Michael Greenberg specialises in digital operations, helping businesses optimise workflows through AI tools, automation systems, and strategic outsourcing rather than adding more hours to the working week.

Michael walks through practical approaches to integrating AI and automation into daily business operations, including specific note-taking tools and workflow applications that reduce manual effort. 

He explains how independent professionals can use outsourcing strategically to focus on high-value work, and why choosing the right combination of tools matters more than adopting every new application. 

The conversation covers how to evaluate which tasks genuinely benefit from automation versus those that need human judgement, a distinction that matters more for solo operators managing everything themselves.

Wisepreneurs explores how women over 50 monetize expertise and build sustainable solopreneur practice.

How to connect with Michael Greenberg

Business Website https://www.3rdbrain.co

Personal Website https://gentof.tech/

LinkedIn https://www.linkedin.com/in/gentoftech/

Mentioned on the podcast

Books
2 Second Lean

Apps

• Obsidian
• Tana
• Roam Research
• ClickUp
• Notion
• Snipd
• ReadWise
• Trello
• Zapier
• make.com
• Swell.ai
• Google Sheets

Support the show

Connect with Nigel Rawlins
Website: https://wisepreneurs.com.au/
LinkedIn: https://www.linkedin.com/in/nigelrawlins/

Free assessments for independent professionals: https://wisepreneurs.com.au/field-guides/

The Wisepreneur newsletter, practical thinking for experienced independent professionals, every Tuesday: https://wisepreneurs.com.au/newsletter

Support the show: https://www.buzzsprout.com/2311675/supporters/new

Annette Densham co-founded the Audacious Agency to help business owners use storytelling and business awards as practical visibility strategies, drawing on her background in journalism and PR.

Annette explains how business award submissions work as a structured approach to professional visibility rather than just a trophy exercise. 

She covers how to identify the right awards, craft compelling narratives from real business experience, and use the process itself to clarify your professional story. 

The conversation addresses why personal branding built through earned recognition carries more weight than self-promotion, and how independent professionals can use award entries and media storytelling to build credibility without large marketing budgets. 

Her journalism training shapes an approach grounded in finding the genuine story rather than manufacturing one.

Wisepreneurs explores how women over 50 monetize expertise and build sustainable solopreneur practice.

Offers
Award Winning Free Training
https://montavi.thrivecart.com/award-winning-free-tranining/

Mentions

• Stevie Awards https://stevieawards.com/
• Telstra Best of Business Award
• Sale of the Century (TV Show)
• Crikey (Online Journalism Platform)
• Kochie ( Kochie Business Builders) https://www.kochiesbusinessbuilders.com.au/

Connect with Annette Densham
The Audacious Agency https://theaudaciousagency.com/

Support the show

Connect with Nigel Rawlins
Website: https://wisepreneurs.com.au/
LinkedIn: https://www.linkedin.com/in/nigelrawlins/

Free assessments for independent professionals: https://wisepreneurs.com.au/field-guides/

The Wisepreneur newsletter, practical thinking for experienced independent professionals, every Tuesday: https://wisepreneurs.com.au/newsletter

Support the show: https://www.buzzsprout.com/2311675/supporters/new

Kate Toon created Recipe for SEO Success to teach solopreneurs SEO, copywriting, and how to build sustainable online income.

With 16 years in business and four podcasts, Kate shares practical frameworks for solopreneurs building visible online presence: 

• why every service business needs a WordPress site they own and control, 
• how SEO works as a long-term discoverability strategy, 
• why personal branding beats hiding behind a company name in a crowded market, and 
• how to keep technology minimal while achieving outsized results. 

She also discusses using AI tools like Magai for content creation, delegating strategically rather than doing everything yourself, and building passive income through courses and membership communities.

Wisepreneurs explores how women over 50 monetize expertise and build sustainable solopreneur practice.

Mentioned on the podcast 

• Magai · All the World's Best AI Models in One Subscription
• This American Life and the host Ira Glass This American Life
• Rand Fishkin
• Neil Patel
• Robert Vlach https://www.wisepreneurs.au/s1e38
• Mark Goulston https://www.wisepreneurs.au/s1e8

Connect with Kate Toon

• LinkedIn https://www.linkedin.com/in/katetoon/
• Website Business mentor & digital marketing coach for humans
• Facebook https://www.facebook.com/kateToon
• Instagram (@kateToon)
• YouTube Kate Toon
• Kate Toon (@KateToon) on X

Kate Toon's Online Programs
https://therecipeforseosuccess.com/seo-courses/ecourse/
Kate Toon Copywriter | Clever, creative copywriting
https://www.clevercopywritingschool.com/

Books By Kate Toon
Six Figures While You Sleep
Six Figures in School Hours
The Confessions of a Misfit Entrepreneur

Support the show

Connect with Nigel Rawlins
Website: https://wisepreneurs.com.au/
LinkedIn: https://www.linkedin.com/in/nigelrawlins/

Free assessments for independent professionals: https://wisepreneurs.com.au/field-guides/

The Wisepreneur newsletter, practical thinking for experienced independent professionals, every Tuesday: https://wisepreneurs.com.au/newsletter

Support the show: https://www.buzzsprout.com/2311675/supporters/new

Gill Andrews shows independent professionals how their website copy either generates inquiries or drives visitors away — and the difference comes down to specific, fixable mistakes most solopreneur sites make. 

A conversion copywriter and CRO consultant who wrote Making Your Website Work, Gill works exclusively with English-speaking service providers and teaches the same method she uses on client sites: 

• Lead with clarity and value in the first lines of every page 
• Avoid the design mistakes that cost you inquiries, and 
• Write for the specific objections your ideal client brings

Gill also introduces her online course "Website Messaging for Freelancers & Small Businesses," a systematic framework developed over two years to help solopreneurs define their ideal client, clarify their offer, and write website copy without hiring a consultant.

Wisepreneurs explores how women over 50 monetize expertise and build sustainable solopreneur practice.

Mentioned on the podcast

• Book: Making Your Website Work, 100 Copy and Design Tweaks for Smart Business Owners by Gill Andrews
• Freelancer Homepage Checklist: Turn Your Visitors into Paying Clients https://gillandrews.com/freelancer-homepage-checklist-template/
• Website Messaging for Freelancers & Small Businesses Course https://gillandrews.com/online-course-find-unique-value-proposition/
• The Emergent Approach To Strategy by Peter Compo

Connect with Gill Andrews
LinkedIn https://www.linkedin.com/in/gill-andrews/
Website https://gillandrews.com/

Related reading on Wisepreneurs:

• What your website should actually do for you as an independent professional
• Why experienced professionals can never afford to stop being visible

Support the show

Connect with Nigel Rawlins
Website: https://wisepreneurs.com.au/
LinkedIn: https://www.linkedin.com/in/nigelrawlins/

Free assessments for independent professionals: https://wisepreneurs.com.au/field-guides/

The Wisepreneur newsletter, practical thinking for experienced independent professionals, every Tuesday: https://wisepreneurs.com.au/newsletter

Support the show: https://www.buzzsprout.com/2311675/supporters/new

Fiona Allman-Treen builds business-generating websites using a five-step strategy and ideal client research for solopreneurs.

Based in Hastings, UK, Fiona's agency creates custom WordPress and Shopify websites for service businesses and scaling companies. 

The conversation covers 

• why most websites fail as shop windows rather than business assets, 
• how to define your ideal client using demographics, geographics, and psychographics before touching design, 
• why 100 targeted visitors beats 1,000 untargeted ones, 
• how website automation removes repetitive tasks from your desk, and 
• the common mistake of leading with what you do rather than what the client gains. 

Fiona also discusses her book Website Mastery for Business Owners Who Don't Speak Tech and how it filters the right clients before they make contact.

Wisepreneurs explores how women over 50 monetize expertise and build sustainable solopreneur practice.

Fiona's Book & Course
Website Mastery for Business Owners Who Don't Speak Tech by Fiona Allman-Treen
Download a free chapter here: http://www.websitemasterybook.com
Publishing Mastery: from Ink to Impact http://www.publishingmastery.co.uk

Where you can connect with Fiona Allman-Treen
Facebook: http://www.facebook.com/fatpromotions
Twitter: http://twitter.com/fatpromotions
LinkedIn: https://www.linkedin.com/in/fatpromotions-website-design/
Instagram: http://www.instagram.com/fatpromotions
YouTube: https://www.youtube.com/@fatpromotions

Support the show

Connect with Nigel Rawlins
Website: https://wisepreneurs.com.au/
LinkedIn: https://www.linkedin.com/in/nigelrawlins/

Free assessments for independent professionals: https://wisepreneurs.com.au/field-guides/

The Wisepreneur newsletter, practical thinking for experienced independent professionals, every Tuesday: https://wisepreneurs.com.au/newsletter

Support the show: https://www.buzzsprout.com/2311675/supporters/new

Debra Zahay-Blatz taught digital marketing for 25 years at St. Edwards University after 17 years in customer data management.

With a Kellogg School of Management MBA and a PhD in customer information management, Debra explains how solopreneurs build sustainable digital marketing strategy. 

The conversation covers 

• selecting channels based on where customers actually search rather than where you prefer to be, 
• why brand is a promise rather than a logo using William Arruda's framework, 
• Michael Porter's differentiation strategies applied to solo practice, 
• why organisational learning is the one competitive advantage that cannot be imitated, and 
• how AI is becoming table stakes where learning speed rather than tool access is the real differentiator. 

Debra also shares her three-priorities-per-day productivity approach and her Digital Marketing Management book, a framework for independent professionals making sense of a crowded digital landscape.

Wisepreneurs explores how women over 50 monetize expertise and build sustainable solopreneur practice.

As mentioned in this podcast

• Digital Marketing Management: A Handbook for the Current (or Future) CEO by Debra Zahay-Blatz
• Arriving Today by Christopher Mims
• The Emergent Approach to Strategy by Peter Compo https://emergentapproach.com/
• Works by William Arruda on personal branding https://williamarruda.com/

Connect with Dr Debra Zahay-Blatz

Google Scholar https://scholar.google.com/citations?user=WIsqcQMAAAAJ&hl=en
St. Edwards University https://www.stedwards.edu/directory/employees/blatz-debra-z
LinkedIn https://www.linkedin.com/in/drzahay/

Support the show

Connect with Nigel Rawlins
Website: https://wisepreneurs.com.au/
LinkedIn: https://www.linkedin.com/in/nigelrawlins/

Free assessments for independent professionals: https://wisepreneurs.com.au/field-guides/

The Wisepreneur newsletter, practical thinking for experienced independent professionals, every Tuesday: https://wisepreneurs.com.au/newsletter

Support the show: https://www.buzzsprout.com/2311675/supporters/new

Hazel Edwards OAM wrote 200 books over 50 years sustaining independent professional practice as an Australian authorpreneur. 

Best known for There's a Hippopotamus on My Roof Eating Cake — now 45 years old and adapted into a film, touring musical, braille, and Auslan — Hazel has sustained a prolific independent writing practice without organisational support, adapting from print to digital across five decades. 

The conversation covers 

• how creative independence compounds over a lifetime, 
• sustaining income through multiple streams including writing courses and mentoring, 
• her Complete Your Book in a Year program run for seven years at the Public Records Office, 
• how AI presents an existential challenge for professional authors comparable to the Industrial Revolution, and 
• what cognitive vitality looks like when creative work continues well into later life.

Wisepreneurs explores how women over 50 monetize expertise and build sustainable solopreneur practice.

Connect with Hazel Edwards OAM

Hazel Edwards' official website: HazelEdwards.com
LinkedIn https://www.linkedin.com/in/hazel-edwards-oam-0b4543a/

Mentioned on the podcast

• Judith Rodriguez
• Meredith Fuller https://meredithfuller.com.au/
• George Pappas
• Aileen Hall
• Ryan Kennedy
• Dag Hammarskjöld https://en.wikipedia.org/wiki/Dag_Hammarskjold
• Toorak Teachers College
• Holmes Glen Tafe
• Penguin Publishing
• Hodder and Stoughton
• Amba Press (Alicia Cohen) https://ambapress.com.au/
• Untapped Project of Melbourne University https://untapped.org.au/

Books

• There's a Hippopotamus on our Roof Eating Cake by Hazel Edwards
  https://hazeledwards.com/picture-books/
• Not Just a Piece of Cake: Being an Author by Hazel Edwards
  https://hazeledwards.com/book/not-just-a-piece-of-cake-being-an-author/
• Antarctic Dad  by Hazel Edwards
• F2M: The Boy Within  by Hazel Edwards and Ryan Kennedy
• Cleaved  by Jane Cafarella (Hazel's student) https://janecafarella.com.au/
• Wed, Then Dead On The Ghan, by Hazel Edwards https://hazeledwards.com/book/wedthen-dead-on-the-ghan/

*OAM
The Order of Australia recognises Australians with outstanding service or exceptional achievement.

Support the show

Connect with Nigel Rawlins
Website: https://wisepreneurs.com.au/
LinkedIn: https://www.linkedin.com/in/nigelrawlins/

Free assessments for independent professionals: https://wisepreneurs.com.au/field-guides/

The Wisepreneur newsletter, practical thinking for experienced independent professionals, every Tuesday: https://wisepreneurs.com.au/newsletter

Support the show: https://www.buzzsprout.com/2311675/supporters/new

Anna Molnar helps women entrepreneurs over 50 navigate pricing for freelancers and charge what their expertise is worth. Based in The Hague and working internationally, Anna left embassy work at 40 to build an independent coaching practice focused on expertise monetisation for women solopreneurs.

Anna explains why undercharging is the most consistent problem among women entrepreneurs and why many women struggle to discuss money before they can even set prices. She covers the connection between professional self-perception and asking for appropriate fees.

She speaks six languages and draws on fiction and story structure as coaching tools — the kind of lifelong learning she argues keeps independent practice relevant over time.

Mentions and references: Denise Duffield Thomas.

Connect with Anna: blossomempoweringevents.nl | LinkedIn: Anna Molnár

Wisepreneurs explores how women over 50 monetise expertise and build sustainable solopreneur practice.

Support the show

Connect with Nigel Rawlins
Website: https://wisepreneurs.com.au/
LinkedIn: https://www.linkedin.com/in/nigelrawlins/

Free assessments for independent professionals: https://wisepreneurs.com.au/field-guides/

The Wisepreneur newsletter, practical thinking for experienced independent professionals, every Tuesday: https://wisepreneurs.com.au/newsletter

Support the show: https://www.buzzsprout.com/2311675/supporters/new

Knowledge management tools for independent professionals who need to curate information without burning out in the process. Tomas Baranek is a Czech publisher who translates notable English-language books on personal development, productivity, and science.

After experiencing burnout himself, Tomas rebuilt his working practice around specific tools like Readwise and Roam Research for building a second brain and selective information curation. 

He explains practical approaches to managing knowledge sustainably, why self-care and seeking help matter for independent professionals without organisational support systems, and how decades of reading the best thinking on productivity shaped his own recovery.

Mentions and references: Readwise. Roam Research. Melvil Publishing (melvil.cz).

Connect with Tomáš: barys.me | LinkedIn: Tomáš Baránek | Medium: lifehacky.net

Wisepreneurs explores how independent professionals turn accumulated expertise into sustainable practice.

Support the show

Connect with Nigel Rawlins
Website: https://wisepreneurs.com.au/
LinkedIn: https://www.linkedin.com/in/nigelrawlins/

Free assessments for independent professionals: https://wisepreneurs.com.au/field-guides/

The Wisepreneur newsletter, practical thinking for experienced independent professionals, every Tuesday: https://wisepreneurs.com.au/newsletter

Support the show: https://www.buzzsprout.com/2311675/supporters/new

The Indie List is a high-touch marketplace connecting freelance marketing professionals with Irish clients, serving approximately 7,000 independent marketing solopreneurs. 

Úna shares how she left advertising in 2005 when the industry proved unwelcoming to women with young children, how a LinkedIn post during COVID became a business, and how The Indie List's earn-learn-connect model addresses the isolation, cashflow uncertainty, and admin burden freelancers face working alone. 

The conversation covers ageism in advertising for senior creatives, in-demand skills including digital marketing, SEO, content creation and strategic planning, and why the average Indie List member age of 46 reflects a growing cohort of experienced professionals choosing independence over employment.

Wisepreneurs explores how women over 50 monetize expertise and build sustainable solopreneur practice.

Mentioned: Peter McPartlin (co-founder), Amanda Morey (community manager), Faye Goldstein on winning portfolios
Guests on both The Indie List and Wisepreneurs: Tash Menon, Melisa Liberman, Jon Younger, Robert Vlach
Connect with Una and The Indie List
LinkedIn: Una Herlihy
Website: indielist.ie
YouTube: youtube.com/channel/UCCyDKJnk0X46CxeTeowEQ1Q

Support the show

Connect with Nigel Rawlins
Website: https://wisepreneurs.com.au/
LinkedIn: https://www.linkedin.com/in/nigelrawlins/

Free assessments for independent professionals: https://wisepreneurs.com.au/field-guides/

The Wisepreneur newsletter, practical thinking for experienced independent professionals, every Tuesday: https://wisepreneurs.com.au/newsletter

Support the show: https://www.buzzsprout.com/2311675/supporters/new