Bill Smith asked for a briefcase on his 5th birthday, and it’s been all business since. After dropping out of school at age 16, Bill started, built, and sold 3 companies over the past 15 years. His last business, grocery delivery service Shipt, sold to Target in 2019 for half a billion dollars. But Bill didn’t rest on his success. The same year he exited Shipt, he started Landing, a flexible and furnished rental apartment service. So what’s next for this wunderkind turned startup mogul? 

Listen to Nathan and Bill discuss

• Dropping out of school without his parents knowing
• Figuring out the prepaid technology business 
• Exiting his first company to Green Dot Corporation 
• His step-by-step process for proving a business idea
• Why he never takes breaks between businesses 
• Proving demand in the early days of Shipt 
• Selling Shipt to Target for half a billion dollars
• Why selling Shipt changed his philosophy of business
• His goal to build Landing into an enduring company
• And much more business scaling advice…

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After multiple near-death experiences, Zeb Evans decided to build a business that was net positive on the world. However, he didn’t realize that a custom internal productivity tool would become the business he was searching for. In 2017, Evans cofounded ClickUp, an all-in-one productivity management tool now valued at $4 billion. 

Listen to Nathan and Zeb discuss: 

• Selling Disney DVDs from his hospital bed
• How a home invasion motivated him to drop out of school
• Starting his first company Fast Followerz from customized social tools
• How an unexpected seizure pushed him to move to Silicon Valley 
• Building ClickUp as an internal tool and discovering its value
• The early days of ClickUp and living in a stereotypical startup house
• Why investors were shocked that ClickUp was profitable 
• Maintain culture while scaling at a rapid rate 
• Why Zeb takes a bath every evening
• And much more tech startup advice…

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Marco Zappacosta's only professional job has been the cofounder and CEO of Thumbtack. Marco started the home services matchmaking website straight out of university with a dream to find a better solution of hiring a plumber. Since 2009, Thumbtack has raised half a billion dollars in funding and gone from 2 to 1,000 employees. But Thumbtack's success came from years of struggle to discover their perfect market fit. 

Listen to Nathan and Marco discuss: 

• Thumbtack's first users on both sides of the marketplace
• Enticing pros by creating stylized Craiglist ads
• The importance of telling the dream and data to investors
• Why investors are thinking about other investors
• Why getting a meeting is the easy part of fundraising 
• The difference between bootstrapped and VC businesses 
• Seeing values as the best version of your company 
• Creating "libraries" for their fully-remote workplace
• And much more VC and remote work advice…

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Nikhil Arora and Alejandro Velez started Back to the Roots by asking the same question in their business class–how can you grow mushrooms from used coffee grounds? So instead of taking their jobs in investment baking, the 2 friends began their journey of building an organic gardening brand for the next generation. 

Back to the Roots is America’s #1 organic gardening company and doubled its business 4 years in a row. They offer a wide range of grow kits, seeds, soil, and more to empower people to experience the magic of growing their food from inside their homes. 

Listen to Nathan chat with Nikhil and Alejandro about:

• Walking into a Whole Foods and pitching their first product 
• Growing their first mushrooms in a rented office space
• Hitting their first million in revenue off sources of waste
• Why going to a farmer’s market is the best lesson for business
• Transitioning from selling products to empowering growers 
• Navigating the accelerated growth of the industry during COVID-19
• Their relationship as cofounders over the past decade 
• Working with retailers like Home Depot, Target, and Walmart
• Their “Grow One, Give One” initiative 
• And much more business scaling advice…

Who do you want to see next on the podcast? Comment and let us know! And don't forget to leave us a 5-star review if you loved this episode.

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