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3rd September 2025

From Side Hustle to Funded Startup: Why I’ll Back You Before You Quit Your Day Job

Startup culture loves the “burn your boats” mythology — the idea that true founders prove their commitment by quitting their jobs, going all in and betting everything on their vision.

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From Side Hustle to Funded Startup: Why I’ll Back You Before You Quit Your Day Job
Financial analysts analyze business financial reports on a digital tablet planning investment project during a discussion at a meeting

By James Baker, Jersey-based award-winning entrepreneur and angel investor

Startup culture loves the “burn your boats” mythology — the idea that true founders prove their commitment by quitting their jobs, going all in and betting everything on their vision. It makes for a great story when it works. But more often than not, it’s a reckless gamble that does more harm than good. So, why is the industry so centred on pushing founders to go full-time?

The Smarter Path: Slow and Steady

The idea that the only way to be taken seriously by investors is to go all-in from day one is misguided. It overlooks the crucial fact that sustainability will always matter more than speed. When founders are financially stretched, emotionally burnt out, and under pressure to generate immediate revenue, poor decisions follow. What the startup ecosystem needs is a shift in perspective that values thoughtful, gradual growth over reckless urgency. Founders who keep their day jobs while building their business aren’t less committed — they’re more strategic.. They know that no matter how much faith they have in their business, they can’t rely on immediate success, and retaining a stable income during this phase can give founders much-needed breathing space.

Without the urgent pressure of needing the business to pay the bills, founders can focus on making better long-term decisions, testing the market and building a product that people want, rather than one that pays next month’s bills. In other words, to create a healthier, more resilient business.

In contrast, founders who go full-time too early often find themselves scrabbling for customers, rushing decisions and pivoting reactively. They’re working in survival mode, not thinking of long-term prospects.  So, why does industry culture still push for full-time commitment from day one?

Why the myth persists

The main problem here is the damning perception that if you’re not 100% focused on your business, you’re not serious about it. On the surface, it makes sense, but that logic is flawed. Because commitment is about so much more than the hours you can put into a venture; it’s about the decisions you make, to make it work. 

Investors also need to learn to look beyond their own convenience. There’s no getting away from the fact that it’s easier to track, manage, and benchmark a founder who’s working their new business full-time. But if you want the best returns from your investment, you need founders who have the creativity and determination to solve problems their own way – and that might mean accepting different working models.

Why I Back Side Hustlers First

As an investor, my main priority is funding companies and individuals that I believe in. That doesn’t mean that I don’t seek sound fundamentals; of course, the metrics matter. But I also need to see founders who are willing and able to go the distance, in whatever way ensures durability for the business.

So, a founder who’s still working elsewhere doesn’t signal a lack of commitment; they’re showing me that they’re able to juggle multiple priorities and manage risk intelligently. Both are highly desirable qualities in a founder. It also shows more considered decision-making, and a willingness to wait to get things right before throwing everything they’ve got at the market. And beyond that, it shows resilience, because these people are weaving their own safety net. They may not go in “guns blazing”, but the companies that build cautiously often prove the most resilient — precisely because they’ve resisted the heroic but fragile all-or-nothing mindset.

Time for Investors to Catch Up

It’s time for investors to stop penalising founders for being responsible. They don’t need that pressure. And they don’t need to quit their job to show commitment. Supporting side-hustle founders requires more patience, but it delivers better returns.

It’s time to retire the all-or-nothing narrative. The best founders don’t just take risks — they manage them. As investors, we should reward discipline, foresight, and staying power. That’s what builds companies worth backing. And if you can’t see that, then maybe startup investment isn’t for you.

James Baker is a Jersey-based award-winning entrepreneur and angel investor. As a former Government Minister, with a background in the military, he has a wealth of multi-disciplinary experience and a diverse portfolio of international business interests. His experience spans sectors as varied as digital media, adventure tourism, healthcare, ecommerce, recruitment, and AGV development.


Categories: Articles, Finance/Wealth Management, Markets & Assets



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