Kevin O'Leary Shares Surprising Advice for New Entrepreneurs: 'Be an Apprentice for 24 Months'

Starting a new business venture can feel like diving into the deep end. With countless guides and gurus offering advice, it's easy to get lost in the noise. But what if the secret to success wasn't about immediate leaps, but rather a strategic step back?

Kevin O'Leary, the sharp-tongued investor known for his candid critiques on Dragons' Den and Shark Tank, has recently unveiled a piece of counsel that might surprise you. Far from advocating for instant entrepreneurial dives, O'Leary suggests a foundational period of learning that could redefine your journey: becoming an apprentice for two years.

O'Leary, often called 'Mr. Wonderful,' recently appeared on the Diary of a CEO podcast, sharing frank advice for new entrepreneurs. From the 41:30 mark, O'Leary presented a clear strategy for young founders: start by apprenticing in an industry you care about, accept initial setbacks, and learn the unstated principles of self-assurance and readiness.

Learn by Doing: Two Years as an Apprentice

Instead of hurrying to launch a startup, O'Leary suggests starting with two years of practical experience in an industry you care about. He clarified: 'Go work for 24 months in a sector you love, that you're passionate about. Even if they don't pay you, go in there and be an apprentice.'

According to O'Leary, this in-depth training helps founders understand 'how all the cogs work' within a business, from daily tasks to crucial decision-making. He also notes that being part of the internal team can bring valuable acknowledgement: 'It could also lead to recognition from someone at the company that could be useful down the line.'

After building this base, O'Leary advises starting your first business with limited funds—' with a $10,000 (£7463.15) loan from friends and family.' He highlights that entering the startup world with genuine industry experience provides a significant advantage: 'Start your business with the baseline knowledge of your industry.'

Embrace Early Setbacks: The Power of 'Burning Years'

O'Leary is direct about the path of an entrepreneur: your first business likely won't make it. 'The first one will probably fail,' he cautions. However, O'Leary sees this not as a defeat, but as essential for development. He stressed, 'You need to burn a few years failing, and that matters.'

He urges new founders to begin this journey in their early twenties, a period when failure carries fewer consequences and offers greater lessons.

Project Confidence: More Than Just the Pitch

A strong business background isn't the only thing that matters, according to O'Leary; how entrepreneurs carry themselves is equally vital. He emphasised the importance of an 'aura of confidence,' noting that body language and appearance can be crucial even before a person speaks.

'It's in the way you're standing. It's in the way you're dressed... If you don't have it, you're going to fail,' O'Leary quoted, as reported by Business Insider. He encourages founders to perfect their nonverbal signals, as he believes confidence builds credibility well before any presentations or financial details are shared.

Why O'Leary's Approach Resonates

O'Leary's counsel cuts through popular startup myths: success doesn't happen instantly, status isn't required, and presence counts. Here are the key points:

• Apprenticeship provides a deep understanding of the industry, helping founders navigate markets effectively and avoid serious errors.
• Failing early equips entrepreneurs with valuable lessons, turning setbacks into opportunities for growth and progress.
• Confidence isn't about arrogance; it's an advantage that builds trust and prevents early doubts.

These aren't just theories; they come from O'Leary's own experiences. From SoftKey's rapid expansion to facing failures, he knows the value of practical and confident preparation.

A Clear Guide for Founders

O'Leary's philosophy can be summarised as:

• Work first, launch later. Spend two years gaining hands-on experience to truly understand your industry.
• Embrace failure. Early mistakes are an essential part of genuine learning.
• Carry yourself like a founder. Your posture, clothing, and overall manner all contribute to your presentation.
• Start affordably. A modest loan and market understanding are more effective than ambition without insight.

A Realistic Path to Entrepreneurial Success

For anyone seeking an innovative approach to starting a business, O'Leary's advice offers a blend of realism and hope. His main message is straightforward yet powerful: be prepared, get hands-on experience, and act with purpose. With these elements, even a small business has a genuine chance of success.