Seguin Ventures

🤝 For my new friends, Seguin Ventures invests $200K-$400K into seed stage software companies building B2B AI-Native applications. We equip founders, building within or beyond 🌉 Silicon Valley & 🗽 New York, with uncommon unicorn networks and expertise to scale to $100M in revenue. 💪 My partner Steve Johnson and I helped Hootsuite scale to its first $100M of ARR very quickly soon after social became the new, untapped platform, and companies needed a solution to manage their presence and relationships there. 🎯 We prefer backing product-obsessed and technical founders. We advise them on scaling GTM, Operations and Partnerships, and do this especially well when selling to a complex buyer (think 🏦 Financial Services, 🏭 Industrials, the Finance function, etc.). 🌎 If you're building a global company, chances are Seguin Ventures can be complementary to your coastal networks, and can help you find your next customer, hire or partner in a less common tech and talent hub. 📍 Steve lives just outside of Boston, and has worked across Canada and the U.S. his entire career while living there. I live in Toronto, have strong west coast roots, and supported ~50/50 US/Canadian companies as a director or investor. ✉️ Reach out if this is interesting!

Advice on building SaaS companies have been playbooked to death— one guide on reaching $0 to $1M ARR, another on scaling your engineering team, yet another on managing CAC/LTV, and countless more on sales efficiency. But in the AI-Native world, there is no playbook. Case in point: DeepSeek, which shocked the industry a few weeks ago, is Exhibit A of something that seemingly came out of left field and recalibrated the economics of being an AI company. The value of the playbooks published online during the SaaS era have depreciated significantly. Instead of playbooks, or manuals, I think the guide to building AI-Native companies follows more of a mystery novel. Mystery novels follow a distinct structure that might be instructive for navigating the AI-Native landscape: - The Setup: Introduction of the core mystery and initial conditions (”Attention is All You Need” paper - 2017, ChatGPT research preview - 2023) Red Herrings: False leads and apparent solutions that turn out to be incomplete (2024 - LLM Wrapper companies) - Plot Twists: Unexpected developments that force re-evaluation of previous assumptions (Early 2025 - DeepSeek-R1) - Investigation: Systematic exploration and gathering of evidence (Present Day) The Reveal: Understanding emerges gradually rather than following a predetermined path (Future) Like a mystery novel, success in the AI-Native world requires careful observation, expertise and the ability for that expertise to adapt as new information emerges. There is no linear path to follow. Adaptive expertise is crucial in the early chapters of this AI-Native super-cycle. So instead of co-founding Seguin Ventures with someone similar to me in work and life experience, I brought on my long-time former colleague and friend Steve Johnson as my co-founder and GP.