Bryan Hunsinger

Harpoon Ventures + Black Flag is teaming up with Microsoft for Startups to provide founders with access to up to $250,000 in Azure credits, empowering builders to scale faster, train models more efficiently, and access world-class AI infrastructure. What’s included: ⚡ Up to $250K in Azure credits (usable across Azure OpenAI, Grok 3, Llama 4, and more) 💻 On-demand GPU VMs for model training and fine-tuning 🧠 Access to GitHub Enterprise + Microsoft 365 Business Premium 🤝 Dedicated Microsoft technical + GTM support This partnership is designed to give deep-tech and dual-use founders the tools and resources they need to win. Because when they win, we all win. 🏴‍☠️

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Since posting our guide on how to price AI software, I've been inundated with founders looking to talk through pricing strategies for their startups. Unfortunately, most are skipping the critical first step.   They are spending lots of cycles iterating on "how" to charge (e.g., usage-based, outcome-based, hybrid, etc).   But they're neglecting the most foundational element: how much to charge. We're finding that with proper ROI frameworks, AI products are able to capture 25-50% of created value, which is significantly higher than traditional SaaS's 10-20%.   Here's how the best founders are achieving these pricing levels:   1️⃣ They bring pricing discussions into the sales conversation early   The worst thing is waiting until procurement to talk about pricing. The role of enterprise procurement departments is to minimize spend, not to assess value. They lack budget categories for 'AI that does the work of 3 people'—so they'll try to squeeze you into their existing software line items.   When prospects seem hesitant to discuss ROI upfront, don't push. Instead, propose a value audit session. Sit down with them after they've used your product for a few months and calculate ROI together based on real usage data.   I've seen founders use this brilliantly during negotiations: "I'll give you a discount, but in six months we need to do a value audit." It's a fair trade that shifts the conversation to outcomes.   Here's a bonus move: always offer outcome-based pricing even if customers don't choose it. Simply presenting it signals confidence and willingness to share risk. When positioned alongside a fixed fee, it makes the fixed fee look fair by comparison.   2️⃣ They calculate ROI holistically, not just hard savings   Most founders focus only on labor reduction or vendor spend cuts. But that leaves money on the table.   Factor in the opportunity cost of time efficiencies. Include potential implementation cost differences compared to traditional SaaS. In many cases, AI products deploy faster and cheaper, which should be reflected in your ROI calculations.   Work with buyers to agree on ROI inputs upfront. Once they've signed off on the framework, challenging the outputs becomes much harder.   3️⃣ They use the "acceptable, expensive, prohibitively expensive" technique   Rahul Vohra used this exact approach from Madhavan Ramanujam’s "Monetizing Innovation" to price Superhuman:   To gauge willingness to pay, ask three questions: 1. "What would be an acceptable price?" 2. "What would be an expensive price?" 3. "What would be a prohibitively expensive price?"   Willingness to pay typically lands near the "expensive" point.   --   I've watched too many brilliant AI founders build incredible products only to leave millions on the table by treating pricing level like an afterthought.   Don't be one of them.   P.S. The complete pricing guide (with the decision framework and tactical playbooks) is live on our website. Link is in comments.

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Lately I’m hearing more founders being told to delay revenue to make early growth metrics look better for fundraising. I get the logic, but it just feels wrong. Early revenue is an important learning loop. Don’t stunt your business just to package it for VCs

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Traditional brands are doing something better than crypto brands and it’s embarrassing. They actually engage with their audience. Crypto founders are missing the mark. I recently spoke with a startup founder in the space about responding to comments under their posts, and he boldly said: "If big brands don’t reply to comments, why should we?" That mindset is exactly why crypto brands struggle with community trust. ✅ Traditional brands respond, build relationships, and foster loyalty. ❌ Crypto brands post, get engagement, and then disappear—leaving questions unanswered and giving competitors an easy win. For an industry that claims to be “community-driven,” why do so many projects fail at basic engagement? A simple reply builds trust. A conversation can turn a skeptic into a believer. But many crypto projects keep missing the opportunity. Decentralization shouldn’t mean disconnection. If crypto brands want real adoption, they need to stop acting exclusive and start engaging. What do you think—will crypto brands fix this, or is it already too late? 👇

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I recently chatted w/Clay Norris about building VC funds. We talked about everything from misconceptions about starting a fund to being transparent with founders. My fave part was our exchange on the underappreciated role of luck. You can read the interview at: https://lnkd.in/edWfktGG

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I always hear founders at pre seed say 'we did this without any marketing'. That's really impressive. Truly...it is. But also...why? I understand that you aren't going to hire a head of growth yet. Or buy ads. That's good. Don't do these things. But even at early stage there is a punch list of things you should 1000% be doing. Here it is: - have a coherent positioning document. make sure that you are saying things clearly, coherently and consistently. Yeah, it will change. Update it. - have a GREAT, well designed 5-10 page website. It costs like $1000, and makes you look bigger / stronger than you are. Strong signal to customers, future employees (and VCs) - a whitepaper that explains clearly what your customer problem is, your unique approach, and why you should exist. IN CUSTOMER VOICE (please). - active social channels, most importantly, YOUR OWN. I get it, I don't really want to be doing this either. In the words of a wise friend 'the best time to do content marketing was ten years ago. the second best time is today.' In the age of Ai there is no excuse for not having the above. 'No marketing' isn't the flex you think it is.

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Founders, your Ideal Investor Profile (IIP) is as important as your Ideal Customer Profile (ICP). While many founders are using ICP frameworks to find product market fit, I find almost no startups are using a similar framework for fundraising. Which investors are most likely to: - Convert? - Send $ on the timeline you need it? - Be a good long-term partner? I see early stage startups meeting with VCs who either do not have a mandate to invest in their geography or else are unlikely to convert soon (most common). I see founders meeting with investors who do not invest in their industry. If you are fundraising you are selling. Your product is your equity and your customer is the investor. Treat the process almost the same as you would when selling your startup's product/service. Design your IIP, go to market, get feedback, iterate, repeat.

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Every single time I talk to a YC founder, they say the same thing… The best part about YC was The 1:1:s. It’s also why YC still works in the age of infinite content. Lots of ink spilled on YC's network, funding, and brand. But the real moat is the unscalable stuff. From the outside it can look like YC is getting too big, too many startups, too many batches etc. But YC doesn't scale perfectly - it scales just enough to make these unscalable moments possible for 100 companies at a time. In a world where every startup framework is documented online, every growth hack is tweeted, and every investor deck template is available for free, what's scarce isn't information. It's personalized feedback from someone who's seen your exact mistake 50 times before. Everyone tries to replicate YC's "systems" - the batch model, Demo Day, the network. They miss that the value is in the moments that don't scale. The unscalable layer is what separates YC from every online course, accelerator clone, or founder community. It's why founders still move to San Francisco for 12 weeks instead of just watching the videos.

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