How do you build sustainable healthy habits when overhauling your lifestyle?
Don't try to cut everything at once; introduce changes one at a time (e.g., stop smoking, then cut coffee, then reduce drinking) so the habit becomes sustainable rather than an all-or-nothing experiment.
How should a startup founder respond when they don't know the answer to something?
Say 'I'm not sure' rather than bluffing — it signals confidence rather than weakness and should be followed by a plan to find the answer; investors and team members who react badly to that phrase are not the right people to have around you.
What should founders/creatives focus on instead of just trying to 'sell' their work?
Focus on genuinely getting better at your craft/skill rather than just trying to sell or hustle it, since being truly excellent is what leads to the big opportunities (large record deals, big exits).
How should you think about past projects that didn't hit the 'big' outcome you wanted?
Reframe the full context of what was achieved (e.g., screening a self-made film in a major cinema, charting music on every continent) as a genuine success rather than labeling the project a failure just because it didn't reach the very top outcome.
How do you decide which creative pursuit to focus on when you're good at many things?
Identify what every option has in common rather than treating them as separate paths: for Simons it's always working closely with other people, and always being a form of problem-solving (getting an idea from the brain into the world), which lets him move fluidly between songwriting, running a label, and building a tech company.
Should a musician think of themselves as an entrepreneur?
Every musician is effectively running a small business, even at the smallest club show there can be roughly 27 different roles (merch, sound, lighting, promoter, agent, manager) they coordinate with, so it helps to consciously own that entrepreneurial role rather than deny it.