Dan Hockenmaier

You can have customers saying nice things and still not have product market fit. Andy Greenfield, partner at TIA Ventures, spent decades doing qualitative research for major CPG brands. He pioneered a methodology to separate polite responses from visceral pain. Getting different audiences together in panels to understand if products were solving real problems. When they'd do these panels, they'd try to get to one specific question: "If this product were taken away tomorrow, would your life be okay or couldn't you live without it?" That's a very different question than "do you like this product?" Jesse Caesar from First Round Capital explains the difference: "If you want to know what your target is doing or how much, go for quantitative research. But if you want to know why they're doing it, or why they believe what they believe, qualitative research gets you that depth of perspective." Most founders confuse customers being polite with customers who actually care. It’s much easier to do that vs facing hard truths sometimes. You ask someone about your product and they'll say "Yeah, this is super useful." But when you dig deeper with the right questions, you realize they don't actually care that much. I can’t overstate the value of qualitative user research whether investing or building a product myself. Talking to 10 customers with very specific questions to gauge how important the problem really is.  It’s also very helpful to cross reference this with quantitative metrics with tools like PostHog or Mixpanel. “Trust but verify”. The real magic is when you do both of these things in concert. For example, a client you interview may say “I really love using your feature that lets me do XYZ” and they may be very specific about the value it delivers…so it may seem like a totally credible piece of feedback, but then when you look in PostHog or any user analytics platform, you see that they’ve only used the feature once. So this begs the question “if you find feature XYZ so valuable, why have you only used it once in the past month?”  This gap is often the difference between a company that scales and one that plateaus.

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Let’s Celebrate Customers, Not Just Capital! Every week, my feed is filled with founders celebrating fundraising milestones. “We’ve raised $5M pre-Series A.” “We closed a $10M round led by X, joined by Y.” 👏 The community applauds. VCs repost. Other founders cheer. But raising capital is not the finish line — it’s just the starting gun. And sometimes, a large round can actually make the race harder. Why? Because big rounds bring big expectations: - Unrealistic growth targets imposed by investors. - Premature scaling before product–market fit is proven. - Pressure to spend rather than build sustainably. - Distraction from users — the story shifts from solving problems to “managing burn and runway.” The truth is, many investors see through the cracks. They read pitches and quickly recognize when a founder’s focus is skewed toward fundraising headlines instead of customer validation and execution. For those investors, the red flags are obvious. 👉 And this is where experience matters. Over the past decade, I’ve sat on both sides of the table — building investor networks while working directly with founders on strategy, fundraising, and growth. Through close work with leading private equity investors, I’ve gained a clear understanding of why they often prefer to enter at the pre-IPO stage: it offers proven growth, clearer visibility on returns, and management teams tested under pressure — all with a defined liquidity path. That combination of investor rigor and founder empathy is what I bring to any role. I’ve seen founders raise aggressively, only to find themselves under crushing pressure to deliver unrealistic metrics. Others stay disciplined, put users first, and build companies that endure — which in turn attract the right capital at the right time. What should we celebrate instead? - The first 100 loyal, paying customers. - Expansion into a new market with real traction. - Retention rates that prove customers love the product. - Products that solve problems so well they become indispensable. This is why my work today focuses on helping founders align fundraising with customer validation and sustainable growth. With a network spanning founders, operators, and investors, I see both sides: where capital amplifies success, and where it becomes a burden. So here’s my invitation; let’s shift the narrative. Don’t just clap for capital. Clap for customers. Because in the end, what mattered most wasn’t the seed round — it was the trust and loyalty of our users, which became the true driver of growth and scale. That’s why I pause when I see awards handed out to founders while no customers are in sight. The only prize that really matters is earned from the people who choose to use your product. #VentureCapital #PrivateEquity #Startups #Leadership #CustomerExperience

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BONUS EPISODE; After 20+ years building companies, one thing is clear: Speed, talent density, and repeatability beat the single-founder grind every time. That’s why the venture studio model is rising. It gives entrepreneurs the ability to launch multiple companies with shared resources, shared intelligence, and shared momentum. This is where the best operators are heading—and it’s the direction the future is already moving.

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PSA to seed and early-stage founders: stop worrying about competition. I’ve spoken to hundreds of late-stage founders, and they all say the same thing. The biggest mistake they see at the early stage is founders obsessing over who else is in their space. When you are pre-PMF, comparing yourself to other buzzy AI startups is a distraction. They already have a defined GTM motion, some level of product-market fit, and a playbook to execute. Their “big new feature” might just be about expanding revenue or building parity. You’re still trying to land your first 10 paying customers. Here’s the truth: 1. Worry about competitors only when you actively lose a deal to them. THESE ARE THE COMPETITORS TO WORRY ABOUT. 2. When a customer chooses someone else, they will usually tell you why. Nine times out of ten it’s not the reason you think. It’s rarely a missing feature. More often it’s pricing, brand trust, or timing. 3. Competitors often move in completely different directions. OpenAI went after consumers, while Anthropic leaned into enterprise and APIs. Playbooks diverge fast. 4. The only real roadmap at the early stage is customer pain. Every conversation, every demo, every user insight. Talk to as many customers as possible. If you spend your time trying to copy what competitors are doing, you will always be a step behind. If you spend your time talking to users, you’ll know exactly what to build next. The path to PMF isn’t found on Twitter threads about “AI competitors.” It’s found in the feedback from the 5 people actually using your product every single day.

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Lately I’ve been spending time thinking about how to structure early partnerships specifically to earn Letters of Intent (LOIs).. not as optics, but as a way to genuinely de-risk pre-seed capital raises. A few learnings that may help other first-time founders: 1️⃣ An LOI isn’t about revenue — it’s about judgment At pre-seed, investors aren’t underwriting certainty. They’re underwriting how you think. A clean, non-binding LOI signals credibility without over-promising. 2️⃣ The best partners aren’t “channels” — they’re collaborators If the relationship feels extractive early, it won’t last. The strongest partnerships are built on shared incentives, shared learning, and clear boundaries. 3️⃣ Optionality beats speed Locking things in too early often creates more problems than progress. Time-bound, capped structures keep everyone aligned while value is still being proven. 4️⃣ Good LOIs protect everyone - Non-exclusive. - Non-binding. - Plain English. - Focused on intent, not outcomes. 5️⃣ As a solo founder, relationships are leverage When you don’t have scale yet, your ability to listen, structure fairly, and think long-term becomes the signal investors actually pay attention to. Building Wind Caddie has reinforced this for me: strong early partnerships aren’t about closing deals, they’re about proving alignment before scale. If you’re an angel who values disciplined early structuring, or a founder navigating pre-seed, I'm always open to thoughtful conversations and comparisons of notes 😀 #StartupFounder #FirstTimeFounder #PreSeed #AngelInvesting #EarlyStageStartups #BuildingInPublic #Partnerships #Fundraising #SaaS #SportsTech

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Outlier founders understand that uncertainty is a permanent condition of the world. They design systems that work across many futures. They build teams that can reconfigure, cultures that embrace experiments, and products that can bend without breaking. Optionality is how they stay on the path, even when the path changes or disappears entirely. Our obsession with efficiency need not kill optionality, but it does require slack, which is the margin where discovery happens. Time to think. Capital held in reserve. Space for curiosity. They are not a waste of resources. They make resilience possible. Founders who survive crises are not necessarily more intelligent or more efficient. They ensure their companies are not overextended. In a complex world, perfection is brittle. Resilience depends on our ability to stretch, absorb stress, and recover. - Alfred Lin at Sequoia Capital (link in comments)

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The SMS interactions between brand & consumer contain incredibly rich context for 1:1 personalized commerce experiences. Postscript is the platform enabling such experiences. On this week's episode, Rishabh and I sat down with Adam Turner to explore how SMS evolved from an abandoned-cart afterthought to a 1:1 sales & marketing channel. We covered: - Category creation and the rise of the “SMS marketer” - Compliance and quality as product design principles - Moving from broadcast to conversational journeys - Building distribution in the Shopify ecosystem, then scaling a sales-led motion - Where AI has augmented vs reinvented both marketing products and teams Link in comments

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