Part 2: Does Having A Side-Hustle Help Or Hinder Entrepreneur And Founder Development? The Experts Weigh In

Side-hustles aren’t one-size-fits-all, and that’s exactly why the conversation around them keeps evolving. Some entrepreneurs swear by them as a way to stretch skills and explore untapped opportunities. Others see them as a potential minefield of distraction and stress.

So, why do opinions differ so wildly, and how does context, personality and goals shape whether a side-hustle is a boost or a burden?

This isn’t just about productivity hacks or work-life balance – it’s about the nuanced ways founders experience and interpret side projects, and why the same approach can feel liberating to one person and limiting to another.

 

Perspective Matters: Why Do Founders See Side-Hustles So Differently?

 

One of the most surprising things we found when speaking to experts is just how polarised views are.

For some, side-hustles are mini playgrounds for experimentation, letting founders test ideas, expand networks and explore industries without fear. They talk about side projects as “sandbox environments” where creativity flows and lessons are learned quickly.

Others, however, caution that the impact isn’t universal. What works brilliantly for one founder can feel like a constant drain for another. Factors like personality, current workload and business stage heavily influence the outcome. A highly structured founder may thrive juggling multiple ventures, while someone who thrives on deep immersion may find side projects fragment their energy.

Even among seasoned mentors, advice differs.

Some encourage side-hustles as a safe way to explore new revenue streams or product ideas, while others argue that splitting focus early can slow progress and dilute the leadership vision. At the end of the day, it’s not about right or wrong; it’s about fit. A side-hustle that energises one founder could exhaust another.”

This diversity of opinion underscores a key point – that is, the value of a side-hustle isn’t fixed. It’s shaped by context, intention and the individual’s capacity to manage multiple creative and business streams. Understanding that nuance is essential for founders trying to make an informed choice.

 

 

Here’s What The Experts Have To Say:

 

• Fineas Tatar: Co-CEO and Productivity Expert at Viva
• Judit Mora: CEO and Co-Founder of Nuumad
• Olivia Parks: Owner and Lead Organiser at Professional Organiser New Orleans
• Lindsey Mignano: Venture Financing Attorney at SSM Legal
• Darian Shimy: CEO of FutureFund
• Liz Benditt: Founder and CEO at The Balm Box
• Ross Buhrdorf: CEO and founder of ZenBusiness
• Thomas Fighter: Founder and Criminal Trial Attorney at Fighter Law
• Elle Farrell-Kingsley: AI Curator, Dialogue Writer and QA Editor at Big Tech
• Hans Scheffer: CEO of HelloPrint
• JM Ryerson: CEO at Let’s Go Win
• Vishal Kumar: CEO and Co-Founder of Camera Intelligence
• Gary Ross: Founder and CEO at Blip Insurance
• Lee Holmes: CEO of INFINOX

 

Fineas Tatar, Co-CEO and Productivity Expert at Viva

 

 

“It goes both ways. Side hustles can either sharpen skills or weaken the capabilities you have. Look at it from a timing and intent perspective. If your main venture is currently going through challenges or it’s at a growth stage, you cannot risk constant context switching just to satisfy curiosity. It may cost you time, money, and attention.

“However, if the side hustle is something small that can benefit your skills as a founder, it’s definitely worth continuing. For example, if you’re in retail, you can develop a new product that lets you test a new market.

“Personally, I follow this rule: the main company should benefit from your best energy and clearest hours. If the side hustle you have makes you a better leader and helps in execution or allows you to become better at prioritizing, then nurture it. If it does otherwise and just depletes your energy, you may want to let it go for now.”

 

Judit Mora, CEO and Co-Founder of Nuumad

 

 

“Having a side hustle can be really helpful for founder development. When I was building Nuumad, I was also working two other jobs, and those early side hours were where we could experiment, test ideas, and shape the company in a thoughtful, user centred way. Of course, it’s important to manage your time, but a side hustle can give aspiring founders space to grow, build confidence, and gain experience before going all in. For me, it was an invaluable stepping stone that made taking the leap to Nuumad feel much more manageable.”

 

Olivia Parks, Owner and Lead Organiser at Professional Organiser New Orleans

 

 

“I definitely believe that side hustles can be incredibly valuable for founders. Side hustles enable you to try a variety of different things, exposing you to what you actually enjoy and are naturally good at.

“When I graduated from college, I started nannying and working as a household assistant for families while applying for full-time jobs. I was trying so hard to find a job that “fit”, but nothing felt right, and I honestly had no idea what direction I wanted to go in.

“What I didn’t realize at the time was that the side hustle I was doing was the direction. By being inside families’ homes, helping with daily routines, and keeping families on track and organized, I discovered my true calling, which ultimately led to the six-figure home organizing company I own today.

“In my opinion, side hustles are great because they force you to try things, pay attention to what comes naturally for you, and help you figure out what you like and don’t like. That’s how you figure out what direction and path you’re actually meant to go in.

“For some people, side hustles are a distraction, sure. However, for aspiring founders, they can be a clear path to understanding your ‘why’ and what you are meant to do with your life and career. I’d recommend side hustles to anyone trying to figure out their career or entrepreneurial path, especially those who feel lost or stuck.”

 

Lindsey Mignanom, Venture Financing Attorney at SSM Legal

 

 

“A side-hustle can help or hinder founder development – and the effect depends on why you’re doing it, how you structure it, and what stage your startup is in.

“From a skills perspective, a founder doing contract work for small businesses that are the key customer base of his startup may sharpen customer empathy and GTM instincts.

“Second, reducing founder personal financial pressure can extend the founder’s personal runway and prevent them raising prematurely. On the other hand, a side hustle can take away from the founder’s focus on building his startup and there can be legal trouble if the ownership of the IP (startup versus side hustle) is not clear.

“Furthermore, if the side hustle in any way competes with the founders’ main business (the startup), the founder could be liable for breach of his fiduciary duties as an officer and/or director of his startup.

“Finally, investor optics may sour as an investor of a startup may see the founder’s time spent on his side hustle as a lack of dedication to building the startup at hand.”

 

Darian Shimy, CEO of FutureFund

 

 

“Based on my experience, a side hustle can either be a very valuable asset or a serious liability. The differences tend to come down to intent. When a founder uses a side project as a legit way to experiment, learn, or explore unique ideas they can’t pursue at their main company, it tends to be a great way to strengthen and broaden their way of thinking. From personal experience I have found that stepping into a different context can reveal blind spots and spark solutions I wouldn’t have arrived at otherwise.

Saying all of that, the second a side hustle becomes an escape from the hard problems that you should be solving, it works against you. I have always operated where founders owe the team clarity, consistency, and presence. If a side project take away from that, its no longer serving growth.”

 

Liz Benditt, Founder and CEO at The Balm Box

 

 

“For me, teaching as an adjunct professor has been an invaluable strategic side hustle while building The Balm Box. It provides access to world-class academic research, which continually sharpens my thinking as a founder and fuels innovation that directly benefits my business. The modest income also created financial breathing room in those early years, allowing me to support my family without pulling precious capital out of a young company.

“Perhaps the most unexpected benefit is talent: I even hired one of my former students, whose fresh perspective and digital fluency have been a tremendous asset.

“A side hustle shouldn’t be a distraction – it should be a multiplier. When chosen intentionally, it keeps founders mentally stimulated, connected, and resourced in ways that accelerate – not hinder – startup success.”

 

Ross Buhrdorf, CEO and Founder of ZenBusiness

 

 

“A side hustle can be one of the best training grounds for entrepreneurship. I know that personally because every business I’ve ever started was originally a side hustle, including ZenBusiness. I’ve watched hundreds of thousands of people use a small project to build the muscle memory they need to eventually run a full business.

“A side hustle can help an entrepreneur test ideas, understand customer needs, and build time management skills without a 9–5 structure. Intentionality is key, and the founders who benefit most treat their side hustle as a place to experiment and learn, not just earn. It gives them real-world insights without the pressure or risk of going all-in too soon.”

 

Thomas Fighter, Founder and Criminal Trial Attorney at Fighter Law

 

 

“A side hustle can be good if it provides you with another MENTAL SPACE to think, learn and reset. When I did take on occasional small teaching or consulting projects outside of my main practice, they helped me see problems from fresh angles. Those moments helped sharpen my communication skills and think of how I would manage my team later on. That kind of clarity can come from a side project, but only if it serves the main mission rather than distracts from it.

“A side hustle can also be a distraction. I found myself at one point in my career undertaking too many obligations all at once — legal writing assignments, volunteer commitments and firm duties. Though everything was meaningful, it stretched me. I did a less effective job because I was splitting my focus. I assessed if the extra project adds any value at all or is simply another obligation. The balance matters, especially when clients hire you to represent cases where they have had their safety and rights violated.

“Be STRATEGIC about the side hustle. If what the project builds is a skill that you really need — if it’s leadership, communication or financial discipline — it can enhance your founder work. A side hustle should have CLEAR BOUNDERIES –you’re safeguarding your focus — and sparing yourself a burnout. It’s an asset, not a distraction when tuned with the right structure.”

 

Elle Farrell-Kingsley, AI Curator, Dialogue Writer and QA Editor at Big Tech

 

 

“I’ve noticed people often assume I’m a disciple of the grind and hustle culture because I’ve balanced full-time roles with freelancing and a growing portfolio of passion projects. But my view is far more nuanced. I’m fully for people exploring new ideas, taking on small adventures, and holding onto the stability and safety of a salaried position while they test or transition into something of their own. A side project can spark curiosity, creativity, and even clearer thinking for the main venture.

“But what I find troubling and frankly abhorrent is when a side hustle becomes something someone needs just to stay afloat. That signals a society slipping, a social contract cracking. It reminds me of Melville’s Bartleby, quietly resisting the machinery of meaningless labour. When the 9-5 demands a 5-9 simply to survive, the system, not the worker, is the problem. A creative or exploratory outlet shouldn’t become compulsory overtime.”

 

Hans Scheffer, CEO of HelloPrint

 

 

“I believe side hustles help founders more often than they hurt them, but only when they’re aligned with your bigger mission. A small project on the side can help keep you creative and give you a space to test ideas you’re not ready to roll into the main business. In my own experience, those experiments sometimes lead to the breakthroughs you bring back later.

“But there’s a line. If the side hustle pulls your energy away from the core team or stops you from thinking long-term, then it’s more of a distraction than a value. The idea is staying honest with yourself. Keep it if it fuels you and cut it if you’re feeling drained.”

 

JM Ryerson, CEO at Let’s Go Win

 

 

“In my experience, the most successful founders are rarely building just one thing. Every high performer I know has a side project that keeps their mind sharp and their creativity alive. When all your energy is locked inside a single company, pressure narrows your thinking and every setback feels bigger than it is. A side hustle breaks that pattern. It gives you a separate arena to test ideas, fail cheaply, and stay innovative without risking the core business.

“The mistake founders make is assuming a side hustle dilutes focus. It only becomes a distraction when you treat it like a second full time job. When you approach it strategically, it becomes a release valve and a perspective builder. Side hustles don’t pull founders off course. More often, they expand the vision and resilience needed to build something that actually lasts.”

 

Vishal Kumar, CEO and Co-Founder of Camera Intelligence

 

 

“For me a “side-hustle” is only a distraction if it’s unrelated to your primary mission. If it’s strategically aligned, it’s not a side-hustle – it’s a distribution channel.

“My journey is a perfect example. I was a cultural data scientist at Sotheby’s and started creating content about my role. That “side-hustle” helped me build a community of 30,000 followers.

“As a founder, now that community – as well as the other creators I’ve met – is our initial adopter base for Caira, our intelligent camera. My side hustle helped me build a pre-vetted customer list, which significantly lowered our customer acquisition cost.

“So, does it help or hinder? For me, it was the single most valuable asset I built. The right “side-hustle” is an unfair advantage.”

 

Gary Ross, Founder and CEO, Blip Insurance 

 

 

“As someone who works with entrepreneurs, I believe side hustles can be one of the most effective training grounds for founder development. It forces you to test your skills on two fronts, sharpening your judgement.

“But the benefits are not automatic. The biggest risks I have seen are burnout and being under-resourced. When a side hustle feels personal, founders often treat it more casually, potentially overlooking the financial and operational risk they would never ignore in their primary business.

“This is exactly why at blip, we created a Five Step Financial Guide for side hustlers. With the right structure, a side hustle can become a genuine accelerator for founder growth. It gives people the space to experiment and build confidence without risking their main venture. Far from being a distraction, a well-managed side hustle can improve skill sets and ultimately make them more capable when leading businesses.”

 

Lee Holmes, CEO of INFINOX

 

 

“People often talk about side-hustles as if they’re a guilty pleasure, as if they are something you should sneak around with after hours. I’ve never subscribed to that. In my experience, side-hustles usually come from one of two places: passion or spotting a gap in a market. And frankly, I want people in my company who have that sort of spark. It shows spirit, creativity, curiosity, a willingness to engage with the world and try to make it better. That’s exactly the mindset that drives innovation.

“Of course, there’s always the argument that a side-hustle might dilute focus. But good leaders don’t fear that, they channel it. If someone has the energy and drive to build something on the side, then as a CEO my job is to harness that attitude for the benefit of their current role. A person who’s learning, experimenting and growing outside the office tends to bring more to the table inside it.

“And if, one day, their side-hustle becomes so successful that they leave to grow it full-time? Good for them. The world needs more people building things, creating value and challenging the status quo – that’s how resilient economies are built. There’s no downside to having alumni who go on to launch great companies.

“So yes, I think side-hustles help founder development, and talent development more broadly. They keep you stimulated, they keep you sharp, and they remind you why you got into business in the first place. As long as the day job is done well, I’ll always back people who back themselves.”