Jesse Spevack

2025 has been my favorite year so far at The Council. This clip from our special hosts-only holiday episode of First Builders covers common themes we're seeing across our portfolio in companies that are winning vs those that are struggling to find their fit. We also get into detail about the trends we saw in the 3 main investment areas we look at for vertical AI: industrial tech, healthcare, and critical functions. Enjoy and hope you'll check out the full episode with some silly tech pop culture moments we loved from 2025 and more 🥳 Shoutout to all the First Builders guests that made this year so special: Cecilia Ziniti Danish Nagda Daniel Perez Jason Prestinario David Hoang Rohini Pandhi Nathan Baschez Maia Bittner Koby Conrad 🌻 Lisa Popovici Web Sun Eliana Berger Lauren Makler Cameron Carter Jack Greco Alessandro Chesser Zacharie Esmili Prashanthi Raman Haroon Choudery and to my partner at The Council Rachel Tsui! Best co-host ever.

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Two years ago, Sohil was building an agent framework and many of the primitives commonplace today (LLM router, tools, etc.) before they even existed. Biased but I would recommend this talk.

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Edtech is full of products that are good enough... to sell. That's the game most teams play. You win by scaling sales. Not product. Why? Selling to districts is a maze. Committees. Massive red tape. RFPs written for yesterday's tools. So teams build for procurement, not for students. They optimize the checklist and the demo. And it works. For yesterday's ecosystem. But there's a new market. Alternative education. Virtual schools. Microschools. Private and charter networks. They behave more like companies than bureaucracies. Fewer stakeholders. Faster decisions. Clear owners. They ask "Does this work next week for our kids?" and "Does this improve engagement and outcomes?" This market structure flips the equation. You can focus on building great products that people love. You can ship weekly, test live, and stack real outcomes. You can go deep on synchronous, secure, engaging experiences that actually move the needle on connection and retention. You get leverage from the product itself, not just the pitch. All-star product and engineering teams of tomorrow's EdTech winners matter more than all-star sales teams. I get the prevailing wisdom. Hire more reps. Hit the circuit. Do the dance. It can work. It just creates a culture where the deck gets better faster than the product. What if you pick markets that reward shipping over selling? That remove the red tape. Where the roadmap is shaped by real usage and not by a procurement spreadsheet. Product-first companies will win the next wave. Not by louder selling. By better building.

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Best articulation I’ve heard of why early stage startups need to be in person: “foxhole dynamics are extremely hard to remotely replicate”. If there is a better phrase than “foxhole dynamics” to capture the tension and stress and energy in a very young company, I’ve yet to encounter it.

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Six months into launching a bootstrapped edtech company - here are six behind-the-scenes screenshots. 1) MRR growth benchmark. I often feel like I’m underperforming. Seeing splashy launch videos and massive funding announcements makes it easy to feel behind. I still question whether leaving my salaried job last year was a mistake. I remind myself that a bootstrapped company isn’t playing the same game as a VC-backed startup. Some days that helps. Some days I’m just human. Looking at where we actually land against other businesses - 86th percentile on Stripe this month - pulls me back to center. Even though this feels hard, I must be doing some things right. Don’t give up. 2) Teacher feedback (the grounding force). This is what keeps me steady: seeing it used in real classrooms. Highlight: a teacher in a district pilot didn’t have to pay this year - her access was covered. After using our report card tool, she Venmo’d us $10 because of how much mental energy it saved her. Unsolicited! That felt good. In past roles, I was steps removed from the person paying the invoice. Now I ask directly why someone cancels. "Customer obsessed" is a familiar company value. It hits different living it. When I see teachers sharing accounts (even though it’s against our terms), I look the other way - and will use that signal to inform expansion talks. 3) First official Data Privacy Agreement signed. This wasn’t a priority yet - I know how slow district sales cycles are. But a teacher couldn’t access us because their district IT blocked the app. Instead of moving on, we pushed through the paperwork. Now they’re back online. More importantly, doors are opening for other CA districts and beyond. 4) Google search performance. Momentum? Our growth strategy has been mostly organic - website content, socials, word of mouth. Now I’m applying those lessons through Google and Meta ads. Every dollar spent is revenue being reinvested. It’s exciting - and a little terrifying - to watch. I’ve read about these inflection points, where founders quit just before things start to compound. I’m hoping we’re pushing into one. 5) Homegrown research tool for marketing/sales. Six months ago, I didn’t know how to run an ad campaign. Now I have internal tools to scrape public data, analyze positioning, find the right keywords, identify leads, etc. You learn fast when there’s no one else to do it. 6) Sleep and other costs. I’ve read it everywhere: sleep matters. I know it’s foundational. I still haven’t figured out how to make it work in practice. The tradeoffs show up in real ways: more grumpy mornings getting the kids to school than I’m proud of. Stress-induced flare-ups that never quite go away. Fewer friend catch-ups. Fewer calls to my parents. Skipped zoo visits, beach days, pumpkin patches. Still, it feels worth it. For now, I choose to keep going. And I don’t say it enough, but I owe everything to my support system. Six months down. Still here. A lot more ahead.

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