Millennial Masters

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 Intro 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

Confidence isn’t free. As Lauren Currie puts it, “as your confidence increases, you will lose people.” She’s built Upfront into a global movement helping thousands of women step onto stages, into boardrooms, and into leadership roles that were never designed for them.

In this episode, Lauren shares the reality of building confidence as a muscle, not a finish line. We explore tall poppy syndrome, the myth of imposter syndrome, and why visibility has financial consequences for founders and leaders.

With six ventures behind her, Lauren has learned how to turn discomfort into growth, and how to keep ambition alive in systems that try to punish it. Her work shows that ambition is not a dirty word, but an engine for change.

🔗 Find Lauren on LinkedIn and Instagram

Takeaways from Lauren’s episode

1️⃣ Confidence is costly

Confidence comes with trade-offs. As Lauren says, the more confident you become, the more some people will push back. Your growth exposes their stagnation. Recognising that this resistance is about them, not you, helps you keep moving forward.

2️⃣ Imposter syndrome is a system, not a flaw

Lauren rejects the idea that imposter syndrome is a personal failing. She sees it as a rational response to being the “only” in the room: the only woman, the only young person, the only outsider. It’s a signal you’re challenging the status quo, not proof you don’t belong.

3️⃣ Ambition isn’t something to apologise for

Ambition in men is celebrated, in women it’s often criticised. Lauren argues that ambition should be embraced as a force for change. You don’t have to dial it down or package it in humility to make others comfortable.

4️⃣ Visibility is financial

Good work doesn’t speak for itself. Leaders who stay invisible risk missing out on promotions, opportunities, and income. Visibility isn’t about ego, but about learning in public and advocating for your work before you feel ready.

5️⃣ Design your trade-offs with intention

Lauren avoids the trap of chasing “work–life balance.” Instead, she makes intentional choices about trade-offs, guided by her values. Whether it’s work on a Saturday or time with family, the decision is conscious, not default.

In this episode we cover:

00:00 Intro to Lauren Currie

02:05 Building confidence as a muscle

04:36 The journey of Upfront

12:29 Entrepreneurial pathways and lessons learned

18:46 Understanding imposter syndrome

24:43 Practical steps to build confidence

27:17 The cost of confidence

29:21 Navigating ambition and gender dynamics

35:08 Embracing life’s seasons

35:57 Intentional living and values

40:33 Effective remote team management

44:28 Visibility and personal branding

48:31 Building confidence and overcoming fear

50:26 Reflections on sacrifice and legacy

Petr Kozyakov didn’t set out to build a crypto company. He set out to solve a problem. After struggling to make a simple cross-border payment, he realised the gap in how money moves, and turned that frustration into Mercuryo, a 300+ person fintech bridging crypto and traditional finance.

He talks candidly about building a culture that survives hypergrowth, learning where not to waste energy, and the habits that keep him grounded as both a founder and a father. This is the human side of fintech leadership, told by someone scaling at global level.

🔗 Find Petr on LinkedIn

Takeaways from Petr’s episode

1️⃣ Energy is better spent building

Petr learned that proving a point or winning an argument drains momentum. Direct that energy into collaboration and creation instead.

2️⃣ Culture can’t be compromised

Even in hypergrowth, Mercuryo cut loose “A-players” who didn’t fit the culture. Skills don’t outweigh behaviour, because misalignment poisons the team.

3️⃣ Growth requires constant adjustment

Every stage of Mercuryo demanded a shift in focus, from landing the first customer, to building new products, to hiring leaders and keeping hundreds of people aligned. What worked at 20 people no longer worked at 300.

4️⃣ Create their own experts

In crypto, there were no ready-made compliance veterans. Petr hired open-minded people from traditional finance and helped them grow into crypto specialists, turning a gap into an edge.

5️⃣ Founders need real recovery

For Petr, daily workouts, strict sleep routines, and quality time with family are non-negotiables. Burnout kills judgement, and no fintech playbook will save you from it.

In this episode we cover:

00:00 Intro to Petr Kozyakov

02:34 The transaction that started a business

04:17 Bridging crypto and fiat: making transactions easy

07:16 The evolution of crypto: from niche to mainstream

09:36 Use cases for crypto: beyond just investment

14:19 Building a team: culture and hiring principles

17:17 Scaling challenges: lessons from growth

23:05 Navigating compliance: the regulatory landscape

28:38 Control, focus and delegation

32:24 Systems to manage remote teams

35:02 Finding balance: personal sacrifices and well-being

43:35 Advice for future founders

Kevin de Patoul walked away from a secure consulting career to build Keyrock, a digital asset firm that’s now raised over $80 million and employs nearly 200 people worldwide. His mission is to create the infrastructure that will power the next generation of financial markets.

In this episode, Kevin breaks down the lessons from scaling a startup at hyper-speed, navigating volatile crypto cycles, and keeping a team aligned while the ground shifts under your feet.

From capital raises and culture challenges to separating hype from true innovation, this is an inside look at what it takes to build in one of the most unpredictable industries in the world.q2

🔗 Find Kevin on LinkedIn

Takeaways from Kevin’s episode

1️⃣ The real prize is infrastructure

Kevin argues that real innovation in crypto isn’t the latest meme coin, but the infrastructure that allows value to move securely and at scale. Founders should focus on solving fundamental problems, not chasing trends.

2️⃣ Growth puts culture under strain

Keyrock jumped from 3 to 160 people in a year. Processes collapsed and culture bent. Only clear values kept things intact.

3️⃣ Crypto is 24/7. You can’t be

The market never switches off. Founders have to. Kevin enforces boundaries and trusts systems to carry the load.

4️⃣ Big raises raise the stakes

Raising $80 million didn’t ease the journey. It made every choice heavier. Kevin stresses discipline and investor alignment over chasing growth at any cost.

5️⃣ Volatility rewards the steady

Most fear chaos. Kevin looks for openings. If you can adapt quickly, stay grounded, and keep delivering value, the market cycles can actually accelerate growth.

In this episode we cover:

00:00 Intro to Kevin de Patoul

01:58 From consulting to crypto: a career shift

04:53 Keyrock: the investment bank for digital assets

07:33 Debunking misconceptions: crypto vs digital assets

10:33 The real innovation of tokenization

13:28 The future of asset ownership

16:16 Disruption or replication in finance

19:02 The future of crypto: accessibility for all

21:45 The long-term viability of crypto

24:04 Lessons from rapid scaling

29:07 Hiring for mindset over skills

34:53 Managing a remote team

40:11 Building team cohesion

41:22 Fundraising lessons

50:20 Balancing work and life

54:17 Sacrifices on the entrepreneurial journey

This week’s Millennial Master is Emma Mills, founder of MiPA.

Emma started out answering calls and managing inboxes. Seventeen years later, she built MiPA into a seven-figure executive assistant business serving more than 500 clients. Along the way, she’s learned how to protect her own time, escape the bottlenecks, and build a culture that scales.

In this episode, Emma shares the systems, mindset shifts, and non-negotiables that help founders focus on the work they actually enjoy. From default diaries and “winning the week” to delegating outcomes instead of tasks, she’s all about reclaiming your calendar and growing without burning out.

🔗 Find Emma on LinkedIn and YouTube

Takeaways from Emma’s episode

1️⃣ Delegate outcomes, not just tasks

An executive assistant isn’t there to tick boxes, they should drive results. Give them ownership of outcomes, whether that’s launching a project, chasing overdue actions, or clearing bottlenecks, and free yourself to focus on high-value work.

2️⃣ Design your default diary

Map out your ideal week in advance and protect it. Emma keeps three days completely meeting-free, with set slots for calls and internal meetings, so she can focus on creative, strategic work that actually moves the business forward.

3️⃣ Your inbox is the best place to start

For most founders, the inbox is a time sink and a window into their priorities. Hand it over early, with a clear system, so someone else can triage, respond, and keep the important things moving while you’re doing higher-value work.

4️⃣ Clarity kills distraction

The biggest “time thief” (no, not social media) is not knowing exactly what you’re trying to achieve. Set quarterly goals, break them down into weekly priorities, and make sure they’re visible to your team so everyone’s aligned.

5️⃣ Protect your energy with boundaries

Emma builds in recharging rituals throughout the day, keeps personal time in her calendar, and routes most requests through her EA. Boundaries are about ensuring the work you do is energising and sustainable.

In this episode we cover:

00:00 Introduction to Emma Mills

01:55 From assistant to entrepreneur

07:24 The importance of delegation

12:33 Mastering time management

18:04 The art of effective delegation

23:36 Learning from delegation mistakes

32:29 Radical honesty & the cost of mistakes

37:27 Hiring: spotting red flags

41:58 AI’s role in business efficiency

46:45 Balancing business & personal life

53:07 Lessons from leadership: insights from Ralph

54:58 Sacrifices for success

01:00:06 Advice to younger self

This week’s Millennial Master is Brad Mac, co-founder of Unreasonable.

Most brands are burning cash on lazy ads and chasing the wrong metrics. Bradley McDonald (aka Brad Mac) thinks it’s time to do the opposite: cut the noise, go deep on what actually moves people, and treat creativity as a profit centre, not a gamble.

He’s scaled Unreasonable into the marketing agency everyone’s watching, proving you can build a brand that lasts and still win on performance.

🔗 Find Brad on LinkedIn

Takeaways from Brad’s episode

1️⃣ Stop wasting your ad budget

Most brands throw 80% of their spend at branded search. Brad calls it a tax for being average. Put your money where it actually grows the business, not where you’re just protecting your logo.

2️⃣ One killer campaign beats a thousand forgettable ones

Forget running endless ads. Brad’s strategy? Run a single, creative-led campaign that earns attention and compounds results over time.

3️⃣ Chase goosebumps, not algorithms

Great content gets remembered and shared. If your ads aren’t sparking a real reaction, you’re just adding to the noise.

4️⃣ Hiring is everything

Brad only brings in “killers”, people who add value from day one. No long interview chains, just proof you can deliver.

5️⃣ Brand is still king

Performance tactics will only get you so far. The brands that last are the ones that stand for something and back it up with bold creative.

📚 Brad’s book recommendations

Ogilvy on Advertising by David Ogilvy — Brad’s go-to classic for anyone serious about brand and creative. He keeps coming back to Ogilvy’s principles on copywriting, positioning, and making ads that actually sell.

Alchemy by Rory Sutherland — This one’s Brad’s cheat code for creative thinking. He loves how Sutherland breaks the rules and shows why the best marketing ideas never come from pure logic.

Deep Work by Cal Newport — Brad rates this as essential reading for founders and creatives. He credits Deep Work with helping him carve out real focus time, even when agency life gets chaotic.

Slow Productivity by Cal Newport — A new favourite, Brad’s been testing out Newport’s approach to getting more done by slowing down, working deeper, and ignoring the usual busywork.

Poor Charlie’s Almanack by Charlie Munger — Brad swears by Munger’s mental models for sharper decision-making. He’s picked up plenty of counterintuitive lessons on how to scale, invest, and stay rational.

In this episode we cover:

00:00 Intro to Brad Mac

02:06 The Unreasonable origin story

08:01 Transitioning to Unreasonable

10:12 The state of performance marketing

13:34 Measuring success in marketing

17:04 Creating lasting brands

23:29 The role of AI in marketing

29:55 The future of growth marketing

33:45 Traditional media’s place in marketing

36:22 Building a brand in the digital age

39:58 Underrated marketing channels

45:55 The power of personal branding

48:14 Growing Unreasonable: Hiring and culture

57:17 Navigating client relationships

01:00:45 Creating a productive work environment

01:02:16 Maintaining sanity in a fast-paced world

01:08:01 Quickfire questions: Insights and advice

Augustin ‘Gus’ van Rijckevorsel has built his career on bold bets and stubborn ambition.

By his 30s, he’d launched seven companies: some collapsed in spectacular fashion, others scaled fast enough to put him on the radar of Europe’s top investors.

Gus is the kind of founder who hacks the system, takes bets most would avoid, and believes the only real risk is standing still.

Now, as CEO at Ultra, he’s aiming to build the “Netflix of gaming” out of Europe.

In this episode, Gus shares the unfiltered reality behind the founder journey.

🔗 Find Gus on LinkedIn and X

Takeaways from Gus’ episode

1️⃣ Vision is a distortion and reality keeps you in business

Founders survive on a healthy dose of delusion, but long-term success demands you confront the facts, not just your ambitions.

2️⃣ If you pay peanuts, you get monkeys

Cut corners on hiring and you’ll regret it. Quality people are the only thing that matters.

3️⃣ Layoffs and failure never get easier, only more public

You’ll go from hero to villain overnight, and sometimes you’ll have to make impossible calls. Learning to live with the emotional fallout is part of the founder’s job description.

4️⃣ Entrepreneurs take bets, business owners play it safe

Real entrepreneurs chase scale and put everything at risk to get there. If you’re clinging to ownership, you’re not growing, you’re just maintaining.

5️⃣ The biggest risk is standing still

Speed is the new survival skill. You don’t have a decade to prove yourself. If you’re not moving fast, you’re moving backwards.

In this episode we cover:

00:00 Intro to Gus van Rijckevorsel

02:10 From success to failure and back again

07:48 Lessons from collapse and comeback

11:15 Mindset, mentors, and surviving setbacks

16:22 How to spot opportunity

25:33 The all-or-nothing founder approach

30:54 Ultra’s “Netflix for gaming” vision

37:38 Beating the gatekeepers

39:55 Scaling, fundraising, and moving fast

44:30 Managing remote teams

46:59 Europe’s next tech wave

51:22 How AI is changing gaming

59:09 Europe’s protectionism as an edge

01:01:29 Lessons for young entrepreneurs

01:05:37 The value of taking bold risks

This week’s Millennial Master is Jordan Stachini, Founder of Co & Co.

Jordan never planned to be an agency boss. She went from flying around the world in high-pressure marketing roles to starting a consultancy that, thanks to her “no BS” style and obsession with results, quickly snowballed into a boutique agency with clients across the globe.

She’s honest about slow, sustainable growth, why she turns down outside investment, and how setting boundaries keeps her business and life in check.

🔗 Find Jordan on LinkedIn

Takeaways from Jordan’s episode

1️⃣ Boundaries are a superpower

Jordan built her agency by being brutally selective about clients, projects, and pace, protecting her team and sanity over chasing revenue at any cost.

2️⃣ “No” beats “yes” for real growth

Turning down rapid scaling and outside investment wasn’t risk-averse, it was strategic. Slow, organic growth led to a more stable, enjoyable business.

3️⃣ Zero-BS marketing wins clients

Jordan’s “no fluff, all results” approach stands out. She’s upfront about what works, what doesn’t, and refuses to deliver anything half-baked, even if it means saying no to more work.

4️⃣ Personal brand > agency brand

Co & Co thrived because Jordan invested in her own voice online, then encouraged her team to do the same. Employee brands are amplifiers, not risks.

5️⃣ Apprenticeships > grads (for her team)

She sparked LinkedIn controversy by refusing to hire grads straight out of uni, opting for apprentices with drive and hands-on mindset. Her stance? Mindset and learning agility beat paper credentials.

In this episode we cover:

00:00 Introduction to Jordan Stachini

02:18 The journey from employee to entrepreneur

07:11 Navigating lockdown: adapting to new realities

13:45 Choosing clients: the importance of fit

18:41 No BS marketing: the philosophy behind Co & Co

27:51 Hiring for mindset: the no graduates stance

33:02 The value of constructive criticism

43:11 Navigating the loneliness of entrepreneurship

51:12 Maintaining routine and productivity

58:04 Sacrifices on the path to success

Andrew Steele is the founder who went from Olympic medal sprints to building startups with nothing but a risk appetite, relentless honesty, and a knack for ignoring the “safe” option.

After a decade chasing medals, he fell into tech with zero business experience, helped turn DNAfit into a global health brand, stuck it out through an IPO, and is now back at it with Stride: a membership for people who want to know what’s really happening inside their bodies before the problems start.

In this episode, Andrew lays out the realities of going from athlete to first-time founder, scaling up on bootstrapped budgets, and learning to handle rejection like a sport.

🔗 Find Andrew on LinkedIn

Takeaways from Andrew’s episode

1️⃣ The real founder traits aren’t on your CV

Andrew credits his Olympic background for his startup resilience, but it’s not just discipline. Traits like a high appetite for risk, comfort with failing in public, and a pinch of “cheekiness” (bending the rules to get results) are what early-stage investors actually look for.

2️⃣ Your next move is rarely by design

Andrew’s whole founder journey started with a single cold email. Forget perfect plans; most breakthroughs happen because you give yourself permission to try and improvise, even when you’re unqualified.

3️⃣ Bootstrapping teaches hard lessons fast

He scaled his first business, DNAfit, to acquisition without raising a penny, learning that bootstrapping means living in survival mode, saying yes to anything that pays, and improvising on a shoestring. Only later, with Stride, did he blend this grit with external funding (but only after hitting millions in revenue).

4️⃣ IPO is a milestone, not the finish line

Going public with Prenetics was surreal, but Andrew admits it’s not some magical exit: operational headaches just get bigger and you’re forced to trade speed for structure. The hustle doesn’t stop when you ring the bell.

5️⃣ You never really “arrive”

Even after an exit and a public listing, Andrew found himself restless. Real fulfilment came from building again — proof that for founders, progress (not arrival) is the real drug.

📚 Andrew’s book recommendation

East of Eden by John Steinbeck — Andrew credits East of Eden for shaping his mindset as both an Olympian and entrepreneur. There’s a powerful idea buried in its pages: don’t wait for someone else to grant you permission. Give yourself the “permission to try,” whether you’re staring down the Olympic track or launching a startup with zero experience. It’s a reminder that progress comes from putting yourself out there, even when you don’t feel fully qualified.

In this episode we cover:

00:00 Introduction to Andrew Steele

02:15 The intersection of sports and entrepreneurship

08:28 The journey from athlete to entrepreneur

14:18 Scaling a startup: challenges and triumphs

18:21 Navigating corporate culture post-acquisition

24:19 Hiring and firing: building a strong team

28:55 The IPO experience and its aftermath

33:14 Building Stride: a new venture in health

39:16 The role of health systems in preventative care

46:01 Navigating the fundraising landscape

53:14 Habits & routines to stay grounded & productive

01:01:08 Reflections on sacrifice and success

Tyler Dunagin never set out to become “the bathtub guy,” but that’s what happens when you turn burnout into a platform business and outpace almost everyone around you.

After growing up in an entrepreneurial family, Tyler hustled his way from odd jobs to flipping houses, only to hit the wall.

He rebooted, switched from working on homes to scaling businesses, and now runs Turnserv, one of the fastest-growing property service companies in America.

His secret is relentless self-development, radical transparency with his team, and a knack for finding opportunity at the edges.

Tyler’s story is about scaling, the reality of letting go, building real systems, and turning obsession into something sustainable.

🔗 Find Tyler on LinkedIn and Instagram

Takeaways from Tyler’s episode

1️⃣ Delegate with intent

Work out exactly what only you can do, and hand off everything else, then let go. This is the only way to break free from founder bottleneck syndrome and actually scale.

2️⃣ Equity drives loyalty:

Give your managers real skin in the game if you want them to act like owners. Equity isn’t just a perk, it’s how you build a leadership team that thinks long term.

3️⃣ Work-life “integration” wins

Scrap the myth of perfect balance. Blend work and family, but set your own rules. Being present, wherever you are, matters more than sticking to anyone else’s schedule.

4️⃣ KPIs prevent burnout

Clear goals for your team = freedom for you. No KPIs? You’ll end up micromanaging. Weekly targets and reports keep you (and them) sane, so you can actually unplug.

5️⃣ Personal brand = talent magnet

Your reputation as a founder is a recruiting tool, whether you like it or not. Put yourself out there to attract ambitious people who share your values.

📚 Tyler’s book recommendations

Deep Work by Cal Newport — Tyler swears by Deep Work for founders who want to escape busywork and get meaningful things done. He credits it with helping him structure his days for real focus and strategic thinking.

Edge Strategy by Alan Lewis and Dan McKone — This is the playbook behind TurnServe’s growth. Tyler recommends Edge Strategy for any founder wanting to spot business opportunities “within arm’s reach” and layer on new revenue streams without reinventing the wheel.

In this episode we cover:

00:00 Intro to Tyler Dunagin

02:22 The relentless entrepreneur: origins and inspirations

08:11 Building Turnserv: the birth of a new venture

16:35 Innovating with Liquid Liner: a patented solution

21:56 Timing is key in raising private equity

27:21 Hiring for success & the art of delegation

32:18 Core values and culture: the heart of team dynamics

39:17 The impact of equity on employee motivation

45:21 The role of personal branding in attracting talent

48:53 Work-life integration, not separation

53:22 Habits to prevent burnout

57:12 Sacrifices made on the entrepreneurial path

01:01:54 Injecting growth into a stagnant business