For Entrepreneurs, One Really Can Be the Loneliest Number

For many budding entrepreneurs, bootstrapping can be a great (if not the only) option for getting started. Bootstrapping helps entrepreneurs retain full control, promotes financial accountability and encourages honest and scrappy solutions to the many business problems that arise.

The benefits of bootstrapping, however, may not always outweigh the struggles. Beyond the long days and limited financial resources, bootstrapping is mentally, emotionally and physically taxing -- especially when going about it alone.

The reality is that startups can be alienating, harshly visceral -- and downright depressing. In fact, a study conducted by Dr. Michael Freeman, Clinical Professor at UCSF, found that of 240 entrepreneurs surveyed, 49 percent admitted to having a mental health condition as a result of their entrepreneurial pursuits, with depression being the number-one reported condition.

It turns out that one really is the loneliest number.

One entrepreneur who knows well the challenges of starting a company alone is Chris Taylor, founder and CEO of Square Root, a software as a service (SaaS) company that leverages data science and development to build enterprise-class technology solutions. When starting Square Root in 2006, Taylor was on his own and often found his efforts devolving into a mental circus act -- with him as the head circus master. Keeping his head above water proved to be the first and most important challenge he had to tackle.

To better navigate the startup chaos and avoid personal and professional burnout, Taylor suggests entrepreneurs follow this bootstrapping mantra.

1. Get started with the three F’s of entrepreneurship.

Founding: Entrepreneurs often get far too caught up in finding the right time to start a business. The truth is that there will never be a "perfect" time, so instead of getting caught up in the endless cycle of procrastination and planning, just get started.
Frugality: When a business is bootstrapping, spending money wisely should be the top priority. It is, however, important to remember that it is ok to spend money, especially when it is an investment in yourself and your team. Also, being frugal goes beyond finances. In addition to money, time is a precious commodity for entrepreneurs, yet many new entrepreneurs waste time taking on too much too fast. Learn to outsource those areas of your business that are not part of your core competencies and hire people to fill your knowledge and experience gaps.
Focus: To early-stage companies, especially those without the guidance of a board of advisors or investors, everything can seem like an opportunity. Unfortunately, a lack of focus is often coupled with a poor quality of work and wasted resources. Learn to say "no" to things early and often. Remember also that if you do not identify your company's focus and mission early, others may attempt to forge it for you.

2. Use resources that cost nothing.

Since capital is often a major concern for startup entrepreneurs, finding ways to get started without the expense is critical. Taylor suggests three simple things that every entrepreneur can do to ease the burden of getting started -- all of which cost nothing.

Start warming up your professional network by reconnecting with anybody that could serve as an advisor or provide connections to new customers, vendors and other resources.
Manage your personal finances closely, so that you have enough personal savings available to alleviate any pressure or incentive to take much needed resources out of the business.
Plan ahead for worse-case scenarios, so that you will spend your limited time and resources correcting issues rather than reacting to them.

3. Do not go at it alone.

Entrepreneurship is a deeply personal journey, one that can take you emotionally to the brink and back. Unfortunately, entrepreneurs find they are unable able to talk about the experience with friends or family, who without the shared perspective often cannot relate. It ends up making you feel alone and incredibly isolated.

According to Taylor, "I cannot stress enough that you need to talk through this stuff. Finding a co-founder or partner is not enough -- after all, who will you talk about the issues you have with them?"

Taylor suggests developing a strong and trusted network of fellow entrepreneurs with whom you can share and talk about your experience. Groups like the Entrepreneurs’ Organization (EO) can match up non-competitive business owners to confidentially talk through the entrepreneurial problems, which at times just means validating the personal and professional experiences.

Taylor has worked diligently to overcome the challenges of being a solo entrepreneur since founding Square Root. The work has paid off -- in 2015, Square Root was recognized as the number-two best small workplace in America by Fortune.

According to Taylor, "The real key to navigating the startup ship is to always keep things in perspective. Much like life, your entrepreneurial journey will no doubt bring both good times and bad, but while problems may seem insurmountable, remember that all eventually will pass. And when things get really difficult, remembering your personal 'why' will serve as the best motivation for continuing along the road less traveled."