Ep52 Steve Walsh — Founders: These Are the Mistakes You Don't Know You're Going to Make

Today in the Sky Lounge, we are joined by Steve Walsh, founder of Hands On Angel. Steve spent 25 years in US broadband doing the same job twice: building a B2B division out of nothing. At Cox Communications it went from no customers and no revenue to a billion dollars. At Comcast, he walked into a room with two other people, a mandate to launch 25 markets in two years, and unlimited capital. He asked what the plan was. His boss stood up, told him that was why they hired him, and left the room. Ten years later it was a $10 billion business.<p>Nine years ago he started over. Roughly 6,000 founder conversations have produced the 69 companies he actually works with — about $1 billion raised in aggregate and 11 exits. He explains why he won't touch anything that isn't a Delaware C corp, why a founder who hires a VP of sales at three customers is already finished, why onboarding is the last real differentiator, and why he thinks 90% of people shouldn't start companies at all.</p><p>Plus a rented Slovenian castle, a dungeon wine cellar, and a 2 a.m. question with an answer that made the work worth it.</p><p>ABOUT OUR GUEST: </p><p>Steve Walsh is the Founder of Hands On Angel, a media platform helping early-stage technology founders navigate the startup journey. Every day, Steve creates content focused on fundraising, founder decision-making, investor perspectives, and company building—all grounded in real conversations with founders. As an active angel investor in 69 startups and a Mentor in Residence at Techstars, he combines decades of operating experience with practical advice that's helping the next generation of entrepreneurs raise capital and build enduring companies. Companies in his portfolio have gone on to raise more than $1.4 billion.</p><p>CONTACT:</p><p>www.handsonangel.com</p><p>steve@handsonangel.com</p><p>linkedin.com/in/handsonangel</p><p>What is THE SKY LOUNGE?</p><p>Tales from the Sky Lounge takes you on a journey through business, consulting, and venture investing, hearing stories from the entrepreneurs, consultants, and investors shaping these industries.</p><p>ABOUT OUR HOST:</p><p>Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.</p><p>He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market. As an entrepreneur, turn-around expert, technology and product leader, and mentor, Todd has held full corporate P&L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.</p><p>Subscribe and turn on notifications to listen to new episodes as they launch!</p><p>YouTube: https://www.youtube.com/playlist?list=PLfeCS-Varb4gu2uCwyRTXWWEdP676Huh6</p><p>Spotify: https://open.spotify.com/show/6jz6ubcaUZ20Xh8TXhwzEN</p><p>Apple: https://podcasts.apple.com/us/podcast/tales-from-the-sky-lounge/id1730134658</p><p>Amazon: https://music.amazon.com/podcasts/4ba289a5-0d33-4589-95c7-83416731a864/tales-from-the-sky-lounge</p><p>Follow Tales From The SkyLounge on Social Media</p><p>X/Twitter: https://x.com/TFTSkyLounge</p><p>Instagram: https://www.instagram.com/tftskylounge/</p><p>Learn more about TechCXO: https://www.techcxo.com/</p><p>Production/Design: James Liebman</p><p>Music: Soundstripe/Cody Martin-Sunrise</p>