Not Another Podcast

Ryan Denehy was running Electric, an outsourced IT department for thousands of companies, when he decided to tear it up. The company had grown triple digits five years in a row and raised $200 million. On paper, nothing was wrong. Underneath, margins had stopped growing and every new customer cost more to win.So he rebuilt Electric as an AI-native company instead of bolting AI onto the old service business. Today it runs at 80% gross margins, up from 50% on its best day. He explains why "just add AI" fails for most services companies, why he doesn't believe AI will wipe out jobs, and what 20 years of founding has taught him about keeping his own head straight.In this episode:• Why he pivoted a $50M business while it was still growing• Why the best time to make big changes is when you have plenty of cash• How Electric went from 50% to 80% gross margins• Why he's skeptical of the AI roll-up boom• Why big leaps in technology have never cut total jobs• The Got Milk campaign he thinks AI needs• How a fake ID got his first startup its first customersNew episodes of Not Another Podcast every week. Watch on YouTube, listen on Spotify and Apple Podcasts.Timestamps:00:00 Intro01:14 Pivoting a $50M business02:51 What was wrong under the surface07:15 Why AI roll-ups are fragile09:42 Going from 50% to 80% margins11:34 Will AI take everyone's jobs?13:32 The coming AI services boom15:06 Non-technical founders who can build now21:13 Why you can't just "inject" AI23:07 Where's the Got Milk ad for AI?24:22 What the pivot really changed29:39 A failed first startup and a fake ID33:55 Why startups die from the inside37:47 Managing your own head as a founder42:00 The noon rule44:32 What he'd build with $0

Every investor told Mike Rizkalla to put ChatGPT inside his product for toddlers. He told them that was like handing a bazooka to a three-year-old. They funded his competitors instead, and within a year, Mike says, some of those AI toys were talking to kids about sex and how to make bombs.Mike is the founder and CEO of Snorble, a screen-free smart companion for kids that runs offline, has no camera, and lets parents set the routines and values. He's been building AI products for 15 years, had his first one acquired by Google in 2010, and before any of that spent 11 years as a punk rock guitarist who turned down a record label that wanted worldwide rights to his band. Brennan asks him why generative AI isn't safe for young kids yet, what it cost him to say no to that capital, and what every parent should check before buying an AI toy.They also get into the KPIs Mike says broke social media, the AI tool he says caught 3,500 predators in a single day, how he runs a hardware company with his phone off from bedtime to school drop-off, and why half his team invested in the company, including people he'd already laid off.In this episode:• Why generative AI isn't safe for young kids yet• The investor pressure to "just use ChatGPT," and what saying no cost him• What to look for, and what to avoid, when buying AI toys for your kids• Why cameras in a kid's bedroom are a hard no• The three KPIs he says broke social media• The AI tool that caught predators, and why big platforms passed on it• What his punk band taught him about building product• How half his team ended up investing, including people he'd laid offSubscribe for more unfiltered founder conversations on Not Another Podcast.Watch on YouTube, listen on Spotify and Apple Podcasts.Follow Brennan and Infinity for what's next.Timestamps:00:00 Intro01:10 Welcome Mike Rizkalla01:29 What the punk rocker would tell the CEO02:45 The band rule behind how he builds product05:07 Why there's no such thing as an MVP07:24 Shipping hardware through Covid09:58 Is hardware the only moat left?12:00 Why Snorble said no to generative AI14:11 A bazooka to a three-year-old15:11 Why AI is risky for young kids17:26 What he'd tell the CEO of Mattel20:47 Why AI went from lab to production too fast24:23 Our KPIs are wrong26:43 What parents should look for in AI toys30:09 Predators and plausible deniability32:40 Why cameras don't belong in kids' rooms35:07 Running a company with his phone off at night37:46 The team members who invested after layoffs42:58 When a 10 million dollar commitment fell through49:59 The 22-inch cookie that got his band on TV

Justin Kramer has watched friends raise $10, $20, even $30 million and end up sitting on it with no idea what to do next. He raised venture himself, and he still thinks most founders shouldn't.Justin spent his early career at Morgan Stanley managing money for people who were already rich. When GameStop and AMC started wiping out everyday investors, he left to build Moby, a company that uses AI to bring Wall Street-grade research to retail investors. Four-plus years in, Brennan asks him when a founder should never raise, and why the venture path is so hard to get off once you're on it.They also get into where the AI trade stands right now: valuations Justin calls out of control, why he still won't sit in cash, what Anthropic's IPO means for everyday investors, and why he's bearish on crypto even though he owns it.In this episode:• The three signs you should never raise venture capital• Why so many well-funded startups are turning into zombie companies• Why distribution is the only real moat when anyone can build anything• How Robinhood's confetti turned investing into a dopamine hit• Why he's bearish on crypto after holding it for years• The hidden costs of owning a house most people overlook• Thinking he was going out of business over and over, and what kept him goingSubscribe for more unfiltered founder conversations on Not Another Podcast.Watch on YouTube, listen on Spotify and Apple Podcasts.Follow Brennan and Infinity for what's next.Timestamps:00:00 Intro01:10 Welcome Justin Kramer01:41 Bringing Wall Street research to retail investors05:35 Robinhood confetti and gamified investing07:28 What GameStop taught retail investors09:21 Why he left Morgan Stanley12:29 Are tech valuations out of control?14:05 Anthropic's IPO and a $30 trillion forecast16:22 A 10% chance AI runs away from us19:22 Why he's anti-crypto25:11 Distribution is the only moat left26:14 3 signs you shouldn't raise venture27:23 Zombie companies and bloated venture funds29:36 Are we in an AI bubble?35:56 Is capitalism broken?

Chloe Samaha told the crew in the green room that your calendar predicts your future better than your ambition does. Brennan opened the episode with it.She's 22, co-founder and CEO of BOND, and she got into Y Combinator at 21 off a reply to a single tweet. Before that she cold emailed hundreds of private equity partners as a freshman, learned that sales was the one thing she could prove on an application with no resume behind it, and built the first version of BOND out of a founders house in San Francisco.Then there's the part that explains the rest of it. At 19, on her second solo skydive, her first parachute didn't open. She spent that night journaling and came out obsessed with where every hour goes.In this episode:• How a reply to one tweet turned into a YC acceptance at 21• What YC screens for in a founding team, and why most companies die from the co-founder relationship• The founder debt meeting she runs with her co-founders every week• Why she cuts every goal's timeline in half• What 2,000 CEOs told her about their own companies• Why she's bullish on Gen Z, and the 19-year-old hire who proved it• The jump where the parachute failed, and the 40 minutes of drills that saved herNew episodes of Not Another Podcast every week. Watch on YouTube, listen on Spotify and Apple Podcasts.Timestamps:00:00 Intro00:34 Your calendar predicts your future, not your ambition04:34 The reply to one tweet07:59 Auditing where the hours actually go09:57 Cutting every timeline in half14:19 How she got good at sales by 2119:40 Getting into Y Combinator22:54 Why she's bullish on Gen Z23:56 Hiring young, and the 19-year-old who ran distribution26:52 Getting 2,000 CEOs on the phone30:43 Breaking down the Product Hunt launch32:21 Collecting people more exceptional than her34:09 Why she builds in San Francisco36:18 What Beirut and Paris gave her as a founder41:51 Being a millionaire on paper at 2247:51 Why she's max on AI when her peers aren't52:16 What 2,000 CEOs don't know about their own companies59:05 The skydive, and what it made her decide1:00:12 The billboard

Brennan Pothetes builds companies out of New York, and in this episode he says San Francisco is a B tier place to start one. No guest this time. Just the arguments he has with founder friends over drinks, settled out loud with letter grades.Brennan ranks the six things founders fight about most: where to build, how to fund it, what to read, how to lead, how to work, and what to do with your twenties. Profitable businesses take S tier for funding, while venture, the path he has raised on for years, lands at B. Deep work blocks beat 996. Europe gets an F, and he knows his European investors are watching. Radical candor tops the management list, with fear-based hero mode at the bottom next to LinkedIn slop.For founders tired of consensus takes, the grades are the point.In this episode:• Why New York is S tier for applied AI, and what San Francisco's flood of talent actually costs you• The funding source Brennan puts above venture, debt, and private equity• The one way to fund a company he says you should never use• Why deep work blocks outrank the 996 schedule taking over AI• The book he made required reading at his own company, and the one he rates F tier• The leadership style he built his companies on, and the one that quietly wears teams down• What he tells 22-year-olds to do instead of firing off AI-written resumesSubscribe for more unfiltered founder conversations on Not Another Podcast.Watch on YouTube, listen on Spotify and Apple Podcasts.Follow Brennan and Infinity for what's next.Timestamps:00:00 Intro00:41 Welcome to the tier list00:58 Founder work philosophies01:45 Why 996 lands at C02:23 LinkedIn slop, F tier02:38 The best city to found in03:45 San Francisco at B04:05 Anywhere in Europe, F tier04:25 New York at S05:03 Fundraising sources05:54 The one way he says never to fund a company06:12 Books for founders07:17 Your professor's textbook, F tier07:41 Management and leadership styles09:21 Fear-based hero mode09:45 Radical candor at S10:04 What to do in your 20s10:19 Travel, and the Octopus card in Hong Kong11:28 The S tier career move12:21 AI-written resumes, F tier