Founding Moments

David Leeds spent nearly two decades building Tango Card from his basement in West Seattle — literally fulfilling gift card orders at midnight — into a company processing over $1.5 billion in rewards annually before being acquired by Blackhawk Network. But before Tango, he co-founded Fiber Tower, pitched 45 venture capital firms, got 45 rejections, and took it public anyway.What comes through in this conversation is his instinct for timing. He started Tango in January 2009, right in the teeth of the financial crisis, because he believed that was exactly the right moment. Then he threw out the existing playbook entirely — no delivery fees, no platform minimums, no reporting fees — in an industry where 15 to 30% fee stacks were completely normal. Microsoft was his first customer. Their finance team all closed their laptops when he explained the model.Show NotesTango Card — acquired by Blackhawk Network (2023)Fiber Tower — telecom infrastructure, taken public via reverse merger (2007)Bing Rewards — Microsoft loyalty program, one of Tango's first integrationsgiftcertificates.com — Omaha-based competitor acquired by Tango post-fundraiseBlackhawk Network / Silver Lake — acquirer of Tango CardTimestamps[00:32] Growing up, studying abroad in Copenhagen, and choosing a program where English wasn't the native language[04:17] Nations Bank, Lexmark, and presenting to French leadership in broken French[06:38] Starting a consulting company in China — and why he hated being a consultant within a year[08:40] Stanford during the dot-com peak, graduating right as everything crashed[09:29] Founding Fiber Tower: four folding desks, no windows, 45 VC rejections[17:55] The core lesson: start a company when the economy is in ruins[20:10] January 2009 — launching Tango Card, self-funded, in the financial crisis[23:28] How a research note about gift card payment growth became a $1.5B business[35:52] The original product: a physical card, a website, and midnight basement fulfillment[39:30] Landing Microsoft as customer #1 and the moment their whole finance team closed their laptops[44:05] The business model that changed everything: zero fees, just spend your budget[54:38] Building a self-serve portal — and why his CTO tried to talk him out of it[1:06:29] How David recruited and kept great people through transparency and a mission everyone could actually recite[1:12:21] The Blackhawk acquisition — why global reach was the whole point[1:19:22] Why a gift card company keeps a sledgehammer in the office

Renato Villanueva went from struggling to land a job out of UVU to helping build Divvy into a billion-dollar exit — then quit his job on a whim to start Parallel, an AI-powered financial modeling tool for founders. In this episode, Renato gets brutally honest about pre-selling a product that didn't exist, pricing mistakes that cost them 30% of their customers, and why he ultimately stepped down as CEO of his own company.Key Moments:[00:53] — Renato's unlikely career path: from cold-emailing Signal Peak for free work to landing at Divvy and riding it to acquisition.[03:49] — How he raised $200K the same night he quit his job — and why fundraising is exactly like dating.[08:00] — Selling Gab Wireless an annual contract before a single line of product existed.[10:40] — The pre-selling trap: why saying yes to every customer feature request nearly broke the company.[11:17] — Churning 30% of customers in early 2025 and what they learned from it.[15:13] — The real way to figure out pricing: guess, iterate, and treat every "no" as data.[17:12] — Why pricing is a treasure chest of ICP intelligence — and the mistake of ignoring what it tells you.[22:39] — Why Renato stepped down as CEO, and how his investors actually responded.[25:45] — His current obsession: the gap between hyper-personalized AI and the reality that most people are just lazy.

What happens when your startup fails — and why that might be the best thing that ever happens to you?Chris Chumley has spent his career building, breaking, and betting on software companies. From nearly getting expelled for sneaking into school to play Oregon Trail, to leading product at a venture-backed startup that cratered, to helping build CampusLogic from a handful of customers to a $50M ARR acquisition by Ellucian — Chris has seen every phase of the startup lifecycle up close.In this episode, Chris and Nate dig into the real lessons behind building great products: why your software is worth nothing (but your business is everything), how to stay differentiated when sales is screaming for me-too features, and why the best product strategy starts the moment you choose what to build.Chris also shares his framework for the "lighthouse" approach to roadmapping, what it really takes to build trust with a CEO, and why niching down — not boiling the ocean — is what took CampusLogic to $50M.Now a venture partner at Phoenix Ventures, Chris brings his operator lens to what he's seeing in early-stage investing today, including why pre-seed is getting harder, what he looks for in a founder, and why vibe coding both excites and scares him.Plus — a candid conversation about Claude Code, the future of engineering, and a question neither of them can fully answer: if AI does all the grunt work, how does the next generation actually learn?