you haven’t hit it big yet, invest time building solid financial knowledge, especially if you have a complicated relationship with money due to your upbringing. Books like ‘The Psychology of Money’ by Morgan Housel and ‘The Millionaire Next Door’ by Thomas J. Stanley provide invaluable insights into healthy money management.
Second, if you’ve already made financial mistakes, focus on acceptance and personal growth. Books like ‘The Slight Edge’ by Jeff Olson and ‘The Obstacle Is the Way’ by Ryan Holiday were instrumental in my recovery. I’ve found that combining personal development with daily practices like meditation and journaling (just 30 minutes each morning) has helped me maintain perspective and continue growing.
Remember, it’s okay to make mistakes – what matters is how you learn and grow from them.
Kim Koh
Internet Marketer, WolfBucks Sdn Bhd
I once delayed hiring key talent to save costs, believing we could “make do.” The result was slower product development and missed opportunities to lead in our market. That hesitation cost us momentum and, ironically, more money down the line. Delaying essential hires creates bottlenecks that are far more expensive than salaries. I learned that investing in people is an investment in growth.
We prioritized hiring strategic roles and building a strong team culture around shared goals. Bringing in the right people early on accelerated our ability to innovate and adapt. My advice to others is to see talent not as a cost but as a multiplier. The right hires repay their salaries through increased efficiency, creativity, and opportunities. Don’t let short-term savings stunt long-term growth.
Alari Aho
CEO and Founder, Toggl Inc
Early in my career, I was eager to build wealth quickly, and I let that excitement cloud my judgment. I received a “hot tip” about a high-risk investment and, without fully researching it, I dived in, thinking it was a sure thing. But the stock plummeted, and I lost a substantial amount of money. It served as an unexpected awakening. While the financial setback was challenging, the true lesson was the realization of the importance of slowing down, conducting thorough research, and avoiding impulsive decisions. Since then, I’ve adopted a much more cautious approach to investing, carefully analyzing each opportunity before making a move. If you’re in a similar situation, my advice is this: never rush. Don’t let promises of quick riches sway you; instead, take the time to research and question everything. The peace of mind you’ll achieve will make the effort worthwhile.
Matt Gehring
Chief Marketing Officer, Dutch
One of the biggest mistakes I made in my financial journey was delaying my retirement savings. Like many others, I thought I had plenty of time to save for retirement and focused on more immediate financial goals such as buying a house or paying off student loans. I postponed contributing to my 401(k).
Realizing the lost growth, I maximized contributions and took advantage of employer matching. For instance, if I had contributed $5,000 per year to my 401(k) starting at age 25, I would have accumulated over $600,000 by the time I turned 65. I would only have accumulated around $320,000 at the same rate of return by delaying my contributions until age 35. The difference of $280,000 is a significant amount that could have greatly benefited my retirement.
My advice is to start saving for retirement as early as possible, leveraging compound interest and employer benefits. These include employer matching and tax advantages of retirement accounts. Don’t wait until your 30s or 40s to start thinking about retirement savings. The earlier you start, the more time your money has to grow and provide for your future self.
Max Avery
Chief Business Development Officer, Digital Family Office
As the CEO of Kit-RH, I’ve always believed in pushing boundaries-whether through our FIT 360deg tool or innovative HR strategies. But one early financial decision remains etched in my memory as a turning point.
When launching our first major product, I underestimated the importance of cash flow visibility. Excited by the prospects of innovation, we invested heavily in product development without anticipating delays in client payments. This led to a cash flow gap that strained our ability to cover operational expenses. It wasn’t a question of profitability-our product was gaining traction-but the timing mismatch between income and expenses created unnecessary stress.
The solution lies in better cash flow forecasting and discipline. We started by adopting Trezy, a cash management tool that gave us a real-time overview of our finances. Trezy not only streamlined cash flow monitoring but also allowed us to simulate scenarios, helping us prepare for potential bottlenecks.
We also diversified our payment terms, offering discounts for early payments and introducing staggered payment plans for clients. By combining technology with strategic adjustments, we transformed a crisis into an opportunity to build financial resilience.
If I could give one piece of advice, it would be this: Cash flow is not just a financial metric; it’s the lifeblood of your business.
Invest in the right tools. Tools like Trezy make cash flow management accessible, even for small businesses. Automation and data-driven insights can save you from reactive decisions.
Don’t fear flexibility. Adapt your payment policies to match your financial rhythms. A small incentive for early payment can be a game-changer.
Plan for the unexpected. Build a cash reserve that acts as a buffer, so unexpected delays or downturns don’t derail your operations.
Mistakes are inevitable, but how you respond defines your journey. For me, that misstep was the catalyst for adopting smarter financial strategies and tools, allowing Kit-RH to thrive while staying innovative and client-focused.
By learning from your financial challenges, you’ll position your business not only to survive but to grow.
Antoine Louis
CEO, KeepInTouch
One financial mistake I made early on was overestimating the cash flow from large orders. I took on a big contract with a client, assuming that the funds would roll in quickly and we’d be able to cover expenses without any issues. However, delays in payment and unexpected operational costs led to a serious cash flow crunch.
To overcome it, I had to tighten up our financial planning and shift focus to building better relationships with smaller, more consistent clients. I also set up more robust invoicing and payment systems to ensure quicker turnover on receivables. This experience taught me the importance of never relying too heavily on one client or assuming cash flow will always be as smooth as projected.
For others facing a similar situation, my advice is simple: always have a clear, realistic cash flow plan, diversify your client base, and build a safety net for unexpected challenges. Keeping a close eye on your finances and adapting quickly will help you navigate those tricky moments.
Rick Elmore
CEO, Simply Noted
Cash is not the same as profit. I remember thinking that profit was the most important thing to focus on. Everyone wants to keep increasing profit, right? Yes, but it can take a bit of time to realize that profit is not the same as cash – and that is often when cash becomes really tight.
You can’t pay your employees with profit. If you don’t pay them on Friday they generally don’t turn up on Monday! You can’t pay suppliers with profit. If you don’t pay suppliers on time and within credit terms then typically you go on “stop” and supplies dry up thereby restricting the ability to trade effectively. It’s also easy to manipulate profit by different accounting treatments – prepaying things and using work in progress to artificially inflate profit. It might look good on paper, but it’s just fooling yourself. Remember, your bank statement is usually correct – it doesn’t lie and can’t be manipulated!
Without cash or working capital facilities, a business is unable to continue to trade even if it is showing that it is profitable. I now focus on cash and have 2 rules for any business to emphasize this.
Rule 1: Focus on cash.
Rule 2: Don’t forget Rule 1.
This underlines the importance of cash and is something I think about every day. It’s easy to get caught up in the focus on sales and growth, but ultimately you must be profitable and even more importantly you must have cash. Learn and apply this before it becomes an expensive mistake.
Craig Alexander Rattray
Growth Strategist, Know Your Numbers
