I’ve been with Stallion Express for over 8 years and have worked in the logistics industry and customer service. I’ve faced a lot of risks in the Canadian eCommerce shipping industry. The most important thing I’ve learned from those risks, whether successful or not, is how important it is to be flexible and to do your due diligence. One of the most memorable examples in my career involved a new AI-powered route optimization system that was supposed to improve delivery efficiency. After thorough pre-tests, the initial rollout didn’t meet our expectations—in fact, it lengthened delivery times due to unexpected software compatibility issues. Instead of re-implementing the system, we modified it. By incorporating real-time feedback and tuning the system, not only did we save the project, but we also significantly improved our operational capabilities. From this experience, I want to share with others that risk acceptance is about the opportunity to face challenges and the ability to adjust and learn from those challenges. Risks in business are unavoidable, especially in fast-paced industries such as eCommerce. The most important thing to remember about risk acceptance is to approach it flexibly and with a strong framework for assessment and response. This mindset has aided me in my career journey and is a fundamental principle I continue to champion in my strategic business operations.
The most valuable lesson I've learned from taking risks in business is the importance of calculated risk-taking. Early in my career, I was overly cautious and missed out on promising opportunities. Then I went through a phase of reckless risk-taking that led to some painful failures. Eventually, I found the sweet spot – analyzing potential risks and rewards thoroughly, then taking calculated leaps when the potential upside outweighed the downside risk. One example was expanding into a new market – it was a big investment, but our research indicated a high likelihood of success if executed well. That calculated risk paid off handsomely. My advice is this: Don't be paralyzed by fear, but don't be reckless either. Take risks, but do your homework first.
One of the hardest decisions we make as business leaders is that a strategic initiative has failed. Hope leads us to carry on trying to improve things even when we shouldn’t. And since every strategic initiative uses resources, we are often throwing good money after bad. I have made this mistake repeatedly—even as I consult to my clients about avoiding it. Last year, I was launching a new product and decided to invest in a significant marketing initiative. But this time I did something different. Along with negotiating both goals and budget, I also asked the consultants to help me design a “Quit Trigger”. This would be the indicator that the initiative had failed. I wanted these initiatives to succeed. So I wasn’t out to make the quit trigger overly onerous. The first consultant I hired was super-confident. She requested the time and budget she needed, and she suggested the date by when WITHOUT DOUBT we would achieve a certain threshold of results. The Quit Trigger was set for a date beyond that, and for a much lower outcome than she was promising. But, after the full initiative ran—with tweaking, and amending—when the date to assess came around, the results were poor. The initiative had hit the Quit Trigger criteria. I ended our contract. The second consultant was given exactly the same opportunity. He requested the duration and budget he needed, and promised a minimal threshold of results by a certain date. The quit trigger was set based on those specs. But the same thing happened. After running his entire initiative, making all of the appropriate changes as we went, the results were poor. On the agreed assessment date, then Quit Trigger dictated that it had failed. I ended his contract too. These two failed marketing efforts made me question the product. Clearly, I had more work to do. Not good news, but useful news. Business strategy is a series of experiments. And discovering that an experiment has failed frees us to try another one. But without the quit trigger I would have been persuaded to continue each marketing initiative longer, spending more time and money! While I wish they had been successful, I am relieved that I knew exactly when to end them because I had created the Quit Trigger. Don’t undertake a strategic initiative without defining what failure looks like. It is every bit as important as having goals, milestones and a budget. Do everything you can to make it succeed. But if it doesn’t, you will know when to kill it.
I've learned that it's important to pick the right people to walk alongside you. You can have all of the capital to start something amazing, but if you have not secured the right advisors, co-founders, leaders, workers, etc, you are setting yourself up for organizational chaos. You don't know what you don't know, so choose qualified individuals to help you fill in the gaps. When you choose those people, listen to them. Watching quite a few startups win and lose, this is always the correct formula.
One of the most counterintuitive risks we took was to focus on actions that didn't initially scale our business. This approach involved hands-on problem solving and personalized engagement with our customers, which seemed inefficient at first. The most valuable lesson from this experience was understanding how these non-scaleable efforts could actually accelerate growth. By directly interacting with our customers, we gained insights that allowed us to innovate and improve our product in ways we hadn't anticipated. So, my takeaway for others is to not shy away from seemingly unscalable tactics, especially in the early stages of a business since these actions can provide a deeper understanding of the market and form strong customer relationships. "Do things that don't scale" - Paul Graham
Ignore your fear. You will lose sometimes, or be ignored, or overlooked. Accept this, make friends with it, and find a way to truly just chock it up to being part of the process. As the old, simple, but 100% accurate saying goes "you win some, you loose some!" When you get your win, or your heard, or valued for what you brought to the table, it is so much more sweet because you worked for it. You envisioned it, built it, engaged others with it, and at the end....you celebrate (and move on to the next challenge)! Our biggest obstacle is not the other gal/guy, but the one looking back at us with morning breath and our hair standing on end.
The most transformative changes often require the courage to break from familiar patterns and reimagine the fundamentals of how work gets done. This has been the most valuable lesson I've learned from taking risks in my business. Our company faced a crossroads: return to the familiar in-person model or address the root causes of disconnect and fatigue. We chose the less obvious path, prioritizing how we work over where we work. This decision led to a digital-first, distributed model. The results have been incredible: Top-tier talent pool: We now hire the best people regardless of location. Enhanced productivity: Re-thinking meetings and promoting "deep work" time boosts our output. A resilient, adaptive culture: This change fostered a mindset that embraces evolution. Key Takeaway: Don't be afraid to design your own road. True strategic leaps require looking beyond obvious solutions to address the heart of the matter – in our case, the very nature of how we collaborate and get work done. It takes careful planning and a people-centric approach, but the rewards are extraordinary.
One insight I've gained from my experience at AutoLeap is the importance of continuous experimentation and iteration. In the fast-paced and ever-changing landscape of the auto repair industry, it's crucial to remain agile and adaptable in order to stay ahead of the curve. Continuous Experimentation Instead of following a strict plan or strategy, we've been successful by continuously experimenting with new ideas, features, and methods. With this method, we can rapidly test theories, get user input, and make adjustments depending on actual performance. For instance, we first focused on conventional media like print ads and direct mail when we started a new marketing campaign aimed at owners of auto repair shops. But after reviewing client comments and campaign results, we found that our target group was more receptive to digital marketing strategies. We expanded our audience reach and produced more leads for our company by changing our approach and making greater investments in digital advertising and social media outreach. This experience taught us the importance of staying agile and open-minded, and the value of continuously experimenting and iterating to find what works best.
We continually launch initiatives, campaigns and events to help integrate our clients into a larger creative context. These creative platforms we build are typically unfunded at the outset. Often the vision is greater than our resources to execute them as originally planned. They are part of our strategic decision to differentiate ourselves through proprietary creative that brands and companies can seamlessly integrate. However, this strategy means that we're constantly investing additional resources, human power and our own financial investment to stay relevant and, most importantly, to free ourselves from briefing, but to have an outlet to see how far we can go with our own ideas, unlimited by client strategies. The most valuable lesson we have learned over the past decade is that going the extra mile has earned us a reputation as doers. It's become clear that our network doesn't judge us by the success of the outcome. But we do get respect and admiration for giving it our all for so long. Realizing that there is a lot of respect for that is a real reward.
If one aspires to create the unthinkable, it’s important to keep looking for innovations and trends that can enhance customer experiences. During my tenure at McCann Health, I realised that the growth our consumer counterpart achieved due to the quicker adoption of artificial intelligence was unfathomable. This was one of the most initial insights that encouraged me to challenge the conventional practices and break the myths surrounding the digital in the life sciences industry. When I established Doceree, it was surprising to see the amount of cost and time that was being saved with just the adoption of digital communication mediums. This is when we realised how leveraging AI for predictive analytics can make HCPs outreach efficient for marketers to a whole new level. This reinforced my belief that AI’s role in augmenting engagement and improving patient outcomes is almost unimaginable.
One of the most valuable lessons I've learned as a woman in the legal field, from taking risks in my business is the power of resilience and perseverance. Whether a risk led to success or encountered challenges, the key takeaway is the importance of staying resilient in the face of adversity. As a woman navigating the legal landscape, I've encountered unique challenges and obstacles. However, I've learned that embracing risk-taking with resilience and determination can lead to valuable growth opportunities and personal development. The insight I want others to take away from this is the significance of believing in oneself, pushing boundaries, and not being deterred by setbacks or failures. Taking calculated risks and stepping out of comfort zones can lead to new opportunities, expanded horizons, and professional growth. It's also crucial to cultivate a support network of mentors, peers, and allies who can provide guidance, encouragement, and perspective during challenging times. Building resilience also involves learning from experiences, adapting strategies, and staying committed to continuous improvement. I also want others to recognize the importance of advocating for diversity, equity, and inclusion in the legal profession. Embracing diverse perspectives, promoting inclusivity, and breaking barriers can lead to a more vibrant, innovative, and equitable legal community. By embracing these principles, we can navigate challenges, overcome obstacles, and achieve meaningful progress in our professional journeys.
One of the most valuable lessons that I've learned in the past 40 years of entrepreneurship is you must take action. Entrepreneurs understand that you must have passion for what you do. So when you're passionate about a project or a business and take massive action, you can create unlimited income. In the business world, you are an investor, business owner, or employee. It's your decision...early on in life, I decided that I would be a business owner and not an employee. I wanted to control my life and future, be it good or bad. I say this because entrepreneurs must understand that all businesses have ups and downs throughout the year and they must always be ready for them. So, my advice is the go for it because, and if you fail use that as a teaching moment and continue on. You can always be an employee.
The most valuable lesson I've learned is that you are the safest investment. I've made a lot of investments to scale our companies and our most recent venture, Maison. You need to trust your intuition first and back it up with data second. You can have the best strategy in the world but if you aren't aligned with what you're building - it doesn't matter. One of the best pieces of advice I got from Richard Branson was to build companies that do good and change the world. Having that mindset allows you to make moves that are intentional and aligned.
I've found, anecdotally, that people often over-catastrophise the downsides of taking risks in business and have too great of a fear of failure. When you fail, and fail repeatedly, you realise that the failure is generally not as bad you made it out to be beforehand. If you can take clear lessons from the failure, and put in place steps to avoid that same mistake/failure happening again, then you can not only move forward with a test and learn attitude but you also become more comfortable with taking business risks over time. And for many types of businesses, you need to continue to take risks to succeed in the long run.
In 2021, our CEO decided to pull our company off of Facebook and Instagram. He cited an ethical and moral dilemma with the way these platforms knowingly perpetuated negative mental health effects leading to high suicide rates — especially in teen girls. As a noteworthy software company serving the beauty and wellness industry, these issues hit home for our business. But, these platforms are also still where our industry's communities live. We certainly lose the opportunity to connect with customers and advertise to them. However, our article about this decision is one of the highest-converting posts on the site. It is hard to measure the effect this move had on our business or where we might be otherwise. However, taking this risk has certainly helped attract the right audience to our business when they find us. https://www.mangomint.com/blog/why-were-leaving-facebook-and-instagram/
In business, the most important thing I have learned is that, with risk, innovation thrives. Every risk taken can either result in failure or success, but the act itself triggers creativity and progress. We understand the importance, as a sustainable brand, of pushing boundaries and exploring new ideas that will make a positive impact. I will share a key insight: without innovation, there cannot be risk. It is by challenging the status quo and taking risks into uncharted territory that we have chances of discovering new solutions and possibilities. Embracing risk is what makes us get out of the conventional box to find new ways of solving complex issues. I hope this reminds them that calculated risks are inherent in growth and development. It is by stepping out of comfort zones and being open to uncertainty that your potential for growth and contribution toward changing the world is unlimited. Innovation does not come without risks; however, the rewards can be truly transformational.
The single most valuable lesson I've learned from taking risks in my business is the importance of embracing failure as an opportunity for growth. Early in my fence installation venture, I decided to expand our services to include high-end, custom-designed fences. This was a significant risk because it required upfront investment in more sophisticated equipment and training for our team. Initially, the move did not pay off as expected. The market response was lukewarm, and we struggled to justify the cost. However, instead of viewing this as a failure, we used it as a learning opportunity. We analyzed customer feedback, adjusted our marketing strategies, and slowly started to see improvement in demand for our custom fences. The key takeaway from this experience is that risk is an inherent part of business growth. Not every risk will result in immediate success, but every outcome is a chance to learn. It's crucial to remain adaptable, use setbacks as learning opportunities, and continuously refine your approach based on real-world feedback. This mindset can transform potential failures into stepping stones towards success.
One of the most critical lessons I learned from taking a risk came from the initial phase of my business, Frostbeard Studio. We began as a small pottery studio, but the decision to pivot and focus specifically on creating candles for book lovers was a significant risk. This niche was uncharted territory—no direct market data ensured success in appealing specifically to avid readers through scents. The pivot paid off when, just two years after focusing our business model, Frostbeard Studio became the best-selling candle business on Etsy. This experience reinforced the value of identifying and investing in a unique niche. It wasn't just about creating a product; it was about creating a product that connected deeply with a specific audience's identity and interests. This approach allowed us to build a dedicated community and stand out in a crowded market. The lesson here for other entrepreneurs is about the power of differentiation and truly understanding your customer. It's crucial to develop a product or service that fulfills a unique need or taps into a distinctive passion of your customer base. This might require moving away from broader, seemingly safer markets and taking the leap into a less tested area. However, with thorough customer research and a genuine passion for your niche, such risks can lead to rewarding outcomes and establish your business as a go-to within your specialized market.
As a marketing agency owner, the most valuable lesson I've learned from taking the risk of pursuing larger clients outside of our comfort zone is that growth often requires discomfort. Despite facing rejections, which are an inevitable part of targeting bigger clients, the process taught us resilience and the importance of refining our pitch. Each 'no' brought us closer to a 'yes', and with every rejection, we gained insights into the needs and expectations of larger businesses, allowing us to tailor our approach more effectively. The key takeaway I want to share is that ambition should be your guide, not fear of failure. When we did land a big client, it not only boosted our revenue but also our credibility in the industry. This success had a domino effect, leading to more high-profile clients trusting in our capabilities. I want others to understand that stepping out of your comfort zone can be daunting, but it's essential for significant breakthroughs. The experience of aiming high, regardless of the outcome, is a powerful catalyst for business improvement and personal growth.
I have learned the importance of maintaining a positive perspective and attitude, irrespective of the outcome, through the prudent management of risks in my business. Having an optimistic outlook and a growth mindset assisted me in remaining focused, motivated, and resilient, regardless of the outcome of the risk. I desire for individuals to recognize the efficacy of positivism as a means of surmounting obstacles, overcoming setbacks, and ultimately attaining triumph in their pursuits.