(00:00) HubSpot Co-Founder and CTO Dharmesh Shah joins Jason (2:36) Dharmesh explains what prompted his angel investing journey (6:19) HubSpots journey from startup to where it stands today (8:48) Dharmesh’s decision to focus on Small Minus Big (SMB) investing (11:12) Vanta - Get $1000 off your SOC 2 at https://vanta.com/twist (12:19) SMB investing conversation continued (16:08) The difference in cycles between big and small businesses (17:45) The best reason to start a company (21:25) Ways to go about assessing ideas (23:29) Crowdbotics - Get a free scoping session for your next big app idea at crowdbotics.com/twist (28:34) Breaking down the entrepreneurial work ethic (34:15) Anticapitalist sentiment in the U.S. (38:11) Fitbod - Get 25% off at https://fitbod.me/twist (39:40) Starting a business in a downturn (42:03) AI’s impact on business and Business Process Automation (BPA) (46:39) Dharmesh’s thoughts on the next stage of AI and the effect on jobs (54:41) How AI will lead to more efficient organizations and increase margins Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp FOLLOW Dharmesh: https://twitter.com/dharmesh FOLLOW Jason: https://linktr.ee/calacanis Thanks to our partners: (11:12) Vanta - Get $1000 off your SOC 2 at https://vanta.com/twist (23:29) Crowdbotics - Get a free scoping session for your next big app idea at crowdbotics.com/twist (38:11) Fitbod - Get 25% off at https://fitbod.me/twist Listen here: Apple: https://podcasts.apple.com/us/podcast/this-week-in-startups-audio/id315114957 Spotify: https://open.spotify.com/show/6ULQ0ewYf5zmsDgBchlkr9 Overcast: https://overcast.fm/itunes315114957/this-week-in-startups-audio More from us: Twitter: https://twitter.com/twistartups Instagram: https://www.instagram.com/thisweekinstartups Official site: https://thisweekinstartups.com/ Subscribe to our YouTube to watch all full episodes: https://www.youtube.com/channel/UCkkhmBWfS7pILYIk0izkc3A Subscribe to TWiST Clips for all the best moments: https://www.youtube.com/channel/UCS7tJlcUA6PzVHEMo-X7ddg #startups #entrepreneurship #investing #angelinvesting #tech #news #business