The podcast and community for solopreneurs! Join Canadian lawyer/tech founder Josh Schachnow as he interviews successful solopreneurs to hear their best stories, lessons, advice and more. If you want to learn the secrets of successful small businesses or get solopreneur business ideas, then the Solopreneur Grind Podcast is just for you. And make sure to join the substack so you never miss an episode here: https://joshschachnow.substack.com/podcast
Episodes
4 days ago
4 days ago
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
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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
Tuesday Jun 24, 2025
Tuesday Jun 24, 2025
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
Thursday Jun 12, 2025
Thursday Jun 12, 2025
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/
Wednesday Jun 04, 2025
Wednesday Jun 04, 2025
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
Tuesday May 27, 2025
Tuesday May 27, 2025
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/
Monday May 12, 2025
Monday May 12, 2025
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/
Monday May 05, 2025
Monday May 05, 2025
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
Friday Apr 04, 2025
Friday Apr 04, 2025
In this episode of the Solopreneur Grind Podcast, I talk to Gal Ratner about:
00:00 Introduction and Guest Welcome
00:13 About Shop Snap: A Unique E-commerce Platform
00:57 The Origin Story of Shop Snap
01:59 Team and E-commerce Industry Insights
03:26 Steps to Start a SaaS Business
10:56 Challenges and Advice for Entrepreneurs
13:51 The Role of AI in Software Development and Marketing
17:52 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 Gal Ratner:
https://www.linkedin.com/in/galratner/
https://www.shopsnap.io/
https://www.invertedsoftware.com/
https://www.blogcloud.io/
#sgpodcast #solopreneur #businesspodcast
Tuesday Mar 25, 2025
Tuesday Mar 25, 2025
In this episode of the Solopreneur Grind Podcast, I talk to Philippe Burns about:
00:00 Introduction and Guest Welcome
00:15 Philip's Background and Tech Thursday's Origin
01:04 Scaling Tech Thursday and Neo Financial Experience
05:45 The Importance of In-Person Events
08:33 Starting an In-Person Event Business
12:29 Challenges and Business Model
16:19 Future Plans and Market Expansion
19:41 Encouragement for Aspiring Entrepreneurs
21:32 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 Philippe Burns:
https://www.linkedin.com/in/philippe-burns/
https://www.linkedin.com/company/tech-thursday/
#sgpodcast #solopreneur #businesspodcast
Wednesday Mar 05, 2025
Wednesday Mar 05, 2025
In this episode of the Solopreneur Grind Podcast, I talk to Ryan Cote about:
00:00 Introduction and Guest Welcome
00:27 Ryan's Background and Family Business
02:00 Starting the Side Business
04:10 The Evolution of SEO and Digital Marketing
07:26 Advice for Aspiring Entrepreneurs
12:26 Balancing Multiple Businesses
18:07 Final Thoughts and Contact Information
And much more.
---
Want to follow along on my solopreneur journey and get 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 Ryan Cote:
https://ballantinedigital.com/
https://www.functionalmedicineseo.com/
Building and Growing Businesses and Side Hustles | SG Podcast Episode 129 with Ryan Cote
#sgpodcast #solopreneur #businesspodcast