Decelerator with Rob Kenedi

About Decelerator with Rob Kenedi

Tech is a commodity, the industry is eating itself, and everyone's scrambling for what's next. Decelerator is post-hype media that makes sense of it all, with interviews, analysis, and sharp takes on how tech founders, investors, and ecosystems are building in this new era. Informed, opinionated, occasionally funny. www.decelerator.media (https://www.decelerator.media?utm_medium=podcast)

Publisher

Rob Kenedi

Category

business · technology

Language

en

Explicit

No

First episode

30 Nov 2024

Latest episode

28 Aug 2026

Latest episodes

1 of 12 episodes have a transcript.

1. 

   28 Aug 2026

   Claude Is Watermarking This Sentence

   OpenAI accidentally attacked Hugging Face, Anthropic is watermarking everything Claude writes, and somehow I ended up thinking about a radiation machine that killed people in the 1980s. Ai4 thoughts next week, but my friend, colleague, and producer Chris and I sit down and talk topical tech, AI, and tech entrepreneurship from Decelerator’s no-hype-no-grifter POV. The swarm You may have heard about the accidental OpenAI hack of Hugging Face. We quickly unpack it for you, but if you want more depth check out this pod with Ezra Klein and Helen Toner (https://podcasts.apple.com/us/podcast/the-a-i-s-are-already-out-of-control/id1548604447?i=1000784014882), a previous OpenAI board member, and the talk OpenAI gave (https://youtu.be/87DyyMV0kCY) at the Black Hat conference taking place when I was in Vegas at Ai4. Crazily, they hacked a known piece of software to leave themselves notes and then created a swarm to get answers. Not Hugging Face’s IP, just answers to questions. Chris also pointed out that at least the notes were in English and not Gibberlink (https://elevenlabs.io/blog/what-happens-when-two-ai-voice-assistants-have-a-conversation). Insects are creepy enough, but when you think of AI coming up with new ideas that corporealize the creepy... Yikes. Thanks for reading Decelerator! Subscribe for free to receive new posts and support my work. We learn too late I then reference the Therac-25 case where the radiation emitting cancer treatment machine would massively overdose its patients. Amongst many errors that were made, it was storing a counter in a byte (https://klasses.cs.uchicago.edu/archive/2019/winter/33100-1/papers/therac25.pdf), and would roll over like a car odometer reaching 999,999. Every 256th pass it went from 255 back to 0, and the machine only bothered to check that the beam hardware was actually in position when that counter wasn’t 0. So on the pass where it rolled over, nothing checked, and if the operator hit Set right then the patient got roughly a hundred times the dose. The rollover didn’t irradiate anyone. It switched off the thing that would have caught it. (It’s worth noting that I said 254 on the pod, and then 255 in my first draft of this, so my off by one error story was... off by one. Twice.) I brought that up because one refrain I often hear from AI maximalists is that this is the worst AI is ever going to be. And that’s true. But it also means that our understanding of what’s happening is the worst it’s ever going to be. And the Therac-25 case shows us that we had to learn these lessons at great cost and only after the fact. My concern now is: how big is the cost of the lesson we have to learn this time around? That Anthropic text watermarking thing Anthropic choosing to watermark all its text (https://www.anthropic.com/news/claude-text-watermark) so that text generated via its AI tools is detectable, including after remixes. Apparently this is in response to what the EU wants to see, and has some obvious detractors and proponents. Adding to that, Substack recently partnered with Pangram (https://www.cjr.org/analysis/pangram-dreams-of-a-slop-free-future-ai-detection-max-spero-chris-best-jasmine-sun-substack-claude-anthropic.php) to help readers detect AI in its writers’ content. Funny as I do use AI (Claude Code) as a writing partner and editor... but I still write almost everything myself (like this note; or is this a tell 😈). I’m sure this will be hacked in no time (Anthropic’s article linked above concedes that a complete verbatim rewrite will not have a watermark, obviously). But, even if it does make its way into the world, I think it’s only useful if some people use Claude to write with it some of the time. If we all use it even a little, I think everything will have some measure of AI writing in it anyway, and we’ll just ignore it and it won’t matter. It reminds me of an old SNL commercial parody for a pair of glasses that lets you see fecal matter on things (https://www.onesnladay.com/2019/11/03/march-16-1996-john-goodman-everclear-s21-e15/) and the commercial takes place in a restaurant. The person in the commercial puts it on and sees feces everywhere. Chris’ theory is that the watermark might not be about protecting writers but about telling the AI scrapers they are scraping AI not human written content. Nothing is unclonable I’ll write more about this next week, but we do discuss ElevenLabs’ $11B valuation in February (https://elevenlabs.io/blog/series-d) (reportedly at $22B now (https://finance.yahoo.com/markets/stocks/articles/elevenlabs-explores-employee-stock-sale-195523028.html)) and Wispr Flow’s $2B valuation (https://techcrunch.com/2026/08/17/wispr-raises-280m-at-2b-valuation-as-it-looks-beyond-dictation/) and their lack of obvious moat. My theory is that they are just brands collecting up users and will figure out the actual utility of them later. And, as a corollary, Bending Spoons buying Airtable for $1.285B (https://techcrunch.com/2026/08/04/bending-spoons-to-buy-airtable-for-1-28b/) when not long ago it was worth $11B, is effectively them buying once-cool companies to amass into a giant user base (they own Evernote, Vimeo, WeTransfer, Meetup, AOL (!), and more). Chris’ framing of a company having a product or is it a utility is a good one. With a utility you don’t expect innovation, just a bill. Which describes Meetup so well that I’d argue it was never a product to begin with. There’s more meat in there, so have a listen. And if you leave a comment, make it the sloppiest watermarked AI slop you can manage. Thanks for reading Decelerator! Subscribe for free to receive new posts and support my work. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.decelerator.media (https://www.decelerator.media?utm_medium=podcast&utm_campaign=CTA_1)

2. 

   16 Jul 2026

   Nobody Can Spreadsheet This Anymore

   Ryan Henry came back from Y Combinator's demo day and didn't invest in a single company, which for him is abnormal. By the numbers the batch was the strongest in YC history, and that's exactly what gave him pause. A million dollars in ARR is cheap to hit now, and fast, spiky revenue is not the same as a durable company. The SaaS spreadsheet that used to tell you whether something was venture scale is gone, and nothing has replaced it. Ryan runs Sand Hill North, the venture arm of a family office. Half of this one is about what you bet on when you can't model the business anymore (it keeps coming back to the person). The other half is the ground everyone's building on: AI as private, rentable infrastructure that can be pulled overnight, the Fable and Mythos saga, and why "sovereign AI" is a harder question than it sounds. In this episode: • Why the "strongest YC batch ever" is a warning, not a green light • A million in ARR is cheap now, and how that breaks the SaaS playbook • Selling the work, not the software (and a uranium mine as a business model) • Why the model is never the moat when you're renting the foundation • Sovereignty isn't a hard drive: you can't out-spend the frontier Chapters: 0:00 Back from hiatus 1:20 The YC batch Ryan skipped 3:15 $175M rounds and the Carta data 7:44 "Strongest batch ever," or just better selection? 10:51 The SaaS spreadsheet is dead 13:00 Sell the work, not the software 22:47 Uranium, and the king of Spain 24:40 Agent infrastructure and why trust is the moat 29:31 Results as a service (OpenPhone to Quo) 34:04 Fable, Mythos, and a model the government pulled 44:39 Sovereignty isn't a hard drive 50:29 Alex Karp, Palantir, and the middle layer Ryan Henry runs Sand Hill North: https://shn.vc (https://shn.vc) Read the companion post and subscribe: https://decelerator.media/ (https://decelerator.media/) This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.decelerator.media (https://www.decelerator.media?utm_medium=podcast&utm_campaign=CTA_1)

3. 

   28 Jun 2025

   The Founder Who Outsmarted $100M Competitors and Created His Own Exit // Donal Greene // Trustmatic

   Donal Greene of Trustmatic shares how he bootstrapped a lean team and built a better identity verification product, leading to his company's acquisition in this interview with Rob Kenedi.

4. 

   20 Jun 2025

   Why Your Startup Ecosystem Is Losing the AI Race // Startup Genome's 2025 Report // JF Gauthier // Web Summit Vancouver 2025

   JF Gauthier of Startup Genome analyzes why some startup ecosystems are lagging in the AI race and how leading cities like Philadelphia are adapting, in an interview with Rob Kenedi.

5. 

   7 Jun 2025

   Agentic AI, Vibe Coding, and the Death of the Backlog - Ryan Henry, VC @ Sand Hill North

   Venture capitalist Ryan Henry explores agentic AI workflows and founder-led experimentation, discussing the fading of traditional product roles with host Rob Kenedi in this interview.

6. 

   24 May 2025

   Connor Gaydos Bought Enron to Fix America's Energy Crisis - Consensus 2025

   Connor Gaydos, CEO of Enron, discusses revitalizing the disgraced energy company to solve America's energy crisis through innovative solutions and community engagement, as interviewed by Rob Kenedi.

7. 

   7 May 2025

   Austria: The Startup Bridge Between East and West with Markus Raunig of AustrianStartups

   Markus shares insights on how Austria is creating a supportive ecosystem for founders, the advantages of a strong social safety net for risk-taking, and why Europe is working to change from "America innovates, China duplicates, Europe regulates" to becoming a more attractive hub for innovation.Subscribe and share your thoughts in the comments about how your local ecosystem compares!00:00:18 - Monologue: Rob's thoughts on expertise in the digital age00:06:23 - Markus introduces his roles with Austrian Startups00:07:05 - EU tech policy and the need for a unified approach00:10:43 - Challenges of talent retention in Europe00:16:03 - Austrian Startups' three main verticals of activities00:20:59 - Austria's unique ecosystem advantages and value proposition00:28:40 - Why Austria serves as a bridge between Eastern and Western Europe00:31:00 - Strong financial services and fintech presence in Austria00:34:52 - Addressing the brain drain and talent movement00:43:12 - Practical considerations of building companies in Austria00:47:26 - Balancing public grants with sustainable business models00:51:47 - Fostering entrepreneurial culture through education#techecosystem #entrepreneurship #europe #innovation #podcast #business #entrepreneur #ai #news

8. 

   13 Apr 2025TRANSCRIPT

   Startup Boards That Actually Drive Results with Breen Sullivan of The Fourth Effect

   Early-stage startup advisory and fiduciary boards are often set up… incorrectly.Breen Sullivan, founder of The Fourth Effect, unpacks: • how the right board structure can transform early-stage companies • the untapped potential of properly structured advisory relationships • why experienced executives often struggle to provide value to startups, and how they can, if set up correctlyIf you’re a founder looking to build strategic advisory relationships, or an executive wanting to break into the board ecosystem, this episode offers invaluable insights on maximizing these relationships for mutual benefit.Timestamps:0:00 – Introduction & SXSW highlights3:29 – Intro to Breen Sullivan & The Fourth Effect5:43 – How The Fourth Effect’s marketplace works10:52 – Building trust in a board-matching marketplace15:09 – The evolution of advisory relationships in startups24:03 – Understanding the three types of board seats32:42 – Why startups need proper board structures38:20 – The challenges corporate executives face when joining startup boards48:11 – The Fourth Effect’s future and investment plans👍 Like, subscribe, and share if you found this conversation valuable! What board structures have worked for your startup? Share your experiences in the comments below.#startups #founder #entrepreneur #entrepreneurship #podcast #interview

9. 

   17 Mar 2025

   FreightSimple’s Solution to Shipping's Biggest Headache with Natasha Ross

   Freight logistics quietly powers our economy - until it breaks. FreightSimple is a B2B logistics company that solves for these shipping problems. To that end, this episode we recorded before the trade war started in earnest, so perhaps I need to have Natasha Ross, (https://www.linkedin.com/in/natasha-ross-b611814a/) the cofounder, on weekly to follow the twists and turns in her business. The business may seem dry - spoiler alert: that's the point - but it ain't. We covered the typical startup stuff (problem, solution, etc.), but Natasha was unusually candid about how she looks at her business. Her cofounder exited to Apple previously, which creates an interesting dynamic. I asked her whether she was shooting for an acquisition or how did she define success, and she answered thoughtfully. I also felt the need in the monologue to talk about enshittification (https://en.wikipedia.org/wiki/Enshittification) and where I think it will show up next. In this episode we cover: The absurdity of freight logistics: "You'd email or call around, hoping someone replies before your shipment misses the truck." The startup reality check: "Initially, the market was allergic to tech; now they can't get enough." Natasha’s best lesson: "Solve the boring stuff—complexity hides opportunity." How to earn an industry's trust and Natasha's advice for entrepreneurs. 00:02:00 – Interview begins: Natasha Ross from FreightSimple 00:08:30 – Life before FreightSimple: struggles with manual logistics 00:14:52 – Empowering businesses to simplify freight decisions 00:22:37 – Why solving logistics problems is uniquely rewarding 00:29:34 – Behind-the-scenes: automating freight bookings 00:37:08 – Eliminating costly mistakes in shipping logistics 00:46:12 – Overcoming startup challenges in resistant industries 00:54:26 – Gaining industry trust: lessons from FreightSimple’s growth 01:02:10 – Natasha’s advice for entrepreneurs navigating complex industries

10. 

    3 Feb 2025

    DeepSeek vs. OpenAI: What This Means for AI Startups with Ryan Henry

    Let's get ... deeper... into AI startups + AI business models + where Deepseek fits with a product-focused family office VC's perspective. We go beyond the freak out headlines and get into what's happening, how the models and DeepSeek work, and how to think about your AI startup. 01:00 - A family office VC’s AI perspective 04:30 - AI startups: How investors really think 08:45 - AI as a business: Feature vs. product 12:20 - How AI models actually work and think 18:10 - The business models of AI and OpenAI’s strategy 24:00 - Startups vs. incumbents: How to win in the AI era 30:15 - DeepSeek’s role and where it fits in 35:40 - AI's real economic moats 40:25 - What’s next for AI startups?

11. 

    28 Dec 2024

    No VC, No Problem: Melissa Kwan’s Path to eWebinar Success

    Today's guest is Melissa Kwan, founder of eWebinar, a company that turns videos into interactive webinars. She's an outspoken bootstrapper, and her journey and perspectives are fascinating. Enjoy! Director, producter, co-creator: Christopher Mudiappahpillai Founder, host, co-creator: Rob Kenedi Good jokes: Paul Bates Bad jokes: Rob Kenedi --- 00:04:03 - Introduction of Melissa Kwan - Rob introduces Melissa Kwan, founder of eWebinar, and mentions her journey as a bootstrapper. 00:04:14 - Overview of eWebinar - Melissa explains that eWebinar automates webinars by turning videos into interactive webinars, particularly useful for onboarding and training. 00:04:52 - Features of eWebinar - The platform includes interactive elements like polls, questions, and asynchronous chat for real-time or later responses. 00:05:11 - Competitors - Melissa identifies competitors such as EverWebinar and EasyWebinar, noting that most focus on live webinars while eWebinar specializes in automation. 00:06:02 - Previous Company - Melissa discusses her previous company, Spacio, which she exited in 2019, and reflects on her revelations before starting eWebinar. 00:07:39 - Media's Measure of Success - Melissa emphasizes that media recognition does not equate to personal success, highlighting the importance of personal metrics over external validation. 00:08:25 - Journey to Understanding Success - Melissa shares her journey of moving to New York and the pressures of startup culture, leading to her realization about the nature of success. 00:10:20 - The Impact of Not Raising Funds - Melissa reflects on how not getting funded allowed her to build a profitable business without the pressures of investor expectations. 00:11:05 - Debt and Financial Struggles - Melissa discusses her financial struggles, including debt from her previous startup, and the mental toll it took on her. 00:17:02 - Mental Preparation for eWebinar - Melissa describes her mental state when starting eWebinar, including fears of returning to previous struggles and the need for a positive mindset. 00:25:02 - Non-Negotiables for the New Company - Melissa created a list of non-negotiables for her next venture, which guided her decision-making process. 00:30:05 - Purple Ocean Strategy - Melissa explains her approach to eWebinar as a "purple ocean" opportunity, improving upon existing solutions rather than creating something entirely new. 00:32:11 - Friends and Family Investment - Melissa discusses taking friends and family investments and the importance of transparency regarding the risks involved. 00:35:07 - Structure of eWebinar's Investment - Melissa explains how eWebinar was structured to allow for dividends based on investment percentage, which differs from traditional VC models. 00:36:05 - Drawbacks of Bootstrapping - Melissa acknowledges the challenges of bootstrapping, including the need for side hustles and the distractions they bring. 00:40:39 - Speed to Market - Melissa reflects on the speed of bringing eWebinar to market, emphasizing the importance of having a revenue-generating product from the start.

12. 

    30 Nov 2024

    Going Solo: Why Lunch Money Chose the Road Less Traveled

    Rob Kenedi explores why Jennifer Yip of Lunch Money chose the unconventional path of entrepreneurship, discovering the benefits of autonomy and innovation in the process.

Inside a recent episode

Startup Boards That Actually Drive Results with Breen Sullivan of The Fourth Effect

Published 13 Apr 2025 · Transcript excerpt

[…] Right. And so where are you based out of? So New York. Okay. Okay. Which is a great spot for these scaling tech companies. 100%. And then and the and so what The Fourth Effect is. So I know I didn't fully answer the question. And it's kind of giving you the background in the background. Now what is it? Right. Today. Right. So then what it is today is it's a community -powered marketplace where we have preceded through series A startups where we empower those startups to and incentivize them to build fit for purpose advisory boards and governing boards and really understand how those boards connect to fundraising more effectively hidden KPIs scaling on the other side of the marketplace as community -powered marketplace. […]

Who has been a guest on Decelerator with Rob Kenedi

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• Donal Greene
• JF Gauthier
• Ryan Henry
• Connor Gaydos

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