founderlicious

E7: Semyon Dukach - Immigrant and Entrepreneur: From MIT and Blackjack to founder and investor

(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

E6: Steve Fredette - The drive, customer obsession, and GTM innovation that built Toast

(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

E4: Brendan Schwartz - Building Wistia for 18 years to ~200 employees after buying out investors

(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

E3: Mike Salguero - Bootstrapping ButcherBox to $600M in ARR while working 4 days/week...

(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

E2: Art Papas tells Bullhorn Founding Story to Almost $500M in ARR, VC vs. PE & Startup Profitably

(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

Larry Kim - Founder Story, Early Google Days with Eric Schmidt, Reverse Engineering to a $130M exit

(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