Lessons From Bootstrapping My Startup

Nothing comes easy at the start. I think that’s the story of any entrepreneur who tries to bootstrap a business—especially those trying to radically redefine a whole industry. ? Going after a big vision while pinching pennies is no joke. It stretches your ingenuity, your persistence, and your negotiation chops to their absolute limit.?

But eventually, things started to change. We began hearing maybe more than “I don’t really understand what it is you do” and then one day even got a yes. The first yes, led to another, then another.?

Building a business is a true test of character, and in some respects, going for investor money makes it easier.? In a lot of ways harder.? I chose the bootstrapping path because I wanted absolute creative freedom, though this has its own price tag.

Let’s dig in.

Evaluating my Resources

Every founder starts with a vision. Or a solution they’ve fallen in love with that they’re dying to build.

I knew what we needed to create at Kaya. For years, in my corporate roles, I’d watched small business, startup, and scale-up leaders struggle to find strategic help that was fit-for-purpose for their own bandwidth, resource constraints and workflows. That needed to change.

But bringing that entrepreneurial vision to life always comes down to how much capital you had on hand.?

The sum total of resources I had at my disposal: a small amount of savings, a business credit card with a moderate limit, some tech subscription promo codes, 25% of a Co-Founder, and a willingness to barter my skills.?

I’m feeling weary just reflecting back on that period. But the key to getting through this phase is rigorous prioritisation. What did Mark Manson say??

“If it’s not a f*ck yes, then it’s a no”.

If it doesn’t immediately move the needle, you shouldn’t spend time, energy or brainpower on it.?

Validating the Model

Are you confident in your product??

Make sure to ask me on a good day. Sure, I knew that there was a market gap. But could we fill it? Did we have the right approach? Am I the right founder to solve this specific problem?

Our strategy-as-a-service model aims to (for lack of a better term) democratise access to expert consultation AND execution horsepower for SMEs. We were creating a platform where on-demand strategic support was no longer limited to massive organisations, and flexible enough to be dialled up or down anytime.?

But validating it seemed like a Herculean task. I got asked on numerous occasions: but how are you possibly going to make the numbers work?

Our approach was iterative. We started by offering a huge amount of value for a nominal subscription fee, proving our model one consultation, one project, and one feature at a time.?

I was quick to scrap builds that weren’t sticking (no matter how much I personally loved them).? And I booked as many calls as possible with small business owners, early-stage founders, and startup investors. I asked them for their biggest frustrations, and how they currently solved them; then whipped up free templates, made an introduction to a brilliant person in my network, or took the initiative to solve a problem for them.??

Truly committing to adding value without the expectation of anything in return was an expensive bet. But it paid off in building gratitude and trust, which in turn led to referrals and introductions.??

There were lots of rejections too.? They stung at first, but quickly became water off a duck’s back.? We got ghosted, strung along, sold to and told to get lost. It sucked but all of this was valuable feedback allowing us to refine our pitch, improve our offering, and hone in on exactly what our ideal clients worry most about.??

Brick Wall Burnout

And then I hit a wall. A big, hard pile of bricks.?

There’s an interesting phenomenon that I’ve talked to a lot of entrepreneurs about. It’s when you finally achieve something or get over a huge obstacle and feel empty and unmotivated.?

It’s called the Arrival Fallacy. Dr. Tal Ben-Shahar explains it as an “illusion that once we make it, once we attain our goal or reach our destination, we will reach lasting happiness.”?

So, when I first started getting some traction with potential clients, I was happy. The model looked like it worked, and Kaya was going to be real. But I was still stressed. Still tired.

This was the entrepreneurial burnout that nobody really prepares you for. It’s the paradox of progress, where every step forward somehow feels like another weight added to your shoulders.?

I’ve written about the hustle-and-grind culture before and how I found peace by working on things totally unrelated to Kaya. These strategies were the only way I could make bootstrapping possible.?

I wasn’t just the first investor in Kaya, I also needed to be its emotional cornerstone. In the end, recharging didn’t mean slowing down. I worked on other things to rebuild my stamina and rekindle my passion.?

And inadvertently landed on other problems to solve.? Beyond Kaya, I am concurrently shipping some other really cool stuff. But that’s a story for another day.

The Path to Profit

Turning a profit is a huge milestone for new businesses. It validates all your hard work, eliminates doubt, and gives a glimpse into a sustainable future. Fortunately for Kaya, it came quickly, but that’s largely due to a couple of key decisions:

1. Using only low code or no code tools until we achieved early product-market fit; and,
2. Paying staff and contractors above market rate, while underpaying myself. Choosing to attract great talent ahead of the curve and reward them for taking a risky bet on you pays dividends.? In saying that, paying myself enough to meet expenses (so I’m not stressing about making ends meet) was critical.?

Reaching your first profitable month is like drawing a full breath after being underwater for too long.? Despite this awesome milestone, it is still important to scrutinise every expenditure, double down on strategies that produce results, and never hesitate when you need to pivot from those that don’t.?

Break-Even

A profitable month does not mean a profitable company though.?

Every startup marks milestones differently, but few are as critical as the ‘break-even’ point. At Kaya, my Co-Founder Jake ensured we meticulously recorded every penny spent and every penny earned, so that we knew how far we had to go.?

We invested early in a fantastic accountant who, well, holds us to account and helps us plan ahead for taxes.? And we regularly pay back money invested by us in the early days to clear the deck.?

When cumulative revenue finally matches investment, you’re suddenly playing with house money. But let’s not sugarcoat it. The pressure leading up to this point can be immense. Cash flow management is your scripture, cost-cutting your daily prayer.?

You constantly ask questions like:

• Are we spending wisely?
• Can we find cheaper alternatives (without sacrificing quality)?
• What can we do to boost revenue without additional outlay?

We’ve all heard the stories of tech startups sinking millions and millions of investment dollars into a product that never breaks even. Bootstrapping is nothing like that. If you don’t hit that mark quickly, you’re dead.?

My caution to every entrepreneur I’ve worked with: never build anything unless at least a couple of customers have asked for it, and over 10 prospects have said that this feature/product will get them across the line.?

I hesitate to say “if you’re lucky enough” because it diminishes the hard work, but let’s be honest—some of it is luck; defined as preparation meets opportunity.? Do the market research, time your venture well, and you’ll be rewarded for it.?

If you do hit the break-even point, celebrate! It affirms your team’s relentless drive and lends legitimacy to the business. It means you’re moving forward.?

Back in Black

Profitability (being “in the black”) doesn’t just mean there’s extra money in the company bank account. It represents opportunity, stability, and the capacity to invest in new growth strategies.?

Here are some ways you can start spending those profits.?

Reinvest in the Business

The first instinct is to splurge. Resist it. Smart entrepreneurs know that early profits have to be funnelled back into the company. That could mean upgrading outdated equipment, investing in productivity software, or developing that new product people have been asking for.?

In short, spend money to make money.

Build Your Emergency Fund

All of you founders have a six-month emergency fund tucked away, right? No? I didn’t think so. No matter how many financial advisers tell us to build a buffer, it’s extremely difficult to actually achieve—especially over the last few years.?

When you start making some profit, shore up those reserves to cover unexpected expenses without taking on debt.

Reward Your Team (and Yourself)

People are the backbone of any successful venture. Acknowledge their role, and reward them for it.?

That doesn’t necessarily mean handing out raises and bonuses like candy. It can be through other business-boosting methods, like hiring administrative assistants, splitting one role into two, or outsourcing some of the more mundane tasks so that team members can focus on what gives them joy.

And don’t forget to ensure you pay yourself something more reasonable too.

A New Opportunity

Every opportunity that knocks carries the risk of overextension. Diving headfirst can dilute focus, strain resources, and detract from your core value proposition.?

Being approached to become the platform of choice for accelerators and incubators around the world? YES!! I was over the moon.

But before moving forward, I had to evaluate this new path. Does it align with Kaya’s mission? Can we deliver the same level of quality and service on a much, much larger scale?

And critically, what would we have to say ‘No’ to, in order to say ‘F*ck Yes!’ to this?

New markets can be seductive. Like the siren drawing sailors into the jagged rocks, they can be dangerous to the whole boat. The ability to discern an opportunity from a distraction shows an entrepreneur’s maturity.

Chase the right opportunities, not necessarily the most lucrative or flattering. Weigh them against your vision, resources, and passion to ensure you’re backing a winner.