
182: Daniel Fayle — Door-to-door to $2M ARR
The Bootstrapped Founder
01/18/23
•53m
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Today, I’m talking to Daniel Fayle — co-founder of Chekkit, a business he and his team have boostrapped to $2mil in ARR. We’ll touch on finding the right vertical to get started, how to do things that don’t scale, and what choices need to be made to get a business to 7 figures.
00:00:00 Daniel Fayle
00:05:35 Getting started with Chekkit
00:09:00 Local marketing & picking verticals
00:12:05 When to hire a team?
00:17:25 Integrations
00:22:33 Pricing choices
00:25:32 How to be inspired by competition?
00:29:54 The importance of customer support
00:36:31 Setting limits on free trials
00:41:55 Use the tech that your customers use
00:47:15 How to stay on top of your game
- Door-to-door to $2M ARR with Daniel Fayle
- Find your Following, my Twitter course — now with Find your Following Essentials, the 7-day Twitter crash course
- Zero to Sold & The Embedded Entrepreneur, my books on entrepreneurship
This episode is sponsored by MicroAcquire.
Previous Episode

181: The Role of Trust in Remote Work
January 13, 2023
•11m
I was chatting with Marissa Goldberg about remote work this week, and she gave me several handy frameworks for founders who want to build remote-first businesses. At the center of any successful remote work relationship lies trust.
And surprisingly, many businesses have a tough time trusting anyone once they can't see them at their desk in the office. Remote work is throwing a wrench in the time-honored tradition of butt-in-seat-hands-on-keyboard that so many managers consider to be the pinnacle of productivity.
Remote work does away with this.
00:00:00 Remote Work is Here to Stay
00:01:28 Async is the New Default
00:04:42 The Deep Work Zone
00:06:17 Trust and Having Nowhere to Hide
- The Role of Trust in Remote Work - Find your Following, my Twitter course — now with Find your Following Essentials, the 7-day Twitter crash course
- Zero to Sold & The Embedded Entrepreneur, my books on entrepreneurship
Next Episode

183: Expanding Your Opportunity Surface
January 20, 2023
•12m
To increase your chances of success as an entrepreneur, think outside the box and expand your opportunity surface. This can be achieved by embracing activities that don't scale, diversifying inputs, and taking small steps toward achieving your goals. These strategies will help you create valuable connections, build strong relationships and gain valuable insights that will lead to success.
- Expanding Your Opportunity Surface
- Find your Following, my Twitter course — now with Find your Following Essentials, the 7-day Twitter crash course
- Zero to Sold & The Embedded Entrepreneur, my books on entrepreneurship
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