(00:00) Introduction to Semyon Dukach's Journey

(02:12) From Immigrant to Entrepreneur: Semyon's Early Years

(04:52) The MIT Blackjack Team: Risk and Reward

(10:09) Starting Fast Engines: The First Company

(20:15) Taking SMTP Public: A Unique Journey

(30:09) Transitioning to Investing: The Angel Investor Path

(45:55) Leading Techstars: Mentorship and Growth

(49:40) One Way Ventures: Investing in Immigrant Founders

(57:32) Navigating Risk: Semyon's Perspective on Entrepreneurship

(01:02:57) The Future of Tech: Optimism Amidst Challenges

(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