AI has made it easier to build, test and automate an idea. Building a business is still building a business. In this episode I'm joined by Christopher Carter for an honest conversation about what building and leading a company really asks of you.

Chris has been building companies since the 1980s. He has succeeded, failed, lost a company and started again more than once. We get into the difference between the freedom people imagine and the responsibility that it carries, the year that makes or breaks most people, and what happened when one customer came to represent 80 per cent of his revenue.

We have both lived through a period of transition like this one, in a different tech boom, and we compare what it taught us. A fair amount of the conversation is about where AI genuinely changes things for founders and where it changes nothing at all. Chris describes the relationship between people and AI as an infinity loop, and is clear about the one thing no founder should hand over.

We also talk about identity. When anyone can produce anything, judgement and knowing what you bring become the differentiators. More options do not produce more clarity, usually the opposite. Knowing what you stand for is one thing. Staying clear enough to act on it is another.

This episode covers what founders need behind the scenes, which people rarely discuss openly.

Timestamps
00:00 Christopher's journey as a serial entrepreneur
01:30 What people misunderstand about entrepreneurship
03:25 The laptop-on-the-beach image versus the reality
06:50 Why the first year can be the hardest
09:45 What AI now makes possible for entrepreneurs
13:00 Why building an app isn't building a business
15:30 Does the AI wave resemble the e-commerce boom?
18:00 The human-AI infinity loop
19:00 Critical thinking, verification and education
21:00 What failure teaches that a book or AI cannot
23:00 Losing a company after relying on one customer
25:00 What founders should never outsource to AI
26:30 Identity, ethics and judgement in a faster world
31:00 Why experience is an advantage in the AI era
33:20 The support entrepreneurs need behind the scenes
36:30 Health, pressure and personal capacity
37:30 Questions to consider before starting a business
40:00 Speed, learning and knowing when to change direction
41:30 What Christopher trusts now
42:30 Christopher's book recommendation
43:25 Where to follow Christopher's work

About Christopher Carter
Christopher Carter is a serial entrepreneur, technologist and author, and Chairman and CEO of Approyo, a global SAP-focused technology company. His career in technology goes back to 1984. He speaks around the world and is a minority owner of Carrick Rangers.

Book mentioned

Coming of Age: How Technology and Entrepreneurship Are Changing the Face of MENA by Noor Sweid.

Connect with Christopher

LinkedIn, and christophermcarter.com.

About Katherine

I'm Katherine Ashmore, The Unblur® Coach. I work one to one with founders, senior leaders and experienced professionals whose thinking has been blurred by pressure, complexity or transition. The blur is what makes it hard to think clearly, decide confidently or trust your own judgement. Unblur® is the work of getting that back and more.

If this episode hit home and you would like to talk about coaching, I offer a free consultation with no obligation and no sales pitch. I'm also available for speaking and as a podcast guest.

katherineashmore.com

LinkedIn

contact@katherineashmore.com

The Unblur® Podcast, formerly The Mindset Exchange.

Disclaimer
https://www.katherineashmore.com/katherine-ashmore-disclaimer/

Produced and created by Katherine Ashmore. Recorded remotely. © Katherine Ashmore 2026. All rights reserved.