(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

(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

(0:00) Intros

(1:50) Growing up in a family of doctors

(5:13) Getting his first software job at Thompson Financial during the original internet boom

(7:26) Writing software to automate himself and all the interns out of a job

(11:40) Building and launching one of the first SaaS products in 1997

(16:09) Making a mistake leaving his first job for more money

(18:33) Quitting after 2 weeks without any planning

(19:40) New startup job and a painful lesson on listening to the customer

(23:00) Starting Bullhorn

(32:05) Market collapse and raising a really painful series A

(39:47) Burning the boats and becoming completely unemployable to make Bullhorn work

(42:02) Deciding to build a profitable company that didn't need anymore venture capital

(45:31) Switching from VC to PE backing

(50:19) Should tech startups be profitable?

(56:39) Right now is the best time to startup a business

(57:04) Art loves private equity - why he thinks it's so great

(1:00:21) Despite 25 years in the same company Art is still having fun at Bullhorn

(1:06:12) AI impact on staffing industry

(0:00) Entrepreneurship as a kid, starting a business in high school that won a $50,000 contract (6:57) Role models: Mom with her home based piano teaching business was earning 4x his father (12:49) Paying for his own college education with the money he earned in high school (15:42) Getting a job in Silicon Valley in the late 90's (17:53) Timing matters: Chamath Palihapitiya was just 1 year ahead in college - "you can crash your car into a goldmine" (18:54) Getting a job as a PM at Allaire (28:05) Switching from engineering to marketing and placing the largest ad order of the year with Google (37:54) Getting a green card and starting a business in Boston, meeting Sergey Brin and Eric Schmidt and getting turned down for a job at Google (43:10) Getting a services business off the ground and earning enough cash to start buying houses and one car a month while getting no's from VCs (57:56) Getting the first VC funding for WordStream (1:02:20) Stepping down as CEO (1:10:18) Scaling Go To Market and dealing with Product Market Fit issues at WordStream (1:20:00) Getting to $55M in ARR and selling WordStream for $130M (1:24:30) Starting Customers.ai and motivation to do the next company (1:38:10) Doing things differently as a second time founder (1:45:50) Everyone should pursue entrepreneurship