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 lifeSubscribe to Morning Brew!Sign up for free today: https://bit.ly/morningbrewytFollow The Brew!Instagram - https://www.instagram.com/morningbrew/Twitter - https://twitter.com/MorningBrewTik Tok - https://www.tiktok.com/@morningbrewYouTube - https://www.youtube.com/@TheCrazyOnesPodFollow Our Hosts!Alex Lieberman (@businessbarista)Jesse Pujji (@jspujji) Learn more about your ad choices. Visit megaphone.fm/adchoices

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 #EntrepreneurListen to The Crazy Ones here: https://link.chtbl.com/OV4W93_WSubscribe to Morning Brew!Sign up for free today: https://bit.ly/morningbrewytFollow The Brew!Instagram - https://www.instagram.com/morningbrew/Twitter - https://twitter.com/MorningBrewTik Tok - https://www.tiktok.com/@morningbrewFollow Our Hosts!Alex Lieberman (@businessbarista)Jesse Pujji (@jspujji)Links: Alex’s tweet on 8 self-hating beliefs Learn more about your ad choices. Visit megaphone.fm/adchoices

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 #EntrepreneurListen to The Crazy Ones here: https://link.chtbl.com/OV4W93_WSubscribe to Morning Brew!Sign up for free today: https://bit.ly/morningbrewytFollow The Brew!Instagram - https://www.instagram.com/morningbrew/Twitter - https://twitter.com/MorningBrewTik Tok - https://www.tiktok.com/@morningbrewFollow 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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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 #EntrepreneurListen to The Crazy Ones here: https://link.chtbl.com/OV4W93_WSubscribe to Morning Brew!Sign up for free today: https://bit.ly/morningbrewytFollow The Brew!Instagram - https://www.instagram.com/morningbrew/Twitter - https://twitter.com/MorningBrewTik Tok - https://www.tiktok.com/@morningbrewFollow 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 happierLinks:Chop It Off (Neal Freyman) Learn more about your ad choices. Visit megaphone.fm/adchoices

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 #EntrepreneurListen to The Crazy Ones here: https://link.chtbl.com/OV4W93_WSubscribe to Morning Brew!Sign up for free today: https://bit.ly/morningbrewytFollow The Brew!Instagram - https://www.instagram.com/morningbrew/Twitter - https://twitter.com/MorningBrewTik Tok - https://www.tiktok.com/@morningbrewFollow 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 Learn more about your ad choices. Visit megaphone.fm/adchoices

Episode 12: Today, hosts Alex Lieberman (@businessbarista), Sophia Amoruso (@sophiaamoruso), and Jesse Pujji (@jspujji) brainstorm some brilliant ideas for making extra $$ in the new year, as well as how to come up with your own side hustle concepts. Then, the team gets deep with a discussion on year-end reflection and how they set goals and intentions for the coming year. And finally, we wrap with a fascinating Startup AMA addressing when and how to approach buying a domain.  #TheCrazyOnes #Startups #EntrepreneurListen to The Crazy Ones here: https://link.chtbl.com/OV4W93_WSubscribe to Morning Brew!Sign up for free today: https://bit.ly/morningbrewytFollow The Brew!Instagram - https://www.instagram.com/morningbrew/Twitter - https://twitter.com/MorningBrewTik Tok - https://www.tiktok.com/@morningbrewFollow Our Hosts!Alex Lieberman (@businessbarista)Sophia Amoruso (@sophiaamoruso)Jesse Pujji (@jspujji)(00:22) - Intro(00:58) - The Rundown(03:12) - How the team defines a side hustle(04:36) - How accurate the portrayal of Sophia’s story is on Netflix’s Girlboss(07:01) - Sophia’s view on side hustles(09:58) - Alex’s side hustle ideas(15:23) - Jesse’s side hustle ideas(18:20) - What many people don’t consider about side hustles(24:08) - How Jesse approaches year-end reflection(27:58) - How Sophia approaches reflecting at the end of the year(30:07) - How Alex approached year-end reflection this year(34:12) - The trick that helps Jesse stick with his New Year’s resolutions(39:14) - Startup AMA: Buying Domain Names(42:03) - How Jesse made 5-figures from selling a domain(43:21) - What went wrong with Sophia’s domain name purchase(45:22) - When it does, and does NOT make sense to spend $$ on buying a domain nameLinks:https://microacquire.com/ Learn more about your ad choices. Visit megaphone.fm/adchoices

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 #EntrepreneurListen to The Crazy Ones here: https://link.chtbl.com/OV4W93_WSubscribe to Morning Brew!Sign up for free today: https://bit.ly/morningbrewytFollow The Brew!Instagram - https://www.instagram.com/morningbrew/Twitter - https://twitter.com/MorningBrewTik Tok - https://www.tiktok.com/@morningbrewFollow Our Hosts!Alex Lieberman (@businessbarista)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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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 #EntrepreneurListen to The Crazy Ones here: https://link.chtbl.com/OV4W93_WSubscribe to Morning Brew!Sign up for free today: https://bit.ly/morningbrewytFollow The Brew!Instagram - https://www.instagram.com/morningbrew/Twitter - https://twitter.com/MorningBrewTik Tok - https://www.tiktok.com/@morningbrewFollow Our Hosts!Alex Lieberman (@businessbarista)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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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 #EntrepreneurListen to The Crazy Ones here: https://link.chtbl.com/OV4W93_WSubscribe to Morning Brew!Sign up for free today: https://bit.ly/morningbrewytFollow The Brew!Instagram - https://www.instagram.com/morningbrew/Twitter - https://twitter.com/MorningBrewTik Tok - https://www.tiktok.com/@morningbrewFollow Our Hosts!Alex Lieberman (@businessbarista)Sophia Amoruso (@sophiaamoruso)Jesse Pujji (@jspujji)00:43 - Intro03:12 - How Brian started 1-800-GOT-JUNK05:37 - 02E Brands’ reach and annual revenue06:40 - Brian’s passion and what keeps him motivated10:50 - How Brian got onto the Ellen Degeneres Show14:37 - Brian’s opinion on PR to promote your business16:20 - Brian’s decision to lay off his whole team in 199419:23 - Why Brian places a high importance on hiring for culture fit21:44 - The most important decisions Brian made to allow his business to grow25:54 - How 02E’s brand franchising works29:53 - How Brian determined the price of services for 1-800-GOT-JUNK32:07 - The systems Brian implements so that his ADD doesn’t derail him34:48 - How Brian’s management of the business has changed as the company has grown41:13 - Brian’s transition to being less hands-on with the day-to-day operations as his company grew42:48 - 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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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 #EntrepreneurListen to The Crazy Ones here: https://link.chtbl.com/OV4W93_WSubscribe to Morning Brew!Sign up for free today: https://bit.ly/morningbrewytFollow The Brew!Instagram - https://www.instagram.com/morningbrew/Twitter - https://twitter.com/MorningBrewTik Tok - https://www.tiktok.com/@morningbrewFollow Our Hosts!Alex Lieberman (@businessbarista)Sophia Amoruso (@sophiaamoruso)Jesse Pujji (@jspujji)00:44 - Intro01:40 - The Rundown03:13 - How Codie got to where she is today06:08 - The first boring business Codie bought10:30 - What lessons Codie has learned around deal-structuring and negotiation18:09 - The best negotiations Codie has ever done21:45 - What makes a great operator for your boring business23:52 - How Codie scares away a bad hire26:05 - What boring businesses are catching Codie’s eye right now33:22 - Why Codie is fascinated with Reese Witherspoon’s business model36:59 - Why Codie decided to dive deep into content creation46:10 - How Codie’s boring businesses compare with her media business48:15 - What Codie has learned about leadership50:38 - Codie’s hot takes and spiky opinionsLinks: Contrarian Thinking Newsletter Codie Sanchez YouTube Channel Learn more about your ad choices. Visit megaphone.fm/adchoices