$40 Million by 40! (Simon Rolland)

Simon Rolland, fresh off his third business exit with Aurora Financial, shares insights into his journey of building and selling businesses. His audacious goal of $40 million net worth by age 40 stems from a methodical approach to business: start, scale, and sell.

Currently managing a private family office with about 25% of assets invested across six (soon seven) companies, Simon's focus is clear - he builds businesses with exit plans in mind. Aurora Financial, his largest venture to date, exemplifies this strategy. The company, known for its fleet of branded Teslas in Christchurch, was deliberately structured for sale from day one.

Simon emphasises the importance of building sustainable businesses that can operate independently of their founders. He distinguishes between true business owners and the self-employed, noting that many confuse the two. His investment criteria prioritise commercially-minded founders over specific business models.

Looking forward, Simon maintains his ambitious targets but stays grounded, acknowledging that while $40M by 40 would be nice, it's not his primary driver. He's now focusing on his family office operations, continuing to invest in and scale businesses while maintaining a balanced approach to wealth creation.

His experience has taught him valuable lessons about timing, market cycles, and the importance of building businesses that create genuine enterprise value rather than just personal income streams.