Follow me on IG - https://www.instagram.com/heydeanreilly

Book a 15 min Call - https://calendly.com/work-worth-doing/work-worth-doing-airbnb-mentoring

Follow me on IG - https://www.instagram.com/heydeanreilly

Work with Me - https://calendly.com/deanreilly/work-worth-doing-airbnb-mentoring1

Follow Julia on IG 👉 https://www.instagram.com/fightnomadjulia/
Follow me on IG 👉 https://www.instagram.com/heydeanreilly

Work with Me 👉 https://calendly.com/deanreilly/freedom

She got fired, had no backup plan. But then blew up to 300K followers on Instagram.

In this episode of Work Worth Doing, Julia shares her experience of build a life she actually wanted after feeling trapped to her 9-5.

You’ll learn:

- What getting fired taught her about safety
- Why 100K followers left her burnt out and broke
- How she rebuilt from scratch with no niche and no backup plan
- The moment she realised her “freedom” business still felt like a trap
- How slowing down became the only way forward

Grab My 7 Day Email Course to Launch an Airbnb without Owning a Property  👉 https://preview.mailerlite.io/forms/1061723/159242701050479620/share

From $0 to $4M… but Darren Lee didn’t do it by chasing views.

 He built a business that lasts, by learning to play the Infinite Game.

In this episode, we go deep on how he scaled a podcast agency that now makes $4M/year, and why so many founders fail by chasing a game they can’t win.

You’ll learn…

• The mindset shift that saved his business
• Why most people stay broke (even with skills)
• How the podcast became the business
• What the Infinite Game really means, and how to win it
• Why the best founders don’t try to “escape”

Grab My 7 Day Email Course to Launch an Airbnb without Owning a Property  👉 https://preview.mailerlite.io/forms/1061723/159242701050479620/share

A solo update on where I’m at, life, business, mindset, and what's been going on lately:

 → The numbers from my Airbnb + coaching businesses
 → What I’ve learned from shitty hires and messy ops
 → Why I am in Baii

Grab My 7 Day Email Course to Launch an Airbnb without Owning a Property  👉 https://preview.mailerlite.io/forms/1061723/159242701050479620/share

Sol smashed $100K in 100 days. But what makes his story powerful isn’t the revenue, it’s the system that got him there.

In this episode, we unpack the three ingredients that changed everything for him, and the sneaky beliefs that hold most creators back.

You’ll learn…

• Why “views” don’t matter
• How to test your way into a 6-figure offer
• What batch content gets wrong
• How sales is actually about self-worth
• The hidden cost of staying in the 9-5 too long

Instagram:

@sol.hyde

@heydeanreilly

@work.worth.doing.podcast

Newsletter: workworthdoing.transistor.fm

Grab My 7 Day Email Course to Launch an Airbnb without Owning a Property  👉 https://preview.mailerlite.io/forms/1061723/159242701050479620/share

Dan Kelsall is the founder of Offended and one of the most irreverent voices on LinkedIn. But what makes him powerful isn’t the swearing, it’s the clarity behind it.

From getting rejected by clients for being “too much” to building six-figure campaigns for KFC, this episode is a no-bullshit look at what it really takes to stand out.

You’ll learn…
– Why your content feels forced (and how to fix it)
– The real difference between a personal brand and a sellable brand
– Why building a business ≠ posting more
– How to gamify backlash so you stop fearing it
– What makes people actually buy from you

Dan's Linked In
- https://www.linkedin.com/in/dan-kelsall/

Work with Me 1to1
- https://calendly.com/deanreilly/discovery-call-path

Grab My 7 Day Email Course to Launch an Airbnb without Owning a Property  👉 https://preview.mailerlite.io/forms/1061723/159242701050479620/share

Biliana is a sales and marketing strategist for solopreneurs, but what makes her story powerful isn’t the revenue, it’s the clarity behind her process.

From years of helping creators “sell without the sleaze” to building offers that convert without burnout, this episode explores what actually moves the needle.

You’ll learn…
– Why most founders feel awkward about sales (and how to fix it)
– The magnesium vs. sleep analogy (and why your offer isn’t landing)
– Why conviction matters more than confidence
– How to tell if it’s a content problem or a positioning one
– Why authority isn’t built in carousels — it’s built in stories

IG
Biliana IG - @myonlinemarketingcoach
Biliana LinkedIn - https://www.linkedin.com/in/bilianastoyanova/
Me - @heydeanreilly
Pod - @work.worth.doing.x

Grab My 7 Day Email Course to Launch an Airbnb without Owning a Property  👉 https://preview.mailerlite.io/forms/1061723/159242701050479620/share

Aston Haslam is the co-founder of multiple 6 and 7-figure property companies but what makes his story remarkable isn’t the revenue, it’s the mindset that built it.

From earning £20K/year in a corporate job to raising £10 million in private finance by the age of 25, Aston shares the raw, unglamorous truth behind what it actually takes to build freedom, and why most people are chasing the wrong version of it.

This episode is a refreshing gut-check for anyone who’s convinced that success means Lambos, exits, or grindset hacks. Aston breaks it all down with brutal honesty and a grounded, no-fluff perspective.

You’ll learn...

- Why real freedom means getting a haircut at 2pm, not flying private
- How Aston raised £3.6M in funding before the age of 25
- Why simplicity scales better than cleverness
- The #1 mistake people make when trying to escape their 9-5
- Why documenting the boring bits is your unfair content advantage

Instagram
@astonhproperty
@heydeanreilly
@work.worth.doing.x

Grab My 7 Day Email Course to Launch an Airbnb without Owning a Property  👉 https://preview.mailerlite.io/forms/1061723/159242701050479620/share

In this solo episode, I share x3 priceless lessons I’ve learned from backing myself, plus a bonus at the end.

If you’ve ever doubted whether you pull this off, this episode is for you.

📷 Instagram
@heydeanreilly @work.worth.doing.podcast

📰 Newsletter
https://workworthdoing.transistor.fm

Grab My 7 Day Email Course to Launch an Airbnb without Owning a Property  👉 https://preview.mailerlite.io/forms/1061723/159242701050479620/share

Dean shares a solo episode about the lessons learned from a big loss early in his entrepreneurial journey. This candid account provides actionable advice for handling setbacks, staying resilient, and navigating the emotional challenges of business ownership.

You'll learn...

• Why I lost £16,000 ($20k usd)
• What to remember when buying any online course
• How to soften inevitable setbacks
• My biggest realisation from this painful loss

Instagram - @heydeanreilly @work.worth.doing.podcast

Newsletter - workworthdoing.transistor.fm

Learn how I built my Airbnb Business below:

• https://join.thesaco.co.uk?affiliate_code=e019b7

Grab My 7 Day Email Course to Launch an Airbnb without Owning a Property  👉 https://preview.mailerlite.io/forms/1061723/159242701050479620/share

Troy Munson is an ex-enterprise sales executive turned entrepreneur who left the corporate world to build his own businesses. From selling two startups to launching Demo, Troy’s journey is about taking risks, learning from setbacks, and creating a life of purpose.

Troy shares his transition from high-paying sales roles to entrepreneurship, the challenges of building on the side, and the rewards of taking control of his career and life.

You'll learn...

-How to transition from sales to entrepreneurship
- The risks and rewards of starting a business while working full-time
- How to turn your side hustle into a full-time venture
- The importance of resilience and long-term thinking
- Why success looks different for everyone

Instagram - @troy.munson @heydeanreilly @work.worth.doing.podcast
Website - workworthdoing.transistor.fm

Learn how I built my Airbnb Business below:

- https://join.thesaco.co.uk?affiliate_code=e019b7

Timestamps:

00:44 - Troy’s journey from sales to startups
03:30 - Why sales executives earn more than surgeons
07:06 - The hidden dangers of comfort in enterprise sales
09:43 - Why Troy always knew he wanted to be an entrepreneur
12:45 - Building Vocal: From idea to selling the business
18:36 - Dealing with doubts and setbacks as a founder
23:50 - How to start a business discreetly alongside a job
30:02 - Selling Referral: Solving problems with creativity
37:01 - Why success looks different for everyone
43:36 - What motivates Troy to keep building businesses
48:04 - Final thoughts: Taking the leap to build your dream life

Grab My 7 Day Email Course to Launch an Airbnb without Owning a Property  👉 https://preview.mailerlite.io/forms/1061723/159242701050479620/share

Aaron Knightley is a multi-talented entrepreneur, events business owner, investor, podcast host, and content creator with over 400,000 TikTok followers.

Aaron shares his unconventional views on time freedom versus financial freedom, the importance of taking responsibility, and how he helps others transition from a 9-to-5 into their first business. His direct approach and controversial ideas will leave you thinking differently about work, money, and life.

You'll learn...

- Why time freedom matters more than financial freedom
- How to quit a 9-to-5 and start your own business
- Why taking responsibility is key to success
- How to handle financial stress and build wealth
- The power of delayed gratification and consistency

Instagram - @aaronknightley @heydeanreilly @work.worth.doing.podcast
Newsletter - workworthdoing.transistor.fm

Learn how I built my Airbnb Business below:

https://join.thesaco.co.uk?affiliate_code=e019b7

Timestamps:

00:00 - Introduction: Why freedom is better than financial success
03:15 - Aaron’s turning point: Having a child at 20
09:12 - Why most people only act when it’s too late
12:45 - The dangers of dependency on a 9-to-5 income
18:36 - Why money makes you happy and secure
25:28 - Taking ownership of your financial future
31:22 - The importance of discipline and delayed gratification
37:01 - Why most people stay stuck in a job they hate
43:36 - Building a business with minimal resources
52:42 - How Aaron’s program helps people quit their jobs

Grab My 7 Day Email Course to Launch an Airbnb without Owning a Property  👉 https://preview.mailerlite.io/forms/1061723/159242701050479620/share

Blandine Pais is a property entrepreneur who transitioned from 19 years as a personal assistant to building a thriving property business, generating £15-20k per month.

We cover how she did it, starting from scratch, and building a new life in property despite the odds being stacked against her. From juggling single parenthood to managing setbacks, Blandine shares how she found freedom and flexibility through property investing.

You'll learn...

• How to start a business as a side hustle while keeping your job
• Why resilience is essential for success in entrepreneurship
• How to scale a property business and generate consistent cash flow
• How to find the right mentors and avoid bad advice
• Why it's never too late to start over and pursue your dreams

Instagram - @blandine.pais @heydeanreilly @work.worth.doing.podcast
Website - workworthdoing.transistor.fm

Learn how I built my Airbnb Business below:

• https://join.thesaco.co.uk?affiliate_code=e019b7

Timestamps:

00:44 - Blandine’s transition from PA to property
03:30 - How she started her property journey in 1997
09:12 - Learning new strategies during COVID lockdowns
12:45 - Managing property with the rent-to-rent model
18:36 - Juggling a full-time job and building a business
25:28 - How she scaled her property business
31:22 - Why education and mentorship were key to her success
37:01 - Overcoming challenges as a single mom
43:36 - The importance of curiosity and persistence
52:42 - Advice for starting a side hustle you love

This episode is packed with insights on how to handle uncertainty, stay motivated, and embrace the messy journey of transformation. 

Dean outlines three core steps for tackling change and building a life of flexibility and autonomy.

You'll learn...

- How to clarify your vision and purpose
- Why embracing discomfort is essential for growth
- How to take consistent action while letting go of outcomes
- The importance of focusing on the process, not just the results
- Why privilege gives you the power to create the life you want

Instagram - @heydeanreilly @work.worth.doing.podcast  
Newsletter - workworthdoing.transistor.fm  

Learn how I built my Airbnb Business below:  
- https://join.thesaco.co.uk?affiliate_code=e019b7  

Scott’s story highlights starting his business from scratch, dealing with burnout and anxiety, to building resilience in the face of setbacks, all while balancing life with his partner.

You'll learn...

• How to build a property business from the ground up
• How to be authentic in content creation
• How to document your journey and have fun doing so
• How Scott has managed massive setbacks

Instagram - @scottmacphersxn @heydeanreilly @work.worth.doing.podcast

Newsletter - workworthdoing.transistor.fm

Learn how I built my Airbnb Business below:

• https://join.thesaco.co.uk?affiliate_code=e019b7

Timestamps

00:44 - Starting a business with minimal resources

03:30 - Why Scott moved 400+ miles to start fresh

09:12 - Dealing with anxiety and panic attacks

12:45 - The importance of having a supportive partner

18:36 - Navigating the challenges of building a business

25:28 - The power of documenting your journey

31:22 - Authenticity in property content

37:01 - Managing financial risks and debt

43:36 - The lessons learned from setbacks

52:42 - Finding joy in the small wins along the way

1:01:30 - Building resilience through tough times

You'll learn...

• How to start a fulfilling career by pursuing your passions
• The mental and physical demands of ultra-running
• How to create content that resonates on a personal level
• Tips for building an online presence that stays true to who you are
• Why Tommy lives on the edge of his comfort zone

Instagram - @tommyrunpt @heydeanreilly @work.worth.doing.podcast
Website - workworthdoing.transistor.fm

Learn how I built my Airbnb Business below
- https://join.thesaco.co.uk?affiliate_code=e019b7

Timestamps:

00:44 - Quitting an unfulfilling job for passion
03:30 - First steps into content creation
09:12 - How ultra-running transformed Tommy’s mindset
12:45 - The journey to self-discovery through running
18:36 - Dealing with burnout and finding balance
25:28 - Building an authentic personal brand
31:22 - Lessons learned from ultra-marathons
37:01 - The importance of setting big goals
43:36 - Handling online criticism and negativity
52:42 - Finding meaning in every moment of life
1:01:30 - Why fitness is a gateway to self-improvement
1:13:45 - Reflections on identity and growth
1:25:22 - Connecting with an audience authentically
1:37:50 - The role of self-discipline in achieving goals
1:49:30 - How to sustain motivation for the long term
1:58:00 - Final thoughts on embracing discomfort

Dan shares his journey from university sailing to building a thriving property business, discussing everything from managing multiple Airbnb units to dealing with difficult guests and scaling a business that allows him to travel the world.

***This episode was before Quittable rebranded to Work Worth Doing***

You'll hear us talk about...

• How Dan scaled his side hustle to £70k monthly profit
• How to build a scalable Airbnb business
• How to build a business that suits your desired life
• How to make your business not rely on you

Learn how I built my Airbnb Business below

• https://join.thesaco.co.uk?affiliate_code=e019b7

Instagram - @the_property_athlete @heydeanreilly @quittable.pod

Website - workworthdoing.transistor.fm

Timestamps:

00:44 - 53 Degrees Property business overview

03:30 - Profit breakdown and scaling challenges

05:52 - Dealing with negative feedback and scrutiny

07:06 - Sailing to property: Dan’s background

10:32 - Managing rapid growth and scaling to 100+ units

14:48 - Challenges of the service accommodation industry

18:15 - Dealing with difficult guests and operational hurdles

23:04 - The ethics of selling high-priced property courses

29:46 - Balancing work, travel, and building a remote business

43:36 - The importance of setting long-term goals

Furthermore, he also can help you to become a coach too!

Sam and I discuss his journey from losing his sales job to building a successful online coaching business during COVID. His story is one of resilience, transformation, and taking risks.

***This episode was before Quittable rebranded to Work Worth Doing***

You'll learn...

• How a shock surprise pushed Sam to build a business
• How to get started in online coaching with no qualifications
• The importance of accountability and building client relationships
• Why losing a job or facing adversity can lead to success

Learn how I built my Airbnb Business below
- https://join.thesaco.co.uk?affiliate_code=e019b7

Instagram - @samshortall_limitless @heydeanreilly @work.worth.doing.podcast

Website - workworthdoing.transistor.fm

Timestamps:

00:44 - What Sam had to quit to become a coach

03:15 - Losing a job just before COVID

05:52 - How Sam started his coaching business

09:12 - Starting a business with no safety net

12:59 - Moving to Liverpool to cut costs and go all-in

17:28 - Struggles with self-belief and overcoming adversity

23:00 - Building a team and scaling his coaching business

31:33 - Why you need to delegate tasks in business

43:36 - Dealing with body dysmorphia and fitness insecurities

52:42 - How to get started in coaching with minimal experience

Lewis shares his journey from starting his agency to retiring his mom, and how his focus on authenticity, patience, and long-term thinking led him to success.

***This episode was before Quittable rebranded to Work Worth Doing***

You'll learn...

• How to build a personal brand without being a dickhead
• Why emotions play a crucial role in your marketing
• How to retire your mum by building wealth through business and investments
• Why patience and delayed gratification are key to long-term success

Learn how I built my Airbnb Business below
- https://join.thesaco.co.uk?affiliate_code=e019b7

Instagram - @lightbulbdmediauk @heydeanreilly @work.worth.doing.podcast

Website - workworthdoing.transistor.fm

Timestamps:

00:44 - What most people get wrong about personal branding

03:30 - Building a brand by focusing on emotions

05:42 - Handling negative comments and online trolls

07:06 - How Lewis retired his mom

09:58 - Investing strategies that helped him retire his mom

13:11 - Running a digital marketing agency with 25 clients

17:28 - Why integrity is essential in business

23:04 - How to avoid burnout while running an agency

29:46 - The real cost of scaling a business

37:01 - Advice for building wealth and playing the long game

Neil shares his experience launching brands like Lost Irish Whiskey and MASK during COVID-19, and his insights on spotting opportunities, building businesses from passion, and taking calculated risks.

***This episode was before Quittable rebranded to Work Worth Doing***

You'll learn...

• How to spot opportunities nobody else sees
• How to create a product that resonates deeply with consumers
• Why passion, not just profit, should drive your business decisions
• How to deal with financial stress and losses as an entrepreneur

Learn how I built my Airbnb Business below
- https://join.thesaco.co.uk?affiliate_code=e019b7

Instagram - @cxoneilosands @heydeanreilly @work.worth.doing.podcast
Website - workworthdoing.transistor.fm

Timestamps:

00:44 - Launching Lost Irish Whiskey during COVID
03:30 - Creating whiskey for adventurers
09:43 - The power of human-centric design
15:29 - Starting MASK for domestic PPE production
23:00 - Challenges in PPE supply during the pandemic
29:30 - Building resilience in entrepreneurship
37:27 - Dealing with financial stress and big losses
45:00 - How Halo.ai helps protect racehorses
53:00 - Finding the right moment to take the leap
58:00 - Advice for people unhappy in their current careers

Henri shares his journey from losing everything to rebuilding his life and businesses. His story is one of resilience, learning from failure, and the importance of self-development.

***This episode was before Quittable rebranded to Work Worth Doing***

You'll learn...

• The value of failure and how it can be a powerful teacher
• Why self-care and time management are crucial for success
• How Henri overcame 500k debt and rebuilt his life
• The impact of a near-death experience on Henri's perspective
• How to transition from winging it to mastering your craft

Learn how I built my Airbnb Business below
- https://join.thesaco.co.uk?affiliate_code=e019b7 

Instagram - @hrg_tree_surgeons @heydeanreilly @work.worth.doing.podcast
Website - workworthdoing.transistor.fm

Timestamps:

00:44 - Balancing multiple businesses
03:13 - The importance of morning routines
05:51 - From Fail Forward podcast to Tree Surgery podcast
09:59 - Challenges in the tree surgery industry
17:19 - Life before mentoring and service accommodation
23:15 - Winging it to seven figures, but at a cost
29:04 - Losing everything and starting over
34:49 - Getting into property and service accommodation
41:01 - Health scare: A stroke and its impact
50:01 - Fear of the unknown and stepping out of comfort zones

Joe's journey highlights the ups and downs of leaving a stable career for something completely new, and the resilience needed to pursue what truly fulfills you.

***This episode was before Quittable rebranded to Work Worth Doing***

You'll learn...

• How to recognize when it’s time to make a career change
• How to take risks and trust your gut even without a backup plan
• How to build confidence in front of the camera and the microphone
• How to manage and embrace the uncertainty in a creative career

Learn how I built my Airbnb Business below
- https://join.thesaco.co.uk?affiliate_code=e019b7

Instagram - @joe_caulfield_ @heydeanreilly, @work.worth.doing.podcast
Website - workworthdoing.transistor.fm

Timestamps:

00:44 - Leaving a sales job without a backup plan
03:30 - Turning down a high-paying job offer
09:43 - Finding a passion for broadcasting
17:29 - Getting into broadcasting during COVID
23:21 - Balancing a day job with a broadcasting dream
29:30 - Landing the first big gig
37:27 - Learning to love public speaking
42:21 - Choosing passion over a high salary
47:18 - Finding fulfillment through hard work
53:00 - Advice for those considering a career change

Fears are always going to be there, so get used to them. The trick is dealing with them correctly such that you continue on your path.

Expect to hear stories from the psychological warfare of posting on social media... the fear that could be stopping you taking the risk you want... insights from Outwitting the Devil... and most importantly... how to SOFTEN these inevitable fears and still march forward.

***This episode was before Quittable rebranded to Work Worth Doing***

Learn how I built my Airbnb Business below
- https://join.thesaco.co.uk?affiliate_code=e019b7

Instagram - @heydeanreilly @work.worth.doing.podcast
Website - workworthdoing.transistor.fm

***This episode was before Quittable rebranded to Work Worth Doing***

Learn how I built my Airbnb Business below
- https://join.thesaco.co.uk?affiliate_code=e019b7

Instagram - @heydeanreilly @work.worth.doing.podcast
Website - workworthdoing.transistor.fm

Episode Flow:
1. Dean's career progression in sales, from telesales to account executive
2. Investing in property courses and mentorship to change his career path
3. Losing almost £40,000 and financial struggles in the Airbnb business
4. Pivoting the business model to become profitable
5. The importance of pursuing work you care about, beyond just financial gain