10 Invaluable Lessons Learned From Working With 200-Plus Startups

Throughout my career running Awesome, I’ve executed over 500 projects for 200-plus startups, from launching napkin ideas into tangible products, executing their business plans, and working with so many different types of entrepreneurs from all kinds of backgrounds.

I’ve worked with notable brands like Udemy, Happify, Eight Sleep, Hedgeable, Thought Catalog, Kisi, Skift, ArtBinder, and Wanderfly, which TripAdvisor acquired. Not to mention Beyoncé’s first startup investment, Sidestep.

Here are 10 of the most important lessons I’ve gained in the process:

1. Developing Your Founder Passion is the Most Important Asset

If you are starting a company, one of the main things you need to do is to develop those skills that require you to run a successful business. You have to learn what it takes to develop a passion and how you can grow it over time. The study shows that ‘‘founders are displaying high passion increase neural investor engagement by 39% and investor interest in the venture by 26% over those displaying low passion.’’

I often see startup clients of mine have a great idea but are not devoted enough to their projects. Giving important tasks to inexperienced team members or assuming things will work out because they have a ‘‘great idea’’. Being driven means you will live and sleep with that responsibility, and you would spend more time on it until you succeed.

Figure out a process to quickly understand your passion. I have engaged with over 10+ various side hustles and gigs in my early 20s before settling into the entrepreneurial world. From each of these gigs, I’ve extracted different values —applying to my founder’s passion. That is OK to do many other things and learn about what’s your strengths and weaknesses.

In the end, people will invest in your product or ideas if they find you passionate about them. Having a brilliant idea is one thing but showing dedication is another thing.

2. Always Finish What You Start

One of the main lessons I’ve learned while starting my own company is that going through many different experiences all the way through will give you invaluable lessons that you can apply towards your venture. Especially nowadays, the attention span is very low; we tend to start on projects that we let go of too often. This is a downward spiral that would do nothing but harm your motivation to find the right ideas for your real passion. Pretty much, it would num you without you realizing it.

To discover your entrepreneurial spirit and founder passion, you need to gain the right experience. Hence, finishing what you’ve started is one of the main habits that will teach you what it means to go all the way through an entire process of a given task or assignment. Thus, learning all the ups and downs, even some are failures, is crucial for building your skills. Entrepreneurs with no failure are less likely to succeed in business than the ones getting their hands dirty and going all the way through the experiences they are exposed to from start to finish. This could be a personal project, a marketing campaign, or even a task given by a family member. Having too many incomplete endeavors will harm and cannibalize your future.

3. Lack of Empathy is Damaging

I often see startup founders with great intelligence, sharp cookie, and well-rounded individuals with almost having knowledge on every topic. Not to mentioned, they have traveled around the world, putting their foot on almost every continent. But one thing that is missing from this picture is that they are not as good at capturing certain emotions when it comes to managing people they are engaging with. So far, they may have convinced their investors but what is lacking is days come after raising funds. The biggest challenge for founders in the early days of their ventures is hiring the right people and managing them and not just their product.

This is an important aspect for Founders because if you lack empathy, you will not understand your users, your team, your investor’s expectations, and anything else in between. It’s an important trait that must be gained along the way.

I’ve learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.

Maya Angelou

4. Your Environment Has a Direct Impact on Your Success

I highly believe that your success comes from how you form your surroundings. I’ve learned firsthand that establishing the proper location where you render your work directly impacts your success. Many people underestimate the physical surroundings of their well-being while building their dreams. Throughout the years, I’ve experienced that where you work, where you take your meetings, your calls, who you pick to hang out with directly impact the outcome of your failure or success. Your environment is essential. Humans adapt to their environment, and hence if it is not good enough to uplift you, you may be struggling and skidding around for years trying to accomplish your dreams.

The good news is that modifying your environment is under your control. Deleteclty picking these choices is going to lead you to successful days, weeks, and years to come. It has a domino effect.


5. ‘‘Perfectionism Is an Entrepreneur’s Worst Enemy’’

I’m a firm believer that it’s unnecessary to have a perfect idea to start your startup journey. You could just start with something basic and develop it over time. The pressure to have a ‘’perfect’’ idea can lead to wrong decisions that could not be reversed easily if you’ve invested in it too much already. Not that there is anything wrong with that experience, which could teach a lot of valuable lessons. However, it’s important to be prepared as much as possible to eliminate some major mistakes in finding the right idea for your venture.

6. Seize the Energy

When the first iPhone was sold on June 29, 2007, on 5th Ave, I was there in person to witness it. Being in the right place right time is essential, but you need to sense the timing and location with a lot of dedication. If I never experience the first iPhone being sold in history and followed closely with the creation of the Apple app store, I would have never come up with an idea for UI/UX agency focusing on these technological developments. I seized the moment and it gave me the idea for my business. I’ve seen the opportunity of big industry on the horizon by following it closely and trying to understand what would be the next big thing.

Never underestimate the power of being under the radar and looking for the right time to start your business. I call this approach ABC – Always Be Chasing!

7. Keep Your Enemies Close, but Your Competition Even Closer

There is a lot you can learn from other companies who have done it before you. You don’t have to reinvent the wheel; you can simply learn from their success and mistakes. It’s important to do dedicated research on the competitive landscape of your industry. You should create a document on who are the founders of your space, what kind of employees they hire, what type of clients they go after, what’s their marketing strategy. Follow them on Google Alerts, so if a news article drops about them, you will be notified immediately. Every move they make, you should be aware of. This will motivate you to wake up early in the morning to move your startup forward.

8. Be a Full-Time Entrepreneur

If one thing that is clear that is you can’t develop your entrepreneurial passion without dedicating your full-time to it. Sure, there is a lot you can learn in corporate life, and sure we all need the paycheck. But you can’t build someone else’s dream forever. You need to quit your job and you must do it now; Because no one becomes successful by luck. Every successful founder out here has built it by dedicating their time to their dreams by being full-time.

When I started Awesome a decade ago, we had a counter on our website and would post our clients leaving their day jobs. ‘‘17 clients have quit their day job.’’ We were celebrating these statistics because it was important to encourage the industry.

9. Executing Your First Product is More Difficult Than you Think

One of the main lessons I’ve learned from working with 200+ startups is that how you launch your first product from inception to reality takes a lot more than just assembling a rockstar team of product managers, designers, or developers.

There is a fine line between must-have features and nice haves. In reality, focusing on too many features early on can kill your startup. It’s important to understand that ideas don’t necessarily translate into a good product.

Your goal should be to lower the cognitive load on your users and not increase it. The more features you include, the more they’re are going to get confused. My favorite MVP startup idea was called Push for Pizza. With just one simple interface, users can push an icon to order a pizza from the closest pizzeria. This product created a big buzz and they only had one feature! Success is not measured by the number of features, it’s about how you execute and market them.

10. It’s All About the Process

Having a proper process for launching products is the crucial difference between successful entrepreneurs and others. Every founder I’ve worked with has their own method of executing their ideas. Being organized and putting your ideas and features into a process could lead you to get rid of those bad ideas before they fail you. Part of my own process is to visualize those steps into micro-actions where I can quickly iterate them so everything is more simplified rather than being complex.

If you are launching a new product, instead of just jumping to design and research, you could create a document explaining the features, user flows and defining their priorities. And then sharing that with stakeholders to get feedback, iterate. Next would be taking those documents into wireframes, then branding, then and UI. What’s your process? For further reading, you can check our Can Distributed Teams Improve Your Startups Scalability article from the link.