
Every Sunday I share a quick update from my last week in business as a Canadian family lawyer and cofounder of my legal tech company (Visto.ai), including the best stories, lessons learned, key takeaways, book(s) I'm reading and more. Make sure to subscribe so you don't miss it!
And make sure to join the substack so you never miss an episode here: https://joshschachnow.substack.com/
Episodes

Oct 12, 2025
Oct 12, 2025
13 min
Join Josh in this week’s vlog as he shares updates on his busy life balancing a family law practice and co-founding a tech company in the Greater Toronto Area. Josh discusses the ebb and flow of litigation work, details his tech firm's advancements in automated immigration forms, and highlights his thoughts on the importance of niche solutions in tech development.
Additionally, he reviews the books 'Crushing It' by Gary Vaynerchuk and 'Mastery' by Robert Green, sharing insights and recommendations for readers interested in personal growth and mastery.
Never miss an update by joining the substack here: https://joshschachnow.substack.com/
00:00 Introduction and Weekly Update
01:04 Law Firm Insights and Court Preparations
04:30 Tech Company Developments and Niche Strategies
07:58 Community Building and AI in Legal Practice
08:38 Book Reviews and Recommendations
12:44 Conclusion and Thanksgiving Wishes

Oct 5, 2025
Oct 5, 2025
17 min
Join Josh in his latest vlog as he returns to weekly updates, sharing why he transitioned to family law after years of practicing immigration law. Josh discusses his dual roles as a Canadian tech founder and lawyer, the importance of focus for entrepreneurs, and how he balances his career with content creation.
He offers insights into his decision-making process, the valuable mentorships he's received, and how he's leveraging AI in legal research.
Stay tuned for book recommendations, updates on his legal tech company Visto, and tips on building a personal brand. Subscribe and follow along for weekly episodes and fresh content here: https://joshschachnow.substack.com/
My NotebookLM guide here: https://joshschachnow.substack.com/p/the-free-ai-tool-thats-changing-how
00:00 Introduction and Welcome Back
00:16 Balancing Podcasting and Vlogging
01:47 Focusing on Vista and Legal Practice
02:46 Weekly Content and Personal Branding
04:26 Switching to Family Law
10:19 Mentorship, Books, and AI in Legal Practice
13:39 Community for Legal Professionals
14:31 Current Reads and Recommendations
16:53 Conclusion and Farewell

Jul 29, 2025
Jul 29, 2025
45 min
In this episode of the Solopreneur Grind Podcast, Josh welcomes John from Think It, Be It. John shares his transformative journey from being an unsatisfied CPA to a highly successful entrepreneur, thanks to an epiphany triggered by the classic book 'Think and Grow Rich.'
At 50, facing personal and professional challenges, John discovered the book’s secret and developed a 12-minute daily technique that skyrocketed his success. Now, he teaches this method through his course, 'The Science of Success,' his book, and to top athletes and students.
This episode is packed with insights about overcoming unconscious actions, setting intentions, and making daily progress toward an exceptional life.
00:00 Introduction and Guest Welcome
00:28 John's Entrepreneurial Journey
01:44 Discovering the Secret to Success
03:20 Applying the 12-Minute Technique
04:13 Teaching and Sharing the Methodology
05:15 Advice for Aspiring Entrepreneurs
07:56 The Science Behind Success
11:13 Emotional Turning Points
14:37 The Power of Daily Actions
21:04 Understanding the Subconscious Mind
24:06 The Importance of Being Highly Organized
24:40 Deep Thinking: A Key to Success
25:09 Continuous Learning and Strategic Wisdom
25:44 Daily Business Affirmations
26:47 The Power of Intentionality and Focus
29:18 Epiphanies that Change Lives
30:51 Understanding Unconscious Actions
34:52 Implementing the Methodology
38:16 The Missing Secret and Final Thoughts
---
Want to get even more solopreneur podcasts, content and the first 3 chapters of my e-book: “Just Get Started: Key business lessons from 2 businesses, 5 years and 100+ podcast episodes”?
Make sure you're subscribed on my Substack here: https://joshschachnow.substack.com/
---
Where to find John:
https://themissingsecret.org/
#sgpodcast #solopreneur #businesspodcast

Jul 9, 2025
Jul 9, 2025
27 min
In this episode of the Solopreneur Grind Podcast, host Josh is joined by Emily, founder of Female Founder Space. Emily shares her journey from various corporate roles to becoming an operations consultant for small business founders with a focus on marketing agencies.
She delves into the challenges and strategies of transitioning from corporate work to solopreneurship, emphasizing the importance of networking, sales, and understanding one's own value. The discussion also covers practical advice on time management, outsourcing tasks, and dealing with the inherent uncertainties of running a solo business.
Tune in for valuable insights and actionable tips, especially helpful for solopreneurs and small business owners looking to optimize their operations and grow their ventures.
00:00 Introduction and Guest Welcome
00:15 Emily's Background and Career Journey
02:12 Transition to Entrepreneurship
04:24 Building a Client Base and Sales Strategies
10:57 Operations and Time Management Tips
15:45 Outsourcing and Tools for Efficiency
19:12 Challenges and Overcoming Fears
24:43 Key Advice for Solopreneurs
26:08 Conclusion and Contact Information
---
Want to get even more solopreneur podcasts, content and the first 3 chapters of my e-book: “Just Get Started: Key business lessons from 2 businesses, 5 years and 100+ podcast episodes”?
Make sure you're subscribed on my Substack here: https://joshschachnow.substack.com/
---
Where to find Emily:
https://www.linkedin.com/in/emily-hatton/
https://thefemalefounderspace.com/
#sgpodcast #solopreneur #businesspodcast

Jun 24, 2025
Jun 24, 2025
35 min
In this episode of the Solopreneur Grind podcast, host Josh Schachnow chats with Sam Anthony, founder of YourNews.com, about the future of news media and entrepreneurship. Sam discusses his venture into a hyper-local news platform, covering everything from local events to national news.
He explains the downfall of traditional media, the transition to digital platforms, and the new ways to monetize news through local journalism. Sam also shares insights on his journey from investment banking to creating a scalable news model, and the role of equity crowd funding in raising capital for startups.
Tune in to learn about the innovative changes in media and how entrepreneurs can navigate the evolving landscape:
00:00 Introduction and Guest Welcome
00:34 Sam Anthony's Background and Business Overview
01:09 Challenges in Traditional Media and the Shift to Digital
02:51 The Birth of a New Business Model
04:41 Scaling and Monetizing Local News
07:44 Building a News Marketplace
13:21 Advertising Strategies and Future Plans
17:38 User-Generated Content and Liability
20:28 Challenges of Scaling a Business
22:36 Equity Crowdfunding Explained
30:46 Advice for Aspiring Entrepreneurs
34:02 How to Get Involved and Invest
---
Want to get even more solopreneur podcasts, content and the first 3 chapters of my e-book: “Just Get Started: Key business lessons from 2 businesses, 5 years and 100+ podcast episodes”?
Make sure you're subscribed on my Substack here: https://joshschachnow.substack.com/
---
Where to find Sam:
https://yournews.com/
https://www.linkedin.com/in/sam-anthony-yournews/
#sgpodcast #solopreneur #businesspodcast

Jun 12, 2025
Jun 12, 2025
34 min
Join us in this engaging episode of the Solopreneur Grind Podcast where Josh interviews Cathy Mitchell from WP Barista. Get insights into Kathy’s journey from starting a WordPress-focused agency in 2008 to evolving her business with the changing digital landscape.
Kathy shares her initial struggles, adapts to market changes, and provides valuable advice for content creators and solopreneurs on leveraging AI and maintaining productivity. Learn about the significance of community, the importance of PR in today's SEO-driven world, and strategic tips for building a successful solopreneur career. Don't miss out on Kathy’s practical tips and lessons learned from years of experience in the tech industry.
00:00 Introduction and Guest Welcome
00:23 Kathy's Journey into WordPress
00:49 Starting the Business and Early Challenges
03:37 Transition to Full-Time and Business Growth
06:40 Market Evolution and Industry Insights
13:34 Productivity and Mental Health as a Solopreneur
18:16 Adapting to AI and Future Trends
24:00 Advice for Content Creators
26:49 Tools and Resources for Solopreneurs
31:34 Challenges and Final Advice
33:54 Conclusion and Contact Information
---
Want to get even more solopreneur podcasts, content and the first 3 chapters of my e-book: “Just Get Started: Key business lessons from 2 businesses, 5 years and 100+ podcast episodes”?
Make sure you're subscribed on my Substack here: https://joshschachnow.substack.com/
---
Where to find Cathy Mitchell:
https://wpbarista.com/
https://www.linkedin.com/in/cathyamitchell/

Jun 4, 2025
Jun 4, 2025
32 min
Join Josh on the Solopreneur Grind Podcast as he chats with Jacky, the founder of AnswerHQ, an AI customer service assistant that significantly reduces customer support questions for small businesses and startups.
Jacky shares his journey of creating AnswerHQ as a side hustle while working full-time, his approach to time management, and the tools and strategies he uses to operate efficiently. This episode delves into key aspects of startup life, including market validation, customer acquisition, building in public, and the importance of focusing on solving pain points. Whether you're a technical or non-technical founder, there are invaluable insights to help you start and grow your own business.
More specifically:
00:00 Introduction and Guest Welcome
00:15 Jacky's Background and Answer HQ Overview
00:33 The Journey from Side Hustle to Full-Time
01:23 Challenges and Initial Idea Validation
03:47 Building the MVP and Early Customer Acquisition
08:14 Leveraging AI Tools for Productivity
12:03 Time Management and Personal Strategies
15:13 Biggest Challenges as a Solopreneur
15:34 Shifting Focus: From Product Development to Marketing
15:56 The Challenges of Marketing and Sales for Startups
18:41 The Importance of Understanding Your Business Goals
19:55 Funding Your Startup: Options and Considerations
20:57 Building for Pain Points, Not Ideas
21:54 The Role of MVPs and No-Code Tools
26:12 The Concept and Benefits of Building in Public
30:12 Final Advice for Aspiring Entrepreneurs
---
Want to get even more solopreneur podcasts, content and the first 3 chapters of my e-book: “Just Get Started: Key business lessons from 2 businesses, 5 years and 100+ podcast episodes”?
Make sure you're subscribed on my Substack here: https://joshschachnow.substack.com/
---
Where to find Jacky:
https://answerhq.co/
https://www.linkedin.com/in/jjackyliang/
https://jjacky.substack.com/
#sgpodcast #solopreneur #businesspodcast

May 27, 2025
May 27, 2025
25 min
In this episode of the Solopreneur Grind podcast, I talk to Joe Rando, the CEO and founder of Lifestarr.
Joe shares his unique career journey from obtaining a degree in physics and developing shopping centers to founding successful companies like Trade Area Systems and now Lifestarr.
We discuss the challenges and strategies for solopreneurs, including lead generation, productivity, and the importance of having clear goals. Joe also provides actionable tips for aspiring solopreneurs and emphasizes the importance of community support in navigating the solopreneur journey.
More specifically:
00:00 Introduction and Guest Welcome
00:30 Joe Rando's Background and Career Journey
01:26 Transition to Solopreneurship and Founding Lifestar
04:28 Challenges and Strategies for Solopreneurs
06:07 The Solopreneur Industry and Future Trends
08:14 Productivity Tips for Solopreneurs
11:07 Lead Generation and Sales Advice
13:56 Steps to Start a Solopreneur Business
19:30 Recommended Tools and Final Advice
23:21 Conclusion and Contact Information
And much more.
---
Want to get even more solopreneur podcasts, content and the first 3 chapters of my e-book: “Just Get Started: Key business lessons from 2 businesses, 5 years and 100+ podcast episodes”?
Make sure you're subscribed on my Substack here: https://joshschachnow.substack.com/
---
Where to find Joe Rando:
https://www.linkedin.com/in/joerando/
https://www.lifestarr.com/

May 12, 2025
May 12, 2025
36 min
In this episode of the Solopreneur Grind Podcast, I talk to Lucas Root about:
00:00 Introduction and Guest Welcome
01:20 Lucas Root's Background and AI Journey
04:31 The Evolution of AI and ChatGPT
09:26 AI Agents and Their Practical Applications
21:59 Using AI to Optimize Workflows
29:25 Top Tools for Non-Coders
33:07 Final Thoughts and Recommendations
And much more.
---
Want to get even more solopreneur podcasts, content and the first 3 chapters of my e-book: “Just Get Started: Key business lessons from 2 businesses, 5 years and 100+ podcast episodes”?
Make sure you're subscribed on my Substack here: https://joshschachnow.substack.com/
---
Where to find Lucas Root:
https://lucasroot.com/
https://www.amazon.ca/Agent-Playbook-Practical-Strategies-Professionals-ebook/dp/B0DPGYMRFS/

May 5, 2025
May 5, 2025
27 min
In this episode of the Solopreneur Grind Podcast, I talk to Matthew Stafford about:
00:00 Introduction and Guest Welcome
00:24 Matthew Stafford's Background and Entrepreneurial Journey
01:26 First Business and Transition to Online Sales
04:17 Insights on Sales and Marketing
05:52 Advice for Aspiring Entrepreneurs
09:21 Daily Routine and Personal Productivity Tips
17:18 Building a Successful E-commerce Business
22:58 Tools and Resources for Solopreneurs
25:05 Final Thoughts and Contact Information
And much more.
---
Want to get even more solopreneur podcasts, content and the first 3 chapters of my e-book: “Just Get Started: Key business lessons from 2 businesses, 5 years and 100+ podcast episodes”?
Make sure you're subscribed on my Substack here: https://joshschachnow.substack.com/
---
Where to find Matthew Stafford:
https://buildgrowscale.com/book-a-call
Building million dollar e-commerce businesses | SG Podcast Episode 132 with Matthew Stafford
#sgpodcast #solopreneur #businesspodcast
