What does it really take to build a successful business? And how do you know when to keep going, change direction or walk away?

In this episode of Look At You Now, Craig sits down with Andy Evans, serial entrepreneur, investor and mentor, who has built and sold three businesses, invested in over 20 companies and spent decades exploring the opportunities created by new technology.

Andy's entrepreneurial journey began at just 15 years old, selling concert tickets to friends before eventually organising coach trips to major concerts. That early experience sparked a curiosity for business that would go on to shape his life.

From launching digital media businesses in the early days of the internet to starting a podcast production company in 2005, Andy shares what he's learnt about spotting opportunities, trusting his intuition and understanding why being first doesn't always mean being successful.

But this conversation goes beyond business.

We explore why focus is so difficult to maintain, how to recognise your own strengths and weaknesses, the importance of surrounding yourself with the right people and why learning from mistakes can be more valuable than getting everything right the first time.

In this episode, we explore:

• How Andy went from selling concert tickets at 15 to building and selling three businesses
• Why being ahead of your time isn't always an advantage
• How curiosity and intuition help us recognise opportunities
• The importance of timing when making big decisions
• Why focusing on too many things can stop us from making meaningful progress
• How to identify your strengths and surround yourself with people who complement them
• What Andy learnt from his first business exit and how it changed his approach
• Why relationships, integrity and genuine connections matter
• How mentors and other founders can help us understand our own challenges
• The importance of continuous learning and staying curious
• Why building something valuable matters more than chasing an exit
• How a simple walk and conversation can help us think more clearly

Some key takeaways:

Being first doesn't always mean winning. Andy learnt that having the right idea is only part of the equation. Timing matters just as much.

You don't have to be good at everything. Understanding your strengths and weaknesses allows you to find people who bring something different to the table.

Focus means knowing what not to do. Progress doesn't come from having the longest to-do list. It comes from recognising which things genuinely matter and giving them your attention.

Mistakes become valuable when you learn from them. Andy explains how the challenges of selling his first business helped him approach his next business differently.

Relationships are built through genuine interest in people. Staying connected, helping others and building trust can create opportunities that you could never have planned for.

Whether you're starting a business, navigating a career change or simply trying to understand how to make better decisions, this conversation offers a different perspective on success, personal growth and the value of learning through experience.

Connect with Andy Evans:

Find Andy on LinkedIn by searching Digital Andy.

About Look At You Now

Look At You Now is a podcast about understanding ourselves through the experiences, perspectives and lessons of others.

Through honest conversations, we explore how people think, make decisions, overcome challenges and learn from life, with the hope of making those lessons useful in our own lives.

Understand yourself. Change how you live.

If you enjoyed this conversation, follow Look At You Now on Spotify, Apple Podcasts or YouTube, and share the episode with someone who might find it valuable.