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How to Crush Investor Updates Feb 09, 2023

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Episode 22: In this episode of The Crazy Ones, host Alex Lieberman (@businessbarista) is walking you through why, when, and how to craft the perfect investor update, complete with advice from some very experienced investors.

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Listen to The Crazy Ones here: https://link.chtbl.com/OV4W93_W

Watch The Crazy Ones here: https://www.youtube.com/@TheCrazyOnesPod

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How One Author Raised $41M on Kickstarter Feb 07, 2023

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Episode 21: Today, hosts Alex Lieberman (@businessbarista) and Jesse Pujji (@jspujji) are getting into all things crowdfunding. Alex has decided to create a Kickstarter campaign for his new business, The Plunge, and is learning a lot in the process—from the secrets behind the most successful Kickstarter campaigns in history, to knowing how and when to pursue crowdfunding. Listen to hear Alex share what he’s learned about crowdfunding, and Jesse’s opinions on Alex’s approach to launching The Plunge.

#TheCrazyOnes #Startups #Entrepreneur #Kickstarter

Watch The Crazy Ones here: https://www.youtube.com/@TheCrazyOnesPod

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How to Build Your Second Brain (BONUS EPISODE) Feb 02, 2023

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Episode 20: In this special bonus episode of The Crazy Ones, host Alex Lieberman (@businessbarista) is telling you everything you need to know about personal knowledge management. That’s right, Alex is breaking down and summarizing what he’s learned in a recent course he took called Building a Second Brain, all about knowledge management and how to make the most effective use of the information you consume.

#TheCrazyOnes #Startups #Entrepreneur

Watch The Crazy Ones here: https://www.youtube.com/@TheCrazyOnesPod

(00:00) - Intro

(01:18) - Episode rundown

(01:36) - What Personal Knowledge Management is

(03:35) - Why it’s worth considering creating a Personal Knowledge Management system

(05:42) - The essential building block of building a second brain: CODE

(07:28) - How Alex is applying CODE to the launch of his backyard game, The Plunge

(10:35) - Explaining the organizational strategy of PARA

(18:56) - Why it’s worth building a second brain

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Exclusive: Selling My Company & Making Life-Changing Money Jan 31, 2023

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Episode 19: Today, hosts Alex Lieberman (@businessbarista) and Jesse Pujji (@jspujji) are breaking down the recent sale of Jesse’s first business, Ampush. From building the company in the early days, to making the decision to sell, to the actual negotiations and the emotional aftermath, Jesse and Alex dig into all of it.

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Watch The Crazy Ones here: https://www.youtube.com/@TheCrazyOnesPod

(00:46) - Intro

(04:50) - How Tinuity came to acquire Jesse’s company, Ampush

(07:20) - The creation and growth of Ampush

(18:43) - The first time Ampush tried to sell

(24:35) - What led Jesse to transition out as Ampush’s CEO

(30:04) - What drove the more recent decision to sell Ampush

(32:41) - What the process of selling Ampush looked like

(43:44) - What Jesse prioritized when negotiating the sale of Ampush

(49:53) - The emotional experience of selling Ampush

(1:02:25) - The importance of having a supportive partner in the entrepreneurial journey

(1:06:05) - Why the sale has made Jesse feel successful

(1:08:03) - How Jesse thinks about raising his kids now that he’s reached a certain level of success

(1:10:51) - What’s next for Jesse

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How to Run a Great Off-Site (BONUS EPISODE) Jan 26, 2023

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Episode 18: Today, host Jesse Pujji (@jspujji) is bringing you a special bonus episode addressing a frequently asked question—how do you run a great team off-site? Listen to hear Jesse break down the fundamentals of running an impactful off-site with your team—from effective preparation, to what types of strategy sessions to hold, to the best team-bonding exercises.

(00:00) - Intro

(00:29) - Why you run an off-site

(01:24) - How to run an effective strategic off-site

(05:14) - What makes for a great off-site beyond strategy

(6:00) - Bonding games and exercises

(07:11) - Important things to keep in mind when preparing for your off-site

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Watch this episode on YouTube here: https://www.youtube.com/@TheCrazyOnesPod

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Jonathan Swanson on Building a Unicorn and Delegating 90% of Your Life Jan 24, 2023

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Episode 17: Today, hosts Alex Lieberman (@businessbarista) and Jesse Pujji (@jspujji) are joined by fellow startup entrepreneur Jonathan Swanson. Jonathan is the co-founder and chairman of Thumbtack—a massive technology leader building the modern home management platform. In this episode, Jonathan tells Alex and Jesse all about how he and his co-founders came up with the idea for Thumbtack, the turning points and oh-sh*t moments of growing the business, and his genius delegation tactics that save him hundreds of hours over the course of a year.

Time Mapping:

(00:50) - Intro

(01:51) - Start of Jonathan Swanson interview

(04:04) - What keeps Jonathan motivated, even after all of his career success

(05:21) - Jonathan Swanson’s upbringing and background

(06:20) - Why Jonathan decided to pursue entrepreneurship

(09:23) - The early days of starting Thumbtack

(15:48) - The moment that changed everything for Thumbtack

(17:09) - How Jonathan navigates his co-founder relationship

(22:00) - The event that almost killed Thumbtack

(27:00) - The overseas employee that changed Jonathan’s trajectory

(30:20) - Jonathan’s career path after Thumbtack

(33:40) - Jonathan’s tips for how to delegate as a leader

(41:21) - Jonathan’s other businesses

(45:00) - How Jonathan hacks his personal life

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How an Entrepreneur Turns Self-Hate into Love Jan 17, 2023

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Episode 16: Today, hosts Alex Lieberman (@businessbarista) and Jesse Pujji (@jspujji) discuss some of the highly self-critical beliefs Alex has been reflecting on as a founder, and how he’s learned to reframe them for himself.

#TheCrazyOnes #Startups #Entrepreneur

Listen to The Crazy Ones here: https://link.chtbl.com/OV4W93_W

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Alex’s tweet on 8 self-hating beliefs

Our 2023 Predictions, from AI to the Creator Economy Jan 10, 2023

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Episode 15: Today, hosts Alex Lieberman (@businessbarista) and Jesse Pujji (@jspujji) are talking about their predictions in the business world for 2023—from generative AI, to content creation, what will happen with Twitter (of course), and so much more. Then, Alex gets Jesse’s advice on the launch plan of his new lawn game, The Plunge. And finally, we wrap the episode with a question around recurring meetings—do they ADD value to a business’s operations, or do they do the opposite?

#TheCrazyOnes #Startups #Entrepreneur

Listen to The Crazy Ones here: https://link.chtbl.com/OV4W93_W

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Follow The Brew!

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Tik Tok - https://www.tiktok.com/@morningbrew

Follow Our Hosts!

Alex Lieberman (@businessbarista)

Jesse Pujji (@jspujji)

(00:32) - Intro

(02:39) - The Rundown

(03:45) - Predictions for 2023

(04:48) - Jesse’s predictions around AI for 2023

(09:02) - Alex’s predictions for 2023

(21:52) - The potential of the creator economy

(25:48) - Alex’s prediction for Twitter

(26:09) - Alex’s prediction for Pickleball

(27:59) - Alex’s TikTok prediction

(30:33) - Predictions made in 1923 about 2023

(33:18) - How Alex came up with the concept for his lawn game, The Plunge

(36:18) - Alex’s pitch for his new business

(40:03) - The production challenge Alex has discovered in the process of building The Plunge

(41:06) - Alex’s ethos around launch

(43:56) - Alex’s marketing plan for The Plunge

(49:53) - The big questions Alex has right now around launching The Plunge

(51:35) - Startup AMA: Recurring meetings—are they good or bad?

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Co-founders Austin Rief and Alex Lieberman on Building Morning Brew Jan 03, 2023

Show notes

Episode 14: To kick off the new year, host Alex Lieberman (@businessbarista) is bringing you a very special episode of The Crazy Ones featuring Morning Brew Co-Founder and CEO Austin Rief (@Austin_Rief) and special guest Sahil Bloom (@SahilBloom). In this conversation moderated by Sahil, Austin and Alex recount the early days of building Morning Brew, the scrappy ways they grew their subscriber base, and the biggest mistakes and lessons learned along the way.

#TheCrazyOnes #Startups #Entrepreneur

Listen to The Crazy Ones here: https://link.chtbl.com/OV4W93_W

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Follow The Brew!

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Alex Lieberman (@businessbarista)

Jesse Pujji (@jspujji)

(00:51) - Intro

(02:25) - How Austin and Alex handled the doubters early on in creating Morning Brew

(07:18) - What Austin and Alex imagined their careers would be prior to starting Morning Brew

(11:03) - How Austin and Alex met

(16:39) - How Austin got involved with Alex’s newsletter

(19:48) - How the original newsletter looked in its first iteration

(21:06) - What allowed for Morning Brew to be successful in the early days

(27:46) - The scrappiest tactics Alex and Austin used to grow the newsletter readership early on

(33:40) - The marketing strategy that continues to shape how Alex and Austin approach the business today

(36:40) - How Alex and Austin scaled voice as Morning Brew grew

(40:20) - What sealed the deal for Alex and Austin to hire the current managing editor

(43:44) - The biggest mistakes that Austin and Alex made along the way

(47:47) - What led to Alex deciding to step down as CEO and Austin becoming CEO

(52:19) - Alex and Austin answer whether success and wealth has made them happier

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Chop It Off (Neal Freyman)

Building a Multimillion Dollar Business…By Yourself Dec 27, 2022

Show notes

Episode 13: Today, hosts Alex Lieberman (@businessbarista), Sophia Amoruso (@sophiaamoruso), and Jesse Pujji (@jspujji) are talking solo-preneurship—aka running a business of one. What are the pros and cons of being a solo-preneur? And what types of businesses is solo-preneurship best suited for? Then, the team gets radically honest about how they spend their time each week—from self-care to deep work, Jesse, Alex, and Sophia break down how many hours per week they dedicate to work and play, and how they organize their schedules.

And finally, the team wraps the last episode of the year with a brainstorm of how we can improve on the show. We’d love to hear your feedback too! Email us at thecrazyones@morningbrew.com.

#TheCrazyOnes #Startups #Entrepreneur

Listen to The Crazy Ones here: https://link.chtbl.com/OV4W93_W

Subscribe to Morning Brew!

Follow The Brew!

Instagram - https://www.instagram.com/morningbrew/

Twitter - https://twitter.com/MorningBrew

Tik Tok - https://www.tiktok.com/@morningbrew

Follow Our Hosts!

Alex Lieberman (@businessbarista)

Sophia Amoruso (@sophiaamoruso)

Jesse Pujji (@jspujji)

(00:34) - Intro

(00:58) - The Rundown

(02:35) - Why Jesse would hate running a business of one

(05:07) - Sophia’s point of view on running a business of one

(07:01) - When running a business of one can become challenging

(08:25) - The actual popularity of solo-preneurship

(10:04) - The story of Pieter Levels attempting to start 12 startups in 12 months

(17:29) - Start of the conversation about how the team spends their time

(18:23) - How Sophia organizes her week

(22:48) - How Sophia organizes her time to allow for the context-switching she has to do every week

(24:09) - How Jesse approaches organizing his time

(28:32) - The scheduling mistake Jesse sees early founders making

(29:23) - How Jesse carves out time for deep work during the week

(33:00) - How Alex spends his time

(36:59) - The team brainstorm about how to improve the show

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