Why We Should Invest In Today’s Gen X Bootstrapping Entrepreneurs

Photography by Sammie Vasquez

Does success only come from a combination of commitment, resilience & continuous hard work? Or is there an easier & shorter way? This is a question, most GenX entrepreneurs (those born between 1969 and 1978) often ask themselves. I’d know because I do ask myself this at least once every day!

The current social landscape paints entrepreneurship as more of a youthful endeavour where there is intense passion & extraordinary tech savviness added to the above mix. But is that the real picture? What do GenX entrepreneurs bring to the table then? Their years of experience tackling real-world problems using excellent pragmatic problem-solving skills.

This leads us to the important question – why should investors invest in GenX entrepreneurs? In the last decade, I have spoken to hundreds of entrepreneurs in my generation and I’ve identified five facts that make GenX business owners and founders invaluable investees:

#1: They have a deadly rare combo: grit + experience

Starting a business is hard, bootstrapping it is even harder. This means slogging through small and big tasks with very limited resources. It can be daunting and sometimes even harmful for mental health; only an inner grit can take a founder through that and maintain their sanity to function optimally every single day. The power of grit is amplified 2x times when the founder has the years experience required to push the business in the right direction.

If you are a bootstrapping founder in your forties into your third year, chances are you made it to the third year with the deadly combo!

#2: They are ultra-resourceful

When someone starts a business in his or her forties, this usually means two things: either it’s at least their second business or it’s their first backed by at least 20 years of professional experience. In both cases, it adds great chances for success.

Last year, (which was the third year into my business) I took on multiple consulting gigs up to 50% of my time for over 12 months and re-injected all the revenues into my company to grow my team, invest in new software, etc. I often describe it as one of the most exhausting periods in my life but it was only possible because I had enough expertise and experience to ‘sell’ instead of selling equity to get cash. Still today, I own 100% of the company, expanded my professional network and grew the business.

#3 They are the last technology-resilient cohort among humans

If you’ve met an entrepreneur in their forties, you’ll see they have fully adopted technology, are social savvy and are able to be at the top of their game even if they grew up without the internet, without the mobile phone and without social media. Despite not ‘growing into,’ technology, they are still super tech-savvy and completely embraced technology.  

This also means that they are the generation who owns two old social behaviors and though  they may be overwhelmed at times, their resilient nature makes them persistent adopters and innovators while harvesting their long hard-earned experience.

#4: They have another killer combo: hard work and smart work

This is my favourite. Founders in their forties understand that success comes from both smart and hard work and not smart only. In my generation, born in mid-seventies, we never quit a job before we have at least tried from 2 to 5 years in one company. We have witnessed the full cycle of trying hard, making mistakes, getting up, repeating and then savouring success. This could only make us smarter. This cycle is so similar to the one of bootstrapping. In my experience, I felt that resilience and trial over a reasonably extended period of time enabled me to appreciate a valuable learning cycle and intuitively know when to stop trying – not too early and not too late. As a startup founder if you have that ability you are very strong!

#5: The lowest risk investment one can ever find

Very often we look at successful businesses and they all have one thing in common: they are either bootstrapped or had a very small investment from angels, family or friends. In fact, so small it could barely take the founder (s) through the product development period, let alone the product-market fit period.

When a startup founder who has bootstrapped his or her business for years and finally decides to fundraise, it’s usually good news for the investor. Imagine if you had to invest in a proof of concept rather an idea? In an individual who usually has invested everything he or she had WITHOUT quitting.

Investing in people who have good ideas is great but in those who have transformed their ideas into real impact is another.

Investors want to be investing in founders who have tackled a real-world problem and who have gone ahead to create a lasting change.

So go out there, find your gold miners and invest in them, now.


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