Startups Decoded

Every week, another investor posts that there’s never been more money for great founders. Eric Newcomer runs an anonymous survey of top VCs and hosts the Cerebral Valley AI Summit, so he hears the version they don’t post. What he hears is a market split hard into haves and have-nots. That gap is where first-time founders make their worst calls, planning around a story that was never written for them. Maya walks away knowing how investors actually read a pitch, why one lead beats a hundred maybes, and how to filter the noise without bouncing between ten experts. Episode outline From a school newscast to first hire at The Information to going independent Why audiences trust people over brands, and what AI is doing to the inbox Transparent bias versus the view from nowhere Haves and have-nots: who holds the leverage in venture right now VCs as energy-sensing machines, and why you only need one believer What anonymous VCs say about AI, robotics, energy and Anthropic Listen: Apple || Spotify || YouTube Eric Newcomer - https://www.linkedin.com/in/ericpnewcomer/ Founder of Newcomer, the startup and venture media company read by 100,000+ investors and operators. He spent six years covering tech for Bloomberg, breaking stories on Uber, Stripe, Sequoia and a16z, after starting out as the first employee at The Information. He also hosts the Cerebral Valley AI Summit and publishes a quarterly VC Sentiment Report built from anonymous interviews with top investors. Andy Walsh - https://www.linkedin.com/in/anwalsh/ Three-time founder with two exits who bootstrapped to $10M ARR, now host of Startups Decoded (top 2%, 850k+ downloads) and advising founders on growth through consulting and his podcast. Access All Areas. Listen: Apple || Spotify || YouTube Subscribe: Substack Connect: LinkedIn Web: startupsdecoded.com Socials: TikTok || Instagram || X Music Credit. “Neptuno” – Phondupe (Album: Onykia) https://phondupe.bandcamp.com/album/air-conditioning-vol-2 Disclaimer. The views and opinions shared on Startups Decoded are for informational purposes only and do not constitute investment or legal advice. Always consult a qualified professional before making any financial or legal decisions.

Most first-time founders treat angel money as the warm-up act before the real investors show up. Cheryl Kellond thinks that view is about five years out of date, and Play Money's data backs her up. Buzzy AI companies are raising nine figures at seed. Meanwhile, she argues the signaling bias has flipped, and the strongest fundamentals now sit with founders raising from angels, syndicates, and small funds. We get into her three-stage approach to early fundraising. She explains why Play Money makes founders pull $30K to $50K from their own network before showing a deal to anyone else, and why she'd rather read a year of your monthly updates than open your data room. Maya, if you're about to raise, you walk away with a sequence to follow and permission to stop chasing strangers first. Episode outline Why Cheryl refused to start a fund and built Play Money instead The accredited investor math that could rival early-stage VC Three stages of early fundraising, from your own network to strangers How an SPV turns a hundred small checks into one clean cap table line What angels want to see: your pace of learning, not a polished data room The $5,000 angel who closed a million-dollar deal Listen: Apple || Spotify || YouTube Cheryl Kellond - https://www.linkedin.com/in/c2kprofile/ Founder and CEO of Play Money, an angel investing platform that helps founders raise from strategic angels. She’s a concept-to-launch operator with more than $750M in revenue from version-one products. Her second company, Apostrophe, hit roughly $10M ARR in four years before Centivo acquired it in 2021. Andy Walsh - https://www.linkedin.com/in/anwalsh/ Three-time founder with two exits who bootstrapped to $10M ARR, now host of Startups Decoded (top 2%, 850k+ downloads) and advising founders on growth through consulting and his podcast. Access All Areas. Listen: Apple || Spotify || YouTube Subscribe: Substack Connect: LinkedIn Web: startupsdecoded.com Socials: TikTok || Instagram || X Music Credit. “Neptuno” – Phondupe (Album: Onykia) https://phondupe.bandcamp.com/album/air-conditioning-vol-2 Disclaimer. The views and opinions shared on Startups Decoded are for informational purposes only and do not constitute investment or legal advice. Always consult a qualified professional before making any financial or legal decisions.

Angus Dobbie spent fifteen years inside corporate recruiting, then built JobPass because the job hunt had turned into AI talking to AI. Applicants use it to fire out resumes, companies use it to filter them, and the recruiters who used to read them got cut to pay for the software. What struck me is how closely this mirrors building a company. You’re a solo operator with no boss, several pipelines to keep moving, and a front door so crowded the only reliable way in is a side door someone holds open for you. Maya walks away with the order of operations: relationships first, applications second, and a system that forces you to act on both. Episode outline Perth to a Sydney trading floor to New York, then losing it all in 2008 Why the job market always feels bad, and what AI changed for real Risk-averse hiring and the slide back to the average candidate Four opportunity pipelines, and why the spreadsheet dies in 24 hours Text roulette, dealer’s choice, and networking with no ask attached The post-launch flat spot and a note that says “I am not special” Listen: Apple || Spotify || YouTube Angus Dobbie - https://www.linkedin.com/in/adobbie/ Angus Dobbie spent two decades in international financial markets, then fifteen years in corporate recruiting, hearing the same job search frustrations from almost every candidate he met. In 2026, he walked away from corporate life to build JobPass, a system that helps job seekers run their search like a sales pipeline. Being his own boss was a long-held ambition, and in his words, it sounds good and is hard. Andy Walsh - https://www.linkedin.com/in/anwalsh/ Three-time founder with two exits who bootstrapped to $10M ARR, now host of Startups Decoded (top 2%, 850k+ downloads) and advising founders on growth through consulting and his podcast. Access All Areas. Listen: Apple || Spotify || YouTube Subscribe: Substack Connect: LinkedIn Web: startupsdecoded.com Socials: TikTok || Instagram || X Music Credit. “Neptuno” – Phondupe (Album: Onykia) https://phondupe.bandcamp.com/album/air-conditioning-vol-2 Disclaimer. The views and opinions shared on Startups Decoded are for informational purposes only and do not constitute investment or legal advice. Always consult a qualified professional before making any financial or legal decisions.

James Oliver Jr. emptied a retirement account to build his first startup, got into an accelerator, then watched his twins arrive at about two pounds each, days before the program started. He spent the following weeks driving between the NICU and the pitch room while his savings, his marriage, and his mental health ran out. The company died, and for years the story was about the product. This conversation is about the founder. James thinks hustle culture is trash, that the wrong investor will make your life miserable, and that self-awareness is the skill nobody teaches you. Now he's relaunching the same company as a different person. If you're running on fumes, this one gives you permission to stop, and a plan for what to do instead. Episode outline Cashing out his retirement to build WeMontage, and the IVF twins nobody planned around An emergency C-section, the NICU, and crying inside the accelerator Why three Today Show appearances didn't fix a customer acquisition problem Hustle culture, misaligned investors, and knowing when your tank is low Walks, meditation, journaling and the habits that actually stick Why he's relaunching WeMontage, and why this time is different Listen: Apple || Spotify || YouTube James Oliver Jr. - https://www.linkedin.com/in/james-oliver-jr/ James is a Techstars and gener8tor alum, co-author of Burn Bright Not Out, and host of the Founder Exhale podcast. Through the Kabila Founder Mental Health Fund, he pays for therapy for founders who can't afford it. I joined James on his podcast, The Founder Exhale. Take a listen Andy Walsh Three-time founder with two exits who bootstrapped to $10M ARR, now host of Startups Decoded (top 2%, 850k+ downloads) and advising founders on growth through consulting and his podcast. https://www.linkedin.com/in/anwalsh/ Access All Areas. Listen: Apple || Spotify || YouTube Subscribe: Substack Connect: LinkedIn Web: startupsdecoded.com Socials: TikTok || Instagram || X Music Credit. “Neptuno” – Phondupe (Album: Onykia) https://phondupe.bandcamp.com/album/air-conditioning-vol-2 Disclaimer. The views and opinions shared on Startups Decoded are for informational purposes only and do not constitute investment or legal advice. Always consult a qualified professional before making any financial or legal decisions.

Rob D. Willis once earned €3.50 for a three and a half hour walking tour of Berlin. He knew more history than most guides on the street, and that was the problem. The guides making real money told fewer facts and more stories, so Rob opened a spreadsheet,