Invest in Yourself Like a 1000% Asset
The market returns 10%. Your skills return 1000%.
Olly contrasts two investments: putting money into the S&P 500 returns 7-12% on average; investing in yourself — courses, coaches, paid expert conversations — can return literal thousands of percent because a single skill upgrade can unlock a promotion, a side hustle, or a business worth orders of magnitude more than the input cost.
He practices it religiously. £300/session for a Hollywood-script-writer-style coach (referenced via Damian's identical practice). Three paid expert conversations before launching anything new. Buying clothing advice once it became a video-presence problem. The pattern: identify what's holding you back, find the person with the solution, and pay them.
The framework reframes 'self-development spending' from indulgent to mathematically obvious. Even at the noisy end of personal-development markets, the asymmetry of cost-to-payoff makes it the highest-return asset class available to most people.
- The return on a skill upgrade is uncapped; the return on index funds is capped at market beta.
- Pay for expertise that prevents expensive mistakes — it's cheaper than the mistake.
- Skills compound across decades; you use them on every subsequent project.
- Identify what's specifically blocking you, then buy the solution to that block.
- The best investments often look small — £300 conversations, a £500 course, a coach for a quarter.
- Identify the specific bottleneckDon't shop for generic self-development. Name the exact thing holding you back right now: 'I look bad on camera,' 'I can't write persuasive emails,' 'I don't know how to negotiate salary.' Specificity converts spend into ROI.WarningAvoid spraying budget across generic self-help — it doesn't compound.
- Find the person with the solutionSearch for the specialist who teaches exactly that bottleneck — a copywriting coach, a video-presence coach, a salary negotiation coach, a Hollywood script writer for storytelling. Track-record over fame.Pro tipLook for people who teach the meta-skill, not just deliver the service.
- Buy access aggressivelyPay for 1:1 sessions, courses, or three paid expert conversations before any new venture. £300/hour is a rounding error against the months of trial-and-error you skip.Pro tipOlly's pre-launch ritual: pay three experts to tell him what he doesn't know.
- Apply within 7 daysTranslate every paid input into immediate practice. Coaching without application decays fast. Schedule the application before the session, not after.WarningIf you're hoarding courses without doing the work, the spend stops compounding.
- Stack lifelong skills, not one-off contentPrefer skills you'll reuse for decades — copywriting, sales, public speaking, language, design — over situational content. The decade-of-reuse is what makes the ROI 1000%.Pro tipOlly's copywriting investment in his early days has been used 'over and over again for over 10 years.'
- Reinvest gains into the next bottleneckWhen the previous skill upgrade pays off (raise, side income, faster output), redirect a fraction back into the next bottleneck. Compound the practice itself.
Early in his career, Olly took multiple copywriting courses from online specialists. The skill has powered every blog post, email, book, and business he's launched in the decade since.
Damian pays roughly £300/session weekly to a Hollywood-style script writer to study the history of story, the Greeks, Pathos/Logos/Ethos, and to dissect his own scripts. The payoff isn't immediate, but it differentiates him from finance creators who don't invest there.
Once being on camera made wardrobe a real bottleneck, Olly explicitly invested in learning what works visually — discovering pairings like white hoodie with black top — rather than letting the bottleneck persist.
Olly traces it to early in his career when he discovered copywriting courses — a single skill investment he's used daily for 10+ years across blogs, books, emails, and businesses. The compounding from one well-chosen learning purchase shaped how he allocates capital today.
He contrasts it with his 20s habit of optimising fund expense ratios. The same money spent on a copywriting course produced 100x more value over the decade than the saved-fee differential ever could.