Nick Tippmann

Big news: I’m thrilled to officially unveil @TipTopVC — a new pre-seed/seed stage, operator-led venture firm backing the next-gen of Vertical AI founders. After an amazing 8+ year run as founding head of marketing and CMO at Greenlight Guru — from $0 to tens of millions in ARR, creating the medtech QMS category, and raising $120M+ — I knew I had two paths: a) start another software company b) start a venture fund built the way I wish VC worked when I was a founder For nearly 13 years, it’s been a personal goal to build a top-tier VC firm that the best founders want to work with. But the marketer in me always said: “the world doesn’t need another undifferentiated B2B SaaS fund.” So I unplugged. Got a cabin in the Rockies with my then girlfriend, and now wife. And after some much-needed clarity, I had four big realizations: 1. I didn’t have one problem I wanted to solve for 10-15 years—but I had unique experience operating in vertical markets that founders could lean on 2. The future of software (and AI) is vertical 3. My experience gave me a unique right to win with the top founders 4. The best VC firms of the next decade would operate like AI-native startups themselves—brand-led, data-driven, community-built That’s when TipTop Ventures was born. The Vertical SaaS+ thesis I shared nearly 2 years ago unexpectedly went viral. That post pulled me forward. Fast forward to today—and after 30+ vertical SaaS+ angel deals, over a dozen LP checks written, and 9 TipTop investments closed—I’m proud to announce we’re live. While I’m just now announcing the firm, here’s what we’ve quietly built so far: - 9 investments across legacy and underserved industries - 3 companies marked up out of 6 investments made in 2024 - Raving founder feedback on our support-per-dollar invested - 30+ founding LPs from the likes of ServiceTitan, Procore, Mindbody, Greenlight Guru and more It hasn’t been easy going zero-to-one in this market—but the momentum is real. In fact, based on Carta’s latest fund data, if we were a 2023 vintage (we’re 2024), we’d already be tracking top decile. And yes, TipTop is led by a solo-GP, but not solo-built. I’d like to express my deep gratitude for all the support from these early believers: Thank you to my amazing wife Mari Tippmann for your unwavering support since day-minus-one Thank you to our LPs for your early belief and trust–it’s taken very seriously Thank you to Bill Loss for being a rock as founding advisor and LPAC member Thank you to Ershad Jamil for joining me as a Venture Partner And most of all — thank you to our founders. You chose us when we didn’t even have a website (or a fund in some cases). I’ll never forget that. We believe AI is the biggest platform shift since the internet. We believe the future of AI is vertical. And we believe the best founders aren’t just building tools — they’re reinventing industries. If you’re one of those founders: we’re writing $150k–400K checks at pre-seed/seed. Let’s build together. Join us on the journey to the TipTop.

@Magyer Had a ton of fun jamming on all things Vertical AI with you, Joe! Thanks again for having me on, and great write-up! Hopefully some good nuggets in there for founders building today.

Excited to share my conversation with @ntippmann! Nick is a vertical AI and GTM expert so it was great to talk shop with him about AI, how B2B SaaS evolved, and how distribution has changed. Here are some takeaways and insights from the conversation: Vertical AI changes the value proposition from efficiency to execution. Nick’s core framing is that SaaS helped people save time, while vertical AI can actually do the work. That shift changes the buyer, the budget, the pricing model, and the ceiling for how large these companies can become. The real TAM unlock is services and labor, not software. Traditional vertical SaaS was constrained by software budgets. Vertical AI can compete with outsourced services, internal labor, and professional work that previously sat outside the software spend category. That is why Nick sees the opportunity as dramatically larger than the prior wave of vertical SaaS. The best vertical AI companies will not be thin wrappers. Nick’s bet is on companies that combine workflow software, domain-specific context, proprietary data, and agentic execution. The model is not “AI replaces SaaS,” but “SaaS evolves into a system of work.” Incumbents are vulnerable when their strength becomes rigidity. Legacy systems of record often have distribution, data, and customer relationships, but they can also be slowed by old architecture, existing pricing models, and organizational inertia. Nick is most interested in markets where the incumbent is entrenched but not especially nimble. Distribution and trust may matter more in AI, not less. Because software is easier to build, it is harder to stand out. Nick argues that content, community, events, brand, empathy, and domain expertise remain critical. In vertical AI, credibility with the buyer can be a moat before the product moat fully compounds. Outcome-based pricing is becoming the new frontier. AI products are pushing companies away from seat-based SaaS pricing and toward pricing tied to completed work: per resolved ticket, per document, per workflow, per enriched record, or against avoided professional services spend. The best pricing models will align with the value customers actually experience. Forward-deployed services are not a weakness; they may be evidence of where value accrues. Nick sees OpenAI and Anthropic building services-heavy motions as a sign that intelligence alone does not solve enterprise problems. Context, implementation, workflow integration, and judgment still matter — which supports the vertical AI thesis. Seed investors need to look past the demo. In a world where a founder can vibe-code a polished product quickly, Nick focuses on deeper questions: Does the company get better with usage? Is there proprietary data exhaust? Are there reinforcement loops? Can the wedge expand into adjacent workflows? Is there a real vision beyond the initial tool? The wedge still matters, but the expansion timeline is compressing. Nick acknowledges that AI lets companies build more faster, but he still wants a sharp entry point. The difference is that founders may need to move from wedge to broader workflow coverage much earlier than in the SaaS era. GC AI is a case study in founder-market fit plus distribution. Nick backed the company because Cecilia Ziniti brought deep credibility in legal, had early community instincts, and chose a focused wedge in in-house legal. The insight was not just that legal work fits LLMs; it was that in-house legal has distinct workflows, budgets, and pain points from law firms. VCs and founders are often talking past each other. Nick thinks VCs underappreciate how brutally hard execution is, while founders often misunderstand fund math and why “good growth” may still not be enough for the next round. The AI era has raised expectations, especially as investors compare every company to the fastest-growing AI breakouts. Nick’s contrarian view: foundation labs moving up the stack does not kill vertical AI. His argument is that the labs’ move into applications and services actually proves the opposite: raw model intelligence is not enough. Durable value may accrue to companies that own the workflow, the customer relationship, the domain context, and the system of work. Really enjoyed this episode of @InvestNStartups. Thanks to Nick for coming on!

Co-hosted an intimate VC dinner here in Austin with @charliepinto @ @blingcapital this week. Big shoutout to @abickerstaff & his team at @DLA_Piper for sponsoring. A great mix in the room: emerging managers, longtime ATX staples, and multi-stage firms from the coasts. The energy and candor were awesome. Looking forward to doing more of these and continuing to strengthen the venture ecosystem here in Austin and beyond.

@HackItMax Well said, Max. Excited to keep partnering with you and the founders building some of the defining companies of the Distribution Era.

@Jason_A_Scharf @TipTopVC Fun conversation, @Jason_A_Scharf! Thanks for having me back on for the epilogue. Lots of updates since last year!

A year ago I sat down with @ntippmann of @TipTopVC on investing and building in vertical AI. We left one question unresolved. Where do foundational AI models end and where do the applications begin? Since that time we have seen the launch of Claude Design, OpenAI's Rosalind, and other vertical applications from the frontier labs. I am re-releasing last year's episode with a new epilogue as I invited Nick back to discuss what has changed since our first conversation. The Agenda 00:00 Defining vertical AI 05:07 Where general AI fails 09:36 Vertical AI software, not just chatbots 16:44 Pricing logic after the seat model 24:04 Underwriting at pre-seed and seed 27:20 Capital intensity and seed-strapping 36:48 TAM analysis and the Frontiers Market example 41:46 OpenAI's Instacart hire and the gray zone 45:55 Austin as a vertical AI hub 58:21 Epilogue: Where the models end and applications begin.

@lacostejonathan @hawkeye360 @NYSE @HawkEye360CEO Huge congrats!!

Congratulations to our portfolio company @hawkeye360 on their IPO at the @NYSE this morning! This represents the first IPO for our firm 👏 Trading under HAWK, we're excited to watch @HawkEye360CEO & team continue to execute moving forward

Fun chat with AdMaiora Ventures and friends

@louisbookoff Thanks Louis!

@ntippmann Well deserved @ntippmann!

Meet 50 of the world's highest-signal emerging VC firms. Nominated by investors, selected by Confluence. Most venture lists reward what’s already obvious. The Confluence 50 is interesting because it looks for emerging managers who may be obvious in five years, but are still early enough today that the market hasn’t fully caught up. I’m proud to see @TipTopVC included.

Particularly alongside so many friends and firms I respect, like @GTMfund, @SarahSmith, @weekendfund, @Joshuabrowder, @footworkvc, @euclid_vc, @yonderventures, @breakersvc, @forward_deploy, @WischoffVC, @rexsalisbury, @redbudvc, and many more. Appreciate @ClayNorris10, @confluence_vc_, and @harmonic_ai for the work behind this and the recognition. Check out the full list here (paywall): confluencevcweekly.beehiiv.com/p/50

@ItzSuds Beast. Congrats, lfg!

Yesterday, 11 months after I started, I got the final commit for fund 1 I raised 525k in 2 days. I thought I was made. 6 mo later, on Oct 1, I’d only signed 1.7m Fund returns helped, but the only change I made was to unapologetically be me. Being authentic pays, it’s just hard.

@chamath Very cool @chrisstrobl !

Nice.

@alexbass @lukesophinos @NPoulos Thanks Alex! Hopefully some good nuggets in there for ya :)

@ntippmann @lukesophinos @NPoulos Ooh, fun! Excited to check it out!

I joined @lukesophinos + @npoulos on Verticals to talk: • Why “SaaS is dead” is the wrong frame • AI-native upstarts vs incumbents • Instrumenting GTM like a product (+ 7 Vertical AI Plays) • Pricing strategies in vertical AI • Seed → Series A benchmarks right now Platform shifts expand markets - but they also reshuffle winners. Full episode 👇

Luke’s recap + Trillion Dollar Battle Scorecard: newsletter.lukesophinos.com/p/linear-1645-…

Nic’s recap + 7 Vertical AI GTM Hacks Playbook: insights.euclid.vc/p/verticals-18…

@chrisstrobl Yessir! You can feel the energy on the ground here in Austin.

Very smart analysis about diversification. Nick you are at the right time at the right place. @ntippmann

@ColinGardiner Austin VC and startup ecosystem is on a roll indeed! Excited to be building here alongside such a strong cohort of emerging managers, my friend.

Austin VC is on a roll. I won’t say the epicenter is shifting but the green shoots of something big are forming. In particular the Austin Emerging Manager cohort that's forming right now is looking very promising. Lots of killer first funds that I am sprinting to keep up with. Here is who is top of mind in town but please tag other folks: @itsdanieldart - Rockyard Ventures (also putting on Future Titans conference) @ntippmann - TipTop Ventures (AI vSaaS with early investment in GC AI) @Magyer - Seaplane Ventures (network effect bizs with early investment in Micro1) @krdonnelly - Avalanche VC (early investments in Bluesky and Starbridge) @vsodera - Supercharge VC (killer investment rap sheet) @annieluchsinger - Breakers (heard great things from @Cashflow_Cowboy) @jaydimonte - Grid Capital (honorable mention since not here full time; supply chain all day and great track record at previous firm) The best part is I count many of them as friends. Let me know who I missed.