Harry Stebbings

If you want to start a company but don’t have “the idea”. 1. Find a large incumbent that is weak and outdated. 2. Find a segment of customers that is not their core target market. 3. Understand what that customer segment wants but the incumbent can’t provide them without harming the product for their core customer base. 4. Create the standalone product serving those features only, to that underserved base. If your 100% unwavering focus is someone else’s side project, your chances of winning; skyrocket.

You Will Die If You Make Software For Humans Not Agents: "If you are not making your software for autonomous agents today, you are going to be challenged in the future. You will be severely challenged if you still think human beings are going to buy your software." @aspenjfm How does software change when being designed for agents, not humans @dhh @biilmann @destraynor @zoink @scottbelsky

This episode took 8 years of convincing the guest to make it happen. I first met @aspenjfm at the Connaught Hotel to discuss a company we were co-investing in. I was 21 and had just raised my first fund. Jerry was one of the all-time greats, having led rounds into Twitter and managing $90BN for Insight. Today, after 8 years of friendship, I released our episode and have gone over it to condense my biggest learnings from the discussion. 1. The Shift from Assistants to Employees 🤖 We are moving beyond "copilots." Autonomous agents aren't just tools; they are becoming digital employees with identities, credentials, and the authority to make decisions. If you aren't building your software to be used by agents, you’re building for a shrinking market. 2. "Cursor is Obsolete" 💻 Native AI startups are already moving past current coding tools toward homemade autonomous agents that write code directly. In AI, you can’t think about yesterday; you have to build for where the puck is going. 3. The Rise of the "Claw Stack" 🏗️ Just as the LAMP stack fueled the 2004 web explosion, Jerry predicts a new "Claw Stack" for agents. This involves an orchestration layer that triages workflows—sending high-reasoning tasks to models like Claude and Gemini, while routing simpler tasks to cheaper open-source models like Llama. 4. ASIC Chips > General Compute? ⚡ NVIDIA is king today, but the future might belong to ASICs. As models become more specific to workloads, we’ll see models put directly onto cheaper, more tunable chips. This is why Meta is betting big on their own silicon—they’re preparing for the ASIC explosion. 5. Selling to Agents, Not Humans 💸 The buyer is changing. When agents start buying software, pricing must shift to consumption-based models. An agent doesn't care about a "seat license"; it cares about the compute and memory required to get the job done. 6. Intuition vs. Wishful Thinking 🧠 Jerry’s biggest misses? Confusing wishful thinking with intuition. He’s learned that the founders who make you feel "comfortable" are often the ones who let you down. The best founders are often socially challenged, obsessed, and possess a "sharp edge" that makes them win. 7. Money Has No Instructions ⚡ Money is simply energy. It doesn’t come with a manual. As an investor or founder, your job is to respect that energy—don't waste it on the "middle," use it to back the crazy ideas that have the power to change the world. (Link in Comments)

The brutal truth is that not one single public company has come out with a compelling agent product other than Palantir. Not one.

If you are having your PR advisor reach out in this media landscape, you really don’t understand media right now.

The majority of classified businesses are destroyed. They do not own the content. They are a thin discovery layer on top of a data repository. Rightmove and co will be worth 10% of what they are in 3 years. Bets on!

Which Segment Adopts Agents Fastest.... "I think we have to look at consumer, small business and enterprise, and my guess is enterprise is last. In this AI revolution they have been last, though they may catch up in a year or two. When enterprise adoption of autonomous agents happens, we are going to see dramatic change, and even minimal viable income may become a ballot question in a couple of years." @aspenjfm @Benioff @dharmesh @eoghan do you agree enterprise is the laggard and will labour displacement be a ballot question in the next election?

Is Cursor F*****? "Most of the companies I mentioned think Cursor is obsolete today. The team is really smart, they have a lot of money and customers, and they have time to pivot. But in AI you have to go where things are going, not where they were, and they will have to quickly embrace autonomous agents." @aspenjfm Love to hear your thoughts @kylebrussell @Suhail @AnjneyMidha @JTLonsdale @Mkclements @t_blom

Cursor is dead, Cursor is dead, Cursor is dead. Well can someone then explain to me how they are at $1.3BN in ARR closing the year at $2BN????

Sales teams today are way too cushy. Everyone wants to have their hand held and told they are doing great. Well, s*** is about to get real. I have interviewed 100 of the best sales leaders over the past 5 years. Chad Peets is the most no BS sales leader I have ever met. 🚀 8 Lessons on Building a $BN Sales Machine: 1. Hire for "Obsessed" Grit You need people who are "a little f**ked in the head"; those who wake up at 3:00AM thinking about work because they are genuinely obsessed with the mission. Chad prioritizes "grit" by asking candidates about the hardest challenges they've faced in life. He looks for military veterans or people who have navigated "serious shit" because startups are essentially life and death. 2. Hire for Today, Not Tomorrow A fatal mistake founders make is hiring a leader for the company they hope to be in 3 years, rather than the one they are today. Someone who managed a $500M business often knows nothing about building from 0 to $50M. If you hire for "tomorrow" before you have a foundation, you will never actually get there. 3. Prioritize Net New Logos At a startup, upselling inherited accounts is of little value. #1 priority must be pipeline generation and landing new accounts. When interviewing, if a candidate cannot detail every specific logo they brought in and exactly how they closed it, the interview is over. 4. Implement High-Accountability Attrition Scaling companies should model for 25% total attrition and intentionally "shoot the bottom 10%" of the sales organization every year. If you don’t hold underperformers accountable, your "A players" will eventually quit because they refuse to be surrounded by mediocrity. 5. Error on the Side of Lower Quotas If you have to choose, it is always better to set quotas slightly too low than too high. Setting impossible quotas leads to your best talent making no money and quitting, which is the most expensive mistake you can make. It is far easier to fix a "happy" sales force that is blowing out their numbers than to replace an entire team. 6. The In-Office Mandate Inside sales is an in-office business. The sales leader needs to be there five days a week, sitting with the reps to maintain intensity and immediate feedback loops. Inside sales efficiency dies in a distributed model. 7. Respect Over Popularity If a sales leader is beloved by everyone, they are likely the wrong person for the job. Winning requires conflict, and a great leader calls people on their shit to make them better. 8. AI will Replace Tasks, Not Sellers SDR and BDR roles will likely be gone within five years as AI drives massive efficiencies in early-stage prospecting. However, high-ticket enterprise sales will remain human. (Links in comments)

20VC invested in Fyxer when it was 4 people and $1M in ARR. 12 months later, it is $35M ARR and 63 people. In every category; voice, video, legal, email, European startups are crushing their US counterparts. We can build mega companies in Europe. This is our time. LFG!

The craft of your product is the respect for your customers. We do not release 30% of shows we record. Every single show, 10 years in, with large media teams, I still listen to every single one pre-release. We remove 35-45% of shows to optimise word to value ratio. Details are not details, they are the product.

Why VC Firms Must Have Their Own Agents: "VC firms should have their own autonomous agents. PE firms will have agents analyzing markets and opportunities. If I were starting from scratch, I would build incredible data systems to evaluate where AI companies should go and which markets are right. The deciding factor will be how well founders and investors use autonomous agents in their jobs." @aspenjfm Love to hear your thoughts on this @nbt @mattocko @asenkut @alexisohanian @JaredSleeper?

I have spoken to 3 founders in the last 48 hours; all of them with 500-1,000 employees. Each of them is planning a minimum 20% headcount reduction. Said with great concern; this is about to get very real for labour markets.

It took me two years to get 1M plays. Now we get 1.2M plays per day on 20VC. Most people fail because they give up. This is a game of who can survive the longest.

The minute the founder leaves a pre 1BN company, honestly, it just barely ever works. “Thrilled to announce the move to Chairman”. Ouch, run.

I am so fricking bored of guests that go on 10 podcasts and say the same frameworks again and again. Coatue manages $30BN on the private side. Their growth fund is $7BN. They have investments in Revolut, Anthropic, OpenEvidence, Canva and more. And yet, the Co-Head of Coatue, Lucas Swisher, never does podcasts. That changes today. @LucasSwisher1👇 Spotify 👉 https://open.spotify.com/episode/5QxHPwi… Youtube 👉 https://youtu.be/Hom5OMMzOQ0 Apple Podcasts 👉 https://podcasts.apple.com/us/podcast/20… Timestamps: 00:00 Intro 01:04 Why Public SaaS Is Getting Crushed in the AI Wave 07:35 Durability of Revenue in AI 15:28 Market Size vs Founder Quality: What Wins? 16:52 Why Price is the Last Thing to Matter 23:32 Mega-Funds Math: Can $5B+ Funds Still Generate Venture Returns? 27:01 What Returns Are 'Enough'? Why 3x Isn't Exciting at Growth 29:54 When Double-Downs Go Wrong: Overestimating TAM and Multi-Product Expansion 32:37 Margin Matters… But at Scale: AI Gross Margins, Cost Curves & Efficiency 37:11 Why it has never been harder to be a seed investor 40:11 Is 'Kingmaking' a Myth: When Capital Helps (and When It Hurts) 45:23 Is Canva Really a Platform Company? Multi S-Curves and Leaning into AI Early 46:52 Lessons from Mary Meeker 50:08 Lessons from Mamoon Hamid 51:34 LP 'Pick One' Games: Mamoon Hamid, Mary Meeker, Insight Partners 53:40 OpenAI vs Anthropic: Who Wins? 59:17 Most Memorable Founder Meeting 01:01:35 Career Decisions & Misses