The Entrepreneur's Journey: Balancing Challenges and Fulfillment

Brought to you by LinkedIn Jobs recruitment platform with 1B+ users; Eight Sleep’s Pod Cover sleeping solution for dynamic cooling and heating; and Shopify global commerce platform, providing tools to start, grow, market, and manage a retail business.

Noah Kagan (@noahkagan) was #30 at Facebook, #4 at Mint, and has since created seven million-dollar businesses (Kickflip/Gambit, AppSumo, KingSumo, SendFox, Sumo, TidyCal, and Monthly1k).

He is the CEO of AppSumo.com, the #1 software-deals site for entrepreneurs, and has a popular YouTube channel, Noah Kagan. 

His new book is Million Dollar Weekend: The Surprisingly Simple Way to Launch a 7-Figure Business in 48 Hours.

Please enjoy!

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The blog post for this episode: https://tim.blog/2024/01/23/noah-kagan-million-dollar-weekend/

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This episode is brought to you by Shopify! Shopify is one of my favorite platforms and one of my favorite companies. Shopify is designed for anyone to sell anywhere, giving entrepreneurs the resources once reserved for big business. In no time flat, you can have a great-looking online store that brings your ideas to life, and you can have the tools to manage your day-to-day and drive sales. No coding or design experience required.

Go to shopify.com/Tim to sign up for a one-dollar-per-month trial period. It’s a great deal for a great service, so I encourage you to check it out. Take your business to the next level today by visiting shopify.com/Tim.

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This episode is also brought to you by Eight Sleep! Eight Sleep’s Pod Cover is the easiest and fastest way to sleep at the perfect temperature. It pairs dynamic cooling and heating with biometric tracking to offer the most advanced (and user-friendly) solution on the market. Simply add the Pod Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. It also splits your bed in half, so your partner can choose a totally different temperature.

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This episode is also brought to you by LinkedIn Jobs. Whether you are looking to hire now for a critical role or thinking about needs that you may have in the future, LinkedIn Jobs can help. LinkedIn screens candidates for the hard and soft skills you’re looking for and puts your job in front of candidates looking for job opportunities that match what you have to offer.

Using LinkedIn’s active community of more than one billion professionals worldwide, LinkedIn Jobs can help you find and hire the right person faster. When your business is ready to make that next hire, find the right person with LinkedIn Jobs. And now, you can post a job for free. Just visit LinkedIn.com/Tim.

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[00:00] Start

[03:55] Noah and some of his notable successes.

[07:00] Is Barcelona the new Austin?

[13:43] Navigating the legal hurdles to living/working in another country.

[17:44] Running an $80 million business.

[20:41] Noah’s negotiating basics.

[24:33] The chargeback maneuver.

[27:02] WIIFT (What’s In It For Them?)

[29:54] A recap of the coffee challenge.

[31:31] “Life punishes the vague wish and rewards the specific ask.”

[34:12] Other comfort challenges Noah recommends.

[39:12] Feedback is a gift.

[42:26] When comfort challenges aren’t appropriate.

[45:33] LOT (Listen, Options, Transition).

[46:59] Tracking metrics that matter.

[52:17] T3 B3 (Top Three, Bottom Three).

[59:46] Weekly reviews.

[1:02:42] The value of unambitious goals.

[1:06:51] Regrets of billionaires.

[1:13:32] My approach to book launches: then and now.

[1:26:50] Priorities: then and now.

[1:43:19] Finding a sustainable purpose.

[1:49:42] Do I still find my past work useful today?

[1:52:44] Testing the waters with new hires.

[1:55:22] Don’t forget to look in the rear-view mirror sometimes.

[1:56:23] Why should you trust Noah’s advice in Million Dollar Weekend?

[1:59:47] Now, not how.

[2:03:18] What’s your freedom number?

[2:03:59] Getting your ask in gear.

[2:05:09] Counterintuitively, constraints catalyze creativity.

[2:08:17] Turning annoyance into opportunity.

[2:11:21] Determining if your intended market has value.

[2:14:12] Most profitable, elegant businesses are simple at their core.

[2:14:57] Entrepreneurs rise from the ashes of fired employees.

[2:17:14] Why you should start a podcast or business.

[2:18:18] “No solutions, only trade-offs.”

[2:19:01] Putting the idea to the test.

[2:22:52] Are you making this harder than it needs to be?

[2:24:09] The Dream 10 as a test for market viability — and your commitment.

[2:27:07] Rejection as teacher.

[2:27:58] Deliver on promises before worrying about scaling up.

[2:32:01] The three Ws: what, who, and where?

[2:33:04] The AppSumo origin story.

[2:36:24] Early high-touch community building and scaling considerations.

[2:38:29] The BrainQUICKENing.

[2:42:43] Finding underserved opportunities.

[2:44:48] Initiate correspondence with humility.

[2:48:12] Little ask, big ask.

[2:48:56] How do I handle rejection?

[2:51:18] Revisiting the Law of Category.

[2:56:16] How Noah handled a recent rejection.

[2:57:28] Dating circa now and learning optimism.

[2:59:18] How Pat seized opportunity in Poland.

[3:00:36] Free work?

[3:04:35] Behind the scenes of my Opening the Kimono event.

[3:12:02] Making sponsorship deals win/win.

[3:15:47] Streamlining business idea validation.

[3:19:42] Unorthodox simplicity.

[3:22:02] Better to be chased for money than chasing it.

[3:23:45] Best holiday purchases for under $50.

[3:31:28] Is competing for attention on YouTube worth my time and sanity?

[3:39:55] Low-effort, high-reward YouTube experiments.

[3:45:21] Lessons learned from spending more than a million dollars on coaching.

[3:53:01] Benefits of the board.

[3:53:35] How to take on the 48-hour challenge.

[3:56:00] What’s the DEAL with Cindy 10 years after meeting Noah and me?

[4:00:34] Parting thoughts.

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