Life After the Exit: Investing, Energy & Saying No | Simon Rolland

Since exiting my companies just over a year ago, life has taken some interesting turns. Initially, I felt guilty for not being busy and found myself doing 20 meetings a week, burning myself out for no payment. I've since learned the importance of saying no and managing my energy – if meetings drain rather than energise me, they're probably not right.

After the April 2023 exit, I spent time in Europe, studied at IMD Business School in Switzerland, and did some skiing in Verbier. The past year has involved reinventing myself mentally several times, testing different waters until finding my rhythm.

One unexpected challenge was missing having a salary. Despite the exit payout, I disliked living off investment income or eating into capital. This prompted me to shift from purely capital growth investments to incorporating more cash flow-oriented businesses.

I've recently purchased a manufacturing business with family members and bought a business-to-business finance company that's perfectly aligned with my expertise. The latter gives me a manageable team of three people (after previously managing 50), good systems, and strong cash flow while still offering growth potential.

My biggest learning came from a failed investment where a seemingly solid business with smart people collapsed – teaching me to be very careful about who runs businesses with my money. I'm now focused on energy management, problem-solving (which I believe is the most critical skill for founders), and backing local New Zealand businesses.

Looking ahead, I'm balancing my portfolio between ventures with 10x potential and stable cash-flowing assets, while being much more selective with my time and investments.