Nick Holzherr has already built and exited once, then chose to start again. After appearing on The Apprentice in 2012, he built Whisk, a food AI company later acquired by Samsung, spent six years inside a global product environment, then stepped away to build from scratch again.

His latest company, GitLaw, is an AI legal platform for founders, backed by a $3 million pre-seed round. What makes this conversation interesting is where he has chosen to build next. Legal services are still slow, expensive, and badly matched to the way modern businesses actually operate. Nick is building directly into that gap, with a clear view on how AI will change the way legal work gets done.

In this episode, we get into what building with AI actually looks like, what changes after an exit, and how to operate in sectors where the rules are still catching up with the tools.

What we cover

1️⃣ Where AI changes legal work first

Nick explains why the real pressure is not on good lawyers, but on slow processes, bloated workflows, and work that should already be more efficient.

2️⃣ The hiring mistakes that cost companies most

Weak hires kill momentum fast. This part gets into the interview process, case studies, and short trials Nick uses to protect quality.

3️⃣ Why standard legal work should not cost what it does

For many founder needs, the answer is not bespoke drafting. It is solid market-standard documents, structured properly and delivered faster.

4️⃣ Pricing from the buyer’s side

Nick talks about what changed when he stopped pricing from his own comfort zone and started understanding what enterprise buyers already expected to pay.

5️⃣ How distributed teams stay sharp

Writing things down, documenting decisions, and keeping clean specs made it possible to scale across time zones without creating confusion.

Chapters

00:00 Introduction to Nick Holzherr

02:08 Turning The Apprentice into startup leverage

06:59 Early funding, pivots, and finding traction with Whisk

10:47 When big tech came calling and choosing Samsung

13:52 Hiring 100 people in nine months

20:35 How to actually run a remote, async global team

24:50 Leaving Samsung and working out what to do next

28:24 Spotting the AI moment and the first ideas for GitLaw

31:48 AI, job displacement, and who gets hit first

37:39 Why legal costs are broken for founders and SMEs

42:55 Backlash, cease and desist letters, and staying resilient

48:25 Building GitLaw differently with AI-native workflows

51:19 Building from Birmingham and hiring globally

55:19 Quickfire: best decision, hiring mistakes, Sam Altman, books, and sacrifice

Get more founder interviews and practical business lessons in the Millennial Masters newsletter at MillennialMasters.net

Send this to anyone trying to handle legal work without burning cash ⚖️

Josh Payne is the founder and CEO of Coframe. He never took a traditional route. Straight out of Stanford, he went into building, turning a pandemic project into a telemedicine company later acquired by Tata Group.

He then co-founded Autograph and helped scale it during the NFT wave to unicorn level with major investors behind it. What stands out is the kind of problems he moves towards. He built GPT-Migrate, one of the first autonomous AI agents for code transformation, and now runs Coframe, an AI optimisation platform used by companies like OpenAI and The Economist to drive measurable revenue gains.

In this episode, we get into what building with AI looks like when the hype fades, where human judgement still beats autonomy, and how to stay focused when the tools keep changing faster than the market can absorb them.

What we cover

1️⃣ Where AI still falls short

Josh talks about the gap between what people expect from autonomous agents and what models can actually do reliably today.

2️⃣ Why human judgement still matters

The strongest outcomes still come from pairing people with AI properly rather than letting the model run unchecked.

3️⃣ Building momentum without waiting for a grand plan

Coframe grew out of small experiments, fast feedback, and following what users actually responded to.

4️⃣ Focus as an edge in noisy markets

Josh explains why going deeper on one customer outcome matters more than chasing every new model, feature, or hype cycle.

5️⃣ Products that improve through use

This part gets into what makes AI genuinely valuable inside a product and why self-improving systems will matter more than surface-level AI features.

Chapters

00:00 Introduction to Josh Payne

02:35 Skipping the safe 9–5 path

04:23 From jazz gigs to building products

07:01 AxisBell: launching a COVID telemedicine startup

09:45 How one client became a buyer

12:50 What selling your first startup actually feels like

14:48 Autograph, NFTs, and the celebrity-backed rocket ship

20:06 What LA taught Josh that Silicon Valley could not

23:23 NFT hangover: bubbles, greed, and timing your exit

27:16 GPT-Migrate and the spark that became Coframe

31:33 Coframe’s model: real AI value vs AI theatre

34:46 Why human plus AI beats AI alone

38:31 AI’s limits today and near-term risks

42:21 Alignment, jailbreaks, and who really controls AGI

45:53 Which models Josh trusts and why

49:50 The thread connecting healthtech, NFTs, and AI

52:42 Sleeping in his car, grit, and what sacrifice means

56:22 Hiring people who run as hard as you

58:51 Why Coframe is in-person and how Josh is changing as a CEO

01:00:26 What Josh would teach his younger founder self

01:01:19 Life, startups, and the bicycle race analogy

01:02:42 Trade-offs, money, and staying aligned with your purpose

01:05:46 Cold swims, float tanks, fasting, and staying sharp

Get more founder interviews and practical business lessons in the Millennial Masters newsletter at MillennialMasters.net

Pass this on to the smartest builder you know 🔁

Carly Meyers has one of those stories that sounds unlikely until you hear it properly. She started on London’s West End, performing in shows like Wicked and sharing the stage with Monty Python at the O2. Then one bad landing during an audition ended that chapter overnight.

What followed was a full reset through waitressing, sewing custom clothes, working at the Apple Store, building a network marketing business, burning out, and starting again. Eventually, she found her way into tech, automation, and AI. Today, Carly runs Made for More, a lean AI-powered business, coaches entrepreneurs, and works with a small human team supported by AI agents.

In this episode, we get into reinvention, resilience, and what building looks like when AI becomes part of the way the business runs. Carly shares how curiosity changes the way founders use new tools, where automation actually helps, and how to build lean without letting the pace of it all take over.

What we cover

1️⃣ The mindset that makes AI useful

Carly explains why curiosity beats resistance, and why the best founders are the ones willing to test, learn, and keep asking better questions.

2️⃣ Running lean with a small team and AI support

This part gets into how she uses AI across finance, legal, marketing, and operations without turning the business into a mess.

3️⃣ Fixing the system before adding more tools

Automation only helps when the foundations are clean. Broken workflows just get amplified faster.

4️⃣ What failure taught her about resilience

Carly talks about rejection, setbacks, and why her bounce-back rate matters more than trying to avoid failure altogether.

5️⃣ Protecting time as the business grows

The episode also gets into designing your days properly, keeping space for learning and creativity, and building in a way that still feels sustainable.

Chapters

00:00 Introduction to Carly Meyers

02:35 From West End to AI: reinventing after injury

05:39 Finding purpose after losing identity

08:21 Network marketing lessons: building resilience and grit

13:58 From burnout to breakthrough: fitness, focus, and mindset

16:05 First steps with AI: content creation and curiosity

18:25 How AI helped build a business without a big team

21:48 The “I wonder” mindset

22:45 Building custom GPTs: your first virtual team

28:07 AI agents trained on Hormozi and Martell

30:52 Claude vs ChatGPT

33:52 Creating AI financial advisers and legal agents

36:33 Virtual assistants, automation, and n8n

45:43 AI agents vs employees

50:00 Inside Carly’s AI audit framework

56:01 Why clean data is the real AI advantage

59:16 How to fail fast and build resilience

01:02:49 Protecting time and mental freedom

01:06:39 The lesson she’d tell her younger self

01:08:00 What ambition and kindness mean for her kids

Get more founder interviews and practical business lessons in the Millennial Masters newsletter at MillennialMasters.net

Send this to someone trying to build lean without burning out ⚙️

Everyone wants to build fast, but Harry Sanders had to build just to survive.

At 17, he faced something no one should: sleeping under a bridge in Melbourne with nothing but a backpack and a laptop. A social worker gave him a plan. He took it, learned fast, and built StudioHawk to one of the world’s top SEO agencies from scratch.

Today, Harry runs a 140-person team across three continents, hiring what he calls “wholesome nerds”: people with low ego and high potential. His rule is simple: ideas don’t build companies. Discipline does.

This episode’s about patience, pressure, and the kind of mindset it takes to build when the world writes you off.

🔗 Find Harry on LinkedIn, Instagram & YouTube

Takeaways from Harry’s episode

1️⃣ Sit on every new idea for a week

Founders love ideas, but too many ideas kill execution. Harry writes them down, waits seven days, then only shares the ones that still matter. Discipline protects your team from chaos.

2️⃣ Hire for hunger, not CVs

Harry doesn’t chase perfect CVs. He hires “wholesome nerds” — people with curiosity, humility, and something to prove. Skill can be taught, but attitude can’t.

3️⃣ Simplicity scales faster than scope

StudioHawk only does SEO. No ads. No websites. That focus turned a solo hustle into a global agency. Clarity beats diversification every time.

4️⃣ If you can’t leave, you don’t own it

Harry learned the hard way that being across everything makes you the bottleneck. The business only became scalable when it stopped depending on him.

5️⃣ Confidence is built, not gifted

He wasn’t born confident, but he earned it through small reps and public failures. Every time you step outside your comfort zone, you strengthen the muscle that makes the next leap easier.

Also mentioned in this episode:

Hawk Academy — Harry’s free SEO training platform

How to see the fan-out queries ChatGPT runs — The video on Harry’s Insta

In this episode we cover:

00:00 Introduction to Harry Sanders

02:25 How Harry went from homeless teen to founder

07:48 How StudioHawk grew into a $20M global SEO agency

11:02 How to hire ‘wholesome nerds’ and spot raw talent early

13:12 Why your early team can hold back your next stage of growth

21:52 Why focus scales faster than ideas

26:49 How to shift from survival mode to CEO mindset

32:53 Why Harry gives back to fight youth homelessness

35:46 Will AI kill SEO? Here’s what’s really happening

42:00 How new brands can get seen in AI search

50:12 Why most founders aren’t ready for SEO yet

54:25 How education became StudioHawk’s growth engine

57:05 What it really costs to build something that lasts

James Fleming had everything you’re meant to want: a senior exec role in oil and gas, the house in Dubai, the pool, the salary, the status. But he realised he wasn’t happy.

Then life stepped in. A corporate reshuffle made him redundant, and overnight his three-year plan to start a business became a three-month deadline to survive.

He and his wife launched The Power Within from their living room, selling watches to fund marketing and building their first leadership programme from scratch.

Today, James trains leaders around the world on what he calls motivational intelligence: the mindset shift that turns self-doubt into self-leadership. It’s practical, human, and built on hard-earned lessons.

We talk about what it really takes to rebuild after losing everything, why confidence comes before competence, how to balance empathy with standards, and why your vision is the anchor for every decision you make.

If you’ve ever wondered whether mindset really makes the difference, this episode will leave you with no doubt.

🔗 Find James on LinkedIn

Takeaways from James’ episode

1️⃣ Before you can have, you must become

James doesn’t believe in “fake it till you make it.” He believes in acting like the person you’re trying to grow into. Show up like an owner before you technically are one. Your behaviour sets your ceiling.

2️⃣ Confidence comes before competence

People wait until they “know enough” to lead. That’s backwards. You only get competent by doing reps, getting it wrong, adjusting and going again. If you’re waiting to feel ready, you’ll never ship.

3️⃣ Excuses are just mislabelled priorities

“I don’t have time” usually means “it’s not important enough to me.” James draws a hard line between a reason and an excuse. A reason comes with learning and ownership. An excuse comes with nothing.

4️⃣ Vision is not optional

Every client he coaches has to answer one question: in 12 months, if everything went right, what would you be telling a friend in the pub about your business? If you can’t picture it, you can’t build it. Your brain can’t execute on a blank page.

5️⃣ Success is not money

James had the cash, title and status. He still felt empty. His definition now: aligned expectations and reality. When what you’re doing matches who you believe you are, that’s when you get peace. Everything else is noise.

📘 Check out James Fleming’s book

* You Can Have Success or You Can Have Excuses — You Cannot Have Both

In this episode we cover:

00:00 Introduction to James Fleming

02:11 Walking away from comfort (and a big salary)

07:50 Redundant on Friday, founder on Monday

12:34 The first two years nearly broke him

18:58 How James actually coaches leaders

24:19 Why mindset beats tactics

29:03 Act like the person you’re trying to become

34:04 The four-day work week experiment (what really happened)

38:17 Success vs excuses

40:51 Getting called out by your own team

48:18 Building a company (and a marriage) together

52:09 Your vision is the operating system

Most people complain about the office, but Joe Averill built a business by rethinking it.

He launched Level in the middle of a so-called office apocalypse: no co-founder, no funding and a young family depending on him. But Joe saw what others didn’t: companies still want space, they just don’t want old-school leases, hidden costs or landlord games.

Before Level, Joe cut his teeth in Manchester’s tech scene, learned sales the hard way and built a network the old-fashioned way: by showing up. Today, Level is one of the fastest-growing tenant-only advisory firms in the UK, built on one principle: trust scales faster than hype.

If you’re an entrepreneur debating your next office move (or scaling without a safety net) this is your episode.

🔗 Find Joe on LinkedIn

Takeaways from Joe’s episode

1️⃣ Self-belief is a business strategy

Joe launched Level with no co-founder, no funding and no safety net. The first resource he built with was conviction.

2️⃣ Sales is still the engine

Joe grew Level through pipeline and process. Prospecting, follow-up and conversion are still what move revenue.

3️⃣ Networks compound when you give first

Joe built relationships by adding value, making introductions and understanding people, not by pitching them.

4️⃣ The office isn’t dead, lazy thinking is

Hybrid changed how teams use space, not whether they need it. Smart founders now prioritise flexibility, amenities and cost transparency over long leases.

5️⃣ Confidence follows action

Joe still gets nervous before panels and big rooms. He just does it anyway. Reps build confidence, not theory.

In this episode we cover:

00:00 Introduction to Joe Averill

02:03 The “offices are dead” bet

05:52 What tech taught him about pipeline, product & pitch

10:08 Networking that adds value (not noise)

12:50 Personal brand, minus the cringe

17:33 Shy to on-stage: reps over fear

20:55 Tenant-side only: flipping the model

23:24 The office brief most founders miss

30:22 When revenue tanks: steady hands, smart moves

33:12 Mentors, models & the lessons to ignore

35:37 From notebooks to playbooks: systems > heroics

39:00 Scaling with fractionals: CFOs, COOs & more

42:23 Founder energy: avoiding burnout (for real)

45:38 Activity breeds confidence: getting unstuck

47:31 The best risk he ever took

People talk about connection, but this week’s Millennial Master builds it. Lara Varjabedian is the founder of UBQT, a platform reconnecting people in real life.

Before launching her startup, Lara spent 13 years inside the global corporate machine. Then she moved into the startup world, helping VC-backed companies scale at speed... until she realised she was ready to build something of her own.

She bootstrapped UBQT from Dubai during lockdown, turned an MVP into a real product, and raised a $750k pre-seed round to go global. Today, she’s building a social platform with no feeds, no likes and no ego, just real-world connection.

This conversation is about what it actually takes to build when there’s no safety net, and how to stay sane while doing it.

Takeaways from Lara’s episode

1️⃣ Momentum beats perfection

You don’t need a full product to start. Lara bootstrapped UBQT with a simple MVP and used momentum as a growth strategy long before investment arrived.

2️⃣ Fundraising is not validation

Money in the bank doesn’t mean product-market fit. Lara raised $750k pre-seed but kept building like she had nothing, staying close to users and pushing for traction over hype.

3️⃣ Build for behaviour, not vanity metrics

UBQT has no likes and no feeds on purpose. Lara designed the product around real-world behaviour: catching up, travelling and meeting face-to-face.

4️⃣ Female founders face a bias tax, do it anyway

Lara shares how women are judged harder and pitch with more self-doubt. Her antidote: evidence, conviction and relentless resilience.

5️⃣ Your runway mindset matters more than your runway

The highs and lows don’t slow down, they compress. Lara protects her mental energy and reframes setbacks as signals instead of failures.

In this episode we cover:

00:00 Intro to Lara Varjabedian

02:17 From corporate to startups

05:08 Making the leap to entrepreneurship

07:29 The birth of UBQT

09:42 Designing for real-life connection

12:42 Building communities across borders

21:15 Navigating Dubai’s startup ecosystem

24:26 Why Dubai is a global launchpad

28:25 Lessons from bootstrapping to pre-seed

33:19 The emotional rollercoaster of startups

38:22 Coping with stress and execution pressure

Most people chase money. Jason Graystone chases freedom.

He’s not your typical wealth guru. Jason quit a safe career when his first child was born, blew £40k learning the hard way in the markets, and then built digital assets that went on to make millions. His philosophy is simple: buy time, not things.

In this episode, Jason shares why financial freedom starts with mental freedom, what losing big early really teaches you, and how to reverse engineer your life so you’re not stuck living by someone else’s rules.

🔗 Find Jason on LinkedIn, Instagram or YouTube

Takeaways from Jason’s episode

1️⃣ Freedom starts in your head

Money doesn’t solve everything if your mindset is trapped. Jason argues financial freedom only comes after mental freedom, knowing who you are and what you want.

2️⃣ Losing money is tuition

Jason blew £40k in the markets early on, but he didn’t treat it as failure. He calls it an education that taught him discipline, patience, and resilience.

3️⃣ Give it all away

His multi-millionYouTube funnel was built on one principle: share everything for free. The more value you give, the more people trust you, and the more they’ll pay to work with you.

4️⃣ Repeat yourself without fear

Jason’s message hasn’t changed in nine years. Repetition builds trust, and entrepreneurs shouldn’t be afraid of sounding boring. Consistency is what compounds.

5️⃣ Buy time, not things

Financial freedom isn’t about Lambos or Rolexes. It’s having enough assets to cover your lifestyle and free up your calendar so you can choose how to spend your days.

📖 Jason’s book recommendations

The Values Factor by Dr. John Demartini — Jason credits this book with helping him align his choices to his real purpose. It’s about understanding your core values so you can build a life and business that feel true to who you are. Dr. Demartini also wrote the foreword to Jason’s own book.

Always Free by Jason Graystone — Jason’s blueprint for financial, mental, and time freedom. He shares the lessons that took him from trading losses and early business struggles to building digital assets and investments that let him design life on his own terms.

In this episode we cover:

00:00 Intro to Jason Graystone

02:29 From struggles to security: Jason’s early life

07:45 Taking the leap: quitting for freedom

12:07 Building wealth: lessons from early ventures

14:56 The power of content creation

19:47 You never really lose, it just changes form

22:46 Mental freedom: defining true wealth

27:23 Reverse engineering your life: finding fulfilment

33:09 Understanding financial freedom

37:39 The importance of resilience and authenticity

43:03 Changing your environment for growth

47:45 Defining true freedom

51:59 Sacrifices on the journey to freedom

55:56 Influential books and philosophies

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