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In this episode of Verticals, Luke Sophinos and Nic Poulos sit down with Scott Wolf, founder and former CEO of Levelset, to unpack what it really takes to build and exit a vertical SaaS company, including Levelset’s ~$500M acquisition by Procore. Scott’s background is unusually eclectic: entrepreneurial roots, early software tinkering, a short stint as a lawyer, and a front-row seat to the construction ecosystem post-Hurricane Katrina , all of which collided into the insight that became Levelset. He scaled the business from a side project doing ~$200k in revenue to tens of millions in ARR, then navigated a fast, high-stakes M&A process that closed at the height of the 2021 market. This conversation cuts through M&A mythology and focuses on operator reality: how acquirers think, how founders should think about timing and leverage, why the best companies are bought not sold, and what founders get wrong when they fixate on the same buyer segment (general contractors) in construction tech. Whether you’re pre-product, scaling a vertical SaaS business, or simply trying to understand how real outcomes happen in construction tech, this episode offers a practical, founder-first playbook grounded in lived experience, not theory. We cover: The origin story: why liens and construction payment disputes created a massive software wedge How Levelset went from transactional to SaaS, and what changed the growth curve Why selling to suppliers and subs (not GCs) created differentiation and enterprise scale contracts Construction tech “dead ends” and where Scott sees opportunity beyond the GC workflow How Procore first approached the category (and why they couldn’t build it in-house) What it looks like when an acquirer is “in heat”, speed, leverage, and market-making The founder decision: duty to stakeholders, timing the cycle, and why exits happen when they do Scott’s advice to founders: excellence first, M&A second If you’re a founder, operator, or investor building or backing vertical SaaS, especially in construction or the built world, this is a must-listen guide to how great companies get built, differentiated, and ultimately acquired. New episodes drop every Wednesday. 00:00 – Intro Luke & Nic introduce the episode and guest Scott Wolfe 01:30 – Scott Wolfe’s background From law and software tinkering to construction tech 05:20 – The origin of Levelset How Hurricane Katrina exposed a massive payment problem in construction 10:45 – Early traction & bootstrapping Building to $2M ARR with a $500k angel round 15:40 – Finding product-market fit Moving from transactional workflows to SaaS 20:30 – Construction tech in the 2010s Procore, PlanGrid, BuildingConnected & the ecosystem taking shape 25:10 – Why Levelset went bottom-up Subcontractors, suppliers, and avoiding the GC obsession 30:20 – Construction finance as a massive opportunity Liens, payments, and why this category was inevitable 35:10 – The problem with chasing general contractors Why most construction startups hit a ceiling 40:00 – Today’s construction tech landscape Permits, suppliers, professionals, and under-served segments 46:30 – Vertical AI & recent funding rounds Thoughts on Trunk Tools, PermitFlow, and capital discipline 52:45 – First conversations with Procore Early partnerships vs long-term acquisition interest 57:30 – The acquisition process How Procore came back post-IPO and moved fast 1:02:40 – Negotiation & deal dynamics Why the process was surprisingly low-stress 1:04:30 – Closing thoughts Luck, timing, and why exits are never guaranteed