Bootstrapping our startup: 5 benefits of starting with $0

If you think your bootstrapped startup needs investment to succeed, here are some benefits to remaining bootstrapped from our personal journey.

Disclaimer: Although we've won a small local investment competition in the past, our experience is that we are 99% bootstrapped.

Pick your favorite startup program or boot camp. The first milestone after achieving problem/solution fit (or sometimes product/market fit) is to raise investment.

Go to school -> go to college -> get a job -> start a family
Startup idea -> kinda validate it -> raise invesment -> ??

Just because a road is popular for some, doesn't mean it's the only way or even the best way. I learnt that everyone's journey is 100% unique to them.

I know you know this, so let's carry on.



In this article, I wanted to share what I learnt about the blessings of being bootstrapped.


Disclaimer 2: Currently, I suck at raising capital, and we're better at sales. Both fundraising and bootstrapping have their benefits. This essay is about why we love being bootstrapped and hope to stay that way for as long as we choose to.

"The game I’m in is maximum happiness for the maximum amount of time. What I found is one of the things that makes me really happy is to work on stuff that I care about with people I really like working with, with the independence of nobody telling me what the fuck to do."

-David H. Hansson, Creator of Ruby on Rails, partner at 37signals


Benefit 1: Bootstrapping teaches you persuasion skills

When you don't have money, you can't buy everything you want. For any ambitious entrepreneur this is problematic, to say the least. 

I often ask myself on a weekly, nay, hourly basis:

"How can I bridge the gap between what I want and what my resources would allow?"

One of the books that had a profound effect on my life and how I run our company is The Obstacle is the Way by Ryan Holiday (Ryan, if you ever read this, thank you for existing). 

When something happens, before you cast judgment on it, pause and see how you can perceive it in a way that brings you benefit. Also, to love what is currently going on in your life; to not just tolerate it, but to realize that you are actually BETTER off thanks to it. Without it, you would've been worse off.

No cash? Great! Time to learn how to sell.

I had to persuade my initial team members to join us, knowing full well that I was unable to afford their true worth (or never will be). 

To do that, I had to go on Google and research reasons people join companies beyond money.

I was reminded that in many (not all) cases, money is not the first thing people look at.

• Freedom.

• Autonomy.

• Growth.

• Meaning.

Yep, I can definitely offer that. What else?

• Making them feel like owners in our product roadmap.

• Giving them a platform to publically leave their impact (to see how they're helping real people out there)

This worked in many cases. In other cases, I was flat out unable to afford them. 

Of course we appreciate senior talent just as much as the next company, but if I can't always afford that, how can I get around it?

"Ya* Kareem, the obstacle is the way" - I tell myself, or maybe it's Ryan's voice in my subconscious.

Alright, how do I apply the obstacle is the way here?

What can I afford? Junior talent.

How can this work?

-They're not set in their ways. They can be truly original thinkers and bring that value.

-They are happy to learn and grow on my dime.

-I can teach them what I know and fill gaps with links to YouTube, books, and other learning material.

-I'll encourage them to teach us what they learn

Ya* - Egyptian slang for getting someone's attention. Helpful especially in Cairo.

[Quick TL;DR about what you're reading]

If it's your first time here, I'm Kareem Mostafa - co-founder at tribetactics and chopcast. We're on a mission to help 1,000 brands repurpose webinars and podcasts into binge-worthy, bite-size clips to drive conversations and grow influence faster. In these essays, I'll be documenting what we learn in hopes of building a community that can relate & teach us as well.


Benefit 2: Bootstrapping teaches you sales skills

"Entrepreneurs are natural-born sellers." 

Oh, how I wish that statement was true. 

We had to learn how to sell. Hard as it may seem.

Our motivation was simple but powerful. 

No sales, no paycheck. 

It forced me to wake up and pay attention.

We're in constant learning about personas, the jobs to be done (JTBD) framework, the Challenger Sales model, Product-led Growth, and doing things in our power to do to continuously get better at attracting the right type of people to our business.

If you enter my head, you can find me sipping coffee and pondering: 

"Is what I'm doing teachable, repeatable and scalable?" 

If the answer is no, that's OK too. As long as I'm not doing something stupid with my time.

I recognized that some things that are meant to be done at the start are designed not to scale.

When you bootstrap your company, take pride in your pursuit of becoming self-sufficient by investing in learning how to sell.

Selling can feel scary, but that's because we over-complexify it, just like I did with that word.

I learned to think of sales simply as finding the people who will be absolutely grateful you reached out to solve their problem.

Joe Polish quotes Dan Sullivan's definition of sales, which I recommend to you also:

"Selling is getting someone intellectually engaged in a future result that is good for them and getting them to emotionally commit to take action to achieve that result."


Kick yourself out of your building, bury the keys, and start selling.

You really can't afford to outsource sales at the start, both in the literal sense (you may not afford salespeople at the start) and also in the figurative sense.

As a founder/founding team, you need to get comfortable with selling for the purpose of learning because you should know your customers best, not your newest hire (or intern!) who doesn't know your company yet.

How will they know it if you don't even know it? 

If you approach so-called sales meetings as customer-development meetings, it will bring down the guard of your prospects enough for you to have a meaningful conversation, and you both will naturally know if it makes sense to work together.


Benefit 3: It also teaches you creativity

"We need to run ads."

"Ads definitely work, but you need a lot of cash for it to work."

"We need to X but it costs Y more than what we can manage."

We don't have money to pursue ads meaningfully. I'm just being honest. We also don't have money (yet!) for a lot of things we'd love to be able to afford.

IKEA inspired me.

Not with their standing desks and sit-down sofas, but the walls of their showrooms.

I remember walking around their showroom floor where you get inspiration before you actually go downstairs and do your shopping. On one of the walls they had a quote that I wrote about more in my book

"Limited spaces, unlimited creativity."

You and I will always have more ideas than we have time and money to do. 

If I give you a piece of paper and a crayon and tell you to draw "anything", this is a lot more difficult than me simply telling you to draw a car.

It's easier because it brings a singularity of focus on the limitations at hand.

By bootstrapping our company, we have thought of some supremely unconventional ways (at least for us) to do things that have served us well.

For example - we always wanted to build a product business, but we had no cash and no coding experience to do so.

We honestly had nothing except an imaginary use case for a fictitious product if it ever exists one day.

So me and Aamen, my co-founder, behind hard on ourselves by nature - we decided to do something unpopular.

We created what we thought would be a temporary, caveman version of what we really wanted to do.

Luckily*, this gained traction with a select niche of companies that we're currently growing, and what was gonna be a one-and-done experiment to fund our product ended up becoming a permanent and significant part of our business, one that can complement our product.

A lot of people may frown at this approach, so I'll just take comfort in knowing that MailChimp started out as a service too.

Luckily*: hard work + frequent fails + persistence + coffee

It also taught us that there is magic in building an ecosystem of products and services working together. 

When you bootstrap your company, consider all the conventional things bigger businesses than you do and take for granted.

Make it a game to think about how you can creatively think of a different way of doing things that will serve you.

After all, as Derek Sivers says in his book Anything You Want, your business is your own universe, and you control the laws in your universe.

If you want more examples of how we applied this, just DM me or comment and I'll do it.


Benefit 4: It teaches you self-discipline

When you work for someone - discipline, structure, targets, and metrics are all part of the party.

It just happens. You just need to be an active participant.

When you have investors, this is also the case, but perhaps with a bit more autonomy than a corporate job.

When you're bootstrapped? Oh man, you're honestly on your own.

Good luck navigating a ship with no map.

Early on I was two-chicken-wafers-and-a-toast-for-lunch bootstrapped. Long gone are the days of fancy lunch menus courtesy of my previous employers.

Necessity breeds innovation, and I can credit being boot-strapped with helping us increasingly get more self-disciplined with our reporting, targets, metrics, and overall performance. 

It's not investor money you're spending, it's your own. 

It's not your employer's time, it's your own.

When you're bootstrapping, know that you can bring the best of what you've learnt in your past corporate and education experience, examine it objectively, and bring the best parts of it to your current company. Or better yet, create a new playbook that you will be self-motivated to follow through on. 

Self-discipline is not a requirement to being bootstrapped as much as it is something that bootstrapping will beat out of you whether you like it or not. And I love it.


Benefit 5: Realizing that it's your world.

You may think it's impossible to raise investment. With hard work and grit, you will have to build a more solid, more proven business that allows you more leverage when raising investment, or the confidence to continue bootstrapping.

I'm learning that while we are bootstrapped, we cherish it more and more, and want to maintain it for as long as it makes sense for us to do so. We love the freedom of charting our own course. The freedom of picking what to work on next. The freedom of choosing who we want to work with. I invite you to cherish being bootstrapped and recognize 

Learn to value happiness and not just money. I'll leave you with the quote I shared earlier:

"The game I’m in is maximum happiness for the maximum amount of time. What I found is one of the things that makes me really happy is to work on stuff that I care about with people I really like working with, with the independence of nobody telling me what the fuck to do."

-David H. Hansson, Creator of Ruby on Rails, partner at 37signals

What other benefits of bootstrapping did I miss? Share them below :) 

P.S: If you create webinars and podcasts, sign up for chopcast for free to turn them into tons of bite-size clips in just a few minutes.




Similar posts

Join our newsletter

Stay in touch with all things content repurposing.