DiscoverFounder's Journal
Founder's Journal
Author: Morning Brew
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© 2022 Morning Brew Inc
Description
Alex Lieberman, the co-founder and Executive Chairman of Morning Brew, gives you an insider’s look into building businesses. Alex explores the founder’s journey, from the painful challenges of 0-to-1 to the powerful frameworks that help you scale to millions in revenue as well as the emotional rollercoaster that is present throughout.
602 Episodes
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It’s the season finale! We’re taking time to reflect on this year’s biggest learnings and answer some final audience questions. From insights on financial wellness for women to AI’s influence on the financial landscape, we’re touching on topics that can have a big impact on your portfolio.
Options trading entails significant risk and is not appropriate for all investors. Certain complex options strategies carry additional risk. Before trading options, please read Characteristics and Risks of Standardized Options. Supporting documentation for any claims, if applicable, will be furnished upon request.
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Volatile markets and inflation are top of mind for investors. We kick off season 4 by exploring the current economic and financial landscape and the tools investors can use to navigate it.
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Episode 24: In this episode of The Crazy Ones, host Jesse Pujji (@jspujji) is sharing his seven biggest takeaways from launching GrowthAssistant, which celebrated its 2-year anniversary on February 10th. Listen to hear Jesse share some really sage advice on what to keep in mind when starting a new business.
#TheCrazyOnes #Startups #Entrepreneur
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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Links:
Jesse’s tweet
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Episode 23: Today, hosts Alex Lieberman (@businessbarista) and Jesse Pujji (@jspujji) are discussing product-market fit: how to find it, what to do when you don’t have it, and just how much you should actually worry about it. Then, Jesse and Alex jump into a discussion about billionaire Sir Richard Branson and his illustrious entrepreneurial career, his approach to starting new businesses that has made him so successful, and what we entrepreneurs can learn from his story.
#TheCrazyOnes #Startups #Entrepreneur
Listen to The Crazy Ones here: https://link.chtbl.com/OV4W93_W
Watch The Crazy Ones here: https://www.youtube.com/@TheCrazyOnesPod
(00:57) - Intro
(04:55) - The Rundown
(05:29) - Finding product-market fit
(16:00) - How Jesse re-directed his approach after Kahani didn’t have clear product-market fit
(22:57) - How Jesse approaches the problem when you don’t have a perfect market or economy for launching your product
(28:50) - Why Jesse thinks no one should overly concern themselves with product-market fit
(32:28) - Key tips for finding product-market fit
(33:45) - The Richard Branson story
(44:22) - How Richard Branson thinks about starting new businesses, and his holding company
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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.
#TheCrazyOnes #Startups #Entrepreneur
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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Links:
Alex’s investor update tweet
Daniel Gross’s investor update resource
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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
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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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Links:
Tiago Forte’s blog
https://www.buildingasecondbrain.com/
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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.
#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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Links:
Jesse’s 2010 Online Lead Generation deck
Jesse’s twitter thread after selling Ampush
Tinuiti Acquires Ampush
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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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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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(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)
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Episode 12: Today, hosts Alex Lieberman (@businessbarista), Sophia Amoruso (@sophiaamoruso), and Jesse Pujji (@jspujji) brainstorm some brilliant ideas for making extra $$ in the new year, as well as how to come up with your own side hustle concepts. Then, the team gets deep with a discussion on year-end reflection and how they set goals and intentions for the coming year. And finally, we wrap with a fascinating Startup AMA addressing when and how to approach buying a domain.
#TheCrazyOnes #Startups #Entrepreneur
Listen to The Crazy Ones here: https://link.chtbl.com/OV4W93_W
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Sophia Amoruso (@sophiaamoruso)
Jesse Pujji (@jspujji)
(00:22) - Intro
(00:58) - The Rundown
(03:12) - How the team defines a side hustle
(04:36) - How accurate the portrayal of Sophia’s story is on Netflix’s Girlboss
(07:01) - Sophia’s view on side hustles
(09:58) - Alex’s side hustle ideas
(15:23) - Jesse’s side hustle ideas
(18:20) - What many people don’t consider about side hustles
(24:08) - How Jesse approaches year-end reflection
(27:58) - How Sophia approaches reflecting at the end of the year
(30:07) - How Alex approached year-end reflection this year
(34:12) - The trick that helps Jesse stick with his New Year’s resolutions
(39:14) - Startup AMA: Buying Domain Names
(42:03) - How Jesse made 5-figures from selling a domain
(43:21) - What went wrong with Sophia’s domain name purchase
(45:22) - When it does, and does NOT make sense to spend $$ on buying a domain name
Links:
https://microacquire.com/
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Episode 11: Today, hosts Alex Lieberman (@businessbarista), Sophia Amoruso (@sophiaamoruso), and Jesse Pujji (@jspujji) are talking about the brilliance behind airline rewards programs, and other genius ways that businesses have found to get extra cash out of their partners and customers. Then, the team talks end-of-year planning for your business and how to determine which goals and metrics to work towards in the new year. And finally, the team answers a Startup AMA question addressing the biggest misconceptions around founders.
#TheCrazyOnes #Startups #Entrepreneur
Listen to The Crazy Ones here: https://link.chtbl.com/OV4W93_W
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Sophia Amoruso (@sophiaamoruso)
Jesse Pujji (@jspujji)
(00:28) - Intro
(01:12) - The Rundown
(01:55) - The genius of airline loyalty programs
(02:58) - Blue Chip Stamps - one of the early loyalty programs
(07:09) - How airline loyalty programs work to be so profitable
(13:40) - How Starbucks profits from its app ordering system
(16:17) - Why it’s important as a business builder to think about getting cash earlier in the cycle of a transaction
(21:20) - How Jesse goes about end-of-year planning for his business
(30:09) - How to think about end-of-year planning in a way that incorporates your personal goals
(34:44) - The Entrepreneurial Operating System (EOS) used at Morning Brew
(40:21) - Startup AMA: What are the biggest myths or misconceptions that people have about startup founders?
Links:
Airline Loyalty Programs: Main Aspects, Types, and a Technological Perspective
How Airlines Make Billions From Monetizing Frequent Flyer Programs
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Episode 10: The team is back together again! Today, hosts Alex Lieberman (@businessbarista), Sophia Amoruso (@sophiaamoruso), and Jesse Pujji (@jspujji) discuss the marketing brilliance of Spotify Wrapped and all that makes it a mega success, as well as how other companies can try to replicate it. Then, the team dives into selling your business—when, how, and why to do it, what the process is ACTUALLY like, and their biggest takeaways from their own experiences. And finally, we wrap with a game of Thumbs Up/Thumbs Down, in which the team weighs in on some news-related hot takes.
#TheCrazyOnes #Startups #Entrepreneur
Listen to The Crazy Ones here: https://link.chtbl.com/OV4W93_W
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Sophia Amoruso (@sophiaamoruso)
Jesse Pujji (@jspujji)
(00:33) - Intro
(01:54) - The Rundown
(02:28) - Quick history of Spotify Wrapped
(03:03) - Jesse’s Spotify Wrapped
(04:50) - Sophia’s Spotify Wrapped
(07:20) - Alex’s Spotify Wrapped
(08:32) - What makes Spotify Wrapped so successful
(12:58) - The rumored origin story of Spotify Wrapped
(14:43) - The team brainstorms how to apply the lessons from Spotify Wrapped to your their own businesses
(22:27) - Jesse’s experience of the process selling a business
(28:37) - Why Alex and Austin decided to sell Morning Brew, and what Alex thinks about the reasons to sell a business
(33:06) - Sophia’s experience of selling Girlboss
(34:05) - What Sophia potentially could have made on selling Nasty Gal
(35:33) - Why it’s okay to sell a business when you’re early in your career
(37:45) - The grueling nature of the process of selling your business
(42:01) - The one thing Jesse, Sophia, and Alex would do differently if they were re-doing the sales of their business
(44:34) - Thumbs Up/Thumbs Down
Links:
Spotify Wrapped this year
Sophia’s top Spotify songs
Jesse’s top Spotify song
Alex’s top Spotify song
Elad Blog - 5 Reasons to Sell Your Startup
Justin Kan - The Founder’s Guide To Selling Your Company
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Episode 8: Today, host Alex Lieberman (@businessbarista) is solo again for another special episode of The Crazy Ones, this time featuring founder and CEO of 1-800-GOT-JUNK and 02E Brands, Brian Scudamore (@BrianScudamore). Brian bought a used truck and started 1-800-GOT-JUNK in 1989 as a college dropout. Today, 1-800-GOT-JUNK makes $600 million in revenue, and Brian has also created the parent company 02E Brands which brings in an addition $100 million with its other businesses. Listen to hear Brian explain how he grew 1-800-GOT-JUNK from the ground up with a mixture of brilliant publicity tactics and smart hiring, as well as how Brian thinks about his role as a leader as his company grows.
#TheCrazyOnes #Startups #Entrepreneur
Listen to The Crazy Ones here: https://link.chtbl.com/OV4W93_W
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Sophia Amoruso (@sophiaamoruso)
Jesse Pujji (@jspujji)
00:43 - Intro
03:12 - How Brian started 1-800-GOT-JUNK
05:37 - 02E Brands’ reach and annual revenue
06:40 - Brian’s passion and what keeps him motivated
10:50 - How Brian got onto the Ellen Degeneres Show
14:37 - Brian’s opinion on PR to promote your business
16:20 - Brian’s decision to lay off his whole team in 1994
19:23 - Why Brian places a high importance on hiring for culture fit
21:44 - The most important decisions Brian made to allow his business to grow
25:54 - How 02E’s brand franchising works
29:53 - How Brian determined the price of services for 1-800-GOT-JUNK
32:07 - The systems Brian implements so that his ADD doesn’t derail him
34:48 - How Brian’s management of the business has changed as the company has grown
41:13 - Brian’s transition to being less hands-on with the day-to-day operations as his company grew
42:48 - Startup AMA: How do you think about what to do with the cashflow of your business?
Links:
WTF book
BYOB: Build Your Own Business, Be Your Own Boss
The E-Myth Revisited
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Episode 8: Today, host Alex Lieberman (@businessbarista) is flying solo for a very special episode of The Crazy Ones featuring founder and private equity investor Codie Sanchez (@codie_sanchez). Codie has made millions from buying boring businesses (think laundromats, carwashes, and AirBnBs), and has also amassed an audience of over 3 million followers with her media company, Contrarian Thinking. Listen to hear Codie tell Alex about how to determine which boring businesses are actually worth investing in, how to hire good operators, and the art of deal structuring and negotiation.
#TheCrazyOnes #Startups #Entrepreneur
Listen to The Crazy Ones here: https://link.chtbl.com/OV4W93_W
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Sophia Amoruso (@sophiaamoruso)
Jesse Pujji (@jspujji)
00:44 - Intro
01:40 - The Rundown
03:13 - How Codie got to where she is today
06:08 - The first boring business Codie bought
10:30 - What lessons Codie has learned around deal-structuring and negotiation
18:09 - The best negotiations Codie has ever done
21:45 - What makes a great operator for your boring business
23:52 - How Codie scares away a bad hire
26:05 - What boring businesses are catching Codie’s eye right now
33:22 - Why Codie is fascinated with Reese Witherspoon’s business model
36:59 - Why Codie decided to dive deep into content creation
46:10 - How Codie’s boring businesses compare with her media business
48:15 - What Codie has learned about leadership
50:38 - Codie’s hot takes and spiky opinions
Links:
Contrarian Thinking Newsletter
Codie Sanchez YouTube Channel
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Episode 7: Today, hosts Alex Lieberman (@businessbarista), Sophia Amoruso (@sophiaamoruso), and Jesse Pujji (@jspujji) recount the wild story of how the digital media company Red Ventures bootstrapped its way to becoming a business with an $11 billion valuation. Then, the crew dives into fundraising—when to do it, how to set your goals, and their best advice for how to raise most successfully. And finally, the crew answers a Startup AMA question around how find the most attractive benefits packages at the best rates as a small company.
#TheCrazyOnes #Startups #Entrepreneur
Listen to The Crazy Ones here: https://link.chtbl.com/OV4W93_W
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00:33 - Intro
02:02 - The Rundown
03:15 - The story of Ric Elias and Red Ventures
08:09 - Ric’s life-changing experience
08:51 - How Red Ventures’ growth started to take off
12:10 - Red Ventures’ great work culture
13:29 - Jesse’s biggest takeaways from working with Red Ventures
15:38 - How Ric Elias spends his time
24:16 - Sophia’s experience of fundraising and her biggest lessons learned
30:51 - What kind of businesses should raise money vs shouldn’t?
36:29 - Sophia’s advice for founders looking to raise capital right now
37:05 - Jesse’s advice for founders looking to raise capital right now
37:37 - Alex’s advice for founders looking to raise capital right now
37:58 - Startup AMA - How do startups get attractive benefits packages at competitive rates before they get a large headcount?
Links:
Ric Elias TED Talk
You’ve Never Heard of the Biggest Digital Media Company in America
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Episode 6: Today, hosts Alex Lieberman (@businessbarista), Sophia Amoruso (@sophiaamoruso), and Jesse Pujji (@jspujji) break down the hype behind Generative AI—what is it, how it’s being used right now, and how to think about it as a business builder. Then, the team discusses their personal experiences with using executive coaches and why it is or isn’t worth the money. And finally, we finish the episode with a game of Product Hunt Roulette, where the team picks their favorite new companies featured on Product Hunt, a startup curation site.
#TheCrazyOnes #Startups #Entrepreneur
Listen to The Crazy Ones here: https://link.chtbl.com/OV4W93_W
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Alex Lieberman (@businessbarista)
Sophia Amoruso (@sophiaamoruso)
Jesse Pujji (@jspujji)
00:00 - Cold Open
00:45 - Intro
02:05 - The Rundown
02:54 - Why is Generative AI a GOLD RUSH?
12:47 - Jasper AI & Copy AI LIVE TESTS
16:18 - Takeaways & Ideas from Generative AI
22:46 - Is Executive Coaching Worth It?
13:35 - Jesse’s on what he’d do as CEO of Twitter
17:06 - Sophia on never wanting to be Elon Musk
21:29 - Alex on the 6 Steps to turn Twitter around
23:17 - How the crew would monetize Twitter
26:23 - Lessons for entrepreneurs watching
Links:
Sequoia Capital definition of Generative AI
The Timeline of Generative AI
Open AI’s $1B Funding From Microsoft
Jasper AI’s $1.5B Valuation
Product Hunt’s Website
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Episode 5: EMERGENCY POD – Today, hosts Alex Lieberman (@businessbarista), Sophia Amoruso (@sophiaamoruso), and Jesse Pujji (@jspujji) had to spontaneously hop on the mic to talk about Elon’s $44 Billion takeover of the world’s most topical social app, Twitter, and the steps he’s already taken to monetize the company. Then, the crew plays “what would you do as Elon Musk” and give their own ideas into how to turn the Twitter ship around.
#TheCrazyOnes #Startups #Entrepreneur
Listen to The Crazy Ones here: https://link.chtbl.com/OV4W93_W
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Sophia Amoruso (@sophiaamoruso)
Jesse Pujji (@jspujji)
00:00 - Cold Open
00:58 - Intro
01:11 - The Rundown
01:41 - Chronology of Elon’s story acquiring Twitter
06:41 - Elon announcing Twitter Blue
10:38 - Elon’s new Twitter Cohort
12:37 - Advertisers hinting to pull money out of Twitter
13:35 - Jesse’s on what he’d do as CEO of Twitter
17:06 - Sophia on never wanting to be Elon Musk
21:29 - Alex on the 6 Steps to turn Twitter around
23:17 - How the crew would monetize Twitter
26:23 - Lessons for entrepreneurs watching
Links:
Elon’s Tweet about “Twitter Blue”
Stephen King hating on Elon
Advertisers leaving Twitter
Learn more about your ad choices. Visit megaphone.fm/adchoices
Episode 4: Today, hosts Alex Lieberman (@businessbarista), Sophia Amoruso (@sophiaamoruso), and Jesse Pujji (@jspujji) breakdown MrBeast’s $1.5 billion valuation and exactly what factors have allowed MrBeast to be so successful. Then, the team shares their strategies for coming up with ideas for new businesses, and Alex shares his most recent startup pitches. And finally, for Startup AMA we answer a listener question about the best and worst hiring practices.
#TheCrazyOnes #Startups #Entrepreneur
Listen to The Crazy Ones here: https://link.chtbl.com/OV4W93_W
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Links:
Paul Graham’s How to Get Startup Ideas
How to get startup ideas in 10 diagrams
Alex’s 7 strategies to brainstorm startup ideas
Hiring Decision Template
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Episode 3: Today, hosts Alex Lieberman (@businessbarista), Sophia Amoruso (@sophiaamoruso), and Jesse Pujji (@jspujji) get into the MADNESS of the Gas app - a new social networking platform that has surpassed Instagram, TikTok and Twitter for daily downloads. Then, they get into how to & how NOT to conduct a layoff, whether it’s for one person or a company-wide one. And finally, the trio gets real about the secrets of QSBS and how understanding it can save you MILLIONS.
00:01 - Cold Open: Jesse speaking to Zuckerberg about the highschool version of Facebook
00:32 - Intro
01:35 - The Rundown
02:27 - How the “Gas” app works and how it stays positive
03:50 - Sophia on the Founder of Gas being a “master” of testing & iterating
05:45 - Alex on Highschoolers being the “best demographic” to build an app for
07:40 - Jesse on the difficulty of building consumer businesses
07:57 - Jesse’s highschool version of Facebook
10:00 - Jesse speaking to Mark Zuckerberg
12:44 - Where does the Gas app go from here?
13:35 - The “Gas” app’s ‘money printing machine’
15:40 - The second & third gen of Social Apps
17:50 - The Takeaways from Gas
21:48 - The “Hub & Spoke” Model of building your business
23:10 - Microsoft & the trend of Tech Industry Layoffs
24:32 - Sophia on layoffs needing more clarity & planning
28:50 - Jesse on Founders needing to be passionate about people & leadership
30:35 - The HORRIBLE Better.com Zoom layoff & reaction
34:30 - What is QSBS & how it saves founders MILLIONS
Links:
WSJ article on the Gas app
Nikita Bier’s tweet on Gas’s success
Allegations on China faltering the Gas app’s growth
Microsoft lays off 1,000
Chart of all Tech Industry Layoffs since COVID
How To Rally A Company Through a Round of Layoffs
Netflix on building a “team not a family”
Learn more about your ad choices. Visit megaphone.fm/adchoices
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