Jack Rogers is a serial founder with deep experience in the B2C space - alongside that he's a legend. A wonderfully real, reflective, and often self-deprecating guy who has been through a lot of hardships and laughs about them. His current startup is called Picnic which is helping people 'reimagine the camera roll', and they have only just started to taste product market fit, 5 years in....

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In this very real conversation, Jack and I break down...

📖 Episode Chapters:

00:00 - Intro

02:49 - Tinder Banter Fb Page

04:00 - Hard Things In Consumer Apps

11:43 - TikTok & Our Evolution

23:19 - Ambition Changing Over Time

36:44 - Raising 4 Seed Rounds

39:59 - Keeping Companies Alive

42:49 - Different Leadership Styles

51:52 - Screening for high integrity

55:31 - Bumble's Brand & Culture

01:02:25 - How Much Time On Brand?

01:04:06 - Connecting To 'The Problem'

01:09:57 - Unique Founder Characteristics

01:19:38 - Cancer, Break Up, Failure

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Why 93% of Entrepreneurs Fail At Content Creation | Dan Murray-Serter

Mastering Leadership: Growing Teams & Growing Yourself | James Grant

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🙋‍♂️ WHO AM I?

If we haven’t met before - Hey 👋 I’m AJ, a serial entrepreneur and community expert who believes that company building should be viewed more through the lens of relationship building.

Through my videos here on this channel, my podcast and my writing on Linkedin, I share stories of successful entrepreneurs and evidence-based strategies and tools to help you create the most sustainable and fulfilling business - giving you a life of freedom!

Kay Munday is Google's expert communication coach. She works with large corporates as well as startup founders to help them connect with themselves, which she says is the key to becoming a great speaker

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In this very energetic conversation, Kay and I break down...

📖 Episode Chapters:

00:00 - Intro

02:02 - Names (Kay & Bear)

07:39 - Not fitting in

10:25 - How to find our essence

15:50 - AJ as a case study

20:54 - Timeline therapy

23:45 - Finding the golden thread

26:30 - Crafting your story

28:35 - Your story breakdown

32:41 - Youtube's ABCDs

38:36 - Example Story

43:16 - Simon Sinek (+ so what?)

44:15 - Stories as medicine

48:40 - Labels

55:41 - Where are you judging yourself?

🍿 WATCH NEXT (Youtube)

Why 93% of Entrepreneurs Fail At Content Creation | Dan Murray-Serter

Mastering Leadership: Growing Teams & Growing Yourself | James Grant

👉 Follow me on Linkedin

🙋‍♂️ WHO AM I?

If we haven’t met before - Hey 👋 I’m AJ, a serial entrepreneur and community expert who believes that company building should be viewed more through the lens of relationship building.

Through my videos here on this channel, my podcast and my writing on Linkedin, I share stories of successful entrepreneurs and evidence-based strategies and tools to help you create the most sustainable and fulfilling business - giving you a life of freedom!

Jamie Mitchell was the MD of Innocent Drinks, Tom Dixon (designer furniture), and now he's a serial Non-Executive Director and Board Chairman.

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Jamie and I met when I advised him on his community of entrepreneurs (called All Together) which was started during covid, connecting volunteer advisors with startup founders.

This was a brilliant conversation about...

📖 Episode Chapters

00:00 - intro

05:09 - ADHD

24:12 - Great board meetings

28:30 - When should we have a board?

31:00 - Who should we have on our board?

35:00 - What problems do boards tackle?

41:00 - How to know when the meeting is going well

44:23 - CEO mistakes with their board

49:00 - CEO : Chairman Relationship

51:18 - When should the board fire you?

55:51 - How to nurture board relationships

57:49 - All Together (community)

01:03:49 - Asking for help

01:08:00 - Do world changers love themselves?

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The Hardest Part Of Scaling: What You Can't Delegate | Hannah Feldman

Shocking Stories From A Successful Startup Founder | Graham Hobson

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🙋‍♂️ WHO AM I?

If we haven’t met before - Hey 👋 I’m AJ, a serial entrepreneur and community expert who believes that company building should be viewed more through the lens of relationship building.

Through my videos here on this channel, my podcast and my writing on Linkedin, I share stories of successful entrepreneurs and evidence-based strategies and tools to help you create the most sustainable and fulfilling business - giving you a life of freedom!

Hannah Feldman scaled her company, Kidadl, from 12 to 450 people in two years. In this podcast interview she shares the hard truths of scaling, and the life of a full time entrepreneur and parent.

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Hannah and I have been good friends for years (she was even the catalyst to me proposing to my fiancé - which we speak about at the end) so this is as honest a conversation between entrepreneurs as it gets.

📖 Video Chapters

00:00 - Intro

01:28 - 4 Year Rollercoaster

10:48 - Scale Up Lessons

13:11 - Impactful Processes

19:08 - Measuring Quality : Quantity

21:32 - Culture With Global Freelancers

25:55 - Growing Pains

29:59 - What you can't delegate

34:11 - Interview Qs

37:32 - Juggling parenthood & startups

40:39 - How to keep going

44:49 - Where did you learn resilience?

47:54 - Unlocking fulfilment

51:12- Mental models for home and work

55:15 - Roles split at home

58:23 - What characteristic are you most proud of?

01:00:10 - How Hannah changed my life

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Hard Startup Truths; Funding, Team Design, Skills | James Routledge

Shazam Founder Interview; Secrets of Luck, Persistence & Success

👉 Follow me on Linkedin

🙋‍♂️ WHO AM I?

If we haven’t met before - Hey 👋 I’m AJ, a serial entrepreneur and community expert who believes that company building should be viewed more through the lens of relationship building.

Through my videos here on this channel, my podcast and my writing on Linkedin, I share stories of successful entrepreneurs and evidence-based strategies and tools to help you create the most sustainable and fulfilling business - giving you a life of freedom!

Stu MacDonald has built the world's tastiest peanut butter. From auto-immune disease, to accounting, a trip to Argentina, scrappy beginnings and then 8 years of grind to build ManiLife to what is it today.

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Stu has been one of the most supportive people on my content journey and his generosity, openness and wisdom shines through in this interview where we cover...

📖 Episode Chapters:

00:00 - Intro

00:53 - Wilson's Disease (The 'Fuck You' Driver)

05:16 - Psychosis, Mania, Depression

10:42 - Who Is Stu?

11:40 - Why Are People So Important?

13:38 - Edu, The Supplier

16:51 - Love As A Currency

23:00 - Listing With Holland & Barrett

25:39 - One Favour A Day

27:46 - Balancing Ambition And A Family

32:29 - Doing Things That Don't Scale

41:56 - Interviewing For Care

44:16 - Trickle Down Attention To The Team

45:35 - Balancing Accountability & Care

47:52 - Long Run vs Short Run

52:50 - How To Get Out Of The Way

54:47 - What's Unique About You As A CEO

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The Human Side Of Startup Leadership | Margot De Broglie

From Vision to Action: Olio’s Bold Goals & Cofounder Dynamics | Saasha Celestial-One

👉 Follow me on Linkedin

🙋‍♂️ WHO AM I?

If we haven’t met before - Hey 👋 I’m AJ, a serial entrepreneur and community expert who believes that company building should be viewed more through the lens of relationship building.

Through my videos here on this channel, my podcast and my writing on Linkedin, I share stories of successful entrepreneurs and evidence-based strategies and tools to help you create the most sustainable and fulfilling business - giving you a life of freedom!

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👉 Subscribe on Youtube to be first to learn from world class, inspiring entrepreneurs

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Margot De Broglie founded Juno, a free app for women and non-binary people to help them become more financially literate. Margot is a very honest and passionate entrepreneur who, in this podcast, shares her relationship with key investors, advisors and her sibling cofounder relationship as well as her relationship with herself.

This is the best summary of the human side of startup leadership I've ever seen.

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Margot and I have been good friends for years so this is as honest a conversation between entrepreneurs as it gets. We deep dive into...

📖 Episode Chapters

00:00 - Intro

02:57 - Sibling Cofounder Relationship

09:30 - Encouraging Employees To Push Back

12:21 - When To Systemise Your Management

16:17 - The Impact of Advisors

25:04 - Vulnerable Investor Relationships

29:20 - Leaning Into Inexperience & Imposter Syndrome

32:45 - Masculine & Feminine Leadership

43:10 - How To Bring Play Into Work

47:18 - Story Of A Human Moment

49:42 - Founders Never Get Positive Feedback

51:32 - How Is Your Mental Health?

56:51 - Founders Are More Polyamorous

01:01:09 - What existential crisis are you going through?

01:10:29 - Who are you outside of work?

🍿 WATCH NEXT (Youtube)

Hard Startups Truths; Funding, Team Design, Skills | James Routledge

Why 93% of Entrepreneurs Fail At Content Creation | Dan Murray-Serter

👉 Follow me on Linkedin

🙋‍♂️ WHO AM I?

If we haven’t met before - Hey 👋 I’m AJ, a serial entrepreneur and community expert who believes that company building should be viewed more through the lens of relationship building.

Through my podcast, my videos on Youtube and my writing on Linkedin, I share stories of successful entrepreneurs and evidence-based strategies and tools to help you create the most sustainable and fulfilling business - giving you a life of freedom!

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👉 Subscribe on Youtube to be first to learn from world class, inspiring entrepreneurs

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Graham Hobson built Photobox for 17 years before selling it for €400m. In this deep dive interview he shares crazy stories from that journey and frameworks for building companies.

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Graham and I have been friends for years so this was a deeply personal and educational dive into:

📖 Episode Chapters

00:00 - Trailer

00:46 - How To Deal With Code Reds

08:19 - Intro

15:03 - Characteristics Of An Entrepreneur

18:48 - Talk To Other Founders

28:57 - Culture Transplant

41:54 - What Leader Would You Have Liked To Be?

45:30 - How Much Can We Push Employees? (& Incentives)

51:52 - Near Death Experiences

57:00 - Was It Worth It?

01:02:00 - Impact On Family Life

01:06:04 - Lessons That Apply To Family & Business

🍿 WATCH NEXT (Youtube)

Hard Startups Truths; Funding, Team Design, Skills | James Routledge

Why 93% of Entrepreneurs Fail At Content Creation | Dan Murray-Serter

👉 Follow me on Linkedin

🙋‍♂️ WHO AM I?

If we haven’t met before - Hey 👋 I’m AJ, a serial entrepreneur and community expert who believes that company building should be viewed more through the lens of relationship building.

Through my podcast, my videos on Youtube and my writing on Linkedin, I share stories of successful entrepreneurs and evidence-based strategies and tools to help you create the most sustainable and fulfilling business - giving you a life of freedom!

- - -

👉 Subscribe on Youtube to be first to learn from world class, inspiring entrepreneurs

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Saasha Celestial-One is the cofounder of a rapidly growing consumer scale-up called Olio (4m users in the UK, 8m users globally).

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Saasha and I have been friends for years so this was a very real and educational deep dive into cofounder relationships, scaling challenges, and juggling personal life struggles with the demands of a scale-up.

📖 Episode Chapters

00:00 - Intro

01:44 - What Does 'Getting Old' Mean To You?

03:28 - How Does That Impact Your Leadership?

06:17- ABF (Always Be Fundraising)

08:54 - Weaving Values Into Everyday Life

15:31 - Top Of Funnel Experiments

17:40 - Impacts on User Experience (UX)

20:40 - Olio's Community

23:52 - How To Test Cofounder Relationships

29:53 - How To Nurture Cofounder Relationships

35:50 - Staying Aligned With Cofounders

42:49 - Company Vision Iteration

49:06 - What Feels Ambitious For Olio?

53:08 - Founder-Led Brand

56:30 - Transparency With The Team

01:00:19 - Managing A Divorce & Running A Startup

01:05:10 - Saasha's Husband Mat

👉 Follow me on Linkedin

🙋‍♂️ WHO AM I?

If we haven’t met before - Hey 👋 I’m AJ, a serial entrepreneur and community expert who believes that company building should be viewed more through the lens of relationship building.

Through my videos here on this channel, my podcast and my writing on Linkedin, I share stories of successful entrepreneurs and evidence-based strategies and tools to help you create the most sustainable and fulfilling business - giving you a life of freedom!

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👉 Subscribe on Youtube to be first to learn from world class, inspiring entrepreneurs

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