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I'm the CEO/Co-Founder of Late Checkout, a holding company with a portfolio of internet businesses. Previously, I was the Head of Product Strategy at WeWork, an Advisor at TikTok and an Advisor at Reddit. I was the Founder/CEO of Islands, a messaging/community app that was acquired by WeWork. I was the Founder/CEO of 5by, a leading video discovery app which got acquired by StumbleUpon. I helped build one of the internet's most popular financial education communities Wall Street Survivor (acquired). I've helped build communities and technology products for brands like Microsoft, FedEX, NASCAR, TechCrunch and Wordpress. I've been featured on places like Vanity Fair, Forbes, Mashable, Fortune Magazine, L.A Times and have won Webby Awards. I share my thoughts on Twitter @gregisenberg (say hello). LINKS to some of my companies in my holdco🔗 gregisenberg.com (my guides, podcast, sign up to my weekly newsletter for updates) latecheckout.agency (product design agency that works with executives from Dropbox to Nike to Shopify) boringmarketing.com (agency to get you ranked on google) boringads.com (agency that creates profitable ad campaigns)
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We’ll look back at this era like the gold rush. Except this time: – picks + shovels = prompts + AI agents – gold = attention, data, distribution – miners = builders automating boring work – gold pans = n8n, replit, bolt, lovable – land grabs = ai-first domains + keywords – mining towns = niche discords + communities – saloons = X, short form video – mentors = youtube + pods – railroads = zapier, lindy, chatgpt + open source workflows – hardware stores = marketplaces for agents + templates – prospecting = searching reddit, docs, search consoles – speculators = people flipping AI tools – outlaws = folks scraping sites and charging – sheriffs = devs enforcing rate limits + terms you don’t need funding. you need a browser, a niche and a a good idea. start digging.
how to prompt like a pro 1. share your raw idea 2. ask: “what’s unclear, risky, or missing?” 3. then: “push this idea to its extreme” 4. then: “make this resonate with [my audience/customer/community]” 5. finally: “what would a 0.01% top operator do next?” for more ideas like this, subscribe to gregisenberg.com
the new startup playbook looks NOTHING like the old one: – most of your team will be part-time contractors, creators, and ai agents – your first $1m will come from niching down. your next $10m will come from tastefully scaling out – one agent spins out 50 longtail SEO pages from transcripts, support tickets, or user reviews – startups are turning into QVC. except this time, you own the channel and the product – onboarding will feel like texting a friend. static forms are dead – every landing page rewrites itself based on who's viewing it (claude or chatgpt-4o + session data) – every successful company will feel like a subculture. the product is just a portal in – outbound are agents scraping, qualifying, and writing personalized intros 24/7 – customer support = 1 human backed by 5 lindy agents trained on every support ticket ever written – micro-apps will outperform mega-tools. specific > general – growth isn’t an afterthought. it’s built into the product (agent-invite loops, ai-powered referrals) – if your product doesn't spark curiosity in 2 seconds, it’s invisible – the best products of the next decade will be memes first, software second – “launch” is outdated. leak it instead – the new pricing model: $0 to play, $x to unlock identity – you won’t sell software. you’ll sell outcomes, transformations, identity upgrades – more people will leave big tech to build solo. not out of rebellion, but because their side hustles are more interesting – the best homepages become a scene. your standard shadcn websites won’t hit the same – default alive is low burn, small team, owned audience, high-leverage systems – competitor research happens automatically. agents scrape, cluster, and surface positioning gaps – your CRM isn’t stale. agents log calls, summarize deals, and write follow-ups before you hang up – venture capital is optional – customer success isn’t reactive. agents predict churn based on tone in support chats and usage – we’ll see more “tiny empires”: one founder, one audience, and a constellation of tools they own – bug reports are summarized, tagged, prioritized, and triaged by an agent before eng ever sees them – IRL matters. founders become event planners – most SaaS is overbuilt. the next wave wins by subtracting – if your product can't be explained in a screenshot, it won't spread – the creative director is the new power hire. taste is now a growth lever – knowledge base builds itself from slack threads, loom links, and discord q&a (agents + gpt vision) – product feedback loops are instant. users speak → agents summarize, prioritize, and mock ui changes – startup advice used to be: find a technical cofounder. now it’s: find a distribution edge – your product isn’t finished when it works. it’s finished when people want to wear the hoodie – the people who win distribution will own demand. the rest will rent it for more ideas, subscribe to gregisenberg.com
OpenAI published their official GPT-4.1 prompting guide, and I summarized it into these 13 practical tips to help you get the most out of the new model. GPT 4.1 Prompting Guide Notes 1/ Follow instructions literally. GPT-4.1 is trained to follow directions more precisely than previous models. Be explicit about what you want. 2/ Place instructions strategically. For long context, put critical instructions at both the beginning AND end of your prompt for best results. 3/ Use specific delimiters. Markdown headings, XML tags, and backticks help the model understand structure. JSON performs poorly for document collections. 4/ Induce planning with prompting. Ask the model to "think step by step" when solving complex problems to significantly improve accuracy. 5/ Design agentic workflows with clear reminders: "Keep going until the problem is completely resolved" "Use tools when uncertain instead of guessing" "Plan extensively before each action" 6/ Leverage the 1M token context window wisely. Performance stays strong up to the limit, but degrades when retrieving many items or reasoning across the entire context. 7/ Balance internal vs. external knowledge. For factual queries, instruct the model to "only use provided context" or "combine context with basic knowledge" based on your needs. 8/Format your prompts with clear sections: Role and Objective Instructions (with subcategories) Reasoning Steps Output Format Examples Final instructions 9/Guide information retrieval. When working with documents, ask the model to first analyze which ones are relevant before attempting to answer. 10/ Avoid rare prompt patterns. The model may struggle with extremely repetitive outputs or parallel tool calls. Test these cases carefully. 11/ Be direct with corrections. If model behavior is unexpected, a single clear sentence is usually enough to steer it in the right direction. 12/ Use specific frameworks for coding. For generating code changes, use the V4A diff format with context lines for maximum accuracy. 13/ Remember it's not a reasoning model. GPT-4.1 doesn't automatically provide an internal chain of thought, but you can explicitly request it to show its work. For more notes, ideas on the future, subscribe to gregisenberg.com
Email from Fiverr CEO to his team about AI ($1b company): For more interesting ideas like this, subscribe to gregisenberg.com
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