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. 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. Plus a rented Slovenian castle, a dungeon wine cellar, and a 2 a.m. question with an answer that made the work worth it. Chapters 00:06 — Welcome, and what he works on now 01:12 — Twenty-five years in broadband: Cox and Comcast from zero 03:08 — Three people, 25 markets, two years 06:16 — Why Comcast hired the outsider 08:13 — Build nothing: the 50-conversation rule 11:32 — Superhuman and what product-market fit feels like 13:04 — 6,000 conversations, 69 companies, 11 exits 14:22 — Why 90% shouldn't start companies 15:39 — Techstars, demo days, and curated founder events 18:24 — The global TikTok audience 19:56 — The Delaware C corp rule 21:27 — The Wyoming Corp call 23:44 — Onboarding, service, and doing things that don't scale 26:09 — Founder-led sales and the VP of sales mistake 33:16 — When to raise: growth, not just revenue 37:03 — SaaS isn't dying, it's repricing 41:27 — Hands On Angel as a media company 47:47 — What actually works on TikTok 53:24 — The paywall filter 56:31 — A castle wedding in Slovenia ABOUT OUR GUEST: 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. CONTACT: www.handsonangel.com steve@handsonangel.com linkedin.com/in/handsonangel Check out and subscribe to our new series SpeedRun here:    • SpeedRun by Tales from the Sky Lounge   Look for the Blog post for this episode here: https://talesfromtheskylounge.com/cat... What is THE SKY LOUNGE? Tales from the Sky Lounge is a podcast where we take you on a journey through the world of business, consulting, and venture investing. In each episode, we gather in our virtual sky lounge, high above the hustle and bustle of the everyday world, to hear stories from the people who are shaping the future of these industries. From entrepreneurs who are disrupting the status quo, consultants who are helping companies solve their biggest challenges, and investors who are making bets on the next big thing. ABOUT OUR HOST: Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CISO. 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, DevOps, QA, and Customer Success professionals. Subscribe and turn on notifications to listen to new episodes as they launch! YouTube:    • TALES FROM THE SKY LOUNGE   Spotify: https://open.spotify.com/show/6jz6ubc... Apple: https://podcasts.apple.com/us/podcast... Amazon: https://music.amazon.com/podcasts/4ba... Follow Tales From The SkyLounge on Social Media X/Twitter:   / tftskylounge   Instagram:   / tftskylounge   Production/Design: James Liebman Music: Soundstripe/Cody Martin - Sunrise