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Transcript

E13 — The Toughest Boss Ever with Graham Hobson

"He'll be no trouble, but I think he'll really help the company. And when he came in, my overwhelming feeling was he was the toughest boss I ever had in my life."

Graham Hobson’s story of building Photobox might seem stereotypical. A technical founder builds a product he needs himself, overcomes the adversity of the early years, and sells it for a life-changing £400m.

Yet, some parts of his story are anything but stereotypical. First, he advocates for increased taxes on wealthy people like him to create a more just society. As Graham puts it, he didn’t check the rate of capital gains tax when he founded his business1.

Second, six years into the journey, Graham chose not to lead the business as CEO going forward but instead focus on his work as a CTO, working under an external, experienced CEO who turned out to be “the toughest boss” Graham ever had.

Not every founder CEO chooses to hire an experienced scale-up CEO and then stay working with them for nearly a decade, learning what it’s like to be part of a high-performing executive team. Spoiler: it wasn’t easy at all, but it was worth it.

Enjoy the conversation!

Timestamps

(Clickable on YouTube)

00:00 Introduction

01:59 Should We Tax Wealthy People More?

12:53 The Early Days of Photobox

18:18 A Merger with a Competitor

22:11 The Toughest Boss I Ever Had

29:13 Being Part of an Executive Team

30:00 Challenges That Shape Us

35:04 When To Go Fast and When To Go Slow

37:33 Advice To Own Son

41:36 Advice To Other Founder CEOs

46:26 Fresh Eyes Exercise for Leaders

51:02 Final Thoughts

1

It was the same as the top income tax rate, unlike today when it’s still much lower.

Unconditionally Human
Startup CEO Succession
Real stories from founder CEOs who stepped down, professional CEOs who took over from them and VCs who saw the process from the inside.