6 powerful strategies you should know for successful bootstrapping

Bhupendra Sharma
6 powerful strategies you should know for successful bootstrapping

It can be challenging, but if you succeed, the rewards can far outweigh being tied to venture capital money

With all the news always being focused on how much money is being raised by unicorn startups, let’s look at the bold reality of many entrepreneurs and businesses who decide to take a different road: bootstrapping.

Bootstrapping is notoriously hard, can be slower, and can even be limiting. But when a bootstrapped business succeeds, the rewards can far outweigh being tied to venture capital money.

I had a very honest discussion with a highly successful bootstrapped startup founder, Stefan Pretty, CEO of Subbly – a subscription e-commerce platform empowering entrepreneurs. During the conversation, a lot of wisdom came up about his bootstrapped business journeys and I have condensed some of those nuggets into this guide to help other entrepreneurs bootstrap with their business.

Full disclosure, bootstrapping is just one way to start your business, there are pros and cons to being funded, self-funded and bootstrapping.

Here are 6 tips (and a bonus) to increase your chances of bootstrapping success:

1. Be Prepared For Rejection And Criticism – But Remain Persistent

Often when bootstrapping you’ll face rejection and criticism for your approach, or even towards your business idea in some cases. People may not believe in you and think that you should do it the tried and tested way – by raising money. In some cases, they may simply think that it’s impossible to achieve success with your business model and idea.

You must learn to see past this negativity and set boundaries for yourself.

You must be stubborn and determined enough to keep believing in yourself and your gut and what originally inspired you.

Sometimes you will need to carry yourself through hard times. That’s why you should choose something you’re passionate about to keep you inspired to keep going.

Trust in your gut and keep going until you have clear signs your vision and assumption is wrong.

Stefan said, “there were moments where I considered giving up when starting Subbly, but I knew deep down I had to keep going on this path, I had to trust my instincts, even if I was wrong.”

2. Don’t Take “No” For An Answer

Most of life is filled with different forms of rejection, or failures. But when bootstrapping you must be prepared for this and keep focusing on the wins and remaining positive.

Continuing to build your resilience and pushing towards your goal is what will help you to be patient to achieve your goal.

It only takes one “yes” to change the entire game and help you on your way to success.

Keep going!

Also read: Bootstrapping your startup? Here are 7 tools you can use to make launch and growth easier

3. Avoid Temptation – Personally And Professionally

Life is always full of temptations. That dessert. That drink. That investment offer. The easy path, the path full of pleasure is so easy to walk down but it also doesn’t move you towards your goal.

When bootstrapping you must remain disciplined.

Of course, it goes without saying, you must reward yourself and look after yourself, physically, mentally and spiritually.  You can’t perform without having your best self-put forward.

You’ll know deep down when you’re giving into temptation. Listen to that.

4. Always Be Planning

Planning is essential according to Stefan, “I spend a large chunk of my day planning and processing, I believe it’s important to listen to your intuition and to not rush into poor decisions”.

This is something that continually comes up amongst the most successful. It seems balance must be struck between logical evaluation and listening to your instincts.

Furthermore, it’s pretty clear that instead of writing a set plan, you need to always been planning and responding to the market and customers etc. Be aware of analysis paralysis though. You need to make sure you’re not going in circles – that’s where intuition comes in.

5. Take Meaningful Massive Action

In addition to giving yourself time to process and evaluate decisions always, the final key is to act on it when you’re certain and do it properly.

Stefan said, “I learned that it’s easy to keep taking micro-actions for small wins, but the times where the needle was really moved, was when I was taking massive action. Usually the thing I was dreading doing.”.

A massive action could mean it’s the thing you are putting off or don’t want to to do but Stefan aptly added, “I believe the way forward is the path of resistance”. In other words, often the hardest thing needed to be done on your list might make the biggest difference to achieving your goals.

6. Stay Lean – Iterate And “Move Fast And Break Things”

It’s clear that amongst all startups the approach of being LEAN is the best way to validate and grow a business efficiently. Stefan preaches this to new entrepreneurs that he talks to.

The process, in a nutshell, is simple: create an assumption, validate it by doing the minimum version, collect feedback, evaluate and then make a new assumption. Meanwhile, if you’re assumptions are right, double down and perfect those.

It’s a feedback loop and it’s essential to not waste resources and to build what the market needs.

Also read: The good, the bad, and the ugly of startup bootstrapping

Bonus: Know When Is Truly The Time To Walk Away

Sometimes, we’re wrong in our assumptions, even if it is a project or your entire business. However, it seems that aside from being persistent and moving in the face of resistance and rejection, there is a point where you need to draw a line in the sand. It may be a subjective line, based on your own limits, but it may purely be metric based.

In any case, know when to walk away if necessary. As Stefan emphasized his beliefs on listening to your intuition, this is where this matters the most.

Closing Thoughts

With all that said and after talking to many entrepreneurs, doing research, and having an honest real conversation with Stefan, ultimately it’s your journey and comes down to what works for you, but I hope this helps give some guidance on your own bootstrapped journey.

Above all else, believe in yourself and don’t give up.

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Photo by HB Mertz on Unsplash

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