Prologue — Why I Don’t Wear the “Angel” Badge
I’ve been called many things over the last twenty-five years — builder, firefighter, lunatic who ships too fast — but never “angel investor.” That hat doesn’t fit. My craft is starting companies, scaling them until the paint peels, then handing the wheel to the next driver while I chase the next blank canvas.
Along the way I’ve worked with phenomenal operator-turned investors and seen, up close, how a true builder’s mindset can change a startup’s destiny. This article distills those lessons. It isn’t investment advice; it’s a founder’s field guide to picking the right partners on your cap table. Each chapter spotlights a world-class operator-VC whose public story underlines the principle at hand.
Need the copy-paste list of 100 operator VCs & angels my team tracks? DM me on LinkedIn with your email. I’m not an investor, but I’m happy to share the spreadsheet so builders can find the right allies.
Product Intuition — Seeing Around Corners
My product life began in 1998 wiring AddAShop so mom-and-pop retailers could sell online. Success came from spending Saturdays in those shops, watching owners click, curse, and occasionally cheer. That user empathy became my default OS for every venture since.
Operator-investors share that reflex. Dylan Field turned Figma into design’s command center by refusing to ship until browser-based multiplayer felt magical. Founder reviews with Dylan dive into pixel-level UX, not vanity TAM slides.
As a founder, I filter potential investors exactly how customers once filtered my early products: “Show me, in five minutes, how you’d improve what we’ve built so far.” Operators light up; PowerPointers glaze over.
Crisis Leadership — When the Suits Vanish and the Operators Step Up
The harshest lesson I ever learned about board composition came in the AddAShop era. At twenty-something, I was flattered to land two top-tier investment bankers as directors.
They’d just shepherded my European distribution partner through a $1-billion Milan IPO and were eager to run the same “blitz-scale, list, cash-out” playbook in the U.S. I was young, impressionable, and star-struck by the war stories and leather briefcases—so I let them floor the gas: head-count optics, burn-rate optics, the whole late-’90s champagne script.
Then the dot-com bubble burst. Revenue forecasts vaporized, capital markets froze, and those same bankers—who only months earlier insisted we “bruise the throttle harder”—stopped returning calls. No war room, no mitigation plan, just radio silence. I still remember standing in an empty conference room, dialing their numbers on repeat while payroll loomed. That’s when “board pedigree” lost its charm forever and “operational scar tissue” earned my lifelong respect.
Contrast that vanishing-act with Max Levchin’s response during PayPal’s near-death fraud spiral. When hourly losses hit $2,300, Max didn’t draft a memo or duck behind PR. He dove into the codebase, hacked together CAPTCHAs, and built anomaly-detection heuristics that slammed fraud to near zero within weeks. Same existential pressure, radically different reflex.
That’s the dividing line for me now:
- Bankers under stress ghost you.
- Operators under stress get greasy elbows and solve.
So when I vet investors, I replay the AddAShop memory and ask a single litmus question:
“Describe the last time you personally pulled a company back from the brink—what did you do in the first 24 hours?”
If the answer involves dashboards, kludged scripts, or hard conversations with customers, I lean in. If it involves “advising management” and “monitoring the situation,” I swipe left.
GTM Execution — Hustle Beats Hype
graph8 reached its first ten customers the gritty way: I cold-called, demoed, and customized flows myself. Joe Lonsdale once told me, “Hire engineers for every role.” I stretched that mantra into GTM: instrument everything, test, iterate, automate.
Look at Tony Xu. DoorDash began with the founders personally delivering pad thai in Palo Alto. That unscalable hustle created insights competitors missed.
When I pick investors, I ask, “Describe the last customer you closed personally.” If the answer involves back seats of Ubers and duct-taped Zapier workflows, lean in. If it happens in a Park Avenue boardroom, hard pass.
Hiring & Culture — Engineers in Every Seat
Joe’s advice reshaped Adility: our customer-success lead wrote SQL; our biz-dev guy grepped logs. That high-agency DNA still drives graph8.
Few people articulate hiring better than Cristina Cordova (early Stripe & Notion, now COO at Linear). Her public talks hammer why early hires must be IC-heavy Swiss-army knives. When Cristina invests, she helps founders draft scorecards that weight initiative over pedigree.
To refine my own hiring playbooks, I borrow heavily from Dylan Field’s public interviews on screening for product taste and from Claire Hughes Johnson’s book Scaling People, which lays out leveling frameworks and decision-memo rituals. Their documented methods—honed at Figma and Stripe—are worth a thousand generic HR templates.
Empathy & Founder Psychology — Walking in the Entrepreneur’s Shoes
Startup life pulverizes your psyche. I still recall pacing at 3 a.m. before a major acquisition closed, rehearsing every worst-case scenario. An empathetic investor would have been a luxury; but at this time I was beyond that support, building companies just with operators (who I mentor) and not with investors, but if you find yourself here, having that sounding board is key.
Tristan Handy (dbt Labs) says helping the next cohort of founders is “an absolute joy.” I’ve felt that. When COVID and later the Ukraine war kneecapped two of my companies we had many late-night Zooms strategizing retention moves with my partners. We shared scar tissue, not platitudes.
Empathy shows up in tone: if an investor’s first reaction to bad news is “How are you holding up?”—keeper. If it’s “How does this affect my liquidation stack?”—next.
Networks & Credibility — The Mafia Effect
Operators accrue networks the way beavers build dams—stick by stick over decades. I’ve bartered mine into customer intros, VP hires, and guidance for regulatory set up.
Nobody weaponizes network like Naval Ravikant, who turned operator credibility into AngelList’s deal-flow hydra. A Naval endorsement blows doors off hinges. Coincidentally Naval and I were on the same office floor in a shared office service when he started Angel List. I still remember peaking my head into his office to get his help setting upm our Angel List listing, and he immediately jumped in.
I want investors whose LinkedIn inbox beats my own. If their contact list is stacked with builders—not bankers—cap-table chemistry is right.
Conclusion — Capital Is Commodity; Capability Compounds
I build companies; I don’t underwrite them. But after seven ventures, one truth endures: money funds momentum; operators accelerate it.
Founders, steal that checklist—or tweak it to taste. You don’t need investors who can recite multiples and are spreadsheet jockeys; you need partners who help you survive midnight outages, land lighthouse customers, and hire missionaries.
I’m a serial entrepreneur; my currency is urgency and outcomes. Operator-investors are the accelerants I mix into the fuel. Choose yours wisely, and I’ll see you somewhere on the other side of the messy middle—shipping, scaling, and starting again.
