7 Ways Every Entrepreneur Should Evaluate A New Idea

Board-Artificial-RobotAs an advisor to entrepreneurs, one of the most common requests I get is for an evaluation of a next startup idea. I try to explain that even the most innovative idea will fail if it is not a good fit for you at this time, so the question I ask them is “why you now” rather than “why this solution now?” The right person can make any idea a business success, and the wrong one will always struggle.

The reality is that I can’t judge any idea in your context, because I don’t know your passions, knowledge base, and experiences. If you show me a written business plan, I can assess it from a technical perspective, but that doesn’t tell me if you are the right person to create the business. Thus I can only recommend some context for you to make your own idea and business decisions:

  1. Play to your passions and personal interests. Pick an arena that gets your creative juices flowing, rather than one that everyone says is the next big thing. If your goals in life revolve around social change or the environment, aim in that direction for your startup, rather than maximizing revenue and profit. If you are not motivated, you won’t succeed.

    Entrepreneur Tony Hsieh, who founded Zappos, was passionate in his belief that he could “deliver happiness” to customers, before making a profit, through innovative moves like surprising 80% of customers with free overnight shipping. He succeeded well in both.

  2. Trust your background and intellectual strengths. The most successful entrepreneurs focus on solving a problem that they personally have experienced, and are convinced they fully understand. Also the same applies to dealing with the business elements, such as marketing, business operations, and finances. You may need a partner on this one.

    Bill Gates learned to appreciate the power of computers at a very young age, but was frustrated that available models were large and hard to program. He invented BASIC and Windows, snagged Steve Ballmer for marketing, and Microsoft helped change the world.

  3. Consider your access to resources for startup efforts. Take a realistic view of your ability to assemble the necessary funding, and attract the right people. Your strengths in physics and electronics may be excellent, but most of us could never attract the funding required for a new microchip process. Maybe you need to start with a smaller idea.

    Experts estimate the cost of the first next-generation chip factory to be at least $ 10 billion. Unless you have deep pockets, you probably need some strong connections and support from the people at Intel or AMD before committing your entrepreneurial life to this effort.

  4. Assess the time and effort you are willing to commit. Most startup ideas will fail, if you approach them like a hobby that you can work on occasionally and on weekends. It’s hard to win when other entrepreneurs, such as Elon Musk, are known to work hundred-hour weeks, and don’t have a family to balance. Your time is a critical limited resource.

  5. Count the depth of your relationships with key people. Most successful startups have deep relationships with experts who can mentor and support them, or provide access to critical resources and funding. There is no entitlement in this business. You need to enjoy building the new relationships you need, and nurturing the ones you have, to succeed.

  6. Check your interest in learning how to fill the gaps. No matter how experienced and knowledgeable you are, every startup is a new learning process. If you don’t enjoy learning, stick to ideas and businesses that are “cookie-cutter” versions of what you already know. Your success depends on enjoying the journey as well as the destination.

  7. Test your ability to communicate value to others. Some of the highest potential ideas and businesses require a massive educational and sales effort, which may not be your forte or interest. Very few ideas these days have such obvious value that “if we build it, they will come.” Most startups require leading a team of people, and engaging customers.

So before you make those cold calls to me, or any other constituency, for an assessment of the viability of your next great idea, my advice if for you to take a hard look at your own drivers and resources, per the items listed here. I’m convinced that there are more than enough startup ideas around, such that you can pick one to match your profile, and we all win with your success.

Marty Zwilling

*** First published on Inc.com on 07/21/2020 ***

Startup Professionals Musings

Serial Entrepreneur: Definition, Characteristics & Examples

Serial Entrepreneur

We hear the term “entrepreneur” a lot every day. But not many know what it means and even if they do, they usually confuse it with businessperson.

An entrepreneur can be defined as an individual who takes the initiative to act upon the opportunities available to them and convert them into commercially viable and successful projects and businesses. In doing so, entrepreneurs bear most, if not all, of the risks and uncertainties that arise from the venture or opportunity.

But not all entrepreneurs are the same. While most entrepreneurs usually start only one or two businesses in their lifetime, there is a category of people who are a bit different from the 580 million entrepreneurs all over the world.

Meet serial entrepreneurs.

What Is Serial Entrepreneur?

A serial entrepreneur is an individual who continuously takes initiatives to convert opportunities into multiple new businesses and ventures throughout his/her career, taking on greater than normal financial risks in order to do so.

In simple terms, a serial entrepreneur acts upon more than one opportunity and takes the responsibility to translate these ideas into commercially viable innovation, entities, or businesses while taking on more than normal risks.

What Makes An Entrepreneur A Serial Entrepreneur?

You might ask –

“How many companies should I have started to be called a serial entrepreneur?”

You do not become a serial entrepreneur by creating an X or Y number of ventures. If you’ve started more than one venture taking more than normal financial risks, you’re a serial entrepreneur. It can be one after the other or simultaneously.

Serial entrepreneurship is an individual’s mentality and drive to start new ventures, independent of whether they succeeded in the past or will succeed in the future.

While a typical entrepreneur might start a company and stick with it until the end, a serial entrepreneur does the same but does not stop at a single startup or venture. They instead look to start something else after that – sometimes selling the existing company at the first opportunity and starting a new one using the obtained capital.

How they handle the different ventures depends and varies upon the individual and their ability to handle operations of entirely different businesses at the same time. They may or may run it individually by themselves or appoint someone to take care of the businesses’ operations – the latter frees them to focus on starting a new business – but serial entrepreneurs are always on the lookout to start new startups and businesses and that is what defines them as one.

Here’s a serial entrepreneurship example to help form a better understanding of who a serial entrepreneur is.

Ash owns and runs a construction company and soon after, he uses the profits of this company to start an HVAC company that operates independently but also helps his construction company by providing heating and cooling equipment. After a few years, Ash looks to bring his idea of connecting freelancers and employers and launches an app. The app is a success and shortly afterwards, Ash sells the app company to another company. He is now looking to start a “budget-oriented” smartphone brand.

Ash had created three companies of which he still owns and runs two. But that is not what makes him a serial entrepreneur. It is the fact that Ash looks to start a new business and takes more than normal financial risks, even though he has no obligations to do so, is what makes him a good example of a serial entrepreneur.

“The drive to start something new”

This is one of the few defining characteristics that “most” serial entrepreneurs exhibit. Here are a few others.

Characteristics of Serial Entrepreneurs

Serial entrepreneurs stand out, be it personally or professionally. They love to take risks, are highly optimist, and have a long-term vision. Here are a few characteristics a serial entrepreneur possesses.

Risk Takers

Serial entrepreneurs are mega risk-takers. They face a larger risk of losing financially by starting multiple ventures. In some cases, existing projects might interfere with the new ones too.

Great Managers

Serial entrepreneurs usually avoid the risk of handling multiple ventures by setting concrete goals and having good time management. They take time to prioritize and work on the important bits first and then onto the less important ones.


Serial entrepreneurs can be seen as walking think tanks. They usually are at the bleeding edge of things, helping churn out successful ideas and projects one after the other. Serial entrepreneurs usually do not delve on the past but instead, look forward to what they can do in the coming future. They are constantly on the lookout for ways to start their new venture and ideas that might help them find the next new thing to work on.


Most serial entrepreneurs are creative multi-taskers who can juggle between many different operations, projects and goals at the same time or in short notice. Apart from that, serial entrepreneurs have good discipline to not let their multitasking affect the state of affairs negatively. They look to get their ideas off the whiteboards and onto the real world and hence are willing to do everything that is required.

Team Players

Many serial entrepreneurs work solo or in tandem with one other person. But, in general, end they all are good at bringing together and managing people (if not at the beginning, they become good leaders soon after). You cannot grow multiple businesses if you are not able to lead and manage yourself as well as a group of people. Serial entrepreneurs can effectively find, lead and assign the right roles to right people in every new venture that they create. Not doing so directly means the downfall of the company that they built.

Disinterested In Making Money

Serial entrepreneurs tend to focus more on developing newer ideas and bringing it to fruition rather than on the monetary goals. While financial success is necessary for any company, serial entrepreneurs do not make it their main goal. Instead, they are more interested in putting together a working team and make their ideas and projects come to life. Serial entrepreneurs are driven by the thrill induced by starting new businesses and making it work.

Serial Entrepreneur Example

Elon Musk – Real-life Serial Entrepreneur

Elon Musk launched his first company, Zip2 Corporation in 1995. Zip2 was to function as a city guide and was soon bought by Compaq Computer Corporation in 1999 for $ 341 million (stock and cash).

But Elon did not stop there.

With the acquired capital, Elon founded X.com – an online financial service and payments company. X.com took off quite well and went onto to become PayPal that we know today. In 2002, eBay acquired PayPal for $ 1.5 billion in stocks, which made Elon’s net worth increase to $ 1 billion since he held 11% of PayPal stocks at the time. Also, a few months earlier to the PayPal purchase, Musk had already started a new company – Space Exploration Technologies Company (SpaceX). The very next year, in 2003, Elon started Tesla Motors, which has gone to become the most valuable automobile manufacturers in the world in 2020. In 2017, Elon Musk launched The Boring Company, a company devoted to tunnelling and boring.

In short, Elon Musk has helped co-found the companies PayPal, Tesla, SpaceX and The Boring Company one after the other while also working on bringing other projects and ideas such as – Starlink the low latency satellite-based internet service and Hyperloop the fast transportation system – to life. While Elon still manages most of the companies he helped launch, he also sold a few and most importantly, he has always been starting new companies and businesses one after the other, making him a serial entrepreneur in the truest sense.


Serial entrepreneurship is the act of coming up with new ideas and launching businesses, one after the other. Serial entrepreneurship can be generally observed in small scale business environments since starting companies related to the previous one allows for vertical integration of the said companies – it helps complement their previous businesses and ventures.

Serial entrepreneurs may or may not – stick till the end or remain in charge of their startups but one thing is for sure – serial entrepreneurs are always on the lookout for new ideas and opportunities to launch a new company or startup.

Go On, Tell Us What You Think!

Did we miss something? Come on! Tell us what you think about our article in the comments section.


Sherpa Founders Series: A Look Ahead – with Domain Industry Veteran & Serial Entrepreneur Richard…

 DomainSherpa.com: Serial entrepreneur and domain name industry veteran Richard Lau has been highly visible lately as he has been discussing his latest company, Logo.com. We discuss his background in the industry and his thoughts for the future!Any domain investors interested in the future of conferencing, will benefit from today’s show!

10 Things I’ve Learned from a Chocolate Evangelist as a Social Entrepreneur

It is truly shocking that modern slavery still exists in the 21st century. In 2005, Tony’s Chocolonely was founded by journalists of the…

Entrepreneur's Handbook – Medium

“Computer vision can have a big impact on the fashion industry”: Interview with FashionTech entrepreneur Svetlana Kordumova, CEO of Pixyle.ai

In the post-corona virus era, one of the industries that is undoubtedly incorporating advanced technologies at a much faster speed than ever before is Fashion. Thanks to AI and computer vision powered tools, a new and engaging experience is being born for both retailers and consumers. One of the players in this league is Pixyle.ai, a North Macedonian startup founded in 2017, which provides AI-powered image recognition software for a better shopping experience.

Founded by Svetlana Kordumova, who combined her passion for technology and fashion with her desire to innovate and solve real problems, this startup is helping the industry reshape its look.

Svetlana is a PhD holder in Multimedia and Artificial Intelligence, a part-time university professor, and an entrepreneur. We had the pleasure to talk to her and find out more about how her startup is changing the shopping experience, her views on the current and future industry and work trends, as well as her work-life balance. 

Hi Svetlana, thank you for joining us! To start with, could you tell us your story? What got you into entrepreneurship?

What attracted me to get into entrepreneurship is most probably the energy and the dynamic that this profession brings. I’m a person that always wants to explore new things, who loves working in teams and creating new innovative products. Innovation is the reason that I did my PhD in AI at the University in Amsterdam, and my willingness to work on products that solve real problems is why I founded Pixyle.ai. 

AI has always been my passion, and now we live in an era where the AI technologies are advanced to a level where they can make smart decisions, improve our everyday life experiences, help us in our everyday work, automate many tasks we had to do repeatedly by ourselves before, and improve businesses altogether. It’s a shame to keep this technology only in scientific papers. So I set myself a big challenge to combine AI with my other passion – fashion, and build a product that will make an impact on the fashion industry.

Could you tell us what is Pixyle.ai all about?

Pixyle.ai provides AI-powered image recognition software for fashion retailers that enables them to provide a better shopping experience for their customers. With our Visual AI software, they can automate time-consuming catalogue management processes, improve efficiency and shorten their time-to-market. How do we achieve this? Pixyle.ai has developed an intelligent system that can understand fashion in images. Our AI technology can localize where in the image a fashion item appears (a dress, jeans or shoes, etc.) and in addition to that, it can also tell you the details of that fashion item (like color, pattern, length, sleeves type, neckline type etc.) We took this technology, and packed it in three solutions: Automatic Tagging (to provide better filter and product discovery); Visual Search (to search for products with any image); and, Similar Recommendations (to show visually similar items of what customers are looking for).

Pixyle.ai is a B2B SaaS company. Our visual AI technology integrates seamlessly within any e-commerce platform, and it is built on top of powerful deep learning models. 

How is computer vision transforming the fashion industry? And, what’s the role that Pixyle.ai is playing in the overall process?

Fashion is all about visuals. Even if you try to describe a dress with words, it won’t be the same as seeing a picture of it.

We humans can recognize what is in an image just with a glimpse of it. And although this might seem like an easy task, actually 60% of our brain is used to process visual signals. Now imagine a computer being able to recognize images just as we do. Computer vision is all about this, making computers understand images. And creating AI systems that can understand fashion in images, can have a big impact on the industry. For example, for many people online shopping can be frustrating. You’re just browsing and browsing, and can’t find what you’re looking for. Computer Vision AI systems can help find the products you want, in a fraction of the time that you’d normally be searching. It can bring back fun in online shopping!

The e-commerce customer experience is now completely driven with AI solutions, like online site navigation and search, targeted marketing, personalized offers, size and fit recommendation, style recommendation, analytics and many more. And here is where Pixyle.ai brings value and makes a difference. By using Computer Vision and AI, we take image pixels and we automatically generate semantic data from them, which is crucial for e-commerce stores to run successfully. Data is the new oil, and now imagine data being generated automatically with AI from images only. The insights and analytics this data can bring are useful for any fashion business to make smart decisions, improve and grow.

What trends have you seen emerging in online shopping since the crisis with the coronavirus has begun?

With the COVID-19 pandemic, the fashion industry is completely moving online and becoming digital. Even for those who were questioning whether to go online, now there is no question at all. 

How do you see AI changing your sector in the future? What new trends should we expect to see emerging?

Going completely online brings a vast number of challenges for fashion retailers in the complete value chain, from design, production, wholesale, and online sales. These challenges are also an inspiration for new innovative digital products. Clothes are now being designed with pixels, and they can only exist in the digital world. This shortens the time for sample design, and makes the design process more sustainable without any waste of materials. Now you can dress up digitally, and see how the style you choose will look on you with Augmented Reality. The wholesale process is moving completely digital, with digital showrooms on screens. 

Apart from being a founder and CEO of Pixyle.ai, you are a part-time university assistant professor and have a family. What’s your secret sauce for maintaining a life-work balance? What advice would you give to other founders?

My advice would be not to put any limits to yourself, and just go for what you want to do, but very importantly, to make a realistic plan and set the right expectations. See what you can do, what you will need help in, and plan things together with your team and personally with your family. Support is very important, and I could not have done anything without the people around me. There will be many bumps in the road, and asking for help is ok, and it’s very much needed. 

Life is a constant compromise between all that’s on our to-do list, and what works best for me – a continuous prioritization of those to-dos. There is always something that can wait, and something that needs to be done first.

With many startups going fully remote right now, ‘remote work’ is believed to be the future of work. What’s your current practice and do you plan to stay remote after the pandemic?

I must say that I am very happy with how the complete team of Pixyle.ai adapted to working remotely. We were up and running from day 2. We have daily meetings, and team members are working together on online calls throughout the whole day. I’m happy to see that the team spirit and the closeness we had in the office is still there, only online.

I believe once things are more settled, moving to the office or working remotely will be a decision that we will make together as a team. We’ll see what everyone’s preference is, and if they feel more comfortable staying home they can, if they want to come to the office that is also fine, or it can be a mix from the two. The practice showed that working from home is also as effective as being physically present in the office, so it’s definitely an option. What we will for sure come back to the office is for our Friday after work drinks. We all miss being with each other and hanging out.

What is it like to start a startup in North Macedonia? Would you recommend the country to foreign founders and why?

Having a startup in North Macedonia I would say is as challenging as in any other place. It requires a lot of work, adjustments, listening to your market, choosing the right accelerator for your business, forming the right team, finding the best advisors, pivoting in a pandemic, runway, investments, and many other things. And with everything being online these days, I would say it doesn’t even matter where you are. What is very important, is to choose the right startup accelerator for your industry and target market, taking the location into account then, because connections for your target market are very important.

From my experience, I am very happy with the team, there are a lot of smart and bright people in North Macedonia, the culture is very positive, people are open, and we have a very nice working atmosphere. The startup community and support in North Macedonia is also growing, and people are sharing experiences, so I would definitely recommend North Macedonia as a good place for startups.