424 episodes

Founders, friends and fellow builders Alex Lieberman and Jesse Pujji know what it is to be a founder. The irrational confidence, relentless grind and creative ecstacy needed to build something. In this show, they dole out unfiltered opinions and advice on how to build businesses, and how the current state of the world helps or hurts founders.

The Crazy Ones Morning Brew Podcasts

    • Business
    • 4.7 • 1K Ratings

Founders, friends and fellow builders Alex Lieberman and Jesse Pujji know what it is to be a founder. The irrational confidence, relentless grind and creative ecstacy needed to build something. In this show, they dole out unfiltered opinions and advice on how to build businesses, and how the current state of the world helps or hurts founders.

    Exclusive: Selling My Company & Making Life-changing Money

    Exclusive: Selling My Company & Making Life-changing Money

    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.

    #TheCrazyOnes #Startups #Entrepreneur
    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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    Alex Lieberman (@businessbarista)
    Jesse Pujji (@jspujji)

    Links:


    Jesse’s 2010 Online Lead Generation deck 

    Jesse’s twitter thread after selling Ampush

    Tinuiti Acquires Ampush

    • 1 hr 15 min
    How to Run a Great Off-Site (BONUS EPISODE)

    How to Run a Great Off-Site (BONUS EPISODE)

    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
     
    #TheCrazyOnes #Startups #Entrepreneur
    Watch this episode on YouTube here: https://www.youtube.com/@TheCrazyOnesPod
    Subscribe to Morning Brew!
    Sign up for free today: https://bit.ly/morningbrewyt
    Follow The Brew!
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    Follow Our Hosts!
    Alex Lieberman (@businessbarista)
    Jesse Pujji (@jspujji)
    #TheCrazyOnes #Startups #Entrepreneur

    Subscribe to Morning Brew!
    Sign up for free today: https://bit.ly/morningbrewyt

    • 9 min
    Jonathan Swanson on Building a Unicorn and Delegating 90% of Your Life

    Jonathan Swanson on Building a Unicorn and Delegating 90% of Your Life

    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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    YouTube - https://www.youtube.com/@TheCrazyOnesPod

    Follow Our Hosts!
    Alex Lieberman (@businessbarista)
    Jesse Pujji (@jspujji)

    • 53 min
    How an Entrepreneur Turns Self-Hate into Love

    How an Entrepreneur Turns Self-Hate into Love

    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

    Subscribe to Morning Brew!
    Sign up for free today: https://bit.ly/morningbrewyt
    Follow The Brew!
    Instagram - https://www.instagram.com/morningbrew/
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    Follow Our Hosts!
    Alex Lieberman (@businessbarista)
    Jesse Pujji (@jspujji)

    Links: 
    Alex’s tweet on 8 self-hating beliefs

    • 38 min
    Our 2023 Predictions, from AI to the Creator Economy

    Our 2023 Predictions, from AI to the Creator Economy

    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

    Subscribe to Morning Brew!
    Sign up for free today: https://bit.ly/morningbrewyt
    Follow The Brew!
    Instagram - https://www.instagram.com/morningbrew/
    Twitter - https://twitter.com/MorningBrew
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    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?

    Links:

    Pebblely AI

    Paul Fairie’s tweet about predictions for 2023

    • 55 min
    Co-founders Austin Rief and Alex Lieberman on Building Morning Brew

    Co-founders Austin Rief and Alex Lieberman on Building Morning Brew

    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

    Subscribe to Morning Brew!
    Sign up for free today: https://bit.ly/morningbrewyt
    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)
    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

    Links:
    Chop It Off (Neal Freyman)

    • 1 hr

Customer Reviews

4.7 out of 5
1K Ratings

1K Ratings

AFbuilder ,

Keep up the great work

I listen to a lot of business and entrepreneurship podcasts and this is one of the best ones out there.

The segment on the latest episode pitching and analyzing the plunge business was awesome. More of that please. More pitches from founders and follow ups to see how they inevitability pivot and evolve.

Fun hosts and good insights! ,

Brilliant thinkers and doers

I’ve followed the three hosts on Twitter for a while and regularly go to their profiles and read their content cause they’re smart individuals.

Now I can hear them riff and chat? I’m in

jaysip ,

New favorite podcast

Very useful and also very real.

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