22 Things I Wish I Had Known Before Starting a Business at 22 Years Old

Over the last 6 years of running Cancha, I’ve been taking notes each year on key lessons I have learned along the way, and, during a tennis getaway in Barcelona over Easter, I finally found time to put them all together with you. So here’s my take on some key things they don’t teach you in an MBA program - I learned these the hard way.

1. Don’t make assumptions. It is so easy to assume that someone doesn’t have the time, money or contacts to help you, or that they simply wouldn’t be interested in what you have to offer. I've made this mistake many times over the past few years, and most recently, one of our investors and a key mentor reminded me of it.
   
   Reflecting on this, the few times when I have managed to pull back my ego and ask for help, it has opened up possibilities that have changed the course of my business and personal growth in ways I couldn't have imagined. It's humbling to realize that people are often more willing to assist than we give them credit for. Not only that, we usually have little idea of their situation or intrinsic goals, and making assumptions that they are too busy, too successful or too indifferent to help or get involved does both you and them a disservice.

   
   

2. Growth is not linear. The podcasts we listen to, the articles we read and the posts that appear in our newsfeed daily leave us to believe that everyone is moving in a consistent line, cruising in one direction towards their goal. At any given moment, we grapple with various obstacles—personal, professional, and external factors beyond our control—that hinder our progress. Building a business, or anything for that matter, depends on acknowledging this fact and having the determination to consistently push through despite the setbacks.
   
   Embracing the non-linear nature of growth allows us to approach challenges with resilience and adaptability, understanding that progress often involves navigating detours and unexpected twists along the way, moving backwards to then move forwards. It's not about maintaining a flawless trajectory but rather about learning, adjusting, and persevering in pursuit of our aspirations and goals.
   
   

3. A good business is never a one-person team. I have never met a single business that is making strides with one person and one person only. For a long time I thought I was running a solo, single founder business with no full-time employees.  However, I soon realized that I had a network of people around me. From my countless phone calls with my dad, asking him for advice, to investors, to various contractors and contacts who have been an integral part of our team.
   
   I am aware now that there exists a collective vision for Cancha, and I am very grateful for the people who have joined me on this journey in pursuit of our mission to make sports travel a seamless experience.
   
   

4. Product market fit is a journey, not a destination. People love to talk about how important product is, and how some businesses either have product fit or don’t. I have yet to find a business that has a perfect product market fit, there are always people out there who would prefer one feature over another, or don’t align with some other aspect of the brand, service or values.
   
   Product market fit is generally considered a binary concept, whereas I view it as more of a spectrum. The chances of being able to launch your product into the world and have an extremely good product-market fit from the get-go are minimal. Each year so far with Cancha, we’ve been painstakingly refining our products to better meet our customers needs, but only because we were able to put something pretty basic out there in the first place.
   
   

5. Doing things outside the business can be your biggest lever. My business is in e-commerce, but if I spent all of my time reading only about e-commerce, d2c and retail, I would end up with the same viewpoint as every other marketer or eCom business owner out there.
   
   While it is important to stay up to date with advances and practices in your industry, the biggest source of headway and margin in your endeavours is by bringing outside theories in. A typical example of this is Steve Jobs’ famous obsession with studying calligraphy, which boosted his creativity muscle and gave him a whole new perspective on apple design.

   
   However, more broadly than that, I have begun to take action to learn about the wider world outside my bubble of tennis, eCommerce and even. Having just a fractionally better understanding of history, culture, science, other languages and so much more has allowed me to very gradually begin to see things from perspectives that could not have contemplated previously.
   
   

6. Always seek advice, but don’t cling to it. Asking for advice from others who have undergone similar experiences to your situation is an excellent way to think of things differently and get out of your own head. However, seeking advice does not necessarily mean changing your mind. In fact, I have learned that taking advice is most beneficial when you do so objectively, without planning to do exactly what others tell you or sticking to your original premise.
   
   

7. Don’t mitigate or manage your risk, leverage it. Risks are an inherent part of any business - I believe that it is not simply a case of managing them or mitigating them, the key is actually to use them to your advantage.
   
   It’s all about timing: you wouldn’t run a marathon every day  (well, most people wouldn’t), but completing a marathon is a huge achievement and a significant milestone in anyone’s journey. The same goes for business - risks are your growth opportunities and should be treated as such. However, using them at the right time and in the right way within an ever-changing context is where true skill lies. However, doing so requires starting with the right mindset so you can understand and use risk to your advantage.
   
   

8. Find someone you can always talk to. I’ve had some dark times, some of those quite recently; times when it feels like everything is against you and you have an ever-mounting pressure to carry. Throughout the years, my Dad has listened to it all, and been the greatest life coach and mentor I could dream of having throughout this process. The most important thing he gives me is perspective - on life, relationships, decision making and so much more.
   
   While I don’t always come off the phone with him feeling that the problem is solved, I do feel like I have someone in my corner rooting for me, as well as a better grasp on how to attack it. This is the kind of support a good friend, family member, or mentor can offer, and when you're trying to introduce something new into the world, they are the most valuable asset you could hope for.
   
   

9. Broaden your sights. if you are in eCommerce don’t just read about eCommerce, if you’re in SaaS don’t just listen to Saas podcasts. Most of the leverage in business comes from bringing perspectives outside your industry into your domain and disrupting from there. Having an outlook and point of view different from everyone else helps you see things others are missing, and the best way to do that is to read and discover more broadly.
   
   

10. Try not to see yourself differently from others. It's common to mistakenly believe that the challenges you're facing in your project are more significant or more complicated than those encountered by others. This belief is far from the truth. Furthermore, isolating yourself in this manner doesn't help anyone; on the contrary, it makes it more difficult to detach from your problems when you most need to, and it makes it harder for others to aid you.
    
    

11. There is no substitute for making mistakes. It’s also very easy to look back at the past and think ‘If only I had known’ — but  I am what I am today because of all of the mistakes I have made. That doesn’t mean the company wouldn’t be 5 times the size if I had made different decisions, but you should never let that affect your thought process now. I wish I could have learned faster, known sooner, and had a bit more luck in the process, but such is life. The important thing is to be consistent, iterate and focus on those things that you control going forward.
    
    

12. Everything is fine until it isn’t. We think things tend to spiral gradually downward or upward in business, but in my experience, that’s rarely the case. Everything seems positive one minute, and then suddenly you are dealing with a thousand problems at once and the whole world seems against you. It’s not luck (or lack thereof), it’s that those problems were brewing for a while, you just couldn’t see them above the surface yet. The good news is, that things can often turn around just as fast, so don’t give up too early when your back is against the wall.
    
    

13. Empathy is a profoundly underrated skill in business. I firmly believe that there are many, many people out there who want to help you, you just need to give them a reason to. If you aspire to foster a business context where both empathy and competition coexist, you'll find more people willing to support you when you need it most.
    
    Why? Because you've truly understood their viewpoint and needs - not by persuading them to join your cause, but by aligning yourself with theirs.
    
    

14. Present reality should always take residence over pre-defined goals.  Goal setting has its place, but too often I have found myself and other fellow entrepreneurs in a trapped position where we feel we need to continue down a certain path just to reach goals that were several months or years prior when the situation was very different. Decision-making should be a case of focusing on what you think and not holding yourself to what you used to think. That also means learning from mistakes but not holding yourself to them.
    
    One of the worst things you can do is be afraid to make decisions because they didn’t serve you well in the past. Sometimes, doing the same thing in different circumstances is actually the best thing to do, so you should always focus more on the present context you are in versus the situation you found yourself in previously.
    
    

15. Scale comes from focusing on what matters most from a business perspective. Don’t get caught doing just the things you like, sometimes you need to do the things that really move the needle. To achieve sustained growth, it is essential to prioritize the critical aspects that can make a significant impact. While it's crucial to enjoy what you do, as well as understand what you are good at, it's also essential to focus on the tasks that can genuinely move the needle and make a tangible difference. Without a clear focus on what matters most, it's easy to get sidetracked and waste valuable time and resources on less important activities.
    
    In the early stages of Cancha’s development, I spent too much time trying to make our website look that little bit more perfect and original. I focused too much on what tools we should use, instead of what inputs and assets we could create to build true sustainable value for the business. When I realised that the biggest lever for the business was actually building reach and traffic, we started to see our numbers rise faster. It also allowed me to realise that there were other people out there better at creating scalable content than me, and I needed to bring them into the business as soon as possible to take ownership of this important level.
    
    

16. Don’t fall for ‘build it and they will come’. This was a big mistake I made and I find myself revisiting this regularly as we look to grow. Be transparent about what you are trying to do, give free value and build an audience first, before during and after your product is emerging.

    
    Build a waitlist of niche customers who geek about what you geek about - it’s always easier to broaden out later when your product or service hits the market and you continue to iterate on it.
    
    

17. Keep inventory to a minimum, especially at the beginning or when launching something completely new. This is a very typical mistake in retail and especially e-commerce, and one that I made several times over during the first two years at Cancha.
    
    I over-ordered inventory, and we launched too many color variants of the same product before we had the audience to support such a wide SKU range. I was afraid that we would run out, so I made more bags than we needed on paper at the time, only to upgrade that bag 6 months later and be stuck with the old stock that was suddenly that much harder to shift. I wish I had done things the other way around, as it would have saved me a lot of stress and anguish.
    
    For those looking to get into the physical product game: (1) make as few units as you can to begin with, (2) gauge demand, (3) iterate with user feedback quickly and (4) make sure that demand for your product is always ahead of supply. It’s much easier to deal with being out of stock and having to let people backorder, pre-order, or join a waitlist than it is to have to shift stock when you haven’t got the audience nor the the marketing power to support.
     
    

18. Don’t underestimate word of mouth. One out of five of our orders on average is a referral from another customer, and referred customers tend to be the most valuable because they have had an authentic avenue to the business. This affects how they view our products, the feedback they give and how they talk about us.
    
    However, I discovered that creating a referral flywheel is not just about offering programs or incentives. While they can help move the needle slightly, the real key to strong and consistent word-of-mouth growth is to treat every customer like a star. That's why I personally respond to ALL customer service inquiries. Maybe one day, someone else will join the team to take on this role, but only when I can be 100% confident that they will put customer needs and feedback first in every interaction.
    
    

19. Let others help you. It's important to remember that accepting help from others is a vital part of life. Reciprocity is a powerful resource that can help you overcome problems and ultimately grow. It’s all based on the idea that accepting help is a vital part of life, as long as you maintain the importance that it also works the other way around.
    
    Giving back to others whenever possible, regardless of whether they helped you in the past is also what creates this beautiful system of collective growth. This reciprocity forms the foundation of a beautiful system where everyone contributes to the growth of others, fostering a culture of collective prosperity.  
    
    

20. Communication is the #1 cause of strain. In business, there exists a delicate balance between too much and too little communication. It can be compared to the political spectrum where the far left and far right are considered extreme and unreasonable. However, when communication is maintained at an optimal level, somewhere in the middle, it allows everyone to feel valued. This analogy highlights the importance of achieving a balance between communication and autonomy.
    

    In an organization, communication is necessary but over-communicating every detail can be counterproductive as it consumes too much time and effort. On the other hand, a lack of communication can lead to a misalignment of vision, and strategy, and ultimately, an uneven distribution of workload among team members.

    I have realized that creating systems that allow people more autonomy while assigning fundamental responsibility and ownership of key metrics can be a great source of growth and leverage for the business. More importantly, it allows employees to feel valued, autonomous, and clear about their role in the company's vision.
    
    

21. Find an activity outside the business that you love doing, and consistently incorporate it into your daily routine. Anyone who knows me also knows that I am a passionate tennis player, and I am generally committed to keeping myself fit through regular gym workouts and runs. I find it challenging to spend a day without doing some form of exercise as it affects my concentration, causes me stress and reduces my clarity of thought.
    
    So, regardless of the day and the challenges that lie ahead, I am either on the court, in the gym or running before I start work or at some point later in the day. Sometimes, it means waking up earlier or finishing work later in the evening. But this is my idea of recharging, and some of my best ideas and problem-solving moments have come while exercising. I believe health is essential, but I do not mean exercise is the only way to achieve it. However, you should find something you love doing outside the business and religiously make time for it.
    
    

22. Be clear about what type of business you want to build. Are you aiming for a smaller, profit-driven venture, fostering close-knit relationships with a small team, and opting for gradual yet sustainable growth? Or perhaps you envision a larger-scale endeavour, embracing higher risks and involving numerous stakeholders, resulting in rapid expansion that may even surpass your own tenure in the business?
    
    Personally, I still grapple with this question even after years, but being aware of the differences between these types of visions empowers you to make clearer decisions along your journey, paving the way towards crafting the lifestyle you aspire to while effectively managing expectations for all involved parties.

    
    So there you have it — 22 lessons learned after starting a business at 22!
    

    If you enjoyed this, then follow along with our progress at Cancha (my brand), connect with me on LinkedIn (more business insights). 

    
    Until next time!

    Jack Oswald