Bootstrapping is Painful – SalezShark

In today’s robust start-up ecosystem, we are encountering more and more success stories of organizations that are on the course of scaling and becoming sustainable. Stepping into the entrepreneurial path, while some consider raising funds as the most conventional wisdom, others prefer to scale it entirely from their own pockets. They plough in their own capital, and pour every hard-earned dollar into their venture. Speaking from an insider’s perspective and a bird’s eye view as well, bootstrapping is a painful as well as dedicated route. It requires continual focus and never-ending willingness to get creative about conserving and maximizing resources. As a start-up founder of a crm software company, I had to battle the very first question which was to go bootstrapped or raise funds for my business. Going with the most likely option, my first goal was to bootstrap the company into profitability.

Having spent more than 15 years in the industry at various levels and engagements, I have led and helped establish numerous organizations by providing efficient and effective business intelligence solutions. However, nothing prepared me for the experience I gained as I traversed the uncharted terrain of entrepreneurship. The learnings were immense, diverse, and even overwhelming.

The Initial Phase

Bootstrapping is painful - Ajay Chauhan - SalezSharkThe initial phase is the most critical one, as this is when most small businesses fold – more than 50% in year one and 95% within five years. During the initial years, to keep your company running, most of your profit must be re-invested back into operations. Nurturing your Sales CRM company and watching it grow from infancy into a substantial entity is an exhilarating experience. However, since you are your own financial backer and investors, it takes a longer time to grow a company, meaning you will not be earning any money for quite a while.


Bootstrapping indeed gives you the freedom to focus on your business and its growth, with the benefit of not having to answer to anyone. Nevertheless, freedom is also associated with a greater sense of responsibility. Entrepreneurs tend to burn out, losing sight of the customers and failing to grow the team to scale the enterprise. Freedom that leads to loss of focus on key goals is definitely a red flag. As an entrepreneur, you need to be persistent, profit-oriented, working with tight operations with clear goals and a plan for growth.


By running a bootstrapped business, you might not witness the accelerated growth you expected. Being bootstrapped means every penny you spend must be carefully monitored and analysed. The truth of the matter is that you may not be able to expand as you wish – unless you have a large cash reserve. While profit is not the only viable metric for sustainable growth, your focus should be on a slow yet steady growth, which requires persistence, grit and a positive outlook, even when things seem grim.

Cash is king

When you are strapped for cash, you need to look out for resources at very low rates. This included office spaces, marketing plans or leasing equipment.  Each cost saving option provides you with a means to hold as much of your precious resource for as long as possible. Right now, especially in this economy, cash is king.

It gets lonely

Bootstrapping can be a lonely business. Working on shoestring budget, you don’t have enough cash or cachet to attract high profile talent. I know because I have spent countless hours trying to single-handledly run various operations. Admittedly, it’s hard, but it forces you to get creative and come up with solutions you would never have thought of. Moreover, the good news is that you are not alone.

 “The thing about inventing is that you have to be both stubborn and flexible, more or less simultaneously.” – Jeff Bezos

As a founder of a sales management software india, considering all the revelations and hardships I encountered on this journey, I can vouch for the fact that what matters is a great product. A customer always falls in love with a great product.

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