25 Nov What Happens When the Hustle Slows Down?

At Innovation City, we talk to founders every day who are in different stages of the build. Some are sprinting. Some are scaling. Some are exiting. And all of them eventually hit the same moment: “Okay… but what do I do with my life and my money after this?”

To explore that transition, we sat down with Josh Kaplan, Wealth Manager at Investec W&I, who works with founders navigating exactly this shift. We wanted to understand what really changes once the adrenaline eases off, and what’s worth thinking about long before the LinkedIn exit post goes live.

Welcome to the “New Unknown”

Josh explained that founders are often well-prepared for chaos but far less prepared for the calm that follows it. After years in survival mode, fast decisions, pressure, constant motion, the sudden quiet can feel disorienting.

The inbox slows.
The calendar opens up.
The business stops consuming every corner of your brain.

And that’s when a new kind of uncertainty emerges: How do you protect what you’ve built without creating a new source of stress?

Now You Need Structure (the Good Kind)

From Josh’s experience, many founders underestimate how grounding it is to put a few key financial structures in place. The tools that matter most at this stage aren’t complicated:

• Trusts to organise wealth outside your estate

• Endowments to make inheritance simpler for your family

• Retirement vehicles to secure long-term income

• Offshore investments to diversify in a meaningful way

He noted that these structures function less like financial products and more like stress-reducers –  guardrails that keep your hard-earned assets from becoming another unknown.

Because Markets Can Be Dramatic Too

When we asked Josh about volatility, he pointed back to the market turbulence seen on Liberation Tariff Deadline Day, the kind of behaviour that instantly reminds founders of early-stage chaos.

This is where alternative investments play a role, typically forming about 10%–25% of a portfolio. Structured products and autocalls fall into this category. While they’re not the typical topic of conversation over cortados, they offer something founders value: a degree of built-in protection.

Josh described them as investments designed with safety mechanisms; still able to participate when markets rise, but structured to limit the impact when markets fall. In practical terms, it’s the financial equivalent of climbing with a harness: ambition supported by cushioning.

The Investec Way: People First, Portfolios Second

What stood out most in our conversation was how Josh approaches the process. Rather than starting with spreadsheets or predicted returns, he begins with people; their lives, families, responsibilities, and definitions of prosperity.

The starting questions are simple but revealing:

• What does “enough” look like for you?

• What does prosperity feel like in your actual life?

• Who are you building this for, and what will they need from you in the long run?

From there, Investec W&I draws in tax specialists, fiduciary experts, and investment professionals to design a structure that reflects that individual’s version of a good life. It becomes less about wealth management and more about translating wealth into clarity and calm.

A Real Founder Example

Josh shared the experience of working with a founder who had recently exited and wanted a financial plan that felt stable and straightforward rather than overwhelming. The resulting approach combined a retirement annuity overcontribution, a bottom-drawer trust, and a long-term plan that balanced cost, security, and simplicity.

The aim wasn’t complexity; it was clarity.

The Chapter After the Grind

This is the part of the founder journey that rarely gets airtime: when the noise settles, when the team can run without you, when your life starts to have actual breathing room.

That’s when proper planning becomes essential.

And if there was one consistent thread in our conversation with Josh, it’s this: wealth planning isn’t about becoming richer; it’s about becoming calmer.

If you’re entering that stage, or even starting to think about it, Josh Kaplan and the Investec W&I team are approachable people to speak to. They work with founders every day, and their focus is on helping you move from hustle mode into a life that finally has room for more than the build.