(0:00) Intro

(5:10) Building a competitor to Facebook while at MIT

(10:03) Joining Endeca instead of starting a company

(14:40) Deciding NOT to go to business school to get an MBA

(16:31) Creating a side hustle with early Apple App Store products

(22:50) Becoming an entrepreneur inside Endeca and learning the power of vertical focus

(27:28) Launching Toast as an iPhone app

(30:18) Finding early product market fit

(35:07) Execution wins

(37:50) Disruption and focusing on finding what people want, not just fixing what people dislike

(42:27) Raising money to innovate on the GTM model

(46:01) The best business model wins. Understand unit economics

(54:54) You can test your business idea without a product.

(1:02:13) Ongoing innovation at Toast

(1:05:51) Execution and focus

(1:09:00) Impact of AI at Toast

(1:14:32) Productivity without burn out

(0:00) Intro

(1:55) Early entrepreneurial influences

(5:20) Starting Wistia

(8:11) Shredding business plans and burning thru savings

(11:02) The portfolio website for artists that didn't pay the bills

(12:44) The first business customer

(15:22) Going up against YouTube and Vimeo

(18:50) The Starbucks barista healthcare backup plan

(21:00) Raising an angel round

(24:50) Closing a $12/month deal after a summer of sorrow with no sales

(27:15) 5 years of work with just 4 people to get to profitability

(33:59) Growing the business more aggressively while having trouble reinvesting the profits

(38:54) One of their biggest mistakes building Wistia

(48:24) Getting 3 offers to buy the business

(55:55) Raising debt to buy out investors and early employees

(1:04:50) Switching from options to profit sharing with employees

(1:12:36) Switching back to options away from profit sharing with employees

(1:18:30) Wistia today and what's next for Brendan and Wistia

(0:00) Intro

(3:45) Buying CustomMade - relaunching and making every mistake in the book

(7:09) Raising VC for CustomMade and getting on the VC train

(11:24) CustomMade failing

(17:17) Starting ButcherBox as a hobby business while collecting unemployment

(21:56) The 3 core decisions that led to ButcherBox success

(28:06) Growth hacking to Go To Market success

(36:47) Starting 3 businesses at the same time to land on ButcherBox

(41:30) The psychological state that led to ButcherBox being launched

(43:43) Spotting trends and getting ahead of the Covid curveball

(48:10) How to finance inventory

(55:20) Working 4 days a week and work life balance

(1:03:57) How to work effectively, vivid visions, annual personal goal setting

(1:07:39) Mentorship, coaching, enneagram personality test, peer groups, YPO

(1:15:02) Long term ButcherBox plans