Aug 30: The AI watchdog linking Sentry errors to PRs
Good morning. Background agents are quietly replacing human customer success for solo founders.
Solo founders scaling with AI are hitting a bottleneck in customer success. A new background agent solves this by cross-referencing Sentry errors and open GitHub PRs with specific client accounts. It proactively flags the top three failing issues per customer before they even submit a ticket.
Build it tonight
A highly scoped background agent that cross-references Sentry errors with open GitHub PRs to surface failing client accounts. Easily buildable this weekend.
B2B SaaS
AI customer success watchdog agent
A background agent that cross-references customer accounts with Sentry errors and open PRs to proactively surface the top three failing issues per client.
Why now: Cloud coding agents can now autonomously monitor production errors, check GitHub for open PRs, and synthesize account health without human intervention.
Discussing: Solo founders and small engineering teams managing multiple B2B accounts
“It goes into each account and says, what's going on with this account?... where are the century errors?... it comes up with the top three things that are going wrong. And then either like, well, wait, have they been fixed?... or is there an open PR”
OpportunitySolo founders scaling with AI agents lack the human headcount for customer success; background agents can bridge the gap between error logs and client accounts.
I spent $20,000 on Devin in a month. Here’s what I learned | Ryan Carson (solo founder) · Aug 24, 2026
Sanity check: What would have to be true: founders trust an automated agent to accurately map technical error logs to specific client accounts without generating false positives.
Build it without code
Drive a hydraulic crane truck to industrial facilities and smash their open-top dumpsters, splitting the savings on their $10k/month trash pickup bills.
service productization
Mobile commercial trash compaction
Operate mobile trucks equipped with hydraulic cranes to smash open-top dumpsters at industrial facilities, cutting their trash pickup costs in half.
Why now: Industrial facilities face high recurring waste management costs that can be instantly reduced with mobile hydraulic equipment.
Discussing: Industrial businesses, warehouses, and factories spending $10k+ a month on open-top dumpsters.
“The deal is basically, let's say you get 10 pickups a month, a thousand bucks. That's $10,000 a month you're spending on trash. We'll get you down to just round numbers five and we'll split the savings with you.”
OpportunitySell a pure financial ROI no-brainer where the only objection is belief, proven immediately by smashing their dumpster on-site.
Asking 3 young millionaires how they make $1.8M, $5M, & $12M/year · Aug 19, 2026
Sanity check: What would have to be true: industrial facilities prefer splitting savings with a vendor over simply renting their own compaction equipment.
Today's Startup Ideas
Specific plays distilled from this week's founder/operator podcasts.
B2B SaaS
AI customer success watchdog agent
A background agent that cross-references customer accounts with Sentry errors and open PRs to proactively surface the top three failing issues per client.
Why now: Cloud coding agents can now autonomously monitor production errors, check GitHub for open PRs, and synthesize account health without human intervention.
service productization
Mobile commercial trash compaction
Operate mobile trucks equipped with hydraulic cranes to smash open-top dumpsters at industrial facilities, cutting their trash pickup costs in half.
Why now: Industrial facilities face high recurring waste management costs that can be instantly reduced with mobile hydraulic equipment.
fintech
Motorcycle Manufacturing And Lending For Drivers
Combine motorcycle manufacturing with small business lending tailored specifically for delivery drivers in emerging markets.
Why now: The gig economy in emerging markets is massive, but traditional banks refuse to underwrite delivery drivers for vehicle loans.
vertical AI tooling
B2B AI for family law discovery
Pivot from B2C divorce AI to B2B family law software after discovering lawyers will pay to automate discovery workflows amidst paralegal shortages.
Why now: LLMs are finally capable of parsing complex, unstructured discovery documents, solving acute paralegal shortages.
vertical AI tooling
AI-automated insurance billing for independent dentists
An AI platform that automates insurance claims and appeals for independent dentists, taking a 2.5% to 3.5% cut of processed revenue.
Why now: AI voice and NLP agents are now capable of navigating complex, adversarial phone trees and API-less systems used by insurance companies.
vertical AI tooling
AI Operations Manager For Solo Therapists
Replace human receptionists and billing clerks with an AI agent to dramatically increase the profit margins of solo therapy practices.
Why now: AI agents are now capable of handling multi-step administrative workflows like scheduling and billing autonomously.
traditional SMB
Franchise territory roll-up strategy
Buy a small franchise territory to enter the system, then use 100% SBA financing to acquire larger neighboring territories with zero equity down.
Why now: SBA rules allow 100% financing for same-NAICS code acquisitions, making intra-franchise roll-ups highly capital efficient.
consumer hardware
Consumer cooking robot for one-pot meals
A $1,500 computer-vision-powered cooking robot that automates stirring and heat regulation for one-pot meals, generating $2M in monthly pre-orders.
Why now: Computer vision and AI are now cheap enough to deploy in a $1,500 countertop appliance to monitor food texture and color.
physical-world infra
Automated trailer rental business
Buy used trailers and automate rentals using lockboxes, GPS trackers, and self-serve booking software to generate $4,000 monthly profit on five hours of work.
Why now: Cheap GPS trackers, reliable automated booking software, and digital identity verification make unattended physical asset rentals viable.
vertical AI tooling
AI Outside Counsel Bill Analyzer
An AI system that analyzes outside counsel bills to help in-house legal teams reduce costs, a model validated by a 425 million euro acquisition.
Why now: Machine learning can now accurately parse complex, unstructured legal invoices at scale to identify billing inefficiencies.
physical-world infra
Porcelain Enamel Infrastructure Signage
Fabricate fire-proof, graffiti-resistant porcelain enamel signs for transit authorities and national parks to capture 25-35% EBITDA margins in a highly defensible physical niche.
Why now: AI is threatening professional services and software, making defensible, physical-world manufacturing with high margins an attractive alternative for acquisition entrepreneurs.
hiring playbook
Firearm Sales Reps As GMs
Hire former gun salespeople for blue-collar GM roles because their experience vetting firearm buyers translates directly into strong character judgment for hiring technicians.
Why now: Finding reliable GMs for small home service businesses is notoriously difficult; looking in adjacent high-stakes retail environments yields overlooked talent.
physical-world infra
B2B backup generator service
Acquire backup generator service businesses and use AI to speed up complex quoting and field technician training to outcompete slow incumbents.
Why now: Electricity demand, data centers, and electrical contractors are booming, creating a massive need for reliable backup power.
ETA Strategy
Committed Capital Micro-Rollups
Raise $10M to $25M upfront to acquire 10 to 20 micro-businesses without initial bank debt, bypassing the competitive middle-market search fund space.
Why now: The traditional search fund target of $4M EBITDA is highly competitive; moving down-market requires a new financing structure to handle the volume.
service productization
Public Art RFP Co-Bidding
Win municipal transit authority art budgets by sourcing artists on Instagram and co-applying to RFPs as their exclusive fabrication partner.
Why now: Legacy manufacturers rely on passive inbound; applying modern social media outbound to niche municipal RFPs yields immediate pipeline growth.
service productization
Low-Skill Service Productization
Optimize home service routing for high-volume, low-skill tasks like $80 mosquito sprays rather than $250 bee removals that require specialized technicians and complex scheduling.
Why now: Blue-collar labor shortages make businesses reliant on specialized technicians fragile; low-skill, repeatable services are easier to staff.
service productization
Weekly all-or-nothing attendance bonuses
Solve blue-collar no-shows by offering a percentage of weekly production pay that is entirely forfeited if the employee is late even once that week.
Why now: Unreliable labor is the primary bottleneck for home service businesses; strict micro-incentives outperform broad wage increases.
vertical SaaS
Instagram storefront for pop-up food drops
A pre-order and pickup platform that lets home chefs and pop-up bakers sell food drops directly to their Instagram audience.
Why now: Expanded cottage food laws in states like Texas and Arizona, combined with a post-COVID surge in tech workers quitting to start niche food businesses.
CPG
Refrigerated afternoon chocolate bars for adults
A refrigerated chocolate bar brand targeting the adult afternoon snack market that hit $40M in annual revenue through reality-TV-style founder content.
Why now: Refrigerated sections are expanding across all grocery categories, creating new premium shelf space for preservative-free products.
developer tools
MCP-based AI coding agent security
Build a security tool that plugs directly into code editors via MCP to block malicious packages pulled by AI coding agents.
Why now: The rapid adoption of AI coding agents has created a new attack vector where malicious packages are hallucinated or pulled in without human review.
Movements to Watch
Patterns surfacing across multiple shows. Track these before consensus.
vertical AI tooling
AI Agents Target Niche Back-Office Workflows
Founders are moving past generic chatbots to build highly specialized agents that automate specific administrative bottlenecks, from family law discovery to dental insurance appeals.
physical-world infra
Hardware Returns to Solve Physical Bottlenecks
As software margins compress, operators are finding software-like profitability in unsexy physical infrastructure, ranging from automated trailer rentals to porcelain enamel signage.
service productization
Productizing Low-Skill Local Services
Operators are avoiding the specialized labor shortage by focusing on high-volume, low-skill tasks that can be easily standardized, routed, and staffed with entry-level workers.
Founder Signal
How operators are thinking — frameworks, anti-patterns, sharp moves.
Micro-incentives fix blue-collar attendance.
Generic year-end bonuses fail to change daily behavior. Offering a weekly percentage of production pay that is entirely forfeited if an employee is late even once solves 80% of no-shows.
Hire former gun salespeople for GM roles.
Retail firearm sales require high-stakes character assessment. This creates an untapped talent pool of operators skilled at reading people, which translates perfectly to hiring reliable blue-collar technicians.
Capital Flow
Where money's moving today — funding rounds, M&A, valuation signals.
Zero-down franchise roll-ups via SBA.
SBA rules allow 100% financing for acquisitions within the same NAICS code. Buying a small franchise territory serves as a cheap wedge to unlock zero-down acquisitions of larger neighboring peers.
Bypassing the search fund middle market.
Raising $10M to $25M upfront to acquire 10 to 20 micro-businesses with all equity eliminates the path-dependency risk of deal-by-deal raises and avoids early debt service pressure.
From the Conversations
AI-automated insurance billing for independent dentists
3 strangers showed us how they made $8M, $10M, & $40M/year
Aug 17, 2026 · 1h 0m · 3 quotes pulled
▶ Listen“We have AI calling the insurance company to get the status of these claims, AI submitting the claim, AI voice being like hey you did not approve this why not.”
“AI voice and NLP agents are now capable of navigating complex, adversarial phone trees and API-less systems used by insurance companies.”
Motorcycle Manufacturing And Lending For Drivers
Bill Gates foresees massive AI job loss: these VCs disagree | E2330
Aug 26, 2026 · 1h 31m · 2 quotes pulled
▶ Listen“motorcycle manufacturing and small business lending company for delivery drivers in Sao Paulo, Brazil. And that business is on fire. It's doing over $300 million in revenue, profitable, growing 60%, 70% per year.”
“The gig economy in emerging markets is massive, but traditional banks refuse to underwrite delivery drivers for vehicle loans.”
B2B AI for family law discovery
I spent $20,000 on Devin in a month. Here’s what I learned | Ryan Carson (solo founder)
Aug 24, 2026 · 44m · 2 quotes pulled
▶ Listen“nobody wants to use AI for divorce. They want lawyers... She said, I love it. You know, there's a paralegal shortage. There's this discovery thing we do in divorce is a nightmare. I love it and I want to pay for it.”
“LLMs are finally capable of parsing complex, unstructured discovery documents, solving acute paralegal shortages.”
Sources
▶ ListenHow I AI
I spent $20,000 on Devin in a month. Here’s what I learned | Ryan Carson (solo founder)<p><strong>Ryan Carson</strong> is a five-time founder and the current solo founder of Untangle, a B2B SaaS platform for family law firms. Before Untangle, he co-founded Treehouse, an online coding education platform, and has spent the better part of two decades building and leading tech companies. He’s active on X, where he shares his solo founder journey in real time, including what he actually spends on AI tools each month.</p><p><br></p><p><strong>What you’ll learn:</strong></p><ol><li>Why Ryan manages 15 concurrent Devin agents with a folder system and a piece of paper, not a dashboard</li><li>The Watchdog playbook: what he built to replace a customer success team across every law firm account</li><li>How his LAN PR skill closes the loop on 40 daily PRs without a QA team reviewing a single one</li><li>Why he moved off local agents almost entirely, and the one situation where he still reaches for Codex</li><li>The design workflow we’re both using: Claude Design into a Markdown spec, then Codex to build the real thing</li><li>What he found when he got away from his computer and met a real customer, and why it changed his entire product direction</li><li>How he’s hiring his first engineer without a single phone screen or interview</li><li>Why we both think more AI output is actually the wrong goal, and what to optimize for instead</li></ol><p>—</p><p><strong>Brought to you by:</strong></p><p><a href="https://workos.com/?utm_source=lennys_howiai&utm_medium=podcast&utm_campaign=q22025"><strong>WorkOS</strong></a>—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more</p><p><a href="https://jira.dev"><strong>Jira AI SDLC</strong></a>—Get your tokens’ worth with Jira</p><p>—</p><p><strong>In this episode, we cover:</strong></p><p>(00:00) Introduction to Ryan Carson</p><p>(02:55) Ryan’s update: Untangle, the divorce PMF pivot, and B2B growth</p><p>(07:35) Ryan’s current Devin stack: folders, P0 threads, and the paper list</p><p>(16:29) Watchdog playbook: account monitoring across every firm</p><p>(18:09) Managing agent decision fatigue: Ryan’s method vs. Claire’s</p><p>(20:32) Producing more output does not make a better product</p><p>(22:47) Using cloud agents for ops beyond just code</p><p>(25:14) When to use Codex vs. Devin vs. Claude Code</p><p>(27:15) Merge Mommy recap</p><p>(28:15) LAN PR skill: review loops, video walkthrough, and auto-merge</p><p>(30:20) Slack vs. Devin threads for async team communication</p><p>(35:58) Claude Design plus Codex for building a technical design system</p><p>(39:00) EA tools: Polly the OpenClaw vs. Claude Code on a Mac Mini</p><p>(42:09) Quick recap and final thoughts</p><p>—</p><p><strong>Tools referenced:</strong></p><p>• Devin (Cognition): <a href="https://www.cognition.ai/">https://www.cognition.ai/</a></p><p>• Codex (OpenAI): <a href="https://openai.com/codex">https://openai.com/codex</a></p><p>• Claude Code/Claude Design (Anthropic): <a href="https://www.anthropic.com/claude">https://www.anthropic.com/claude</a></p><p>• OpenClaw (Claude-based desktop client): <a href="https://openclaw.ai/">https://openclaw.ai</a></p><p>• Cursor: <a href="https://www.cursor.com/">https://www.cursor.com/</a></p><p>• BugBot (Devin’s built-in PR review): <a href="https://cursor.com/bugbot">https://cursor.com/bugbot</a></p><p>• Sentry (error monitoring referenced in Watchdog): <a href="https://sentry.io/">https://sentry.io/</a></p><p>• Ugmonk (analog to-do system): <a href="https://ugmonk.com/">https://ugmonk.com/</a></p><p>—</p><p><strong>Other references:</strong></p><p>• Devin playbooks/skills documentation: <a href="https://docs.cognition.ai/">https://docs.cognition.ai/</a></p><p>• Jack Dorsey/Buzz (async-first communication referenced): <a href="https://buzz.new/">https://buzz.new/</a></p><p>• Merge Mommy (Claire’s Eve agent for PR risk scoring, deployed on Vercel): <a href="https://www.lennysnewsletter.com/p/build-an-ai-code-review-bot-in-30">https://www.lennysnewsletter.com/p/build-an-ai-code-review-bot-in-30</a></p><p>—</p><p><strong>Where to find Ryan Carson:</strong></p><p>X: <a href="https://x.com/ryancarson">https://x.com/ryancarson</a></p><p>Untangle: <a href="https://untangle.us/">https://untangle.us</a></p><p>—</p><p><strong>Where to find Claire Vo:</strong></p><p>ChatPRD: <a href="https://www.chatprd.ai/">https://www.chatprd.ai/</a></p><p>Website: <a href="https://clairevo.com/">https://clairevo.com/</a></p><p>LinkedIn: <a href="https://www.linkedin.com/in/clairevo/">https://www.linkedin.com/in/clairevo/</a></p><p>X: <a href="https://x.com/clairevo">https://x.com/clairevo</a></p><p>—</p><p>Production and marketing by <a href="https://penname.co/">https://penname.co/</a>. For inquiries about sponsoring the podcast, email [email protected].</p>
▶ ListenMy First Million
Asking 3 young millionaires how they make $1.8M, $5M, & $12M/year30+ blue-collar business ideas: https://clickhubspot.com/refn Episode 853: Sam Parr ( https://x.com/theSamParr ) and Shaan Puri ( https://x.com/ShaanVP ) ask 3 founders to tell them the juiciest number behind their businesses and get advice live. — Show Notes: (0:00) Nick Haschka, OnPoint Generators (17:39) Kevin Moyer, Smash My Trash (36:54) Noam Eisenberg, TMJaw — Links: • OnPoint Generators - https://onpointgen.com/ • Smash My Trash - https://howitworks.smashmytrash.com/ • Your TMJ Pen - https://yourtmj.com/ — Check Out Sam's Stuff: • Hampton (joinhampton.com): My community for founders. Average member does $25m/year. Many of the guests are members. Get after it...apply: http://joinhampton.com/mfm — Check Out Shaan's Stuff: • Shaan's weekly email - https://www.shaanpuri.com • Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents. • Mercury - Shaan uses Mercury across all of his companies. you can too: http://mercury.com/ Mercury is a fintech company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., Members FDIC • I run all my newsletters on Beehiiv and you should too + we're giving away $10k to our favorite newsletter, check it out: beehiiv.com/mfm-challenge My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano /
▶ ListenThis Week in Startups
Bill Gates foresees massive AI job loss: these VCs disagree | E2330<p dir="ltr">This Week In Startups is made possible by:</p> <p dir="ltr">Lightfield<br /> <a href="https://lightfield.app">https://lightfield.app</a></p> <p dir="ltr">Northwest Registered Agent<br /> <a href= "https://www.northwestregisteredagent.com/twistdomain">https://www.northwestregisteredagent.com/twistdomain</a></p> <p dir="ltr">Rippling<br /> <a href= "https://Rippling.ai/twist">https://Rippling.ai/twist</a></p> <p><strong> </strong></p> <p dir="ltr">Today's show:</p> <p dir="ltr">*Bill Gates dropped a 6,000 word warning: AI will be "the greatest equalizer ever invented, or the worst sort of injustice." The Microsoft icon has an AI agenda for the US: new national institutions, AI use taxes, and jobs legally reserved for humans only.</p> <p dir="ltr">Our VC roundtable guests — Sheel Mohnot (Better Tomorrow Ventures), Dave McClure (Practical Venture Capital), and Hussein Kanji — push back hard. Is taxing profits a better fix for AI taking jobs than taxing the tokens themselves?</p> <p dir="ltr">PLUS: Meta's $17B kids safety settlement… does it go far enough? Why does Stripe want OpenRouter? A peek at the VC's actual portfolio mark-ups. AND begun, the AI agent wars have. Our panel chooses between OpenClaw, Instinct, and Grok Bot.</p> <p dir="ltr">Guests</p> <p dir="ltr">Sheel Mohnot on X: <a href= "https://x.com/pitdesi">https://x.com/pitdesi</a></p> <p dir="ltr">Better Tomorrow Ventures: <a href= "https://www.btv.vc/">https://www.btv.vc/</a></p> <p dir="ltr">Dave McClure on X: <a href= "https://x.com/davemcclure">https://x.com/davemcclure</a></p> <p dir="ltr">Practical Venture Capital: <a href= "https://practicalvc.com/">https://practicalvc.com/</a></p> <p dir="ltr">Hussein Kanji on X: <a href= "https://x.com/hkanji">https://x.com/hkanji</a></p> <p dir="ltr">Hoxton Ventures: <a href= "https://hoxtonventures.com/">https://hoxtonventures.com/</a></p> <p dir="ltr">Relevant Links</p> <p dir="ltr">GatesNotes: "The turbulent AI era is here": <a href= "https://www.gatesnotes.com/a-turbulent-ai-era-and-critical-choices-to-make"> https://www.gatesnotes.com/a-turbulent-ai-era-and-critical-choices-to-make</a></p> <p dir="ltr">NPR: Meta settlement coverage: <a href= "https://www.npr.org/2026/08/26/nx-s1-5944781/meta-settlement-child-safety-lawsuit"> https://www.npr.org/2026/08/26/nx-s1-5944781/meta-settlement-child-safety-lawsuit</a></p> <p dir="ltr">TechCrunch: Stripe agrees to buy OpenRouter: <a href= "https://techcrunch.com/2026/08/16/stripe-will-reportedly-acquire-ai-gateway-startup-openrouter-for-7b/"> https://techcrunch.com/2026/08/16/stripe-will-reportedly-acquire-ai-gateway-startup-openrouter-for-7b/</a></p> <p dir="ltr">Skild AI S1 Demo: <a href= "https://www.skild.ai/blogs/s1">https://www.skild.ai/blogs/s1</a></p> <p dir="ltr">Instinct AI agent (waitlist): <a href= "https://instinct.co/">https://instinct.co/</a></p> <p dir="ltr">TechCrunch: Instinct coverage: <a href= "https://techcrunch.com/2026/08/24/instincts-powerful-ai-assistant-is-raising-privacy-and-security-concerns/"> https://techcrunch.com/2026/08/24/instincts-powerful-ai-assistant-is-raising-privacy-and-security-concerns/</a></p> <p dir="ltr">CNBC: OpenAI CFO says IPO is coming in 2027: <a href= "https://www.cnbc.com/2026/08/19/open-ai-ipo-timing-2027-friar.html"> https://www.cnbc.com/2026/08/19/open-ai-ipo-timing-2027-friar.html</a></p> <p dir="ltr">Basis: <a href= "https://www.getbasis.ai/">https://www.getbasis.ai/</a></p> <p dir="ltr">TaxGPT: <a href= "https://www.taxgpt.com/">https://www.taxgpt.com/</a></p> <p dir="ltr">Cusp AI: <a href= "https://cusp.ai/">https://cusp.ai/</a></p> <p dir="ltr">Abacus: <a href= "https://goabacus.co/">https://goabacus.co/</a></p> <p dir="ltr">Micro1: <a href= "https://www.micro1.ai/">https://www.micro1.ai/</a></p> <p dir="ltr">Mottu: <a href= "https://mottu.com.br/">https://mottu.com.br/</a></p> <p dir="ltr">EquityBee: <a href= "https://equitybee.com/">https://equitybee.com/</a></p> <p dir="ltr">Kiva: <a href= "https://www.kiva.org/">https://www.kiva.org/</a></p> <p dir="ltr">Timestamps:</p> <p dir="ltr">0:00 It's Hussein's first time on the VC Roundtable!</p> <p dir="ltr">2:09 Gates says "turbulent era" for AI is here</p> <p dir="ltr">8:56 Microloans, Kiva, and "universal basic income"</p> <p dir="ltr">9:23 Thanks to our partner, Lightfield, the AI-native CRM that updates itself, so you never have to! Try it for free at https://lightfield.app</p> <p dir="ltr">13:00 Why sole proprietorships may be AI's biggest beneficiary</p> <p dir="ltr">20:29 Got a new business idea? Northwest helps you bring it to life. Get a free domain, email, phone number, and more, with no purchase required! Learn more at https://www.northwestregisteredagent.com/twistdomain</p> <p dir="ltr">21:00 Should the gov't take a stake in AI labs?</p> <p dir="ltr">30:24 Thanks to our partners at Rippling! Head to https://Rippling.ai/twist to get the only AI built to give you full visibility across your startup and take complex actions across your entire business.</p> <p dir="ltr">32:44 Meta's $17.1B settlement</p> <p dir="ltr">45:14 Is anything still fundable outside of AI?</p> <p dir="ltr">46:29 Stripe and SpaceX deals</p> <p dir="ltr">55:54 Skild AI's pancake flipping demo</p> <p dir="ltr">59:49 Sheel's Hottest Takes</p> <p dir="ltr">1:04:37 Dave's Charts</p> <p dir="ltr">1:09:07 Who loses money when there are no IPOs?</p> <p dir="ltr">1:16:49 The Agent Wars heat up</p> <p dir="ltr">1:24:56 Everyone's favorite investments</p> <p><strong> </strong></p> <p dir="ltr">Subscribe to the TWiST500 newsletter: <a href= "https://ticker.thisweekinstartups.com">https://ticker.thisweekinstartups.com</a></p> <p dir="ltr">Check out the TWIST500: <a href= "https://www.twist500.com">https://www.twist500.com</a></p> <p dir="ltr">Subscribe to This Week in Startups on Apple: <a href= "https://rb.gy/v19fcp">https://rb.gy/v19fcp</a></p> <p><strong> </strong></p> <p dir="ltr">Follow Lon:</p> <p dir="ltr">X: <a href= "https://x.com/lons">https://x.com/lons</a></p> <p><strong> </strong></p> <p dir="ltr">Follow Jason:</p> <p dir="ltr">X: <a href= "https://twitter.com/Jason">https://twitter.com/Jason</a></p> <p dir="ltr">LinkedIn: <a href= "https://www.linkedin.com/in/jasoncalacanis">https://www.linkedin.com/in/jasoncalacanis</a></p> <p><strong> </strong></p> <p dir="ltr">Thank you to our partners:</p> <p dir="ltr">(0:00) PARTNER - AD BLURB</p> <p dir="ltr">(0:00) PARTNER - AD BLURB</p> <p dir="ltr">(0:00) PARTNER - AD BLURB</p> <p dir="ltr">Check out all our partner offers: <a href= "https://partners.launch.co/">https://partners.launch.co/</a></p> <p><strong> </strong></p> <p dir="ltr">Great TWIST interviews: <a href= "https://youtu.be/pvJa2pzuXWQ">Will Guidara,</a> <a href= "https://youtu.be/9dHN4YFkgv4">Eoghan McCabe</a>, <a href= "https://podcasts.apple.com/us/podcast/reddit-ceo-steve-huffman-on-mod-revolt-building-a/id315114957?i=1000617333424"> Steve Huffman</a>, <a href= "https://podcasts.apple.com/ca/podcast/airbnb-ceo-brian-chesky-on-early-rejection-customer/id315114957?i=1000611761112"> Brian Chesky</a>, <a href="https://youtu.be/y2UMzSqX94Q">Bob Moesta,</a> <a href= "https://podcasts.apple.com/ca/podcast/box-ceo-aaron-levie-breaks-down-box-ai-and-generative/id315114957?i=1000612384545"> Aaron Levie</a>, <a href= "https://podcasts.apple.com/ca/podcast/sophia-amoruso-on-branding-raising-a-fund-portfolio/id315114957?i=1000601352978"> Sophia Amoruso</a>, <a href= "https://podcasts.apple.com/ca/podcast/reid-hoffman-on-ais-crescendo-moment-regulation-and/id315114957?i=1000612548498"> Reid Hoffman</a>, <a href= "https://podcasts.apple.com/ca/podcast/snowflake-ceo-frank-slootman-on-moving-the-needle-win/id315114957?i=1000602560622"> Frank Slootman</a>, <a href= "https://podcasts.apple.com/ca/podcast/billy-mcfarland-on-fyre-fest-fraud-failure-hacking/id315114957?i=1000610922577"> Billy McFarland</a></p> <p><strong> </strong></p> <p dir="ltr">Check out Jason's suite of newsletters: <a href= "https://substack.com/@calacanis">https://substack.com/@calacanis</a></p> <p><strong> </strong></p> <p dir="ltr">Follow TWiST:</p> <p dir="ltr">Twitter: <a href= "https://twitter.com/TWiStartups">https://twitter.com/TWiStartups</a></p> <p dir="ltr">YouTube: <a href= "https://www.youtube.com/thisweekin">https://www.youtube.com/thisweekin</a></p> <p dir="ltr">Instagram: <a href= "https://www.instagram.com/thisweekinstartups">https://www.instagram.com/thisweekinstartups</a></p> <p dir="ltr">TikTok: <a href= "https://www.tiktok.com/@thisweekinstartups">https://www.tiktok.com/@thisweekinstartups</a></p> <p dir="ltr">Substack: <a href= "https://twistartups.substack.com">https://twistartups.substack.com</a></p>
- ▶ Listen
My First Million
3 strangers showed us how they made $8M, $10M, & $40M/year140+ real business ideas database: https://clickhubspot.com/pkst Episode 852: Sam Parr ( https://x.com/theSamParr ) and Shaan Puri ( https://x.com/ShaanVP ) ask 3 founders to tell them the juiciest number behind their businesses and get advice live. — Show Notes: (0:00) Intro (1:31) Raav Gupta, Posha (20:03) Nick Saltarelli, Mid-Day Squares (39:48) Shreyas Parab, DayDream Dental — Links: • Posha - https://www.posha.com/ • Mid-Day Squares - https://www.middaysquares.com/ • DayDream Dental - https://www.daydream.dental/ — Check Out Sam's Stuff: • Hampton (joinhampton.com): My community for founders. Average member does $25m/year. Many of the guests are members. Get after it...apply: http://joinhampton.com/mfm — Check Out Shaan's Stuff: • Shaan's weekly email - https://www.shaanpuri.com • Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents. • Mercury - Shaan uses Mercury across all of his companies. you can too: http://mercury.com/ Mercury is a fintech company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., Members FDIC • I run all my newsletters on Beehiiv and you should too + we're giving away $10k to our favorite newsletter, check it out: beehiiv.com/mfm-challenge My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano /
▶ ListenAcquiring Minds
From $700k Purgatory to $3m: A Mosquito Joe Update<p>Neil Finneran returns 3 years after buying a business so small it barely paid him a salary — now on pace for $800k.</p><p>Register for the webinars: </p><ul><li><a href="https://bit.ly/4qg4P9k">Learn to Avoid the #1 Reason Acquisitions Fail </a>- TODAY!! - https://bit.ly/4qg4P9k</li><li><a href="https://bit.ly/4wTADDf">Licenses & Regulatory Issues When Buying a Business</a> - Tue, Aug 25 - https://bit.ly/4wTADDf</li></ul><p>Topics in Neil’s interview:</p><ul><li>Neil’s previous appearance on Acquiring Minds</li><li>His background in hedge funds</li><li>Pain of buying small</li><li>Managing labor and no-shows</li><li>Implementing a hybrid-pay model for techs</li><li>The acquisition that tripled his revenue</li><li>Christmas lights services in the off season</li><li>Rising customer acquisition costs</li><li>Barriers to entry in pest control</li><li>Why his outcome diverged from Jesse Sunquist’s</li></ul><p>References and how to contact Neil:</p><ul><li><a href="https://www.linkedin.com/in/neil-finneran-1645653/">LinkedIn</a></li><li><a href="https://mosquitojoe.com/locations/massachusetts/andover/">Mosquito Joe of Andover-Peabody</a></li><li>Neil’s first appearance on Acquiring Minds: <a href="https://www.youtube.com/watch?v=lKjMbnoVLrM">How to Survive Going from Hedge Funds to SMB Owner</a></li><li>Jesse’s most recent appearance on Acquiring Minds: <a href="https://www.youtube.com/watch?v=-LwFYItoVm8">3 Years, $80k In: An Honest Update</a></li><li>Jesse’s first appearance on Acquiring Minds: <a href="https://www.youtube.com/watch?v=qnUXL8eoJsA">How to Widen Your Search to Buy a Business</a></li></ul><p>Work with an SBA loan team focused exclusively on helping entrepreneurs buy businesses:</p><ul><li><a href="https://bit.ly/43gVGBX">Pioneer Capital Advisory</a></li></ul><p>Get a complimentary IT audit for acquisition diligence or post-close transition.</p><ul><li>Visit <a href="http://www.inzotechnologies.com/eta?utm_source=acquiringminds&utm_medium=referral">inzotechnologies.com/eta</a>.</li></ul><p>Contact Jenny to learn how Engage can run people operations in your acquisition:</p><ul><li>Jenny Thear: <a href="mailto:[email protected]">[email protected]</a></li></ul><p>Connect with Acquiring Minds:</p><ul><li>See past + future interviews on the <a href="https://www.youtube.com/c/AcquiringMinds">YouTube channel</a></li><li>Connect with host <a href="https://www.linkedin.com/in/willsmithsf/">Will Smith on LinkedIn</a></li><li>Follow <a href="https://twitter.com/whentheresawill">Will on Twitter</a></li></ul><p>Edited by Anton Rohozov and produced by Pam Cameron</p>
▶ ListenThe Koerner Office - Business Ideas and Deep Dives with Chris Koerner
The Most Hands-Off $6K/Month Side Hustle to Start - Ep. #330<p>Check out my newsletter at <a href="https://tkopod.com/">https://TKOPOD.com</a> and join my community at <a href="https://tkowners.com/">https://TKOwners.com</a></p><p>━</p><p></p><p>I sat down with <strong>Nathan</strong> to break down his surprisingly simple <strong>trailer rental business</strong>. He runs it alongside a full-time job, spends only a few hours a week on it, and is now making around <strong>$4,000 a month in profit</strong>. We talked about how he bought his first trailers, automated almost the entire rental process, finds customers through <strong>Google and Facebook Marketplace</strong>, and which trailers he would buy first if he were starting over. We also get into how you can test demand in your own area before going all in. Check out <strong>Lanco Trailer Rentals</strong> here: <a href="https://lancotrailers.com/">https://lancotrailers.com/</a></p><p><br></p><p><br></p><p>Enjoy!</p><p>---</p><p>Watch this on <strong>YouTube</strong> instead here: <a href="https://www.youtube.com/@thekoerneroffice?sub_confirmation=1">tkopod.co/p-yt</a></p><p><strong>Ask me a question</strong> on or off the show here: <a href="http://tkopod.co/p-ask">http://tkopod.co/p-ask</a></p><p>Learn more about <strong>me:</strong> <a href="http://tkopod.co/p-cjk">http://tkopod.co/p-cjk</a></p><p>Learn about <strong>my company: </strong><a href="http://tkopod.co/p-cof">http://tkopod.co/p-cof</a></p><p>Follow me on <strong>Twitter</strong> here: <a href="http://tkopod.co/p-x">http://tkopod.co/p-x</a></p><p><a href="http://tkopod.co/p-x"></a>Free weekly <strong>business ideas newsletter:</strong> <a href="http://tkopod.co/p-nl">http://tkopod.co/p-nl</a></p><p><strong>Share this podcast:</strong> <a href="http://tkopod.co/p-all">http://tkopod.co/p-all</a></p><p><strong>Scrape</strong> small <strong>business data:</strong> <a href="http://tkopod.co/p-os">http://tkopod.co/p-os</a></p><p><a href="http://tkopod.co/p-os"></a>---</p><p></p>
▶ ListenFounders Podcast
How a Tiny Dublin Startup Sold for $425M<p>Most founders overlook a simple but powerful secret—protecting their ideas with the right legal strategies can turn a modest startup into a multimillion-euro exit. In this episode, Phil Crowley reveals how a Dublin-based AI startup turned a $500 million acquisition, sharing the tactical legal moves that fueled their journey from code to collapse and rebirth.You'll discover how early-stage founders can leverage intellectual property, patents, and strategic legal protections to safeguard their innovations without breaking the bank. Phil breaks down the true value of patents versus trade secrets in software, explains why a limited liability company setup is critical, and offers practical advice on avoiding personal liability traps that could derail your startup.We also explore the often-missed legal vulnerabilities that even successful founders regret ignoring—like improper IP assignments or neglecting formalized agreements with collaborators. Phil shares real-world anecdotes, including a $425 million sale, and distills crucial lessons on building a legally resilient business foundation.Why does neglecting legal infrastructure cost startups millions in lost value or legal trouble? Because in today’s fast-moving tech landscape, protecting your "secret sauce" isn’t just good practice—it's a game changer. If you're an early-stage founder or planning your next fundraising round, this episode arms you with the knowledge to shield your innovation and accelerate your growth confidently.Perfect for entrepreneurs looking to unlock legal strategies that build lasting value, or for anyone curious about how legal foresight can turn a modest idea into a thriving, protected business—this is your blueprint to avoid common pitfalls and claim your rightful share of success.Phil Crowley is Managing Partner at Crowlew Law, known for guiding tech startups through complex legal terrain from Dublin to New York, and for helping them secure millions through strategic IP and legal protections.</p>
- ▶ Listen
Acquiring Minds
The Ferrari of Signage: $9.5m Pipeline in 6 Months<p>Andrew Sova and Alex Clark revived sales at a 40-year-old sign manufacturer, the first acquisition of their holdco.</p><p>Register for the webinars:</p><ul><li><a href="https://bit.ly/4hGNwMi">New SBA Rules: What Business Buyers Need to Know </a>- TODAY!! - https://bit.ly/4hGNwMi</li><li><a href="https://bit.ly/4qc7dxx">Architecture of an Entrepreneurial Roll-Up</a> - Tue, Sep 1 - https://bit.ly/4qc7dxx</li></ul><p>Topics in Andrew & Alex’s interview:</p><ul><li>Meeting at BCG</li><li>Partnership provided accountability and motivation</li><li>Looking for direct-impact roles</li><li>Prioritizing speed with brokered search</li><li>Their vision to build a holdco</li><li>Winsor Fireform makes uniquely durable signage</li><li>Employee growth = key success metric</li><li>Seller chose buyers based on trust, not price</li><li>Customers include parks, transit systems, and stadiums</li><li>Long negotiation over working capital</li></ul><p>References and how to contact Andrew and Alex:</p><ul><li><a href="https://www.linkedin.com/in/andrewsova/">Andrew Sova’s LinkedIn</a></li><li><a href="https://www.linkedin.com/in/alexandersclark/">Alex Clark’s LinkedIn</a></li><li><a href="https://www.novofoundry.com/">Novo Foundry</a></li><li><a href="https://caynecrossing.com/">Cayne Crossing</a></li><li><a href="https://www.winsorfireform.com/">Winsor Fireform</a></li><li><a href="https://www.pioneercapitaladvisory.com/">Pioneer Capital Advisory</a></li></ul><p>Get a complimentary IT audit for acquisition diligence or post-close transition.</p><ul><li>Visit <a href="http://www.inzotechnologies.com/eta?utm_source=acquiringminds&utm_medium=referral">inzotechnologies.com/eta</a>.</li></ul><p>Contact Jenny to learn how Engage can run people operations in your acquisition:</p><ul><li>Jenny Thear: <a href="mailto:[email protected]">[email protected]</a></li></ul><p>Get complimentary due diligence on your acquisition's insurance & benefits program:</p><ul><li><a href="https://bit.ly/3W6QqNx">Oberle Risk Strategies - Search Fund Team</a></li></ul><p>Connect with Acquiring Minds:</p><ul><li>See past + future interviews on the <a href="https://www.youtube.com/c/AcquiringMinds">YouTube channel</a></li><li>Connect with host <a href="https://www.linkedin.com/in/willsmithsf/">Will Smith on LinkedIn</a></li><li>Follow <a href="https://twitter.com/whentheresawill">Will on Twitter</a></li></ul><p>Edited by Anton Rohozov and produced by Pam Cameron</p>
- ▶ Listen
Acquiring Minds
3 Years, $80k In: An Honest Update<p>Jesse Sunquist put a GM in charge and stepped back to 5 hours a week — proud of the experience, restless about the outcome.</p><p>Register for the webinar: </p><ul><li><a href="https://bit.ly/4wPHY6R">Learn to Avoid the #1 Reason Acquisitions Fail </a>- Thu, Aug 13 - https://bit.ly/4wPHY6R</li></ul><p>Topics in Jesse’s interview:</p><ul><li>Buying a business for flexibility</li><li>Geographical search in New Jersey</li><li>Lowering his minimum SDE threshold to $300K</li><li>Acquiring 2 Mosquito Joe territories</li><li>His plan to build wealth through franchise roll-ups</li><li>Modest growth followed by shrink</li><li>How other owners handle the off-season</li><li>Taking a W2 with the intent to sell</li><li>Inability to find a buyer</li><li>Hiring a great GM to run it</li></ul><p>References and how to contact Jesse:</p><ul><li><a href="https://www.linkedin.com/in/jesse-sunquist/">LinkedIn</a></li><li><a href="https://franchise.neighborly.com/mosquito-joe">Mosquito Joe</a></li><li>Jesse’s previous interviews on Acquiring Minds:</li></ul><p>#1<a href="https://acquiringminds.co/articles/jesse-sunquist-full-time-searcher?utm_source=chatgpt.com"> </a><a href="https://www.youtube.com/watch?v=MI05YHbbalw">Reflections After 1 Year of Searching Full Time</a></p><p>#2<a href="https://podcasts.apple.com/us/podcast/a-reward-for-widening-search-to-%24300k-sde/id1569715379?i=1000631442171&utm_source=chatgpt.com"> </a><a href="https://www.youtube.com/watch?v=qnUXL8eoJsA">A Reward for Widening Search to $300k SDE</a></p><ul><li>Neil Finneran on Acquiring Minds: <a href="https://www.youtube.com/watch?v=lKjMbnoVLrM">How to Survive Going from Hedge Funds to SMB Owner</a></li></ul><p>The ecosystem for serious acquisition entrepreneurs—education, capital, community, and post-close support to buy and grow a business:</p><ul><li><a href="https://bit.ly/3JPAYQI">The Acquisition Lab</a></li></ul><p>Get complimentary due diligence on your acquisition's insurance & benefits program:</p><ul><li><a href="https://bit.ly/3W6QqNx">Oberle Risk Strategies - Search Fund Team</a></li></ul><p>Get a free review of your books & financial ops from System Six (a $500 value):</p><ul><li><a href="https://landing.systemsix.com/acquire">Book a call with Tim</a> or <a href="mailto:[email protected]">[email protected]</a> and mention Acquiring Minds</li></ul><p>Connect with Acquiring Minds:</p><ul><li>See past + future interviews on the <a href="https://www.youtube.com/c/AcquiringMinds">YouTube channel</a></li><li>Connect with host <a href="https://www.linkedin.com/in/willsmithsf/">Will Smith on LinkedIn</a></li><li>Follow <a href="https://twitter.com/whentheresawill">Will on Twitter</a></li></ul><p>Edited by Anton Rohozov and produced by Pam Cameron</p>
- ▶ Listen
Acquiring Minds
40 Schools to 130: The Roll-Up 2 Years Later<p>Jeff Homer returns with an update: revenue past $100m, a new dance division, and 50% growth expected this year. </p><p>Register for the webinars:</p><ul><li><a href="https://bit.ly/4ccatTW">Licenses & Regulatory Issues When Buying a Business </a>- TOMORROW! - https://bit.ly/4ccatTW</li><li><a href="https://bit.ly/4c3b6zj">New SBA Rules: What Business Buyers Need to Know</a> - Thu, Aug 27 - https://bit.ly/4c3b6zj</li><li><a href="https://bit.ly/4zdTbj2">Architecture of an Entrepreneurial Roll-Up</a> - Tue, Sep 1 - https://bit.ly/4zdTbj2</li></ul><p>Topics in Jeff’s interview:</p><ul><li>Building a music school roll-up</li><li>Scaling through monthly acquisitions</li><li>Expanding into dance schools</li><li>Back-office value creation</li><li>Transitioning from operator to CEO</li><li>Building middle management</li><li>Avoiding private equity pitfalls</li><li>100x return for early investors</li><li>Constant travel as CEO</li><li>Future vision for Ensemble</li></ul><p>References and how to contact Jeff:</p><ul><li><a href="https://www.linkedin.com/in/jeff-homer-co/">LinkedIn</a></li><li><a href="https://www.ensembleschools.com/">Ensemble</a></li><li>Jeff’s first appearance on Acquiring Minds: <a href="https://www.youtube.com/watch?v=uu3DTmA56A8">How to Buy 40 Businesses in 4 Years</a></li><li>Webinar:<a href="https://us02web.zoom.us/webinar/register/WN_zDLr2bqGTESolVU2ZMYY9Q">Architecture of an Entrepreneurial Roll-Up</a></li></ul><p>Get a free review of your books & financial ops from System Six (a $500 value):</p><ul><li><a href="https://landing.systemsix.com/acquire">Book a call with Tim</a> or <a href="mailto:[email protected]">[email protected]</a> and mention Acquiring Minds</li></ul><p>The ecosystem for serious acquisition entrepreneurs—education, capital, community, and post-close support to buy and grow a business:</p><ul><li><a href="https://bit.ly/3JPAYQI">The Acquisition Lab</a></li></ul><p>Work with an SBA loan team focused exclusively on helping entrepreneurs buy businesses:</p><ul><li><a href="https://bit.ly/43gVGBX">Pioneer Capital Advisory</a></li></ul><p>Connect with Acquiring Minds:</p><ul><li>See past + future interviews on the <a href="https://www.youtube.com/c/AcquiringMinds">YouTube channel</a></li><li>Connect with host <a href="https://www.linkedin.com/in/willsmithsf/">Will Smith on LinkedIn</a></li><li>Follow <a href="https://twitter.com/whentheresawill">Will on Twitter</a></li></ul><p>Edited by Anton Rohozov and produced by Pam Cameron</p>
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My First Million
3 millionaires reveal their super niche businesses30+ unsexy business ideas: https://clickhubspot.com/dwtb Episode 854: Sam Parr ( https://x.com/theSamParr ) and Shaan Puri ( https://x.com/ShaanVP ) ask 3 founders to tell them the juiciest number behind their businesses and get advice live. — Show Notes: (0:00) Rishi Talati, Hot Plate (20:10) Ajay Mehta, Tolan (39:53) Jonathan Baer, Overlap — Links: • Hot Plate - https://www.hotplate.com/ • Tolan - https://www.tolans.com/ • Overlap - https://overlap.ai/ — Check Out Sam's Stuff: • Hampton (joinhampton.com): My community for founders. Average member does $25m/year. Many of the guests are members. Get after it...apply: http://joinhampton.com/mfm — Check Out Shaan's Stuff: • Shaan's weekly email - https://www.shaanpuri.com • Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents. • Mercury - Shaan uses Mercury across all of his companies. you can too: http://mercury.com/ Mercury is a fintech company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., Members FDIC • I run all my newsletters on Beehiiv and you should too + we're giving away $10k to our favorite newsletter, check it out: beehiiv.com/mfm-challenge My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano /
▶ ListenSoftware Engineering Daily
AI and the New Global Security Landscape<p class="wp-block-paragraph">The conversation about AI often focuses on software, automation, and the race between attackers and defenders in code. However, some of the most consequential risks lie further afield, in domains where a mistake is measured in human lives. Advanced models can now offer step-by-step guidance toward chemical and biological weapons, and militaries are already folding AI into targeting and battlefield assessments. These are no longer speculative fears confined to the AI doomer crowd. They are documented in red team disclosures, government legislation, and events unfolding on real battlefields.</p> <p class="wp-block-paragraph"><a href="https://www.cfr.org/experts/gordon-m-goldstein">Gordon M. Goldstein </a>is an adjunct senior fellow at the <a href="https://www.cfr.org/">Council on Foreign Relations</a>, where he focuses on the convergence of technology and US foreign policy. He previously spent nearly a decade as a managing director at Silver Lake, and he is the author of Lessons In Disaster: McGeorge Bundy and the Path to War in Vietnam, which is a study of national security strategy and White House decision-making. In this episode, Gordon joins Kevin Ball to discuss the credibility of AI-enabled chemical and biological weapon threats, the ad hoc safeguards meant to contain them, and the rise of autonomous warfare and its implications for human control and nuclear deterrence. Gordon speaks on his own behalf, not on behalf of the Council on Foreign Relations.<br><br>Sponsorship inquiries:<br><a href="mailto:[email protected]">[email protected]</a></p> <p>The post <a href="https://softwareengineeringdaily.com/podcasts/ai-and-the-new-global-security-landscape/">AI and the New Global Security Landscape</a> appeared first on <a href="https://softwareengineeringdaily.com">Software Engineering Daily</a>.</p>
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