The Entrepreneur Experiment

Dan Kiely built one of Ireland’s great entrepreneurial success stories.
Alongside Linda Green Kiely, he transformed Voxpro from a small Cork business into a global company working with some of the biggest technology companies in the world.
But what did that level of success actually cost?
In one of the most open conversations we have had on The Entrepreneur Experiment, Dan talks about the sacrifices required to build a company of that scale, the obsession that drove him, his relationship with Linda, cracking America, building powerful networks and eventually selling Voxpro.
Then came the part nobody prepares founders for.
Dan remembers looking at €45 million in his bank account after the deal and realising he had never felt more miserable.
We talk about identity after an exit, addiction, giving up alcohol, learning to be present, men's mental health, his relationship with success and why he is now going back to the classroom to become a better coach and listener.
Dan also explains what he looks for when investing through MASV, why Irish founders need to think globally much earlier and why relationships remain one of the greatest competitive advantages in business.
This is a conversation about building a huge company.
But more importantly, it is about what happens to the person who builds it.
Show Notes
In this episode we discuss:
00:00 Dan and Linda's extraordinary partnership
00:42 Why Linda was the original venture capitalist
04:30 Building a company valued at €150 million
05:42 What success actually cost Dan
10:00 The hidden pressure behind public success
15:00 Why Dan fought for the idea of “operational beauty”
20:40 Our growing addiction to Reels
25:30 AI will either serve you or you will serve AI
35:45 Why Irish founders need to go where their market is
40:30 Why your network is everything
46:10 Why Voxpro was “50% business and 50% show business”
50:08 Ireland's complicated relationship with failure
52:40 How America changed Dan's mindset
59:30 Addiction, ambition and giving up alcohol
01:01:13 Becoming more present and getting to know himself
01:06:15 Why every entrepreneur needs to understand their exit
01:10:50 Life immediately after selling Voxpro
01:11:27 “I had €45 million in my bank account and I've never been so miserable in my life”
01:15:00 Finding a new identity and creating MASV
01:19:10 Men's mental health and helping other founders
01:20:00 Why Dan has gone back to education
01:25:00 Linda's next chapter and using fashion to create impact
Guest resources
Dan Kiely on LinkedIn
MASV

Michelle Kennedy was told to build another dating app.
She knew dating. She had worked at Badoo and Bumble. It was the obvious move.
Instead, she built Peanut.
Michelle created Peanut after becoming a mother and experiencing first hand how isolating that transition could be. What began as the product she wished existed has grown into a global community connecting women through motherhood, fertility, menopause and some of the most important stages of their lives.
But the journey started unusually.
Michelle raised investment before she had a product or a team. At that point, she essentially had herself, an idea and a deck.
She then made another unconventional decision. Rather than slowly expanding from London across the UK, she went directly after the US market, launching into cities including New York, San Francisco and Los Angeles.
In this episode, we unpack how she did it.
Michelle explains why she deliberately targeted America, what she would do differently if she were raising money today, and why taking institutional investment so early created lessons she only understood later.
We also explore one of the most important but least discussed advantages in business: your network.
Michelle openly admits that she spent much of her early career without understanding networking at all. She explains how she eventually realised that relationships were driving opportunities all around her, and how founders can build a network intentionally rather than simply collecting contacts.
We discuss the difficult balance between founder instinct and data, why listening to every piece of advice can damage a company, and how Michelle learned to distinguish useful feedback from pressure to follow trends.
Michelle also explains why she believes great consumer founders need taste, why experimentation is fundamental to building products, and why a catastrophically bad experiment can sometimes teach you far more than a small improvement.
We explore Peanut's mission beyond technology and why Michelle believes real world human connection will become even more valuable as AI becomes more powerful.
Michelle also shares Peanut's work around matrescence, the biological, psychological and emotional transition into motherhood, and the company's wider mission to make women's experiences better understood.
And finally, Michelle shares the three qualities she believes have been most important to her success as an entrepreneur: grit, passion and team.
In this episode
• Why Michelle built Peanut after becoming a mother
• Why people encouraged her to build another dating app instead
• Raising VC funding before having a product or team
• Why Peanut attacked the US market from the beginning
• What Michelle would change about her fundraising strategy today
• The funding challenges still facing female founders
• Why founders need to filter advice
• The danger of following trends instead of your customer
• How Michelle learned the importance of building a network
• Why relationships can become a hidden advantage in business
• Combining founder instinct with data
• Why great consumer founders need taste
• How to run experiments that actually teach you something
• Why a dramatically unsuccessful experiment can still be valuable
• AI and the increasing importance of real human connection
• Peanut's work around matrescence
• The Village Fund and helping mothers connect in real life
• Michelle's three ingredients for entrepreneurial success: grit, passion and team
About Michelle Kennedy
Michelle Kennedy is the founder and CEO of Peanut, a platform designed to connect women through different stages of life including fertility, pregnancy, motherhood and menopause.
Before founding Peanut, Michelle worked in the dating industry at Badoo and was involved in the early development of Bumble.
She launched Peanut in 2017 after experiencing first hand the need for better connection and community following the birth of her first child.
Learn more about Michelle and Peanut
Peanut
https://www.peanut-app.io/
Download Peanut through the Apple App Store or Google Play.
The Village Fund
https://www.peanut-app.io/village-fund
Peanut and Coterie have created a six figure fund designed to help mothers turn online connections into real world meetups and communities.
Book recommended by Michelle
Grit: The Power of Passion and Perseverance by Angela Duckworth
https://www.angeladuckworth.com/grit/
Michelle describes Grit as a phenomenal book and recommends it for founders. The book explores Angela Duckworth's research into why sustained passion and perseverance can matter more to long-term achievement than talent alone.

Mark Hughes started Solidroad in Dublin in 2023 with his co founder Patrick Finlay.

There was just one problem.

They did not actually know what they were going to build.

Three years later, Solidroad has gone through Y Combinator, built offices in Dublin and San Francisco, landed major enterprise customers and raised a $25 million Series A.

In this episode of The Entrepreneur Experiment, Mark breaks down exactly how it happened.

We go inside the early search for product market fit, how they got their first customers, founder led sales, getting into Y Combinator after multiple attempts, moving his life to San Francisco and the extraordinary speed at which Silicon Valley operates.

Mark also tells the story of meeting First Round Capital on a Saturday, meeting the partnership on Sunday and effectively having the investment agreed by Monday.

We then get into AI.

Mark explains how AI has completely changed the way he works as a CEO, why he believes repetitive work is most at risk, why customer support will remain a combination of humans and AI, and how he is effectively building an AI powered operating system around his company.

Finally, we talk about the biggest mistake he has made building Solidroad and the lesson he would give his younger founder self:

Move faster.

A fascinating conversation about ambition, fundraising, sales, AI, Silicon Valley and what it really takes to build a venture scale company.
—-

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CHAPTERS

00:00 Meet Mark Hughes and Solidroad

01:52 From Dublin startup to a $25M Series A

03:09 Why Mark became a second time founder

04:30 Starting a company without knowing what to build

06:01 How they searched for the right problem

07:49 The moment they realised they had something

09:09 Funding the company before Y Combinator

11:39 Revenue as the North Star

15:01 Why timing matters in startups

17:00 How Solidroad found its first customers

19:37 Mark's founder led sales playbook

24:28 Why moving to San Francisco changed everything

24:59 What Y Combinator actually does

26:33 Inside a typical week at YC

28:31 Getting into YC after multiple attempts

31:24 The personal cost of moving to San Francisco

34:38 What happens after Y Combinator

36:22 Inside YC Demo Day

37:27 Meeting First Round Capital

38:50 Saturday meeting, Monday money

39:53 Building a $6.5M seed round

42:10 Landing major enterprise customers

42:49 Why money raised is the wrong success metric

43:10 Why Solidroad raised again

44:56 Will AI take our jobs?

46:30 Why customer service will remain human

48:56 The jobs most exposed to AI

49:40 How an AI powered CEO works

52:42 Has Claude overtaken ChatGPT?

54:04 Raising the $25M Series A

59:05 Mark's advice for founders raising money

1:00:41 Dublin versus San Francisco

1:02:52 What comes next for Solidroad

1:03:59 Mark's biggest mistake

1:07:02 Quick fire

1:10:22 Why face to face sales will win in an AI world

1:13:37 The advice Mark wishes he had earlier

1:14:08 Speed is everything

Sara Davies built the business that changed her life.

Then she had to fight to save it.

In this episode of The Entrepreneur Experiment, Sara tells the story of what happened when Crafter’s Companion, the company she founded from her bedroom, ran into serious trouble and ultimately entered administration.

She talks candidly about buying the business back, the brutal 18 months that followed, and what it feels like when the company that has defined so much of your life suddenly becomes the source of enormous pressure.

This is not simply a story about business recovery.

We talk about the decisions and warning signs that founders can miss when a company is growing, including the uncomfortable reality of doing around £20 million in revenue while struggling for cash.

Sara also opens up about stepping away from Dragons’ Den, the pressure of trying to be a founder, investor, television personality and mother at the same time, and reaching the point where she knew something had to change.

We explore ADHD, hyperfocus, motherhood, guilt, resilience, investing and the psychology that has allowed Sara to keep moving forward through some of the most difficult periods of her career.

In this conversation:

• What really happened inside Crafter’s Companion

• How a business can generate huge revenue and still run into cash problems

• Why Sara decided to buy her company back

• The toughest 18 months of her business career

• The founder mistakes she can now see more clearly

• Why she stepped back from Dragons’ Den

• The pressure of combining ambition, business and family

• Sara’s experience of ADHD and hyperfocus

• How she evaluates entrepreneurs and investments

• What difficult periods have taught her about resilience

This is a very different side of Sara Davies.

It is a conversation about what happens when success becomes complicated, when the business you built needs saving, and how you rebuild both the company and the founder behind it.

The Entrepreneur Experiment is about one central idea:

Build a better founder, not just a better business.

—-

Our Sponsors:

Nostra: https://bit.ly/nostra26
Azure Communications: https://bit.ly/azure26

Follow The Entrepreneur Experiment:

Instagram: https://www.instagram.com/entrepreneurexperiment/
TikTok: https://www.tiktok.com/@entrepreneurexperiment
Podcast: https://www.mrgaryfox.com/podcast

James Haskell has spent most of his life performing under pressure.

He won 77 caps for England, toured with the British & Irish Lions, played professional rugby around the world and then had to figure out who he was when the game stopped.

Today, James is an entrepreneur, broadcaster, author, DJ and co-host of The Good, The Bad & The Rugby. He’s also building Blackeye Spirits alongside Mike Tindall and Alex Payne.

But this isn’t really an episode about rugby.

It’s about building a better founder, not just a better business.

We talk about why self-awareness may be the ultimate competitive advantage, how elite sport teaches you to handle brutal feedback, why ambitious people struggle to recognise when enough is enough, and how James rebuilt his identity after rugby.

We also get into focus, saying no, buying back your time, therapy, accountability, personal branding, choosing business opportunities, the creator economy, why information is becoming free and why implementation is becoming more valuable.

James is candid, funny and completely unfiltered throughout.

If you’re ambitious, stretched across too many things, or trying to work out what success actually means to you, there’s a lot in this one.

In This Episode

We cover:

What professional sport teaches you about business

Why “you can lie to everyone else, but you can’t lie to yourself”

How to receive feedback without letting your ego get in the way

The four things James believes you can actually control

Why achievement can leave high performers permanently unfulfilled

The difference between chasing outcomes and mastering process

What Eddie Jones taught him about excellence

Reinventing yourself when your first career ends

Why James started preparing for life after rugby at 20

Learning to say no to opportunities

How he decides which businesses and projects deserve his time

Why he refuses most equity-only deals

Authenticity, personal branding and protecting audience trust

Why information is becoming free but implementation will remain valuable

Therapy, mental performance and changing your emotional state

His approach to focus, batching and avoiding distraction

Why even a former professional athlete pays someone to keep him accountable

Buying back your time

Defining how much money is actually “enough”

Turning The Good, The Bad & The Rugby from a podcast into a media business

Why modern podcasts need to think beyond audio

Building Blackeye Spirits and the mission behind the Blackeye Rugby Fund

Links & Resources

James Haskell: official site covering his rugby, books, music and other projects. James Haskell official website (https://jameshaskell.com/)

The Good, The Bad & The Rugby: James hosts alongside Mike Tindall and Alex Payne; the show describes itself as the world’s biggest rugby podcast. The Good, The Bad & The Rugby (https://goodbadrugby.com/)

Blackeye Spirits: James, Mike Tindall and Alex Payne’s spirits business. The brand says its Rugby Fund aims to eventually invest £1 million annually supporting injured players, research, risk reduction and recovery.
Blackeye Spirits (https://blackeyespirits.com/

James’s books: What A Flanker, Ruck Me and Approach (With)out Caution are all featured on his official site.