The Twenty Minute VCTooey Courtemanche: From Construction Worker to Billionaire CEO | E1090
CHAPTERS
- 0:00 – 0:31
Procore’s “too early” bet: patience, jobsite internet, and why timing matters
Tooey opens by reflecting on how Procore launched before construction sites had internet or mobile devices, making adoption painfully slow. He explains why market entry strategy and patience are decisive when multiple external shifts must occur for a product to work.
- •Construction sites in 2002 lacked internet/mobile, making SaaS usage hard
- •Procore was built ahead of ecosystem readiness (iPhone/iPad came later)
- •Market entry sequencing matters; nothing happens overnight
- •Founder conviction: digitization was inevitable, but required patience
- 0:31 – 3:04
Relocating to Santa Barbara and the origin story: building a house → building Procore
Tooey recounts how his wife Hilary’s ultimatum to move to Santa Barbara forced a reset from Silicon Valley life. Frustrations during their home build became the catalyst: stop complaining and solve the construction coordination problem with software.
- •Hilary initiates the move due to family strain from Tooey’s travel
- •Homebuilding pain points reveal a software opportunity
- •Procore starts in the guest room; early boundary issues drive renting an office
- •Credit, partnership, and “space” as practical lessons for founders
- 3:04 – 4:57
Surviving the Great Financial Crisis: near-bust, no salaries, and a fast pivot
The GFC wiped out Procore’s early customer base of custom home builders, pushing the company to pivot into commercial construction. Tooey describes selling personal assets, skipping paychecks, and relying on spouse and investor support to endure.
- •Custom home construction collapses; customers go out of business
- •Two-year pivot to commercial construction to stay alive
- •Founders stop paying themselves; sell assets and borrow to make payroll
- •Spousal belief and a committed investor become existential lifelines
- 4:57 – 6:37
Handling extreme founder stress and knowing when to quit vs. persist
Tooey explains the mindset required when everything is on the line: deep mission belief can crowd out doubt. He contrasts persistence with the instinct that tells founders when something truly won’t work, noting Procore’s unusually long pre-VC journey.
- •Mission devotion reduces second-guessing during crisis
- •Advice on quitting: founders often ‘know’ when it won’t work
- •Procore took ~15 years before institutional funding, normalizing long slogs
- •Founder identity: ‘dog on a bone’ persistence and vision ownership
- 6:37 – 9:58
Running from stigma, running toward vision: passion as the fuel
Tooey connects his drive to a history of academic struggle and low expectations, which he reframes through likely dyslexia and self-directed learning. Passion becomes the differentiator—without loving the work, he says he couldn’t have endured the dark years.
- •Background: poor student, college dropout, carpenter by trade
- •Motivation: prove others (and self) wrong about his potential
- •Autodidact pattern: excels only when deeply interested
- •Founders need more than interest—love sustains multi-year adversity
- 9:58 – 11:39
Why growth was slow for a decade: installing Wi‑Fi to sell $95/month SaaS
Harry presses on why Procore didn’t grow quickly in its first ten years, and Tooey points to basic infrastructure gaps. He shares the scrappy tactics—literally traveling to job sites to install routers—while waiting for the industry to catch up.
- •Core blocker: no internet at job sites; no mobile computing in the field
- •Founders personally install routers/access points to enable usage
- •Market timing risk: adoption lag even after technology exists
- •Conviction that construction was the last major industry to digitize
- 11:39 – 15:22
Investor timing risk and the ‘too many things must go right’ framework
Tooey lays out an investor lens: the more prerequisites for success, the higher the risk ratio—yet also the higher the potential reward. He compares Procore’s dependency chain to Qualcomm’s multi-step technological and ecosystem requirements.
- •Assess investments by counting external dependencies for success
- •Procore needed digitization readiness, jobsite internet, mobile, and behavior change
- •High-risk setups can produce outsized outcomes if they resolve
- •Qualcomm/CDMA story illustrates ecosystem-level prerequisite stacking
- 15:22 – 19:02
2015 inflection: ‘stopped checking the mailbox’ and deciding to raise institutional capital
A vivid turning point arrives when Tooey’s cofounder stops anxiously checking the mail for customer checks to make payroll. With the market finally adopting the product, they decide to ‘step on the accelerator’ and raise a meaningful round.
- •Signal of stability: enough cash and recurring revenue to stop daily check anxiety
- •Market changed more than product did; adoption finally arrived
- •Survival tactics pre-inflection: custom development work to generate revenue
- •Core founder advice: revenue is oxygen—do what keeps you alive
- 19:02 – 24:47
Fundraising lessons: from 2008 rejection to choosing value-aligned partners
Tooey contrasts a humiliating 2008 Sand Hill experience (dismissed as ‘idiots’ and told to be ‘more like Facebook’) with later success when the narrative flipped. He emphasizes partner quality over firm brand and warns about emotional manipulation during raises.
- •2008: dismissed by a major firm; misfit between product and market readiness
- •2015+: same market conditions make founders look ‘genius’ without changing much
- •Key learning: partner fit and shared values matter more than firm name
- •Tactics/lessons: run a clean process; consider structured approaches (e.g., closed-envelope)
- 24:47 – 26:56
The skateboard metaphor for hyperscaling: speed wobbles, naivety, and focus
After raising capital, growth accelerates rapidly—doubling repeatedly—creating a sensation of barely keeping up. Tooey explains how a certain naivety and singular customer focus helped them survive scaling chaos and recognize milestones late.
- •Post-raise growth: repeated doubling; momentum builds by 2017
- •Skateboard ‘speed wobbles’ metaphor: running to avoid crashing
- •Billion-dollar valuation moment arrives almost unexpectedly
- •Belief that some naivety/ignorance can protect focus and execution
- 26:56 – 30:53
Scaling the product line without losing focus: enterprise-grade rebuilds and globalizable needs
Procore expands beyond its flagship project management tool as customers demand a platform instead of point solutions. Tooey details painful tradeoffs, including pausing a financial product for a year to re-architect for enterprise scale, and learning from region-specific demands like ANZ safety laws.
- •Pre-2017: one flagship product; post-2017: deliberate multi-product platform expansion
- •Force-ranking customer needs to prioritize new modules (finance, quality, safety)
- •2019 lesson: pause features to re-architect financial product to enterprise-grade
- •ANZ safety regulations drive quality/safety product; then scaled globally
- 30:53 – 33:24
International expansion playbook: brand first, references first, patience always
Tooey explains that international growth is not a copy-paste of the U.S. approach. The winning sequence is to establish brand credibility and reference customers via customer success and marketing before fully deploying a go-to-market engine.
- •Avoid assuming U.S. playbooks transfer unchanged to new markets
- •Start with customer success + field/product marketing to build references
- •Then deploy full go-to-market teams to capitalize on established trust
- •Construction workflows are globally similar, yielding ~85% product fit in many regions
- 33:24 – 37:22
Pricing and CEO craft: volume-based model, customer intimacy, and capital allocation
Tooey defends Procore’s volume-based pricing as essential to connecting everyone in construction, since seat-based pricing discourages broad collaboration. He also describes his CEO boundaries (no deal negotiations, daily customer calls) and why capital allocation is a top CEO responsibility.
- •Seat-based pricing would limit access; construction requires whole-team participation
- •Volume-based yardstick aligns with how customers buy (e.g., insurance by volume)
- •CEO rule: build relationships, avoid transactional negotiations; talk to customers daily
- •Capital allocation as core CEO job; emphasizes decision speed with controlled blast radius
- 37:22 – 1:14:52
Leading at scale: delegation, hiring for values, authenticity, and life beyond the CEO role
The conversation shifts to leadership realities: stopping ‘doing’ and starting ‘leading,’ letting teams fail safely, and hiring to values (hungry, humble, smart). Tooey shares imposter syndrome as a college-dropout CEO, his reliance on a trusted ‘cabinet,’ and the hard tradeoffs between company, parenting, and marriage—plus his decompression rituals like building complex Lego sets.
- •Leadership transition: empower others; allow failure with minimized blast radius
- •Culture system: hire for ‘hungry, humble, smart’; culture becomes self-enforcing
- •Imposter syndrome at investor conferences; breakthrough via authenticity and vulnerability
- •Personal balance: regrets about time with son; marriage firewall from Procore; stress resets via alone time/Lego
- 1:14:52 – 1:25:06
Quick-fire insights: luck vs persistence, cofounder conflicts, advice, and what’s next
In rapid Q&A, Tooey attributes success more to persistence and luck than traditional ‘skill,’ recounts pivotal life moments, and shares a $100 hat fight with his cofounder over resource allocation. He closes with reflections on role models, productivity advice, a few personal splurges, and a 10-year vision centered on building at his ranch.
- •Success ingredients: persistence high, luck meaningful; skill framed as persistence
- •Pivotal moments: switching from construction to tech; deciding to start Procore
- •Cofounder disagreements often about spending; symbolic ‘$100 hats’ story
- •Best advice: ‘If you have five minutes, do a five-minute job’; future: building on his ranch
