📺 Watch now on Substack or YouTube | 🎧 Listen on Spotify or Apple Podcasts

— Millennial Masters is sponsored by Jolt ⚡️ Reliable hosting for modern builders

Simon Penson went from journalist to exited entrepreneur, building one of the UK’s fastest-growing digital agencies and selling it in a £20m deal to one of the world’s biggest advertising groups.

In this episode, he opens up about the hidden costs of scaling, from early hires who become blockers, to the harsh reality of earn-outs that can make or break your outcome.

Now through Scaled, Simon helps B2B companies and scale-ups navigate the same challenges, bringing the perspective of someone who has lived the highs and lows of growth.

This one’s all about what really happens when growth hurts, and what it takes to get to the other side.

🔗 Find Simon on LinkedIn

Takeaways from Simon’s episode

1️⃣ Early hires won’t always scale with you

The people who got you off the ground can become blockers later. Spot it early, have a plan, and know when to move them into the right role… or off the bus.

2️⃣ Culture isn’t a nice-to-have, it’s survival

Scaling breaks things fast. Without clear values and accountability, you’ll carry people you shouldn’t. The hard calls on culture usually come too late.

3️⃣ Earn-outs are a trap if you’re not prepared

Don’t separate price from terms. Structure interim payments, get specialist advice, and back yourself only if you control the levers that drive growth.

4️⃣ Know your growth plateaus

Businesses don’t scale in straight lines. Each stage brings a ceiling, breaking through means building specialist “generals” in ops, sales, finance, and strategy.

5️⃣ Bootstrap vs raise is a life decision

Don’t raise money for the sake of it. Sometimes a bootstrapped £20m exit is better than chasing £100m with heavy dilution. Define what success looks like for you.

📖 Simon’s book recommendations

On Strategy by Boston Consulting Group — Simon credits this old-school classic with shaping how he thought about scaling in a structured way. It gave him a framework for understanding growth stages and building with intent, lessons he still draws on today even if the examples feel dated.

In this episode we cover:

00:00 Introduction to Simon Penson

02:03 From Journalism to Digital Entrepreneurship

05:00 Building and Scaling Zazzle

08:01 Navigating Growth Challenges

10:06 The Importance of Culture in Business

12:14 Merging for Success

15:33 Understanding Earn-Outs

18:46 Key Metrics for Business Valuation

21:05 Coaching and Investing in Startups

23:06 AI's Impact on Marketing

26:47 Rapid Fire Insights

Get full access to Millennial Masters at millennialmasters.net/subscribe