10 September 2021

From Corporate Career to Intrapreneur and Entrepreneur

by Yash Deshpande

At some point in our life we all dream of creating a start-up that we nurture from bootstrapping to its unicorn days. A classic rag to riches story that helps us escape the corporate 9 to 5 and tackle problems that impact millions of users. An article on entrepreneurship.com sheds light on 6 major reasons why people opt for entrepreneurship.

Spoiler: The major theme is the lack of influential opportunities in a corporate setting. There is no denying that some people are more suited for a corporate career whereas some folks are built for entrepreneurship. Both tracks have certain skills which are common for success and quite a few skills which differ.

Have you been tinkering with the idea of starting your entrepreneurship journey? Then let us share some tips and ideas to get started on the right track!

Let’s look at a few different things which will clear some of the pressing questions that might be running through your mind:

  1. Skills for an Entrepreneurship Tenure
  2. The Ideal Time to Jump
  3. Serious thinking About Entrepreneurship
  4. Intrapreneurship as a Litmus Test
  5. Setting Sail on the High Seas

Skills for an Entrepreneurship Tenure

A lot of corporate folks fail to make it in the start-up world. This is due to the fact that entrepreneurship needs a long-term vision with rapid iteration. Whereas in a corporate role, you are a small part of the company vision and afforded the safety of tried and tested methods. Entrepreneurship is a rocky path with a near zero record of start-ups that have hit it out of the park on the first try. So, an ability to accept and learn from failure and rejection is the bedrock of entrepreneurship.

Key skills that you need to be a successful entrepreneur include:

Strong Networking Abilities

Everything from finding your co-founder to raising funds, happens via your network. Hence, as a start-up founder, you need to build a strong network that you can rely on. Building a network is essentially give and take. So, identify what you contribute to your network.


As a founder, you will encounter countless rejections as well as have a hard time convincing your vision to investors or customers. Hence, perseverance and taking failure in your stride are absolutely vital skills.

High Risk Appetite

As a founder, you have to take multiple risks like deciding which direction should your product pivot. Should you back out of a certain market or should your start-up get into a price war? And these decisions will always be risky, and as an entrepreneur you need a strong risk appetite.

Openness to Feedback

Matthew, co-founder of Seshboard, believes an important ingredient for being a successful business builder is to be open to feedback. 

“Entrepreneurship is an extended endeavor of 360-degree feedback. Entrepreneurs need to be receptive to feedback from their target customers. This is how you learn whether your solution will solve a market pain point, or create enough ‘quantum of utility’ to change customer behavior. An entrepreneur also needs to be receptive to feedback from the employees, peers, investors and the market demands. It is tempting for many entrepreneurs to push ahead and build their solution based solely on their own ideas and beliefs. But all ideas need validation. Honest, critical and impartial feedback is what helps entrepreneurs build or pivot to solutions that the market actually needs. I’d strongly recommend ‘The Mom Test’ by Rob Fitzpatrick to anyone considering starting down the road of entrepreneurship.”

There are more skills such as communication skills, pitching abilities, technical and financial understanding. But the above four skills are essential from Day One. 

The Ideal Time to Jump

The simple answer: there is no ideal time to becoming an entrepreneur. You jump when you are ready! And if you are ready when you are 60, so be it! More corporate experience helps you see more problems within your industry and gives you more opportunities to explore them before you go solo.

To a prospective start-up founder, our advice is simple: take a smart approach to time your jump. We advise you to look at three broad buckets when you evaluate your jump:

Personal Life

Introspect your personal life and see if you have the bandwidth to jump into entrepreneurship. Did you just become a parent? Or do you and your spouse have sufficient savings to support the family as you try to build your venture? Do you need to spend on any big items like buying a house or an education for your child?

We advise you to look at time and money to understand what sort of bandwidth your personal life affords.

Professional Life

If you have significant work experience, you need to evaluate if entrepreneurship is the right choice for you. You would be giving up on a promising corporate career that might not wait for you in case you decide to come back. And if you are someone relatively young, are you fine with sacrificing a few years building something while your peers rise through corporate ranks? Also, understand what product you are trying to build, which industry will your start-up target, and if your corporate experience augments your start-up mission.


What is motivating you to become an entrepreneur? Is it a product that you believe the market needs? Or are you simply trying to escape the corporate 9 to 5? Do you believe that you can sustain the start-up life for the next 10 years or is it short-term motivation that is driving you? Would a promotion or salary hike in your current job change your mind? Are you only looking at your start-up as a way to make a lot of money? It is vital that you ask yourself these questions and introspect over your motivation.

Before you become an entrepreneur, make sure you have buy-in from your family. You also need sufficient financial savings a strong motivation to solve an issue.

Serious Thinking About Entrepreneurship

The start-up environment has really taken off in the last 10 years and investors are willing to pump money into great ideas. Many see appeal in entrepreneurship and calling oneself a ‘founder’. Hence, a lot of us have pondered quitting our cushy corporate jobs and bootstrapping a start-up that we IPO one fine day! But if you are in a corporate role and considering entrepreneurship, where does it all start? With an idea? Well, yes, with an idea but doesn’t everyone have dozens of ideas?

Reflecting on his journey from corporate CFO to the founder of Volve, a corporate credit card and expense management SaaS platform, Michael remarks:

“During my career, I’ve seen many business models and stories – I’ve seen young companies grow old, established companies transform over time. During that period, you get a lot of ideas. Really ideas are cheap though. It’s not the idea in the end. It’s all in the execution. You have a lot of people that see a business and think, “I had that idea three years back. I could have done that.” Yes, you could have, but you didn’t do it. For everything to come together, it’s not just a decision. It’s not like one morning, you will wake up and say, ‘OK, I want to run my own company.’ It is a lot of things coming together: The right timing, the right people, an idea of the market. Your own personal situation and the personal situation of your co-founders. All of these things have to come together.”

Start With a Problem Worth Solving

It is a good to start with an idea of what problem you are trying to solve as an entrepreneur. But then, you need to roll up your sleeves and start working on the execution. In a corporate job you have a financial safety net plus you get first-hand exposure to a lot of problems that customers encounter.

If you are serious about entrepreneurship while you are working a full-time job, we recommend you focus on three things:

  1. Building the framework for a solid product and getting to know the market.
  2. Finding the right set of people that you want to work with; from a co-founder to developers and freelancers.
  3. Actively getting involved in the start-up ecosystem to connect with fellow entrepreneurs and prospective investors.

Intrapreneurship as a Litmus Test

A lot of amazing companies, such as Zoom or Grab, were founded by corporate folks who saw issues with existing products. They then decided to build something better. In fact, corporate careers are a great way to figure out your entrepreneurship passions. When you work in a corporate role, you identify a lot of issues with different products. You understand underserved market segments or simply see a lot of inefficiencies in organizational processes.

Intrapreneurship is a great way to test your appetite for entrepreneurship. Intrapreneurs are corporate employees who take on a project within their organization and lead it like a start-up. It could be setting up a new business division, fixing a product, or pivoting products to capture the market. A lot of organizations are rapidly embracing intrapreneurship to integrate design thinking and replicate the fast-paced environment of a start-up. This helps organizations accelerate problem-solving as well as retain employees who are more passionate about entrepreneurship. Take the example of Zoom founder, Eric Yuan, who was a corporate employee at WebEx and then Cisco. These corporate stints paved his way to entrepreneurship as he could identify problems with existing products. He then came up with a new and better product, Zoom!

If you are serious about entrepreneurship, taking on an intrapreneurship project within your organization is a safe first step. That way, you get to replicate a start-up environment, understand how to manage people and convince stakeholders to buy in. You will realize whether you can deal with the pressure of leading a start-up; all this without leaving your corporate job.

When you are considering the scope of an intrapreneurship project, there are three things we advise you to ensure:

A Wide Range of Stakeholders

The more stakeholders you have, the more moving parts. This means you are always on your toes, constantly negotiating with different stakeholders and dealing with different personalities.

Financial Impact

When a project has a $ impact associated with it, there is also an increased risk. As a result, you need to be extra cautious about your project investment and project payback. This will replicate a bootstrapping start-up environment as well as the pressure that investors put on founders. 

A Mentor or Prospective Co-Founder

When you assemble your team, try to have someone on your project team who can be considered a mentor in your start-up journey. Or speak to a colleague who could be a prospective co-founder. This will be a great litmus test to see if you are compatible with your prospective co-founder.

When it comes to intrapreneurship projects, our advice is to be proactive and search out these projects in your organization. Don’t wait for the organization to hand them out! 

Michael is an advocate for testing your ideas in a corporate setting. He says:

“I often tell people that it’s very simple. To start, you pick one task. Maybe you just look at subscriptions and analyze the numbers, see what is still needed or not needed. Then find the people in the business to discuss your findings with. Book a meeting with them for half an hour and say, ‘this is what I have seen. I’d like to see what you think about it.’ However, be humble. You don’t know everything, right? You see the numbers, but you may not see other things that are going on in the business. Don’t go there thinking you’ll teach people that this is what you have to do. That’s not the idea. The idea is to present your analysis and see what people think about it. And then propose what you can do to improve the project and how you would go about doing it.”

Three Steps to Becoming an Intrapreneur

So, if you are keen to test out the waters of the start-up world, our advice is:

  1. Look within your organization to see if there is any project that sparks your interest. Speak to people working in that department and understand what the issue is and think of what could be a solution.
  2. Create a proposal of the problem and how you intend to solve it and in what timeline. Pitch the ideas to the management and ask for the required resources. 
  3. Once you have approval, build your team and start testing out different solutions. Throughout all this keep your management aware of the progress and take regular feedback from your team. 

This is already beginning to sound a bit like a start-up!

Setting Sail on the High Seas

So, you have decided that entrepreneurship is your calling and want to set sail on the high seas. Kudos! But what now? How do you go about navigating the treacherous waters that we call entrepreneurship?

Entrepreneurship is first and foremost a change in mindset. No longer are you governed by a set of organizational processes or have the comfort of a steady paycheck. The first part of your entrepreneurial journey is to figure out how to ensure the well-being of yourself and your family. So, onboard your partner on this journey, tally out your finances, and understand how far you can go on limited earnings. Make your partner a beacon of reasoning so that they can sound the alarm when things get out of hand.

Entrepreneurship Is a Marathon, Not a Sprint

Once you have arranged your personal life, you need to realize that being an entrepreneur is always about the long game. Michael knows this well and says:

“Entrepreneurship is all about iteration. It’s about building, breaking it down, and re-building. A lot of entrepreneurs go wrong by visualizing a product that solves all customer problems or meets all market demands. And that’s not how entrepreneurship works. When we started Volve, we weren’t looking to create a market revolution but rather evolve existing accounting workflows for better financial management. We want to help people evolve in terms of their financial transformation. We believe that this transformation is something that people are craving to give them some significant added value. Although people may want the change, one of the challenges we faced was deciding where to start. We wanted to add value by removing repetitive, tedious tasks with automated tools. We did not envision an end-product or a ring to rule them all. Instead, we thought of a fluid and dynamic product that evolves with our customer needs. And somewhere in that thought process, we also found the name for our venture, Volve!”

For all you maverick founders, we have three pieces of advice to help make your journey smoother:

Iterate and Re-Iterate

Entrepreneurship is not about perfection. It is about ideation and constant execution. It’s about building a flexible and dynamic product that you can adapt to the market. With the advent of new technologies, you need to build a product that can always stay ahead of the curve.

Join the Ecosystem

Be an active participant in the start-up ecosystem. You will always find valuable allies in the ecosystem. This could be a program such as the highly regarded IBM Hyper Protect Accelerator, which Volve has participated in. It could also be a start-up that you can partner with to grow, or founders who are dealing with the same challenges as you. Start-ups, unlike corporations, are more about community and partnerships. It’s competitive, but it’s also about growing together and leveraging each other’s strengths.

Have Fun While You Are at It

While newspapers laud the IPO’s and billion-dollar valuations of a select few start-ups, the majority don’t make it past the first few years. While that is the bleak side of entrepreneurship, we advise having fun while you are at it. The fact that you jumped into entrepreneurship already puts you way ahead of the millions of people who only dream about becoming an entrepreneur. So whether you are successful or not, your journey is something that will always stay with you. Cherish it!

If you have any more questions, Michael and Matthew are always happy to be your trusty entrepreneurship allies!

Yash Deshpande
My professional finance journey started in India with cars (Volkswagen) continuing in Singapore with short stints in leasing (Daimler), liquid soaps (P&G) and now laptops (Dell). Who says Finance can't be fun? On weekdays, I crunch numbers, grapple with BI tools and try to weave engaging stories for business leaders. On weekends, I write blogs for upcoming start-ups, engage with interesting folks over coffee, wind up with a movie and shuffle across 3 books.

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