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Home » Jimmy Rose — From AdSense Gold Rush to Revolutionizing Client Onboarding with Content Snare: The Journey of an Engineer Turned SaaS Entrepreneur (TMMF #003)

Jimmy Rose — From AdSense Gold Rush to Revolutionizing Client Onboarding with Content Snare: The Journey of an Engineer Turned SaaS Entrepreneur (TMMF #003)

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“It’s really rough. It took me a long time to sort of unlearn trying to sell by features.”

— James Rose

Jimmy, an ex-engineer turned successful SaaS entrepreneur, takes us through his fascinating journey in the tech and software world. From his early days in the AdSense gold rush era to founding a web design agency, and eventually transitioning to a SaaS model with Content Snare, Jimmy’s story is a tale of constant learning, adaptation, and problem-solving.

In this insightful conversation, Jimmy shares his experiences, the highs and lows of entrepreneurship, and how he found his niche in the software industry. Jimmy’s entrepreneurial journey is a masterclass in adapting to market needs, understanding customer pain points, and the importance of constant iteration and feedback in product development. His journey from a web design agency to a thriving SaaS business is not just inspiring but also full of practical insights for aspiring entrepreneurs and software developers.

Please enjoy this insightful conversation with Jimmy!

Listen to the episode on your favorite podcast platform. Watch the interview on YouTube here.

Want to hear more episodes about entrepreneurship and software innovation? Check out our conversation with Amar Ghose, co-founder of Zen Maid on how he goes about understanding customers and solving problems for them.

What was your favorite insight or lesson from this episode? Share your thoughts in the comments below.



  • 02:16 Jimmy’s Entrepreneurial Journey
  • 03:07 The Evolution of Content Snare
  • 03:52 Identifying the Problem and Building a Business
  • 05:41 The Importance of Customer Feedback and Iteration
  • 07:02 The Power of Open-Ended Questions
  • 08:05 Understanding Your Customers’ Perspective
  • 14:32 The Journey to Targeting the Accounting Industry
  • 19:55 Balancing Product Features for Different Industries
  • 21:58 Standing Out in a Competitive Market
  • 25:38 The Struggles of Building a Multi-Functional Product
  • 26:09 Finding Product-Market Fit in the Accounting Industry
  • 26:41 The Journey from Web Design to Accounting
  • 29:27 The Importance of Customer Feedback in Product Development
  • 30:17 The Challenges of Launching New Features
  • 31:47 The Role of Messaging in Reducing Churn
  • 32:25 The Concept of Message-Market Fit
  • 35:28 The Transition from Automation Consultancy to SaaS
  • 39:33 The Power of Storytelling in Understanding Your Audience
  • 41:31 The Challenge of Communicating a Unique Product Offering
  • 45:22 The Joy of Trying New Beers
  • 46:32 Closing Remarks and Appreciation


  • “Almost every single one of them talked about getting content from clients being one of the biggest pains. And that was kind of like my immediate somewhat validation… the passionate language people use, just like someone said, literally said, ‘this is the biggest pain in my ass.’ Someone said, ‘this makes, this makes me want to leave the industry.'”
  • “I remember I just interviewed a whole lot of designers all around the world… It was just like, ‘tell me about your business and your problems.’… I came out of the interviews with a completely different product.”
  • “We ended up getting a lot of non-web design clients through SEO… eventually we realized… we’ve got like a few random companies here that aren’t web designers… Who should we target? And actually, it took us a long time to land on accounting.”
  • “Those interviews were absolutely loaded with language and words that we still use in our marketing, right? From what, seven, like six years ago now. So that absolute gold mine for the things that came out of those interviews.”
  • “Trying to communicate what we do succinctly… it’s hard to communicate, you know? If I was to advise someone else to do this… I’d ask literally everyone, you know, for ideas basically is what I would say.”
  • “Tell me a story like… Tell me a horror story about the last time you had to chase clients for content… because you hear that same story from a whole bunch of different web designers.”

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