The pros & cons of being a bootstrapping startup founder

Bootstrapping is the minimalistic startup approach, characterised by simplicity, a process whereby an entrepreneur starts a business based on it being self-sustaining, and grows by using limited resources. It’s as much a mindset as a way of operating. Pull yourself up by your bootstraps is believed to have been popularised by American writer Horatio Alger, a reference to C19th high-top boots that were pulled on by tugging at ankle straps.

It means doing something on your own, without outside help, and in many cases, the hard way. Ultimately, bootstrapping is making an investment in yourself, by yourself, for yourself, hope is the fuel of progress. Bootstrappers focus their entrepreneurial endeavours based on passion, ideas and ideals.  For me it’s the real driver of entrepreneurship.

Other people’s money changes everything, it does for sure help you move faster, but there are high costs to be considered – time, dilution and loss of control – in securing funding. But don’t obsess over landing investment, bootstrapping means you are laying the groundwork for growth that is manageable and sustainable. Working solo allows you to refine your own vision for the business, and not adopt an investor-led agenda.

Be eager to learn as you go, and DIY everything you can.  Ditch the hustle mentality. Grow at a speed that works for you and your own circumstances. Starting a new venture is one of the most rewarding things you can do. You have a shot at changing the world, fulfilling your dreams, learning, and growing. You also need to be ready for obstacles, mental and physical demands, and a real risk of a failure.

At times, bootstrapping founders start out of pure passion, a blind belief that they just have to do it, driven by a combination of a hunch, creativity, and obsession. It is like poetry, painting, or any form of art – it just has to come out.  That’s how I was when I started two of my startups, but in retrospect, while I think that passion and obsession are critical, preparing and thinking things through are important.

The primary question is to ask yourself: is this for me? Ignore the Dragons’ Den glamour, the apparent over-night successes and the countless references to unicorns. Be clear about your motivations, drivers and what does success look like to you as a founder. What is your dream in choosing to work for yourself and launch a startup? It’s your choice – ‘Work to Live’ or ‘Live to Work’? Is your mindset that you might be able to avoid the trap of always chasing more?

So be honest with yourself about your skills, experience, and capabilities. I’ve witnessed many I want to be a tech entrepreneur folks driven by ego and the label of status, when the reality is they don’t understand tech, can’t sell it, nor build a team to scale.

Just take a moment to check yourself out. I founded my first startup venture when I was 28. Six weeks later we had our first child. Many thought it was an early midlife crisis. For me it was to escape the inevitable structure of a successful career in professional services that intellectually was a great challenge, but I had to overcome the claustrophobia of expected behaviour and compliance to the culture –  I was told to stop playing rugby and star playing golf.

For me, a startup need not be as demanding, overwhelming, or as lonely as some would have you think. Yes, it’s a tough gig at times, but it is a conscious choice, no one has forced you to do it and my own experience tells me working for yourself has more upsides than downsides. But it’s not for everyone.

The romantic notion of being a tech disruptor or the uber of this is simply an urban myth. You end up wearing the emperor’s new clothes. These people stroll from coffee shop to coffee shop, event to event, convincing themselves that they are doing it. They tell themselves and others they have the capacity to be wildly creative, extraordinarily inventive, and everyone loves hearing about what you are doing. But the till isn’t ringing.

If you’re thinking about bootstrapping a business for yourself, you need to ask Will I enjoy building something from scratch, on my own, and seeing it grow – without knowing if I will get a regular pay cheque? If you can answer yes, then the highs from starting your own venture will be worth the turbulence and the downsides.

To give you an insight into what you’re getting into, let me share some of my own experience, considering the pros and cons, some things for you to consider before you jump in with both feet with your bootstrapping boots.


1. You’ll have the time of your life I put this first, because it’s the reason that I would encourage you to go for it. Starting a new venture may feel like work at times, but boy is it fun. It’s an adventure that you will remember for the rest of your life whether things go well, or poorly. They used to say that everyone should try to be a rockstar at least once in their lifetime. I’m going to add to that and say that in-between being a rockstar and something else, you should be a founder at some point just to test yourself and seize the opportunity. I truly love doing this – the uncertainty, the satisfaction, the failure, the connections with people, the freedom to experiment and simply going with the flow.

2. Release your passion This is the best reason to start a venture if you are passionate about solving a problem that either you have, or you’ve identified. Passion will get you through the tough times as you work to make your startup a success, keeping you motivated when you feel like quitting. It brings meaning and purpose to your work.

Too often, people pursue startups because they sound like good ideas. These are the kind of people jot down in their ‘ideas list’. If you care deeply about solving a problem, and a big company is not the right place to be, then this is a better reason to go out on your own.

3. Fires up self-expression Related to the points above, I think a big part of the reason to bootstrap your own venture is self-expression. Working in an existing company requires you to work on things that align with the company’s priorities. When this aligns with what matters to you, you feel fulfilled, and your work gives you a sense of purpose.

But working for yourself, the process of creating something and releasing it into the world for others to interact with is an act of self-expression. This is what artists and musicians do. Entrepreneurship is no different, creating something from scratch, from a crazy idea you’ve sketched out on a scrappy piece of paper means you’ll have no regrets in life when you look back, and that has to be a good thing.

4. Ownership and autonomy shapes your own destiny As a business owner, you have autonomy and control. If you keep pushing and figure it out, you have the potential for life-changing success and feel on top of the world. There is nobody stopping you except yourself. This is an incredibly liberating feeling. It is a great opportunity to put your own stamp on things and create something memorable.

The autonomy you create with freedom and flexibility means that you decide your schedule, call the shots and get to create a business aligned to your vision. Forget the typical nine-to-five routine, your days aren’t dictated by punching a clock. Instead, you get to dedicate your time to a project you’re passionate about that is centred around your ambitions and an opportunity to fulfil your dreams. No one imposes anything on you.

5. An opportunity for personal growth As a founder, you will need to overcome challenges that will test you. The hurdles are in many ways, blessings in disguise. The challenges you face will contribute to your professional growth and help you evolve personally. From fine-tuning your communication skills to strengthening your problem-solving abilities, starting a business from scratch can be a steep learning curve, but learning is always rewarding.

You’ll meet great people as part of your growth journey, making new friends and connections that will last a lifetime. Networking is a huge part of startup life, and the community of entrepreneurs is benevolent, supportive, and altruistic, helping each other succeed.

These are just some of the positives of starting a startup. Of course, there are potential downsides that you need to be aware of before taking the plunge.


1. Permanent self-doubt As a solopreneur, you never quite know if you are doing things right. Many actions you take are essentially best guesses. This can become frustrating as you may spend time and money on an initiative, only to find out it was a failure. There is a level of confidence that you need to have in order to start and grow a startup. Understandably, there is a great deal riding on your judgement, gut instinct, and business nouse.

An entrepreneur’s ability to persevere through bouts of self-doubt is crucial, which is why working alongside a mentor is something to consider.

2. Constant uncertainty Launching your startup poses inherent risks, including uncertainty even for the most well-planned businesses. Adaptability and resilience are critical traits for an entrepreneur to be able to combat the uncertainty of the unknown. As uncertainty is a cornerstone of entrepreneurship, it’s a good idea to consider the level of stress and uncertainty you’re confident handling before launching your own venture.

Don’t do your own business to work less, you’ll work more than any 9–5 job, and probably with greater intensity and at times you may go backwards. The business is always on your mind, battling the turbulence, there is always something you can find to do. This can be emotionally and physically tiring, know your limits, capacity and boundaries.

3. You need to be a good all-rounder When you start your own business, it’s all down to you – marketing, sales, finance. Nobody can tell you if you are doing things right or not. You have to figure it all out for yourself every day. Much of the early days are trial and error, throwing lots of tactics at the wall to see what sticks.

As above, my advice is to get a mentor to offer guidance and insight, someone who creates trust, provides a sincere, warm relationship, hand on your shoulder.

4. Personal financial risk You’ll need the safety net of savings to cover your cost-of-living expenses at the outset. Many entrepreneurs don’t get a salary for years – that is a lot of missed wages. If the business doesn’t work out, it could all be for nothing. This can have consequences in your relationships and family.

Bootstrapping a startup means unavoidable financial risk. While it can be mitigated by business planning and financial forecasting, there is no way to eliminate risk completely. Therefore, before you start, you should be sure that you are comfortable taking on the personal financial exposure it will inevitably create.

5. Emotional risk Starting a new business can be an emotionally draining, for some this impacts their mental health. You may find yourself feeling isolated, anxious, or depressed during the course of your start-up’s development.

But the worst that can happen isn’t really that bad. If your startup fails you will hurt physically, emotionally, and financially,  but failure at a startup doesn’t mean failure at life. I’m not trying to play down the reality, I’m just trying to say you will bounce back and you will live to fight another day.

So, will you enjoy being the captain of your own small boat? Go for it, the rest will attend to itself. Don’t play it safe, don’t set limits to your ambitions.

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