Founders500

The Psychology of a Successful Entrepreneur

Tue, May 26 · 12:00 PM BST

·

Online

Online

Date: May 26th 2026 – 12 noon – 1PM UK Time
Format: Online via Zoom

### Event Overview

Not everyone can attend our in-person events. This online Lunch & Learn is designed for those who want practical, high-impact insight in a focused, accessible format.
In this session, Willem explores what truly drives entrepreneurial success, not tactics, not theory, but the psychology behind how successful entrepreneurs think, decide, and act when certainty disappears.
This is not about “teaching people to fish.”
It’s about developing fishermen.

Through real-world experience built in high-pressure, unpredictable environments, Willem will introduce a practical operating framework called The Entrepreneurial Thinking Compass — a tool designed to help leaders and professionals function effectively when strategy and playbooks fall behind reality.

## What You’ll Gain

By attending this session, participants will:

• Understand how successful entrepreneurs make decisions under uncertainty
• Learn how to operate when clarity is missing but responsibility remains
• Develop tools to overcome fear, rejection, and demotivation
• Gain insight into choosing the right co-founder or business partner
• Recognize common entrepreneurial traps — including “buying the bus” too early
• Strengthen resilience and adaptability in fast-changing environments
• Apply entrepreneurial thinking inside established organisations

This session is relevant whether you are starting a business, leading a team, navigating career transitions, or building something new inside an existing organisation.

## Why Willem?

Willem’s work is not built on theory.
It is proven in environments where certainty is absent and failure carries real consequences.
He has worked in some of the most unpredictable conditions imaginable, helping individuals with little more than determination learn how to think, decide, and act their way forward. In those environments, entrepreneurial thinking is not a concept, it is a necessity.
If these tools work where there are no safety nets, limited resources, and constant uncertainty, they work even more powerfully inside organisations with talent, structure, and scale.
This is what makes Willem different.
His frameworks are field-tested under pressure, not designed for classrooms or slide decks.

## About Willem

Willem is the Startup Coach of the Year 2025 and Startup Mentor of the Year 2023, and has been recognised by Thinkers360 as a Top 50 Global Thought Leader in Lean Startup in 2022, 2023 and 2025, as well as in Careers in 2025. He brings over 25 years of entrepreneurial experience across manufacturing, online and creative industries. His work centres on a critical challenge facing modern organisations: how people think and act when certainty is gone and responsibility remains. Willem holds a Master’s degree from the University of Liverpool in the United Kingdom and is based in Johannesburg, South Africa, working with clients worldwide.

## Who Should Attend

• Founders and aspiring entrepreneurs
• Leaders navigating change
• Professionals seeking greater resilience
• Teams operating in fast-moving environments
• Anyone interested in developing practical entrepreneurial capability

### Join Us Online in May

Step away from your desk. Bring your lunch.
Learn how to navigate uncertainty with clarity and confidence.

Tickets here - https://founders500.com/session/the-psychology-of-a-successful-entrepreneur/

The People Problems No Founder Sees Coming

Tue, Jun 16 · 6:15 PM BST

The Warwick, 1-3 Warwick St, Soho, London, W1B 5LR, GB

Date: Tuesday 16th June, 6:15-9 PM UK Time
Location: 1 Warwick by Maslow’s

Sign up for this event here! Please note that clicking attend on Meetup will not give you the correct QR code to enter this event. Please sign up for your Universe ticket using the correct link.

### Most founders think scaling is a hiring problem. It’s not, it’s a people problem.

Building and scaling a startup is hard, but turning it into an organisation is where things really start to break.
At around 15 to 30 people, what once felt easy suddenly becomes more complex. Communication slows down, expectations become unclear, performance becomes inconsistent, and founders often find themselves stuck in the middle of everything. Many assume it’s a hiring issue, but in reality it runs deeper.

In this interactive session, we’ll unpack the people challenges founders don’t see coming as they scale, brought to life through real stories, honest reflections, and practical insight from working inside growing organisations.
Through a conversational, interview-style format, we’ll explore five of the most common areas where founders underinvest early, and the impact this has as their companies grow.

This isn’t a lecture. It’s an opportunity to step back, reflect on your own business, learn from others in the room, and leave with practical ideas you can apply immediately, whether you are just starting to build a team or already navigating the pressures of growth.

## About the Speakers:

Katherine Ray
Katherine works with founders and senior leaders to identify what actually needs to change in their leadership and people approach before it becomes costly as they scale.
With over 20 years’ experience across early-stage, scaling businesses and large global organisations, she brings a broad and grounded perspective on how people and leadership challenges show up at different stages of growth.
As an executive leadership coach, Katherine focuses on helping leaders build the clarity, capability, and confidence needed to lead effectively as their organisations evolve, while enabling teams to perform during periods of growth, change, and increasing complexity.

Kuldish Sibia
Kuldish is a fractional People leader and founder of Scaling People Solutions, with over 20 years of experience across global organisations, scale-ups, and high-growth environments.
He specialises in helping businesses put the right people foundations in place before growth exposes the cracks. From performance challenges to complex people issues, Kuldish brings a practical, no-nonsense perspective on what happens when early decisions start to catch up, and what it takes to fix them.

## What to Expect on the Night:

Doors open at 6:15 PM with a welcome drink and networking.
Starting at 6:45 PM, this 75-minute
interactive session including Q&A will include:

Real Stories and Insights (Interview Format)
We’ll explore five key people challenges founders face as they scale, including:

• Creating clarity on roles and expectations
• Investing in people management including performance, feedback, and accountability
• Workforce planning, who you hire, when, and why
• How leadership needs to evolve as your company grows
• Building foundations before tools

Each theme will be brought to life through real examples and honest reflections from working with scaling businesses.

Founder-to-Founder Discussion
You’ll have the opportunity to reflect on one of the five key challenges that resonates most with you or is most relevant to your business right now.
Through guided prompts, you’ll explore:

• What’s currently feeling difficult in your organisation
• How this challenge is showing up as you scale
• What you might need to do differently

Q&A
A chance to ask questions and explore specific challenges you’re facing.

Community and Connection
From 8:00 PM, connect with fellow founders, operators, and builders in a relaxed setting designed for meaningful conversation.

You’ll also have the opportunity to speak with Katherine and Kuldish one-to-one about any specific people or organisational challenges you’re currently navigating.

Doors close at 9:00 PM.

## Who Should Attend:

• Founders and co-founders building and scaling a team
• Leaders in growing companies where things are starting to feel more complex than they should
• Anyone hiring, managing people, and noticing that what worked early on is no longer working

This session is particularly relevant for companies moving beyond the early stage, around 10 to 50 plus people, where people challenges become more visible and more impactful.

Sign up for this event here! Please note that clicking attend on Meetup will not give you the correct QR code to enter this event. Please sign up for your Universe ticket using the correct link.