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I sat down with Will Cannon again and we talked about how he went from scraping and selling lead lists to building multiple million-dollar SaaS businesses. We covered his early background, losing everything in 2008, and how that pushed him into B2B data, cold email, and eventually software.
We broke down how he built a profitable lead-selling agency with almost no upfront costs, why recurring revenue changed everything, and how UpLead got its first customers. Will also shared how he thinks about copying existing businesses, acquiring customers before building, and why you do not need to be technical to make this work.
Will shares his free playbooks and his socials at IAmWillCannon.com
Get Will’s Free Cold Email Playbook: https://iamwillcannon.com/free-resources/the-cold-email-playbook
Want to copy Will's system? He gives away his entire strategy (scripts included) in this episode: https://open.spotify.com/episode/1YmJsHESukCo2i9YS9xNMD?si=DDT_jlpeRviFBe7lr4KNKA
Enjoy!
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Watch this on YouTube instead here: tkopod.co/p-yt
Ask me a question on or off the show here: http://tkopod.co/p-ask
Learn more about me: http://tkopod.co/p-cjk
Learn about my company: http://tkopod.co/p-cof
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Free weekly business ideas newsletter: http://tkopod.co/p-nl
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Scrape small business data: http://tkopod.co/p-os
---
Join my AI Consulting Community (PlaymakersAI):https://playmakersai.com/
Check out my newsletter at https://TKOPOD.com and join my new community at https://TKOwners.com
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If you are new here from the Diary of a CEO episode, welcome. I am really glad you are here. And for everyone who has been with me from the beginning, I appreciate you more than you know.
In this episode I took all 254 past episodes and pulled out the very best ideas, lessons, guests and takeaways so you do not have to go back and binge everything unless you want to. I walk through my top 23 episodes and rank them from 23 to 1. You will hear why these ideas work, what I love about them, where people get stuck, and how you can use them no matter how much money or experience you have.
If you are new to my world, this is the perfect starting point because it gives you the full overview of the most tactical and approachable business ideas we have ever covered. If you have been listening for a while, this is a great refresh and a fun look back at what has actually changed people’s lives.
Rank 23
Episode 55. How to Start a Six Figure Side Hustle Exclusively on Facebook Marketplace
Rank 22
Episode 229. Starting a Drone Business and Drone Roof Inspections
Rank 21
Episode 226. Domain Name Investing
Rank 20
Episode 239. Laundromats with Tyler Purcell
Rank 19
Episode 210. Etsy Print on Demand
Rank 18
Episode 73. Porch Pumpkins
Rank 18
Episode 186. Mailbox Repair
Rank 17
Episode 196. Forestry Mulching
Rank 16
Episode 162. Lessons Learned from Starting 75 Plus Businesses
Rank 15
Episode 170. How to Get a Yes from Everyone
Rank 14
Episode 175. Hummingbird Food E Commerce Brand
Rank 13
Episode 144. How to Get Everything You Want Out of Life
Rank 12
Episode 207. Which AI Should You Use to Make Money
Rank 11
Episode 233. Beginner Friendly Ways of Making 10 Grand
Rank 10
Episode 228. Three Million a Year from Tiny AI Tools
Rank 9
Episode 203. How to Make a Million Dollars in Six Months
Rank 8
Episode 230. How to Copy Businesses and White Label Them with Go High Level
Rank 7
Episode 205. The Most Overlooked Business Idea You Have Ever Heard Of
Rank 6
Episode 248. Eight Ideas for You to Start This Weekend
Rank 5
Episode 169. Twenty Five Tips Tools and Tricks to Use ChatGPT
Rank 4
Episode 161. How to Start an Ad Agency with AI Video Generation
Rank 3
Episode 156. Reselling Liquidation Items
Rank 2
Episode 164. Directories
Rank 1
Episode 204. I Started an Online Business in 56 Minutes
Enjoy!
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Watch this on YouTube instead here: tkopod.co/p-yt
Ask me a question on or off the show here: http://tkopod.co/p-ask
Learn more about me: http://tkopod.co/p-cjk
Learn about my company: http://tkopod.co/p-cof
Follow me on Twitter here: http://tkopod.co/p-x
Free weekly business ideas newsletter: http://tkopod.co/p-nl
Share this podcast: http://tkopod.co/p-all
Scrape small business data: http://tkopod.co/p-os
---
Check out my newsletter at https://TKOPOD.com and join my new community at https://TKOwners.com
━
Quick update before you dive in. We’re shifting our upload schedule from three times a week to two. Instead of Mo-Wed-Fri, we’ll now be posting every Tuesday and Friday. With all the new formats we’re producing, three a week became tough to keep at the level we want. This new cadence will help us keep the quality high.
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A year ago I interviewed Cinco about his line striping business. That episode is here: https://open.spotify.com/episode/6xd6KRw895dstoagycodp5?si=SE8Zssb_SvGNToYYHWazUQ
Hunter heard it, got inspired, and nine weeks later he had nearly fifty thousand dollars in revenue with zero experience.
I sat down with Hunter Schenewark to break down how he made almost fifty thousand dollars in his first nine weeks with a simple striping and seal coating business. He had zero experience, started in a small town, did his first job for free in a local Facebook group, then used cold email to land big church projects. We walk through how he priced jobs, how he found customers, the equipment he bought, what it cost, and why seal coating became the real money maker.
Hunter on X
https://x.com/HSchenewark
Hunter’s website
https://417striping.com
Enjoy!
---
Watch this on YouTube instead here: tkopod.co/p-yt
Ask me a question on or off the show here: http://tkopod.co/p-ask
Learn more about me: http://tkopod.co/p-cjk
Learn about my company: http://tkopod.co/p-cof
Follow me on Twitter here: http://tkopod.co/p-x
Free weekly business ideas newsletter: http://tkopod.co/p-nl
Share this podcast: http://tkopod.co/p-all
Scrape small business data: http://tkopod.co/p-os
---
Check out my newsletter at https://TKOPOD.com and join my new community at https://TKOwners.com
━
Quick update before you dive in. We’re shifting our upload schedule from three times a week to two. Instead of Mo-Wed-Fri, we’ll now be posting every Tuesday and Friday. With all the new formats we’re producing, three a week became tough to keep at the level we want. This new cadence will help us keep the quality high.
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I sat down with Will Cannon to break down how cold email really works today. Will has sent over one hundred million cold emails and grew one of his companies to a million dollars ARR almost entirely from it. We talk about how to write short emails that convert, how many follow ups you actually need, how to build a list, and what works right now for getting your first customer fast.
Will shares his free playbooks and his socials at IAmWillCannon.com
Get Will’s Free Cold Email Playbook: https://iamwillcannon.com/free-resources/the-cold-email-playbook
Enjoy!
---
Watch this on YouTube instead here: tkopod.co/p-yt
Ask me a question on or off the show here: http://tkopod.co/p-ask
Learn more about me: http://tkopod.co/p-cjk
Learn about my company: http://tkopod.co/p-cof
Follow me on Twitter here: http://tkopod.co/p-x
Free weekly business ideas newsletter: http://tkopod.co/p-nl
Share this podcast: http://tkopod.co/p-all
Scrape small business data: http://tkopod.co/p-os
---
Check out my newsletter at https://TKOPOD.com and join my new community at https://TKOwners.com
━
Beehiiv is the newsletter platform I’ve used for over a year and a half because their data shows you exactly what’s working. Get 30% off three months at beehiiv.com/chris
And right now, for Black Friday, you can use Promo Code: 2025BFCM for 20% off any annual plan.
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Quick update before you dive in. We’re shifting our upload schedule from three times a week to two. Instead of Mo-Wed-Fri, we’ll now be posting every Tuesday and Friday. With all the new formats we’re producing, three a week became tough to keep at the level we want. This new cadence will help us keep the quality high.
I sat down with Connor Gross ( https://x.com/c_gro ) in New York and we went deep on one simple idea taking proven products and changing the form factor to unlock ridiculous upside. We talk about how Billy Mays, OxiClean, and late night infomercials turned into today’s DTC and TikTok style direct response, then riff on everything from “AG1 in a gummy” and brands like Grüns, Starface pimple stickers, and stain remover stickers for kids clothes, all the way to race day temporary tattoos that show your elevation profile and aid stations. From there we get into filtration for cyclists and runners, mouth tape for performance and pollution, third party testing apps like SuppCo and Seed Oil Scout, and the crazy opportunity in being the trusted auditor for supplements, snacks, and food labels. We wrap by talking about city based silent retreat concepts inspired by OtherShip, how to productize attention and stillness in a noisy world, and why there is so much money sitting in boring categories if you are willing to innovate on packaging, distribution, and trust.
Enjoy!
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Watch this on YouTube instead here: tkopod.co/p-yt
Ask me a question on or off the show here: http://tkopod.co/p-ask
Learn more about me: http://tkopod.co/p-cjk
Learn about my company: http://tkopod.co/p-cof
Follow me on Twitter here: http://tkopod.co/p-x
Free weekly business ideas newsletter: http://tkopod.co/p-nl
Share this podcast: http://tkopod.co/p-all
Scrape small business data: http://tkopod.co/p-os
---